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Strychnos 1990 - 2004 - Crops for the Future

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<strong>Strychnos</strong> <strong>1990</strong> - <strong>2004</strong><br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

F. K. Akinnifesi, F. R. Kwesiga, J. Mhango, A. Mkonda, T. Chilanga and R. Swai<br />

Domesticating priority <strong>for</strong> Miombo indigenous fruit trees as a promising livelihoo<br />

<strong>2004</strong><br />

Acta Horticulturae<br />

632, 15-30. Price(81 EURO<br />

Abstract<br />

Most countries in Sou<strong>the</strong>rn Africa are experiencing acute malnutrition, food insecurity, and low<br />

income among <strong>the</strong> rural and peri-urban population, and <strong>the</strong>se culminate in de<strong>for</strong>estation and loss of<br />

biodiversity. The Miombo woodlands are known to have over 75 indigenous fruit trees (IFTs), which<br />

bear edible fruits. The fruits are rich in minerals and vitamins, sold <strong>for</strong> cash income and constitute<br />

important food sources during famines and or emergencies. This paper provides an overview of<br />

some ef<strong>for</strong>ts to domesticate <strong>the</strong> IFTs identified by farmers and users as priority species, as an<br />

important step to provide opportunities <strong>for</strong> resource-poor farmers to cultivate and generate income<br />

from sale of fresh and processed products, and to conserve <strong>the</strong> genetic potential of <strong>the</strong>se species. The<br />

approach used involves four basic steps: (1) identification of priority species by communities and<br />

o<strong>the</strong>r users, (2) participatory selection of superior trees and naming <strong>the</strong>m in situ, (3) propagation and<br />

cultivation of trees as fruit orchards, and (4) dissemination and adoption. Uapaca kirkiana, Parinari<br />

curatellifolia, <strong>Strychnos</strong> cocculoides and Sclerocarya birrea have been identified by farmers and<br />

stakeholders as priority species <strong>for</strong> domestication in <strong>the</strong> sou<strong>the</strong>rn Africa region. Germplasm of<br />

Uapaca and Sclerocarya were collected, exchanged among countries, and tested in multilocational<br />

provenance trials. Over 5000 farmers in four countries are involved in on-farm testing of IFTs in <strong>the</strong><br />

field and homesteads. A new domestication strategy is developed <strong>for</strong> <strong>the</strong> participatory domestication<br />

of U. kirkiana, using <strong>the</strong> rapid clonal selection approach. A strong network of stakeholders and<br />

farmers has shown strong enthusiasm, commitment, and participation in <strong>the</strong> domestication of IFTs.<br />

Creation of an enabling environment through policy re<strong>for</strong>ms and market development will be<br />

essential to achieve socio-economic empowerment of <strong>the</strong> resource-poor farmers in <strong>the</strong> region<br />

through domestication, utilization and commercialization of fruits and products. There is a need <strong>for</strong><br />

product development research, private sector involvement and strong policy support in order to have<br />

t a n g i b l e i m p a c t .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

H. W. Pritchard, M. I. Daws, B. J. Fletcher, C. S. Gamene, H. P. Msanga and W.<br />

Ecological correlates of seed desiccation tolerance in tropical African dryland tree<br />

<strong>2004</strong><br />

American Journal of Botany<br />

91(6): 863-870<br />

Abstract<br />

In <strong>the</strong> tropics, species with recalcitrant or desiccation-sensitive, Type III seeds are largely restricted<br />

to regions with comparatively high rainfall, because desiccation-induced seed death will be minimal<br />

in <strong>the</strong>se environments. However, species with recalcitrant seeds do occur in drylands, although little<br />

is known about ecological adaptations to minimize seed death in <strong>the</strong>se environments. Here, we<br />

present data <strong>for</strong> <strong>the</strong> seed desiccation tolerance of 10 African dryland species (Dovyalis caffra, Khaya<br />

senegalensis, Kigelia africana, Lannea microcarpa, Sclerocarya birrea, <strong>Strychnos</strong> cocculoides,<br />

Syzygium cumini, Trchilia emetica, Vitellaria paradoxa and Ximenia americana) and examine <strong>the</strong><br />

relationships between seed size, rainfall at <strong>the</strong> time of seed shed, and desiccation tolerance <strong>for</strong> <strong>the</strong>se<br />

and a fur<strong>the</strong>r 70 species from <strong>the</strong> scientific literature. The combined data set encompasses species<br />

from 33 families. Three species (Syzygium cumini, T. emetica, and V. paradoxa) had desiccationsensitive<br />

seeds, and <strong>the</strong> remaining seven species investigated were desiccation-tolerant. The<br />

desiccation-sensitive species had large (>0.5 g) seeds, germinated rapidly, and had comparatively<br />

small investments in seed physical defenses. Fur<strong>the</strong>rmore, seed was shed in months of high rainfall<br />

(>60 mm). In comparison, <strong>for</strong> species with desiccation-tolerant seeds, seed mass varied across five<br />

orders of magnitude, and seed was shed in wet and dry months. Although infrequent in dryland<br />

environments (approximately 11% of <strong>the</strong> species examined here), species with desiccation-sensitive<br />

seeds do occur; large size, rapid germination, and <strong>the</strong> timing of dispersal all reduce <strong>the</strong> likelihood of<br />

seed drying. Fur<strong>the</strong>rmore, desiccation-sensitivity may be advantageous <strong>for</strong> large-seeded species by<br />

increasing <strong>the</strong> efficiency of resource use in seed provisioning.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Brochado, C. D., A. P. de Almeida, B. P. Barreto, L. P. Costa, L. S. Ribeiro, R. L.<br />

Flavonol robinobiosides and rutinosides from Alternan<strong>the</strong>ra brasiliana (Amaranth<br />

2003<br />

Journal of <strong>the</strong> Brazilian Chemical Society<br />

14(3): 449-451<br />

Abstract<br />

The extract of <strong>the</strong> medicinal species Alternan<strong>the</strong>ra brasiliana Kuntze af<strong>for</strong>ded six di- and triglycosyl<br />

kaempferol and quercetin derivatives. Their structures were elucidated based on <strong>the</strong> H-1- and C-13-<br />

NMR data and are reported here <strong>for</strong> <strong>the</strong> first time in this genus. Kaempferol 3-O-robinobioside and<br />

kaempferol 3-O-rutinoside significantly inhibited <strong>the</strong> human lymphocyte proliferation in vitro.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Frederich, M., M. Bentires-Ali, M. Tits, L. Angenot, E. Heinen and M. C. De Pau<br />

Apoptosis induction in human cancer cells by sungucine from <strong>Strychnos</strong> icaja root<br />

2003<br />

Naunyn-Schmiedebergs Archives of Pharmacology<br />

367(3): 260-265<br />

Abstract<br />

Sungucine (SG) and isosungucine (ISG) are bisindole alkaloids characterized by a 5'-23 link between<br />

<strong>the</strong> two parts of <strong>the</strong> compounds, which are till now specific to <strong>Strychnos</strong> icaja. In this work, SG and<br />

ISG were submitted to <strong>the</strong> NCI's in vitro 60 human tumor cell line screen, where SG showed<br />

interesting selectivity (6X) against <strong>the</strong> tested leukemia cell lines. In HL60-treated cells, apoptosis<br />

was demonstrated by observation of apoptotic bodies <strong>for</strong>mation, and phosphatidylserine exposition<br />

at cell surface. In HeLa-treated cells, <strong>the</strong> analysis of cellular cycle by flow cytometry showed G1<br />

accumulation and a small sub-G1 peak that could be related to DNA fragmentation characteristic of<br />

apoptosis. The eventual role of p53 was analyzed using wild-type HCT-116 colon cancer cells.<br />

Never<strong>the</strong>less, p53 and Bax expression were not modified in SG-treated cells. The cleavage of PARP<br />

by caspase-3 protease proved that apoptosis was also induced in this line. These results demonstrate<br />

that SG induces apoptosis, but also necrosis, in human cancer cell lines.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Frederich, M., M. Bentires-Alj, M. Tits, L. Angenot, R. Greimers, J. Gielen, V. B<br />

Isostrychnopentamine, an indolomonoterpenic alkaloid from <strong>Strychnos</strong> usambaren<br />

2003<br />

Journal of Pharmacology and Experimental Therapeutics<br />

304(3): 1103-1119<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Mukherjee, R. and P. A. Keifer<br />

Warifteine and methylwarifteine: H-1 and c-13 assignments by two-dimensional<br />

2003<br />

Magnetic Resonance in Chemistry<br />

41(3): 213-218<br />

Abstract<br />

The identity and structures of warifteine and methylwarifteine, two tertiary bisbenzylisoquinoline<br />

alkaloids of an unusual type, were elucidated and verified by 2D NMR spectroscopy. Complete H-1<br />

and C-13 NMR spectral assignments were obtained. Copyright (C) 2003 John Wiley Sons, Ltd.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Philippe, G., P. De Mol, M. Zeches-Hanrot, J. M. Nuzillard, M. H. Tits, L. Angen<br />

Indolomonoterpenic alkaloids from <strong>Strychnos</strong> icaja roots<br />

2003<br />

Phytochemistry<br />

62(4): 623-629<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Reddy, M. S. and N. Parthasarathy<br />

Liana diversity and distribution in four tropical dry evergreen <strong>for</strong>ests on <strong>the</strong> Coro<br />

2003<br />

Biodiversity and Conservation<br />

12(8): 1609-1627<br />

Abstract<br />

Liana diversity was inventoried in four tropical dry evergreen <strong>for</strong>est sites that are characterized by<br />

numerous trees, of short stature and small diameter, and a varying degree of anthropogenic<br />

disturbance, on <strong>the</strong> Coromandel coast of south India. A 1-ha plot was established in each of <strong>the</strong> four<br />

sites and was subdivided into 100 quadrats of 10 m x 10 m. All lianas greater than or equal to1 cm<br />

diameter at breast height (dbh) rooted within <strong>the</strong> plot were enumerated. The species richness and<br />

density of lianas, with respect to site disturbance and <strong>for</strong>est stature, varied across <strong>the</strong> sites. Liana<br />

density totaled 3307 individuals (range 497-1163 individuals ha(-1)) and species richness totaled 39<br />

species (range 24-29 species ha(-1)) representing 34 genera and 24 families. Combretaceae,<br />

Asclepiadaceae, Capparaceae and Vitaceae were <strong>the</strong> well-represented families. The top five species<br />

<strong>Strychnos</strong> minor, Combretum albidum, Derris ovalifolia, Jasminum angustifolium and Reissantia<br />

indica contributed 55% of total density. The slopes of <strong>the</strong> species-area curves were different <strong>for</strong> each<br />

of <strong>the</strong> four sites and <strong>the</strong> curve stabilized in only one site. Of <strong>the</strong> four climbing modes recognized<br />

among <strong>the</strong> total 39 species, 18 were twiners (56% of <strong>the</strong> total density). Eight species (24% of<br />

density) were tendril climbers and 12 species (16% of density) were scramblers. Hugonia mystax<br />

was <strong>the</strong> only hook climber. All <strong>the</strong> 39 species and 88% of liana density were encountered within a<br />

category of 6 cm dbh or less, and a similar pattern prevailed in <strong>the</strong> individual sites. Of <strong>the</strong> three<br />

diaspore dispersal modes found among <strong>the</strong> 39 liana species, animal (64%) and wind (23%) dispersal<br />

were predominant over <strong>the</strong> autochorous mode (13%). Liana diversity and distribution in dry <strong>for</strong>est<br />

communities appear to be influenced by <strong>for</strong>est stature and site disturbance levels. In <strong>the</strong> light of <strong>the</strong><br />

extent of liana diversity and sacred grove status of <strong>the</strong> study sites, <strong>the</strong> need <strong>for</strong> <strong>for</strong>est conservation,<br />

i n v o l v i n g l o c a l p e o p l e , i s e m p h a s i z e d .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Wins, P., I. Margineanu, J. Penelle, L. Angenot, T. Grisar and L. Bettendorff<br />

Bisindole alkaloids from <strong>Strychnos</strong> guianensis are effective antagonists of nicotini<br />

2003<br />

Naunyn-Schmiedebergs Archives of Pharmacology<br />

367(3): 253-259<br />

Abstract<br />

Several mono- and bisindole quaternary alkaloids isolated from <strong>the</strong> stem bark of <strong>Strychnos</strong><br />

guianensis have recently been shown to be effective blockers of neuromuscular transmission in mice.<br />

In this study, we used a human clonal cell line (TE671) expressing muscle-type nicotinic<br />

acetylcholine receptors. The agonist carbamylcholine activated a receptor-mediated Rb-86(+) efflux<br />

and this activation was antagonized by <strong>the</strong> indole alkaloids, <strong>the</strong> most active being bisindole<br />

bisquaternary compounds. The most effective antagonist, guiachrysine, had an IC50 around 0.43<br />

muM in <strong>the</strong> presence of 0.5 mM carbamylcholine, compared to 0.16 muM <strong>for</strong> d-tubocurarine, <strong>the</strong><br />

most potent curarizing alkaloid. Guiaflavine and 5',6'-dehydroguiaflavine were slightly less effective.<br />

Monoindole compounds were 10 to 100 times less potent than bisindole alkaloids. Kinetic analysis<br />

showed that <strong>the</strong> inhibition of <strong>the</strong> carbamylcholine-dependent Rb-86(+) efflux by guiaflavine was of<br />

mixed competitive and uncompetitive type. The competitive component (K-I = 0.21 muM) is<br />

presumably due to binding at <strong>the</strong> acetylcholine site, while <strong>the</strong> uncompetitive component (K'(I) = 0.92<br />

m u M ) m a y b e d u e t o o p e n c h a n n e l b l o c k .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Zlotos, D. P.<br />

Iso-caracurine v, a novel unexpected decomposition product of caracurine v<br />

2003<br />

Journal of Natural Products<br />

66(1): 119-120<br />

Abstract<br />

The structure of iso-caracurine V (3), an unexpected decomposition product of <strong>the</strong> <strong>Strychnos</strong><br />

alkaloid caracurine V (1), was determined by NMR spectroscopy. Compound 3, which was probably<br />

previously regarded as bisnortoxiferine I (2), is a one-sided ring closed product of 2.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Belem-Pinheiro, M. L., R. P. C. Couceiro, A. F. I. Da Rocha, F. J. Q. Monte and J.<br />

A new strychnobrasiline base of <strong>Strychnos</strong> mattogrossensis<br />

2002<br />

Natural Product Letters<br />

16(4): 229-233<br />

Abstract<br />

A new strychnobrasiline derivative, 12-hydroxy-10, 11-dimethoxystrychnobrasiline 1, has been<br />

isolated from <strong>the</strong> stem barks of <strong>Strychnos</strong> mattogrossensis. Its structure was established by<br />

spectroscopy analysis (1D and 2D NMR, MS, IR, UV) and literature data comparison. Two o<strong>the</strong>r<br />

known indoline alkaloids were also obtained from <strong>the</strong> heartwood, 12-hydroxy-11-<br />

methoxystrychnobrasiline 2 and strychnobrasiline 3.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bennasar ML; Zulaica E; Alonso Y; Vidal B; Vazquez JT; Bosch J<br />

Addition of chiral enolates to n-alkyl-3-acylpyridinium salts. Total syn<strong>the</strong>sis of (+<br />

2002<br />

Tetrahedron-Asymmetry<br />

13(1): 95-106<br />

Abstract<br />

Chiral enolates of indolylacetyl derivatives 6a-f undergo addition to pyridinium salt 7 with complete<br />

trans-selectivity and varied diastereofacial selectivities to give, after acid-induced cyclization of <strong>the</strong><br />

intermediate 1,4-dihydropyridines, <strong>the</strong> vinoxine-related tetracycles 8a-f. Starting from (S)-prolinol<br />

indolylacetamide 6e, subsequent elaboration of <strong>the</strong> ethylidene substituent from tetracycle 8e and<br />

removal of <strong>the</strong> chiral auxiliary has resulted in a straight<strong>for</strong>ward syn<strong>the</strong>sis of (+)-16-epivinoxine and<br />

(-)-vinoxine. (C) 2002 Elsevier Science Ltd. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Biswas, S., T. Murugesan, S. Sinha, K. Maiti, J. R. Gayen, M. Pal and B. P. Saha<br />

Antidiarrhoeal activity of <strong>Strychnos</strong> potatorum seed extract in rats<br />

2002<br />

Fitoterapia<br />

73(1): 43-47<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Cao, H., Y. Liu and S. d. Jin<br />

Determination of strychnine and brucine in <strong>Strychnos</strong> nux vomica L. and its prepa<br />

2002<br />

Chinese Journal of Pharmaceutical Analysis<br />

22(4): 279-281<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Chan, T. Y. K.<br />

Herbal medicine causing likely strychnine poisoning<br />

2002<br />

Human and Experimental Toxicology<br />

21(8): 467-468<br />

Abstract<br />

'Maqianzi' (<strong>the</strong> dried ripe seed of <strong>Strychnos</strong> nux-vomica L.) contains 1.0-1.4% each of strychnine<br />

and brucine. After processing to reduce its toxicity, 'maqianzi' was used as a herbal remedy <strong>for</strong><br />

rheumatism, musculoskeletal injuries and limb paralysis. A 42-year old woman with neck pain was<br />

prescribed 15 g of 'maqianzi' to be taken in two doses at 7 hours apart, although <strong>the</strong> recommended<br />

dose was 0.3-0.6 g. She was apparently well after drinking <strong>the</strong> first of two bowls of 'maqianzi'<br />

decoction. One hour after she drank <strong>the</strong> second bowl of herbal decoction, she suddenly developed<br />

tonic contractions of all her limb muscles and carpopedal spasm lasting 5 min, difficulty in<br />

breathing, chest discom<strong>for</strong>t and perioral numbness. The second bowl of decoction probably became<br />

more concentrated because of evaporation of water during continued boiling and contained a larger<br />

amount of 'maqianzi'. On arrival in <strong>the</strong> hospital 1 hour later, she complained of muscle pain and<br />

tiredness. She was found to have hyperventilation and weakness of four limbs, with muscle power of<br />

grade 5(-)/5. All her symptoms gradually subsided over <strong>the</strong> next few hours. This case illustrated that<br />

'maqianzi' can cause strychnine poisoning even after processing, especially when <strong>the</strong> recommended<br />

dose is greatly exceeded. In any patient with 'unexplained' muscle spasms or convulsions, strychnine<br />

poisoning should be included in <strong>the</strong> differential diagnosis and <strong>the</strong>y should be asked about <strong>the</strong> use of<br />

h e r b a l m e d i c i n e s .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Ergun, Y., S. Patir and G. Okay<br />

Syn<strong>the</strong>sis of <strong>the</strong> azocino[4,3-b]indole core structure <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of strychnos<br />

2002<br />

Journal of Heterocyclic Chemistry<br />

39(2): 315-318<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Frederich, M., M. J. Jacquier, P. Thepenier, P. De Mol, M. Tits, G. Philippe, C. D<br />

Antiplasmodial activity of alkaloids from various <strong>Strychnos</strong> species<br />

2002<br />

Journal of Natural Products<br />

65(10): 1381-1386<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Hokelek, T., S. Patir, Y. Ergun and G. Okay<br />

Ethyl 9h-1,2,3,4-tetrahydrocarbazole-3-carboxylate<br />

2002<br />

Acta Crystallographica Section E Structure Reports Online<br />

58(NOV): O1255-O1257<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Hosagoudar, V. B. and S. Shiburaj<br />

Meliola gamsii sp nov (ascomycetes, meliolales) from Kerala, India<br />

2002<br />

Nova Hedwigia<br />

74(3-4): 411-413<br />

Abstract<br />

The new species Meliola gamsii is described from <strong>the</strong> host plant <strong>Strychnos</strong> mix-vomica from Kerala,<br />

I n d i a .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Khumalo, L. W., L. Majoko, J. S. Read and I. Ncube<br />

Characterisation of some underutilised vegetable oils and <strong>the</strong>ir evaluation as starti<br />

2002<br />

Industrial <strong>Crops</strong> and Products<br />

16(3): 237-244<br />

Abstract<br />

Oils were extracted from <strong>the</strong> inner skin of <strong>Strychnos</strong> madagascariensis fruit shell, Trichelia emetica<br />

seed and Ximenia caffra seed. Gas chromatography analysis of methyl esters of <strong>the</strong> glycerides of<br />

<strong>the</strong>se oils was used to determine <strong>the</strong> fatty acid profiles of <strong>the</strong> oils. S. madagascariensis and X. caffra<br />

oils were found to contain high oleic acid levels, 68 and 59% respectively, while T emetica oil was<br />

found to contain 53% palmitic acid. Pancreatic lipase digestion was used to per<strong>for</strong>m structural<br />

analyses on <strong>the</strong> triglycerides of oils. Oleic acid was found to be concentrated at <strong>the</strong> 2-position of <strong>the</strong><br />

triglycerides of <strong>the</strong> X caffra and T emetica oils. The three oils were evaluated <strong>for</strong> use as starting<br />

materials in lipase-catalysed production of cocoa butter equivalents using transesterification<br />

reactions. A 1,3-specific lipase from Rhizomucor miehei was used to incorporate stearic acid and<br />

palmitic acid into <strong>the</strong> 1- and 3-positions of <strong>the</strong> triglycerides. The products of <strong>the</strong> transesterifications<br />

in <strong>the</strong> case of X caffra and S. niadagascariensis compare well with those produced using lipasecatalysed<br />

transesterifications of o<strong>the</strong>r oils. (C) 2002 Elsevier Science B.V. All rights reserved.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Lansiaux, A., C. Bailly, C. Houssier, P. Colson, M. C. De Pauw-Gillet, M. Frederi<br />

Apoptosis of hl-60 leukemia cells induced by <strong>the</strong> bisindole alkaloids sungucine an<br />

2002<br />

Planta Medica<br />

68(7): 591-595<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Lynch, S. M., S. K. Bur and A. Padwa<br />

Intramolecular amidofuran cycloadditions across an indole pi-bond: An efficient a<br />

2002<br />

Organic Letters<br />

4(26): 4643-4646<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Martin, S. F.<br />

Evolution of <strong>the</strong> vinylogous mannich reaction as a key construction <strong>for</strong> alkaloid sy<br />

2002<br />

Accounts of Chemical Research<br />

35(10): 895-904<br />

Abstract<br />

The vinylogous Mannich reaction is rapidly emerging as an important process <strong>for</strong> <strong>the</strong> construction of<br />

derivatives of delta-aminocarbonyl compounds. Because <strong>the</strong> iminium and dienol components<br />

employed in this addition may be ei<strong>the</strong>r acyclic or cyclic, a wide variety of adducts may be quickly<br />

assembled. These intermediates may <strong>the</strong>n in turn be converted into a broad array of alkaloids and<br />

substituted nitrogen heterocycles. We have developed a number of variations of this reaction and<br />

have applied some of <strong>the</strong>m to <strong>the</strong> concise syn<strong>the</strong>ses of a number of structurally diverse and complex<br />

alkaloid natural products. Many of <strong>the</strong>se results are presented in a historical context in this Account.


Author<br />

Title<br />

Year<br />

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Reference<br />

Mitaine-Offer, A. C., M. Sauvain, A. Valentin, J. Callapa, M. Mallie and M. Zech<br />

Antiplasmodial activity of aspidosperma indole alkaloids<br />

2002<br />

Phytomedicine<br />

9(2): 142-145<br />

Abstract<br />

The antiplasmodial activity of twelve alkaloids with an aspidospermane skeleton was estimated in<br />

vitro on chloroquine-resistant and sensitive strains of Plasmodium falciparum. Seven tetracyclic<br />

alkaloids possessing a free ethyl chain such aspidospermine, showed IC50 after incubation <strong>for</strong> 72 h<br />

between 3.2 and 15.4 muM. Moreover, four pentacyclic alkaloids with ethyl chain included in a<br />

tetrahydrofuran, such haplocine, showed a reduced activity, with IC50, after 72 h, between 22.6 and<br />

52.6 muM. According to <strong>the</strong>se results, a chloroquine-potentiating experiment was also per<strong>for</strong>med<br />

with two of <strong>the</strong> most active compounds. Isobolograms were obtained and demonstrated a synergic<br />

effect of N-<strong>for</strong>myl-aspidospermidine and aspidospermine when associated with chloroquine. The<br />

cytotoxicity and <strong>the</strong> selectivity index of some alkaloids were also estimated.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Ohshima, T., J. Y. Xu, R. Takita, S. Shimizu, D. F. Zhong and M. Shibasaki<br />

Enantioselective total syn<strong>the</strong>sis of (-)-strychnine using <strong>the</strong> catalytic asymmetric m<br />

2002<br />

Journal of <strong>the</strong> American Chemical Society<br />

124(49): 14546-14547<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Padwa, A., T. M. Heidelbaugh, J. T. Kue<strong>the</strong>, M. S. McClure and Q. Wang<br />

Tandem pummerer/mannich cyclization cascade of alpha-sulfinylamides as a meth<br />

2002<br />

Journal of Organic Chemistry<br />

67(17): 5928-5937<br />

Abstract<br />

A series of alpha-sulfinylenamides was conveniently prepared by <strong>the</strong> condensation of a primary<br />

amine with a ketone, followed by reaction of <strong>the</strong> resulting imine with ethylsulfenylacetyl chloride<br />

and subsequent oxidation with sodium periodate. When treated with p-TsOH, cyclization occurred to<br />

produce fused isoquinoline lactams by a mechanism that involves an initial Pummerer reaction<br />

followed by a subsequent cyclization of <strong>the</strong> resulting N-acyliminium ion onto <strong>the</strong> te<strong>the</strong>red aromatic<br />

ring. The isolation of a single diastereomer was rationalized in terms of a Nazarov-type 4pielectrocyclic<br />

reaction followed by pi-cyclization onto <strong>the</strong> least hindered side of <strong>the</strong> N-acyliminium<br />

ion. Ano<strong>the</strong>r method that was used to generate <strong>the</strong> alpha-acylthionium ion intermediate involved <strong>the</strong><br />

reaction of bis(ethylsulfenylacetyl)acetamides with dimethyl(methyl)thiosulfonium tetrafluoroborate<br />

(DMTSF). Treatment of several bis-ethylsulfenylenamides with DMTSF delivered novel<br />

spiroheterocycles as single diastereomers in good yield by a related process. The convergency and<br />

stereochemical control associated with this cascade sequence make it particularly suited <strong>for</strong> <strong>the</strong><br />

assembly of natural product scaffolds. Some preliminary studies were directed toward both<br />

mesembrine and deethylibophyllidine. When <strong>the</strong> model Z-enamido sulfoxide 33 was heated with p-<br />

TsOH, a 80% yield of tosylate 34 was obtained as a single diastereomer. In this case, <strong>the</strong> carbocation<br />

intermediate derived from cyclization onto <strong>the</strong> terminal pi-bond was trapped with p-TsOH from <strong>the</strong><br />

least hindered face, opposite <strong>the</strong> angular carbomethoxy and methyl groups. Related cyclization<br />

cascades were also found to occur with systems containing te<strong>the</strong>red indole rings.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Philippe G; Prost E; Nuzillard JM; Zeches-Hanrot M; Tits M; Angenot L; Frederi<br />

Strychnohexamine from <strong>Strychnos</strong> icaja, a naturally occurring trimeric indolomon<br />

2002<br />

Tetrahedron Letters<br />

43(18): 3387 - 3390<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Raghuwanshi PK; Mandloi M; Sharma AJ; Malviya HS; Chaudhari S<br />

Improving filtrate quality using agrobased materials as coagulant aid<br />

2002<br />

Water Quality Research Journal of Canada<br />

37(4): 745-756<br />

Abstract<br />

In <strong>the</strong> present study, an evaluation of agrobased materials (ABM) as a coagulant aid in conjunction<br />

with alum has been conducted to determine <strong>the</strong>ir efficacy in water treatment. The agrobased<br />

materials evaluated are Surjana seed (Moringa oleifera), Nirmali seed (<strong>Strychnos</strong> potatorum) and<br />

maize (Zeemays). Experiments have been conducted simulating a conventional water treatment train<br />

consisting of coagulation-flocculation-settling and granular media filtration. Emphasis has been<br />

given to <strong>the</strong> filtration aspect of <strong>the</strong> treatment train using syn<strong>the</strong>tic turbid water. The filter<br />

per<strong>for</strong>mance was defined by water quality and head loss development across <strong>the</strong> filter bed. When<br />

Nirmali seed or maize was used as a coagulant aid, <strong>the</strong> alum dose required was 25 and 15 mg/L,<br />

respectively, and <strong>the</strong> filtrate turbidity achieved was less than 0.2 NTU, whereas alum alone with a<br />

dose of 45 mg/L achieved filtrate turbidity levels higher than 1 NTU. Thus, <strong>the</strong> use of ABM<br />

improved <strong>the</strong> filtrate quality. Head loss in filter with Surjana seed and Maize as coagulant aids was<br />

comparable to that of alum alone, whereas it was higher when Nirmali seed was used as a coagulant<br />

a i d .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Rasoanaivo, P., M. T. Martin, E. Guittet and F. Frappier<br />

New contributions to <strong>the</strong> structure elucidation and pharmacology of <strong>Strychnos</strong> alk<br />

2002<br />

Studies in Natural Products Chemistry<br />

26: 1029-1072<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rukuni D; Mukwekwerere M<br />

Community participation in choosing indigenous fruit tree species <strong>for</strong> planting in<br />

2002<br />

Tree Seed News<br />

5: 1-4<br />

Abstract<br />

This paper presents <strong>the</strong> priority indigenous fruit tree species: Adansonia digitata, Azanza garckeana,<br />

Berchemia discolor, Diospyros mespili<strong>for</strong>mis, Flacourtia indica, Grewia spp., Sclerocarya birrea,<br />

<strong>Strychnos</strong> madagascariensis, S. cocculoides, Trichilia emetica, Uapaca kirkiana, Vangueria spp., and<br />

Vitex payos, identified by <strong>the</strong> local communities in a participatory rural appraisal conducted in five<br />

districts: Hwange and Bubi in Matebeleland North, Zaka and Mwenezi in Masvingo, and Beitbridge<br />

in Matebeleland South, in Zimbabwe. Some recommendations of <strong>the</strong> local communities regarding<br />

<strong>the</strong> improvement of <strong>the</strong> preferred species are also highlighted. Species such as <strong>Strychnos</strong><br />

cocculoides, Azanza garckeana, Sclerocarya birrea and Berchemia discolor, which are identified as<br />

easy to establish and fast growing, have <strong>the</strong> potential <strong>for</strong> domestication.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Tulyaganov, T. S. and F. K. Allaberdiev<br />

Alkaloids of Nitraria sibirica. Structures of nitraramidine and nitraraidine<br />

2002<br />

Chemistry of Natural Compounds<br />

38(6): 602-604<br />

Abstract<br />

Two new alkaloids nitraramidine and nitraraidine were isolated from <strong>the</strong> aerial part of Nitraria<br />

sibirica. Their structures were established using spectral data and chemical trans<strong>for</strong>mations.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Xu, Y., K. Ohori, T. Ohshima and M. Shibasaki<br />

A practical large-scale syn<strong>the</strong>sis of enantiomerically pure 3-[bis(methoxycarbonyl<br />

2002<br />

Tetrahedron<br />

58(13): 2585-2588<br />

Abstract<br />

A highly practical and efficient procedure <strong>for</strong> <strong>the</strong> large-scale (up to 6 mol) syn<strong>the</strong>sis of<br />

enantiomerically pure (R)-3-[bis(methoxycarbonyl)methyl]cyclohexanone using an (R)-<br />

AlLibis(binaphthoxide) complex ((R)-ALB)-catalyzed asymmetric Michael reaction was developed.<br />

The reaction was successfully accelerated under highly concentrated conditions without lowering<br />

chemical yield or <strong>the</strong> high enantiomeric excess. Under <strong>the</strong>se conditions, only 0.05 mol% of <strong>the</strong><br />

catalyst <strong>for</strong>ced <strong>the</strong> reaction to completion in 48 h. The work-up procedure was also improved and <strong>the</strong><br />

enantiomerically pure compound was obtained as a white crystal in up to 95% yield without<br />

chromatographic separation. Finally, pre-manufacturing scale syn<strong>the</strong>sis was per<strong>for</strong>med. Using 0.1<br />

mol% of <strong>the</strong> catalyst with 0.09 mol% of KO-t-Bu and MS 4 Angstrom, <strong>the</strong> Michael reaction of 2-<br />

cyclohexenone (6.0 mol, 581 mL) with dimethyl malonate (6.0 mol, 686 mL) was completed in 24 h<br />

at ambient temperature to af<strong>for</strong>d more than a kilogram of <strong>the</strong> enantiomerically pure product in 91%<br />

yield after three successive crystallizations. The described method renders <strong>the</strong> enantiomerically pure<br />

Michael adduct readily available on greater than kilo scale. (C) 2002 Elsevier Science Ltd. All rights<br />

r e s e r v e d .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Zhao, S., X. B. Liao and J. M. Cook<br />

Enantiospecific, stereospecific total syn<strong>the</strong>sis of (+)-majvinine, (+)-10-methoxyaff<br />

2002<br />

Organic Letters<br />

4(5): 687-690<br />

Abstract<br />

[GRAPHICS] - The enantiospecific stereospecific total syn<strong>the</strong>sis of majvinine la, 10-<br />

methoxyaffinisine 1b, and N-a-methylsarpagine 1c are reported; this method has also resulted in <strong>the</strong><br />

total syn<strong>the</strong>sis of <strong>the</strong> Alstonia bisindole macralstonidine 2.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Biswas, S., T. Murugesan, K. Maiti, L. Ghosh, M. Pal and B. P. Saha<br />

Study on <strong>the</strong> diuretic activity of <strong>Strychnos</strong> potatorum linn. Seed extract in albino r<br />

2001<br />

Phytomedicine<br />

8(6): 469-471<br />

Abstract<br />

Methanol extract of <strong>Strychnos</strong> potatorum Linn. seeds (SPSE) was evaluated <strong>for</strong> its diuretic activity<br />

in Wistar albino rats. The SPSE was administered at <strong>the</strong> graded doses of 200, 400, and 600 mg/kg<br />

body weight. The parameters which were taken into account during <strong>the</strong> experimental on each rat<br />

were: total urine volume (corrected <strong>for</strong> water intake during <strong>the</strong> test period), body weight be<strong>for</strong>e and<br />

after <strong>the</strong> experiment, and <strong>the</strong> concentration of sodium, potassium, and chloride ions in urine. The<br />

total urine volumes of <strong>the</strong> SPSE (600 mg/kg)-treated rats were evaluated nearly two and half fold<br />

<strong>the</strong>n compared with <strong>the</strong> control (saline treated) group. Excretion of cations (sodium and potassium<br />

ions) and anions (chloride ions) also increased significantly with respect to <strong>the</strong> control group. The<br />

diuretic effect was comparable with that of <strong>the</strong> standard drug Furosemide. The increase of cations in<br />

<strong>the</strong> urine on treatment with <strong>Strychnos</strong> potatorum seed extract (SPSE) was dose-dependent. This<br />

effect supports <strong>the</strong> use of <strong>the</strong> <strong>Strychnos</strong> potatorum seeds as a diuretic in folk remedies.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Brandt, V., M. Tits, J. Penelle, M. Frederich and L. Angenot<br />

Main glucosidase conversion products of <strong>the</strong> gluco-alkaloids dolichantoside and p<br />

2001<br />

Phytochemistry<br />

57(5): 653-659<br />

Abstract<br />

The enzymatic glucose cleavage of palicoside revealed <strong>the</strong> biosyn<strong>the</strong>tic pathway to akagerine,<br />

whereas <strong>the</strong> conversion of dolichantoside led to a new quaternary heteroyohimbine alkaloid named<br />

N-b-methyl-21-beta -hydroxy-mayumbine. The hypo<strong>the</strong>tical models of reactions occurring after <strong>the</strong><br />

conversion of both substrates are proposed. Dolichantoside and palicoside, as well as <strong>Strychnos</strong><br />

mellodora a stem bark crude ethanol extract, exhibit significant antimycotic activity against human<br />

pathogens in presence of specific glucosidase. (C) 2001 Elsevier Science Ltd. All rights reserved.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Cheng, M. J., I. L. Tsai and I. S. Chen<br />

Chemical constituents from <strong>Strychnos</strong> cathayensis<br />

2001<br />

Journal of <strong>the</strong> Chinese Chemical Society Taipei<br />

48(2): 235-240<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Frederich, M., M. C. De Pauw, C. Prosperi, M. Tits, V. Brandt, J. Penelle, M. P.<br />

Strychnogucines a' and b, two new antiplasmodial bisindole alkaloids from Strych<br />

2001<br />

Journal of Natural Products<br />

64(1): 12-16<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Frederich, M., M. P. Hayette, M. Tits, P. De Mol and L. Angenot<br />

Reversal of chloroquine and mefloquine resistance in Plasmodium falciparum by t<br />

2001<br />

Planta Medica<br />

67(6): 523-527<br />

Abstract<br />

Eight naturally occurring monoindole alkaloids were evaluated in vitro <strong>for</strong> <strong>the</strong>ir ability to inhibit<br />

Plasmodium falciparum growth and, in drug combination, to reverse <strong>the</strong> resistance of a chloroquineresistant<br />

strain of Plasmodium falciparum. None of <strong>the</strong>se indole alkaloids has significant intrinsic<br />

antiplasmodial activity (IC50 > 10 muM or 5 mug/ml). Never<strong>the</strong>less, three alkaloids (icajine,<br />

isoretuline and strychnobrasiline) did reverse chloroquine resistance at concentrations between 2.5<br />

and 25.4 g/ml (IF of 12.82 <strong>for</strong> isoretuline on W2 strain). The Interaction Factor (IF) equals 2, < 2, or<br />

> 2 <strong>for</strong> additive, antagonistic or synergistic effects of alkaloids on chloroquine inhibition,<br />

respectively. Icajine and isoretuline were also assessed in vitro <strong>for</strong> <strong>the</strong>ir mefloquine potentiating<br />

activity on a mefloquine-resistant strain of Plasmodium falciparum. Only icajine proved to be<br />

s y n e r g i s t i c w i t h m e f l o q u i n e ( I F = 1 5 . 3 8 ) .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Hilton, S. T., T. C. T. Ho, G. Pljevaljcic, M. Schulte and K. Jones<br />

A tandem radical approach to <strong>the</strong> abce-rings of <strong>the</strong> aspidosperma and strychnos al<br />

2001<br />

Chemical Communications- Royal Society of Chemistry<br />

(2): 209-210<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Ito, M., C. W. Clark, M. Mortimore, J. B. Goh and S. F. Martin<br />

Biogenetically inspired approach to <strong>the</strong> strychnos alkaloids. Concise syn<strong>the</strong>ses of<br />

2001<br />

Journal of <strong>the</strong> American Chemical Society<br />

123(33): 8003-8010<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Lambert, J. E.<br />

Red-tailed guenons (Cercopi<strong>the</strong>cus ascanius) and <strong>Strychnos</strong> mitis: Evidence <strong>for</strong> pl<br />

2001<br />

International Journal of Primatology<br />

22(2): 189-202<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Mori, M., M. Nakanishi, D. Kajishima and Y. Sato<br />

A new and general syn<strong>the</strong>tic pathway to strychnos indole alkaloids: Total syn<strong>the</strong>s<br />

2001<br />

Organic Letters<br />

3(12): 1913-1916<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Oppelt AL; Kurth W; Godbold DL<br />

Topology, scaling relations and leonardo's rule in root systems from African tree s<br />

2001<br />

Tree Physiology<br />

21(2-3): 117-128<br />

Abstract<br />

Aspects of root architecture, including topology, link length, diameter and scaling relations, were<br />

analyzed in excavated coarse root systems of three field-grown fruit tree species (<strong>Strychnos</strong><br />

cocculoides Bak., <strong>Strychnos</strong> spinosa Lam. And Vangueria infausta Burch) and <strong>the</strong> fruit-bearing<br />

shrub Grewia flava DC. We investigated <strong>the</strong> root systems using semi-automatic digitizing and<br />

computer-based 3-D reconstruction techniques. Topological analysis was carried out to investigate<br />

branching patterns as basic determinants of root architecture. New topological indices were<br />

developed and revealed significant differences among <strong>the</strong> species. The different architectural<br />

strategies can be explained in terms of cost-benefit relations and efficiency in soil resource<br />

exploration and exploitation. In addition, some well-known hypo<strong>the</strong>ses about geometry and scaling,<br />

most of <strong>the</strong>m previously unverified by empirical observations on root systems, were tested. For<br />

practical applications, <strong>the</strong> main emphasis is on <strong>the</strong> relationship between proximal root diameter, an<br />

easily determined parameter, and several parameters describing <strong>the</strong> size of <strong>the</strong> whole root system.<br />

We also tested <strong>the</strong> "pipe stem" <strong>the</strong>ory, essentially dating back to Leonardo da Vinci, which underlies<br />

many models and which we found con<strong>for</strong>med to our measurement data with reasonable accuracy. A<br />

physiological consequence of <strong>the</strong> "constant cross-sectional area rule" may be a certain homogeneity<br />

of hydraulic architecture throughout root systems.<br />

O<strong>the</strong>r species included: Grewia flava; <strong>Strychnos</strong> spinosa; Vangueria infausta.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Penelle, J., P. Christen, J. Molgo, M. Tits, V. Brandt, M. Frederich and L. Angeno<br />

5 ',6 '-dehydroguiachrysine and 5 ',6 '-dehydroguiaflavine, two curarizing quaterna<br />

2001<br />

Phytochemistry<br />

58(4): 619-626<br />

Abstract<br />

Two new quaternary indole alkaloids 5',6'-dehydroguiachrysine (1) and 5',6'-dehydroguiaflavine (2)<br />

were isolated from <strong>Strychnos</strong> guianensis stem bark. Their structures were determined by analysis of<br />

spectral data. Their inhibitory effects on neuromuscular transmission are also reported and compared<br />

to that of o<strong>the</strong>r quaternary alkaloids. © 2001 Elsevier Science Ltd. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rasoanaivo, P., G. Palazzino, M. Nicoletti and C. Galeffi<br />

The co-occurrence of c(3) epimer n-b,c(21)-secocuran alkaloids in <strong>Strychnos</strong> dipl<br />

2001<br />

Phytochemistry<br />

56(8): 863-867<br />

Abstract<br />

From <strong>the</strong> stem bark of <strong>Strychnos</strong> diplotricha, three N-b,C(21)-secocuran alkaloids, viz., 3-epimyrtoidine,<br />

11- demethoxy-3-epi-myrtoidine and 11-demethoxy-12-hydroxy-3-epi-myrtoidine, were<br />

isolated toge<strong>the</strong>r with <strong>the</strong> known myrtoidine and 11-demethoxymyrtoidine. They also occur in<br />

different parts of S. myrtoides. (C) 2001 Elsevier Science Ltd. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Shoba, F. G. and M. Thomas<br />

Study of antidiarrhoeal activity of four medicinal plants in castor-oil induced diarr<br />

2001<br />

Journal of Ethnopharmacology<br />

76(1): 73-76<br />

Abstract<br />

A study was undertaken to evaluate <strong>the</strong> effect of aqueous and methanolic plant extracts of Acorus<br />

calamus rhizome, Pongamia glabra leaves, Aegle marmelos unripe fruit and <strong>Strychnos</strong> nux-vomica<br />

root bark <strong>for</strong> <strong>the</strong>ir antidiarrhoeal potential against castor-oil induced diarrhoea in mice. The<br />

methanolic plant extracts were more effective than aqueous plant extracts against castor-oil induced<br />

diarrhoea. The methanolic plant extracts significantly reduced induction lime of diarrhoea and total<br />

weight of <strong>the</strong> faeces. The result obtained establish <strong>the</strong> efficacy of <strong>the</strong>se plant extracts as<br />

antidiarrhoeal agents. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Sukul, N. C., S. Ghosh, S. P. Sinhababu and A. Sukul<br />

<strong>Strychnos</strong> nux vomica extract and its ultra-high dilution reduce voluntary ethanol i<br />

2001<br />

Journal of Alternative and Complementary Medicine<br />

7(2): 187-194<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Yashodhara, V. and K. Subhash<br />

Somatic embryogenesis in <strong>Strychnos</strong> nux vomica L<br />

2001<br />

Advances in Plant Sciences<br />

14(2): 491-494<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Backlund, M., B. Oxelman and B. Bremer<br />

Phylogenetic relationships within <strong>the</strong> Gentianales based on ndhf and rbcl sequenc<br />

2000<br />

American Journal of Botany<br />

87(7): 1029-1043<br />

Abstract<br />

Phylogenetic relationships in <strong>the</strong> Gentianales with focus on Loganiaceae sensu late are evaluated<br />

using parsimony analyses of nucleotide sequence data from <strong>the</strong> plastid genes rbcL and ndhF. Interand<br />

intrafamilial relationships in <strong>the</strong> Gentianales. which consist of <strong>the</strong> families Apocynaceae<br />

(including Asclepiadaceae), Gelsemiaceae, Gentianaceae, Loganiaceae, and Rubiaceae, are studied<br />

and receive increased support from <strong>the</strong> combination of rbcL and ndhF data, which indicate that <strong>the</strong><br />

Family Rubiaceae <strong>for</strong>ms <strong>the</strong> sister group to <strong>the</strong> successively nested Gentianaceae, Apocynaceae, and<br />

Loganiaceae, all of which are well supported. The family Gelsemiaceae <strong>for</strong>ms a distinct, supported<br />

group sister to Apocynaceae. The Loganiaceae sensu stricto <strong>for</strong>m a strongly supported group<br />

consisting of 13 genera: Antonia, Bonyunia, Gardneria, Geniostoma, Labordia. Logania,<br />

Mituasacme, Mirreola, Neuburgia, Norrisia, Spigelia, <strong>Strychnos</strong>, and Usteria. These genera <strong>for</strong>m<br />

two well-supported lineages. Several members of Loganiaceae sensu Leeuwenberg and Leenhouts,<br />

i.e., Androya, Peltan<strong>the</strong>ra, Plocosperma, Polypremum, and Sanango are clearly not members of <strong>the</strong><br />

Gentianales. The earlier exclusion of Buddlejaceae (including Buddleja, Emorya, Gomphostigma,<br />

and Nicodemia) as well as <strong>the</strong> reclassification of <strong>the</strong> genera Nuxia and Retzia to Stilbaceae of <strong>the</strong><br />

L a m i a l e s a r e a l l w e l l s u p p o r t e d .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Baimai, V., J. Phinchongsakuldit and C. Sumrandee<br />

Cytological evidence <strong>for</strong> a complex of species within <strong>the</strong> taxon Bactrocera tau (Di<br />

2000<br />

Biological Journal of <strong>the</strong> Linnean Society<br />

69(3): 399-409<br />

Abstract<br />

Analysis of mitotic karyotypes of wild specimens of larvae of <strong>the</strong> Bactrocera tau-like fruit flies<br />

(Diptera: Tephritidae) in Thailand has revealed seven distinct chromosome <strong>for</strong>ms, based on <strong>the</strong><br />

amount and distribution of heterochromatin in sex chromosomes and autosomes. Such cytological<br />

differences are perfectly correlated with morphological observations and molecular genetics data.<br />

These findings clearly suggest that B. tau is a cluster of at least seven closely related species<br />

temporarily designated as species A (=B. tau), B, C, D, E, F and G. On <strong>the</strong> basis of <strong>the</strong> gross<br />

quantity of heterochromatin accumulation in <strong>the</strong> genome, three groups of mitotic karyotypes can be<br />

recognized. Group 1 comprises species A and E. Species E specifically occurs only in fruits of<br />

<strong>Strychnos</strong> thorelii while species A attacks many kinds of host plants. Group 2 contains species B, F<br />

and G. Species B has been found only in Siphonodon celastrineus fruit, whereas species F and G<br />

attack <strong>the</strong> same host species, <strong>the</strong> medically important plant, Hydnocarpus an<strong>the</strong>lminthicus, albeit in<br />

different localities. Group 3 includes species C and D, each of which comprises larger amounts of<br />

pericentric heterochromatin in all chromosomes than <strong>the</strong> o<strong>the</strong>r two groups. Hence, <strong>the</strong>se two species<br />

are cytologically remote from those of groups 1 and 2. Species C and D occur allopatrically but <strong>the</strong>y<br />

attack <strong>the</strong> same host plant species, Momordica cochinchinensis. Thus, genetic differentiation at <strong>the</strong><br />

chromosomal level to specific host plant species and geographic isolation seem to play an important<br />

role in speciation of members of <strong>the</strong> B, tau complex. (C) 2000 The Linnean Society of London.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonifacio, E. a., S. Santonoi and E. Zanini<br />

Soil properties required by some sou<strong>the</strong>rn Sfrica fruit trees as assessed by discrimi<br />

2000<br />

Arid Soil Research and Rehabilitation<br />

14(3): 253-263<br />

Abstract<br />

Some indigenous fruit trees, in <strong>the</strong> drylands of sou<strong>the</strong>rn Africa are worthy of interest because of<br />

<strong>the</strong>ir adaptation to environmental conditions prohibitive <strong>for</strong> traditional crops. Their fruits or <strong>the</strong>ir<br />

derivatives are traditionally used as an additional income by rural population, but little in<strong>for</strong>mation<br />

is available about <strong>the</strong> properties of <strong>the</strong> soils that support <strong>the</strong>ir growth, although this in<strong>for</strong>mation is<br />

necessary if <strong>the</strong> trees are subjected to sustainable domestication. Several soil properties are,<br />

however, to be considered as a whole and discriminant analysis provides a helpful tool to individuate<br />

<strong>the</strong> best conditions <strong>for</strong> <strong>the</strong> tree growth. Thirty-five soil samples were taken in areas where <strong>the</strong> trees<br />

naturally grow and produce, and <strong>the</strong> analytical data of <strong>the</strong> surface layer were used to relate soil<br />

properties to tree species. Four groups of trees were well separated using two discriminant functions<br />

that takes into account both <strong>the</strong> fertility characteristics (pH, organic C, N, texture, and properties of<br />

<strong>the</strong> exchange complex) and <strong>the</strong> Fe contents and distribution among <strong>the</strong> oxide <strong>for</strong>ms. The<br />

discriminant functions allow a very acceptable reclassification of <strong>the</strong> data (more than 80% of cases<br />

correctly reclassified) and <strong>the</strong> classification coefficients were used to build an empirical equation<br />

that may help to identify <strong>the</strong> most suitable tree to be introduced at a new site.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Brandt, V., A. Geerlings, M. Tits, C. Delaude, R. van der Heijden, R. Verpoorte a<br />

New strictosidine beta-glucosidase from <strong>Strychnos</strong> mellodora<br />

2000<br />

Plant Physiology and Biochemistry<br />

38(3): 187-192<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Chen, W. S., L. L. Liu, X. Li, L. W. Li, S. G. Ji, G. Q. Zhang and Y. F. Chai<br />

Separation and determination of strychnine and brucine in <strong>Strychnos</strong> nux vomica<br />

2000<br />

Biomedical Chromatography<br />

14(8): 541-543<br />

Abstract<br />

A capillary zone electrophoresis method was developed <strong>for</strong> <strong>the</strong> separation and determination of<br />

strychnine and brucine in <strong>Strychnos</strong> nux-vomica L. and its preparation. The factors that could affect<br />

<strong>the</strong> separation were studied, such as <strong>the</strong> types and concentrations of electrolytes, pH, ionic strength<br />

and organic modifier. The optimum running buffer was 20 mmol/L of ammonium acetate containing<br />

0.2 mol/L of glacial acetic acid (pH 3.64). The applied voltage was 25 kV and <strong>the</strong> wavelength of <strong>the</strong><br />

UV detector was set at 214 nm. The established method with dopamine hydrochloride as internal<br />

standard was linear in <strong>the</strong> range of 5-100 mug/mL <strong>for</strong> both strychnine and brucine. The recovery was<br />

102.96% <strong>for</strong> strychnine and 98.56% <strong>for</strong> brucine. The extracts of <strong>Strychnos</strong> nux-vomica and its<br />

preparation could be directly injected <strong>for</strong> analysis. Copyright (C) 2000 John Wiley & Sons, Ltd.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ergun, Y., N. Bayraktar, S. Patir and G. Okay<br />

Intermediates <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of indole alkaloids. Syn<strong>the</strong>sis of tetrahydrocarbazo<br />

2000<br />

Journal of Heterocyclic Chemistry<br />

37(1): 11-14<br />

Abstract<br />

The syn<strong>the</strong>sis of new precursors 8 and 15 <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of tetracyclic indole alkaloids were<br />

described. Many new intermediates 4-7 and 9-14 have also been syn<strong>the</strong>sized.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Frederich, M., M. C. De Pauw, G. Liabres, M. Tits, M. P. Hayette, V. Brandt, J. P<br />

New antimalarial and cytotoxic sungucine derivatives from <strong>Strychnos</strong> icaja roots<br />

2000<br />

Planta Medica<br />

66(3): 262-269<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Liu XX; Wang T; Xu QG; Ma CR; Cook JM<br />

Enantiospecific total syn<strong>the</strong>sis of <strong>the</strong> enantiomer of <strong>the</strong> indole alkaloid affinisine<br />

2000<br />

Tetrahedron Letters<br />

41(33): 6299-6303<br />

Abstract<br />

The enantiomer of affinisine has been syn<strong>the</strong>sized (from L-tryptophan) with 100%<br />

diastereoselectivity via <strong>the</strong> asymmetric Pictet-Spengler reaction coupled with a Pd-0 (enolate<br />

mediated) coupling process. This enantiomer has also been converted into a key intermediate which<br />

provides a route to <strong>the</strong> enantiomers of both macroline and alstonerine following <strong>the</strong> previous work of<br />

LeQuesne. (C) 2000 Elsevier Science Ltd. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Lockett, C. T. and L. E. Grivetti<br />

Food-related behaviors during drought: A study of rural Fulani, nor<strong>the</strong>astern Nige<br />

2000<br />

International Journal of Food Sciences and Nutrition<br />

51(2): 91-107<br />

Abstract<br />

Two rural settled Fulani villages in nor<strong>the</strong>ast Nigeria were surveyed <strong>for</strong> dietary practices and use of<br />

edible wild plants (n = 100 adult subjects). Dietary patterns and medical data were obtained <strong>for</strong><br />

children under 5, pregnant and lactating women and <strong>the</strong> elderly. A diversified diet was maintained at<br />

both geographical locations through hunting, ga<strong>the</strong>ring, agriculture, horticulture, animal husbandry,<br />

food exchanges and cash purchases. Edible wild plants associated with children included fruits of<br />

baure (Ficus sycomorus), faru (Lannea schiniperi), giginya (Gardenia aqualla), kokiya (<strong>Strychnos</strong><br />

spinosa) and nunu (Parinari curatellitolia). Leaves of shiwaka (Veronia colorate) were consumed by<br />

lactating women to stimulate breastmilk production. Generally, fruits of baure (Ficus sycomorus)<br />

were eaten to counter stomach pain; fruits of kisni (Bridelia ferruginea) were eaten to treat diarrhea;<br />

and bark of kuka (Adansonia digitata) was consumed <strong>for</strong> weight gain. Food storage was more<br />

important during wet seasons than dry because of local and regional flooding. Adult Fulani men rode<br />

to distant markets on bicycles, while women walked to market and in some instances expended 3200<br />

k c a l / d a y e n g a g i n g i n t h i s a c t i v i t y .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Morah, F. N. I.<br />

Fruit terpenoids and fatty acids of <strong>Strychnos</strong> spinosa Lam<br />

2000<br />

Global Journal of Pure and Applied Sciences<br />

6(1): 57-60<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Ohba, M., H. Kubo and H. Ishibashi<br />

A chiral syn<strong>the</strong>sis of <strong>the</strong> <strong>Strychnos</strong> and ophiorrhiza alkaloid normalindine<br />

2000<br />

Tetrahedron<br />

56(39): 7751-7761<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ohori, K., S. Shimizu, T. Ohshima and M. Shibasaki<br />

Catalytic asymmetric syn<strong>the</strong>sis of 19,20-dihydroakuammicine<br />

2000<br />

Chirality<br />

12(5-6): 400-403<br />

Abstract<br />

An enantiocontrolled total syn<strong>the</strong>sis of 19,20-dihydroaltuammicine using a catalytic asymmetric<br />

Michael addition of dimethyl malonate to cyclohexenone as <strong>the</strong> key step is described. The above<br />

catalytic asymmetric Michael addition proceeds quite efficiently in <strong>the</strong> presence of a heterobimetalic<br />

asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving <strong>the</strong> corresponding Michael adduct in<br />

94% yield and 99% ee. (C) 2000 Wiley Liss,Inc.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Ohshima, T., X. Youjun, Y. S. Kim, S. Matsunaga, K. Ohori and M. Shibasaki<br />

Studies toward <strong>the</strong> asymmetric total syn<strong>the</strong>sis of strychnos alkaloid (-)-strychnine<br />

2000<br />

Symposium on <strong>the</strong> Chemistry of Natural Products<br />

42: 145-150<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Oliveira AFM; Salatino A<br />

Major constituents of <strong>the</strong> foliar epicuticular waxes of species from <strong>the</strong> Caatinga a<br />

2000<br />

Zeitschrift Fur Natur<strong>for</strong>schung C-a Journal of Biosciences<br />

55(9-10): 688-692<br />

Abstract<br />

The epicuticular waxes of leaves of four species (Aspidosperma pyrifolium, Capparis yco, Maytenus<br />

rigida and Ziziphus joazeiro) from <strong>the</strong> Caatinga, (a semi-arid ecosystem of Nor<strong>the</strong>ast Brazil) and<br />

four species (Aristolochia esperanzae, Didymopanax vinosum, <strong>Strychnos</strong> pseudoquina and Tocoyena<br />

<strong>for</strong>mosa) from <strong>the</strong> Cerrado, (a savanna ecosystem covering one third of <strong>the</strong> Brazilian territory), were<br />

analyzed. Six species contained a high content (above 60 mug.cm(-2)) of wax, four of <strong>the</strong>m from <strong>the</strong><br />

Caatinga. Triterpenoids and n-alkanes were <strong>the</strong> most frequent and abundant constituents found in <strong>the</strong><br />

species from both habitats. The distribution of n-alkanes predominated by homologues with 27, 29,<br />

31 and 33 carbon atoms, displayed no consistent differences between species from <strong>the</strong> two habitats.<br />

Lupeol, beta -amyrin, epifriedelinol and ursolic acid were <strong>the</strong> triterpenoids found. Triterpenoids<br />

clearly predominate over alkanes in <strong>the</strong> waxes from <strong>the</strong> Cerrado species. The waxes of two<br />

evergreen species from <strong>the</strong> Caatinga yielded n-alkanes as predominant constituents. A comparison of<br />

foliar epicuticular waxes of native plants from ecosystems with different hydric constraints is<br />

d i s c u s s e d .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Oppelt, A. L. a., W. Kurth, H. Dzierzon, G. Jentschke and D. L. Godbold<br />

Structure and fractal dimensions of root systems of four co-occurring fruit tree spe<br />

2000<br />

Annals of Forest Science<br />

57(5-6): 463-475<br />

Abstract<br />

Coarse root systems of four different fruit tree species from sou<strong>the</strong>rn Africa were completely<br />

excavated and semi-automatically digitized. Spatial distributions of root length were determined<br />

from <strong>the</strong> digitally-reconstructed branching systems. Fur<strong>the</strong>rmore, <strong>the</strong> fractal characteristic of <strong>the</strong><br />

coarse root systems was shown by determining <strong>the</strong> box-counting dimensions. These quantitative<br />

methods revealed architectural differences between <strong>the</strong> species, probably due to different<br />

ecophysiological strategies. For fine root samples, which were taken be<strong>for</strong>e digging out <strong>the</strong> whole<br />

systems, fractal analysis of <strong>the</strong> planar projections showed no significant inter-species differences.<br />

Methodologically, <strong>the</strong> study underlines <strong>the</strong> usefulness of digital 3-D reconstruction in root research.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Otero, R., V. Nunez, J. Barona, R. Fonnegra, S. L. Jimenez, R. G. Osorio, M. Sald<br />

Snakebites and ethnobotany in <strong>the</strong> northwest region of colombia part iii: Neutraliz<br />

2000<br />

Journal of Ethnopharmacology<br />

73(1-2): 233-241<br />

Abstract<br />

Thirty-one of 75 extracts of plants used by traditional healers <strong>for</strong> snakebites, had moderate or high<br />

neutralizing ability against <strong>the</strong> haemorrhagic effect of Bothrops atrox venom from Antioquia and<br />

Choco, north-western Colombia. After preincubation of several doses of every extract (7.8-4000<br />

mug/mouse) with six minimum haemorrhagic doses (10 mug) of venom, 12 of <strong>the</strong>m demonstrated<br />

100% neutralizing capacity when <strong>the</strong> mixture was i.d. injected into mice (18-20 g). These were <strong>the</strong><br />

stem barks of Brownea rosademonte (Caesalpiniaceae) and Tabebuia rosea (Bignoniaceae); <strong>the</strong><br />

whole plants of Pleopeltis percussa (Polypodiaceae), Trichomanes elegans (Hymenophyllaceae) and<br />

Senna dariensis (Caesalpiniaceae); rhizomes of Heliconia curtispatha (Heliconiaceae); leaves and<br />

branches of Bixa orellana (Bixaceae), Philodendron tripartitum (Araceae), Struthanthus orbicularis<br />

(Loranthaceae) and Gonzalagunia panamensis (Rubiaceae); <strong>the</strong> ripe fruits of Citrus limon<br />

(Rutaceae); leaves, branches and stem of Ficus nymphaeifolia (Moraceae). Extracts of ano<strong>the</strong>r 19<br />

species showed moderate neutralization (21-72%) at doses up to 4 mg/mouse, e.g. <strong>the</strong> whole plants<br />

of Aristolochia grandiflora (Aristolochiaceae), Columnea kalbreyeriana (Gesneriaceae), Sida acuta<br />

(Malvaceae), Selaginella articulata (Selaginellaceae) and Pseudoelephantopus spicatus (Asteraceae);<br />

rhizomes:of Renealmia alpinia (Zingiberaceae); <strong>the</strong> stem of <strong>Strychnos</strong> xinguensis (Loganiaceae);<br />

leaves, branches and stems of Hyptis capitata (Lamiaceae), Ipomoea cailica (Convolvulaceae),<br />

Neurolaena lobata (Asteraceae), Ocimum micranthum (Lamiaceae), Piper pulchrum (Piperaceae),<br />

Siparuna <strong>the</strong>caphora (Monimiaceae), Castilla elastica (Moraceae) and Allamanda cathartica<br />

(Apocynaceae); <strong>the</strong> macerated ripe fruits of Capsicum frutescens (Solanaceae); <strong>the</strong> unripe fruits of<br />

Crescentia cujete (Bignoniaceae); leaves and branches of Piper arboreum (Piperaceae) and Passiflora<br />

quadrangular is (Passifloraceae). When <strong>the</strong> extracts were independently administered by oral, i.p, or<br />

i.v. route ei<strong>the</strong>r be<strong>for</strong>e or after an i.d. venom injection (10 mug), neutralization of haemorrhage<br />

dropped below 25% <strong>for</strong> all <strong>the</strong> extracts. Additionally, B. rosademonte and P. percussa extracts were<br />

able to inhibit <strong>the</strong> proteolytic activity of B. atrox venom on casein. (C) 2000 Elsevier Science Ireland<br />

L t d . A l l r i g h t s r e s e r v e d .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Padwa, A. and A. G. Waterson<br />

The thionium/n-acyliminium ion cyclization cascade as a strategy <strong>for</strong> <strong>the</strong> syn<strong>the</strong>si<br />

2000<br />

Tetrahedron<br />

56(52): 10159-10173<br />

Abstract<br />

A series of amidosulfoxides were prepared by <strong>the</strong> addition of thiophenol to <strong>the</strong> appropriate alkenoic<br />

acid pi -bond, and this was followed by reaction of <strong>the</strong> in situ generated acyl chloride with 3,4-<br />

dimethoxyphenethyl amine. The silicon-induced Pummerer reaction of <strong>the</strong>se amidosulfoxides was<br />

carried out using 1-(dimethyl-tert-butylsiloxy)-1-methoxyethylene in dry acetonitrile in <strong>the</strong> presence<br />

of a catalytic amount of ZnI2 and led to <strong>the</strong> very clean <strong>for</strong>mation of 2-thiophenyl substituted lactams.<br />

Iminium ion-aromatic pi -cyclization was accomplished by treatment of <strong>the</strong> initially <strong>for</strong>med<br />

thiophenyl lactams with BF3.2AcOH which resulted in <strong>the</strong> generation of an N-acyliminium ion.<br />

Cyclization of <strong>the</strong> iminium ion onto <strong>the</strong> te<strong>the</strong>red aromatic ring led to various azapolycyclic ring<br />

systems. A related cyclization sequence also occurred with amidosulfoxides that possess simple<br />

olefinic te<strong>the</strong>rs. The method was applied toward <strong>the</strong> syn<strong>the</strong>sis of a member of <strong>the</strong> protoberberine<br />

alkaloid family. (C) 2000 Elsevier Science Ltd. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Penelle, J., M. Tits, P. Christen, J. Molgo, V. Brandt, M. Frederich and L. Angeno<br />

Quaternary indole alkaloids from <strong>the</strong> stem bark of <strong>Strychnos</strong> guianensis<br />

2000<br />

Phytochemistry<br />

53(8): 1057-1066<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rafatro, H., D. Ramanitrahasimbola, P. Rasoanaivo, S. Ratsimamanga-Urverg, A.<br />

Reversal activity of <strong>the</strong> naturally occurring chemosensitizer malagashanine in Plas<br />

2000<br />

Biochemical Pharmacology<br />

59(9): 1053-1061<br />

Abstract<br />

Malagashanine (MG) is <strong>the</strong> parent compound of a new type of indole alkaloids, <strong>the</strong> NbC(21)-<br />

secocuran, isolated so far from <strong>the</strong> Malagasy <strong>Strychnos</strong> species traditionally used as chloroquine<br />

adjuvants in <strong>the</strong> treatment of chronic malaria. Previously, it was shown to have weak in vitro<br />

intrinsic antiplasmodial activity (IC50 = 146.5 +/- 0.2 mu M), but did display marked in vitro<br />

chloroquine-potentiating action against <strong>the</strong> FcM29 chloroquine-resistant strain of Plasmodium<br />

falciparum. The purpose of <strong>the</strong> present study was to fur<strong>the</strong>r investigate its reversal activity. Thus, <strong>the</strong><br />

previous in vitro results were tested in vivo. The interaction of MG with several antimalarials against<br />

various strains of P. falciparum was also assessed. As expected, MG enhanced <strong>the</strong> effect of<br />

chloroquine against <strong>the</strong> resistant strain W2, but had no action on <strong>the</strong> susceptible strain 3D7 and two<br />

sensitive isolates. interestingly, MG was found to exhibit significant chloroquine-potentiating action<br />

against <strong>the</strong> FcB1 strain <strong>for</strong>merly described as a resistant strain but one which has since lost its<br />

resistance <strong>for</strong> unknown reasons. One o<strong>the</strong>r relevant result that arose from our study was <strong>the</strong><br />

observation of <strong>the</strong> selective enhancing action of MG on quinolines (chloroquine, quinine, and<br />

mefloquine), aminoacridines (quinacrine and pyronaridine), and a structurally unrelated drug<br />

(halofantrine), all of which are believed to exert <strong>the</strong>ir antimalarial effect by binding with haematin.<br />

MG was finally found to specifically act with chloroquine on <strong>the</strong> old trophozoite stage of <strong>the</strong> P.<br />

falciparum cycle. Similarities and differences between verapamil and MG reversal activity are<br />

b riefly presented. (C) 2000 Elsevier Science Inc.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rafatro, H., R. K. Verbeeck, T. Y. R. Gougnard, P. J. M. De Jonghe, P. Rasoanaiv<br />

Isolation from rat urine and human liver microsomes and identification by electros<br />

2000<br />

Journal of Mass Spectrometry<br />

35(9) : 1112-1120<br />

Abstract<br />

Malagashanine has been isolated from indigenous madagasean <strong>Strychnos</strong> myrtoides alkaloids used<br />

traditionally to treat malaria, This alkaloid was found to enhance <strong>the</strong> action of chloroquine against<br />

chloroquine-resistant strains of Plasmodium falciparum when combined with classical antimalarial<br />

drugs (chloroquine, quinine), The present study was carried out in order to investigate by<br />

electrospray mass and tandem mass spectrometry and NMR spectroscopy <strong>the</strong> structure of two new<br />

metabolites isolated from rat urine and human liver microsomes, We were able to demonstrate <strong>the</strong><br />

presence of two new metabolites of malagashanine corresponding to a malagashanine N-<br />

demethylated metabolite and to <strong>the</strong> oxidation of malagashanine in <strong>the</strong> alpha-position of <strong>the</strong> N-methyl<br />

group to produce a carbinolamine function. The latter metabolite may be subject to ring and openchain<br />

tautomerism effects and dimeric species were detected in <strong>the</strong> electrospray mass spectrum.<br />

C o p y r i g h t ( C ) 2 0 0 0 J o h n W i l e y & S o n s , L t d .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rukuni D<br />

Analysis of fruit traits of <strong>Strychnos</strong> cocculoides: An important indigenous fruit tre<br />

2000<br />

Tree Seed News<br />

2: 5-7<br />

Abstract<br />

An analysis is presented of fruit traits of <strong>Strychnos</strong> cocculoides collected from 18 provenances in<br />

Zimbabwe. The fruits were characterized <strong>for</strong> fruit weight and diameter, weight of edible pulp, total<br />

weight of seed, weight and thickness of shell, number of seeds per fruit, <strong>the</strong> percent total soluble<br />

solids or brix, and 1000-seed weight. The ratio of <strong>the</strong> edible part of <strong>the</strong> fruit was also determined<br />

based on measurements of <strong>the</strong> weight of internal fruit contents and total seed weight.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Sierra, M. A. and M. C. de la Torre<br />

Dead ends and detours en route to total syn<strong>the</strong>ses of <strong>the</strong> <strong>1990</strong>s<br />

2000<br />

Angewandte Chemie-International Edition<br />

39(9): 1538-1559<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Sole, D., E. Peidro and J. Bonjoch<br />

Palladium-catalyzed intramolecular coupling of vinyl halides and ketone enolates,<br />

2000<br />

Organic Letters<br />

2(15): 2225-2228<br />

Abstract<br />

[GRAPHICS] - The palladium-mediated intramolecular coupling of amino-te<strong>the</strong>red vinyl halides and<br />

ketone enolates is a useful methodology <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of nitrogen heterocycles and constitutes a<br />

new syn<strong>the</strong>tic entry to <strong>the</strong> 2-azabicyclo[3.3.1]nonane framework, A study about <strong>the</strong> reaction<br />

conditions and <strong>the</strong> scope of <strong>the</strong> process is reported.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Sole, D., J. Bonjoch, S. Garcia-Rubio, E. Peidro and J. Bosch<br />

Enantioselective total syn<strong>the</strong>sis of wieland-gumlich aldehyde and (-)-strychnine<br />

2000<br />

Chemistry- A European Journal<br />

6(4): 655-665<br />

Abstract<br />

A total syn<strong>the</strong>sis of (-)-strychnine in 15 steps from 1,3-cyclohexanedione in 0.15% overall yield is<br />

described. The sequence followed in <strong>the</strong> assembling of rings is: E --> AE [2-(2-nitrophenyl)-1,3-<br />

cyclohexanedione] --> ACE (3a-aryloctahydroindol-4-one) --> ACDE (arylazatricyclic core)<br />

ABCDE (strychnan skeleton) --> ABCDEF (Wieland-Gumlich aldehyde) --> ABCDEFG<br />

(strychnine). The key steps of <strong>the</strong> syn<strong>the</strong>sis are <strong>the</strong> enantioselective construction of <strong>the</strong> 3a-(2-<br />

nitrophenyl)octahydroindol-4-one ring system and <strong>the</strong> closure of <strong>the</strong> piperidine ring by a reductive<br />

Heck cyclization to generate <strong>the</strong> pivotal intermediate (-)-14. In contrast, a Lewis acid promoted<br />

alpha-alkoxy-propargylic silane-enone cyclization did not lead to syn<strong>the</strong>tically useful azatricyclic<br />

ACDE intermediates. The introduction of C-17 and <strong>the</strong> closure of <strong>the</strong> indoline ring by reductive<br />

amination of <strong>the</strong> alpha-(2-nitrophenyl) ketone moiety complete <strong>the</strong> strychnan skeleton from which,<br />

via <strong>the</strong> Wieland-Gumlich aldehyde, <strong>the</strong> syn<strong>the</strong>sis of (-)-strychnine is achieved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Tripathi, Y. B. and S. Chaurasia<br />

Interaction of <strong>Strychnos</strong> nux vomica-products and iron: With reference to lipid pe<br />

2000<br />

Phytomedicine<br />

7(6): 523-528<br />

Abstract<br />

In this paper, it has been investigated that strychnine, <strong>the</strong> major active principle in <strong>the</strong> alcoholic<br />

extract of <strong>the</strong> seeds of <strong>Strychnos</strong> nux-vomica, is responsible <strong>for</strong> its antilipid peroxidative property.<br />

The mechanism of action of this drug is through <strong>the</strong> chelation of <strong>the</strong> free iron in <strong>the</strong> system. It has<br />

also been observed that strychnine does not have any pro-oxidant-property, because it does not<br />

convert Fe3+ to Fe2+ and vice versa in <strong>the</strong> reaction system, as has been observed with several o<strong>the</strong>r<br />

a n t i o x i d a n t s .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Wang, T. and J. M. Cook<br />

General approach <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of sarpagine/ajmaline indole alkaloids. Stereos<br />

2000<br />

Organic Letters<br />

2(14): 2057-2059<br />

Abstract<br />

GRAPHICS - (+)-Vellosimine has been syn<strong>the</strong>sized enantiospecifically in 27% overall yield from<br />

commercially available D-(+)-tryptophan methyl ester via <strong>the</strong> asymmetric Pictet-Spengler reaction<br />

and a stereocontrolled intramolecular palladium-coupling reaction as key steps.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Wong, C. L. and I. H. Ni<br />

Population dynamics of <strong>the</strong> feral macaques in <strong>the</strong> Kowloon Hills of Hong Kong<br />

2000<br />

American Journal of Primatology<br />

50(1): 53-66<br />

Abstract<br />

Hong Kong's feral monkey population is controversial. Many people complain about <strong>the</strong><br />

aggressiveness of <strong>the</strong> monkeys, while some conservationists urge <strong>the</strong> government to deal with <strong>the</strong><br />

problem in a way that will not harm <strong>the</strong> monkeys. The population dynamics of <strong>the</strong> macaques in <strong>the</strong><br />

Kowloon Hills were studied in 1992 and 1993. Vital statistics are provided from this study as a first<br />

step in resolving <strong>the</strong> problems of human provisioning and wildlife management. It is unlikely that<br />

<strong>the</strong>se macaques are indigenous to <strong>the</strong> area. They are <strong>the</strong> descendents of macaques that were released<br />

in <strong>the</strong> early twentieth century to control <strong>the</strong> spread of a local poisonous plant, <strong>the</strong> strychnos, which<br />

contains alkaloids poisonous to livestock and humans but which is a favorite food of <strong>the</strong> macaques.<br />

The macaque population expanded dramatically during <strong>the</strong> 1980s. The census method employed in<br />

this study is direct head count and photoidentification. At <strong>the</strong> end of 1993, <strong>the</strong> estimated abundance<br />

was 690 (+/- 6) in eight social groups in <strong>the</strong> Kowloon Hills. Species found were rhesus (Macaca<br />

mulatta) 65.3%, longtailed (M. fascicularis) 2.2%, Tibetan (M. thibetana) 0.2%, and hybrids 32.3%.<br />

The overall home ranges occupied 2.15 km(2), resulting in a very high macaque density of 326 per<br />

km(2). The birth rates were 56.9% and 69.4% in 1992 and 1993, respectively. Mean adult sex ratio<br />

(M:F) was 1:2.2 <strong>for</strong> social groups and 1:1.6 including all peripheral males. The main mortality factor<br />

was road accidents and <strong>the</strong>se contributed to <strong>the</strong> "missing rate" of 9.8% and 10.6% in 1992 and 1993,<br />

respectively. Population growth was 5.6% in 1992 and 9.8% in 1993. The estimated macaque<br />

population in <strong>the</strong> year 2000 will be around 1,100 if conditions remain favorable. Management<br />

strategies are recommended. (C) 2000 Wiley-Liss, Inc.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Yu, S., O. M. Berner and J. M. Cook<br />

General approach <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of indole alkaloids via <strong>the</strong> asymmetric pictet-s<br />

2000<br />

Journal of <strong>the</strong> American Chemical Society<br />

122(32): 7827-7828<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Zlotos, D. P.<br />

Stereochemistry of caracurine v<br />

2000<br />

Journal of Natural Products<br />

63(6): 864-865<br />

Abstract<br />

The 3D structure of <strong>the</strong> <strong>Strychnos</strong> alkaloid caracurine V was determined by means of NMR<br />

spectroscopy and semiempirical calculations. The previously unknown absolute configuration in <strong>the</strong><br />

central eight-membered ring was assigned as (16R, 16'R, 17R, and 17'R).<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Zlotos, D. P., S. Buller, C. Trankle and K. Mohr<br />

Bisquaternary caracurine v derivatives as allosteric modulators of ligand binding t<br />

2000<br />

Bioorganic and Medicinal Chemistry Letters<br />

10(22): 2529-2532<br />

Abstract<br />

The allosteric effect on muscarinic acetylcholine M-2 receptors of 11 bisquaternary salts of <strong>the</strong><br />

<strong>Strychnos</strong> alkaloid caracurine V was determined. The effect was indicated by <strong>the</strong> concentration<br />

which retarded <strong>the</strong> rate of dissociation of <strong>the</strong> antagonist [H-3]-N-methylscopolamine from porcine<br />

cardiac cholinoceptors by a factor of 2 (EC50). The most potent compounds carry allyl and<br />

propargyl substituents, respectively. Introduction of more bulky substituents (e.g., benzyl groups)<br />

resulted in a considerably reduced allosteric potency. The wide range of EC50 Values (3 nM <strong>for</strong> R =<br />

allyl, 1750 nM <strong>for</strong> R = 2-naphthyl) suggests a sterically restricted binding pocket. Molecular<br />

modeling studies indicated that <strong>the</strong> caracurine V ring system satisfies <strong>the</strong> pharmacophore model <strong>for</strong><br />

<strong>the</strong> allosteric interaction. (C) 2000 Elsevier Science Ltd. All rights reserved.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bennasar, M. L., J. M. Jimenez, B. Vidal, B. A. Sufi and J. Bosch<br />

Nucleophilic addition of 1-acetylindole enolates to pyridinium salts. Stereoselecti<br />

1999<br />

Journal of Organic Chemistry<br />

64(26): 9605-9612<br />

Abstract<br />

Addition of <strong>the</strong> enolate derived from 1-acetylindole (3) to pyridinium salt 4b followed by acidinduced<br />

cyclization of <strong>the</strong> resulting 1,4-dihydropyridine 5b in <strong>the</strong> presence of lithium iodide gives<br />

tetracyclic 3,7-methano[1,4]diazonino[1,2-alpha]indole 6b, which has subsequently been elaborated<br />

into <strong>the</strong> (E)-ethylidene derivative 7b. From this compound is reported a stereocontrolled route to (+/-<br />

)-geissoschizine, involving closure of C ring by Pummerer reaction, methanolysis of <strong>the</strong> resulting<br />

pentacyclic lactam 12, and desulfurization. A similar syn<strong>the</strong>tic sequence starting from <strong>the</strong> enolate of<br />

3 and 2-fluoropyridinium salt 15b gives access to <strong>the</strong> pentacyclic dilactam 2, which had previously<br />

b een converted to (+/-)-akagerine through opening of <strong>the</strong> piperidone (D) ring.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Brandt, V., M. Tits, A. Geerlings, M. Frederich, J. Penelle, C. Delaude, R. Verpoo<br />

Beta-carboline glucoalkaloids from <strong>Strychnos</strong> mellodora<br />

1999<br />

Phytochemistry<br />

51(8): 1171-1176<br />

Abstract<br />

Two new N-b-methylated beta-carbolinium glucoalkaloids, 3,4,5,6-tetradehydropalicoside and<br />

3,4,5,6-tetradehydrodolichantoside, toge<strong>the</strong>r with <strong>the</strong> known beta-carboline compounds<br />

desoxycordifoline (beta-carboline 3-carboxylate glucoalkaloid) and melinonine F (N-b-methylated<br />

harmanium cation), were isolated from <strong>Strychnos</strong> mellodora stembark. The structures of <strong>the</strong><br />

compounds were elucidated on <strong>the</strong> basis of spectroscopic studies. (C) 1999 Elsevier Science Ltd. All<br />

r i g h t s r e s e r v e d .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

da Silva, T. M. S., B. A. da Silva and R. Mukherjee<br />

The monoterpene alkaloid cantleyine from <strong>Strychnos</strong> trinervis root and its spasmo<br />

1999<br />

Phytomedicine<br />

6(3): 169-176<br />

Abstract<br />

Cantleyine, a monoterpene alkaloid isolated from <strong>the</strong> root bark of <strong>Strychnos</strong> trinervis, was submitted<br />

to a broad spectrum pharmacological screening, in which <strong>the</strong> principal effect observed was a<br />

nonspecific relaxation of isolated smooth muscles. Cantleyine relaxed (IC50 2.1 x 10(-4) M) <strong>the</strong><br />

guinea-pig trachea, pre-contracted by carbachol and antagonized in a nonspecific manner; carbachol<br />

(IC50 2.1 x 10(-4) M) and histamine (IC50 1.4 x 10(-4) M) induced contractions in <strong>the</strong> guinea-pig<br />

ileum; and phenylephrine (IC50 3.8 x 10(-4) M) responses in <strong>the</strong> rat aorta. Cantleyine antagonized<br />

(pD(2)', 3.82) cumulative concentration response curves to histamine in <strong>the</strong> ileum in a<br />

noncompetitive, reversible (slope, 4.84) and concentration dependent manner. The tonic contractions<br />

induced by histamine and KCl were also inhibited in a concentration-dependent and reversible<br />

manner (IC50 7.2 x 10(-5) and 1.8 x 10(-4) M, respectively), suggesting that cantleyine should be<br />

acting on voltage-dependent Ca2+ channels. This hypo<strong>the</strong>sis was confirmed by <strong>the</strong> observation that<br />

cantleyine inhibited (pD(2)', 3.35), in a concentration dependent manner, <strong>the</strong> CaCl2 induced<br />

contraction in depolarizing medium. These results suggest that cantleyine produces nonspecific<br />

spasmolytic effects in smooth muscle and that in guinea-pig ileum this effect is, in part, due to <strong>the</strong><br />

inhibition of Ca+2 influx through voltage-dependent Ca2+ channels.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Dassonneville, L., K. Bonjean, M. C. De Pauw-Gillet, P. Colson, C. Houssier, J.<br />

Stimulation of topoisomerase ii-mediated DNA cleavage by three DNA-intercalati<br />

1999<br />

Biochemistry<br />

38(24): 7719-7726<br />

Abstract<br />

Cryptolepine, matadine, and serpentine are three indoloquinoline alkaloids isolated from <strong>the</strong> roots of<br />

African plants: Cryptolepis sanguinolenta, <strong>Strychnos</strong> gossweileri, and Rauwolfia serpentina<br />

respectively. For a long time, <strong>the</strong>se alkaloids have been used in African folk medicine in <strong>the</strong> <strong>for</strong>m of<br />

plant extracts <strong>for</strong> <strong>the</strong> treatment of multiple diseases, in particular as antimalarial drugs. To date, <strong>the</strong><br />

molecular basis <strong>for</strong> <strong>the</strong>ir diverse biological effects remains poorly understood. To elucidate <strong>the</strong>ir<br />

mechanism of action, we studied <strong>the</strong>ir interaction with DNA and <strong>the</strong>ir effects on topoisomerase II.<br />

The strength and mode of binding to DNA of <strong>the</strong> three alkaloids were investigated by spectroscopy.<br />

The alkaloids bind tightly to DNA and behave as typical intercalating agents, All three compounds<br />

stabilize <strong>the</strong> topoisomerase II-DNA covalent complex and stimulate <strong>the</strong> cutting of DNA by<br />

topoisomerase Il. The poisoning effect is more pronounced with cryptolepine than with matadine and<br />

serpentine, but none of <strong>the</strong> drugs exhibit a preference <strong>for</strong> cutting at a specific base. Cryptolepine<br />

which binds 10-fold more tightly to DNA than <strong>the</strong> two related alkaloids proves to be much more<br />

cytotoxic toward B16 melanoma cells than matadine and serpentine. The cellular consequences of<br />

<strong>the</strong> inhibition of topoisomerase II by cryptolepine were investigated using <strong>the</strong> HL60 leukemia cell<br />

line. The flow cytometry analysis shows that <strong>the</strong> drug alters <strong>the</strong> cell cycle distribution, but no sign of<br />

drug-induced apoptosis was detected when evaluating <strong>the</strong> internucleosomal fragmentation of DNA<br />

in cells. Cryptolepine-treated cells probably die via necrosis ra<strong>the</strong>r than via apoptosis, The results<br />

provide evidence that DNA and topoisomerase II are <strong>the</strong> primary targets of cryptolepine, matadine,<br />

a n d s e r p e n t i n e .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Dassonneville, L., N. Wattez, C. Mahieu, P. Colson, C. Houssier, M. Frederich, M<br />

The plant alkaloid usambarensine intercalates into DNA and induces apoptosis in<br />

1999<br />

Anticancer Research<br />

19(6B): 5245-5250<br />

Abstract<br />

Usambarensine is a plant alkaloid isolated from <strong>the</strong> roots of <strong>Strychnos</strong> usambarensis collected in<br />

Central Africa. This bis-indole compound displays potent antiamoebic activities and shows<br />

antigardial, antimalarial and cytotoxic effects. Usamba-rensine is highly toxic to B16 melanoma<br />

cells and inhibits <strong>the</strong> growth of leukemia and carcinoma cells. To date <strong>the</strong> molecular basis <strong>for</strong> its<br />

diverse biological effects remains totally unknown. However; its capacity to inhibit nucleic acids<br />

syn<strong>the</strong>sis in melanoma cells, on <strong>the</strong> one hand, and its structural analogy with DNA-binding<br />

pyridoindole plant alkaloids recently studied (cryptolepine and matadine), on <strong>the</strong> o<strong>the</strong>r hand,<br />

suggested that usambarensine could also bind to DNA. Consequently we studied <strong>the</strong> strength and<br />

mode of binding to DNA of usambarensine by means of absorption, circular and lineal dichroism.<br />

The results of <strong>the</strong> optical measurements indicate that <strong>the</strong> alkaloid effectively: binds to DNA and<br />

behaves as a typical intercalating agent. Biochemical experiments indicated that, in contrast to<br />

cryptolepine and matadine, usambarensine does not interfere with <strong>the</strong> catalytic activity of<br />

topoisomerase II. Human HL60 leukemia cells were risen to assess <strong>the</strong> cytotoxicity of <strong>the</strong> alkaloid<br />

and its effect on <strong>the</strong> cell cycle. Usambarensine treatment is associated with a loss of cells in <strong>the</strong> G1<br />

phase accompanied with a large increase in <strong>the</strong> sub-G1 region which is characteristic of apoptotic<br />

cells. The DNA of usambarensine-treated cells was severely fragmented and <strong>the</strong> proteolytic activity<br />

of DEVD-caspases is enhanced. Usambarensine is thus characterized as DNA intercalator inducing<br />

a p o p t o s i s i n l e u k e m i a c e l l s .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Frederich, M., M. P. Hayette, M. Tits, P. De Mol and L. Angenot<br />

In vitro activities of <strong>Strychnos</strong> alkaloids and extracts against Plasmodium falcipar<br />

1999<br />

Antimicrobial Agents and Chemo<strong>the</strong>rapy<br />

43(9): 2328-2331<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Frederich, M., M. Tits, M. P. Hayette, V. Brandt, J. Penelle, P. DeMol, G. Llabres<br />

10'-hydroxyusambarensine, a new antimalarial bisindole alkaloid from <strong>the</strong> roots of<br />

1999<br />

Journal of Natural Products<br />

62(4): 619-621<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Furlanetto, C. and J. C. Dianese<br />

Some Pseudocercospora species and a new Prathigada species from <strong>the</strong> Brazilian<br />

1999<br />

Mycological Research<br />

103(Sep): 1203-1209<br />

Abstract<br />

Pseudocercospora bolkanii sp. nov., and P. luzardii sp. nov., were collected in <strong>the</strong> Brazilian cerrado<br />

on leaves of <strong>Strychnos</strong> pseudoquina, and Hancornia speciosa, respectively. Prathigada backmanii sp.<br />

nov., is described on leaf spots of Bowdichia virgilioides. Pseudocercospora curatellae on Curatella<br />

a m e r i c a n a i s i l l u s t r a t e d i n d e t a i l .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Hadden, C. E., B. D. Kaluzny, R. H. Robins and G. E. Martin<br />

Effects of n-oxidation on <strong>the</strong> n-15 chemical shifts in <strong>the</strong> strychnos alkaloids strych<br />

1999<br />

Magnetic Resonance in Chemistry<br />

37(4): 325-327<br />

Abstract<br />

The effects of N-oxidation on <strong>the</strong> N-15 chemical shifts of <strong>the</strong> <strong>Strychnos</strong> alkaloids strychnine and<br />

brucine are discussed. The N-15 shifts were determined using <strong>the</strong> inverse-detected, long-range<br />

GHMBC experiment at natural abundance. Following N-oxidation, <strong>the</strong> N-19 resonance shifted<br />

downfield from 35.0 ppm in strychnine to 136.3 ppm in <strong>the</strong> N-19-oxide. The N-19 resonance of<br />

brucine shifted downfield from 35.9 to 135.5 ppm in <strong>the</strong> N-19-oxide, Small upheld shifts were<br />

observed <strong>for</strong> <strong>the</strong> N-9 resonances of both N-oxides. The H-1 and C-13 shifts of both N-oxides were<br />

assigned using inverse-detected 2D NMR methods to ensure proper assignments of <strong>the</strong> long-range H-<br />

1-N-15 couplings. Copyright (C) 1999 John Wiley & Sons, Ltd.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

He, S. W. and V. H. Rawal<br />

General strategy <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> alkaloids<br />

1999<br />

Abstracts of Papers of <strong>the</strong> American Chemical Society<br />

218(Aug): U208-U209<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Julien-Laferriere, D.<br />

Fruit consumption, seed dispersal and seed fate in <strong>the</strong> vine <strong>Strychnos</strong> erichsonii in<br />

1999<br />

Revue D Ecologie<br />

54(4): 315-326<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kizil, M., B. Patro, O. Callaghan, J. A. Murphy, H. B. Hursthouse and D. Hibbs<br />

Tandem radical cyclizations on iodoaryl azides: Syn<strong>the</strong>sis of <strong>the</strong> core tetracycle of<br />

1999<br />

Journal of Organic Chemistry<br />

64(21): 7856-7862<br />

Abstract<br />

A new stereoselective approach to <strong>the</strong> tetracyclic core of Aspidosperma, alkaloids is described.<br />

Selective attack by tristrimethylsilylsilyl radicals on <strong>the</strong> aryl carbon-iodine bond of iodoaryl azides<br />

was first demonstrated on <strong>the</strong> simple model 15, thus both extending <strong>the</strong> recent discoveries of Kim<br />

and co-workers on aliphatic C-I bonds and demonstrating that <strong>the</strong> selectivity can be exploited in<br />

cascade radical cyclizations. Extension to <strong>the</strong> more complex substrate 25 af<strong>for</strong>ded <strong>the</strong> core ABCE<br />

tetracyclic skeleton of <strong>the</strong> alkaloids in excellent yield and with efficient control of relative<br />

s t e r e o c h e m i s t r y .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Liu, H. M., J. Orjala, O. Sticher and T. Rali<br />

Acylated flavonol glycosides from leaves of Stenochlaena palustris<br />

1999<br />

Journal of Natural Products<br />

62(1): 70-75<br />

Abstract<br />

From <strong>the</strong> leaves of Stenochlaena palustris five new O-acylated flavonol glycosides,<br />

stenopalustrosides A-E (1-5), have been isolated along with five known compounds, kaempferol 3-O-<br />

(3"-O-E-p-coumaroyl)-(6"-O-E-feruloyl)-beta-D-glucopyranoside (6), kaempferol 3-O-(3",6"-di-O-Ep-coumaroyl)-beta-D-glucopyranoside<br />

(7), kaempferol 3-O-(3"-O-E-p-coumaroyl)-beta-Dglucopyranoside<br />

(8), kaempferol 3-O-(6"-O-E-p-coumaroyl)-beta-D-glucopyranoside(9); and<br />

kaempferol 3-O-beta-D-glucopyranoside (10). The structures of <strong>the</strong> isolates were elucidated by<br />

spectroscopic methods, mainly 1D and 2D NMR. Compounds 1-4 showed significant antibacterial<br />

activities against Gram-positive strains. The structural difference between <strong>the</strong> isolated antibacterial<br />

a n d n o n a n t i b a c t e r i a l c o m p o u n d s i s d i s c u s s e d .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Martin, M. T., P. Rasoanaivo, G. Palazzino, C. Galeffi, M. Nicoletti, F. Trigalo an<br />

Minor n-b,c(21)-secocuran alkaloids of <strong>Strychnos</strong> myrtoides<br />

1999<br />

Phytochemistry<br />

51(3): 479-486<br />

Abstract<br />

From <strong>the</strong> stem bark of <strong>Strychnos</strong> myrtoides in addition to strychnobrasiline and malagashanine, four<br />

minor alkaloids, viz. malagashanol, 12-hydroxy-19-epi-malagashanine, myrtoidine and 11-<br />

demethoxymyrtoidine were isolated and <strong>the</strong>ir structures were established by 2-D NMR techniques.<br />

They belong to <strong>the</strong> series N-b,C(21)-secocuran and <strong>the</strong> two last show an additional alpha-beta<br />

unsaturated gamma-lactonic ring among C(18)-C(21). The biogenesis of <strong>the</strong>se alkaloids is also<br />

discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

McGrew, W. C., L. F. Marchant, R. W. Wrangham and H. Klein<br />

Manual laterality in anvil use: Wild chimpanzees cracking <strong>Strychnos</strong> fruits<br />

1999<br />

Laterality<br />

4(1): 79-88<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ndubani, P. a. and B. Hojer<br />

Traditional healers and <strong>the</strong> treatment of sexually transmitted illnesses in rural Zam<br />

1999<br />

Journal of Ethnopharmacology<br />

67(1): 15-25<br />

Abstract<br />

Lately <strong>the</strong>re has been increasing interest regarding <strong>the</strong> practice of traditional healers and <strong>the</strong>ir use of<br />

indigenous plants to treat illnesses. Twenty-three local healers (n'ganga) in Chiawa, rural Zambia,<br />

were interviewed about knowledge, practices, and <strong>the</strong>ir use of indigenous plants in <strong>the</strong> diagnosis and<br />

treatment of sexually transmitted illnesses (STIs) among male clients. They were also asked about<br />

<strong>the</strong>ir perceptions of modern medicine. The study revealed that all <strong>the</strong> n'ganga diagnosed and treated<br />

three main types of STIs. They named <strong>the</strong>m as: songeya, doroba and bola-bola. They treated <strong>the</strong><br />

illnesses with <strong>Strychnos</strong> cocculoides; Musa species; Solanum delegoense; Ximenia caffra;<br />

Diplorynchus condylocarpon; and Croton megalobotrys. Ten of <strong>the</strong> n'ganga perceived modern<br />

medicine to be effective against STIs and five of <strong>the</strong>m sometimes referred some of <strong>the</strong> clients to <strong>the</strong><br />

local health centre. It is being argued that a scheme to incorporate <strong>the</strong> n'ganga into STD control<br />

activities in which <strong>the</strong>y can be utilised to refer clients to modern medical facilities can be baneficial.<br />

Given <strong>the</strong> necessary health in<strong>for</strong>mation and support, <strong>the</strong> n'ganga may effectively execute this scheme.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Passarella, D., M. Martinelli, N. Llor, M. Amat and J. Bosch<br />

Biomimetic construction of <strong>the</strong> tetracyclic ring system of ngouniensine<br />

1999<br />

Tetrahedron<br />

55(52): 14995-15000<br />

Abstract<br />

2-Cyanotetrahydropyridine 9, bearing an indole-2-acetate moiety, was envisaged as a model<br />

syn<strong>the</strong>tic equivalent of <strong>the</strong> dihydropyridinium cations A, which have been proposed as common<br />

biogenetic intermediates to both ngouniensine and <strong>Strychnos</strong> indole alkaloids. Lewis acid-promoted<br />

cyclization of <strong>the</strong> O-silyl ketene acetal derived from 9 led to <strong>the</strong> ngouniensine-type derivative 11. (C)<br />

1999 Elsevier Science Ltd. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Penelle, J., M. Tits, P. Christen, V. Brandt, M. Frederich and L. Angenot<br />

Guiaflavine, a new bisindole quaternary alkaloid from <strong>the</strong> stem bark of <strong>Strychnos</strong><br />

1999<br />

Journal of Natural Products<br />

62(6): 898-900<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ramanitrahasimbola, D., S. Ratsimamanga-Urverg, P. Rasoanaivo and A. Rakoto-<br />

Effects of <strong>the</strong> naturally-occurring chemosensitizer malagashanine and its combina<br />

1999<br />

Phytomedicine<br />

6(5): 331-334<br />

Abstract<br />

Besides <strong>the</strong> determination of its LD50 value, <strong>the</strong> cytotoxicity against KB and P388 cell lines and <strong>the</strong><br />

toxicity on isolated guinea pig auricle of malagashanine and its combination with chloroquine were<br />

assessed. Malagashanine alone was devoid of cytotoxicity and cardiac effect on isolated auricle, and<br />

importantly, when combined to chloroquine, did not affect <strong>the</strong> inherent toxicity and cardiac toxicity<br />

o f t h i s a n t i m a l a r i a l a g e n t .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rukuni D<br />

Range-wide collection of <strong>Strychnos</strong> cocculoides: An important indigenous fruit tr<br />

1999<br />

Tree Seed News<br />

1: 8-11<br />

Abstract<br />

The description, distribution and seed collection strategy of <strong>Strychnos</strong> cocculoides, an important<br />

indigenous fruit tree spcies in Zimbabwe, are presented.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Sinha, M. K., A. K. Sinha and S. Adhikari<br />

Toxic effects of alkaloid extracts of <strong>Strychnos</strong> nux vomica, Datura metel and Arg<br />

1999<br />

Journal of Environmental Biology<br />

20(4): 293-298<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Sole, D., J. Bonjoch, S. Garcia-Rubio, E. Peidro and J. Bosch<br />

Total syn<strong>the</strong>sis of (-)-strychnine via <strong>the</strong> wieland-gumlich aldehyde<br />

1999<br />

Angewandte Chemie-International Edition<br />

38(3): 395-397<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Wells, P. B., K. E. Simons, J. A. Slipszenko, S. P. Griffiths and D. F. Ewing<br />

Chiral environments at alkaloid-modified platinum surfaces<br />

1999<br />

Journal of Molecular Catalysis a-Chemical<br />

146(1-2): 159-166<br />

Abstract<br />

Molecular environments at enantioselective sites are considered with reference to <strong>the</strong> adsorption of<br />

cinchonidine, epiquinidine, brucine, and oxycodone onto 6.3% Pt/silica (EUROPT-1), using <strong>the</strong><br />

hydrogenation of methyl pyruvate and of butane-2,3-dione as molecular probes. The mode of action<br />

of cinchonidine is briefly reviewed, and <strong>the</strong> ineffectiveness of epiquinidine is interpreted. Pt<br />

modified by <strong>the</strong> strychnos alkaloid brucine is active <strong>for</strong> <strong>the</strong> hydrogenation of methyl pyruvate at 10<br />

bar pressure and 293 K giving an enantiomeric excess of up to 20% in favour of S-lactate, but is not<br />

enantioselective <strong>for</strong> butane-2,3-dione hydrogenation. Modelling shows chat brucine adsorbed at a<br />

step at a Pt surface <strong>for</strong>ms a cavity which provides <strong>for</strong> <strong>the</strong> selective enantioface adsorption of methyl<br />

pyruvate, bur not of butane-2,3-dione, The model locates <strong>the</strong> site <strong>for</strong> alkaloid adsorption and <strong>the</strong> site<br />

<strong>for</strong> enantioselective hydrogenation on <strong>the</strong> same terrace of metal atoms. Pt modified by <strong>the</strong> morphine<br />

alkaloid oxycodone is enantioselective <strong>for</strong> <strong>the</strong> hydrogenation of both methyl pyruvate and butane-2,3-<br />

dione at 10 bar pressure and 293 K, <strong>the</strong> enantiomeric excess being typically 15% with respect to R-<br />

product in each case. Oxycodone, like brucine, appears to require a step site <strong>for</strong> adsorption but in<br />

this case modelling indicates that sites <strong>for</strong> alkaloid adsorption and <strong>for</strong> hydrogenation are on different<br />

terraces. The activity and enantioselectivity exhibited by cinchonidine-modified Pt is inhibited when<br />

modification and reaction are conducted under anaerobic conditions. The hypo<strong>the</strong>sis that coadsorption<br />

of alkaloid and oxygen limits <strong>the</strong> coverage of <strong>the</strong> <strong>for</strong>mer and that access to<br />

enantioselective sites becomes possible only after removal of adsorbed-oxygen in <strong>the</strong> early stages of<br />

reaction is tested. Modification has been carried out under atmospheres of propyne of of buta-1,3-<br />

diene as co-adsorbent; <strong>the</strong> resulting catalysts show high activity and enantioselectivity after removal<br />

of <strong>the</strong> co-adsorbent in <strong>the</strong> early stages of pyruvate hydrogenation. Thus, optimisation of Pt catalysts<br />

<strong>for</strong> enantioselective reaction should rake into account both metal particle geometry and alkaloid<br />

concentration. (C) 1999 Elsevier Science B.V. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Arai, T., H. Sasai, K. Yamaguchi and M. Shibasaki<br />

Regioselective catalytic asymmetric reaction of horner-wadsworth-emmons reage<br />

1998<br />

Journal of <strong>the</strong> American Chemical Society<br />

120(2): 441-442<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Arend, M., B. Westermann and N. Risch<br />

Modern variants of <strong>the</strong> mannich reaction<br />

1998<br />

Angewandte Chemie-International Edition<br />

37(8): 1045-1070<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Biala, R. G., M. Tits, J. Penelle, M. Frederich, V. Brandt, C. Prosperi, G. Llabres<br />

Strychnochrysine, a new bisindole alkaloid from <strong>the</strong> roots of <strong>Strychnos</strong> nux vomic<br />

1998<br />

Journal of Natural Products<br />

61(1): 139-141<br />

Abstract<br />

The reinvestigation of <strong>Strychnos</strong> nux-vomica resulted in <strong>the</strong> isolation of a colored monoquaternary<br />

bisindole alkaloid from <strong>the</strong> roots. The structure of this new orange substance, strychnochrysine (1),<br />

was defined by detailed spectroscopic methods.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Birman VB; Rawal VH<br />

A novel route to <strong>the</strong> geissoschizine skeleton: The influence of ligands on <strong>the</strong> diast<br />

1998<br />

Tetrahedron Letters<br />

39(40): 7219-7222<br />

Abstract<br />

A concise, novel route to <strong>the</strong> geissoschizine skeleton has been developed. The key step involves a<br />

Heck cyclization reaction, which was found to lead to opposite diastereomers, (+/-)-8 or (+/-)-9,<br />

depending on <strong>the</strong> reaction conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch, J., J. C. Fernandez and N. Valls<br />

Total syn<strong>the</strong>ses of (+/-)-deethylibophyllidine using a crisscross annulation: Ring c<br />

1998<br />

Journal of Organic Chemistry<br />

63(21): 7338-7347<br />

Abstract<br />

The total syn<strong>the</strong>sis of (+/-)-deethylibophyllidine (1) is described. Three different sequences provide<br />

this pentacyclic alkaloid using a common strategy involving a crisscross annulation. Key steps<br />

include (i) C/D ring cleavage of a 2-<strong>for</strong>myloctahydroindolo[2,3-a]quinolizine to obtain<br />

octahydroazecino[5,4-b]indoles, via ei<strong>the</strong>r a chloro<strong>for</strong>mate induced process or a quaternary<br />

ammonium salt <strong>for</strong>mation followed by treatment with lithium, and (ii) a tandem process consisting<br />

of an intramolecular Pictet-Spengler double cyclization upon a beta-indole position of a 2,3-<br />

disubstituted indole to generate <strong>the</strong> quaternary spiro center of <strong>the</strong> pentacyclic skeleton of<br />

ibophyllidine alkaloids. Attempts to extend <strong>the</strong> procedure to <strong>the</strong> construction of <strong>the</strong> pentacyclic<br />

framework of (+/-)ibophyllidine result in very low yield.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Cai, B. C., T. S. Wang, M. Kurokawa, K. Shiraki and M. Hattori<br />

Cytotoxicities of alkaloids from processed and unprocessed seeds of <strong>Strychnos</strong> nu<br />

1998<br />

Acta Pharmacologica Sinica<br />

19(5): 425-428<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Chen, X. and et al.<br />

Influence of processing methods on alkaloid, toxicity and effect of <strong>Strychnos</strong> nux<br />

1998<br />

China Journal of Chinese Materia Medica<br />

23(3): 151-153<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Fletcher, R., M. Kizil, C. Lampard, J. A. Murphy and S. J. Roome<br />

Tetrathiafulvalene-mediated stereoselective syn<strong>the</strong>sis of <strong>the</strong> tetracyclic core of asp<br />

1998<br />

Journal of <strong>the</strong> Chemical Society-Perkin Transactions 1<br />

(15): 2341-2351<br />

Abstract<br />

A novel route to advanced syn<strong>the</strong>tic precursors of Aspidosperma alkaloids is described, utilising<br />

r a d i c a l - p o l a r c r o s s o v e r r e a c t i o n s .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Frederich, M., J. Quetin-Leclercq, R. G. Biala, V. Brandt, J. Penelle, M. Tits and<br />

3 ',4 ',5 ',6 ' tetradehydrolongicaudatine y, an anhydronium base from <strong>Strychnos</strong> us<br />

1998<br />

Phytochemistry<br />

48(7): 1263-1266<br />

Abstract<br />

A new bisindole alkaloid, tetradehydrolongicaudatine Y, has been isolated from <strong>the</strong> stem bark of<br />

<strong>Strychnos</strong> usambarensis collected from <strong>the</strong> Ivory Coast. Elucidation of its structure is based mainly<br />

on spectroscopic studies and places it among <strong>the</strong> relatively small collection of zwitterionic<br />

indoloquinolizine alkaloids. (C) 1998 Elsevier Science Ltd. Al rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Frederich, M., M. Tits and L. Angenot<br />

Qualitative and quantitative evaluation of bisindole usambarane alkaloids in Stryc<br />

1998<br />

Phytochemical Analysis<br />

9(2): 63-66<br />

Abstract<br />

A high per<strong>for</strong>mance liquid chromatographic method <strong>for</strong> <strong>the</strong> simultaneous determination of bisindole<br />

usambarane alkaloids from <strong>the</strong> roots of <strong>Strychnos</strong> usambarensis using a diode-array detector is<br />

proposed, The system, consisting of a RP-8 Select B column and a linear gradient elution with<br />

acetonitrile and acetate buffer allowed <strong>the</strong> separation of all <strong>the</strong> alkaloids in 20 min, Usambarensine<br />

was found to be <strong>the</strong> major tertiary alkaloid present in <strong>the</strong> roots, In order to demonstrate <strong>the</strong><br />

possibility of quantifying <strong>the</strong> bisindole alkaloids in crude roots extracts, <strong>the</strong> quantitative evaluation<br />

of 3',4'-dihydrousambarensine, usambarensine and N-b-methylusambarensine was carried out. (C)<br />

1 9 9 8 J o h n W i l e y & S o n s , L t d .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Frederich, M., M. Tits and L. Angenot<br />

Qualitative and quantitative evaluation of bisindole usambarane alkaloids in Stryc<br />

1998<br />

Phytochemical Analysis<br />

9(2): 63-66<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Gharagozloo, P., M. Miyauchi, B. Birdsall and N. J. M. Birdsall<br />

Intramolecular diels-alder reactions of 3-(tetrahydropyridinyl)indoles: Stereoselec<br />

1998<br />

Journal of Organic Chemistry<br />

63(6): 1974-1980<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Hokelek, T., H. Gunduz, S. Patir and N. Uludag<br />

Spiro[carbazole-1(2h),2 '-[1,3]dithiolan]-4(3h)-one<br />

1998<br />

Acta Crystallographica Section C Crystal Structure Communications<br />

54(Sep): 1297-1299<br />

Abstract<br />

The title compound, C14H13NOS2, consists of a carbazole skeleton and a pentacyclic dithiolane<br />

ring bonded at position 1. The heteroatoms in <strong>the</strong> molecule are responsible <strong>for</strong> <strong>the</strong> changes in <strong>the</strong><br />

b o n d l e n g t h s a n d a n g l e s o f t h e c a r b a z o l e c o r e .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Jeyaraj, T., S. Deepa and A. C. Hary<br />

Water quality improvement using <strong>Strychnos</strong> potatorum nuts<br />

1998<br />

Indian Journal of Environmental Protection<br />

18(3): 211-214<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Kuehne, M. E., U. K. Bandarage, A. Hammach, Y. L. Li and T. Wang<br />

Application of ferrocenylalkyl chiral auxiliaries to syn<strong>the</strong>ses of indolenine alkaloi<br />

1998<br />

Journal of Organic Chemistry<br />

63(7): 2172-2183<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Liu, X. and W. Li<br />

Chemical constituents from maqianzi (Sstrychnos nux vomica)<br />

1998<br />

Chinese Traditional and Herbal Drugs<br />

29(7): 435-437<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Miao, P., D. C. Cai, B. R. Xiang, D. K. An and Y. Ito<br />

Separation and purification of strychnine from crude extract of <strong>Strychnos</strong> nux-vo<br />

1998<br />

Journal of Liquid Chromatography and Related Technologies<br />

21(1/2): 163-170<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Padwa, A. and A. T. Price<br />

Syn<strong>the</strong>sis of <strong>the</strong> pentacyclic skeleton of <strong>the</strong> aspidosperma alkaloids using rhodium<br />

1998<br />

Journal of Organic Chemistry<br />

63(3): 556-565<br />

Abstract<br />

A series of diazo amido keto esters prepared from N-alkenyl-substituted 3-carbalkoxy-2-piperidone<br />

derivatives was treated with rhodium(II) acetate. Attack of <strong>the</strong> amido carbonyl oxygen at <strong>the</strong><br />

resultant rhodium carbenoid center produced a transient push-pull carbonyl ylide dipole which<br />

underwent an intramolecular dipolar cycloaddition reaction. A related annulation sequence was used<br />

to prepare <strong>the</strong> pentacyclic skeleton of <strong>the</strong> aspidosperma family of alkaloids. Syn<strong>the</strong>sis of <strong>the</strong> required<br />

diazo imide was carried out from 3-carboxy-3-ethyl-2-piperidone and N-methyl-3-indoleacetic acid.<br />

Treatment of <strong>the</strong> diazo imide with rhodium(II) acetate af<strong>for</strong>ded a transient 1,3-dipole which<br />

subsequently underwent cycloaddition across <strong>the</strong> indole pi-bond. The resulting cycloadduct is <strong>the</strong><br />

consequence of endo cycloaddition with respect to <strong>the</strong> dipole which is fully in accord with <strong>the</strong><br />

lowest energy transition state. The cycloadduct was converted in three steps into desacetoxy-4-oxo-<br />

6,7-dihydrovindorosine. The stereochemistry of <strong>the</strong> final product was established by a X-ray<br />

c r y s t a l l o g r a p h i c s t u d y .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Shibasaki, M., A. Kojima and S. Shimizu<br />

Catalytic asymmetric syn<strong>the</strong>sis of natural products with heterocyclic rings<br />

1998<br />

Journal of Heterocyclic Chemistry<br />

35(5): 1057-1064<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Shibasaki, M., T. Iida and Y. M. A. Yamada<br />

Development of multifunctional asymmetric catalysts and <strong>the</strong>ir application to prac<br />

1998<br />

Journal of Syn<strong>the</strong>tic Organic Chemistry Japan<br />

56(5): 344-356<br />

Abstract<br />

This article focuses on a new concept in catalytic asymmetric syn<strong>the</strong>sis, which was first realized by<br />

<strong>the</strong> use of heterobimetallic complexes. As such complexes function at <strong>the</strong> same time as both a Lewis<br />

acid and a Bronsted base, similar to enzymes, <strong>the</strong>y make possible a variety of efficient catalytic<br />

asymmetric reactions. This "heterobimetallic" concept has proven to be applicable to a variety of<br />

new asymmetric catalyses. We have already succeeded in asymmetric nitroaldol reactions catalyzed<br />

by <strong>the</strong> LaLi(3)tris (binaphthoxide) complex (LLB) and asymmetric Michael reactions catalyzed by<br />

<strong>the</strong> LaNa(3)tris (binaphthoxide) complex (LSB). Now <strong>the</strong> LLB catalyst could also be applied<br />

efficiently to <strong>the</strong> tandem inter-intramolecular asymmetric nitroaldol reaction, af<strong>for</strong>ding a<br />

syn<strong>the</strong>tically useful bicyclic product with four newly generated chiral carbons in one pot.<br />

Fur<strong>the</strong>rmore we succeeded in <strong>the</strong> first direct asymmetric aldol reactions of aldehydes with<br />

unmodified ketones (up to 94% ee) by using a catalytic amount of LLB. While LLB was also<br />

effective in <strong>the</strong> hydrophosphonylation of aldehydes, asymmetric hydrophosphonylations of imines<br />

were efficiently catalyzed by <strong>the</strong> LnK(3)tris (binaphthoxide) complex (LnPB:Ln=rare earth metal<br />

such as La, Yb) (up to 96% ee). On <strong>the</strong> o<strong>the</strong>r hand, alkali metal free lanthanum complexes prepared<br />

from Ln(O-i-Pr)(3) (Ln=La or Yb) and 1,1'-binaphthol (BINOL) or 3-hydroxymethyl-BINOL were<br />

excellent catalysts <strong>for</strong> <strong>the</strong> asymmetric epoxidation of alpha,beta-unsaturated ketones (up to 94% eel.<br />

We also developed ano<strong>the</strong>r type of heterobimetallic catalysts featuring group 13 elements such as Al<br />

or Ga as a central metal. Among <strong>the</strong>m, <strong>the</strong> AlLibis(binaphthoxide) complex (ALB) is an effective<br />

catalyst <strong>for</strong> asymmetric Michael reactions of malonates or Horner-Wadsworth-Emmons reagents (up<br />

to 99% ee) and <strong>for</strong> asymmetric tandem Michael-aldol reactions. Applications bi this catalyst to<br />

syn<strong>the</strong>ses of biologically important compounds such as 11-deoxy-PGF(1 alpha) and tubifolidine are<br />

also described. Fur<strong>the</strong>rmore <strong>the</strong> GaLibis (binaphthoxide) complex (GaLB) in combination with<br />

molecular sieves 4 A was found to be an efficient catalyst <strong>for</strong> asymmetric ring openings of a variety<br />

o f e p o x i d e s w i t h t - B u S H ( u p t o 9 7 % e e ) .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Shimizu, S., K. Ohori, T. Arai, H. Sasai and M. Shibasaki<br />

Catalytic asymmetric syn<strong>the</strong>sis of tubifolidine<br />

1998<br />

Journal of Organic Chemistry<br />

63(21): 7547-7551<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Shin K; Moriya M; Ogasawara K<br />

Enantio- and diastereocontrolled syn<strong>the</strong>sis of (-)-19(s)-acetoxy-n-1-acetyl-20-epit<br />

1998<br />

Tetrahedron Letters<br />

39(22): 3765-3768<br />

Abstract<br />

An enantiocontrolled route to <strong>the</strong> 19-oxygenated pentacyclic <strong>Strychnos</strong> alkaloids has been<br />

demonstrated by <strong>the</strong> stereoselective syn<strong>the</strong>sis of (-)-19(S)-acetoxy-N-1-acetyl-20-epitubifolidine. (C)<br />

1998 Elsevier Science Ltd. All rights reserved.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Visen, P. K. S., B. Saraswat, K. Raj, A. P. Bhaduri and M. P. Dubey<br />

Prevention of galactosamine-induced hepatic damage by <strong>the</strong> natural product logan<br />

1998<br />

Phyto<strong>the</strong>rapy Research<br />

12(6): 405-408<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Zhang, Z. and et al.<br />

Determination of strychnine and brucine in poisonnut (<strong>Strychnos</strong> nux vomica) and<br />

1998<br />

Chinese Traditional and Herbal Drugs<br />

29(4): 236-237<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Amat M: Hadida S; Pshenichnyi G; Bosch J<br />

Palladium(0)-catalyzed heteroarylation of 2- and 3-indolylzinc derivatives. An effi<br />

1997<br />

Journal of Organic Chemistry<br />

62(10): 3158-3175<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Amat M; Coll MD; Bosch J; Espinosa E; Molins E<br />

Total syn<strong>the</strong>ses of <strong>the</strong> <strong>Strychnos</strong> indole alkaloids (-)-tubifoline, (-)-tubifolidine, an<br />

1997<br />

Tetrahedron Asymmetry<br />

8(6): 935-948<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bandopadhyay J; De B<br />

Seasonal variation of strychnine and brucine in vegetative parts of <strong>Strychnos</strong> nux-<br />

1997<br />

International Journal of Pharmacognosy<br />

35(5): 349-353<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bian J; Cai DG; Liu ZL (et al)<br />

Study on extraction of strychnine from <strong>Strychnos</strong> piersiana a. W. Hill by co~2-sfe<br />

1997<br />

Chinese Journal of Pharmaceuticals<br />

28(1): 5-7<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch J; Sole D; Cuesta X<br />

Syn<strong>the</strong>sis and con<strong>for</strong>mational analysis of cis-3a-(o-nitrophenyl)octahydroindol-4-<br />

1997<br />

Heterocycles<br />

45(2): 315-322<br />

Abstract<br />

The preparation of 1-methyl-3a-(o-nitrophenyl)octahydroindol-4-ol derivatives from 2-allyl-2-(onitrophenyl)-1,3-cyclohexan<br />

(1) and <strong>the</strong> preferred con<strong>for</strong>mation of <strong>the</strong> azabicyclic ring system of<br />

t h e s e c o m p o u n d s a r e r e p o r t e d .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch J; Sole D; Garcia Rubio S; Bosch J<br />

A general syn<strong>the</strong>tic entry to strychnos alkaloids of <strong>the</strong> curan type via a common 3<br />

1997<br />

Journal of <strong>the</strong> American Chemical Society<br />

119(31): 7230-7240<br />

Abstract<br />

A general strategy <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of pentacyclic <strong>Strychnos</strong> alkaloids with <strong>the</strong> curan skeleton has<br />

been developed. It utilizes 3a-(2-nitrophenyl)hexahydroindol-4-one (23), which was prepared from 2-<br />

alkyl-2-(2-nitrophenyl)-1,3-cyclohexanedione (15), as <strong>the</strong> common, pivotal intermediate. Three<br />

different procedures have been employed <strong>for</strong> <strong>the</strong> closure of <strong>the</strong> bridged piperidine D ring from 23: (i)<br />

an intramolecular Michael-type conjugate addition; (ii) a Ni(COD)(2)-promoted biscyclization that<br />

assembles B and D rings in a single syn<strong>the</strong>tic step, and (iii) an intramolecular cyclization of an<br />

enone-propargylic silane system. when necessary, depending on <strong>the</strong> procedure used, introduction of<br />

<strong>the</strong> oxidized one-carbon substituent at C-16, closure of <strong>the</strong> indole ring, and/or adjustment of <strong>the</strong><br />

functionality of <strong>the</strong> C-20 two-carbon chain constitute <strong>the</strong> last stages of <strong>the</strong> syn<strong>the</strong>tic route to <strong>the</strong> title<br />

alkaloids. The procedure involving <strong>the</strong> cyclization of a propargylic silane has been successfully<br />

extended to <strong>the</strong> enantiospecific syn<strong>the</strong>sis of (-)-tubifolidine starting from <strong>the</strong> enantiopure 3a-(2-<br />

nitrophenyl)hexahydroindolone (-)-51, which was prepared taking advantage of <strong>the</strong> prochiral<br />

c h a r a c t e r o f c y c l o h e x a n e d i o n e 1 5 .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

DeLaude C; DeLaude L<br />

African <strong>Strychnos</strong> alkaloids<br />

1997<br />

Bulletin Societe Royale Des Sciences De Liege<br />

66(4): 183-286<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Gu Z; Li T; Xiao O; Chen J; Lian W<br />

Studies on <strong>the</strong> chemical constituents of <strong>Strychnos</strong> nitida G Don<br />

1997<br />

Zhongguo Zhongyao Zazhi<br />

22(1): 40-41<br />

Abstract<br />

Six compounds were isolated from <strong>the</strong> root and stem of <strong>Strychnos</strong> nitida <strong>for</strong> <strong>the</strong> first time. On <strong>the</strong><br />

basis of chemical properties and spectral data, <strong>the</strong> compounds were identified as beta-sitosterol,<br />

strychnine, brucine, cantieyine, lignoceric acid and palmitic acid.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Gu ZP; Zhang SM; Wang CL; Lian WY; Xiao PG; Chen JM<br />

Determarion of strychnine and brucine in <strong>Strychnos</strong> by HPLC<br />

1997<br />

Acta Pharmaceutica Sinica<br />

32(10): 791-794<br />

Abstract<br />

The determination of strychnine and brucine by HPLC is described and its application to <strong>the</strong> seeds,<br />

roots, stems and leaves of 10 <strong>Strychnos</strong> species from various parts of China is reported. The<br />

analytical column used was ZY110 YNG-C18. The mobile phase was (0.01 m KH2PO4):MeOH<br />

(73:27), at pH 2.5 regulated by 10% H3PO4. Flow rate was 1.0 ml/min. The detection wavelength<br />

was 264 nm. The linear range was 0.18-7.26 micro g <strong>for</strong> strychnine and 0.11-4.32 micro g <strong>for</strong><br />

brucine. The recoveries of strychnine and brucine were 98.27% and 98.04%, respectively. Results<br />

showed that strychnine and brucine contents exhibited great differences between samples from<br />

different species. The contents of strychnine in <strong>the</strong> seeds of <strong>Strychnos</strong> wallichiana and S. ignatii<br />

were 5.6% and 3.9%, respectively, showing that <strong>the</strong>se 2 <strong>Strychnos</strong> species could be developed as<br />

s o u r c e s o f s t r y c h n i n e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Kuehne, M. E. and F. Xu<br />

Syn<strong>the</strong>ses of strychnan- and aspidospermatan-type alkaloids. 9. The enantioselecti<br />

1997<br />

Journal of Organic Chemistry<br />

62(23): 7950-7960<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Mapaure, I.<br />

A floristic classification of <strong>the</strong> vegetation of a <strong>for</strong>est-savanna boundary in sou<strong>the</strong>a<br />

1997<br />

Bothalia<br />

27(2): 185-193<br />

Abstract<br />

The vegetation of Chirinda Forest boundary was classified into eight types using Two-way Indicator<br />

Species Analysis (TWINSPAN) and Detrended Correspondence Analysis (DCA). The moist <strong>for</strong>est<br />

comprises three types: <strong>Strychnos</strong> mellodora-Chrysophyllum gorungosanum Forest on deep dolerite<br />

soils; Chrysopllyllum gorungosanum-Myrianthus holstii Forest on shallow dolerite soils; and Teclea<br />

nobilis-Ehretia cymosa Forest on drier, but deep dolerite soils. The non-<strong>for</strong>est vegetation comprises<br />

five types: Themeda triandra Grassland on shallow dolerite soils; Psidium guajava Bushland on<br />

sandstone; Bridelia micrantha-Harunguna madagascariensis Mixed Woodland not restricted to any<br />

one particular soil type; Acacia karroo-Heteropyxis dehniae Woodland on shallow soils derived from<br />

sandstone but sometimes on dolerite; and Julbernardia globiflora-Brachystegia spici<strong>for</strong>mis<br />

( M i o m b o ) W o o d l a n d o n s a n d s t o n e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Martin, S. F.<br />

General strategies <strong>for</strong> <strong>the</strong> stereoselective syn<strong>the</strong>sis of alkaloid natural products<br />

1997<br />

Pure and Applied Chemistry<br />

69(3): 571-576<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Montgomery, J., M. V. Chevliakov and H. L. Brielmann<br />

Nickel-catalyzed heterocycle construction with stereoselective exocyclic alkene in<br />

1997<br />

Tetrahedron<br />

53(48): 16449-16462<br />

Abstract<br />

A series of monocyclic and bicyclic heterocycles with exocyclic alkenes were constructed in a<br />

stereoselective fashion by an organozinc/Ni(COD)(2)-mediated cyclization of alkynyl enones. Both<br />

reductive and alkylative cyclization manifolds were accessible depending on <strong>the</strong> ligand and<br />

organozinc structure. Alkylative cyclizations were generally more efficient than reductive<br />

cyclizations, particularly with cyclic substrates. (C) 1997 Elsevier Science Ltd.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Mukherjee, R., T. M. S. daSilva, J. B. L. Guimaraes, E. D. Oliveira, P. A. Keifer a<br />

Tertiary alkaloid fraction of strychnos atlantica: Confirmation of <strong>the</strong> identity and s<br />

1997<br />

Phytochemical Analysis<br />

8(3): 115-119<br />

Abstract<br />

The identity and structures of <strong>the</strong> three main tertiary indole alkaloids of <strong>Strychnos</strong> atlantica were<br />

confirmed and verified by high held nuclear magnetic resonance (NMR) spectroscopy. Complete H-<br />

1 and C-13 NMR spectral assignments were obtained. (C) 1997 by John Wiley & Sons, Ltd.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Ohba M; Kubo H; Fujii T; Ishibashi H; Sargent MV; Arbain D<br />

Syn<strong>the</strong>sis and absolute configuration of (-)-normalindine<br />

1997<br />

Tetrahedron Letters<br />

38(38): 6697-6700<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Okada, K., K. Murakami and H. Tanino<br />

Asymmetric syn<strong>the</strong>sis of <strong>the</strong> pentacyclic ring system of aspidosperma alkaloids<br />

1997<br />

Tetrahedron<br />

53(42): 14247-14254<br />

Abstract<br />

The asymmetric syn<strong>the</strong>sis of pentacyclic compound 1 3, a known intermediate in <strong>the</strong> syn<strong>the</strong>sis of 1-<br />

acetylaspidospermidine, was conducted via <strong>the</strong> condensation of 2-hydroxytryptamine with chiral C9<br />

lactone 9, readily available from triol 4. (C) 1997 Elsevier Science Ltd.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Patir, S., G. Okay, A. Gulce, B. Salih and T. Hokelek<br />

Intermediates <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of tetracyclic indole alkaloids. Syn<strong>the</strong>sis of 4-amin<br />

1997<br />

Journal of Heterocyclic Chemistry<br />

34(4): 1239-1242<br />

Abstract<br />

An efficient method <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of 4-aminotetrahydrocarbazole derivatives from 2,3-<br />

dihydrospiro-[1H-carbazole-1,2'-(1,3)-dithiolan]-4-(9H)-one 1 is described. The structure of<br />

compound 6 has been confirmed by X-ray structure analysis.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Saxton, J. E.<br />

Recent progress in <strong>the</strong> chemistry of <strong>the</strong> monoterpenoid indole alkaloids<br />

1997<br />

Natural Product Reports<br />

14(6): 559-590<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Thepenier, P., M. J. Jacquier, G. Massiot, L. Le Men-Olivier and C. Delaude<br />

Alcaloiedes de <strong>Strychnos</strong> zenkeri<br />

1997<br />

Bulletin Societe Royale Des Sciences De Liege<br />

66(5): 341-344<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Zhou, G., N. Liu, X. Sun and et al.<br />

Determination of strychnine content in <strong>the</strong> seeds of <strong>Strychnos</strong> nux vomica by silia<br />

1997<br />

Chinese Pharmaceutical Journal<br />

32(9): 553-558<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Amat, M., M. D. Coll, D. Passarella and J. Bosch<br />

An enantioselective syn<strong>the</strong>sis of <strong>the</strong> <strong>Strychnos</strong> alkaloid (-)-tubifoline<br />

1996<br />

Tetrahedron Asymmetry<br />

7(10): 2775-2778<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bennasar, M. L., E. Zulaica, A. Ramirez and J. Bosch<br />

Syn<strong>the</strong>tic ef<strong>for</strong>ts toward akuammiline alkaloids from tetracyclic 6,7-seco derivativ<br />

1996<br />

Journal of Organic Chemistry<br />

61(4): 1239-1251<br />

Abstract<br />

The addition of enolates derived from indole-3-acetic esters 1-3 to pyridinium salts 4, 23, and 24,<br />

followed by acid cyclization of <strong>the</strong> resulting 1,4-dihydropyridines, leads to tetrahydro-1,5-<br />

methanoazocino[3,4-b]indoles 5-7, 25-27, which have been subsequently elaborated into 4Eethylidene(or<br />

4 alpha-ethyl)-hexahydro-1,5-methanoazocino[3,4-b]indoles. Closure of <strong>the</strong> sixmembered<br />

C ring of akuammiline alkaloids by <strong>for</strong>mation of C-6/C-7 bond from appropriately N-(b)-<br />

substituted derivatives of <strong>the</strong>se tetracyclic ABDE substructures has been extensively investigated. In<br />

<strong>the</strong> N-unsubstituted indole series, both cyclization of thionium ions generated ei<strong>the</strong>r by Pummerer<br />

reaction from sulfoxide 16 or by DMTSF treatment of dithioacetal 36 and photocyclization of<br />

chloroacetamide 47 occur upon <strong>the</strong> indole nitrogen to give pentacycles 18, 38, and 49, respectively.<br />

When <strong>the</strong> indole nitrogen is blocked by a substituent, <strong>the</strong> thionium ions derived from sulfoxides 17<br />

and 43 and dithioacetals 37 and 44 do not cyclize and lead to different products depending on <strong>the</strong><br />

reaction conditions, whereas chloroacetamides 48 and 51 undergo a reductive photodehalogenation.<br />

Attempted radical cyclization of seleno derivatives 53, 55, and 56 under a variety of conditions gives<br />

<strong>the</strong> corresponding reduced products. Finally, attempted photoisomerization of 1-acylindole 62 leads<br />

t o t h e N - ( b ) - m e t h y l t e t r a c y c l e 6 3 .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjean, K. A. P. M., M. C. A. J. dePauwGillet, J. QuetinLeclercq, L. Angenot an<br />

In vitro cytotoxic activity of two potential anticancer drugs isolated from Strychno<br />

1996<br />

Anticancer Research<br />

16(3A): 1129-1137<br />

Abstract<br />

The cytotoxicity and <strong>the</strong> selective antiprotozoal activity of some <strong>Strychnos</strong> alkaloids, namely<br />

strychnopentamine (SP) and usambarensine (US) (7) led us to analyze and compare <strong>the</strong>ir effects with<br />

emetine (EM) by using mouse B16 melanoma cells cultivated in vitro. We observed by cytological<br />

analysis and proliferation rate studies that <strong>the</strong>se substances induce analogous cytotoxic effects in<br />

B16 cells, but at different concentrations i.e. <strong>for</strong>mation of lamellar bodies in <strong>the</strong> cytoplasm, <strong>the</strong><br />

which contain pre-melanosomes in <strong>the</strong> case of SP and US, vacuoles and blebs. At concentrations<br />

near <strong>the</strong>ir respective IC50, SP and US, but not EM, decreased colony <strong>for</strong>mation. We showed by<br />

incorporation of labelled precursors that SP and US first inhibit RNA syn<strong>the</strong>sis while EM initially<br />

acts on protein syn<strong>the</strong>sis. These alkaloids increased melanin syn<strong>the</strong>sis. Fur<strong>the</strong>rmore, only EM and<br />

SP caused hemolysis of sheep red blood corpuscles. This could explain why <strong>the</strong> rate of<br />

antiplasmodial activity is higher <strong>for</strong> SP and EM.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch, J., J. Catena and N. Valls<br />

Total syn<strong>the</strong>sis of (+/-)-deethylibophyllidine: Studies of a fischer indolization rout<br />

1996<br />

Journal of Organic Chemistry<br />

61(20): 7106-7115<br />

Abstract<br />

The total syn<strong>the</strong>sis of (+/-)-deethylibophyllidine is described, proceeding in eight steps from 4-<br />

(methoxyphenyl)ethylamine in 5% overall yield (Scheme 6). In terms of sequential annulation, <strong>the</strong><br />

strategy involves <strong>the</strong> following operations: E --> DE --> ABDE --> ABCDE (Scheme 1). The key<br />

steps in <strong>the</strong> syn<strong>the</strong>sis are <strong>the</strong> stereoselective <strong>for</strong>mation of octahydroindol-6-ones by acid treatment of<br />

dihydroanisole derivatives, <strong>the</strong> regioselective Fischer indolization to obtain octahydropyrrolo-[3,2-<br />

c]carbazoles, and <strong>the</strong> tandem process consisting of Pummerer rearrangement upon a beta-amino<br />

sulfoxide and thionium ion cyclization upon a beta-indole position of a 2,3-disubstituted indole to<br />

generate <strong>the</strong> quaternary spiro center. Attempts to effect <strong>the</strong> construction of <strong>the</strong> pentacyclic<br />

framework by means of Fischer indolization of <strong>the</strong> octahydropyrrolo[3,2,1-hi]indol-6-one resulted in<br />

f a i l u r e ( S c h e m e 2 ) .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bosch, J., J. Bonjoch and M. Amat<br />

The <strong>Strychnos</strong> alkaloids<br />

1996<br />

Alkaloids<br />

48: 75-189<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bosch, J., M. L. Bennasar and M. Amat<br />

A general method <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of bridged indole alkaloids<br />

1996<br />

Pure and Applied Chemistry<br />

68(3): 557-560<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Cai, B. C., T. Nagasawa, S. Kadota, M. Hattori, T. Namba and Y. Kuraishi<br />

Processing of nux vomica .7. Antinociceptive effects of crude alkaloids from <strong>the</strong> p<br />

1996<br />

Biological and Pharmaceutical Bulletin<br />

19(1): 127-131<br />

Abstract<br />

We examined <strong>the</strong> antinociceptive effects of <strong>the</strong> crude alkaloid fractions (CAF) of nux vomica (<strong>the</strong><br />

dried seeds of <strong>Strychnos</strong> nux-vomica L.) and <strong>the</strong> influences of various processing methods upon<br />

<strong>the</strong>ir antinociception in three analgesic tests in mice, In <strong>the</strong> tail-pressure test, <strong>the</strong> CAF (0.01-1 mu<br />

g/kg, i.p.) of nux vomica that was unprocessed or treated with sand-, licorice-, oil- or vinegar and<br />

sand-processing showed clear antinociception. The CAF (1 mu g/kg, i.p.) of vinegar-processed nux<br />

vomica showed antinociception, without effects at lower doses of 0.01 and 0.1 mu g/kg and those<br />

treated with urine- or urine and sand-processing were without effects at doses of 0.01-1 mu g/kg.<br />

Morphine (2 mg/kg, s.c.) showed short-lasting antinociception, without effects at a dose of 1 mu<br />

g/kg. In <strong>the</strong> hot-plate test, <strong>the</strong> CAF (100 mu g/kg, i.p.) of nux vomica having undergone sandprocessing<br />

produced a significant antinociception, without effects at lower doses of 0.01 and 1 mu<br />

g/kg. The CAF (0.01-100 mu g/kg, i.p.) of nux vomica that was unprocessed or treated with oil- or<br />

vinegar and sand-processing and morphine (1 and 100 mu g/kg, s.c.) were without effects. In <strong>the</strong><br />

acetic acid-induced writhing test, <strong>the</strong> CAF (1 mu g/kg, i.p.) of nux vomica that was treated with sandprocessing<br />

significantly inhibited <strong>the</strong> writhing behavior, while those of nux vomica that was<br />

unprocessed or treated with oil- or vinegar and sand-processing and morphine were without effects<br />

at a dose of 1 mu g/kg. The present results demonstrate <strong>the</strong> antinociceptive effects of <strong>the</strong> CAF of nux<br />

vomica and suggest that sand-processing is good <strong>for</strong> <strong>the</strong> analgesic potency of nux vomica. It is also<br />

suggested that <strong>the</strong> CAF of nux vomica has distinct antinociceptive potency, even after treatment with<br />

l i c o r i c e - , o i l - , v i n e g a r a n d s a n d - p r o c e s s i n g .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Fletcher, R. J., D. E. Hibbs, M. Hursthouse, C. Lampard, J. A. Murphy and S. J. R<br />

Stereocontrolled syn<strong>the</strong>sis of complex polycycles using tetrathiafulvalene mediate<br />

1996<br />

Chemical Communications<br />

(6): 739-740<br />

Abstract<br />

Tetracyclic heterocycles are prepared in a stereocontrolled manner using radical-polar crossover<br />

c h e m i s t r y .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Forns, P., A. Diez and M. Rubiralta<br />

Syn<strong>the</strong>tic applications of 2-(1,3-dithian-2-yl)indoles .7. Syn<strong>the</strong>sis of aspidospermi<br />

1996<br />

Journal of Organic Chemistry<br />

61(22): 7882-7888<br />

Abstract<br />

A new method of syn<strong>the</strong>sizing <strong>the</strong> alkaloid aspidospermidine (1), based on building ring E on <strong>the</strong><br />

pyridocarbazole [ABCD] ring structure, is reported. The preparation of <strong>the</strong> pyridocarbazole<br />

framework of Aspidosperma alkaloids is a new three-step syn<strong>the</strong>tic application of 2-(1,3-dithian-2-<br />

yl)indoles. A tandem conjugate addition-alkylation reaction starting from indolyldithiane (4), 3-<br />

methylenelactam 8, and EtI yields <strong>the</strong> adduct 17. Treatment of lactam 17 with DIBALH leads to<br />

<strong>for</strong>mation of <strong>the</strong> naphthyridoindole 18. Compound 18 isomerizes in aqueous AcOH to yield<br />

pyridocarbazole 3. Finally, closure of ring E and subsequent reduction of <strong>the</strong> dithiane ring produces<br />

aspidospermidine. Pyridocarbazoles 2 and 10 were prepared as models.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ho, L. M., I. Cheong and H. A. Jalil<br />

Rhabdomyolysis and acute renal failure following blowpipe cart poisoning<br />

1996<br />

Nephron<br />

72(4): 676-678<br />

Abstract<br />

The latex of pokok ipoh (Antiaris toxocaria) and <strong>the</strong> root bark of akar ipoh (<strong>Strychnos</strong> species) have<br />

been <strong>the</strong> main sources of <strong>the</strong> poisonous principles in dart and arrow poisons prepared throughout<br />

south-east Asia. We report a fatal case of rhabdomyolysis and acute oliguric renal failure following<br />

oral ingestion of blowpipe dart poison. To our knowledge this is <strong>the</strong> first such report.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ishibashi, H. and M. Ikeda<br />

Recent progress in electrophilic aromatic substitution with alpha-thiocarbocations<br />

1996<br />

Reviews on Heteroatom Chemistry<br />

14: 59-82<br />

Abstract<br />

This review summarizes <strong>the</strong> recent work on electrophilic aromatic substitution with alphathiocarbocations.<br />

Emphasis has been made on <strong>the</strong> structural modification and variation of <strong>the</strong><br />

reaction conditions of alpha-chlorosulfides or sulfoxides to accomplish <strong>the</strong> reactions. The literature<br />

from 1991 to January 1996 are covered in this review.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kuehne, M. E., T. S. Wang and D. Seraphin<br />

Syn<strong>the</strong>ses of strychnos and aspidospermatan-type alkaloids .8. Selective total synt<br />

1996<br />

Journal of Organic Chemistry<br />

61(22): 7873-7881<br />

Abstract<br />

Mossambine (6) was obtained by a six-step reaction sequence from <strong>the</strong> indoloazepine ester 7.<br />

Radical cyclization of <strong>the</strong> tetracyclic vinyl iodide 12a provided a racemic pentacyclic ketone 16E,<br />

which could be converted to ei<strong>the</strong>r enantiomer by condensation with (S or R)-N,S-dimethyl-Sphenylsulfoximine<br />

and selective pyrolysis of <strong>the</strong> resulting diastereomeric alcohols 18 and 19 or 20<br />

and 21. Selective reductions of <strong>the</strong> resolved (or racemic) ketone 16E provided mossambine (6) and<br />

i t s h y d r o x y e p i m e r 1 7 .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Martin, S. F., C. W. Clark, M. Ito and M. Mortimore<br />

A biomimetic approach to <strong>the</strong> <strong>Strychnos</strong> alkaloids. A novel, concise syn<strong>the</strong>sis of (<br />

1996<br />

Journal of <strong>the</strong> American Chemical Society<br />

118(40): 9804-9805<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Mavar-Manga, H., J. Quetin-Leclercq, G. Llabres, M. L. Belem-Pinheiro, A. F. Im<br />

9-methoxygeissoschizol, an alkaloid from bark of <strong>Strychnos</strong> guianensis<br />

1996<br />

Phytochemistry<br />

43(5): 1125-1127<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Mukaiyama, T., I. Shiina, H. Iwadare, M. Saitoh, K. Nishimura, T. Nishimura, N.<br />

An asymmetric syn<strong>the</strong>sis of <strong>the</strong> bc ring system of 8-epitaxoids by way of intramol<br />

1996<br />

Chemistry Letters<br />

(6): 483-484<br />

Abstract<br />

Optically active 1 alpha-allyl-1 beta,11 beta-benzylidenedioxy-2 alpha,10 beta-bis(benzyloxy)-7<br />

beta,9 beta-isopropylidenedioxy-8 alpha,12,12-trimethyl-4-methylenebicyclo[6.4.0]dodecane (2)(1)<br />

which corresponds to BC ring system of 8-epitaxoids was prepared in high yield from ketoaldehyde<br />

8 via intramolecular aldol cyclization and successive stereoselective methylation reactions. The<br />

ketoaldehyde 8 was syn<strong>the</strong>sized from 8-membered ring compound 3 by stereoselective Michael<br />

a d d i t i o n u s i n g h i g h e r - o r d e r c u p r a t e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Nuzillard, J. M., P. Thepenier, M. J. Jacquier, G. Massiot, L. Le Men-Olivier and<br />

Alkaloids from root bark of <strong>Strychnos</strong> panganensis<br />

1996<br />

Phytochemistry<br />

43(4): 897-902<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Oliveira, E. J., I. A. Medeiros and R. Mukherjee<br />

Hypotensive and spasmolytic effects of normacusine b from <strong>Strychnos</strong> atlantica ro<br />

1996<br />

Phytomedicine<br />

3(1): 45-49<br />

Abstract<br />

Normacusine B, a tertiary indole alkaloid, was isolated in pure <strong>for</strong>m from <strong>the</strong> root bark of <strong>Strychnos</strong><br />

atlantica Krukoff & Barneby. In conscious unrestrained rats, normacusine B (1 mg/kg) decreased <strong>the</strong><br />

mean arterial blood pressure (27.6 +/- 8.4 mmHg, n = 6), followed by a significant increase in heart<br />

rate (115.0 +/- 12.7 bpm, n = 6). The alkaloid failed to induce tachycardia directly in isolated<br />

perfused rat heart. In isolated rat aortic rings, normacusine B antagonized phenylephrine and<br />

serotonin-induced contractions. Schild plot analysis of individual cumulative concentration-response<br />

curves was compatible with a competitive type of antagonism against phenylephrine (pA(2) = 7.05<br />

+/- 0.11) and of a non-competitive nature against 5-hydroxytryptamine (apparent pA(2) = 7.02 -<br />

0.08). Normacusine B was found inactive against KCl and PGF(2 alpha) induced contractions.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Passarella, D., S. Sathyanarayana, M. Amat and J. Bosch<br />

Studies on <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> alkaloids<br />

1996<br />

Natural Product Letters<br />

8(1): 75-82<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Patir, S., P. Rosenmund and P. H. Goetz<br />

A new syn<strong>the</strong>tic route to <strong>the</strong> tetracyclic framework of strychnos alkaloids via intra<br />

1996<br />

Heterocycles<br />

43(1): 15-22<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rasoanaivo, P., C. Galeffi, G. Palazzino and M. Nicoletti<br />

Revised structure of malagashanine: A new series of n-b,c(21)-secocuran alkaloid<br />

1996<br />

Gazzetta Chimica Italiana<br />

126(8) 517-519<br />

Abstract<br />

The structure of malagashanine previously assigned as a N-b,C(3)-secocuran alkaloid is indeed a<br />

new type of N-b,C(21)-secocuran alkaloid. The structure of a minor related alkaloid, 12-<br />

h y d r o x y m a l a g a s h a n i n e , i s a l s o r e p o r t e d .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Rasoanaivo, P., S. Ratsimamanga-Urverg and F. Frappier<br />

Recent results on <strong>the</strong> pharmacodynamics of alkaloids from strychnos in madagasc<br />

1996<br />

Cahiers Sante<br />

6(4): 249-253<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Saxton, J. E.<br />

Recent progress in <strong>the</strong> chemistry of <strong>the</strong> monoterpenoid indole alkaloids<br />

1996<br />

Natural Product Reports<br />

13(4) 327-363<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Sole D: Bosch J; Bonjoch J<br />

3a-(o-nitrophenyl)octahydroindol-4-ones: Syn<strong>the</strong>sis and spectroscopic analysis<br />

1996<br />

Tetrahedron<br />

52(11): 4013-4028<br />

Abstract<br />

A short entry to 3a-(o-nitrophenyl)octahydroindol-4-ones employing ozonolysis and double<br />

reductive amination of 2-allyl-2-(o-nitrophenyl)-1,3-cyclohexanedione (9) is described. The<br />

symmetric dione 9 is syn<strong>the</strong>sized in a 50% overall yield from 1,3-cyclohexanedione by means of o-<br />

nitroarylation followed by O-allylation and subsequent Claisen rearrangement. Configurational and<br />

con<strong>for</strong>mational aspects of azabicyclic derivatives 1 (a-k) are discussed.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Sole D; Bonjoch J; Bosch J<br />

Total syn<strong>the</strong>sis of <strong>the</strong> <strong>Strychnos</strong> alkaloids (+/-)-akuammicine and (+/-)-norfluoroc<br />

1996<br />

Journal of Organic Chemistry<br />

61(13): 4194-4195<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Sole D; Bonjoch J; GarciaRubio S; Suriol R; Bosch J<br />

A new solution <strong>for</strong> <strong>the</strong> construction of <strong>the</strong> piperidine ring of <strong>Strychnos</strong> alkaloids fr<br />

1996<br />

Tetrahedron Letters<br />

37(29): 5213-5216<br />

Abstract<br />

Alkylation of cis-3a-(o-nitrophenyl)hexahydroindol-4-one 1 with 1-iodo-4-(trimethylsilyl)-2-butyne<br />

followed by BF3 . Et(2)O-promoted cyclization of <strong>the</strong> resulting propargylic silane 2 af<strong>for</strong>ded <strong>the</strong><br />

tricyclic vinylidene ketone 3, which was fur<strong>the</strong>r converted to <strong>the</strong> <strong>Strychnos</strong> alkaloids tubifolidine,<br />

19,20-dihydroakuammicine, and akuammicine. Copyright (C) 1996 Elsevier Science Ltd


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Sole D; GarciaRubio S; Bosch J; Bonjoch J<br />

Syn<strong>the</strong>sis and reactivity of a 3-vinylidenepiperidine as a model study of alpha-alle<br />

1996<br />

Heterocycles<br />

43(11): 2415-2424<br />

Abstract<br />

4-Acetonyl-1-benzyl-3-vinylidenepiperidine (8), prepared by cyclization of propargylic silane (7),<br />

was used as a model to study <strong>the</strong> usefulness of <strong>the</strong> allene moiety as a precursor of <strong>the</strong> two-carbon<br />

chain present in <strong>the</strong> piperidine ring of <strong>Strychnos</strong> alkaloids.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Thepenier P; Jacquier MJ; Nuzillard JM; Massiot G; Le Men-Olivier L; Delaude<br />

Alkaloids from <strong>the</strong> seeds of <strong>Strychnos</strong> pungens<br />

1996<br />

Bulletin Societe Royale Des Sciences De Liege<br />

65(6): 379-382<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Thepenier P; Jacquier MJ; Nuzillard JM; Massiot G; Le Men-Olivier L; Delaude<br />

<strong>Strychnos</strong> xantha alkaloids<br />

1996<br />

Bulletin Societe Royale Des Sciences De Liege<br />

65(6): 383-386<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Tits M; Brandt V; Wauters JN; Delaude C; Llabres G; Angenot L<br />

Glucoindole alkaloids from stem bark of <strong>Strychnos</strong> mellodora<br />

1996<br />

Planta Medica<br />

62(1): 73<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Tripathi YB; Chaurasia S<br />

Studies on <strong>the</strong> inhibitory effect of <strong>Strychnos</strong> nux vomica-alcohol extract on iron in<br />

1996<br />

Phytomedicine<br />

3(2): 175-180<br />

Abstract<br />

This report investigates <strong>the</strong> antioxidant property of <strong>Strychnos</strong> nux vomica Linn. alcohol extract on<br />

FeSO4-induced lipid peroxidation in vitro. The results have been compared to those of vitamin E,<br />

parabenzoquinone, Tris, mannitol and EDTA. Tris and mannitol, <strong>the</strong> standard hydroxyl trappers<br />

failed to block this process. Interestingly EDTA, a strong metal chelator, significantly blocks <strong>the</strong><br />

process of lipid peroxidation. S. nux vomica inhibits <strong>the</strong> lipid peroxidation in <strong>the</strong> dose dependent<br />

manner. The inhibition of lipid peroxidation was reversed by adding high concentration of Fe2+.<br />

This suggests <strong>the</strong> mechanism of action of S. nux vomica through <strong>the</strong> chelation of Fe++/Fe+++ ion in<br />

<strong>the</strong> system and not by trapping <strong>the</strong> hydroxyl radicals. This extract significantly maintains <strong>the</strong> hepatic<br />

glutathione content also in <strong>the</strong> time and dose dependent manner even in <strong>the</strong> presence of FeSO4,<br />

which is not <strong>the</strong> case with EDTA. It also inhibits <strong>the</strong> process of lipid peroxidation once induced.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Tripathi YB; Chaurasia S<br />

Effect of <strong>Strychnos</strong> nux vomica alcohol extract on lipid peroxidation in rat liver<br />

1996<br />

International Journal of Pharmacognosy<br />

344): 295-299<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Wright CW; Phillipson JD; Awe SO; Kirby GC Warhurst DC; QuetinLeclercq J;<br />

Antimalarial activity of cryptolepine and some o<strong>the</strong>r anhydronium bases<br />

1996<br />

Phyto<strong>the</strong>rapy Research<br />

10(4): 361-363<br />

Abstract<br />

Eight naturally occurring anhydronium bases and <strong>the</strong> syn<strong>the</strong>tic quaternary compound Nbmethylharmalane<br />

were tested against Plasmodium falciparum (strain K1) in vitro. Cryptolepine was<br />

found to have similar activity to that of chloroquine but alstonine, 5,6-dihydroflavopereirine,<br />

matadine, Nb-methylharmalanae, melinonine F, normelinonine F, strychnoxanthine and serpentine<br />

were found to have little activity. Cryptolepine, given orally to mice infected with Plasmodium<br />

berghei berghei was found to have moderate antimalarial activity; parasitaemia was suppressed by<br />

8 0 % a t 5 0 m g / k g / d a y .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Yamada H; Minematsu Y; Nakamura T; Mise M; Fujisaki H; Oguri K<br />

Brucine as a potent inducer of cyp2b3, <strong>the</strong> third member of <strong>the</strong> cyp2b subfamily p<br />

1996<br />

Biological and Pharmaceutical Bulletin<br />

19(2): 291-293<br />

Abstract<br />

We have indicated that strychnine and brucine induce concurrently an unknown p450 (2B-UP)<br />

which cross-reacts with anti-CYP2B1 antibody (Fujisaki et al., J. Pharmacol. Exp. Ther., 268, 1024-<br />

1031, 1994). We purified ZB-UP from brucine-treated rats and characterized it in this study. The<br />

purification was achieved by solubilization with sodium cholate followed by successive<br />

chromatographic steps with omega-aminoctyl-Sepharose 4B, DEAE-Sephacel and hydroxyapatite.<br />

The minimum molecular weight of purified 2B-UP was calculated to be 48000 by sodium dodecyl<br />

sulfate-gel electrophoresis. This preparation showed no Soret peak in <strong>the</strong> ultraviolet absorption<br />

spectrum indicating absence of heme. The amino terminal sequence of ZB-UP up to <strong>the</strong> 10th residue<br />

was consistent with <strong>the</strong> deduced amino acid sequence of CYP2B3 cDNA, but did not agree with <strong>the</strong><br />

sequences of CYP2B1/2. The result strongly suggests that ZB-UP is CYP2B3. Thus, we indicated<br />

here that <strong>Strychnos</strong> alkaloid, brucine, is a potent inducer of <strong>the</strong> CYP2B3 or <strong>the</strong> closely related P450.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ahmad, S. K. and J. S. Prasad<br />

Efficacy of foliar extracts against preharvest and postharvest diseases of sponge-g<br />

1995<br />

Letters in Applied Microbiology<br />

21(6): 373-375<br />

Abstract<br />

The inhibitory potential of aqueous foliar extracts of Adhatoda vasica, Azadirachta indica,<br />

Catharan<strong>the</strong>s roseus, Datura fistulosa, Lantana camara, Muraya exotica, Ocimum sanctum, Ricinus<br />

communis and <strong>Strychnos</strong> nux-vomica were evaluated against soft rot diseases of sponge-gourd fruits<br />

caused by Helminthosporium spiciferum and Fusarium scirpi. Conidial germination of F. scirpi and<br />

H. spiciferum were reduced to about 75% when <strong>the</strong>ir spores were treated with A. indica, C. roseus,<br />

D. fistulosa, L. camara, M. exotica and O. sanctum. Considerable reductions (50%) in mycelial dry<br />

weights and colony diameters were recorded in liquid media containing (20%) aqueous extracts of<br />

C, roseus, D. fistulosa and M, exotica. O<strong>the</strong>r extracts reduced <strong>the</strong> mycelial growth but to a lesser<br />

extent. Post-infection treatment of sponge-gourd fruits with <strong>the</strong> extracts of A. indica, L. camara, M.<br />

exotica, O. sanctum, D. fistulosa and C. roseus almost fully inhibited <strong>the</strong> spread of disease.<br />

Treatment of fruits with A. indica and C. roseus be<strong>for</strong>e fungal infection reduced <strong>the</strong> spread of<br />

disease caused by both <strong>the</strong> pathogens, whereas M. exotica, O. sanctum and D. fistulosa reduced <strong>the</strong><br />

spread of soft-rot caused by F. scirpi but not by H, spiciferum.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Amat, M., D. Coll and J. Bosch<br />

Enantiopure intermediates <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> alkaloids<br />

1995<br />

Tetrahedron<br />

51(39): 10759-10770<br />

Abstract<br />

The addition of 2-(lithiomethyl)indole 2 to <strong>the</strong> enantiopure oxazolinylpyridine 18 followed by acidic<br />

treatment af<strong>for</strong>ded a mixture of tetracyclic compounds 21a and 21b in a 3:2 ratio. The major epimer<br />

21a was converted to tetracycle 25a, a tetracyclic ABDE substructure of <strong>Strychnos</strong> alkaloids.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bandyopadyay, J., B. De and P. C. Datta<br />

Presence of vomicine in callus culture of <strong>Strychnos</strong> nux vomica<br />

1995<br />

Fitoterapia<br />

66 (2): 183<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bonjoch, J., D. Sole and J. Bosch<br />

Studies on <strong>the</strong> syn<strong>the</strong>sis of strychnos indole alkaloids - syn<strong>the</strong>sis of (+/-)-dehydrot<br />

1995<br />

Journal of <strong>the</strong> American Chemical Society<br />

117(44): 11017-11018<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bosch, J. and M. L. Bennasar<br />

Method <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of bridged indole alkaloids - addition of carbon nucleoph<br />

1995<br />

Synlett<br />

(6): 587-596<br />

Abstract<br />

The methodology based on <strong>the</strong> nucleophilic addition of stabilized carbon nucleophiles to N-<br />

alkylpyridinium salts constitutes a powerful tool <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of bridged indole alkaloids<br />

belonging to a variety of structural types, ei<strong>the</strong>r tetracyclic (as vinoxine and ervitsine) or pentacyclic,<br />

in <strong>the</strong> latter case after closure of <strong>the</strong> tryptamine chain by cyclization upon <strong>the</strong> indole ring.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Caira, M. R. and P. Rasoanaivo<br />

Structure of malagashanine, a new alkaloid with chloroquine-potentiating action<br />

1995<br />

Journal of Chemical Crystallography<br />

25(11): 725-729<br />

Abstract<br />

The molecular structure of malagashanine (C23H30N2O4), a new alkaloid occurring in Madagascan<br />

<strong>Strychnos</strong> species and showing chloroquine-potentiating action, has been determined by single<br />

crystal X-ray diffraction. The crystals, in <strong>the</strong> <strong>for</strong>m of a 1:1 acetone solvate, are monoclinic, space<br />

group P2(1), with a = 10.328(2), b = 10.554(6), c = 11.490(5)Angstrom, beta = 96.67(2)degrees, Z =<br />

2. Refinement based on 3650 reflections measured at 294K yielded R = 0.045. The X-ray analysis<br />

shows that <strong>the</strong> ring system in malagashanine differs from that in alkaloids of <strong>the</strong> strychnobrasiline<br />

type in containing only five- and six-membered rings. Thermal analysis of <strong>the</strong> solvate indicates that<br />

<strong>the</strong> acetone molecules are firmly held in <strong>the</strong> crystal and <strong>the</strong> X-ray analysis reveals that <strong>the</strong>y are<br />

trapped in crystal voids. Only van der Waals <strong>for</strong>ces and C-H ... O hydrogen bonds stabilize <strong>the</strong><br />

c r y s t a l s t r u c t u r e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Corsaro, M. M., I. Giudicianni, R. Lanzetta, C. E. Marciano, P. Monaco and M. P<br />

Polysaccharides from seeds of <strong>Strychnos</strong> species<br />

1995<br />

Phytochemistry<br />

39(6): 1377-1380<br />

Abstract<br />

The chemical composition of polysaccharide fractions from <strong>Strychnos</strong> nux-vomica and S. innocua<br />

seeds and comparison with those from S. potatorum seeds are reported. The structural features of <strong>the</strong><br />

galactomannans from <strong>the</strong> three <strong>Strychnos</strong> species are also discussed.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Delaude, C., P. Thepenier, M. J. Jacquier, J. M. Nuzillard, G. Massiot and L. Le<br />

Alcaloides de <strong>Strychnos</strong> angolensis<br />

1995<br />

Bulletin Societe Royale Des Sciences De Liege<br />

64(4/5): 243-246<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Hattori, M., T. Nakabayashi, Y. A. Lim, H. Miyashiro, M. Kurokawa, K. Shiraki,<br />

Inhibitory effects of various ayurvedic and panamanian medicinal-plants on <strong>the</strong> in<br />

1995<br />

Phyto<strong>the</strong>rapy Research<br />

9(4): 270-276<br />

Abstract<br />

Extracts of 40 Ayurvedic medicines and 39 Panamanian medicinal plants were screened <strong>for</strong> <strong>the</strong>ir<br />

inhibitory activity on <strong>the</strong> plaque <strong>for</strong>mation of herpes simplex virus type I (HSV-1) in cultured cells,<br />

The extracts of II plant species showed potent inhibitory activity at a concentration of 100 mu g/mL,<br />

while those of ten species showed moderate activities, Repeated oral administration of each extract<br />

of Rhus acuminata (galls), Saraca indica (bark), <strong>Strychnos</strong> potatrum (seeds) appreciably suppressed<br />

<strong>the</strong> development of typical skin lesions induced by infection of HSV-1 in BALB/c mice, The extract<br />

of S. potatrum prolonged both development of skin lesion and mean survival time. This indicates<br />

that S. potatrum is a possible candidate <strong>for</strong> <strong>the</strong>rapeutic application <strong>for</strong> HSV-1 infection.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

He, Y. and et al.<br />

Influence of different processing methods on four alkaloid contents in <strong>Strychnos</strong> n<br />

1995<br />

China Journal of Chinese Materia Medica<br />

20(2): 84<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kizil, M. and J. A. Murphy<br />

Stereoselective preparation of <strong>the</strong> abce tetracycle of aspidospermidine and related<br />

1995<br />

Journal of <strong>the</strong> Chemical Society-Chemical Communications<br />

(14): 1409-1410<br />

Abstract<br />

Tandem radical cyclisation af<strong>for</strong>ds stereoselective access to <strong>the</strong> ABCE tetracyclic substructure of<br />

a s p i d o s p e r m i d i n e a n d r e l a t e d a l k a l o i d s .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Knight, S. D., L. E. Overman and G. Pairaudeau<br />

Syn<strong>the</strong>sis applications of cationic aza-cope rearrangements .28. Asymmetric total<br />

1995<br />

Journal of <strong>the</strong> American Chemical Society<br />

117(21): 5776-5788<br />

Abstract<br />

The first asymmetric total syn<strong>the</strong>ses of (-)-strychnine, ent-strychnine, and <strong>the</strong> Wieland-Gumlich<br />

aldehyde are described with full experimental details. The total syn<strong>the</strong>sis of (-)-strychnine was<br />

realized in 24 steps and 3% overall yield from (1R,4S)-(+)-4-hydroxy-2-cyclopentenyl acetate (28).<br />

This syn<strong>the</strong>sis fully controls <strong>the</strong> six stereogenic centers and <strong>for</strong>ms <strong>the</strong> C(20) double bond of (-)-<br />

strychnine with high diastereoselection (>20:1). In <strong>the</strong> first stage of <strong>the</strong> syn<strong>the</strong>sis, <strong>the</strong> (R)-<br />

cyclopentenylstannane 8 is prepared in nine steps and 30% overall yield (40% with one recycle of<br />

38) as summarized in Scheme 4. Palladium-catalyzed carbonylative coupling of 8 with <strong>the</strong> 2-<br />

iodoaniline derivative 7 provides enone 6, which is converted to <strong>the</strong> 2-azabicyclo[3.2.1]octane 5 in<br />

seven additional steps. This latter sequence proceeds in 36% overall yield (Scheme 6). The central<br />

step of <strong>the</strong> total syn<strong>the</strong>sis is aza-Cope-Mannich rearrangement of 5 which proceeds in 98% yield to<br />

<strong>for</strong>m <strong>the</strong> pentacyclic intermediate 4 (Scheme 7). In five additional steps 4 is converted to <strong>the</strong><br />

Wieland-Gumlich aldehyde 2, which is <strong>the</strong> ultimate precursor of (-)strychnine. A slight modification<br />

of this syn<strong>the</strong>sis strategy allowed ent-strychnine to be prepared and provided <strong>the</strong> first samples of this<br />

unnatural enantiomer <strong>for</strong> pharmacological studies (Scheme 8). The efficiency and conciseness of this<br />

syn<strong>the</strong>sis provide an important benchmark of <strong>the</strong> power of <strong>the</strong> aza-Cope rearrangement-Mannich<br />

reaction to solve <strong>for</strong>midable problems in alkaloid construction.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Kuehne, M. E., C. S. Brook, D. A. Frasier and F. Xu<br />

Syn<strong>the</strong>ses of strychnos-type and aspidospermatan-type alkaloids .7. Total syn<strong>the</strong>se<br />

1995<br />

Journal of Organic Chemistry<br />

60(6): 1864-1867<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kuehne, M. E., T. S. Wang and D. Seraphin<br />

The total syn<strong>the</strong>sis of (+/-)-mossambine<br />

1995<br />

Synlett<br />

(5): 557-558<br />

Abstract<br />

A radical cyclization providing <strong>the</strong> pentacyclic strychnos skeleton which can be fur<strong>the</strong>r elaborated to<br />

f o r m t h e a l k a l o i d m o s s a m b i n e i s d e s c r i b e d .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Martin, G. E., R. C. Crouch and C. W. Andrews<br />

N-15 chemical shifts and long-range h-1-n-15 coupling pathways of selected Stryc<br />

1995<br />

Journal of Heterocyclic Chemistry<br />

32(6): 1759-1766<br />

Abstract<br />

The <strong>Strychnos</strong> alkaloids have been <strong>the</strong> focal point of considerable syn<strong>the</strong>tic and spectroscopic ef<strong>for</strong>t.<br />

We now report <strong>the</strong> N-15 chemical shifts and long-range H-1-N-15 coupling pathways of strychnine,<br />

brucine, and holstiine at natural abundance. Long-range coupling pathways were established using a<br />

gradient-enhanced HMQC sequence optimized <strong>for</strong> <strong>the</strong> observation of H-1-N-15 long-range couplings.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Micouin L; Diez A; Castells J; Lopez D; Rubiralta M; Quirion JC; Husson HP<br />

Syn<strong>the</strong>tic applications of 2-(1,3-dithian-2-yl)indoles .5. Asymmetric-syn<strong>the</strong>sis of<br />

1995<br />

Tetrahedron Letters<br />

36(10): 1693-1696<br />

Abstract<br />

Chiral tetracyclic dasycarpidone-type compounds (alpha R, IS, 5R)-4 and (alpha R, IR, 5S)-16 have<br />

been syn<strong>the</strong>sized from 2-(1,3-dithian-2-yl)indole 6 and (alpha R)-N-(beta-hydroxy-alphaphenylethyl)-Delta(3)-piperidein-2-one<br />

8 in three steps, following <strong>the</strong> methodology that we<br />

d e s c r i b e d r e c e n t l y .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Nagaraja, T. G.<br />

Some biochemical changes in leaves of <strong>Strychnos</strong> nux vomica during infection of<br />

1995<br />

Advances in Plant Sciences<br />

8(2): 258-260<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Nagaraja, T. G. and A. N. Thite<br />

Enzymatic studies in leaves of <strong>Strychnos</strong> nux vomica Linn infected with Meliola s<br />

1995<br />

Advances in Plant Sciences<br />

8(2): 406-409<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Patir, S.<br />

A new syn<strong>the</strong>tic route to <strong>the</strong> azocino[4,3-b]indole core structure<br />

1995<br />

Liebigs Annalen<br />

(8): 1561-1562<br />

Abstract<br />

The reaction of 2 with 2-methoxyethylamine in <strong>the</strong> presence of ZnCl2 af<strong>for</strong>ded imine 3, which was<br />

reduced with NaBH4 to amine 4 without isolation. After deprotection of <strong>the</strong> carbonyl function by<br />

treatment with benzeneseleninic anhydride, ketone 5 was converted to compound 6 with 2-<br />

oxobutyric acid and dicyclohexylcarbodiimide. The isodasycarpidone derivative 7, <strong>for</strong>med by aldol<br />

reaction of 6, represents a tetracyclic substructure of strychnos-type alkaloids.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq, J., A. Favel, G. Balansard, P. Regli and L. Angenot<br />

Screening <strong>for</strong> in-vitro antifungal activities of some indole alkaloids<br />

1995<br />

Planta Medica<br />

61(5): 475-477<br />

Abstract<br />

Several indole alkaloids were tested by <strong>the</strong> agar dilution technique on a panel of human pathogenic<br />

fungi, yeasts, and dermatophytes. Our results indicate that <strong>the</strong> most active compounds possess a betacarboline<br />

skeleton and that <strong>the</strong> presence of a 3-4 double bond enhances <strong>the</strong> activity. Our results also<br />

show that antifungal activities are not Linked to <strong>the</strong> cytotoxic, antimicrobial or antiparasitic<br />

p r o p e r t i e s .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq, J., G. Llabres, R. Warin, M. L. Belempinheiro, H. Mavarmanga an<br />

Guianensine, a zwitterionic alkaloid from <strong>Strychnos</strong> guianensis<br />

1995<br />

Phytochemistry<br />

40(5): 1557-1560<br />

Abstract<br />

The isolation and structural determination of an alkaloid isolated from <strong>the</strong> stem bark of <strong>Strychnos</strong><br />

guianensis is described. Elucidation of its structure is based mainly on 1D and 2D NMR studies. The<br />

new alkaloid has a zwitterionic asymmetrical bis-indole structure and is named guianensine.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ranganath, H. R. and K. Veenakumari<br />

Notes on <strong>the</strong> dacine fruit-flies (Diptera, Tephritidae) of Andaman and Nicobar Isla<br />

1995<br />

Raffles Bulletin of Zoology<br />

43(1): 235-238<br />

Abstract<br />

A survey of <strong>the</strong> fruit fly fauna in <strong>the</strong> Andaman and Nicobar islands revealed 11 species belonging to<br />

<strong>the</strong> genus Bactrocera. Three species reared, one each from Spondias pinnata (L. f) Kurz<br />

(Anacardiaceae) and <strong>Strychnos</strong> andamanensis Hill (Loganiaceae), and one from S. andamanensis<br />

and several cucurbits, are probably new to science.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Saxton, J. E.<br />

Recent progress in <strong>the</strong> chemistry of <strong>the</strong> monoterpenoid indole alkaloids<br />

1995<br />

Natural Product Reports<br />

12(4): 385-411<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Zong, Y. Y. and C. T. Che<br />

Determination of strychnine and brucine by capillary zone electrophoresis<br />

1995<br />

Planta Medica<br />

61(5): 456-458<br />

Abstract<br />

A procedure <strong>for</strong> quantitative estimation of strychnine and brucine in <strong>the</strong> extracts of <strong>Strychnos</strong> nuxvomica<br />

seeds by capillary zone electrophoresis (CZE) was developed. The buffer solution used was<br />

10mM phosphate buffer-MeOH (9:1), pH 2.5. The linear calibration range was 0.01-0.15 mg/ml.<br />

This method is useful <strong>for</strong> <strong>the</strong> qualitative and quantitative determination of strychnine and brucine in<br />

p lant drug samples, as well I as in human plasma.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Adinolfi, M., M. M. Corsaro, R. Lanzetta, M. Parrilli, G. Folkard, W. Grant and J.<br />

Composition of <strong>the</strong> coagulant polysaccharide fraction from <strong>Strychnos</strong> potatorum s<br />

1994<br />

Carbohydrate Research<br />

263(1): 103-110<br />

Abstract<br />

The composition of <strong>the</strong> coagulant polysaccharide fraction from <strong>Strychnos</strong> potatorum seeds is<br />

described. This fraction comprises a 1:1.7 mixture of a galactomannan and a galactan. The structure<br />

of <strong>the</strong>se polysaccharides is also discussed. In addition, <strong>the</strong> coagulant properties of <strong>the</strong> polysaccharide<br />

fractions of two o<strong>the</strong>r <strong>Strychnos</strong> species, innocua and nux-vomica, have been assayed.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Amat M; Sathyanarayana S; Hadida S; Bosch J<br />

Short <strong>for</strong>mal syn<strong>the</strong>ses of indole alkaloids of <strong>the</strong> uleine and <strong>Strychnos</strong> groups<br />

1994<br />

Tetrahedron Letters<br />

35(38): 7123<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Cai, B. C., H. Wu, X. W. Yang and M. Hattori<br />

Analysis of spectral data <strong>for</strong> ^1^3cnmr of sixteen <strong>Strychnos</strong> alkaloids<br />

1994<br />

Acta Pharmaceutica Sinica<br />

29(1): 48<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Catena J; Valls N; Bosch J; Bonjoch J<br />

The pummerer cyclization route to <strong>the</strong> ibophyllidine alkaloids - total syn<strong>the</strong>sis of (<br />

1994<br />

Tetrahedron Letters<br />

35(25): 4433-4436<br />

Abstract<br />

Pummerer cyclization of beta-aminoethyl sulfoxide 6 was effectively achieved using TFAA-TFA in<br />

toluene at 80 degrees C. The cyclized product 7 was <strong>the</strong>n converted to <strong>the</strong> alkaloid<br />

deethylibophyllidine. The required pyrrolo[3,2-c]carbazole 6 was prepared in five steps from 4-<br />

m e t h o x y p h e n e t h y l a m i n e .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Diez, A., J. Castells, P. Forns, M. Rubiralta, D. S. Grierson, H. P. Husson, X. Sola<br />

Syn<strong>the</strong>tic applications of 2-(1,3-dithian-2-yl)indoles .4. New syn<strong>the</strong>sis of <strong>the</strong> tetra<br />

1994<br />

Tetrahedron<br />

50(22): 6585-6602<br />

Abstract<br />

A new and versatile syn<strong>the</strong>sis of tetracyclic compounds 10, 22 and 24 presenting <strong>the</strong> ABED ring<br />

system of <strong>Strychnos</strong> alkaloids is described by closure of <strong>the</strong> C-1-C-11b bond in <strong>the</strong> key step. The<br />

intermediate tetrahydropyridinium salts 2 have been obtained from 2-(1,3-dithian-2-yl)indole (3) and<br />

ei<strong>the</strong>r 2-cyano-3-ethyl-1-methyl-1,2,3,6-tetrahydropyridine (4a) or N-substituted Delta(3)-piperidein-<br />

2 - o n e s ( 5 ) .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Gracia, J., N. Casamitjana, J. Bonjoch and J. Bosch<br />

Total syn<strong>the</strong>sis of uleine-type and Strycknos alkaloids through a common interme<br />

1994<br />

Journal of Organic Chemistry<br />

59(14): 3939-3951<br />

Abstract<br />

A stereoselective total syn<strong>the</strong>sis of <strong>the</strong> alkaloids of <strong>the</strong> uleine group, dasycarpidone, dasycarpidol,<br />

and nordasycarpidone, has been accomplished from <strong>the</strong> tetracyclic intermediate 1, which has been<br />

prepared by two alternative routes, ei<strong>the</strong>r by Fischer indolization of 2-azabicyclo[3.3.1]nonanone 9<br />

or, more efficiently, by stereocontrolled cyclization of 2-[(2-cyano-3-ethyl-4-piperidyl)methyl]i 24a<br />

and 24b. From <strong>the</strong> same tetracyclic intermediate 1, <strong>the</strong> <strong>Strychnos</strong> alkaloid tubotaiwine was also<br />

syn<strong>the</strong>sized, <strong>the</strong> key step being <strong>the</strong> construction of <strong>the</strong> quaternary spiranic center by cyclization of a<br />

t h i o n i u m i o n u p o n t h e i n d o l e b e t a - p o s i t i o n .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Kraus, G. A. and D. Bougie<br />

The preparation of a hexacyclic intermediate <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> alkaloi<br />

1994<br />

Tetrahedron<br />

50(9): 2681<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kuehne, M. E., C. S. Brook, D. A. Frasier and F. Xu<br />

Syn<strong>the</strong>ses of strychnos-type and aspidospermatan-type alkaloids .5. Total syn<strong>the</strong>se<br />

1994<br />

Journal of Organic Chemistry<br />

59(20): 5977-5982<br />

Abstract<br />

Intramolecular Diels-Alder reactions, at two stages in <strong>the</strong> reaction sequence, provided total syn<strong>the</strong>ses<br />

of <strong>the</strong> racemate of <strong>the</strong> hypotensive alkaloid echitamidine (8) and of its C-19,20 and C-20 epimers 9a<br />

a n d 9 b .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Kuehne, M. E., C. S. Brook, D. A. Frasier and F. Xu<br />

Syn<strong>the</strong>ses of strychnos- and aspidospermatan-type alkaloids. 5. Total syn<strong>the</strong>ses of<br />

1994<br />

Journal of Organic Chemistry<br />

59(20): 5977<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Kuehne, M. E., C. S. Brook, F. Xu and R. Parsons<br />

Total syn<strong>the</strong>ses of <strong>Strychnos</strong> alkaloids<br />

1994<br />

Pure and Applied Chemistry<br />

66(10/11): 2095<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kuehne, M. E., F. Xu and C. S. Brook<br />

Syn<strong>the</strong>ses of strychnos-type and aspidospermatan-type alkaloids .6. Total syn<strong>the</strong>se<br />

1994<br />

Journal of Organic Chemistry<br />

59(25): 7803-7806<br />

Abstract<br />

19-Oxodihydroakuammicine was obtained in a three-pot sequence, in 25% overall yield based on a<br />

new condensation-sigmatropic rearrangement sequence. Reductions-and quaternization reactions<br />

f u r n i s h e d t h e t i t l e c o m p o u n d s .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Mukherjee, R., B. C. Das, P. A. Keifer and J. N. Shoolery<br />

Structure and stereochemistry of divarine - ano<strong>the</strong>r new bisindole alkaloid from St<br />

1994<br />

Heterocycles<br />

38(9): 1965-1970<br />

Abstract<br />

The complete stereostructure of divarine, a new bisindole alkaloid from <strong>Strychnos</strong> divaricans<br />

Ducke., has been determined mainly by <strong>the</strong> use of one- and two-dimensional nmr techniques.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Prins, H. and J. A. Maghembe<br />

Germination studies on seed of fruit-trees indigenous to Malawi<br />

1994<br />

Forest Ecology and Management<br />

64(2-3): 111-125<br />

Abstract<br />

Indigenous fruit trees play an important role in rural areas in Malawi. However, in<strong>for</strong>mation on<br />

propagation techniques <strong>for</strong> <strong>the</strong>se species is scantily available. Freshly obtained seed of 16<br />

indigenous fruit trees and one exotic species were <strong>the</strong>re<strong>for</strong>e collected and tested <strong>for</strong> germination<br />

after applying eight different seed pretreatments. The pretreatments included direct sowing, washing,<br />

soaking, hot water treatment and different degrees of removal of <strong>the</strong> seedcoat. The objective was to<br />

find a simple technique to germinate seed of each species so that such a technique can be applied<br />

under village conditions in Malawi. - More than 80% germination was achieved <strong>for</strong> Bridelia<br />

cathartica, Bridelia micrantha, Diospyros mespili<strong>for</strong>mis, Parkia filicoidea, Piliostigma thonningii,<br />

<strong>Strychnos</strong> spinosa, Syzygium cordatum, Tamarindus indica, Uapaca kirkiana, Ziziphus abyssinica<br />

and Ziziphus mauritiana by simply cleaning and soaking <strong>the</strong> seeds. Quicker germination could be<br />

achieved by partial removal of <strong>the</strong> seedcoat <strong>for</strong> some species. Azanza garckeana and Parinari<br />

curatellifolia, however, required partial or complete removal of <strong>the</strong> seedcoat to achieve some<br />

germination. Flacourtia indica and Parinari curatellifolia had very poor germination of 20% and<br />

1 7 % , r e s p e c t i v e l y .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq, J., G. Dive, C. Delaude, R. Warin, R. Bassleer and L. Angenot<br />

2,7-dihydroxyapogeissoschizine from root bark of <strong>Strychnos</strong> gossweileri<br />

1994<br />

Phytochemistry<br />

35(2): 533-536<br />

Abstract<br />

In this paper, we describe <strong>the</strong> isolation and structural determination of 2,7-<br />

dihydroxyapogeissoschizine, a new alkaloid from <strong>the</strong> root bark of <strong>Strychnos</strong> gossweileri. Elucidation<br />

of its structure is based mainly on 1D and 2D NMR studies; its con<strong>for</strong>mation was optimized by<br />

energy minimization. According to a preliminary test, this substance shows low toxicity to B16<br />

melanoma cells, but not <strong>for</strong> non-cancer 3T3 fibroblasts cultured in vitro.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Rasoanaivo, P., S. Ratsimamanga-Urverg, R. Milijaona and H. Rafatro<br />

In vivo and in vitro chloroquine-potentiating action of <strong>Strychnos</strong> myrtoides alkaloi<br />

1994<br />

Planta Medica<br />

60(1): 13<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rasoanaivo, P., S. Ratsimamangaurverg, R. Milijaona, H. Rafatro, A. Rakotoratsi<br />

In-vitro and in-vivo chloroquine-potentiating action of <strong>Strychnos</strong> myrtoides alkalo<br />

1994<br />

Planta Medica<br />

60(1): 13-16<br />

Abstract<br />

Crude alkaloids of <strong>Strychnos</strong> myrtoides Gilg & Busse, empirically used as an adjuvant to<br />

chloroquine (CQ) in Malagasy herbal remedies, were practically devoid of intrinsic in vitro and in<br />

vivo antimalarial activity. However, when combined with CQ at a dose level much lower than <strong>the</strong>ir<br />

IC50 value, <strong>the</strong>y markedly enhanced in vitro <strong>the</strong> effectiveness of <strong>the</strong> syn<strong>the</strong>tic drug against a CQresistant<br />

strain of Plasmodium falciparum. They also enhanced in vivo CQ activity against a resistant<br />

strain of Plasmodium yoelii. By counter-current distribution (CCD) separation of <strong>the</strong> crude alkaloid<br />

extract, <strong>the</strong> two major alkaloids strychnobrasiline (1) and malagashanine (2), toge<strong>the</strong>r with four<br />

minor alkaloids, were isolated. Strychnobrasiline and malagashanine were devoid of both intrinsic<br />

antimalarial activity and cytotoxicity effect, but exhibited significant CQ-potentiating actions. These<br />

findings could account <strong>for</strong> <strong>the</strong> above-mentioned empirical use of S. myrtoides. The present state of<br />

research on antimalarial drug from <strong>Strychnos</strong> genus is also discussed.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rosenmund, P., M. Hosseinimerescht and C. Bub<br />

A simple entry into <strong>the</strong> series of tetracyclic heteroyohimbanes and secoyohimbane<br />

1994<br />

Liebigs Annalen Der Chemie<br />

(2): 151-158<br />

Abstract<br />

The divinylogous urethane 4a reacts in diluted acetic acid to give <strong>the</strong> indolochinolizine 9 (yield<br />

40%). The total amount grows up to 65%, if compound 14, prepared from 4a in nearly quantitative<br />

yield, is allowed to react with trifluoroacetic acid <strong>for</strong> a few minutes. Similarily, 4b and 4c give by<br />

treatment with SnCl2 and heat in an [4+2]-cycloaddition reaction <strong>the</strong> spiroindolines 17 and 18.<br />

Oxytryptamine reacts with 2 moles of 2 to give immediately <strong>the</strong> spirooxindole 21. This compound<br />

can be rearranged to give 23 (after treatment with acid, reduction and catalytic hydrogenation). 23<br />

h a s t h e c i s - c o n f i g u r a t i o n o f r h y n c o p h y l l i n e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Saka, J. D. K. and J. D. Msonthi<br />

Nutritional-value of edible fruits of indigenous wild trees in Malawi<br />

1994<br />

Forest Ecology and Management<br />

64(2-3): 245-248<br />

Abstract<br />

The edible portions of 16 edible wild fruits were analysed <strong>for</strong> moisture, protein, fat, crude fibre, ash<br />

and minerals (Ca, Mg, Fe, P, K, and Na). The total carbohydrate and energy contents were<br />

calculated. - Trichilia emetica, <strong>Strychnos</strong> spinosa, Azanza garckeana, Ximenia caffra and Parinari<br />

curatellifolia gave <strong>the</strong> highest levels of protein (17.0%), fat (31.2%), fibre (45.3%), ash (11.2%) and<br />

carbohydrate (88.2%), respectively. The highest and lowest energy values were found <strong>for</strong> <strong>Strychnos</strong><br />

spinosa (1923 kJ 100 g-1) and Azanza garckeana (810 kJ 100 g-1), respectively. Bauhinia thonningii<br />

af<strong>for</strong>ded <strong>the</strong> highest dry matter content (91.6%). - The highest contents of Ca, Mg, Fe, P, K and Na<br />

were found <strong>for</strong> Adansonia digitata (1156 mug g-1), Syzigium guineense (2247 mug g-1), Syzigium<br />

guineense (758 mug g-1), Trichilia emetica (3164 mug g-1), Ximenia caffra (41 79 1 mug g-1) and<br />

F l a c o u r t i a i n d i c a ( 5 8 9 m u g g - 1 ) , r e s p e c t i v e l y .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Saleh, N. A. M.<br />

Recent advances in <strong>the</strong> flavonoid chemistry of African plants<br />

1994<br />

Phytochemistry<br />

36(5): 1109-1115<br />

Abstract<br />

Recent reports of flavonoids from African plant species are reviewed with emphasis on newly<br />

described structures and including all <strong>the</strong> major flavonoid classes.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Wright, C. W., D. Allen, Y. Cai, Z. P. Chen, J. D. Phillipson, G. C. Kirby, D. C.<br />

Selective antiprotozoal activity of some <strong>Strychnos</strong> alkaloids<br />

1994<br />

Phyto<strong>the</strong>rapy Research<br />

8(3): 149-152<br />

Abstract<br />

The in vitro activities of 20 <strong>Strychnos</strong> alkaloids have been determined against three species of<br />

protozoa and <strong>the</strong> active compounds were <strong>the</strong>n assessed <strong>for</strong> in vitro cytotoxic activity using KB cells.<br />

3',4'-dihydrousambarensine was <strong>the</strong> most active against Plasmodium falciparum, and was relatively<br />

nontoxic to KB cells (cytotoxic/antiprotozoal ratio, 1474). Usambarensine displayed <strong>the</strong> most<br />

selectivity against Entamoeba histolytica while 3',4'-dihydrousambarensine was <strong>the</strong> most selective<br />

compound against Giardia intestinalis although <strong>the</strong> cytotoxicl antiprotozoal ratios (20.4 and 6.6<br />

respectively) were less favourable than <strong>the</strong> above.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Angle, S. R., J. M. Fevig, S. D. Knight and R. W. Marquis<br />

The aza-cope-mannich approach to <strong>Strychnos</strong> alkaloids. Short stereocontrolled tot<br />

1993<br />

Journal of <strong>the</strong> American Chemical Society<br />

115 (10): 3966<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Angle, S. R., J. M. Fevig, S. D. Knight, R. W. Marquis and L. E. Overman<br />

Syn<strong>the</strong>sis applications of cationic aza-cope rearrangements .24. The aza-cope-man<br />

1993<br />

Journal of <strong>the</strong> American Chemical Society<br />

115(10): 3966-3976<br />

Abstract<br />

A direct approach <strong>for</strong> <strong>the</strong> total syn<strong>the</strong>sis of <strong>Strychnos</strong> alkaloids has been developed. The key<br />

strategic element is <strong>the</strong> aza-Cope-Mannich rearrangement (Scheme II) of <strong>for</strong>maldiminium ions<br />

derived from azabicyclo[3.2.1]octanols 5 (Scheme I). This reorganization occurs with perfect<br />

stereochemical fidelity in high yield to <strong>for</strong>m <strong>the</strong> intricate skeleton of this complex alkaloid group.<br />

Critical to <strong>the</strong> success of this syn<strong>the</strong>sis endeavor was <strong>the</strong> evolution of an efficient sequence <strong>for</strong><br />

assembling <strong>the</strong> azabicyclo[3.2.1]octanol rearrangement substrates (Scheme V). Using a pivaloyl<br />

group to protect <strong>the</strong> nitrogen of <strong>the</strong> aromatic ring, we prepared <strong>the</strong> akuammicine degradation product<br />

(+/-)-dehydrotubifoline in 12 chemical operations and approximately 6% overall yield from 2-<br />

cyclopentenone (Schemes VI-VIII). A related sequence that employed a tert-butoxycarbonyl group<br />

to protect <strong>the</strong> aromatic nitrogen led to <strong>the</strong> syn<strong>the</strong>sis of <strong>the</strong> tetracyclic enecarbamate 63 (Scheme IX).<br />

Additional refinements of <strong>the</strong> aza-Cope-Mannich strategy allowed <strong>the</strong> total syn<strong>the</strong>sis of (+/-)-<br />

akuammicine to be accomplished by way of 10 isolated intermediates and in nearly 8% overall yield<br />

from 2-cyclopentenone (Scheme X). Notable features of this final sequence are (a) <strong>the</strong> convergent<br />

carbonylative coupling of vinylstannane 64 and aryl iodide 65 to af<strong>for</strong>d enone 66, (b) <strong>the</strong> use of <strong>the</strong><br />

1,3-dimethylhexahydro-2-oxo-1,3,5-triazine group to protect <strong>the</strong> primary aniline nitrogen, and (c) <strong>the</strong><br />

strategic use of an intramolecular epoxide aminolysis to assemble <strong>the</strong> azabicyclooctanol 71.<br />

Incorporation of oxidation at <strong>the</strong> terminal carbon of <strong>the</strong> ethylidene appendage should allow this total<br />

syn<strong>the</strong>sis approach to be extended to more complex <strong>Strychnos</strong> alkaloids such as strychnine.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Arbain, D., D. P. Putra and M. V. Sargent<br />

The alkaloids of Ophiorrhiza filistipula<br />

1993<br />

Australian Journal of Chemistry<br />

46(7): 977-985<br />

Abstract<br />

Extraction of <strong>the</strong> fresh leaves of Ophiorrhiza filistipula (Rubiaceae) has yielded <strong>the</strong> alkaloids<br />

normalindine (2), 7-methoxycampto<strong>the</strong>cin (6) and strictosidinic acid (11). The configurations of <strong>the</strong><br />

<strong>Strychnos</strong> alkaloids dolichantoside and isodolichantoside are revised.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Ban, Y.<br />

Total syn<strong>the</strong>ses of <strong>the</strong> natural-products from alkaloids to terpenes<br />

1993<br />

Journal of Syn<strong>the</strong>tic Organic Chemistry Japan<br />

51(2): 111-127<br />

Abstract<br />

This review describes <strong>the</strong> studies on <strong>the</strong> total syn<strong>the</strong>ses of <strong>the</strong> natural products, particularly alkaloids<br />

and terpenes, which involves <strong>the</strong> determination of absolute configurations of emetine, yohimbin and<br />

reserpine. It has been attempted in principle that <strong>the</strong> syn<strong>the</strong>sis should be developed by utilization of<br />

<strong>the</strong> new reactions originated in our own laboratory. The successful syn<strong>the</strong>ses are demonstrated by<br />

''one-step syn<strong>the</strong>sis of beta-carboline derivatives'', ''development of a new syn<strong>the</strong>tic method <strong>for</strong> 3,3-<br />

disubstituted oxindole derivatives, which method was extended to <strong>the</strong> syn<strong>the</strong>sis of various indole<br />

alkaloids through a common intermediate'', ''<strong>the</strong> total syn<strong>the</strong>sis of strychnos, aspidosperma and<br />

schizozygane alkaloids by photo-isomerization of 1-acylindole to 3-acylindolenine'', ''<strong>the</strong> crisscross<br />

annulation <strong>for</strong> syn<strong>the</strong>ses of heterocycles and <strong>the</strong> natural products'' and ''bis (trimethylsilyl enol e<strong>the</strong>r<br />

has been utilized as a 'masked acyl anion' <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of terpenses and <strong>the</strong> biologically active<br />

c y c l i c l a c t o n e s ' ' .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bennasar, M. L., E. Zulaica, J. M. Jimenez and J. Bosch<br />

Studies on <strong>the</strong> syn<strong>the</strong>sis of mavacurine-type indole alkaloids - 1st total syn<strong>the</strong>sis o<br />

1993<br />

Journal of Organic Chemistry<br />

58(27): 7756-7767<br />

Abstract<br />

Closure of <strong>the</strong> six-membered C ring of pentacyclic mavacurine-type alkaloids from suitably<br />

substituted tetracyclic substructures embodying rings ABDE of <strong>the</strong>se alkaloids, ei<strong>the</strong>r by<br />

electrophilic cyclization upon <strong>the</strong> indole 3-position or by intramolecular alkylation of <strong>the</strong> piperidine<br />

nitrogen, failed. In contrast, 6a-homopleiocarpamine (45) has been syn<strong>the</strong>sized from dithioacetal 42<br />

by an electrophilic cyclization involving <strong>the</strong> closure of <strong>the</strong> seven-membered C ring. The first total<br />

syn<strong>the</strong>sis of <strong>the</strong> alkaloid 2,7-dihydropleiocarpamine (68) has been achieved by photocyclization of<br />

<strong>the</strong> tetracyclic chloroacetamide 54 as <strong>the</strong> key step. The required tetracyclic ABDE ring systems were<br />

prepared by a straight<strong>for</strong>ward sequence consisting of nucleophilic addition of a 1-indoleacetatic ester<br />

enolate to <strong>the</strong> gamma position of a pyridinium salt, acid cyclization of <strong>the</strong> resulting 1,4-<br />

dihydropyridine, and final elaboration of <strong>the</strong> (E)-ethylidene substituent. An alternative syn<strong>the</strong>sis of<br />

<strong>the</strong> tetracyclic alkaloid vinoxine (10a) is also reported.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bonjoch, J., D. Sole and J. Bosch<br />

A new, general syn<strong>the</strong>tic pathway to strychnos indole alkaloids - 1st total syn<strong>the</strong>si<br />

1993<br />

Journal of <strong>the</strong> American Chemical Society<br />

115(5): 2064-2065<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch, J., D. Sole and J. Bosch<br />

Novel general and flexible method <strong>for</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> type indole alkaloid<br />

1993<br />

Anales De Quimica<br />

89(1): 113-114<br />

Abstract<br />

Starting from cis-3a-(o-nitrophenyl)octahydroindol-4-one (1), <strong>the</strong> pentacyclic <strong>Strychnos</strong> alkaloids<br />

tubifolidine and echitamidine were syn<strong>the</strong>sized in nine and twelve steps, respectively, <strong>the</strong> indole<br />

nucleus being <strong>for</strong>med in <strong>the</strong> last syn<strong>the</strong>tic steps by reductive cyclization of a tricyclic alpha-(on<br />

i t r o p h e n y l ) k e t o n e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Bonjoch, J., D. Sole and J. Bosch<br />

A new, general syn<strong>the</strong>tic pathway to strychnos indole alkaloids. First total syn<strong>the</strong>s<br />

1993<br />

Journal of <strong>the</strong> American Chemical Society<br />

115(5): 2064<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Dasilva, B. A., A. P. Dearaujo, R. Mukherjee and A. D. Chiappeta<br />

Bisnordihydrotoxiferine and vellosimine from <strong>Strychnos</strong> divaricans root - spasmol<br />

1993<br />

Phyto<strong>the</strong>rapy Research<br />

7(6): 419-424<br />

Abstract<br />

Bisnordihydrotoxiferine and vellosimine, two tertiary indole alkaloids have been isolated from <strong>the</strong><br />

root of <strong>Strychnos</strong> divaricans. Bisnordihydrotoxiferine antagonized in a nonspecific manner, oxytocin<br />

and acetylcholine induced contractions in <strong>the</strong> rat uterus and acetylcholine and histamine responses in<br />

<strong>the</strong> guinea-pig ileum. Bisnordihydrotoxiferine, like verapamil, produced effects on voltage<br />

dependent Ca2+ channels. For example in guinea-pig ileum, bisnordihydrotoxiferine (pD2' 3.92+/-<br />

0.09) and verapamil (pD2' 6.00+/-0.11) inhibited KCl induced contractions. Fur<strong>the</strong>rmore,<br />

bisnordihydrotoxiferine (pD2' 4.37+/-0.02) and verapamil (pD2 6.83+/-0.10) also antagonized CaCl2<br />

induced contractions of K+-depolarized rat uterus. When compared with sodium nitroprusside, an<br />

antagonist of receptor operated Ca2+ channels, bisnordihydrotoxiferine had no effect. However, in<br />

<strong>the</strong> aorta, <strong>the</strong> alkaloid (IC50, 6.10 X 10(-6) M) antagonized <strong>the</strong> intracellular calcium dependent<br />

transient contractions of noradrenaline and it was about four times more potent than procaine (IC50,<br />

2.30 x 10(-5) m), a known inhibitor of <strong>the</strong> release of Ca2+ from intracellular stores.<br />

Bisnordihydrotoxiferine may produce nonspecific spasmolytic actions mainly by inhibiting<br />

intracellular calcium mobilization and to a lesser extent by inhibiting voltage dependent calcium<br />

c h a n n e l s i n s m o o t h m u s c l e s .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Diez A; Vila C; Sinibaldi ME; Troin Y; Rubiralta M<br />

Syn<strong>the</strong>tic studies on indole alkaloids .6. Syn<strong>the</strong>sis of tetrahydroakuammicine and<br />

1993<br />

Tetrahedron Letters<br />

34(4): 733-736<br />

Abstract<br />

The syn<strong>the</strong>sis of dihydrocorynan<strong>the</strong>ol (5) and of <strong>the</strong> pentacyclic <strong>Strychnos</strong> alkaloid<br />

tetrahydroakuammicine (4) is reported from 5-ethyl-N-hydroxyethyl-2-(1-phenylsulfonyl-3-indolyl)-<br />

4-piperidineacetates (1) by means of a K(t)OBu/BF3.Et2O intramolecular cyclization.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Elmekkawy, S., M. R. Meselhy, Y. Kawata, S. Kadota, M. Hattori and T. Namba<br />

Metabolism of strychnine n-oxide and brucine n-oxide by human intestinal bacteri<br />

1993<br />

Planta Medica<br />

59(4): 347-350<br />

Abstract<br />

Anaerobic incubation of strychnine N-oxide with human intestinal bacteria resulted in its<br />

trans<strong>for</strong>mation to strychnine and 16-hydroxystrychnine. Similarly, brucine N-oxide was trans<strong>for</strong>med<br />

t o b r u c i n e a n d 1 6 - h y d r o x y b r u c i n e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Fritz, H., M. Soleymanijamarani, J. W. Bats and H. J. Teuber<br />

Syn<strong>the</strong>sis of <strong>the</strong> azocino[4.3-b]indole core structure of <strong>Strychnos</strong> alkaloids<br />

1993<br />

Liebigs Annalen Der Chemie<br />

(7): 705-710<br />

Abstract<br />

Michael addition of ethylmalonic dimethyl or diethyl ester with cyclohexenone and subsequent<br />

Fischer indole ring closure af<strong>for</strong>d <strong>the</strong> (tetrahydrocarbazolyl)malonic esters 4a-c. Decarboxylation of<br />

4a leads to <strong>the</strong> corresponding butyric acid methyl ester 5 which is oxidized by DDQ to <strong>the</strong> 4-oxo<br />

derivative 6a (byproduct: carbazole 7). Oximation of 6a to 8a and acylation of <strong>the</strong> oxime group to<br />

Ob, c as well as hydrogenation of this group yield 9a, b. Subsequent hydrogenation of <strong>the</strong><br />

tetrahydrocarbazole ring by means of borane/pyridine yields <strong>the</strong> hexahydrocarbazole derivatives 10a<br />

and b. By cyclisation in boiling o-xylene (sodium hydride catalysis) 10a is converted into <strong>the</strong><br />

tetracyclic 1,5-methanoazocino[4.3-b]indole derivative 11a with an alkaloid analogous ethyl side<br />

chain. The X-ray structural analysis of <strong>the</strong> corresponding phenylsulfonyl derivative 11b confirms<br />

constitution and stereochemistry. As a diastereoisomer of 11a <strong>the</strong> byproduct 11c could be isolated.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Magnus P; Giles M<br />

A new approach to <strong>the</strong> syn<strong>the</strong>sis of <strong>the</strong> <strong>Strychnos</strong> alkaloids core structure<br />

1993<br />

Tetrahedron Letters<br />

34(40): 6355<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Parsons, R. L., J. D. Berk and M. E. Kuehne<br />

Total syn<strong>the</strong>ses of strychnan-type and aspidospermatan-type alkaloids .2. Generati<br />

1993<br />

Journal of Organic Chemistry<br />

58(26): 7482-7489<br />

Abstract<br />

The syn<strong>the</strong>sis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25)<br />

provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate<br />

(12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-<br />

carboxylate (9), potential intermediates <strong>for</strong> <strong>the</strong> syn<strong>the</strong>ses of strychnos alkaloids. A new condensationsigmatropic<br />

rearrangement reaction gives <strong>the</strong> tetracyclic product 9 directly from <strong>the</strong> tryptamine 25.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Parsons, R. L., J. D. Berk and M. E. Kuehne<br />

Intermediates <strong>for</strong> <strong>Strychnos</strong> alkaloids<br />

1993<br />

Abstracts of Papers of <strong>the</strong> American Chemical Society<br />

205(Mar): 186<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq, J., B. Bouzahzah, A. Pons, R. Greimers, L. Angenot, R. Bassleer a<br />

Strychnopentamine, a potential anticancer agent.<br />

1993<br />

Planta Medica<br />

59(1): 59-62<br />

Abstract<br />

We analysed <strong>the</strong> effects of strychnopentamine, an alkaloid isolated from <strong>Strychnos</strong> usambarensis, on<br />

an Ehrlich ascites tumor growing in <strong>the</strong> mouse after inoculation. Four subcutaneous injections of 1. 5<br />

mg strychnopentamine (1 per day) induce a significant decrease of <strong>the</strong> number of tumor cells and a<br />

significant increase of <strong>the</strong> survival of <strong>the</strong> treated mice. Observed side effects are partial haemolysis<br />

a n d s o m e l i v e r d a m a g e .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Rawal, V. H., C. Michoud and R. F. Monestel<br />

General strategy <strong>for</strong> <strong>the</strong> stereocontrolled syn<strong>the</strong>sis of strychnos alkaloids - a conci<br />

1993<br />

Journal of <strong>the</strong> American Chemical Society<br />

115(7): 3030-3031<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Solis, P. N., C. W. Wright, M. P. Gupta and J. D. Phillipson<br />

Alkaloids from Cephaelis dichroa<br />

1993<br />

Phytochemistry<br />

33(5): 1117-1119<br />

Abstract<br />

A new indole alkaloid, vallesiachotamine lactone, and four known compounds strictosidine,<br />

strictosamide, vallesiachotamine and angustine were isolated from <strong>the</strong> aerial parts of Cephaelis<br />

dichroa. Structures were established by spectroscopic methods (UV, IR, mass spectrometry, H-1 and<br />

C-13 NMR, including COSY 45 and H-1-C-13 heterocorrelation). Isovallesiachotamine was detected<br />

as a degradation product of vallesiachotamine.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Tchamba, M. N. and P. M. Seme<br />

Diet and feeding-behavior of <strong>the</strong> <strong>for</strong>est elephant in <strong>the</strong> Santchou Reserve, Camero<br />

1993<br />

African Journal of Ecology<br />

31(2): 165-171<br />

Abstract<br />

This study reports <strong>the</strong> diet and feeding behaviour of <strong>for</strong>est elephants in Western Cameroon. Diet<br />

consisted primarily of grass (Pennisetum purpureum). Woody material (leaves and stems) made up<br />

<strong>the</strong> smallest proportion of <strong>the</strong> diet. Twenty-two species of fruit were eaten of which seven <strong>for</strong>med a<br />

significant component of <strong>the</strong> diet: Cucurmis manii, Desplatsia subericarpa, Irvingia gabonensis,<br />

Parinari excelsa, <strong>Strychnos</strong> innocuea, Theobroma cacao and Vitex doniana. The greatest variety of<br />

fruit was available during <strong>the</strong> dry season. The frequent presence of crop seeds in <strong>the</strong> dung piles<br />

indicated that elephant incursions into <strong>the</strong> farms to feed on crops were regular. Elephants removed<br />

bark from eight species of tree but concentrated on four: Afzelia bipindensis, Coloncoba welwitschii,<br />

Bridelia ferruginea and Terminalia superba. Seventeen species were recorded as browsed. Trees in<br />

particular were favoured. Elephants fed mainly by grazing or stripping off fruits. Debarking of trees,<br />

breaking of <strong>the</strong> main stems, and uprooting or pushing over were minor feeding activities.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Vanveenendaal, W. L. H. and R. W. Denouter<br />

Development of included phloem and organization of <strong>the</strong> phloem network in <strong>the</strong> st<br />

1993<br />

Iawa Journal<br />

14(3): 253-265<br />

Abstract<br />

The development of <strong>the</strong> diffuse included phloem strands in <strong>Strychnos</strong> millepunctata Leeuwenberg is<br />

described and compared with that in some o<strong>the</strong>r <strong>Strychnos</strong> species. - The phloem strands are<br />

produced outwards by small segments of <strong>the</strong> vascular cambium which function differently. In <strong>the</strong>se<br />

segments <strong>the</strong> secondary xylem production inwards is retarted and gradually stops, <strong>the</strong> secondary<br />

phloem production outwards increases. Thus <strong>the</strong> vascular cambium cylinder <strong>for</strong>ms depressions.<br />

These cambium segments become detached from <strong>the</strong> rest of <strong>the</strong> vascular cambium. The future strand<br />

sinks into <strong>the</strong> secondary xylem and is bridged over by a complementary cambium which is <strong>for</strong>med in<br />

<strong>the</strong> outer border of <strong>the</strong> strand and joins <strong>the</strong> vascular cambial cylinder. The complementary cambium<br />

now starts with <strong>the</strong> production of secondary xylem inwards and secondary phloem outwards like <strong>the</strong><br />

rest of <strong>the</strong> vascular cambium in die once more closed cambial cylinder. - The composition of <strong>the</strong><br />

secondary phloem in <strong>the</strong> strands is different from both <strong>the</strong> secondary and primary external phloem<br />

(phloem outside <strong>the</strong> cylinder of vascular cambium). Radial rows of cells are present within <strong>the</strong><br />

included phloem strands which continue into <strong>the</strong> later <strong>for</strong>med secondary xylem. One- to five-seriate<br />

rays traverse <strong>the</strong> strands. The embedded cambial segment near <strong>the</strong> inner border of <strong>the</strong> strand<br />

remains active. The crushing of <strong>the</strong> phloem takes place near <strong>the</strong> outer border Of <strong>the</strong> strand, <strong>for</strong>ming<br />

cap-like tissues of disorganised cells. Internal phloem is regularly renewed by cambial activity. The<br />

internal cambium produces secondary phloem inwards. The composition of this phloem resembles<br />

that of <strong>the</strong> included phloem strands. - Inter-connections between included phloem strands, as well as<br />

anastomoses of <strong>the</strong>se strands with both secondary external and internal phloem, has been<br />

demonstrated. Toge<strong>the</strong>r <strong>the</strong>se three phloem types <strong>for</strong>m a three-dimensional secondary phloem<br />

n e t w o r k .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Amat, M. and J. Bosch<br />

Studies on <strong>the</strong> syn<strong>the</strong>sis of pentacyclic <strong>Strychnos</strong> indole alkaloids - closure of e-ri<br />

1992<br />

Journal of Organic Chemistry<br />

57(21): 5792-5796<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Arbain, D., N. H. Lajis, D. P. Putra, M. V. Sargent, B. W. Skelton and A. H. Whit<br />

New quaternary corynan<strong>the</strong> alkaloid from Lerchea bracteata<br />

1992<br />

Journal of <strong>the</strong> Chemical Society-Perkin Transactions 1<br />

(22): 3039-3042<br />

Abstract<br />

Extraction of <strong>the</strong> leaves of Lerchea bracteata Val. (Rubiaceae) has yielded a quaternary Corynan<strong>the</strong><br />

alkaloid, dihydro-3-epi-corynan<strong>the</strong>ol methochloride (lercheine) 4 <strong>the</strong> structure of which followed<br />

from analysis of its spectral data and by X-ray crystal structure determination of <strong>the</strong> corresponding<br />

b r o m i d e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Balakrishna, P. and A. Raman<br />

Cecidogenesis of leaf galls of <strong>Strychnos</strong> nux vomica (Loganiaceae) induced by th<br />

1992<br />

Entomologia Generalis<br />

17(4): 285-292<br />

Abstract<br />

Diaphorina truncata Craw<strong>for</strong>d 1924 induces roll galls on <strong>the</strong> leaves of <strong>Strychnos</strong> nux-vomica<br />

Linnaeus (Loganiaceae) in <strong>the</strong> W' coastal plains of S' India. Gravid females of D. truncata colonise<br />

and oviposit on <strong>the</strong> abaxial surfaces of differentiated leaves of S. nux-vomica. Feeding activity of <strong>the</strong><br />

first instar larvae on <strong>the</strong> mesophyll tissue initiates gall development, evident as wrinkles. In 10-12<br />

days, with <strong>the</strong> growth of <strong>the</strong> inhabiting larvae, <strong>the</strong> leaf turns more-intensely curled. Mature larvae<br />

feed on <strong>the</strong> phloem strands and consequently <strong>the</strong> vasculature of <strong>the</strong> galled leaf breaks down. In 25-30<br />

days, <strong>the</strong> leaf crumples due to distortion of cells and desiccation, and <strong>the</strong> galled leaf abscises,<br />

synchronising with <strong>the</strong> moulting of <strong>the</strong> L5 into adults. To supplement <strong>the</strong>se observations, changes in<br />

<strong>the</strong> primary and some secondary plant metabolites of <strong>the</strong> host leaf during cecidogenesis have been<br />

estimated. These changes are related to <strong>the</strong> nutrition and biology of <strong>the</strong> psyllid species.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bisset, N. G.<br />

War and hunting poisons of <strong>the</strong> new-world .1. Notes on <strong>the</strong> early history of curare<br />

1992<br />

Journal of Ethnopharmacology<br />

36(1): 1-26<br />

Abstract<br />

The history to about 1850 of <strong>the</strong> muscle-relaxant poison curare is discussed, especially <strong>the</strong><br />

developments leading to <strong>the</strong> botanical identification of <strong>the</strong> plants that yield <strong>the</strong> alkaloidal active<br />

principles: Loganiaceae (<strong>Strychnos</strong> species) and Menispermaceae (Abuta. Chondrodendron, and<br />

Curarea species). One of <strong>the</strong> earliest encounters with <strong>the</strong> poison appears to have been during <strong>the</strong><br />

exploration of <strong>the</strong> Lake Maracaibo region in Colombia by Alonso Perez de Tolosa in 1548. It is<br />

pointed out (yet again) that Sir Walter Ralegh did not bring back <strong>the</strong> poison to Europe in 1595 and<br />

that it was Keymis who first came across <strong>the</strong> word ourari when exploring <strong>the</strong> lower reaches of <strong>the</strong><br />

Orinoco in 1596. Gumilla, La Condamine, Ulloa, Veigl, and o<strong>the</strong>rs gave much additional<br />

in<strong>for</strong>mation about <strong>the</strong> poison during <strong>the</strong> 18th century. Scientific studies began in <strong>the</strong> latter part of <strong>the</strong><br />

century when Schreber listed <strong>the</strong> botanical identities of four of <strong>the</strong> plant components entering into<br />

<strong>the</strong> curare prepared by <strong>the</strong> Akawai Indians of Surinam. As far as is known, none of <strong>the</strong>se people<br />

actually saw curare being made. Thereafter, progress was rapid. Humboldt and Bonpland were <strong>the</strong><br />

first trained scientists to witness <strong>the</strong> preparation of <strong>the</strong> poison, at <strong>the</strong> very beginning of <strong>the</strong> 19th<br />

century. Subsequent exploration by Martius and Spix, Poeppig, Youd, <strong>the</strong> Schomburgk bro<strong>the</strong>rs, De<br />

Castelnau and Deville, Spruce, and o<strong>the</strong>rs, up to <strong>the</strong> middle of <strong>the</strong> century, extended and deepened<br />

botanical and ethnological knowledge of curare. Study of its physiology started at about that time<br />

with <strong>the</strong> classical experiments of Rudolf von Koelliker and Claude Bernard.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Casamitjana N; Gracia J; Bonjoch J; Bosch J<br />

Functionalized 2-azabicyclo[3.3.1]nonanes .16. Studies on <strong>the</strong> syn<strong>the</strong>sis of strych<br />

1992<br />

Tetrahedron Letters<br />

33(15): 2055-2058<br />

Abstract<br />

A stereocontrolled four-step syn<strong>the</strong>sis of polysubstituted functionalized morphans 7 and 8 from <strong>the</strong><br />

3,4-cis piperidine derivative 1 is reported. beta-Keto ester 1 was converted to 4-<br />

(oxopentyl)piperidines 3, and <strong>the</strong>n to <strong>the</strong> 2-cyano derivatives 4 and 5, which were cyclized to <strong>the</strong><br />

t i t l e c o m p o u n d s 7 a n d 8 .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Dutta, G. R. and A. K. Roy<br />

Mycobial deterioration in strychnine and brucine of <strong>Strychnos</strong> nux vomica seed<br />

1992<br />

Indian Phytopathology<br />

45(1), 77<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Gasquet, M., J. Quetinleclercq, P. Timondavid, G. Balansard and L. Angenot<br />

Antiparasitic properties of diploceline, a quaternary alkaloid from <strong>Strychnos</strong> goss<br />

1992<br />

Planta Medica<br />

58(3): 276-277<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kopp, B., W. P. Bauer and A. Bernkopschnurch<br />

Analysis of some malaysian dart poisons<br />

1992<br />

Journal of Ethnopharmacology<br />

36(1): 57-62<br />

Abstract<br />

An investigation of nine Malaysian dart poisons has confirmed that <strong>the</strong>ir main active components are<br />

cardenolides from Antiaris toxicaria (Pers.) Lesch. and alkaloids probably from different <strong>for</strong>ms of<br />

<strong>Strychnos</strong> ignatii P. Bergius. It is not possible to determine <strong>the</strong> ethnic origin of <strong>the</strong> poisons from <strong>the</strong><br />

results of <strong>the</strong> analyses on <strong>the</strong>ir own. Two new cardiac glycosides have been isolated and <strong>the</strong>ir<br />

structures determined as 12-beta-hydroxycannogenin 3-beta-O-beta-D-deoxygulopyranoside and 3-<br />

b eta-O-alpha-L-rhamnopyranoside, respectively.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kraus, G. A. and D. Bougie<br />

The preparation of a hexacyclic intermediate <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> alkaloi<br />

1992<br />

Synlett<br />

(4): 279-280<br />

Abstract<br />

The hexacyclic ring system, indolizino[7,8,8a,1-bcd]-pyrido[1,2,3-lm]carbazolone 10 has been<br />

syn<strong>the</strong>sized in nine steps from <strong>the</strong> pyrido[3,2,1-jk]carbazolylethanal 3. Key steps include <strong>the</strong><br />

selective reduction of aldehyde 3, <strong>the</strong> stereoselective introduction of an allyl unit via <strong>the</strong> Sakurai<br />

reaction and <strong>the</strong> ozonolysis/dehydrative cyclization to af<strong>for</strong>d bridgehead enamine 10.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Magnus, P., N. L. Sear, C. S. Kim and N. Vicker<br />

Studies on <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> alkaloids - a new entry into <strong>the</strong> azocino[4,3-<br />

1992<br />

Journal of Organic Chemistry<br />

57(1): 70-78<br />

Abstract<br />

Treatment of cyclohexanone-3-acetic acid with phenylhydrazine hydrochloride gave <strong>the</strong><br />

tetrahydrocarbazole 7 (73%). The derived methyl ester 8 (99.6%) was oxidized to <strong>the</strong> 4-oxo<br />

compound 9 in 85% yield by treatment with DDQ/90% aqueous THF at 0-degrees-C. Treatment of<br />

9 with NaH/DMF at 0-degrees-C followed by (p-methoxyphenyl)sulfonyl chloride gave 10 (81%).<br />

Hydrolysis of 10 using lithium hydroxide in aqueous THF gave <strong>the</strong> acid 11 (86%). The acid 11 was<br />

converted into <strong>the</strong> amide 12 by treatment with ethylchloro<strong>for</strong>mate/NEt3/CH2Cl2 followed by<br />

aqueous NH4OH. The ketoamide 12 was exposed to NaBH4/MeOH/THF to give a single alcohol<br />

13 (> 95%). Exposure of 13 to trifluoroacetic acid (cat)/CH2Cl2/0-20-degrees-C gave <strong>the</strong><br />

azocino[4.3-b]indole core tetracyclic lactam 14 (90%). The amide 14 was reduced (BH3.THF) to<br />

give 21, which was directly acetylated (PhSCH2COCl) to give exocyclic amide 22. All attempts to<br />

close <strong>the</strong> C11-C12 bond only resulted in decomposition. Treatment of <strong>the</strong> acid 11 with<br />

EtO2CCl/Et3N followed by [2-(phenylthio)ethyl]amine gave <strong>the</strong> amide 24 (90%). Reduction of 24<br />

using NaBH4 gave <strong>the</strong> alcohol 25 which upon exposure to CF3CO2H at room temperature cyclized<br />

to <strong>the</strong> tetracyclic amide 26 (96% overall). Oxidation of <strong>the</strong> sulfide 26 (m-CPBA) resulted in <strong>the</strong><br />

diastereomeric sulfoxides 28. When <strong>the</strong> sulfoxides 28 were exposed to Pummerer conditions <strong>the</strong><br />

only products that could be isolated were <strong>the</strong> (E)- and (Z)-vinyl sulfides 29 (72% and 25%,<br />

respectively). Similarly <strong>the</strong> dimethylthio acetal 33 was converted into <strong>the</strong> aldehyde 34 (100%).<br />

Treatment of 26 with POCl3/DMF gave 35 (90.8%) which was exposed to<br />

PhNHNH2/AcOH/AcONa to give <strong>the</strong> pyrazole 36 (85%). Attempts to close <strong>the</strong> E-ring via<br />

sulfoxides derived from ei<strong>the</strong>r <strong>the</strong> pyrazole 36 or <strong>the</strong> oxazole 37 were unsuccessful. Treatment of<br />

<strong>the</strong> chloride 40 with KH/HN(SiMe3)2 in toluene resulted in a slow conversion into <strong>the</strong> 3-oxindole<br />

4 4 .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Massiot, G., P. Thepenier, M. J. Jacouier, L. Lemenolivier and C. Delaude<br />

Alkaloids from roots of <strong>Strychnos</strong> potatorum<br />

1992<br />

Phytochemistry<br />

31(8): 2873-2876<br />

Abstract<br />

Twenty-four compounds have been isolated and identified in <strong>the</strong> root bark of <strong>Strychnos</strong> potatorum.<br />

They are: Harmane carboxamide, cantleyine, 18,19-dihydrousambarensine, polyneuridine,<br />

norharmane, akuammidine, nor-C-flurorocurarine, ochrolifuanine A, bisnordihydrotoxiferine,<br />

ochrolifuanine E, normacusine B, normavacurine, henningsamine, 11-methoxyhenningsamine,<br />

dihydrolongicaudatine, dihydrolongicaudatine Y, antirhine, (20R)- and (20S)-dihydroantirhine, 11-<br />

methoxy-12-hydroxydiaboline, diaboline, 11-methoxydiaboline, desacetylretuline and diaboline N-<br />

o x i d e . T h e a l k a l o i d s i n i t a l i c a r e n o v e l .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Mukherjee R<br />

Indole alkaloids of <strong>Strychnos</strong> from <strong>the</strong> nor<strong>the</strong>ast of Brazil<br />

1992<br />

Traditional medicine, Calcutta; India<br />

New Delhi, 229-234 pp<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Pan, S. K.<br />

A study of anti-timira (anticataract) activity of katak (<strong>Strychnos</strong> potatorum)<br />

1992<br />

International Ayurveda conference; Musing ayurved, Pune, India<br />

Delhi, 129-138 pp<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq, J., C. Coune, C. Delaude, R. Warin, R. Bassleer and L. Angenot<br />

Revision of <strong>the</strong> structure of strychnofluorine, an alkaloid of <strong>Strychnos</strong> gossweileri<br />

1992<br />

Phytochemistry<br />

31(12): 4347-4349<br />

Abstract<br />

The structure of strychnofluorine, an indole alkaloid isolated from <strong>the</strong> root bark of <strong>Strychnos</strong><br />

gossweileri has been revised. Strychnofluorine proved to be identical with 18-<br />

hydroxynorfluorocurarine. Fur<strong>the</strong>rmore, it has a low cytotoxic activity on B16 melanoma cells.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Thomas, G., M. D. F. M. Diniz and R. Mukherjee<br />

Fur<strong>the</strong>r-studies on <strong>the</strong> antidiarrheal activity of bisnordihydrotoxiferine, a tertiary i<br />

1992<br />

Phyto<strong>the</strong>rapy Research<br />

6 (2): 84-88<br />

Abstract<br />

The dimeric tertiary indole alkaloid bisnordihydrotoxiferine isolated from <strong>the</strong> root bark of <strong>Strychnos</strong><br />

trinervis (Vell.) Mart. inhibited, on i.p. administration, Escherichia coli-induced diarrhoea and<br />

cholera toxin-stimulated intestinal fluid accumulation in mice. The respective ED50 values were<br />

10.6 and 20.0 mg/kg. The activity of bisnordihydrotoxiferine was unaffected by nalorphine or<br />

yohimbine, suggesting that <strong>the</strong> opioid and alpha-2-adrenoceptors respectively, are not important <strong>for</strong><br />

its antidiarrhoeal action. In smooth muscle studies, bisnordihydrotoxiferine antagonized in a<br />

noncompetitive and reversible manner, <strong>the</strong> contractions produced by histamine, acetylcholine and<br />

substance P in guinea-pig ileum and by 5-hydroxytryptamine and arachidonic acid in rat fundic strip.<br />

The respective pD2' values (mean +/- SEM) were 5.21 +/- 0.29, 5.20 +/- 0.29, 5.35 +/- 0.12, in <strong>the</strong><br />

ileum and 4.95 +/- 0.13 and 3.66 +/- 0.12 in <strong>the</strong> fundic strip. The values of slopes of <strong>the</strong> regression<br />

lines differed significantly from unity in all cases. Bisnor was inactive against PGE2-induced<br />

contractions in <strong>the</strong> ileum. The mechanism of action of <strong>the</strong> alkaloid may be related to nonspecific<br />

antagonism of gastrointestinal smooth muscle stimulant activity of several endogenous substances.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch, J., J. Quirante, D. Sole, J. Castells, M. Galceran and J. Bosch<br />

Functionalized 2-azabicyclo(3.3.1)nonanes .14. 8-aryl-2-azabicyclo[3.3.1]nonan-7<br />

1991<br />

Tetrahedron<br />

47(25): 4417-4428<br />

Abstract<br />

The syn<strong>the</strong>sis of 8-aryl-2-azabicyclo[3.3.1]nonan-7-ones (7) by acid cyclization of 4-(3-aryl-2-<br />

oxopropyl)-2-piperidinecarbonitriles (5) is reported. Bicyclic alpha-aril-beta-amino ketones 7 easily<br />

undergo a retro-Michael ring opening to give <strong>the</strong> corresponding 2-arylcyclohexenones 8.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bosch, J., M. Salas, M. Amat, M. Alvarez, I. Morgo and B. Adrover<br />

Studies on <strong>the</strong> syn<strong>the</strong>sis of <strong>Strychnos</strong> indole alkaloids<br />

1991<br />

Tetrahedron<br />

47(28): 5269-5276<br />

Abstract<br />

Tetracycles 3b-d, having <strong>the</strong> ABCD ring substructure of <strong>Strychnos</strong> alkaloids and a N(b)-<br />

(<strong>for</strong>mylmethyl) substituent protected as an oxime or hydrazone derivative, have been prepared by<br />

nucleophilic addition of <strong>the</strong> enolate of indoleacetic ester 1 to pyridinium salts 2b-d followed by acid<br />

cyclization. The same one-pot, two-step sequence allowed <strong>the</strong> preparation of tetracycle 3f, which<br />

incorporates an alpha-methoxyacrylate chain at <strong>the</strong> piperidine beta-position.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Burger BV; Petersen WGB<br />

Semiochemicals of <strong>the</strong> Scarabaeinae .3. Identification of <strong>the</strong> attractant <strong>for</strong> <strong>the</strong> dun<br />

1991<br />

Zeitschrift Fur Natur<strong>for</strong>schung C-a Journal of Biosciences<br />

46(11-12): 1073-1079<br />

Abstract<br />

Following <strong>the</strong> observation that <strong>the</strong> non-ball-rolling dung beetle Pachylomerus femoralis (Kirby)<br />

rolled <strong>the</strong> flesh-covered seeds from <strong>the</strong> fruit of <strong>the</strong> spineless monkey orange tree, <strong>Strychnos</strong><br />

madagascariensis Poiret, an investigation into <strong>the</strong> chemical attractants of this fruit was made. Using<br />

headspace gas chromatography with electroantennographic and flame ionization detection in<br />

parallel, followed by GC-MS analysis, 1-butanol, methyl butanoate, ethyl 2-methylpropanoate, ethyl<br />

butanoate, butyl ethanoate, ethyl 2-methylbutanoate, propyl butanoate, butyl propanoate, methyl<br />

hexanoate, butyl 2-methylpropanoate, and butyl butanoate were identified as <strong>the</strong> constituents of <strong>the</strong><br />

attractant. It was found that P. femoralis beetles were attracted to a mixture of <strong>the</strong> syn<strong>the</strong>tic<br />

compounds about as strongly as to <strong>the</strong> fresh fruit. The beetles were also equally attracted to <strong>the</strong> fruit<br />

and to horse dung in areas where ripe fruit was not available. In areas permeated with <strong>the</strong> smell of<br />

<strong>the</strong> ripe fruit <strong>the</strong> horse dung retained its attractiveness, whereas no beetles were caught in traps<br />

b a i t e d w i t h f r u i t .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

De, B. and N. G. Bisset<br />

Separation of <strong>Strychnos</strong> nux vomica alkaloids by high-per<strong>for</strong>mance liquid-chroma<br />

1991<br />

Journal of Chromatography<br />

587(2): 318-320<br />

Abstract<br />

The common alkaloids present in <strong>Strychnos</strong> nux-vomica L. were separated using normal-phase highp<br />

e r f o r m a n c e l i q u i d c h r o m a t o g r a p h y .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Demedeiros, C. L. C., G. Thomas and R. Mukherjee<br />

The source of ca2+ <strong>for</strong> <strong>the</strong> spasmolytic actions of longicaudatine, a bisindole alkal<br />

1991<br />

Phyto<strong>the</strong>rapy Research<br />

5(1): 24-28<br />

Abstract<br />

Longicaudatine, a tertiary bisindole alkaloid isolated from <strong>the</strong> root bark of <strong>Strychnos</strong> trinervis (Vell.)<br />

Mart. (Loganiaceae), antagonized in a noncompetitive manner, carbachol and histamine induced<br />

contractions of <strong>the</strong> guinea-pig ileum and bradykinin responses in <strong>the</strong> rat uterus. The respective pD2'<br />

values (mean +/- SE) were 4.61 +/- 0.21, 4.98 +/- 0.04 and 4.49 +/- 0.01. Longicaudatine, unlike<br />

verapamil, had no effect on voltage dependent Ca2+ channels, as it failed to inhibit KCl or CaCl2<br />

induced contractions of guinea-pig ileum and depolarized rat uterus respectively. When compared<br />

with sodium nitroprusside, an antagonist of receptor operated Ca2+ channels, longicaudatine<br />

produced a slower and weaker inhibition of noradrenaline induced sustained contractions of rabbit<br />

aortic strips. However, in <strong>the</strong> aorta, <strong>the</strong> alkaloid antagonized <strong>the</strong> intracellular calcium dependent<br />

transient contractions of noradrenaline and longicaudatine (IC50, 5.01 x 10(-7) M) was<br />

approximately 133 times more potent that procaine (IC50, 6.68 x 10(-5) M), a known inhibitor of <strong>the</strong><br />

release of Ca2+ from intracellular stores. Longicaudatine may exert nonspecific spasmolytic effects<br />

by acting on intracellular Ca2+ stores, ra<strong>the</strong>r than on depolarization dependent or receptor operated<br />

C a 2 + c h a n n e l s .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Fevig, J. M., R. W. Marquis and L. E. Overman<br />

Syn<strong>the</strong>sis applications of cationic aza-cope rearrangements .22. New approach to<br />

1991<br />

Journal of <strong>the</strong> American Chemical Society<br />

113(13): 5085-5086<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Gracia, J., J. Bonjoch, N. Casamitjana, M. Amat and J. Bosch<br />

Total syn<strong>the</strong>sis of <strong>the</strong> <strong>Strychnos</strong> alkaloid tubotaiwine<br />

1991<br />

Journal of <strong>the</strong> Chemical Society-Chemical Communications<br />

(9): 614-615<br />

Abstract<br />

The total syn<strong>the</strong>sis of racemic tubotaiwine 8 has been achieved from <strong>the</strong> tetracyclic intermediate 1,<br />

<strong>the</strong> key steps being <strong>the</strong> construction of <strong>the</strong> C(7)-quaternary centre by cyclization of a thionium ion<br />

upon <strong>the</strong> indole 3-position and <strong>the</strong> introduction of <strong>the</strong> C(16)-methoxycarbonyl substituent by<br />

p hotochemical rearrangement of <strong>the</strong> N-methoxycarbonyleamine 7.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Jhansi, P., T. P. Kalpana and C. G. K. Ramanujam<br />

Pollen analysis of rock bee summer honeys from <strong>the</strong> Prakasam district of <strong>the</strong> And<br />

1991<br />

Journal of Apicultural Research<br />

30(1): 33-40<br />

Abstract<br />

The paper deals with <strong>the</strong> pollen analysis of six squeezed honey samples collected from rock bee<br />

(Apis dorsata) combs during <strong>the</strong> period 1982-1984. All <strong>the</strong> samples represented summer honeys<br />

from tropical dry deciduous <strong>for</strong>est tracts of <strong>the</strong> Prakasam district of Andhra Pradesh, India. The<br />

samples, which were all multifloral, contained a total of 57 pollen types. The results indicate that<br />

Cassia fistula, Terminalia alata, Bauhinia racemosa, Feronia elephantum, Lagerstroemia parviflora,<br />

<strong>Strychnos</strong> potatorum, Zizyphus xylopyrus, Phyllanthus sp., Soymida febrifuga, Syzygium cumini,<br />

Dalbergia latifolia and Caesalpinia bonduc constitute fairly reliable nectar sources <strong>for</strong> honey bees in<br />

t h i s a r e a d u r i n g t h e s u m m e r .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Kuehne, M. E., D. A. Frasier and T. D. Spitzer<br />

Total syn<strong>the</strong>ses of tubotaiwine and 19,20-dihydro-20-epi-akuammicine<br />

1991<br />

Journal of Organic Chemistry<br />

56(8): 2696-2700<br />

Abstract<br />

Starting from <strong>the</strong> indoloazepine 9, <strong>the</strong> title products 2 and 7 were syn<strong>the</strong>sized in seven steps in 27<br />

a n d 2 2 % o v e r a l l y i e l d s , r e s p e c t i v e l y .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Massiot, G., P. Thepenier, M. J. Jacquier, J. Henin, L. Lemenolivier and C. Delau<br />

Alkaloids from Dtrychnos henningsii<br />

1991<br />

Phytochemistry<br />

30(10): 3449-3456<br />

Abstract<br />

Seventeen alkaloids have been isolated from <strong>the</strong> leaves, stem and root barks of <strong>Strychnos</strong> henningsii<br />

collected in Tanzania. They are holstiine, splendoline, 23-hydroxyspermostrychnine, 19-epi-23-<br />

hydroxyspermostrychnine, retuline, henningsiine, deshydroxyacetylhenningsiine, O-<br />

acetylhenningsiine, 3-hydroxyhenningsiine, henningsiine-N(4)-oxide, 23-hydroxyspermostrychnine-<br />

N(4)-oxide, 17,23-dihydroxyspermostrychnine, spermostrychnine, henningsamide, O-<br />

acetylhenningsamide, deshydroxyacetylhenningsamide and cyclostrychnine. Among <strong>the</strong>se, <strong>the</strong><br />

henningsiine and henningsamide derivatives are new alkaloids which possess a (16,17) double<br />

bond. Cyclostrychnine is a novel heptacyclic C21 alkaloid which presents some similarities with<br />

strychnine and has a C-16 to C-23 bond. Structures were established by spectral means and<br />

c h e m i c a l c o r r e l a t i o n s .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Mitsunaga, K., K. Koike, H. Fukuda, K. Ishii and T. Ohmoto<br />

Ligustrinoside, a new bisiridoid glucoside from Dtrychnos ligustrina<br />

1991<br />

Chemical and Pharmaceutical Bulletin<br />

39(10): 2737-2738<br />

Abstract<br />

A new bisiridoid glucoside, ligustrinoside (1), along with three known iridoids, loganin, loganetin<br />

and loganic acid was isolated from <strong>the</strong> wood of <strong>Strychnos</strong> ligustrina BL. (Loganiaceae), collected in<br />

Indonesia. The structure of ligustrinoside (1) has been determined as an ester dimmer of loganin and<br />

l o g a n i c a c i d b e t w e e n C - 7 a n d C - 1 1 .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Mukherjee, R., B. A. Dasilva, B. C. Das, P. A. Keifer and J. N. Shoolery<br />

Structure and stereochemistry of divaricine, a new bisindole alkaloid from Strych<br />

1991<br />

Heterocycles<br />

32(5): 985-990<br />

Abstract<br />

The complete stereostructure of divaricine, a new bisindole alkaloid from Srychnos divaricans<br />

Ducke., has been determined mainly by <strong>the</strong> use of one- and two-dimensional nmr techniques.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Nkiliza J; Vercauteren J; Leger JM<br />

19-hydroxytubotaiwine - total syn<strong>the</strong>sis - assignment of absolute-configuration to<br />

1991<br />

Tetrahedron Letters<br />

32(15): 1787-1790<br />

Abstract<br />

A total syn<strong>the</strong>sis of two isomers of racemic 19-hydroxytubotaiwine from tryptamine is described1.<br />

The absolute configuration of one of <strong>the</strong> two natural ones is defined by a NMR and X-ray study of<br />

a n i n t e r m e d i a t e .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq J; Angenot L; Dupont L; Dideberg O; Warin R; Delaude C; Coune<br />

Revision of <strong>the</strong> structure of strychnochromine<br />

1991<br />

Tetrahedron Letters<br />

32(34): 4295-4298<br />

Abstract<br />

The structure of strychnochromine, an unusual alkaloid isolated from <strong>the</strong> root bark of <strong>Strychnos</strong><br />

gossweileri, has been revised. Strychnochromine 2 possesses a new pentacyclic skeleton with a<br />

tetrahydroquinoline ra<strong>the</strong>r than indole or indoline moiety.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq, J., M. C. Depauwgillet, L. Angenot and R. Bassleer<br />

Effects of strychnopentamine on cells cultured in vitro<br />

1991<br />

Chemico-Biological Interactions<br />

80(2): 203-216<br />

Abstract<br />

This paper describes <strong>the</strong> powerful cytotoxic action exerted by strychnopentamine (SP), a dimeric<br />

indole alkaloid extracted from <strong>Strychnos</strong> usambarensis Gilg, on B16 melanoma cells and on noncancer<br />

human fibroblasts cultured in vitro. SP strongly inhibits cell proliferation and induces cell<br />

death at a relatively low concentration (< 1-mu-g/ml) after 72 h of treatment in <strong>the</strong> two lines.<br />

Incorporation of [H-3]thymidine and [H-3]leucine by B16 cells significantly decreases after only 1 h<br />

of treatment at 0.5-mu-g/ml. SP induces <strong>the</strong> <strong>for</strong>mation of dense lamellar bodies and vacuolization in<br />

<strong>the</strong> cytoplasm, intense blebbing at <strong>the</strong> cell surface and various cytological alterations leading to cell<br />

d e a t h .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Quetinleclercq, J., M. Tits, L. Angenot and N. G. Bisset<br />

Alkaloids of <strong>Strychnos</strong> usambarensis stem bark<br />

1991<br />

Planta Medica<br />

57(5): 501-501<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Quetinleclercq, J., P. Coucke, C. Delaude, R. Warin, R. Bassleer and L. Angenot<br />

Matadine, a cytotoxic alkaloid from <strong>Strychnos</strong> gossweileri<br />

1991<br />

Phytochemistry<br />

30(5): 1697-1700<br />

Abstract<br />

Matadine, a new alkaloid, has been isolated from <strong>the</strong> root bark of <strong>Strychnos</strong> gossweileri.<br />

Elucidation of its structure is mainly based on 1D and 2D NMR studies. Its cytotoxic activity has<br />

b een tested in vitro on cancer cells and normal cells.


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Rawal VH; Michoud C<br />

A general-solution to <strong>the</strong> syn<strong>the</strong>sis of 2-azabicyclo[3.3.1]nonane unit of <strong>Strychnos</strong><br />

1991<br />

Tetrahedron Letters<br />

32(14): 1695-1698<br />

Abstract<br />

The characteristic 2-azabicyclo[3.3.1]nonane substructure of <strong>Strychnos</strong> alkaloids can be constructed<br />

rapidly and stereospecifically using an intramolecular Heck reaction.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Tits, M., J. Damas, J. Quetinleclercq and L. Angenot<br />

From ethnobotanical uses of <strong>Strychnos</strong> henningsii to antiinflammatories, analgesi<br />

1991<br />

Journal of Ethnopharmacology<br />

34(2-3): 261-267<br />

Abstract<br />

<strong>Strychnos</strong> henningsii Gilg is used in African traditional medicine <strong>for</strong> <strong>the</strong> treatment of various<br />

ailments, including rheumatism, gastrointestinal complaints and snake bites. Different preliminary<br />

pharmacological experiments are described. The results show that some of <strong>the</strong> reported folk<br />

medicinal applications of S. henningsii can be at least partially explained by <strong>the</strong> presence of retulinelike<br />

alkaloids, whose use could lead to new antinociceptive (antiinflammatory and analgesic) and<br />

a n t i s p a s m o d i c d r u g s .


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Wright, C. W., D. H. Bray, M. J. Oneill, D. C. Warhurst, J. D. Phillipson, J. Queti<br />

Antiamoebic and antiplasmodial activities of alkaloids isolated from <strong>Strychnos</strong> us<br />

1991<br />

Planta Medica<br />

57(4): 337-340<br />

Abstract<br />

Seven alkaloids isolated from <strong>Strychnos</strong> usambarensis have been assessed <strong>for</strong> in vitro activities<br />

against Entamoeba histolytica and Plasmodium falciparum and <strong>for</strong> in vivo activity against<br />

Plasmodium berghei in mice. Strychnopentamine and 3',4'-dihydrousambarensine were highly active<br />

against P. falciparum in vitro, but were inactive and non-toxic against P. berghei in vivo.<br />

Usambarensine, usambarine, and 18,19-dihydrousambarine were highly active against E. histolytica<br />

in vitro, but were less active against P. falciparum in vitro. N(b)-Methylusambarensine was less<br />

active against both protozoa than was usambarensine, and akagerine possessed little antiprotozoal<br />

activity. Structure-activity relationships are discussed in <strong>the</strong> context of <strong>the</strong> reported cytotoxic and<br />

p harmacological properties of <strong>the</strong>se alkaloids.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Alvarez M; Salas M; Deveciana A; Lavilla R; Bosch J<br />

Nucleophilic-addition of indole-2-acetic ester enolates to n-alkylpyridinium salts -<br />

<strong>1990</strong><br />

Tetrahedron Letters<br />

31(35): 5089-5092<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Amat, M., A. Linares and J. Bosch<br />

A new syn<strong>the</strong>tic entry to pentacyclic <strong>Strychnos</strong> alkaloids - total syn<strong>the</strong>sis of (+/-)-t<br />

<strong>1990</strong><br />

Journal of Organic Chemistry<br />

55(26): 6299-6312<br />

Abstract<br />

A new strategy <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of pentacyclic <strong>Strychnos</strong> alkaloids has been developed. It consists<br />

in <strong>the</strong> closure of <strong>the</strong> five-membered E ring by cyclization upon <strong>the</strong> indole 3-position from a suitably<br />

N-substituted tetracyclic system embodying rings ABCD of <strong>the</strong> alkaloids. Attempts to effect <strong>the</strong> key<br />

cyclization ei<strong>the</strong>r by Pummerer rearrangement of sulfinylacetamides 4 and 6, from chloroacetamide<br />

12, or from bis(methylthio)acetamide 10b (exocyclic amide carbonyl group) resulted in failure. In<br />

<strong>the</strong> first case dithioacetals 9 and 10, respectively, were <strong>for</strong>med in good yields. Cyclization from<br />

alcohol 13 or from <strong>the</strong> indole-deactivated acetal 15 and dithiocetal 18 were also unsuccessful:<br />

noncyclized products coming from <strong>the</strong> initially <strong>for</strong>med oxonium or thionium intermediates 16 were<br />

obtained. Cyclization was satisfactorily accomplished in 49% yield by treatment of <strong>the</strong> N-<br />

unsubstituted indole dithioacetal 23 with DMTSF. The resulting pentacycle 25 was converted to 20-<br />

deethyltubifolidine (27). A similar treatment from dithioacetal 41a, prepared from <strong>the</strong> secondary<br />

amine 32a, af<strong>for</strong>ded pentacycle 42a, from which <strong>the</strong> alkaloids tubifoline, tubifolidine, and 19,20-<br />

d i h y d r o a k u a m m i c i n e w e r e s y n t h e s i z e d .<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Angenot, L., M. L. Belempinheiro, A. F. I. Darocha, P. Poukensrenwart, J. Quetin<br />

An indolinic cryptoalkaloid from <strong>Strychnos</strong> mattogrossensis<br />

<strong>1990</strong><br />

Phytochemistry<br />

29(8): 2746-2749<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Bonjoch, J., A. Linares, M. L. Perez and J. Bosch<br />

Protected 2-indoleacetaldehyde derivatives from 2-acylindoles<br />

<strong>1990</strong><br />

Journal of Heterocyclic Chemistry<br />

27(7): 1979-1981<br />

Abstract<br />

The conversion of tetracyclic 2-acylindoles 1 to <strong>the</strong> protected 2-indoleacetaldehydes 4 and 6 is<br />

reported. 2-Indoleacetaldehydes 5 undergo oxidation to <strong>the</strong> corresponding 2-acylindoles 1.<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Cai, B. C., M. Hattori and T. Namba<br />

Processing of nux vomica .2. Changes in alkaloid composition of <strong>the</strong> seeds of stry<br />

<strong>1990</strong><br />

Chemical and Pharmaceutical Bulletin<br />

38(5): 1295-1298<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Datta, B. and N. G. Bisset<br />

Alkaloids of <strong>Strychnos</strong> ignatii<br />

<strong>1990</strong><br />

Planta Medica<br />

56(1): 133-133<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Kraus, G. A., P. J. Thomas, D. Bougie and L. Chen<br />

Syn<strong>the</strong>sis of a pentacyclic precursor to <strong>the</strong> <strong>Strychnos</strong> alkaloids<br />

<strong>1990</strong><br />

Journal of Organic Chemistry<br />

55(5): 1624-1627<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Mukherjee, R., M. D. F. Melo, C. A. D. Santos, E. Guittet and C. Das<br />

Trinervine, a new indole alkaloid from <strong>Strychnos</strong> trinervis<br />

<strong>1990</strong><br />

Heterocycles<br />

31(10): 1819-1822<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Quetinleclercq, J., L. Angenot and N. G. Bisset<br />

South-American <strong>Strychnos</strong> species - ethnobotany (except curare) and alkaloid scre<br />

<strong>1990</strong><br />

Journal of Ethnopharmacology<br />

28(1): 1-52<br />

-


Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Thepenier, P., M. J. Jacquier, G. Massiot, L. Lemenolivier and C. Delaude<br />

Alkaloids from seeds of strychnos-variabilis and <strong>Strychnos</strong> longicaudata<br />

<strong>1990</strong><br />

Phytochemistry<br />

29(2): 686-687<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Thepenier, P., M. J. Jacquier, J. Henin, G. Massiot, L. Lemenolivier and C. Delau<br />

Alkaloids from <strong>Strychnos</strong> pungens<br />

<strong>1990</strong><br />

Phytochemistry<br />

29(7): 2384-2386<br />

-<br />

Author<br />

Title<br />

Year<br />

Source title<br />

Reference<br />

Abstract<br />

Yuno, K., H. Yamada, K. Oguri and H. Yoshimura<br />

Substrate-specificity of guinea-pig liver flavin-containing monooxygenase <strong>for</strong> mor<br />

<strong>1990</strong><br />

Biochemical Pharmacology<br />

40(10): 2380-2382<br />

-

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