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Vol. 8/1 (2008) 1 - 10 JOURNAL OF NATURAL REMEDIES A review of medicinal plants of the genus Cordia: Their chemistry and pharmacological uses K. Thirupathi, S. Sathesh Kumar, V. S. Raju #, B. Ravikumar, D. R. Krishna, G. Krishna Mohan* University College of Pharmaceutical Sciences, Kakatiya University, Warangal - 506 009. India # Department of Botany, Kakatiya University, Warangal - 506 009. Abstract The plants of genus Cordia comprise of trees and shrubs which are widely distributed in warmer regions. The plants of this species have long been used in traditional and folk medicine for treating various illnesses. Some plants in this species were exhaustively explored and some others are yet to be. Substantial progresses on their chemical and pharmacological properties of some species have been made. In India, the fruits of this species are consumed as vegetable. The pharmacological studies carried out with extracts and purified compounds indicates that the plants of Cordia species posses analgesic, anti-inflammatory, antimicrobial, antiviral and antifertility activities. Various compounds like flavonoids, triterpenes, tannins, alkaloids and fatty acids possessing wide range of bioactivities were isolated from different plant parts of Cordia species. Based on these reports it is clearly indicated that the plants of Cordia genus possess potential therapeutic actions. Key words: Cordia, glycosides, alkaloids, cytotoxic, anti-inflammatory, antimicrobial activities 1. Introduction Natural products have served as a major source of drugs for centuries, and about half of the pharmaceuticals in use today are derived from natural products. The use of natural substances, particularly plants, to control diseases is a centuries old practice that has led to the discovery of more than half of all modern pharmaceuticals [1]. A growing world wide interest in the use of phytopharmaceutical as complimentary or alternative medicine either to prevent or ameliorate many diseases has been noted in recent years. * Corresponding author Email: drgkrishnamohan@yahoo.co.in Cordia is a genus of trees or shrubs, sometimes subscandent in the borage family Boraginaceae. About 300 species have been identified worldwide, mostly in warmer regions. The plant parts like fruits, leaves, stem bark, seeds and roots of most species of plants of the genus Cordia, especially Cordia dichotoma, C. myxa, C. oblique, C. verbenacea, C. martinicensis, C. salicifolia, C. spinescens, C.latifolia, C. ulmifolia, among others, has long been used in traditional medicine for cicatrizant, astringent, anti-inflammatory, anthelminthic, antimalarial, 2 K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 diuretic, febrifuge, appetite suppressant, cough suppressant and to treat urinary infections, lung diseases and leprosy [2-4]. The aim of this review is to provide an overview on the recent status of chemical and pharmacological relevance of the extracts and active constituents isolated and identified in some of the plants belonging to the genus Cordia. 2. Biological investigations The use of plants of Cordia species were highlighted in traditional literatures of Ayurveda and Materia Medicas. These plants were screened for many pharmacological activities and are listed in table 1. The plants of the genus Cordia serve as a rich source of phytoconstituents. A wide range of compounds like Phenolics (Fig: 1), Flavonoids, Pyrrolizidine alkaloids, Cardiaquinones (Fig: 2), Tannins, Phenyl propanoid derivatives (Fig: 3) and triterpenes (Fig: 5) are observed. Some of these isolated compounds were reported to be bioactive. A new meroterpenoid benzoquinone isolated from roots of Cordia globosa was compared for cytotoxic action with doxirubicin and the results were found statistically significant. Triterpenoid benzoquinones were very commonly reported from Cordia species whereas rarely some cerebrosides (Fig: 4) were reported from Cordia platythyrsa [75]. Rosmarinic acid (Fig: 3) is an ester of caffeic acid and 3, 4-dihydroxyphenylactic acid [2-Ocafeoil-3-(3, 4-di-hydroxy-phenyl)-R-lactic acid] was isolated from Cordia verbenacea by using semi preparative HPLC technique [47]. A polysaccharide isolated from Cordia abyssinica [48] was studied for emulsifying properties and exhibited best results between pH 7 and 11. Apart from these, various essential oils and fatty acids were also isolated from various Cordia species. A detailed data of compounds isolated from various plants of Cordia species are given in table 2. Table 1. Biological Investigations Species Part Used Reported Activity Ref Cordia alliodora (Ruiz & Pav.) Oken. Root bark Antifungal, larvicidal 5 Cordia corymbosa Willd. ex Roem. & Schult. Fruits Antimicrobial, Cytotoxic, Tumour inhibition 6 Cordia curassavica (Jacq.) Roem. & Schult. Roots Antifungal, Larvicidal Antibacterial 7 8 Cordia cylindrostachya Roem.& schult Antibacterial, Anti-inflammatory 9 Cordia dichotoma G. Forst. Fruits Fruits Leaves Anthelmintic Wound healing Antifertility Juvenomimetic Biliary obstruction Nutritional food 10 11 12 13 14 15 Cordia fragrantissima Kurz. Wood Leishmanicidal 16 K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 3 Cordia francisci Ten. Leaves Analgesic, Anti-inflammatory 17 Cordia globosa (Jacq.) Kunth. Root Leaves Cytotoxic Vasodilator, Spasmolytic 18 19 Cordia goetzei Gürke. Stem bark Antifungal 20 Cordia latifolia Roxb. Ripen fruits Anti-Ulcer Antihistaminic 21 22 Cordia linnaei Stearn. Roots Antifungal, larvicidal 23 Cordia martinicensis (Jacq.) Roem. & Schult. Leaves Cytotoxic, Hepatotoxic Anti-inflammatory, Analgesic 24, 25 17 Cordia monosperma (Jacq.) Roem. & Schult. Aerial parts Antimicrobial 26 Cordia multispicata Cham. Leaves Antiandrogenic activity 27 Cordia myxa L. Leaves Anti-inflammatory Analgesic, Anti-arthritic Astringent, Anthelmintic Diuretic, demulcent Cytotoxic Antimicrobial Alcoholic liver cirrhosis Antifertility Antihistaminic Antitumour 28, 17 29 30 25 31 32 33 34 35 Fruits Leaves Fruits, leaves Bark Cordia oblique willd. Seeds Anti-inflammatory 36 Cordia perrottettii DC. Fruits Antioxidant 37 Larvicidal 38 Antiviral Excitory & negative Ionotropic effect 39 Cordia plauhiensis Fresen. Cordia salicifolia Cham. Cordia serratifolia Kunth. Whole plant Leaves 40 Analgesic, Anti-inflammatory 17 Cordia sinensis Lam. Leaves Antitumour 35 Cordia spinescens L. Leaves Leaves Antiviral Anti-HIV 41 42 Cordia ulmifolia Juss. ex Dum. Cours. Leaves Cytotoxic, Hepatotoxic Anti-inflammatory, Analgesic 24, 25 Leaves Cordia verbenacea DC. Leaves Aerial parts Leaves Anti-inflammatory, Analgesic, Fetus toxicity Antimicrobial Antiserum action, Potentiation 17 43, 44, 45 46 47 4 K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 Table 2. Chemical Investigations Species Phytoconstituents Part Used Ref. Cordia abyssinica R.Br. Polysacharides, gums Fruits 48, 49 Cordia alliodora (Ruiz & Pav.) Oken Alliodorin Tetracyclic di-o-methyl hydroquinone Root bark 5 Heart wood 50 Cordia corymbosa Willd. ex Roem. & Schult. Meroterpenoid quinonesCardiaquinone A & B Cardiaquinone C & D Roots Roots 51 52 Cordia Cylindrostachya Roem.& schult. -pinene, amphene,tricylene Cordia decandra Hook. & Arn. Menisdaurin, dhurrin, p-hydroxybenzaldehyde Leaves 53 Rosmarinic acid, Quercetin, 3-o-rutinoside Flowers 54 Cordia dichotoma G. Forst. Arabinoglucan D-Glucose, L-Arabinose -linolinic acid Quercetin, quercitrin Fruits Fruits Seed Leaves 55 56, 57 58 59 Cordia globosa (Jacq.) Kunth. 7- methoxy flavone, 5-7, 3’, 4’tetrahydroxy methoflavone Meroterpenoid benzoquinone, Napthoquinone Aerial parts 60 Roots 18 Cordia dentata Poir. 9 Cordia goetzei Gürke Cordigone, cordigole, benzofurons. Stem bark 20 Cordia linnaei Stearn Isomeric meroterpenoid Napthoquinone Napthoxirene Roots 61 23 Cordia macleodii Hook. f. & Thomson p-hydroxyphenylactic acid, Quercetin Leaves, Flowers 62 Cordia multispicata Cham. Cordinol A, Cordialin A Leaves 63 Cordia myxa L. Quercitrin or rutin Fixed oils -linolinic acid, linoleic acid, oleic acid, -sitosterol Carotenoids Pyrrolizidine alkaloids Saponins Minor minerals-Chromium Leaves Seeds 64, 65 66 Leaves Leaves Leaves Bark 67 31 68 69 70 K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 Cordia obliqua Willd. 5 Hesperetin-7-rhamnoside Lupa-20, 29-ene-3-o-D-maltoside Toxifolin-3, 5-dirhamnoside Natural gums, mucilages Root 71 Root Seeds Fruits 72 73 74 Cordia platythyrsa Baker Cerebrosides Cordiachromes A-F Stem bark Heart wood 75 76 Cordia plauhiensins Fresen. Saponins Stem 77 Cordia rothii Roem. & Schult and Cordia sebestina L. Linoleic and oleic acids, -Sitosterol Leaves 78 Cordia spinescens L. Magnesium lithospermate, Magnesium rosmarinate, Calcium rosmarinate Leaves 79 Cordia trichotoma (Vell.) Arráb. ex Steud. -cadinol, -muurolol Epi--muurolol Heart wood, Sapwood 80 Cordia verbenacea DC. -pinene, trans-Cariophyllene, Aloaromadendrene Cordialin A, Cordialin B Rosmarinic acid Flavanols-artemetin, Brickelin Aerial parts Leaves Leaves 81 82 83 Aerial parts 84 R1=R2= OH R3=Rhamnose Cordigone (Cordia goetzei) Cordigol (Cordia goetzei) Rutin (Cordia dentata) Fig. 1: Phenolic compounds isolated from various species cordiaquinone A cordiaquinone J Fig. 2: Cordiaquinones isolated from Cordia curassavica cordiaquinone K 6 K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 1-(3-methoxypropanoyl)-2, 4, 5-dimethylocta-2, 6-dienyl)-1, 4-benzenediol (Cordia alliodora) Prenylated hydroquinone, 2-(2Z)(3-hydroxy-3, 7-trimethoxybenzene (Cordia alliodora) Rosmarinic acid (Cordia verbenacea) Fig 3: Phenyl propanoid derivatives from various Cordia species (2S, 3S, 4R, 8E)-2N-[(2#R)-2#- hydroxy-tetracosanoyl]-8(E) -octadecene-1, 3, 4-triol 1-O-(b-D-glucopyranosyl)-(2S, 3S, 4R, 8E)-2N-[(2#R)-2#-hydroxytetracosanoyl]-8(E)-octadecene-1, 3, 4-triol Fig. 4: Cerebrosides isolated from Cordia platythyrsa K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 Napthoquinone (cordial globosa) Cordianol A (cordia multispicata) Cordialin A (cordia multispicata) Lupa-20, 29-ene-3-o--d-maltoside (Cordia obliqua) 7 Fig. 5: Terpenoids isolated from various Cordia species 3. Discussion The scientific evidence on the plants of Cordia species indicates the traditional usage of this species for treating different ailments was highly justified. Extensive phytochemical studies carried out on these plants and wide classes of compounds including flavanol glycosides, pyrrolizidine alkaloids, triterpenes, cardiaquinone, sphingolipids, cerebrosides were isolated. Cordia verbenacea is one of the ingredients in the formulation “Acheflan” manufactured by Brazilian Ache laboratories [85]. Most of the activities of Cordia species were proved in animals. The lack of clinical studies on the Cordia species is well indicated in this review. Similarly few reports are there on standardization of the bioactive compound present in the plants of this species. The polysaccharides isolated from Cordia abyssinica open the doors for development of new natural hydrocolloids [72] and emulsifiers [71]. 4. Conclusion and perspectives The present need for development of new therapeutic agents from natural sources had made the researchers to refresh and uncoil the literatures. This review gives a comprehensive data of compounds isolated and biological studies reported in this species. It is clear that Cordia species contains various compounds like 8 K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 flavanol glycosides, pyrrolizidine alkaloids, triterpenes, cardiaquinones, sphingolipids, cerebrosides. Most of the traditional uses were scientifically proved in animal models. Some of the activities reported were anti-inflammatory, cytotoxic, antiviral, antimicrobial, anti-Ulcer, antifungal, larvicidal antiandrogenic activity. No potential side effects were reported from any of these plants where as hepetotoxic effect was reported from C. ulmifolia. Still the clinical effectiveness and other safety specifications about the doses are not clear. Development of suitable methods for effective isolation of bioactive compounds and reliable analytical techniques are future research perspectives. More over some plants of this species indicated the scope not only for development of new phytotherapeutic agents but also new pharmaceutical excepients. References 1. Soejarto DD, Farnsworth NR. (1989) Perspect Biol Med.32: 244-256. 13. Neraliya S, Srivastava US. (1997) J. Med. Arom. Plant. Sci. 19 (3): 677-681. 2. Sertié- JAA, Basile AC, Panizza S, Matida AK, Zelnik R. (1990) Planta Med. 56: 36. 14. Yin,-Wen-Yao, Huang,-Shin-Ming, Lee,-PoChang, Lee-Cheng-Chang, Chang-TsaiWang,Yang-Yu-Jen. (1997) Hepatol Gastroenterol. 44(16): 1037-1045. 3. Marston A, Zagorski MG, Hostettmann K. (1988) Helv Chem Acta. 71: 210. 4. Tiwari RD, Srivastava KC, Shukla S, Bajpai RK. (1967) Planta Med.15: 144. 5. Jean-Robert Ioset, Andrew Marston, Mahabir P, Gupta, Kurt Hostettmann. (2000) J.Nat.Prod. 63: 424-426. 6. A silva Filho AA, Correa Lima RMO, Nascimento SC, Silva EC, Andrade MSAS, Bieber LW. (1993) Fitoterapia. 64(1): 78-81. 7. Jean-Robert Ioset, Andrew Marston, Mahabir P, Gupta, Kurt Hostettmann. (2000) Phytochemistry. 53, 613-617. 8. Hernandez T, Canaales M, Avila JG, Duran A, Cabellero J, de Vivar AR, Lira. (2003) J.Ethnopharmacol. 88(2-3): 181-188. 9. Fun CE, Cvendsen B. (1990) J. Essential Oil Res. 2(4): 209-210. 15. Duhan A, Chauhan BM, Punia D. (1992) Plant Food Hum. Nutr. 42 (3): 193-200. 16. Takahashi M, Fuchino H, Satake M, Agatsuma Y, Sekita S. (2004) Biol. Pharm. Bull. 27(6): 921-925. 17. A.Rapisarda, Ficarra R, Tommasini S, Calabro ML, Ragusa S. (1992) Planta Med. 58 (1): 643. 18. Jane Eire S, Alencar de Menezes, Telma Leda G. Lemos, Otilia Deusdenia L. Pessoa, Raimundo Braz-Filho, Raquel C. Montenegro, Diego versa Wilke, Leticia V. Costa- Lotufo, Claudia pessoa, Manoel odorico de moraes, Eddilberto R.Silveira. (2005) Planta Med. 71: 54-58. 19. Silva SAS, Rodrigues MSl, Agra MF, da- Cunha EVL, Barbosa-Filho, Silva MS. (2004) Bio chem. Syst. Ecol. 32: 359-361. 10. Kuppasta Nayak IJ, Vasudeva. (2003) Ind. J. Nat. Prod. 19(3): 27-29. 20. Andrew Marston, Michael G. Zagorski, Kurt Hostettmann. (1988) Helv. Chem. Acta. 71:1210-1219 11. Kuppast IJ, Vasudeva Nayak P. (2006) Nat. Prod. Radiance. 5: 103-107. 21. Abdul Hameed Akhtar, Kamal Uddin Ahmad. (1995) J.Ethnopharmacol. 46:1-6. 12. Choudary DN, Singh JN, Verma SK, Singh BP. (1990) Ind. J. Exp. Biol. 28 (8): 714-716. 22. Pillai KK, Ansari SK, QadryAS, Qadry JS. (1992) J. Nat.Prod. 8(1): 16-17. K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 23. Ioset JR, Marston A, Gupta MP, Hostettmann K. (1998) Phytochemistry. 47(5): 729-34. 24. Rapisarda A, Ragusa S. De Pasquale. Medicinal and Aromatic Plants Conference, ISHS Acta HorticultureG. 25. Gabrielli G, Trovato A, Rapisarda A, Ragusa S. (1993) Pharmacol. Res. 27(1):1993 26. Coelho de Souza, Has APS, von Poser GL, .Schapoval EES, Elisabetsky E. (2004) J. Ethnopharmacol. 90:135-143. 27. Kuroyanagi M, Seki T, Hayashi T, Nagashima Y, Kawahara N, Sekita S, Satake M. (2001) Chem Pharm Bull (Tokyo). 49(8): 954-7. 28. Farida M, Al-Awadi TS, Srikumar JT, Anim FRCPath, and Islam Khan. (2001) Nutrition. 17(5): 391-396. 9 38. Santiago GMP, Viana FA, Pessoa ODL, Santos RP, Pouliquen YBM, Arriaga AMC, AndradeNeto M, Braz-Filho R. (2005) Brazilian J. Pharm. 15(3): 187-190. 39. Hayashi K, Hayashi T, Morita N, Niwayama S. (1990) Planta Med. 56(5): 439-443. 40. Matsunaga K, Sasaki S, Ohizumi Y. (1997) Nat. Med. 51(5): 478-481. 41. Matsuse IT, Lim YA, Hattori M, Correa M, Gupta MP. (1999) J. Ethnopharmacol. 64: 15–22. 42. Lim YA, Kojima S, Nakamura N, Miyashiro H, Fushimi H, Komatsu K, Hattori M, Shimotohno K, Gupta MP, Correa M. (1997) Phytother Res. 11 (7): 490-495. 43. Sertie JAA, Woisky G, Wiezel Z, Rodrigues M. (2005) Phytomedicine. 12(5): 338-44. 29. Ficarra R, Ficarra P, Tommasini S, Calabrò ML, Ragusa S, Barbera R, Rapisarda A. (1995) Pharmacology. 4: 245. 44. Sertie JAA, Basile AC, panizza S, Matida A.K, Zelnik R. (1990) Planta Med. 56(1): 36-40. 30. Tiwari RD, Srivastava KC, Shrirama S, Bajpai RK. (1967) Planta Med. 15: 240. 45. Sertie JA, Basile AC, panizza S, Oshiro TT, Azzolini CP, Penna SC. (1991) J. Ethno pharmacol. 31: 2 31. Afzal M, Obuekwe C, Shuiab N, Barakat H. (2004) Fd. Agric. and Environ. 2 (2): 114-120. 32. Rajesh MC, Paul B, Latha MS. (2000) Antiseptic. 97(9): 320-321. 33. Sinha M, Tiwari PV. (1999) South East Asian Seminar on Herbs and Herbal Medicines, Patna, 55-62. 34. Rimando Am, Inoshiri S, Ostuka H, Kohda H, Yamasaki K, Padolina WG, Torres L, Quintana EG,Cantoria MC. (1987) Shoyakugaku Zasshi. 41(3): 242-247. 35. Wassel G, El-Menshawi B, Saeed A, Mahran G, El-Merzabani M. (1987) Pharmazie. 42(0): 709. 36. Agnihotri VK, Srivastava SD, Srivastava SK, Pitre S, Rusia K. (1987) Ind. J. Pharm. Sci. 49(2), 66-69. 37. Ruchi G. Marwah, Majekodunmi O. Fatope, Ramla Al Mahrooqi, Gouri B. Varma, Hussain Al Abadi, Suad Khamis S. Al-Burtamani. (2006) Food Chem. 1-6. 46. De Carvalho Jr PM, Rodrigues RFO, Sawaya ACHF, Marques MOM, Shimizu MT. (2004) J. Ethnopharmacol. 95: 297-301 47. Ticli FK, Hage LI, Cambraia RS, Pereira PS, França SC, Magro AJ, Fontes MRM, Stábeli RG, Giglio JR, Soares AM, Sampaio SV. (2005) Toxicon. 46(3): 318-327 48. Mudadi Albert Nhamoiesu Benhura, Cathrine Katayi Chidewe. (2004) Int. J. Food. Sci. Tech.39: 579-583. 49. Benhura MAN, Chidewe C. (2002) Food Chem. 76: 343-347. 50. Manners CD, Wong RY. (1981) J.Chem.Soc; Perkin Trans I. 7: 1849-1854. 51. Bieber LW, Messana I, Lins SCN, Da Silva Filho AA, De Mello JF. (1990) Phytochemistry. 29(6): 1955-1959. 52. Bieber LB, Krebs HC, Schafer W. (1994) Phytochemistry. 35(4): 1027-1028. 10 K. Thirupathi et al. / Journal of Natural Remedies, Vol. 8/1 (2008) 1 - 10 53. Ei-sayed NH, Moharram FAK, Abdel- Allim MA, Mabry TJ. (1998) Rev Lat am quim. 26(1): 3035. 69. Khan N, Mahmooduzzafar, khan AU. (1993) Medicinal plants, new vistas of research. 10(1): 181-187. 54. Ferrari F, Delle Monache F, Campagnone RS, Oliveri MC. (1997) Fitoterpia. 68: 88. 70. Janjua KM. (1991) Hamdard medicus. 34 (2): 104-106. 55. Nanda G, Basu, Pradyot K, Ghosal, Swapnadip Thakur. (1986) Carbohydrate Res. 146: 350351. 71. Chauhan JS, Srivastava SK, Sultan M. (1978) Phytochemistry. 17: 334. 56. Nanda G, Basu, Pradyot K, Ghosal, Swapnadip Thakur. (1986) Carbohydrate Res. 146: 149155. 57. Basu NG, Ghosal PK, Thakur S. (1984) Carbohydrate Res. 131(1): 149-156. 58. Guil-Guerrero JL, Garcia- Maroto F, VilchesFerro´n c M.A, Lo´pez-Alonso D. (2003) Ind Crop Prod. 18: 85-89. 59. Wang,-Yan, Ohtani,-Kazuhiro, Kasai Ryoji, Yamasaki,-Kazuo. (1996) Nat. Medicines. 50(5): 367. 60. Saˆmia Andricia Souza da Silva, Marla Simone Lopes Rodrigues, Maria de Fa´tima Agra, Em?´dio Vasconcelos Leita˜o da-Cunha, Jose´ Maria Barbosa-Filho, Marcelo Sobral da Silva. (2004) Biochem. Syst. Ecol. 32: 359–361. 61. Jean-Robert Ioset, Jean-Luc Wolfender, Andrew Marston, Mahabir P. Gupta, Kurt Hostettmann. (1999) Phytochem Analysis. 10(3): 137-142. 62. Ei-sayed NH, Moharram FAK, Abdel- Allim MA, Mabry TJ. (1998) Rev Lat am quim. 26(1): 30-35. 63. Kuroyanagi M, Kawahara N, Sekita S, Satake M, Hayashi T, Takase Y, Masuda K. (2003) J. Nat. Prod. 66(10): 1307-12. 64. Galvez J. (1996) Methods Find Exp Clin Pharmacol.18 (suppl B): 7. 65. Pietta P, Simonetti P. (1998) Biochem Mol Biol Int. 44:1069. 66. Tiwari RD, Srivastava KC, Shukla S, Bajpai RK. (1967) Planta medica. 15 (3), 240-4. 67. Miralles J, Noba K, Bassene E. (1989) Herba Hungarica. 28(1-2): 7-12. 68. Wassel G, El-Menshawi B, Saeed A, Mahran G,Reisc J. (1987) Scientia Pharmaceutica. 55(3): 163-166. 72. Jgdish S, Chauhan JS, Srivastava, Santhosh K. (1978) Phytochemistry.17: 1005-1006. 73. Santhosh K, Srivastava, Savitri D, Srivastava. (1979) Phytochemistry.18: 2058-2059. 74. Baveja SK, Ranga Rao KV, Arora J. (1989) Ind. J. pharm. Sci. 51(4): 115-118. 75. Le´ on Azefack Tapondjou, Anne-Claire MitaineOffer, Marc Sautour, Tomofumi Miyamoto, Marie-Aleth Lacaille-Dubois. (2005) Biochem Syst Ecol. 33: 1293-1297. 76. Moir M, Thomson RH. (1973) J. Chem. Soc. Perkin Trans. I: 1352. 77. Santos RP, 1 ER Silveira, Leda T, Lemos G, Viana F, Braz-Filho A, Rand Ot´ýlia Deusd eˆ nia L Pessoa1 (2005) Magn. Reson. Chem. 43: 494–496. 78. Miralles J, Noba K, Bassene E. (1989) Herba Hungarica. 28(1-2): 7-12. 79. Nakamura N, Kojima S, Lim YA, Meselhy MR, Hattori M, Gupta MP, Correa M. (1997) Phytochemistry. 46(6): 1139-1141. 80. de Menezes JES, Lemos TLG, Solveira ER, Andrade-Neto, M, Nascimento RF, Pessa ODL. (2005) Flavour Frag J. 20(2): 149-151. 81. Akisue MK, Oliveira F, Moraes MS, Akisue G, Mancini B. (1983) Rev de cies Farms. 5: 69-82. 82. Velde VV, Lavie D, Zelnik R, Matida AK, Panizza S. (1982) J. Chem. Soc. Perkin Trans 1: 2697-2700. 83. Ticli FK, da costa SMC, da Silva JO, Pereira PS, Sampaio SV. poster session P12. Drug Toxicology. 84. Lins AP, de Alvarenga MA, Gottlieb CR, de oliveira F. (1990) Rev Lat am quim. 21(2): 82. 85. Jo˜ao B. Calixto (2005) J.Ethnopharmcol. 100:131–134.