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Review

Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features

by
Yhiya Amen
1,2,†,
Marwa Elsbaey
2,†,
Ahmed Othman
1,3,†,
Mahmoud Sallam
3,† and
Kuniyoshi Shimizu
1,*
1
Department of Agro-Environmental Sciences, Graduate School of Bioresources and Bioenvironmental Sciences, Kyushu University, Fukuoka 819-0395, Japan
2
Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
3
Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, Egypt
*
Author to whom correspondence should be addressed.
†
Authors contributed equally to this work.
Molecules 2021, 26(24), 7646; https://doi.org/10.3390/molecules26247646
Submission received: 16 November 2021 / Revised: 13 December 2021 / Accepted: 13 December 2021 / Published: 16 December 2021
(This article belongs to the Special Issue Isolation, Structure Elucidation and Biological Activity of Natural Products)
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Abstract

:
Chromone glycosides comprise an important group of secondary metabolites. They are widely distributed in plants and, to a lesser extent, in fungi and bacteria. Significant biological activities, including antiviral, anti-inflammatory, antitumor, antimicrobial, etc., have been discovered for chromone glycosides, suggesting their potential as drug leads. This review compiles 192 naturally occurring chromone glycosides along with their sources, classification, biological activities, and spectroscopic features. Detailed biosynthetic pathways and chemotaxonomic studies are also described. Extensive spectroscopic features for this class of compounds have been thoroughly discussed, and detailed 13C-NMR data of compounds 1–192, have been added, except for those that have no reported 13C-NMR data.

1. Introduction

Chromone glycosides are a class of secondary metabolites with various medicinal properties. They are widely distributed in many plant genera and, to a lesser extent, in some fungal species and other sources [1]. Several biological activities have been reported for various chromone glycosides. For example, aloesin and its analogues, from Aloe, are used in cosmetic preparations to treat hyperpigmentation induced by UV radiation, owing to their role in inhibition of tyrosinase enzyme [2,3]. Additionally, 8-[C-β-d-[2-O-(E)-cinnamoyl]glucopyranosyl]-2-[(R)-2-hydroxypropyl]-7-methoxy-5-methylchromone), isolated from certain Aloe species, was reported to have potent topical anti-inflammatory activity comparable to the effect of hydrocortisone without affecting thymus weight [3]. Macrolobin, from Macrolobium latifolium, has a remarkable acetylcholinesterase inhibitory activity with an IC50 value of 0.8 µM. Uncinosides A and B, isolated from the Chinese herbal medicine Selaginella uncinata, showed potent anti-RSV (respiratory syncytial virus) activity with IC50 values of 6.9 and 1.3 µg/mL. Taking into consideration the broad biological activities of chromone glycosides, this review summarizes the naturally occurring chromone glycosides and categorizes these compounds on their structural basis, in addition to their sources, bioactivities and spectroscopic features. Importantly, this review will shed more light toward the NMR features of chromone glycosides to help natural product researchers in the identification of various chemical structures. Scientific databases as SciFinder, PubMed, and Google Scholar were used to collect the relevant literature data.

2. Biosynthesis

Chromones are biosynthesized through the acetic acid pathway by the condensation of five acetate molecules. These compounds, generally, have a methyl group at C-2 and are oxygenated at C-5 and C-7 [4]. Pentaketide Chromone Synthase (PCS) is a key enzyme in the biosynthesis process that catalyzes the formation of a pentaketide chromone (5,7-dihydroxy-2-methylchrome) from five-step decarboxylative condensations of malonyl-CoA, followed by the Claisen cyclization reaction to form an aromatic ring. However, it is unclear whether the heterocyclic ring closure of the pentaketide chromone is enzymatic or not, because the ring closure can take place due to spontaneous Michael-like ring closure, as in the case of flavanone formation from chalcone in vitro. PCS also accepts acetyl-CoA, resulting from decarboxylation of malonyl-CoA, as a starter substrate, but it is a poor substrate for PCS [5].The pentaketide chromone has been isolated from several plants and is known to be the biosynthetic precursor of the chromone derivatives with additional heterocyclic rings (e.g., furano-, pyrano- and oxepino-chromone glycosides). Scheme 1 ([6] with modifications) shows the sequence of steps utilized in the biosynthesis of these compounds, fully consistent with the biosynthetic rationale developed above. The key intermediate is 5,7-dihydroxy-2-methylchromone [5,6]. For many years, the cyclization had been postulated to involve an intermediate epoxide, such that nucleophilic attack of the phenol onto the epoxide group might lead to formation of either five-membered furan, six-membered pyran or the seven-membered oxepin heterocycles, as commonly encountered in natural products [6].
Aloesone Synthase (ALS) (Scheme 2, [5] with modifications) is a key enzyme in the biosynthesis of heptaketide chromone aloesone derivatives, such as aloesone 7-O-β-d-glucopyranoside (53) in rhubarb and anti-inflammatory aloesone 8-C-β-d-glucopyranoside (aloesin, 98) in Aloe (A. arborescens). ALS efficiently catalyzes the formation of a heptaketide aromatic pyrone 6-(2-(2,4-dihydroxy-6-methylphenyl)-2-oxoethyl)-4-hydroxy-2-pyronechromone from acetyl-CoA and six molecules of malonyl-CoA through an aldol cyclization. The unstable heptaketide pyrone (or acid form) would then undergo subsequent spontaneous isomerization to the β-ketoacid chromone, which is followed by decarboxylation to produce the heptaketide aloesone [5].

3. Taxonomy

We have reviewed the literature concerning the occurrence of chromone glycosides, and we have found that 192 different chromone glycosides have been isolated from different natural sources, including angiosperms, ferns, lichens, fungi and actinobacteria (Table 1). The occurrence of chromone glycosides is mostly confined to botanical families: Apiaceae, Fabaceae, Myrtaceae, Asphodelaceae, Ranunculaceae, Rubiaceae, Hypericaceae, Ericaceae, Amaryllidaceae, Polygonaceae and Araceae. However, few chromone glycosides are also present in Asteraceae, Eucryphiaceae, Saxifragaceae, Smilacaceae, Pentaphylaceae, Salicaceae, Meliaceae, Euphorbiaceae, Staphyleaceae, Amaranthaceae, Aquifoliaceae, Rosaceae, Bignoniaceae, Olacaceae, Pinaceae, Selaginellaceae, Gentianaceae, Cannabaceae, Euphorbiaceae, Cucurbitaceae, Thymelaeaceae and Poaceae. Many of the naturally occurring chromone-8-C-glycosides such as the well-known chromone glycoside aloesin (98) were reported from genus Aloe. Until now, chromone glycosides with additional heterocyclic moieties such as pyrano-, oxepino- and pyrido-chromone glycosides were only isolated from Saposhnikovia divaricate, Eranthis species and Schumanniophyton magnificum, respectively. Another interesting category comprises hybrids of furano-chromones with cycloartane triterpenes, which were reported from Cimicifuga foetida. Actinobacteria also constitute an important source of the chromone alkaloid aminoglycosides, which are isolated from Streptomyces, Saccharothrix and Actinomycete species.

4. Chromone Glycosides

Chromone glycosides belong to a group of oxygen-containing heterocyclic compounds with a benzo-γ-pyrone skeleton. Naturally occurring chromone glycosides can be either O-glycosides or C-glycosides. For O-glycosides, the most frequently encountered group is the 7-O-glycosides; however, 2-, 3-, 5-, 8-, 11- and 13-O-glycosides also exist but to a lower extent. For an example, only one 6-O-glycoside 11 has been reported from nature, and from fungi, not higher plants [1]. Glycosylation can also be detected at side chains for chromones, at C-11 and C-12 as in compounds 56–59, at the hydroxyprenyl and hydroxyisoprenyl side chains as in 123 and 128, respectively, or at the phenyl ethyl moiety as 139. The most abundant among chromone glycosides is the glucoside from. However, other sugar moieties such as xylose, arabinose and rhamnose were also detected in 3-, 7- and 11-O-glycosides.

4.1. Chromone O-glycosides

4.1.1. 2-O-Glycosides

This category includes compound 1 (Figure 1), 2-hydroxy-5-methylchromone-β-d-glucopyranoside, isolated from the aerial parts of Mutisia acuminata var. hirsuta, a member of family Asteraceae [7]. The authors did not report biological activity for this compound.

4.1.2. 3-O-Glycosides

This category includes compounds 2–5. They share the same aglycone nucleus but with different sugar moieties at C-3. Eucryphin 4 was reported as a new compound in 1979 [8]; however, it was reported again in 1996 as a new compound under the name smiglanin [9]. In addition, 3,5,7-trihydroxychromone 3-O-β-d-xylopyranoside 2 was first reported in 2005 from Rhodadendron ovatum [10], but it was reported again as a new compound in 2013 [11]. Compounds 2–5 are shown in Figure 2. The sources and the reported biological activities are summarized in Table 2.

4.1.3. 5-O-Glycosides

Among the naturally occurring 5-O-glycosides, Staphylosides A and B (8–9), isolated from Staphylea bumalda, are characterized by a presence of a disaccharide moiety attached to C-5. The disaccharide chain in 8 is β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside while in 9, is α-d-glucopyranosyl-(1→6)-β-d-glucopyranoside. Compounds 6–10 are shown in Figure 3. The sources and the reported biological activities (if any) are summarized in Table 3.

4.1.4. 6-O-Glycosides

Compound 11 (Figure 4) has a unique structure for bearing 4-O-methylglucopyranosyl unit. Chemically, it is 6-O-(4-O-methyl-β-d-glucopyranosyl)-8-hydroxy-2,7-dimethyl-4H-benzopyran-4-one, isolated from the rice culture of the fungus Armillaria tabescens [1]. Although such compounds are not common in higher plants, several of them have previously been isolated from fungi [1].

4.1.5. 7-O-Glycosides

This subclass is characterized by the presence of sugar at C-7. Hyperimone A is the same as Urachromone A (22), reported at nearly the same time from different co-authors from the genus Hypericum. Takanechromone A (38) is the same as Hyperimone B, isolated from the same genus by different co-authors. They were reported each time as new compounds. We preferred to add only 13C-NMR data of one set of these compounds (Table 23). Several biological activities have been reported to some members of this subclass. Compounds 12–53 are shown in Figure 5. The sources and the reported biological activities (if any) are summarized in Table 4.
Drynachromosides C (30) and D (33) exhibited inhibitory activity on triglyceride accumulation [22]. The effects of these compounds on mRNA expression of the three adipogenesis-related marker genes, PPARγ, C/EBPα and Ap2, in 3T3-L1 were investigated. The mRNA expression levels of PPARγ, C/EBPα and Ap2 were found to be dramatically downregulated. Compounds 40 and 43, having a unique sugar unit of 4-O-methyl-β-d-glucopyranose, were isolated from the scale-insect pathogenic fungus Orbiocrella sp. BCC 33248 [23]. Uncinosides A (46) and B (48) [24], isolated from the Chinese herbal medicine Selaginella uncinata, showed potent anti-RSV (respiratory syncytial virus) activity with IC50 values of 6.9 and 1.3 µg/mL, respectively. Uncinoside B (48) was found to have a TI value of 64.0, a large therapeutic index comparable to that of ribavirin with a TI value of 24.0, which is an approved drug for the treatment of RSV infection in humans. They also showed moderate antiviral activities against PIV 3 (parainfluenza type 3 virus) with IC50 values of 13.8 and 20.8 µg/mL and TI values of 6.0 and 4.0, respectively.

4.1.6. 8-O-Glycosides

Only two compounds 54–55 were reported in nature. They are shown in Figure 6. The sources and the reported biological activities (if any) are summarized in Table 5.

4.1.7. 11- and 13-O-Glycosides

Compound 57 was reported in 2012 as Monnieriside A [60] and was then reported as Drynachromoside B [22,31,47]. Compounds 56–59 are shown in Figure 7. The sources and the reported biological activities (if any) are summarized in Table 6.

4.1.8. Chromanone Glycosides

Chromanone glycosides or 2,3-dihydrochromone glycosides are not abundant in nature. Reviewing the literature, we encountered only four examples 60, 61, 62 and 63. Their structures are shown in Figure 8. The sources and biological activities (if any) of these compounds are summarized in Table 7.

4.2. Chromone C-Glycosides

In contrast to chromone O-glycosides, which are widely distributed and of common occurrence, C-glycoside derivatives are rarely found out.

4.2.1. 3-C-Glycosides

This subclass includes the unusual 5,7-dihydroxychromone-3α-d-C-glucoside, named macrolobin, isolated from the aerial parts of Macrolobium latifolium [65]. Its structure is shown in Figure 9. Its source and biological activities are summarized in Table 8.

4.2.2. 6-C-Glycosides

Compounds 65–79 are shown in Figure 10. The sources and the reported biological activities (if any) are summarized in Table 9.

4.2.3. 8-C-Glycosides

Many of the naturally occurring chromone-8-C-glycosieds can be found in genus Aloe. Approximately 26 chromone-8-C-glycosides were reported in the perennial plant Aloe vera, which is a well-known pharmaceutical herb used in traditional Chinese medicine [76]. Some significant bioactive chromone-8-C-glycosides were isolated and identified in Aloe vera, including Aloesin (98), aloeresin E (109), isoaloeresin D (110), aloeresin A (114) and other derivatives. For instance, aloeresin A (114) exhibited a promising therapeutic activity toward α-glucosidase enzyme [79], while the compound isobiflorin (80), isolated from the flower buds of Syzygium aromaticum, had the capacity to inhibit LPS-induced production of nitric oxide (NO) and prostaglandin E2 (PGE2) in RAW 264.7 macrophages [67]. A chromone-8-C-glycoside, 5,7-dihydroxy-2-isopropylchromone-8-β-d-glucoside, reported in Hypericum japonicum, showed an activity against Epstein–Barr virus [71]. Additionally, BACE1 (β-secretase), which is a possible potential target in the treatment of Alzheimer’s disease, was inhibited by some compounds as aloesin (98) [80], 7-O-methyl-aloeresin A (115) [81] and 2′-feruloyl-7-O-methylaloesin (119) [80]. Furthermore, tyrosinase, which is the key enzyme for controlling the production of melanin, was inhibited by aloeresin E (109) and isoaloeresin D (110) [82]. The compounds 80–122 are shown in Figure 11, Figure 12 and Figure 13. The sources and the reported biological activities (if any) are summarized in Table 10.

4.3. Phenyl and Isoprenyl Chromone Glycosides

This category is characterized by a hydroxyl prenyl moiety at C-6 or C-8, or a hydroxyl isoprenyl moiety at C-6 only. The sugar moiety can be either situated at C-7 hydroxyl of the chromone nucleus or C-4’ of the hydroxyl prenyl or C-2’ of the hydroxyl isoprenyl moiety. Most of the compounds in this category were reported from the genus Cnidium, belonging to family Apiaceae. The reported biological activity associated with several compounds in this category is their significant inhibition of fat accumulation in differentiated adipocytes employing 3T3-L1 preadipocyte cells as an assay system [60]. The compounds 123–134 are shown in Figure 14. The sources and the reported biological activities (if any) are summarized in Table 11.

4.4. Phenyl Ethyl Chromone Glycosides

Reviewing the literature, we encountered five phenyl ethyl chromone glycosides. The phenyl ethyl moiety is usually located at C-2 of the chromone nucleus. The sugar moiety is attached to C-7 of the chromone skeleton in compounds 135–137, while in compound 138, the sugar is attached to C-8. In compound 139, the sugar is not attached directly to the basic chromone skeleton. Compounds 135–139 are shown in Figure 15. Their sources are summarized in Table 12. There are no reported biological activities of these compounds.

4.5. Chromone Glycosides with Additional Heterocyclic Moieties

This category of chromone glycosides is further classified based on the additional heterocyclic moiety into furano-chromone glycosides, pyrano-chromone glycosides, oxepino-chromone glycosides and pyrido-chromone glycosides.

4.5.1. Furano-Chromone Glycosides

This subclass of compounds is characterized by presence of an additional furan, or a tetrahydrofuran ring fused with the benzo-δ-pyrone. Khellol glucoside (140), isolated from Ammi visnaga, is one of the important members in this subclass. It possess potent coronary vasodilator and bronchodilator activities [115]. It was reported to have a significant hypocholesterolemic effect. It lowered low-density lipoprotein cholesterol (LDL-C) by 73%, high-density lipoprotein cholesterol (HDL-C) by 23%, and total-C by 44%, after a single oral dose of 20 mg/kg per day after two weeks [116]. Compounds 140–148 are shown in Figure 16. The sources and the reported biological activities (if any) are summarized in Table 13.

4.5.2. Pyrano-Chromone Glycosides

This subclass of compounds is characterized by the presence of an additional pyran ring fused with the benzo-δ-pyrone. Only three compounds were reported from nature until now. Of them, 3′-O-glucopyranosylhamaudol (Sec-O-glucopyranosylhamaudol) (149) and (3’S)-3′-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranosylhamaudol (150), isolated from the Saposhnikovia divaricata, showed weak anti-cancer activity. Both compounds were screened against three cancer cell lines, namely human prostatic cancer cell (PC-3), human ovarian carcinoma cell (SK-OV-3), and human lung cancer cell (H460) using the conventional MTT assay. Compound 149 showed a weak activity against H460, with an IC50 value of 94.25 ± 1.45 µM while compound 150, showed an activity against SK-OV-3 with an IC50 value of 86.21 ± 1.03 µM [119]. Compounds 149–151 are shown in Figure 17. The sources and the reported biological activities (if any) are summarized in Table 14.

4.5.3. Oxepino-Chromone Glycosides

This subclass of compounds is characterized by the presence of an additional oxepin fused with the benzo-δ-pyrone. Only four compounds were reported from nature until now, and all of them were reported from Eranthis species. The compounds 152–155 are shown in Figure 18. The sources are summarized in Table 15. There are no reported biological activities for these compounds.

4.5.4. Pyrido-Chromone Glycosides

This subclass includes only the chromone alkaloidal glycoside; Schumanniofoside. This compound was found to reduce the lethal effect of black cobra (Naja melanoleuca) venom in mice [135]. The authors proved that this effect is greatest when the venom is mixed and incubated with the extract or schumanniofoside. They concluded that the mode of action is by oxidative inactivation of the venom. Schumanniophyton magnificum is used extensively in African ethno-medicine for the treatment of various diseases and, most commonly, the treatment of snake bites [135]. Its structure is shown in Figure 19. Its source and biological activity are summarized in Table 16.

4.6. Hybrids of Chromones with Other Classes of Secondary Metabolites

This is an interesting category, as the chromone skeleton is conjugated to another high molecular weight compound, as shown in the following subclasses.

4.6.1. Hybrids of Furano-Chromones with Cycloartane Triterpenes

This subclass of compounds is a hybrid of cycloartane triterpene and chromone. The reported compounds were isolated from the rhizomes of Cimicifuga foetida. The compounds 157–165 are shown in Figure 20. The sources and the reported biological activities (if any) are summarized in Table 17.

4.6.2. Hybrids of Chromones with Secoiridoids

There are only two compounds (Figure 21) belonging to this class, sessilifoside (166) and 7″-O-β-d-glucopyranosylsessilifoside (167). Both compounds were isolated from the roots of Neonauclea sessilifolia roots [41]. The authors did not report biological activities for these compounds.

4.6.3. Chromone Alkaloids Aminoglycosides

This category includes compounds 168–192. Compounds 168–180 were reported from a strain of Streptomyces, isolated from a soil sample. These compounds showed antimicrobial activity against Gram-positive bacteria, as well as a potent antitumor activity. Conversely, compounds 181–183 were isolated from Saccharothrix species, while compounds 184–192 were reported from Actinomycete and exhibited antitumor and antimicrobial activities [137]. Compounds 168–192 are shown in Figure 22 and Figure 23. The sources and the reported biological activities (if any) are summarized in Table 18.

5. Spectroscopic Features

5.1. UV Features

Most of the published work on chromones show several strong bands in the range of 200–320 nm [150,151]. In contrast to chromone, the pyrone ring of 4-chromanone contains no double bond. The ultraviolet absorption spectra of chromones and chromanones are summarized in Table 19 [150].
The UV spectrum of chromones in alcohol shows two strong bands at λmax 245 and 299 nm [152,153,154]. Some data reported three bands at λmax 245, 303 and 297 nm [150]. 2-methyl-5,7-dihydroxy chromone shows bands at λmax 250, 255, 295 and 325 nm, meanwhile 2-methyl-5-hydroxy-7-O-glycosyl chromone shows bands at λmax 248, 255 and 290 nm [154]. The presence of an electron attracting group at C-2 resulted in a bathochromic shift in all bands [151]. The information gained from applying spectral shift reagents with flavonoids can be also applied to chromones. In the case of AlCl3, a bathochromic shift of 20–70 nm, which is non-reversible with acids, indicates a free hydroxyl group at position 5. Meanwhile, a bathochromic shift with NaOAc can be diagnostic for the presence of a free 7-hydroxyl group [154,155].

5.2. IR Features

Carbonyl region: The IR carbonyl stretching frequency for a chromone is observed at 1640~1660 cm−1, which is slightly higher than that of δ-pyrone (1650 cm−l) but is much lower than that of coumarins (1720–1740 cm−l) [25,153]. Despite that the OH group attached to C-5 of the chromone nucleus chelates strongly with the CO group, this intramolecular H-bonding has only a slight bathochromic effect on the CO stretching frequency [156]. All 5-hydroxychromones possess three significant maxima in the 1580–1700 cm−1 region. The two higher frequencies are intense at 1660 and 1630 cm−1, with a constant wavenumber separation of 34 ( ± 5) cm−1 in both carbon tetrachloride and chloroform.
Hydroxyl region: The IR hydroxyl stretching vibration for a chromone was observed at 2500–3650 cm−1. A strong chelation in 5-hydroxychromones does not produce a considerable bathochromic shifts in both the OH and CO stretching bands [156]. Chelated 5-hydroxychromones produce no absorption maxima in the 3300–3600 cm−1 region, but a weak absorption envelope extends from 2400 to 3300 cm−1. The entire envelope is associated with various stretching modes of the chelated 5-OH group [156]. For 7-hydroxychromones, a steric buttressing effect is observed when the 7-OH group is flanked by a bulky substituent in the ortho-position (6 or 8). The free OH band appears as a doublet centered at 3615 cm−1, the separation of the components being ~26 cm−1. When a prenyl moiety is located in the ortho-position to the 7-OH group, an intramolecular OH interaction occurs, resulting in two OH stretching frequencies. When a 7-OH group is flanked by an OMe group, intense intramolecularly bonded OH stretching frequencies are found at ~3513 and 3517 cm−1, respectively [156]. The 2-hydroxymethyl group exhibits a free stretching frequency at ≈3615 cm−1. At concentrations higher than 0.15 M, a broad-bonded OH frequency at 3400 cm−1 occurs due to intermolecular H-bonding, and it consequently disappears on dilution [156].

5.3. 1H-NMR Features

In the following text, we try to give insight about the most characteristic 1H-NMR features of the benzo-δ-pyrone skeleton (Figure 24) and its glycosides. The δ-pyrone ring has two olefinic protons assigned as H-2 and H-3. In 2, 3 unsubstituted chromones, for example compound 12, the 1H-NMR spectrum shows two ortho-coupled doublets (J = 6.0 Hz), located downfield at δH 8.19 (H-2) and upfield at δH 6.26 (H-3) [25]. For 2-alkyl and 2-O-glycosyl chromones (compounds 21 and 1, respectively), they are characterized by an upfield singlet proton (H-3) at δH 6.11 and 5.98, respectively [7,40]. Meanwhile, 3-alkyl and 3-O-glycosyl chromones (compounds 39 and 2, respectively) are characterized by a downfield singlet proton (H-2) at δH 7.93 and 8.07, respectively [10,50].
Chromanone glycosides or 2,3-dihydrochromone glycosides are characterized by an oxygenated proton (H-2) at δH 4.12 and 5.44 as in compounds 62 [63] and 60 [50], respectively. The splitting pattern of H-2 can be either d, dd or ddd, depending on the number of neighboring protons. A small coupling constant between H-2 and H-3 (J= 2.8 Hz) can determine that they are located in the equatorial–equatorial position [50]. Further information on the detailed configuration can be clarified from observing NOESY correlations. Unsubstituted chromanones at C-3, as in 62, show two geminal protons at δH 2.50 and 2.70. Their splitting pattern shows geminal (J3a-3b = 16.2 Hz) and vicinal (Jax-eq = 2.7 Hz or Jax-ax = 12.6 Hz ) couplings [63]. In 3-alkyl substituted chromanones, as in 60 and 61, H-3 is also detected at δH 2.79 [50].
Naturally occurring chromones often bear a hydroxyl or methoxy group at C-5 and/or C-7 and a methyl group at C-2 and/or C-5 [153]. The C-5 methyl is usually observed in 6-C and 8-C glycosides. In aprotic solvents such as DMSO-d6, the chelated 5-OH is detected as a singlet at δH 12.57; meanwhile, the 7-OH is detected at δH 10.00, as in compound 56 [31]. The C-2 methyl in Schumaniofioside A 7 can be detected at δH 2.33 (3H, s) [17]. Meanwhile, those located at C-5, can be detected more downfield at δH 2.64 (3H, s) as in 79 [78].
For the phenyl part of the benzo-δ-pyrone skeleton, the protons show chemical shift and coupling constant values similar to those observed for protons in substituted benzenes.
Sugar moiety: Xylosyl, arabinosyl and glucosyl chromones show an anomeric proton signal at δH ~4.73 (d, J = 7–7.6 Hz) [10,11,12]. The former moieties can be differentiated by the number of the oxygenated protons at the δH 3-5 region, in addition to the difference in 13C-NMR values. Rhamnosyl chromones show a distinct signal at δH ~1.25 (3H, d, J = 6.0 Hz) corresponding to CH3-6’ of α-l-rhamnose [8]. The most abundant chromone of C-glycosides is the 8-C-glycoside form, followed by 6-C-glycosides. However, we encountered a unique 3-C-glycoside named macrolobin 64 [65]. The anomeric proton in macrolobin is detected at δH 5.32 (d, J = 1.5 Hz), the small coupling constant being indicative of the α-anomer [65]. Biflorin 66 and isobiflorin 80, as representative for 6-C and 8-C-glycosides, respectively, show the anomeric proton signal at δH 4.55 (d, J = 9.8 Hz), and 4.63 (d, J = 9.8 Hz), respectively [69]. The former coupling constant value is higher than that observed in case of O-glycosides (J = 7–7.6 Hz) [11,12]. In 5-O, 7-O, 6-C, furano-, pyrano-, oxepino-chromone glycosides, the sugar moiety can be further substituted with another sugar, as in 8–9, 25–32, 78–79, 141–142, 150 and 153, respectively. In 6-C, 8-C and, to a lesser extent, 7-O-glycosides, the sugar moiety can be mono- or disubstituted with a phenolic acid moiety, commonly at C-2’ or C-6’ or C-2’ and C-3’. The most commonly occurring phenolic moiety is gallic acid, but other phenyl propanoids such as cinnamoyl, coumaroyl, feruloyl and coniferoyl moieties also exist. The galloyl moiety is characterized by a singlet aromatic signal integrated for two protons at δH 6.75 [27]. The cinnamoyl moiety is confirmed by two trans-coupled olefinic protons at δH 7.43 (d, J = 15.8 Hz) and 6.25 (d, J = 15.8 Hz), in addition to the aromatic signals of the benzene ring [30]. The presence of coumaroyl substitution is characterized by AA’ BB’ system for two pairs of ortho-coupled aromatic protons at δH 7.31 (2H, d, J = 8.6 Hz) and δH 6.74 (2H, d, J = 8.6 Hz), a trans-olefinic proton signals at δH 7.35 (1H, d, J = 16.1 Hz) and δH 6.03 (1H, d, J = 15.9 Hz) [29].
Prenyl and Isoprenyl chromone glycosides: In the case of 7-O-glycoside 127, hydroxyl prenyl moiety can be easily characterized by the allylic methylene protons at δH 3.53 (2H, m, H-1’), an olefinic proton at δH 5.39 (t, J = 6.4, H-2’), oxygenated methylene protons δH 4.20 and 4.46 (1H each, d, J = 12.0 Hz, H-4’), and an olefinic methyl at δH 1.75 (3H, d, J = 1.2, H-5″) [60]. Its isomeric 4′-O-glycoside 126 showed similar signals; however, the hydroxyl methylene protons (H-4’) were slightly downfield at δH 4.34 and 4.65 due to O-glycosidation [106]. Meanwhile, the hydroxyl isoprenyl group in the 7-O-glycoside 130 is characterized by the methylene protons at δH 2.96 (2H, m, H-1’), an oxygenated methine proton at δH 4.35 (H-2’, m), exomethylene protons at δH 4.74 and 4.91 (H-4’) and an olefinic methyl at δH 1.87 (3H, s, H-5’). Its isomeric 2′-O-glycoside 129 showed similar signals, but the oxygenated methine proton (H-2’) is shifted downfield at δH 4.74 due to O-glycosidation [60].
Phenyl ethyl chromone glycosides: The presence of the phenyl ethyl moiety in compound 136 can be detected by the methylene proton signals at δH 2.75 (2H each, dd, J = 14.8, 6.4 Hz, H-7’) and 3.19 (2H each, J = 14.8, 3.1 Hz, H-8’), in addition to the aromatic protons of the phenyl ring. The 8′-hydroxy phenyl ethyl moiety in 135 shows an oxygenated proton signal δH 5.85 (dd, J = 3.5, 5.9 Hz, H-8’) [110].

5.4. 13C-NMR Features

For better understanding of the differences in chemical shifts related to the substituents on the chromone moiety, we preferred to add the 13C-NMR data in Table 20, Table 21, Table 22, Table 23, Table 24, Table 25, Table 26, Table 27, Table 28, Table 29, Table 30, Table 31, Table 32, Table 33, Table 34, Table 35, Table 36, Table 37, Table 38, Table 39 and Table 40. For the numbering of the skeleton, the following figure (Figure 25) gives few examples for the numbering system of the skeleton with multiple substituents. Briefly, the basic chromone nucleus was assigned numbers 1–10. In the case of a substitution at C-2, numbers 11, 12…etc. were given to the substituents, followed by substitution at C-3 and so on. Sugar moiety, and substituents attached to it, were assigned numbers 1’, 2’, … and then 1″, 2″, … etc. For better understanding, the following figure shows representative examples for the numbering system. Some complicated structures have their own numbering system, shown on them within the review.

6. Conclusions

Chromone glycosides are one of the most important classes of secondary metabolites. In this review, we summarized 192 naturally occurring chromone glycosides with their sources, reported activities, and spectroscopic features. Basically, they were categorized into several classes: chromone-O-glycosides including compounds 1–59, among them, four chromanone glycosides (60–63), chromone-C-glycosides including compounds 64–122, prenyl and isoprenyl chromone glycosides including compounds 123–134, phenyl ethyl chromone glycosides including compounds 135–139, furano-chromone glycosides including compounds 140–148, pyrano-chromone glycosides including compounds 149–151, oxepino-chromone glycosides including compounds 152–155, Pyrido-chromone glycoside including compound 156, furanochromones with cycloartane triterpenes including compounds 157–165, glycoside derivatives of chromones with secoiridoids including compounds 166 and 167, and chromone alkaloids aminoglycosides including compounds 168–192. Diverse bioactivities were discovered for most of the reported chromone glycosides. Several chromone glycosides show potent biological activities as anti-viral, acetylcholinesterase inhibition, anti-tumor, anti-inflammatory, etc. This review directs the attention for further deep investigation of chromone glycosides for drug discovery.

Author Contributions

Y.A.: conceptualization, data collection, writing, reviewing. M.E., A.O. and M.S.: data collection, writing, reviewing. K.S.: supervision, reviewing. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.

Abbreviations

AllAllose
ApiApiose
AraArabinose
CafCaffeic acid
CinCinnamic acid
CouCoumaric acid
FerFerulic acid
GallGallic acid
GluGlucose
RhaRhamnose
XylXylose

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Molecules 26 07646 sch001 550
Scheme 1. Proposed mechanisms for the enzymatic formation of 5,7-dihydroxy-2-methylchromone and its derivatives.
Scheme 1. Proposed mechanisms for the enzymatic formation of 5,7-dihydroxy-2-methylchromone and its derivatives.
Molecules 26 07646 sch001
Molecules 26 07646 sch002 550
Scheme 2. Proposed mechanisms for the enzymatic formation of aloesone and its derivatives.
Scheme 2. Proposed mechanisms for the enzymatic formation of aloesone and its derivatives.
Molecules 26 07646 sch002
Molecules 26 07646 g001 550
Figure 1. Structure of compound 1.
Figure 1. Structure of compound 1.
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Figure 2. Structures of compounds 2–5.
Figure 2. Structures of compounds 2–5.
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Molecules 26 07646 g003 550
Figure 3. Structures of compounds 6–10.
Figure 3. Structures of compounds 6–10.
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Molecules 26 07646 g004 550
Figure 4. Structure of compound 11.
Figure 4. Structure of compound 11.
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Figure 5. Structures of compounds 12–53.
Figure 5. Structures of compounds 12–53.
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Molecules 26 07646 g006 550
Figure 6. Structures of compounds 54–55.
Figure 6. Structures of compounds 54–55.
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Molecules 26 07646 g007 550
Figure 7. Structures of compounds 56–59.
Figure 7. Structures of compounds 56–59.
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Molecules 26 07646 g008 550
Figure 8. Structures of compounds 60–63.
Figure 8. Structures of compounds 60–63.
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Figure 9. Structure of compound 64.
Figure 9. Structure of compound 64.
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Figure 10. Structures of compounds 65–79.
Figure 10. Structures of compounds 65–79.
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Molecules 26 07646 g011 550
Figure 11. Structures of compounds 80–89.
Figure 11. Structures of compounds 80–89.
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Molecules 26 07646 g012 550
Figure 12. Structures of compounds 90–115.
Figure 12. Structures of compounds 90–115.
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Molecules 26 07646 g013 550
Figure 13. Structures of compounds 116–122.
Figure 13. Structures of compounds 116–122.
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Molecules 26 07646 g014 550
Figure 14. Structures of compounds 123–134.
Figure 14. Structures of compounds 123–134.
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Molecules 26 07646 g015 550
Figure 15. Structures of compounds 135–139.
Figure 15. Structures of compounds 135–139.
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Figure 16. Structures of compounds 140–148.
Figure 16. Structures of compounds 140–148.
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Figure 17. Structures of compounds 149–151.
Figure 17. Structures of compounds 149–151.
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Molecules 26 07646 g018 550
Figure 18. Structures of compounds 152–155.
Figure 18. Structures of compounds 152–155.
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Molecules 26 07646 g019 550
Figure 19. Structure of compound 156.
Figure 19. Structure of compound 156.
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Figure 20. Structures of compounds 157–165.
Figure 20. Structures of compounds 157–165.
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Figure 21. Structures of compounds 166–167.
Figure 21. Structures of compounds 166–167.
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Figure 22. Structures of compounds 168–183.
Figure 22. Structures of compounds 168–183.
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Molecules 26 07646 g023 550
Figure 23. Structures of compounds 184–192.
Figure 23. Structures of compounds 184–192.
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Molecules 26 07646 g024 550
Figure 24. Basic skeleton of Chromone.
Figure 24. Basic skeleton of Chromone.
Molecules 26 07646 g024
Molecules 26 07646 g025 550
Figure 25. Representative guide figure for numbering of chromone glycosides attached to different substituents.
Figure 25. Representative guide figure for numbering of chromone glycosides attached to different substituents.
Molecules 26 07646 g025
Table
Table 1. The distribution of chromone glycosides reported through this review.
Table 1. The distribution of chromone glycosides reported through this review.
FamilyGenusSpeciesCompounds
Plants (Angiosperms)1EricaceaeRhododendronovatum2
spinuliferum3
collettianum55
Callunavulgaris13
2RubiaceaeSchumanniophytonmagnificum7, 25, 156
Knoxiacorymbosa20, 24, 35, 36
Adinarubescens20
Neonaucleasessilifolia26, 166
3AmaryllidaceaeGethyllisciliaris10
Pancratiumbiflorum20, 66
maritimum20, 47
4PolygonaceaePolygonumcapitatum15
Rheumaustral50
sp.52, 53
5ApiaceaeAmmivisnaga20, 140, 146
Peucedanumaustriacum20
japonicum149
Cnidiummonnieri57, 58, 123–130
juponicum123, 124
Bupleurumchinense58
Angelicaarchangelica125
genuflexa146, 149
japonica146, 149
Archangelicalitoralis125
Saposhnikoviadivaricata143–146, 149, 150
Ledebouriellaseseloides144
Diplolophiumbuchananii144, 146, 151
Sphallerocarpusgracilis144
Glehnialittoralis149
6HypericaceaeHypericumhenryi22, 23
erectum22, 38
sikokumontanum38, 39, 60, 61
japonicum82, 83
7RanunculaceaeDelphiniumhybridum28
Cimicifugaheracleifolia141
foetida146, 147, 157–165
Eranthishyemalis131, 132, 152, 153, 154
cilicica133, 134, 153, 155
8MyrtaceaeMyrtuscommunis34
Syzygiumaromaticum66, 71, 80, 86
Baeckeafrutescens66, 67, 70, 72, 85, 87
Kunzeaambigua67, 70, 72–74, 80, 85, 88, 89
Eucalyptusglobulus80
maidenii82, 83
grandis83
urograndi83
9FabaceaeCassiamultijuga51, 77
siamea59
obtusifolia68, 69
spectablis78
obtusifolia84
Macrolobiumlatifolium64
Aspalathuslinearis65
Abrusmollis80
Ononisvaginalis135
10AsphodelaceaeAloevera75, 76, 90–98, 103, 104–110, 112–117, 120–122
barbadensis97, 98, 103, 107, 108
rupestris99
cremnophila101
nobilis111, 118, 119
11AraceaeScindapsusofficinalis18–20, 29, 31, 32, 56, 57
12AsteraceaeMutisiaacuminate1
13EucryphiaceaeEucryphiacordifolia4
14SaxifragaceaeAstilbethunbergii4
15SmilacaceaeSmilaxglabra4
16PentaphylaceaeEuryajaponica5
17SalicaceaeSalixmatsudana6
18MeliaceaeDysoxylumbinectariferum7
19EuphorbiaceaeAcalyphafruticose7
20StaphyleaceaeStaphyleabumalda7
21AmaranthaceaeSalicorniaeuropaea12
22AquifoliaceaeIlexhainanensis13
23RosaceaeDasiphoraparvifolia16, 17
24BignoniaceaeTecomellaundulata20, 27
25OlacaceaeScorodocarpusborneensis26
26PinaceaePseudotsugasinensis37
27SelaginellaceaeSelaginellauncinata46, 48
28GentianaceaeSwertiapunicea54
29CannabaceaeHumuluslupulus62
30EuphorbiaceaeChrozophoraprostrata79
31CucurbitaceaeCucumismelo136
32ThymelaeaceaeAquilariasinensis137, 139
33PoaceaeImperatacylindrical138
Ferns1PolypodiaceaeDrynariafortunei7, 28, 30, 32, 33, 57
2DryopteridaceaeDryopterisfragrans20, 21
3OnocleaceaeMatteucciaintermedia49
Lichens Roccellariamollis41, 42, 45
Schismatommaaccedens41, 42, 45
Roccellagalapagoensis41, 42, 45
Lobodirinacerebriformis44
Fungi Armillariatabescens11
Orbiocrellasp.40, 43
Stemphyliumbotryosum63
Actinobacteria Streptomycesphaeoverticillatus var. takatsukiensis168
pluricolorescens169–171
sp.172–178, 180
griseoruber179
Saccharothrixsp.181–183
Actinomycete 184–192
Table
Table 2. 3-O-Chromone glycosides with their sources and biological activities.
Table 2. 3-O-Chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
23,5,7-trihydroxychromone-3-O-
β-d-xylopyranoside		Rhododendron ovatum roots [10]
Eurya japonica stems [11] 		Inhibitory effects on LPS (Lipopolysaccharide)-induced NO (Nitric Oxide) production with inhibition rate 36.24 ± 1.29% at 20 μg/mL [11]
33,5,7-trihydroxylchromone-3-O-
α-l-arabinopyranoside 		Rhododendron spinuliferum aerial
parts [12] 		Inhibition of NO production in LPS-stimulated RAW 264.7 cells with an IC50 value more than 100 mM [12]
4Eucryphin
(5,7-dihydroxy-3-(α-O-l-rhamnopyranosyl)-
4H-l-benzopyran-4-one)		Eucryphia cordifolia bark [8]
Astilbe thunbergii rhizomes [13]		Norepinephrine-enhancing lipolytic effect 6.432 ± 0.014 FFA µmol/mL at 1000 µg [13]
Enhancing effect on burn wound repair at 100 mg ointment per mouse [14]
Smiglanin
(3,5,7-trihydroxychromone-3-O-
α-l-rhamnopyranoside)		Smilax glabra roots [9] No reported biological activity
55,7-Dihydroxy-4H-chromen-4-one-
3-O-β-d-glucopyranoside		Eurya japonica stems [11] Inhibitory effects on LPS-induced NO production with inhibition rate 53.79 ± 1.78% at 20 μg/mL [11]
Table
Table 3. 5-O-Chromone glycosides with their sources and biological activities.
Table 3. 5-O-Chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
6Matsudoside A
(5-β-d-glucosyloxy-7-
hydroxychromone)		Salix matsudana leaves [15]No reported biological activity
7Schumaniofioside A
(2-methyl-5,7-dihydroxychromone
5-O-β-d-glucopyranoside)		Schumanniophyton magnificum
root bark [16]
Dysoxylum binectariferum
fruits [17].
Acalypha fruticose aerial
parts [18,19]
Drynaria fortune rhizomes [13]		Inhibition of proinflammatory cytokines TNF-α (39.51 ± 1.21%) and IL-6 (22.21 ± 0.58%) at 5 μM [17]
Inhibition of NF-kB transcriptional activity and iNOS with IC50 value of 29.5 ± 6.5 µg/mL [19]
8Staphyloside A Staphylea bumalda leaves [20]No reported biological activity
9Staphyloside B
10Isoeugenitol glucosideGethyllis ciliaris
underground parts [21]		No reported biological activity
Table
Table 4. 7-O-Chromone glycosides with their sources and biological activities.
Table 4. 7-O-Chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
127-O-β-d-glucopyranosyl-6-methoxychromoneSalicornia europaea leaves
and stems [25]		No reported biological activity
135,7-dihydroxychromone
7-O-β-d-glucopyranoside		Ilex hainanensis leaves [26]
Calluna vulgaris flowers [27]		No reported biological activity
145,7-dihydroxychromone
7-O-β-d-glucuronide
methyl ester		Davallia mariesii rhizomes [28] No reported biological activity
157-O-(6′-galloyl)-β-d-glucopyranosyl-5-hydroxychromonePolygonum capitatum aerial parts [29]No reported biological activity
165-hydroxy-7-O-(6-O-p-cis-coumaroyl-β-d-glucopyranosyl)-chromoneDasiphora parvifolia aerial parts [30]No reported biological activity
175-hydroxy-7-O-(6-O-p-trans-coumaroyl-β-d-glucopyranosyl)-chromoneDasiphora parvifolia aerial parts [30]No reported biological activity
18Officinaliside AScindapsus officinalis stems [31]No reported biological activity
197-O-α-l-rhamnosyl-nereugeninScindapsus officinalis stems [31]No reported biological activity
20Undulatoside A
(2-methyl-5,7-dihydroxychromone
7-O-β-d-glucopyranoside)		Scindapsus officinalis stems [31]
Ammi visnaga fruits [32]
Knoxia corymbosa [33]
Pancratium biflorum roots [34]
Panacratium biflorum flowering
bulbs [35]
Pancratium maritimum L. fresh
bulbs [36]
Peucedanum austriacum [37]
Tecomella undulata bark [38]
Adina rubescens leaves [39]
Dryopteris fragrans [40]
Staphylea bumalda leaves [20]		Immunomodulatory activity inhibited the proliferation of murine B lymphocytes in vitro at 10−5 M [33]
Inhibition of nitric oxide
production in lipopolysaccharide induced RAW 264.7 macrophages
with an IC50 value of 49.8 μM [40]
Weak antimigratory activity against human metastatic prostate cancer cells (PC-3M) at 50 µM [36]
21Frachromone C
(5-hydroxy-2-ethylchromone-7-O-β-d-glucopyranoside)		Dryopteris fragrans whole plant [40]Inhibition of nitric oxide
production in lipopolysaccharide induced RAW 264.7 macrophages
with an IC50 value of 45.8 μM [40]
22Urachromone A
(5-hydroxy-2-isopropylchromone-7-O-β-d-glucopyranoside)		Hypericum henryi aerial parts [41]
Hypericum erectum [42]		No reported biological activity
Hyperimone A
23Urachromone BHypericum henryi aerial parts [41]No reported biological activity
24Corymbosin K2
(7-O-β-d-6-
acetylglucopyranosyl-5-hydroxy-2-methylchromone)		Knoxia corymbosa [33]Immunomodulatory activity inhibited the proliferation of murine B lymphocytes in vitro at 10−5 M [33]
25Schumanniofioside BSchumanniophyton magnificum root bark [16]No reported biological activity
265-hydroxy-2-methylchromone-7-O-β-d-apiofuranosyl-(1→6)- β-d-glucopyranosideNeonauclea sessilifolia roots [43]
Scorodocarpus borneensis leaves [44]
Staphylea bumalda leaves [20]		No reported biological activity
27Undulatoside BTecomella undulata [45] No reported biological activity
282-methyl-chromone-5,7-diol 7-O-α-l-rhamnopyranosyl-(1-6)-β-d-glucopyranosideDelphinium hybridum aerial parts [46]
Drynaria fortunei rhizomes [22]		No reported biological activity
29Officinaliside C
(7-O-[β-d-glucopyranosyl-(1-2)-α-l-rhamnopyranosyl]-5-hydroxy-2-methyl-4H-1-benzopyran-4-one)		Scindapsus officinalis stems [31]No reported biological activity
30Drynachromoside C
(5-hydroxy-2-methyl
chromone-7-O-β-d-glucopyranosyl
(1-3)-α-l-rhamnopyranoside)		Drynaria fortunei rhizomes [22]Inhibitory activity on triglyceride accumulation at 10 μM [22]
31Officinaliside B
(7-O-[6-acetyl-β-d-glucopyranosyl-(1-3)-α-l-rhamnopyranosyl]-5-hydroxy-
2-methyl-4H-1-benzopyran-4-one)		Scindapsus officinalis stems [31]Inhibition of NO production in LPS-stimulated RAW 264.7 cells with an IC50 value of 16.1 μM [31]
32Drynachromoside A
(5-hydroxy-2-methyl-4H-benzopyran-4-one-7-O-β-d-glucopyranosyl-(1-4)-α-l-rhamnopyranoside)		Scindapsus officinalis stems [31]
Drynaria fortunei rhizomes [47]		Proliferative activity 10.1% on MC3T3-E1 (Mouse osteoblast) cells at 25 μg/mL [47]
33Drynachromoside D
(5-hydroxy-2-methyl
chromone-7-O-α-l-arabinopyranosyl(1-2)-β-d-glucopyranosyl(1-4)-α-l-rhamnopyranoside)		Drynaria fortunei rhizomes [22]Inhibitory activity on triglyceride accumulation (inhibited PPARγ, C/EBPα and aP2 expression by 50%, 43% and 37% at 10 mM) [22]
34Undulatoside A 6′-O-gallateMyrtus communis leaves [48]
35Corymbosin K3 (7-O-[6-O-(4-O-trans-caffeoyl-β-d-allopyranosyl)]-β-d-glucopyranosyl-5-hydroxy-2-
methylchromone)		Knoxia corymbosa [33]Immunomodulatory activity inhibited the proliferation of murine B lymphocytes in vitro at 10−5 M [33]
367-O-[6-O-(4-O-trans-feruloyl-β-d-allopyranosyl)]-
β-d-glucopyranosyl-5-hydroxy-2-methylchromone		Knoxia corymbosa [33]No reported biological activity
375-hydroxy-6-methylchromone-7-O-β-d-glucopyranosidePseudotsuga sinensis [49]No reported biological activity
38Takanechromone A
(5,7-dihydroxy-3-methylchromone-
7-O-β-d-glucopyranoside) 		Hypericum sikokumontanum
aerial parts [50]
Hypericum erectum [42]		No reported biological activity
Hyperimone B
39Takanechromone B
(5,7-dihydroxy-3-ethylchromone-
7-O-β-d-glucopyranoside) 		Hypericum sikokumontanum
aerial parts [50]		No reported biological activity
407-O-(4-O-Methyl-β-d-glucopyranosyl)eugenitolThe scale-insect pathogenic fungus Orbiocrella sp. [23]No reported biological activity
41MollinLichens (Roccellaria mollis, Schismatomma accedens, Roccella galapagoensis) [51]No reported biological activity
42RoccellinLichens (Roccellaria mollis, Schismatomma accedens, Roccella galapagoensis) [51]No reported biological activity
437-O-(4-O-Methyl-β-d-glucopyranosyl)isoeugenitolThe scale-insect pathogenic fungus Orbiocrella sp. [23]No reported biological activity
44LobodirinLobodirina cerebriformis lichen [51]No reported biological activity
45GalapaginLichens (Roccellaria mollis, Schismatomma accedens, Roccella galapagoensis) [51]No reported biological activity
46Uncinoside A (5-hydroxy-2,6,8-
trimethylchromone 7-O-β-d-glucopyranoside)		Selaginella uncinate Herb [24]Antiviral activity against respiratory syncytial virus (RSV) with an IC50 value of 6.9 μg/mL, against parainfluenza type 3 virus (PIV 3) with an IC50 value of 13.8 μg/mL [24]
47PancrichromonePancratium maritimum L. fresh bulbs [36]No reported biological activity
48Uncinoside B (5-acetyoxyl-2,6,8-trimethylchromone 7-O-β
-d-glucopyranoside)		Selaginella uncinate herb [24]Antiviral activity against respiratory syncytial virus (RSV) with an IC50 value of 1.3 μg/mL, against parainfluenza type 3 virus (PIV 3) with an IC50 value of 20.8 μg/mL [24]
49Matteuinterin BMatteuccia intermedia rhizomes [52]
502,5-dimethylchromone-7-O-β-d-glucopyranosideRheum austral D. Don underground parts [53]
Rumex gmelini Turcz. roots [54]		Anti-oxidant activity (DPPH radical scavenging capacity with an IC50 value of 66.9 ± 1.3 μM) [53]
515-acetonyl-7-β-d-glucopyranosyl-2-methylchromoneCassia multijuga leaves [55,56]No reported biological activity
522-methyl-5-(2′-oxo-4′-hydroxyphenyl)-7-hydroxychromone 7-O-β-d-glucopyranosideChinese rhubarb (Rhei Rhizoma) [57]No reported biological activity
53Aloesone 7-O-β-d-glucopyranosideChinese rhubarb (Rhei Rhizoma) [57]No reported biological activity
Table
Table 5. 8-O-Chromone glycosides with their sources and biological activities.
Table 5. 8-O-Chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
548-O-β-d-Glucopyranosyl-2-methylchromoneSwertia punicea whole herb [58]No reported biological activity
558-O-β-d-Glucopyranosyl-6-hydroxy-2-methyl-4H-1-benzopyrane-4-one Rhododendron collettianum aerial parts [59]Inhibitory activity against tyrosinase enzyme with an IC50 value of 256.97 μM [59]
Table
Table 6. 11, 13-O-chromone glycosides with their sources and biological activities.
Table 6. 11, 13-O-chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
56Officinaliside D
(2-hydroxymethyl-5,7-dihydroxy-4H-benzopyran-4-
one-1′-O-α-l-arabinopyranoside)		Scindapsus officinalis stems [31]Inhibition of NO production in LPS-stimulated RAW 264.7 cells with an IC50 value of 19.1 µM [31]
57Drynachromoside BDrynaria fortune rhizomes [22,47]
Scindapsus officinalis stems [31]		Mild inhibitory activity against MC3T3-E1 (mouse osteoblast) cells at 3.125 to 100 μg/ml [47]
Triglyceride accumulation inhibitory effect at 0.1 to 10 μM [22]
Monnieriside ACnidium monnieri fruits [60] No reported biological activity
58Saikochromoside ABupleurum chinense [61]
Cnidium monnieri fruits [60]		No reported biological activity
592-Methyl-5-propyl-7,12-
dihydroxychromone-12-O-β-d-glucopyranoside		Cassia siamea stem [62]No reported biological activity
Table
Table 7. Chromanone glycosides with their sources and biological activities.
Table 7. Chromanone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
60Takanechromanone AHypericum sikokumontanum aerial
parts [50]		Anti-Helicobacter pylori at 100 µg/disc [50]
61Takanechromanone B
625-β-d-glucopyranosyloxy-7-hydroxy-2-isopropyl-chromanoneHumulus lupulus L. bracts [63]No reported biological activity
63Stemphylin
(3-hydroxy-2, 2-dimethyl-5-α-d-glucopyranoside-2, 3-dihydrochromone)		The liquid culture of the fungus Stemphylium botryosum [64]Phytotoxic activity [64]
Table
Table 8. 3-C-Chromone glycoside with its source and biological activities.
Table 8. 3-C-Chromone glycoside with its source and biological activities.
No.CompoundSourceBiological Activity
64Macrolobin
(5,7-dihydroxychromone-
3α-d-C-glucoside)		Macrolobium latifolium aerial parts [65]Inhibition of acetylcholinesterase enzyme with an IC50 value of 0.8 μM
Antimicrobial activity against P. aeruginosa and Salmonella at 0.73 and 0.44 μM, respectively [65]
Table
Table 9. 6-C-Chromone glycosides with their sources and biological activities.
Table 9. 6-C-Chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
655,7-dihydroxy-6-C-glucosyl-chromoneAspalathus linearis fermented
rooibos (red-brownish dry leaves) [66]		No reported biological activity
66Biflorin
(6-β-C-glucopyranosyl-5,7-dihydroxy-2-methylchromone)		Pancratium Biflorum roots [34]
Syzygium aromaticum L. flower
buds [67,68]
Baeckea frutescens leaves [69,70] 		Inhibitory activity to
phosphodiesterase and spared cyclic nucleotides at 10−9 M [34]
Inhibition of LPS-induced production of nitric oxide (NO) and prostaglandin E2 (PGE2) in RAW 264.7 macrophages with
IC50 values of 51.7 and 37.1 μM, respectively [67]
676-β-C-glucopyranosyl-
5,7-dihydroxy-2-isopropylchromone 		Baeckea frutescens leaves [69,70]
Kunzea ambigua leaves [71] 		Inhibitory activity 70.4% against EBV-EA (Epstein–Barr virus early antigen) activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA) at 500 mol ratio/TPA [71]
68Obtusichromoneside CCassia obtusifolia seeds [72]Weak inhibitory activity against human organic anion/cation transporters (OATs/OCTs) and organic anion transporting polypeptides (OATPs) at 50 μM [72]
69Obtusichromoneside A
70Kunzeachromone CKunzea ambigua leaves [71]
Baeckea frutescens leaves [70] 		Inhibition of copper-induced LDL oxidation with an IC50 value of 3.35 ± 0.36 μM [70]
716-C-β-d-(6′-O-galloyl)glucosylnoreugeninSyzygium aromaticum flower
buds [68,73] 		Cytotoxicity against human ovarian cancer cells (A2780) with an IC50 value of 66.78 ± 5.49 μM [68]
Prolyl endopeptidase inhibitory effects with an IC50 value of 1.74 ± 0.03 μM [73]
726-β-C-(2′-O-galloylglucopyranosyl)-5,7-dihydroxy-
2-isopropylchromone		Baeckea frutescens leaves [69,70]
Kunzea ambigua leaves [71]		Inhibitory activity 68.4% against EBV-EA activation induced by TPA at 500 mol ratio/TPA [71]
Inhibition of copper-induced LDL oxidation with an IC50 value of 3.90 ± 0.24 μM [70]
73Kunzeachromone DKunzea ambigua leaves [71]No reported biological activity
74Kunzeachromone A
75Aloeveraside BAloe vera resin [74,75,76]Inhibition of urease enzyme (55% and 62%, respectively) at 1 mg/mL concentration, significant growth inhibition (70.5 and 76.4%) of the breast cancer cell line MDA-MB-231 at 100 μM, and antioxidant (80% and 60%) at 1 mg/mL [74]
Anti-lipid peroxidation activity with IC50 values of 432.1 ± 0.6 and 469.5 ± 0.4 µmol/L, respectively [75]
76Aloeveraside A
77Acetonyl-6-glycosyl -7-hydroxy -2-methylchromoneCassia multijuga leaves [55,56]No reported biological activity
785-acetonyl-7-hydroxy-6-C-glucopyranosyl-2-methyl chromone
2″-O-glucopyranoside		Cassia spectablis seeds [77]No reported biological activity
792-acetonyl-5-methyl-7-hydroxy-6-C-glucopyranosyl
chromone
2″-O-glucopyranoside		Chrozophora prostrata roots [78]No reported biological activity
Table
Table 10. 8-C-Chromone glycosides with their sources and biological activities.
Table 10. 8-C-Chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
80IsobiflorinAbrus mollis Hance. aerial parts [83]
Syzygium aromaticum L. flower
buds [67]
Kunzea ambigua (SM.) Druce.
leaves [71]
Eucalyptus globulus leaves [84,85]
Eugenia caryophyllata flower
buds [86]		Inhibition of LPS-induced production of nitric oxide (NO) with an IC50 > 60 μM and prostaglandin E2 (PGE2) ) with an IC50 value of 46.0 μM [67]
817-methoxy-isobiflorinZhuyeqing Liquor; a famous
traditional Chinese functional
health liquor [87]		No reported biological activity
825,7-Dihydroxy-2-isopropylchromone-
8-β-d-glucoside		Hypericum japonicum aerial
parts [71,88,89]
Eucalyptus maidenii bark [84]		Inhibit Epstein–Barr virus early antigen induced by 12-O-tetradecanoylphorbol 13-acetate (TPA) in Raji cells (70.4%) at 500 mol ratio/TPA [71]
835,7-Dihydroxy-2-(1-methylpropyl) chromone-8-β-d-glucoside
Hypericum japonicum aerial
parts [71,88]
Eucalyptus grandis,
Eucalyptus urograndi, and
Eucalyptus maidenii bark [90]		No reported biological activity
84Obtusichromoneside BCassia obtusifolia seeds [72]Inhibitory activity against human organic anion/cation transporters (OATs/OCTs) and organic anion transporting polypeptides (OATPs) at 50 μM [72]
85Kunzeachromone E
[8-β-C-(2′-galloylglucopyranosyl)-
5,7-dihydroxy-2-methylchromone]		Kunzea ambigua leaves [71]
Baeckea frutescens leaves [70]		Inhibition activity toward copper-induced LDL oxidation with IC50 value of 3.98 ± 0.24 µM [70]
868-C-β-d-(6′-O-galloyl)glucosylnoreugenin
[2-Methyl-5,7-dihydroxy-chromone-8-β-d-(6′-O-galloyl)-glucopyranoside]		Syzygium aromaticum L. leaves [91]
Syzygium aromaticum L. flower
buds [68,73]		Cytotoxicity against human ovarian cancer cells (A2780) with an IC50 value of 87.50 ± 1.56 µM [68]
Significant inhibition capacity against Prolyl Endopeptidase with IC50 value of 1.48 ± 0.02 µM [73]
878-β-C-(2′-galloylglucopyranosyl)-5,7-dihydroxy-2-isopropylchromoneBaeckea frutescens leaves [70]Active against copper-induced LDL oxidation with an IC50 value of 3.91 ± 0.18 µM [70]
88Kunzeachromone F
[2-Methyl-5,7-dihydroxy-chromone-8-β-d-(2’,3′-di-O-galloyl)-glucopyranoside]		Kunzea ambigua leaves [71]No reported biological activity
89Kunzeachromone B
[2-Isopropyl-5,7-dihydroxy-chromone-8-β-d-(2’,3′-di-O-galloyl)-glucopyranoside]		Kunzea ambigua leaves [71]No reported biological activity
902,5-dimethyl-8-C-β-d-glucopyranosyl-7-hydroxy-chromoneAloe vera [92]No reported biological activity
912-(E)-propenyl-7-
methoxy-8-C-β-d-glucopyranosyl-5-methylchromone		Aloe vera [76,80]BACE1 (β-secretase) inhibitory activity with an IC50 value of 20.5 µM [80]
928-C-β-d-glucosyl-(R)-aloesolAloe vera [76,80]BACE1 (β-secretase) inhibitory activity (39.2%) at 100 μM [80]
938-C-β-d-glucosyl-7-O-methyl-(R)-aloesolAloe vera [76,80] and anerobic
incubation of aloesin with
bacterial mixture [93]		BACE1 (β-secretase) inhibitory activity (26.8%) at 100 μM [80]
948-C-β-d-glucosyl-(S)-aloesolAloe vera [76] and anerobic
incubation of aloesin with
bacterial mixture [93]		No reported biological activity
958-C-β-d-glucosyl-7-O-methyl-(S)-aloesolAloe vera [76] and anerobic
incubation of aloesin with
bacterial mixture [93]		No reported biological activity
968-C-β-d-glucosyl-7-O-methylaloediolAloe vera [76,80]No reported biological activity
97Neoaloesin AAloe vera [76]
Aloe barbadensis leaves [94]		No reported biological activity
98AloesinAloe vera [76,80]
Aloe barbadensis leaves [95] 		Antioxidant activity (50 ± 1 μM trolox equivalent) at 100 mg of soluble solid/L solution [95]
BACE1 inhibitory activity (37.5%) at 100 μM [80]
Suppresses hyperpigmentation (40%) at 100 mg⁄g polyethylene glycol [2]
997-O-methylaloesinAloe rupestris leaves exudate [96]No reported biological activity
100Aloesin-2″,3″,4″,6″-tetra-O-acetateAnerobic incubation of aloesin
with bacterial mixture [93]		No reported biological activity
1012″-O-tigloylaloesinAloe cremnophila leaves exudate [97]No reported biological activity
1028-C-β-d-glucopyranosyl-7-hydroxy-5-methylchromone-2-carboxylic acidHerbal tea “muti” [98]No reported biological activity
1038-[C-β-d-[2-O-(E)-cinnamoyl]glucopyranosyl]-2-[(R)-2-hydroxypropyl]-7-methoxy-5-methylchromone Aloe vera [76]
Aloe barbadensis leaves [99]		Topical anti-inflammatory activity at 200 µg/ear [99]
104Aloeresin DAloe vera [76]No reported biological activity
105RabaichromoneAloe vera [76]No reported biological activity
106Allo-aloeresin DAloe vera [76]No reported biological activity
107Aloeresin KAloe vera [76]
Aloe barbadensis leaf skin [100]		No reported biological activity
108Aloeresin JAloe vera [76]
Aloe barbadensis leaf skin [100]		No reported biological activity
109Aloeresin EAloe vera leaves [76,82]Inhibition of tyrosinase enzyme (40% and 80% at 50 and 100 ppm, respectively) [82]
110Isoaloeresin DAloe vera leaves [76,82]Inhibition of tyrosinase enzyme (20% and 40% at 50 and 100 ppm, respectively) [82]
Antiviral activity against Pepper mild mottle virus; PMMoV (37.5 ± 6.5% at 1.5 mg/mL) [81]
1112′-O-[p-methoxy-(E)-cinnamoyl]-(S)-aloesinolAloe nobilis leaves [12]BACE1 inhibitory activity (34.1%) at 100 μM [80]
112Iso-rabaichromoneAloe vera [76,82]No reported biological activity
1138-C-glucosyl-(2′-O-cinnamoyl)-7-O-methylaloediol BAloe vera leaves [76]No reported biological activity
114Aloeresin AAloe vera [76]Antioxidant activity [101]
α-glucosidase inhibitory activities, with IC50 values of 11.94 and 2.16 mM against rat intestinal sucrase and maltase [79]
1157-O-methyl-aloeresin AAloe vera [76]Tyrosinase inhibitory activity with an IC50 value of 9.8 μM [81]
1166′-O-coumaroyl-aloesinAloe vera [76]Anti-lipid peroxidation activity with an IC50 value of 476.4 ± 0.9 µM [75]
1177-Methoxy-6′-O-coumaroyl-aloesinAloe vera [76]Weak anticancer activity against breast cancer cell line, MDA-MB-231 (induce 30% decline in cell survival at 25 μM ) [102]
1182′-FeruloylaloesinAloe nobilis leaves [80]Inhibition activity against β-secretase (36.4%) at 100 μM [80]
Inhibition effect against mushroom tyrosinase (27 ± 0.57%) at 0.4 μM [103]
1192′-Feruloyl-7-O-methylaloesinAloe nobilis leaves [80]Inhibition activity against BACE1 (β-secretase) (48.7%) at 100 μM [80]
1209-Dihydroxyl-2′-O-(Z)-cinnamoyl-7-methoxy-aloesinAloe vera [76]Inhibition of tyrosinase enzyme (9.5 ± 9.0%) at 100 μM
Antiviral against Pepper mild mottle virus; PMMoV (31.5 ± 4.2% inhibition at 1.5 mg/mL) [81]
1214′-O-β-d-glucosyl-isoaloeresin DIAloe vera [76]No reported biological activity
1224′-O-β-d-glucosyl-isoaloeresin DIIAloe vera [76]No reported biological activity
Table
Table 11. Prenyl and isoprenyl chromone glycosides with their sources and biological activities.
Table 11. Prenyl and isoprenyl chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
123Cnidimoside ACnidium Juponicum whole
plant [104,105]
Cnidium monnieri fruits [60,106]		Significant
inhibition of fat accumulation at 300 μM in differentiated adipocytes [60]
Antitumor and antimetastatic actions at 0.1–100 μM (in vitro) and 20, 50 mg/kg, twice daily (in vivo) [105]
124Cnidimoside BCnidium Juponicum whole plant [104]
Cnidium monnieri fruits [60]		Significant ihibition of fat accumulation at 300 μM in differentiated adipocytes [60]
1252-methyl-5-hydroxy-6-(2-
butenyl-3-hydroxymethyl)-7-(β-d-glucopyranosyloxy)-4H-
1-benzopyran-4-one		Cnidium monnieri fruits [60]
Angelica archangelica [107]
Archangelica litoralis [107]		No reported biological activity
126Hydroxycnidimoside ACnidium monnieri fruits [60,106]Significant inhibition of fat accumulation at 300 μM in differentiated adipocytes [60]
127Monnieriside BCnidium monnieri fruits [60,106]
128Monnieriside CCnidium monnieri fruits [60]No reported biological activity
129Monnieriside D
130Monnieriside E
1317,8-Secoeranthin-β-d-glucopyranoside (8-{(2E)-4-[β-d-glucopyranosyl)oxy]-3-methylbut-2-enyl}-5,7-
dihydroxy-2-methyl-4H-l-benzopyran-4-one)		Eranthis hyemalis tubers [108] No reported biological activity
1322-C-Hydroxy-7,8-seroeranthipn-β-d-glucopyranoside (8-{(2E)-4-[β-d-glucopyranosyl)oxy]-3-methylbut-2-enyl}-5,7-
dihydroxy-2-(hydroxymethyl)-4H-1-benzopyran-4-on2)
1337-[(β-d-glucopyranosyl)oxy]-5-hydroxy-8-[(2E)-4-hydroxy-3-methylbut-2-enyl]-2-methyl-4H-1-benzopyran-4-oneEranthis cilicica tubers [109]
No reported biological activity
1347-[(β-d-glucopyranosyl)oxy]-5-hydroxy-2-hydroxymethyl-8-
[(2E)-4-hydroxy-3-methylbut-2-enyl]-4H-1-benzopyran-4-one
Table
Table 12. Phenyl ethyl chromone glycosides with their sources.
Table 12. Phenyl ethyl chromone glycosides with their sources.
No.CompoundSource
135Ononin glucosideOnonis vaginalis whole plant [110]
1367-Glucosyloxy-5-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone Cucumis melo seeds [111]
137Aquilarinoside C (6,4′-dimethoxy-3′-hydroxy-2-
(2-phenylethyl)chromone 7-O-β-d-glucopyranoside)		Aquilaria sinensis stems [112]
1382-(2-phenylethyl) chromone-8-O-β-d-glucopyranosideImperata cylindrical rhizomes [113]
1392-[2-(4-glucosyloxy-3-methoxyphenyl)ethyl]chromoneAquilaria sinensis resinous heartwood [114]
Table
Table 13. Furano-chromone glycosides with their sources and biological activities.
Table 13. Furano-chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
140Khellol glucoside (Khellinin;
Khelloside)		Ammi visnaga fruits [117]
Eranthhis hyernalis tubers [108]		Potent coronary vasodilator and bronchodilator [115]
Hypocholesterolemic effect at 20 mg/kg per day [116]
141Norkhelloside Cimicifuga heracleifolia
rhizomes [118]		No reported biological activity
1427-[(O-β-d-glucopyranosyl-(1→6)-
β-d-glucopyranosyl)oxy]methyl-4-hydroxy-5H-furo[3,2-g][1]benzopyran-5-one		Eranthis cilicica tubers [109]No reported biological activity
1434′-O-β-d-glucopyranosylvisamminol
(Monnieriside G)		Cnidium monnieri fruits [60]
Saposhnikovia divaricata roots [119]		Antitumor activity against SK-OV-3 with an IC50 value of 93.91 μM [120]
1444′-O-β-d-glucopyranosyl-5-O-methylvisamminolLedebouriella seseloides roots and
rhizomes [121]
Saposhnikovia divaricata
roots [119,122]
Diplolophium buchananii aerial
parts [123]
Sphallerocarpus gracilis roots [124]		Analgesic, antipyretic, anti-inflammatory, and anti-platelet aggregation activities [125,126]
Antitumor activity with against H-460 cell line with an IC50 value of 86.91 μM [120]
145(2’S)-4′-O-β-d-apiofuranosyl-
(1→6)-β-d-glucopyranosylvisamminol		Saposhnikovia divaricata roots [119]Antitumor activities against PC-3 and SK-OV-3 cell lines with IC50 values of 48.5, 81.91 μM, respectively [120]
146prim-O-glucosylcimifuginAmmi visnaga fruits [127]
Angelica genuflexa roots [128]
Eranthis hyernalis tubers [108]
Angelica japonica roots [129]
Cimicifuga foetida rhizomes [130]
Diplolophium buchananii aerial
parts [123]
Saposhnikovia divaricata roots [131]		Analgesic, antipyretic, anti-inflammatory, anti-platelet aggregation and antitumor activities [125,126,131]
147Cimifugin-4′-O-[6″-feruloyl]-β-d-glucopyranosideCimicifuga foetida rhizomes [132]No reported biological activity
148Monnieriside FCnidium monnieri fruits [60]No reported biological activity
Table
Table 14. Pyrano-chromone glycosides with their sources and biological activities.
Table 14. Pyrano-chromone glycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
1493′-O-glucopyranosylhamaudol
(Sec-O-glucopyranosylhamaudol)		Angelica genuflexa roots [128]
Angelica japonica roots [129]
Glehnia littoralis roots [133]
Peucedanum japonicum roots [134]
Saposhnikovia divaricata
roots [119,122]		Antitumor activity against H-460 cell line with an IC50 value of 94.25 ± 1.45 μM [119]
150(3’S)-3′-O-β-d-apiofuranosyl-(1→6)-
β-d-glucopyranosylhamaudol		Saposhnikovia divaricata roots [119]Antitumor activity against SK-OV-3 with an IC50 value of 86.21 ± 1.03 μM [119]
151(2’S)-2′-hydroxy-7-O-methylallopeucenin
2′-O-β-d-glucopyranoside		Diplolophium buchananii
aerial parts [123]		No reported biological activity
Table
Table 15. Oxepino-chromone glycosides with their sources.
Table 15. Oxepino-chromone glycosides with their sources.
No.CompoundSource
152Eranthin β-d-glucopyranosideEranthis hyemalis tubers [108]
153Eranthin β-d-gentiobiosideEranthis cilicica tubers [109]
Eranthis hyemalis tubers [108]
1542-C-Hydroxyeranthin β-d-glucopyranosideEranthis hyemalis tubers [108]
1559-[(O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]methyl-8,11-dihydro-5,9-dihydroxy-2-methyl-4Hpyrano[2,3-g][1]benzoxepin-4-oneEranthis cilicica tubers [109]
Table
Table 16. Pyrido-chromone glycosides with its source and biological activity.
Table 16. Pyrido-chromone glycosides with its source and biological activity.
No.CompoundSourceBiological Activity
156SchumanniofosideSchumanniophyton magnificum stem bark [135]Anti-snake venom activity at 0.01–0.16 g/kg [135]
Table
Table 17. Hybrids of furanochromones with cycloartane triterpenes with their sources and biological activities.
Table 17. Hybrids of furanochromones with cycloartane triterpenes with their sources and biological activities.
No.CompoundSourceBiological Activity
157Cimitriteromone ACimicifuga foetida rhizomes [130]No reported biological activity
158Cimitriteromone BCimicifuga foetida rhizomes [130]Anti-proliferative activity with an IC50 value of 15.73 ± 0.59 μM [130]
159Cimitriteromone CCimicifuga foetida rhizomes [130]No reported biological activity
160Cimitriteromone DCimicifuga foetida rhizomes [130]Anti-proliferative activity with an IC50 value of 24.21 ± 0.61 μM [130]
161Cimitriteromone ECimicifuga foetida rhizomes [130]No reported biological activity
162Cimitriteromone FCimicifuga foetida rhizomes [130]No reported biological activity
163Cimitriteromone GCimicifuga foetida rhizomes [130]No reported biological activity
164Cimitriteromone HCimicifuga foetida rhizomes [136]No reported biological activity
165Cimitriteromone ICimicifuga foetida rhizomes [136]Anti-proliferative activity with an IC50 value of 27.14 ± 1.38 μM [136]
Table
Table 18. Chromone alkaloids aminoglycosides with their sources and biological activities.
Table 18. Chromone alkaloids aminoglycosides with their sources and biological activities.
No.CompoundSourceBiological Activity
168Kidamycin (rubiflavin B)Streptomyces phaeoverticillatus var.
takatsukiensis [138]		Antibiotic with MIC (minimum inhibitory concentration) ranges from 0.19–1.56 μg/mL and potent antitumor activity [138]
169NeopluramycinStreptomyces pluricolorescens [139,140]Antibiotics and potent antitumor activity [140]
17014, 16-EpoxykidamycinStreptomyces pluricolorescens [141]Antibiotic against Gram-positive bacteria with MIC ranges from 0.5 to 10 μg/mL and antitumor activity [141]
171Pluramycin AStreptomyces pluricolorescens [139,140]Antibiotic and antitumor activity [140]
172Rubiflavin AStreptomyces species [142]Antibiotic and antitumor activity [142]
173Rubiflavin C-1
174Rubiflavin C-2
175Rubiflavin D
176Rubiflavin E
177Rubiflavin F (isokidamycin)
178PD 121,222Streptomyces species [143]Antibiotic and potent antitumor activity [143]
179HedamycinStreptomyces griseoruber [144,145]Antibiotic and potent antitumor activity against HeLa cells [144]
180Ankinomycin (deangolosaminylhedamycin)Streptomyces species [146]Antibiotic against Gram-positive bacteria with MICs ranges from 0.39–1.56 μg/mL and potent antitumor activity [146]
181Pluraflavin ASaccharothrix species [147]Antibiotic and potent antitumor activity [147]
182Pluraflavin B
183Pluraflavin E
184Altromycin AActinomycete, AB 1246E-26 [148,149]Antibiotic against Gram-positive bacteria and potent antitumor activity [137]
185Altromycin B
186Altromycin C
187Altromycin D
188Altromycin EActinomycete, AB 1246E-26 [137]
189Altromycin F
190Altromycin G
191Altromycin H
192Altromycin I
Table
Table 19. UV Band maxima of chromones and chromanone in 3-methylpentane at 25 °C.
Table 19. UV Band maxima of chromones and chromanone in 3-methylpentane at 25 °C.
ChromonesChromanones
Band systemλmaxλmax
A360, 352, 345, 337, 324363, 347
322(sh), 312
252, 246
219(sh), 213
B301, 290, 283
C225, 246, 239, 227, 223, 216, 202
Table
Table 20. The 13C-NMR spectral data of compounds 1–14 except those which have no reported 13C-NMR data.
Table 20. The 13C-NMR spectral data of compounds 1–14 except those which have no reported 13C-NMR data.
C123457111314
2161.2147.4147.7147.8147.4167.2167.8158.6159.5
393.1141.2141.0138.1141.5111.7109.1112.0112.8
4166.6178.4178.5177.0178.4180.3183.2183.6184.4
5137.1163.4163.3161.5163.4160.293.9163.4163.9
6132.0100.1100.298.8100.2104.6162.0101.3101.9
7127.8166.4166.3164.3166.5164.7110.2164.9165.2
8114.995.095.093.895.099.1159.696.296.9
9154.3159.3159.3157.2159.4161.1156.6159.5160.2
10114.5106.2106.2104.8106.1109.2106.1108.4109.3
1123.2----19.920.3--
12------8.2--
1′100.1104.6104.4100.6104.2105.0101.7101.6102.1
2′73.274.672.069.974.874.675.174.775.1
3′77.577.173.670.277.477.378.477.977.8
4′69.670.869.271.571.371.380.571.273.9
5′76.767.167.169.778.578.778.178.477.5
6′60.7--17.762.662.560.962.4171.5
OCH3--------53.8
SolventDMSO-d6CD3ODCD3ODDMSO-d6CD3ODCD3ODC5D5NCD3ODCD3OD
References[7][10][12][9][11][17][1][27][28]
Table
Table 21. The 13C-NMR spectral data of compounds 15–23 except which has no reported 13C-NMR data.
Table 21. The 13C-NMR spectral data of compounds 15–23 except which has no reported 13C-NMR data.
C1516171820212223
2158.1158.4158.5168.9161.6174.3175.5174.6
3110.8111.9112.0108.8108.8107.8106.2106.6
4181.8183.6183.6182.5182.5184.3183.3183.1
5161.3163.1163.2161.2157.9163.0162.2162.7
699.8101.2101.299.8100.3101.0100.6100.7
7162.9164.6164.8163.1168.9164.8164.2164.2
894.696.296.294.995.095.995.395.3
9157.7159.4159.4157.9163.4159.5158.4158.4
10106.8108.5108.5105.5105.5107.0106.5107.4
11---20.520.528.333.340.4
12-----11.219.927.6
13------19.917.7
14-------11.7
1′99.7101.5101.5100.699.9101.6101.7101.7
2′73.174.774.773.373.574.774.874.8
3′76.277.977.976.677.677.878.578.5
4′69.771.972.069.670.771.271.271.1
5′74.175.876.066.276.878.479.379.2
6′63.464.264.7-61.162.462.462.3
1″119.5127.4127.3-----
2″108.8133.7131.2-----
3″145.6115.8117.0-----
4″138.6160.0161.4-----
5″145.6115.8117.0-----
6″108.8133.7131.2-----
7″165.9145.1146.9-----
8″-116.0115.1-----
9″-168.1168.9-----
SolventDMSO-d6CD3ODCD3ODDMSO-d6DMSO-d6CD3ODC5D5NC5D5N
References[29][30][30][31][157][40][41][41]
Table
Table 22. The 13C-NMR spectral data of compounds 24–32 except which has no reported 13C-NMR data.
Table 22. The 13C-NMR spectral data of compounds 24–32 except which has no reported 13C-NMR data.
C2425262829303132
2168.7157.3167.9168.2168.9169.2168.9168.5
3108.7108.3108.8108.8108.8109.3108.8108.4
4182.4181.9182.7182.8182.5184.2182.5182.1
5161.5161.1162.4162.4161.7163.1161.7161.3
699.9 *108.7100.6100.7100.2100.8100.099.6
7162.9162.6163.9163.9161.9163.4161.9161.6
894.9108.295.395.195.295.795.194.7
9157.7168.2158.3158.3157.9159.5157.9157.5
10105.5105.0106.3106.3105.7106.8105.6105.2
1120.319.919.920.120.520.420.520.1
1′99.8 *99.3101.9102.098.899.698.598.1
2′73.377.074.674.681.271.069.869.5
3′76.575.878.578.570.482.582.170.3
4′70.268.971.571.670.972.470.781.4
5′74.176.077.477.569.470.968.768.5
6′63.760.569.068.018.318.118.017.9
1″-108.7111.2102.7105.0105.9104.8104.4
2″-76.777.972.074.575.474.174.5
3″-79.280.372.877.277.876.877.1
4″-73.975.174.170.071.170.670.1
5″-64.165.869.876.777.774.876.7
6″---18.661.562.264.161.2
CH3CO20.9, 170.5-----21.1, 170.6-
SolventDMSO-d6CDCl3, DMSO-d6C5D5NC5D5NDMSO-d6DMSO-d6DMSO-d6DMSO-d6
References[33][16][44][46][31][22][31][47]
* Data interchangeable.
Table
Table 23. The 13C-NMR spectral data of compounds 33–41.
Table 23. The 13C-NMR spectral data of compounds 33–41.
C333435363738394041
2168.3168.2168.3168.3157.8154.8154.7168.6168.4
3108.2108.7108.3108.2110.6120.3125.8108.7108.4
4181.4182.7181.9181.9181.5183.8183.5182.5182.3
5161.1162.3161.1161.2157.7163.0163.1158.4185.1
699.5100.699.899.5108.9100.9100.8109.1108.5
7161.4163.7162.6162.6160.9164.6164.6161.1155.56
894.594.694.394.593.395.895.893.397.7 *
9157.3158.3157.4157.4155.4159.4159.5155.9160.3
10105.0106.3105.1105.1106.0107.4107.6105.1105.0
1119.919.919.819.87.410.219.320.519.9
12------13.47.96.9
1′98.0101.699.598.1100.1101.6101.6100.293.1 *
2′69.574.472.973.073.174.774.773.877.3
3′69.878.176.176.276.477.877.876.574.5
4′80.971.369.969.969.671.271.279.469.7
5′68.475.873.973.977.178.478.476.173.3
6′17.964.563.463.460.662.462.460.760.5
1″102.3121.0128.5127.9-----
2″81.4110.4114.8114.9-----
3″76.6147.4146.9148.9-----
4″69.8140.8147.7149.3-----
5″77.6147.4120.7122.5-----
6″61.0110.4115.9115.8-----
7″-167.1144.6144.7-----
8″--115.7115.8-----
9″--166.1166.2-----
1‴103.5-99.599.5-----
2‴71.2-70.371.2-----
3‴71.7-71.071.6-----
4‴66.4-67.167.1-----
5‴64.2-75.074.8-----
6‴--61.061.0-----
OCH3---55.8---60.1-
CH3CO--------20.7, 169.6
SolventDMSO-d6C5D5NDMSO-d6DMSO-d6DMSO-d6CD3ODCD3ODDMSO-d6DMSO-d6
References[47][48][33][33][49][50][50][23][51]
* Data interchangeable.
Table
Table 24. The 13C-NMR spectral data of compounds 43–52 except those which have no reported 13C-NMR data.
Table 24. The 13C-NMR spectral data of compounds 43–52 except those which have no reported 13C-NMR data.
C4345464748495052
2168.7168.4168.4169.5170.0160.0164.9164.9
3108.4108.0108.0108.4109.1112.5101.9118.6
4182.9182.7182.7182.4185.0185.0178.8177.6
5159.5152.6155.9152.5157.8158.8141.8137.9
698.3109.7114.3135.2116.3117.3116.6110.5
7160.9158.5158.8157.8160.2161.2160.4159.8
8104.6114.3109.894.7111.6112.9111.599.6
9155.0155.9152.6155.6154.6155.5159.3158.5
10105.2106.5106.5106.2108.2110.6117.1115.7
1120.520.020.120.220.510.322.819.4
128.18.89.0-8.910.519.948.7
13-8.99.1-9.5--205.3
14-------52.0
15-------62.7
16-------23.6
1′100.3104.3104.4100.8105.7106.5100.3102.1
2′73.976.074.174.175.376.577.673.0
3′76.573.976.378.075.678.573.676.3
4′79.470.069.969.971.772.570.169.4
5′76.173.477.077.077.776.476.977.0
6′60.763.061.061.264.365.361.060.5
1″-----173.1--
2″-----47.3--
3″-----71.4--
4″-----46.9--
5″-----176.6--
6″-----28.4--
OCH360.1--56.7----
CH3CO-20.4, 170.1--20.4, 172.5---
SolventDMSO-d6DMSO-d6*DMSO-d6*CD3ODCDCl3DMSO-d6
References[23][51][24][36][24][52][53][57]
* The authors did not report the NMR solvent.
Table
Table 25. The 13C-NMR spectral data of compounds 53–64 except those which have no reported 13C-NMR data.
Table 25. The 13C-NMR spectral data of compounds 53–64 except those which have no reported 13C-NMR data.
C535455565760616264
2161.0166.3169.9166.6166.5105.9104.783.5148.0
3117.2110.7109.3107.6106.946.252.942.2140.5
4178.1177.4184.0182.2182.5199.2198.9193.7178.9
5141.3117.896.0162.0162.0165.3165.2161.5163.6
6113.0125.0162.999.598.897.597.5100.0100.2
7159.9119.2101.0165.1164.8168.4168.4166.6166.2
899.7147.4164.794.593.697.097.099.195.3
9158.8147.3159.3158.1158.2160.4160.2166.2159.3
10116.1125.4119.0104.3104.2102.0102.4106.7106.6
1147.320.120.366.166.013.823.733.2-
12202.5-----11.818.2 *-
1329.8--------
1422.3--------
1’101.3102.4101.6102.8102.7104.1104.1104.0102.1
2’73.174.874.773.973.675.075.074.672.0
3’76.378.678.376.476.677.977.977.474.0
4’69.571.271.467.770.171.071.071.271.5
5’77.079.277.863.676.878.078.078.572.4
6’60.962.462.4-61.362.562.562.562.5
SolventDMSO-d6C5D5NCD3ODDMSO-d6CD3ODCD3ODCD3ODCD3ODCD3OD
References[57][58][59][31][60][54][50][63][65]
* Data interchangeable.
Table
Table 26. The 13C-NMR spectral data of compounds 66–72.
Table 26. The 13C-NMR spectral data of compounds 66–72.
C66676869707172
2167.3174.7168.3168.4167.8169.4174.4
3107.8105.1108.6108.8107.0109.2105.3
4181.8182.2181.8181.8182.0184.3182.2
5160.6160.6160.6160.6160.4162.3160.4
6108.7108.7108.6108.8108.1108.9107.0
7163.2163.3163.1163.1162.4165.0163.4
893.393.493.393.393.995.293.7
9156.6156.7156.6156.6157.0159.4156.9
10103.0103.3103.2103.2102.9105.1103.1
1119.832.343.166.220.020.432.4
12-19.864.146.0--19.8
13-19.823.363.8--19.8
14---43.8---
15---23.5---
1′73.073.072.972.970.875.670.7
2′70.170.270.070.072.072.672.0
3′78.978.978.878.876.780.176.6
4′70.670.670.570.570.871.970.7
5′81.481.681.481.482.080.281.8
6′61.461.561.461.461.665.261.5
1″----119.9121.6119.9
2″----108.9110.4108.7
3″----145.4146.6145.4
4″----138.2140.0138.1
5″----145.4146.6145.4
6″----108.9110.4108.9
7″----164.8168.6164.7
SolventDMSO-d6DMSO-d6DMSO-d6DMSO-d6DMSO-d6CD3ODDMSO-d6
References[69][69][72][72][71][73][69]
Table
Table 27. The 13C-NMR spectral data of compounds 73–79 except those which have no reported 13C-NMR data.
Table 27. The 13C-NMR spectral data of compounds 73–79 except those which have no reported 13C-NMR data.
C7374757679
2167.7174.9162.3163.1160.6
3106.3105.3113.2111.0112.4
4182.0182.2181.9181.8178.5
5161.1160.9143.1146.1*
6108.1106.4127.0128.3126.5
7163.1163.2160.1161.1160.8
893.493.4119.4121.1100.6
9157.1157.0161.3157.9159.0
10103.0103.1115.8114.3114.6
1119.932.448.748.547.8
12-19.78204.4204.6202.4
13-19.7529.830.729.8
14--23.323.322.5
CH3O---55.8-
1′70.770.775.575.671.4
2′69.769.771.972.381.7
3′77.677.680.079.978.2
4′68.768.772.972.170.1
5′81.881.779.878.581.1
6′61.261.265.265.460.9
1″119.7119.7133.6128.3105.1
2″108.9108.9131.2131.074.3
3″145.5145.4116.8115.376.1
4″138.5138.4161.3160.469.3
5″145.5145.4116.8115.376.1
6″108.9108.9131.2131.060.3
7″165.3165.4146.2146.2-
8″--114.9116.0-
9″--169.2169.1-
1‴119.1119.0---
2‴108.7108.7---
3‴145.3145.3---
4‴138.4138.3---
5‴145.3145.3---
6‴108.7108.7---
7‴164.6164.4---
SolventDMSO-d6DMSO-d6CD3ODCD3ODDMSO-d6
References[71][71][74][74][78]
* The authors missed assigning this position.
Table
Table 28. The 13C-NMR spectral data of compounds 80–89.
Table 28. The 13C-NMR spectral data of compounds 80–89.
C80818283848586878889
2167.0169.3174.4173.0168.2167.6167.2174.8167.7174.5
3107.4108.7105.0106.2108.3107.8107.5105.4108.0105.6
4181.9184.3182.2181.9181.9182.2181.9182.4182.2182.4
5160.4149.4160.4160.4160.3160.8160.5160.7161.0161.0
698.494.598.598.798.397.698.397.898.097.9
7162.5162.8162.8164.2162.7162.2162.6162.3162.4162.6
8104.3105.2104.1104.7108.4103.9104.0102.8103.9102.1
9156.1164.6156.5156.6158.9157.1156.3157.2157.1157.2
10103.5106.3102.0103.3103.8102.8103.5104.0102.0104.0
1119.620.332.739.142.111.019.733.120.133.1
12--20.027.066.5--19.8-20.3
13--19.511.445.8--20.3-20.1
14---17.464.1-----
15----23.6-----
1′73.174.973.173.373.270.673.370.770.770.8
2′71.072.871.271.270.372.570.072.570.170.2
3′78.580.078.578.778.676.178.176.077.077.0
4′70.371.770.870.971.070.870.771.268.568.9
5′81.182.481.581.581.481.778.382.081.581.9
6′61.362.961.861.761.561.563.861.861.061.3
1″-----119.7119.4119.6119.6119.6
2″, 6″-----108.8108.5108.7108.9108.9
3″, 5″-----145.5145.5145.4145.6145.5
4″-----138.8138.3138.3138.7138.7
7″-----165.0165.8165.0165.5165.4
1‴--------118.7118.7
2‴, 6‴--------108.7108.7
3‴, 5‴--------145.5145.4
4‴--------138.5138.6
7‴--------164.8164.8
OCH3-56.8--------
SolventDMSO-d6CD3ODDMSO-d6DMSO-d6DMSO-d6DMSO-d6DMSO-d6DMSO-d6DMSO-d6DMSO-d6
References[86][87][158][158][72][71][91][69][71][71]
Table
Table 29. The 13C-NMR spectral data of compounds 91–100 except which has no reported 13C-NMR data.
Table 29. The 13C-NMR spectral data of compounds 91–100 except which has no reported 13C-NMR data.
C9193949596979899100
2162.7164.9167.1167.0169.2160.2160.2160.8159.6
3109.8111.2112.2111.9110.8112.6112.4113.0113.7
4182.7178.7182.3181.9182.4178.3178.5178.9179.1
5144.0141.0143.1143.7144.1139.5140.1141.3144.1
6112.8111.5112.2112.6113.1116.9116.3111.9118.5
7162.5160.0162.3162.1162.7160.2159.5160.3159.0
8113.3112.8116.1113.1113.7107.1110.0113.1106.2
9158.8157.2160.0158.9159.1155.9157.8157.3159.6
10117.4115.9118.5117.0117.6114.3114.7115.9113.9
11124.743.244.344.276.247.247.747.848.2
12139.063.866.766.369.5202.5202.4202.5200.7
1318.423.823.623.619.722.222.630.030.2
1423.622.823.323.623.729.929.923.023.1
1556.956.4-56.756.9--56.6-
1′75.173.076.074.674.980.273.572.968.1
2′72.470.973.272.772.977.571.071.173.7
3′80.378.880.180.080.374.878.779.173.7
4′72.370.871.871.972.280.570.470.770.2
5′82.981.882.782.482.668.381.581.876.6
6′63.061.762.863.063.363.861.461.861.6
2′-OCOCH3--------168.6,
20.7
3′-OCOCH3--------169.4,
20.7
4′-OCOCH3--------170.3,
20.7
6′-OCOCH3--------170.6,
20.7
SolventCD3ODDMSO-d6CD3ODCD3ODCD3ODDMSO-d6DMSO-d6CD3ODCDCl3
References[80][159][160][82][160][94][94][96][93]
Table
Table 30. The 13C-NMR spectral data of compounds 103–110 except which has no reported 13C-NMR data.
Table 30. The 13C-NMR spectral data of compounds 103–110 except which has no reported 13C-NMR data.
C103104106107108109110
2165.0165.0167.4167.2167.4167.1167.2
3111.3111.3112.5112.6112.6111.9111.9
4178.6178.8182.3182.2182.2181.9182.0
5141.7141.8144.6144.8144.6144.3144.3
6111.0111.3112.7112.6112.5112.3112.4
7159.5159.8162.1162.0162.0161.6161.6
8110.6110.7111.8111.4111.8111.6111.3
9157.4157.5159.8159.6159.6159.3159.1
10115.8115.8117.2117.2117.2116.9116.9
1143.143.344.644.944.644.544.3
1264.463.965.966.366.066.666.5
1323.323.723.623.723.623.523.6
1422.822.923.723.723.623.523.3
1556.556.557.057.157.056.957.0
1′70.670.672.872.872.871.971.8
2′72.672.373.473.773.974.073.7
3′75.775.977.777.777.977.677.4
4′70.470.972.472.472.372.472.4
5′81.882.083.080.182.982.782.4
6′61.561.663.164.463.162.962.7
1″133.9125.0127.0127.0128.2135.3126.7
2″128.9130.3133.2131.1130.9128.9130.9
3″128.2115.8115.7116.9115.4129.7116.6
4″130.4159.6160.0161.3163.2131.3160.7
5″128.2115.8115.7116.9115.4129.7116.6
6″128.9130.3133.2131.1130.9128.9130.9
7″144.1144.4145.0146.6146.1146.1146.4
8″117.8114.0115.7114.6115.6118.1114.2
9″165.0165.4167.6168.0167.8167.2167.8
OCH3----55.9--
COCH3---173.0, 20.9---
SolventDMSO-d6DMSO-d6CD3ODCD3ODCD3ODCD3ODCD3OD
References[99][159][80][100][100][82][82]
Table
Table 31. The 13C-NMR spectral data of compounds 111–122 except which has no reported 13C-NMR data.
Table 31. The 13C-NMR spectral data of compounds 111–122 except which has no reported 13C-NMR data.
C111112113114115116117119120121122
2167.2167.6169.7160.3163.0160.1163.1160.6164.0167.6166.8
3112.1112.2110.51125113.8112.5111.0112.5112.4112.2112.2
4182.2182.3182.4178.6182.1178.4181.8178.6182.0182.3182.3
5143.5144.6144.8141.0144.7140.4146.1141.8144.9144.6144.8
6116.3112.6112.7115.8112.2115.7128.3111.5113.1112.6112.7
7161.3162.0162.1159.l162.1159.4161.1159.7162.3161.0162.2
8110.0111.9111.8110.2112.0110.7121.1110.8111.6111.9111.9
9160.4159.6159.4158.3159.6157.9157.9157.4159.5159.6159.6
10117.0117.3117.5114.8117.1114.8114.3115.6117.6117.2117.3
1144.344.675.748.149.147.848.547.998.644.644.6
1266.766.869.2202.4204.7202.3204.6202.1203.766.866.8
1323.523.619.730.429.929.630.729.623.723.724.0
1423.523.623.722.723.722.623.322.725.023.623.5
15-57.157.1-57.1-55.855.557.257.157.1
1′73.072.172.870.272.173.375.670.472.672.672.6
2′74.074.074.172.373.970.872.372.274.374.173.6
3′77.977.977.876.077.978.579.975.878.077.877.6
4′72.172.772.370.272.670.472.170.671.978.378.1
5′82.882.983.081.882.878.478.581.983.382.982.9
6′63.163.163.161.863.364.865.461.563.563.063.0
1″128.3127.5135.7125 I127.0125.0128.3125.5135.7129.8129.7
2″131.0115.1129.21301130.8130.3131.0111.1129.3130.8132.6
3″116.7149.9130.1115.8116.7115.7115.3147.9130.1118.0116.7
4″161.2146.6131.6159.6161.3159.7160.4149.2131.6163.8159.7
5″116.7116.6130.1115.8116.7115.7115.3115.5130.1--
6″131.0123.0129.21301130.8130.3131.0122.9129.3--
7″146.2147.1146.4144.4145.3144.9146.2144.6146.3146.0144.7
8″115.8114.5118.4114.1115.1114.0116.0114.2118.5116.5117.6
9″168.0168.2167.4165.4168.1166.7169.1165.4167.4167.8167.7
OCH356.1------56.3---
1‴---------101.9101.7
2‴---------74.874.9
3‴---------72.172.6
4‴---------71.371.2
5‴---------78.077.9
6‴---------62.562.4
SolventCD3ODCD3ODCD3ODDMSO-d6DMSO-d6DMSO-d6CD3ODDMSO-d6CD3ODCD3ODCD3OD
References[80][82][160][161][162][163][74][164][81][160][160]
Table
Table 32. The 13C-NMR spectral data of compounds 123–129 except which has no reported 13C-NMR data.
Table 32. The 13C-NMR spectral data of compounds 123–129 except which has no reported 13C-NMR data.
C123124126127128129
2167.7168.3171.3170.7167.7169.9
3108.0108.5105.6105.5108.3108.4
4182.2182.4184.3183.0182.7182.4
5158.8157.8160.2158.1159.5159.6
6110.4111.1112.5112.8107.4105.2
7162.3163.1163.8161.0162.9163.1
893.290.594.493.092.892.9
9156.1156.6157.8156.1156.7156.4
10103.3104.4106.8105.6103.4103.8
1119.919.961.660.018.860.0
OCH3-56.5----
1′20.520.522.120.526.426.4
2′126.9126.4128.7124.679.979.8
3′131.8132.3132.9134.1143.7143.7
4′66.166.168.461.0114.2114.2
5′21.221.321.920.015.215.2
1″101.5101.6102.7100.199.499.4
2″73.673.675.373.273.673.6
3″76.977.078.376.776.376.3
4″70.270.271.867.770.270.2
5″77.077.077.977.076.776.7
6″61.161.162.960.161.261.2
SolventDMSO-d6DMSO-d6CD3ODCD3ODCD3ODCD3OD
References[104][104][106][60][60][60]
Table
Table 33. The 13C-NMR spectral data of compounds 130–139.
Table 33. The 13C-NMR spectral data of compounds 130–139.
C130131132133134135136137138139
2170.7167.6170.7168.3171.4168.9165.0171.0171.5171.8
3105.5107.4104.9108.1105.5113.9*110.4110.7110.7
4183.0181.8181.9182.5182.5176.6*179.3180.4180.6
5158.8158.8158.9159.5159.5132.6*106.6119.2126.2
6111.497.697.898.398.4111.499.3150.7126.2126.6
7162.1159.9160.1160.6160.8158.2162.9153.1122.1135.6
893.3107.5107.4108.1108.2103.694.8106.9147.8119.3
9156.3153.8153.5154.4154.1163.4*149.8149.0158.0
10105.7104.3104.8105.0105.4112.7*116.2125.0124.3
1160.019.559.320.259.5127.9121.6102.2141.4136.2
1′28.220.320.321.020.9131.9128.574.3129.5114.0
2′74.6120.5120.4121.1121.0115.7115.778.1129.6150.7
3′147.9134.9134.9135.6135.7157.1161.571.5127.4146.4
4′109.565.965.866.566.5115.7115.778.0129.6118.1
5′16.613.113.113.813.7131.9128.562.8129.5122.0
6′-----39.339.1-33.833.6
7′-----86.337.5-37.037.1
8′-----127.9121.6102.2141.4136.2
1″101.2100.1100.1100.7100.7101.8100.3131.5103.0102.9
2″73.672.972.973.573.574.6*133.075.074.9
3″76.576.776.776.776.778.4*116.378.277.8
4″69.869.269.269.869.871.2*164.171.371.3
5″77.176.176.177.377.378.2*116.378.278.1
6″61.160.260.260.860.862.5*120.962.562.4
7″-------33.9--
8″-------37.1--
OCH3-------6-OCH3 56.3
4″-OCH3 55.1		-56.6
SolventCD3ODDMSO-d6DMSO-d6DMSO-d6DMSO-d6CD3ODDMSO-d6DMSO-d6CD3ODCD3OD
References[60][108][108][109][109][110][111][112][113][114]
* The authors missed assigning these positions.
Table
Table 34. The 13C-NMR spectral data of compounds 140–148.
Table 34. The 13C-NMR spectral data of compounds 140–148.
C140141142143144145146147148
2147.2146.9147.389.989.092.992.192.388.2
3106.1105.0104.924.328.328.127.928.030.1
4153.7160.5159.2165.5164.5160.3165.3156.3158.5
5177.2185.9184.7176.9176.4184.7176.6176.6182.9
6109.7107.8107.2111.9109.8109.5110.9111.4107.2
7163.7169.0168.7163.3164.0169.7162.7162.6166.7
995.892.092.094.895.290.494.094.288.8
10157.8156.1154.5159.9160.1168.3159.7165.4166.6
11117.0114.3113.4118.7117.2111.3118.1118.5108.7
12152.8106.9106.3112.3111.4106.6112.5112.8102.9
13155.6155.7155.2156.4157.7157.9156.1159.9158.6
1465.767.866.321.420.720.866.466.866.1
4-OCH361.9---*-60.861.0-
1′103.0104.4104.477.374.379.770.870.8143.7
2′74.075.074.223.424.124.326.026.2115.5
3′77.277.977.622.323.523.025.625.815.7
4′70.671.670.9------
5′77.178.076.7------
6′61.768.769.5------
1″-111.1103.398.9100.199.5104.0104.4102.8
2″-77.274.475.174.675.674.875.073.7
3″-80.677.478.878.678.578.478.376.7
4″-74.970.971.371.472.071.471.370.3
5″-65.577.777.178.276.878.175.776.9
6″--61.962.463.168.562.664.561.4
1‴-----111.2-126.5-
2‴-----78.6-111.4-
3‴-----81.0-149.0-
4‴-----75.6-151.2-
5‴-----66.2-116.8-
6‴-------123.9-
7‴-------145.9-
8‴-------115.1-
9‴-------167.8-
3‴-OCH3-------55.9-
SolventDMSO-d6, C6D6CD3ODDMSO-d6CDCl3, CD3ODCDCl3, CD3ODCD3ODC5D5NC5D5NCD3OD
References[117][118][109][122][122][119][121][132][60]
* The authors missed assigning this position.
Table
Table 35. The 13C-NMR spectral data of compounds 149–155.
Table 35. The 13C-NMR spectral data of compounds 149–155.
C149150151152153154155
2167.4169.5162.7167.6167.6170.9168.7
3108.7108.0111.1107.5107.4105.6108.6
4182.7184.2175.3181.9181.8182.5182.6
5160.0160.9160.7 *158.6158.5159.2160.3
6104.1105.0104.9103.1103.1103.8102.5
7159.6160.4152.7 *163.5163.3164.1164.3
894.995.891.1109.8109.9110.5105.8
9156.3157.7157.8152.9152.7153.1155.0
10104.4105.0107.7105.5105.4106.5106.1
2′78.479.376.669.669.670.274.2
3′74.375.072.4135.2135.0135.873.5
4′22.322.722.4124.7124.7125.2132.7
5′---20.620.320.9117.3
1″102.4102.0100.4101.2100.9101.9103.9
2″74.974.9**72.872.673.373.7
3″78.478.176.976.876.176.876.5
4″71.871.970.270.169.470.170.9
5″78.475.076.976.675.276.676.0
6″63.068.861.360.667.761.668.5
1‴-111.0--102.7-103.4
2‴-77.9--72.8-73.7
3‴-80.5--76.1-76.9
4‴-75.0--69.4-70.0
5‴-65.7--75.9-77.0
6‴----60.4-61.1
2a20.120.419.019.419.259.720.1
2’a22.322.421.2----
2’b25.726.125.2----
3’a---69.669.670.273.0
7-OCH3--56.0----
SolventCDCl3CD3ODDMSO-d6DMSO-d6DMSO-d6DMSO-d6DMSO-d6
References[121][119][123][108][108][108][109]
* Interchangeable data. ** The authors missed the assignment of this position.
Table
Table 36. The 13C-NMR spectral data of compounds 157–165.
Table 36. The 13C-NMR spectral data of compounds 157–165.
C157158159160161162163164165
Chromone
moiety
2′92.492.292.292.292.292.292.292.292.2
3′27.927.827.827.827.827.827.827.827.8
4′156.3156.2156.2156.2156.2156.2156.2156.2156.1
5′176.2176.2176.2176.2176.2176.2176.3176.3176.3
6′111.5110.9111.1110.9110.9110.8111.1111.2111.1
7′162.1162.5162.4162.4162.7162.5162.6162.6162.5
9′94.194.094.094.094.194.094.094.194.0
10′165.4165.2165.2165.2165.2165.2165.2165.2165.2
11′118.5118.4118.4118.4118.4118.4118.4118.4118.4
12′112.9112.8112.8112.5112.8112.8112.8112.8112.7
13′159.9159.8159.8159.7159.8159.7159.8159.9159.8
14′66.366.366.566.266.466.266.566.366.5
4-OCH360.960.960.960.860.960.960.960.960.8
1″70.670.670.670.670.670.670.670.770.6
2″26.026.126.126.126.126.126.126.226.1
3″25.625.725.725.625.725.725.625.625.7
Glu-1101.7104.1104.2104.1104.1104.0104.2103.9104.3
Glu-274.574.974.874.874.974.974.974.874.9
Glu-379.178.378.178.478.478.478.478.278.1
Glu-469.371.271.471.471.571.371.572.071.9
Glu-578.476.975.477.177.176.777.076.876.7
Glu-662.463.564.262.762.762.862.662.962.7
Triterpene
moiety
131.831.931.932.330.332.027.431.931.9
229.829.830.030.029.530.029.829.629.8
387.888.088.388.488.188.388.388.088.0
441.140.341.241.241.241.240.741.141.1
547.147.047.447.442.647.443.847.046.9
620.520.420.820.921.720.822.020.420.3
725.625.825.926.4113.226.3114.025.825.7
846.045.947.149.0149.147.3148.645.846.4
919.819.919.219.921.119.527.620.020.5
1026.526.626.626.528.226.429.126.627.0
1136.736.626.326.425.426.163.236.736.4
1277.276.831.434.033.933.348.377.276.9
1348.848.742.241.841.246.645.448.748.8
1447.247.445.246.549.845.148.147.847.8
1543.443.450.882.580.442.845.243.845.6
1670.772.8218.6103.0103.372.5114.571.174.6
1755.755.660.460.560.351.461.056.852.4
1813.513.518.820.322.520.520.713.512.9
1929.930.730.030.728.230.118.729.830.0
2026.925.429.127.627.534.223.726.024.6
2121.120.819.921.421.617.319.621.125.7
2241.538.640.333.633.686.237.841.9106.0
23104.2102.9173.474.274.4109.671.7101.9152.9
2483.1212.4-80.580.477.388.577.775.9
2579.135.0-76.476.583.576.481.378.2
2619.419.2-21.621.627.323.223.722.3
2729.819.7-24.124.124.520.224.923.1
2819.419.419.611.818.219.427.419.520.7
2925.625.625.625.525.625.625.825.625.6
3015.215.215.215.514.215.314.515.215.2
Xyl-1107.4107.5107.5107.4107.4107.4107.4107.5107.5
Xyl-275.575.575.575.575.575.575.575.575.5
Xyl-378.578.678.578.578.578.578.578.578.5
Xyl-471.171.071.171.171.271.171.171.271.1
Xyl-567.067.067.167.067.067.067.067.067.0
COCH3170.4
21.5		170.4
21.5		-171.0
21.1		171.0
21.1		--170.5
21.6		170.6
21.1
SolventC5D5NC5D5NC5D5NC5D5NC5D5NC5D5NC5D5NC5D5NC5D5N
References[130][130][130][130][130][130][130][136][136]
Table
Table 37. The 13C-NMR spectral data of compounds 166 and 167.
Table 37. The 13C-NMR spectral data of compounds 166 and 167.
C166167
198.198.1
3154.5154.5
4105.6105.6
528.728.6
630.029.9
775.175.0
8133.3133.3
943.943.8
10121.1121.1
11168.6168.5 a
1′99.899.7
2′74.874.7 b
3′77.977.8 c
4′71.671.2 d
5′78.578.4 e
6′62.762.4 f
2″167.5168.1 a
3″118.2118.6
4″181.6181.8
5″163.5163.1
6″100.2101.1
7″166.2164.9
8″94.795.7
9″159.2158.7
10″104.9106.6
-CH318.919.0
1‴-101.6
2‴-74.8 b
3‴-77.9 c
4‴-71.6 d
5‴-78.5 e
6‴-62.7 f
NMRCD3ODCD3OD
References[43][43]
a−f Values with the same superscript are interchangeable.
Table
Table 38. The 13C-NMR spectral data of compounds 168–180 except those which have no reported 13C-NMR data.
Table 38. The 13C-NMR spectral data of compounds 168–180 except those which have no reported 13C-NMR data.
C168169170171172178179180
2163.7159.3168.0159.6167.5170.2166.3166.3
3108.7108.8109.7109.9110.0110.8110.0110.0
4179.2179.5178.9178.8179.0179.0178.7178.8
4a125.8126.2125.9 *126.4125.9 *125.8 *125.8 *126.5
5149.6149.6149.9150.0149.8150.1149.7149.9
6125.4125.4125.8125.9125.9 *125.8 *125.9126.0
6a137.0137.2137.0137.0137.4137.2137.3136.3
7183.0183.3183.2183.5183.3183.1183.1181.5
7a125.8127.3126.3 *126.5126.4 *126.1 *126.2 *130.7
8140.0140.6139.7140.0140.1139.9140.2119.3
9133.0132.6132.9132.2133.1133.3133.1133.2
10138.4138.5137.8137.0138.5138.6138.6140.7
11159.7163.9159.7167.6159.9159.9159.8159.5
11a116.0115.8116.1116.0116.2116.0116.1116.1
12188.1188.0187.9187.7188.1188.3188.0187.7
12a118.9118.9119.1119.1119.2118.9119.2119.8
12b155.7155.8156.0156.0156.2155.8156.1156.2
1324.024.124.324.224.124.224.124.1
14127.2125.957.660.359.175.657.757.7
1512.115.013.814.914.523.514.514.4
16134.2134.262.061.761.671.7 *63.963.9
1714.912.114.1123.3123.3127.455.455.4
18---134.1134.0130.251.851.8
19---14.413.813.517.217.2
2′77.377.777.277.677.377.277.367.9
3′71.971.871.370.671.971.7 *71.971.0
4′67.467.567.868.167.467.3 *67.457.7
5′28.341.028.838.828.428.428.335.0
6′75.275.474.874.075.275.075.268.2
7′18.918.918.818.518.918.918.917.5
8′-------13.2
4′-N(CH3)240.440.540.340.440.440.340.437.1
2″67.269.867.569.867.267.4 *67.3-
3″70.876.470.374.570.970.770.9-
4″57.457.657.659.157.357.957.3-
5″33.628.633.330.433.633.333.7-
6″69.564.969.465.769.769.669.6-
7″17.615.017.415.117.717.617.6-
8″12.313.713.113.912.312.612.3-
3″-COCH3-170.6
21.3		-171.0
21.5		----
4″-N(CH3)236.839.336.938.836.836.836.8-
SolventCDCl3CDCl3CDCl3CDCl3CDCl3CDCl3CDCl3CDCl3
References[165][140][141][140][142][143][165][146]
* Interchangeable values.
Table
Table 39. The 13C-NMR spectral data of compounds 181–183.
Table 39. The 13C-NMR spectral data of compounds 181–183.
C181182183
2168.4176.4176.5
3112.0111.1111.3
4180.3181.3178.4
4a126.1126.0124.7
5150.4150.4149.6
6121.3121.0121.2
6a138.3138.1139.0
7182.7182.7182.4
7a133.2133.2133.2
8120.1120.0119.8
9135.4135.5135.6
10137.4137.4137.0
11161.1161.0161.3
11a118.1118.0118.0
12189.1189.2189.2
12a122.0121.9121.6
12b157.7157.4156.9
1370.870.8175.3
1461.277.777.7
1563.772.672.6
1620.223.923.9
1713.717.017.1
1′98.998.9-
2′37.237.2-
3′58.358.4-
4′71.271.1-
5′70.470.4-
6′17.217.2-
7′24.624.5-
1″70.270.170.3
2″28.027.727.4
3″65.265.164.9
4″75.175.075.2
5″72.672.672.3
6″18.118.218.3
3″-N(CH3)243.2
41.7		43.3
41.4		42.5
42.5
1‴101.4101.4101.4
2‴33.433.433.4
3‴66.666.666.6
4‴72.072.072.0
5‴69.569.569.5
6‴17.517.517.5
SolventCD3ODCD3ODCD3OD
References[147][147][147]
Table
Table 40. The 13C-NMR spectral data of compounds 184–192.
Table 40. The 13C-NMR spectral data of compounds 184–192.
C184185186187188189190191192
2167.5167.4167.0167.0165.7165.7167.5169.3169.3
3111.1110.9110.9110.8111.3111.3111.1109.1109.1
4180.2180.0179.4179.4178.5178.6180.2182.4182.5
4a126.6126.4126.5126.4126.3126.3126.6113.3113.3
5149.2149.1149.4149.2148.2148.2149.3166.7166.7
6122.5122.4122.9122.8124.1124.0122.5110.7110.7
6a137.2137.1137.0136.9136.9136.9137.2139.8139.9
7181.2181.0181.2181.2181.5181.4181.2180.8180.8
7a130.3130.2130.4130.3130.5130.5130.5130.6130.4
8119.8119.7119.7119.7119.5119.5119.8119.4119.5
9133.6133.7133.4133.6133.3133.5133.7132.4132.8
10141.3141.1141.0140.9141.0140.9140.7140.2140.9
11159.1159.2159.3158.9159.3159.3159.4159.1159.1
11a115.8115.6115.9115.7115.9115.9115.9115.6115.4
12186.9186.9187.1186.9187.5187.4186.9186.2186.3
12a121.8121.6121.6121.6120.8120.8121.8112.3112.4
12b156.8156.7156.6156.5156.1156.1156.8156.6156.6
1380.980.079.078.948.348.280.9--
1459.859.759.859.759.859.759.860.060.0
1519.719.619.819.720.019.919.619.619.7
1662.762.562.562.562.562.562.762.762.7
1713.413.313.413.313.513.413.313.213.2
18170.5170.4170.9170.9170.4170.4170.5--
1952.652.552.452.352.352.352.6--
2′73.873.874.974.974.374.273.8--
3′68.968.968.568.268.868.869.0--
4′80.280.174.874.981.581.480.2--
5′67.967.926.126.068.067.968.0--
6′73.773.670.370.273.974.073.7--
7′14.114.014.714.714.714.614.0--
4′-OCH357.957.855.655.557.157.158.0--
2″70.370.770.270.870.370.870.070.070.7
3″77.782.677.882.777.882.876.077.382.8
4″54.958.155.158.154.958.151.756.158.1
5″40.344.740.444.740.444.844.938.544.8
6″62.162.262.362.262.262.362.363.662.3
7″14.713.514.813.514.713.614.115.413.6
8″24.114.023.813.924.214.132.622.614.0
4″-N(CH3)n27.940.327.840.328.140.4-27.240.3
1‴93.494.493.794.593.494.593.394.594.5
2‴30.831.130.931.130.931.130.831.131.1
3‴74.874.974.874.974.975.074.875.075.0
4‴72.172.172.172.072.272.272.271.572.2
5‴65.465.065.765.065.465.165.466.665.0
6‴17.717.617.717.617.817.717.817.517.7
3‴-OCH355.956.156.156.155.956.256.056.456.1
SolventCDCl3CDCl3CDCl3CDCl3CDCl3CDCl3CDCl3CDCl3CDCl3
References[149][149][149][149][137][137][137][137][137]
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Amen, Y.; Elsbaey, M.; Othman, A.; Sallam, M.; Shimizu, K. Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features. Molecules 2021, 26, 7646. https://doi.org/10.3390/molecules26247646

AMA Style

Amen Y, Elsbaey M, Othman A, Sallam M, Shimizu K. Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features. Molecules. 2021; 26(24):7646. https://doi.org/10.3390/molecules26247646

Chicago/Turabian Style

Amen, Yhiya, Marwa Elsbaey, Ahmed Othman, Mahmoud Sallam, and Kuniyoshi Shimizu. 2021. "Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features" Molecules 26, no. 24: 7646. https://doi.org/10.3390/molecules26247646

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