Table 10.
8-C-Chromone glycosides with their sources and biological activities.
| No. | Compound | Source | Biological Activity |
|---|---|---|---|
| 80 | Isobiflorin |
Abrus 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] |
| 81 | 7-methoxy-isobiflorin | Zhuyeqing Liquor; a famous traditional Chinese functional health liquor [87] |
No reported biological activity |
| 82 | 5,7-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] |
| 83 | 5,7-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 |
| 84 | Obtusichromoneside B | Cassia obtusifolia seeds [72] | Inhibitory activity against human organic anion/cation transporters (OATs/OCTs) and organic anion transporting polypeptides (OATPs) at 50 μM [72] |
| 85 | Kunzeachromone 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] |
| 86 | 8-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] |
| 87 | 8-β-C-(2′-galloylglucopyranosyl)-5,7-dihydroxy-2-isopropylchromone | Baeckea frutescens leaves [70] | Active against copper-induced LDL oxidation with an IC50 value of 3.91 ± 0.18 µM [70] |
| 88 | Kunzeachromone F [2-Methyl-5,7-dihydroxy-chromone-8-β-d-(2’,3′-di-O-galloyl)-glucopyranoside] |
Kunzea ambigua leaves [71] | No reported biological activity |
| 89 | Kunzeachromone B [2-Isopropyl-5,7-dihydroxy-chromone-8-β-d-(2’,3′-di-O-galloyl)-glucopyranoside] |
Kunzea ambigua leaves [71] | No reported biological activity |
| 90 | 2,5-dimethyl-8-C-β-d-glucopyranosyl-7-hydroxy-chromone | Aloe vera [92] | No reported biological activity |
| 91 | 2-(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] |
| 92 | 8-C-β-d-glucosyl-(R)-aloesol | Aloe vera [76,80] | BACE1 (β-secretase) inhibitory activity (39.2%) at 100 μM [80] |
| 93 | 8-C-β-d-glucosyl-7-O-methyl-(R)-aloesol |
Aloe vera [76,80] and anerobic incubation of aloesin with bacterial mixture [93] |
BACE1 (β-secretase) inhibitory activity (26.8%) at 100 μM [80] |
| 94 | 8-C-β-d-glucosyl-(S)-aloesol |
Aloe vera [76] and anerobic incubation of aloesin with bacterial mixture [93] |
No reported biological activity |
| 95 | 8-C-β-d-glucosyl-7-O-methyl-(S)-aloesol |
Aloe vera [76] and anerobic incubation of aloesin with bacterial mixture [93] |
No reported biological activity |
| 96 | 8-C-β-d-glucosyl-7-O-methylaloediol | Aloe vera [76,80] | No reported biological activity |
| 97 | Neoaloesin A |
Aloe vera [76] Aloe barbadensis leaves [94] |
No reported biological activity |
| 98 | Aloesin |
Aloe 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] |
| 99 | 7-O-methylaloesin | Aloe rupestris leaves exudate [96] | No reported biological activity |
| 100 | Aloesin-2″,3″,4″,6″-tetra-O-acetate | Anerobic incubation of aloesin with bacterial mixture [93] |
No reported biological activity |
| 101 | 2″-O-tigloylaloesin | Aloe cremnophila leaves exudate [97] | No reported biological activity |
| 102 | 8-C-β-d-glucopyranosyl-7-hydroxy-5-methylchromone-2-carboxylic acid | Herbal tea “muti” [98] | No reported biological activity |
| 103 | 8-[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] |
| 104 | Aloeresin D | Aloe vera [76] | No reported biological activity |
| 105 | Rabaichromone | Aloe vera [76] | No reported biological activity |
| 106 | Allo-aloeresin D | Aloe vera [76] | No reported biological activity |
| 107 | Aloeresin K |
Aloe vera [76] Aloe barbadensis leaf skin [100] |
No reported biological activity |
| 108 | Aloeresin J |
Aloe vera [76] Aloe barbadensis leaf skin [100] |
No reported biological activity |
| 109 | Aloeresin E | Aloe vera leaves [76,82] | Inhibition of tyrosinase enzyme (40% and 80% at 50 and 100 ppm, respectively) [82] |
| 110 | Isoaloeresin D | Aloe 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] |
| 111 | 2′-O-[p-methoxy-(E)-cinnamoyl]-(S)-aloesinol | Aloe nobilis leaves [12] | BACE1 inhibitory activity (34.1%) at 100 μM [80] |
| 112 | Iso-rabaichromone | Aloe vera [76,82] | No reported biological activity |
| 113 | 8-C-glucosyl-(2′-O-cinnamoyl)-7-O-methylaloediol B | Aloe vera leaves [76] | No reported biological activity |
| 114 | Aloeresin A | Aloe 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] |
| 115 | 7-O-methyl-aloeresin A | Aloe vera [76] | Tyrosinase inhibitory activity with an IC50 value of 9.8 μM [81] |
| 116 | 6′-O-coumaroyl-aloesin | Aloe vera [76] | Anti-lipid peroxidation activity with an IC50 value of 476.4 ± 0.9 µM [75] |
| 117 | 7-Methoxy-6′-O-coumaroyl-aloesin | Aloe vera [76] | Weak anticancer activity against breast cancer cell line, MDA-MB-231 (induce 30% decline in cell survival at 25 μM ) [102] |
| 118 | 2′-Feruloylaloesin | Aloe 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] |
| 119 | 2′-Feruloyl-7-O-methylaloesin | Aloe nobilis leaves [80] | Inhibition activity against BACE1 (β-secretase) (48.7%) at 100 μM [80] |
| 120 | 9-Dihydroxyl-2′-O-(Z)-cinnamoyl-7-methoxy-aloesin | Aloe 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] |
| 121 | 4′-O-β-d-glucosyl-isoaloeresin DI | Aloe vera [76] | No reported biological activity |
| 122 | 4′-O-β-d-glucosyl-isoaloeresin DII | Aloe vera [76] | No reported biological activity |