Kim D H, Jung E A, Sohng I S, Han J A, Kim T H, Han M J
College of Pharmacy, Kyung-Hee University, Seoul, Korea.
Arch Pharm Res. 1998 Feb;21(1):17-23. doi: 10.1007/BF03216747.
Flavonoid glycosides were metabolized to phenolic acids via aglycones by human intestinal microflora producing alpha-rhamnosidase, exo-beta-glucosidase, endo-beta-glucosidase and/or beta-glucuronidase. Rutin, hesperidin, naringin and poncirin were transformed to their aglycones by the bacteria producing alpha-rhamnosidase and beta-glucosidase or endo-beta-glucosidase, and baicalin, puerarin and daidzin were transformed to their aglycones by the bacteria producing beta-glucuronidase, C-glycosidase and beta-glycosidase, respectively. Anti-platelet activity and cytotoxicity of the metabolites of flavonoid glycosides by human intestinal bacteria were more effective than those of the parental compounds. 3,4-Dihydroxyphenylacetic acid and 4-hydroxyl-phenylacetic acid were more effective than rutin and quercetin on anti-platelet aggregation activity. 2,4,6-Trihydroxybenzaldehyde, quercetin and ponciretin were more effective than rutin and ponciretin on the cytotoxicity for tumor cell lines. We insist that these flavonoid glycosides should be natural prodrugs.
类黄酮糖苷通过产生α-鼠李糖苷酶、外切β-葡萄糖苷酶、内切β-葡萄糖苷酶和/或β-葡萄糖醛酸苷酶的人类肠道微生物群，经由苷元代谢为酚酸。芦丁、橙皮苷、柚皮苷和枳橙苷通过产生α-鼠李糖苷酶和β-葡萄糖苷酶或内切β-葡萄糖苷酶的细菌转化为它们的苷元，而黄芩苷、葛根素和大豆苷分别通过产生β-葡萄糖醛酸苷酶、C-糖苷酶和β-糖苷酶的细菌转化为它们的苷元。人类肠道细菌对类黄酮糖苷代谢产物的抗血小板活性和细胞毒性比母体化合物更有效。3,4-二羟基苯乙酸和4-羟基苯乙酸在抗血小板聚集活性方面比芦丁和槲皮素更有效。2,4,6-三羟基苯甲醛、槲皮素和枳属苷元在对肿瘤细胞系的细胞毒性方面比芦丁和枳橙苷更有效。我们坚持认为这些类黄酮糖苷应该是天然前体药物。
