Intestinal bacterial metabolism of flavonoids and its relation to some biological activities.
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.
Kim
D H
DH
College of Pharmacy, Kyung-Hee University, Seoul, Korea.
Jung
E A
EA
Sohng
I S
IS
Han
J A
JA
Kim
T H
TH
Han
M J
MJ
D001419:Bacteria / Q000378:metabolism*; D001711:Biotransformation; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000378:metabolism* / Q000494:pharmacology* / Q000633:toxicity; D006027:Glycosides / Q000378:metabolism; D006801:Humans; D007422:Intestines / Q000382:microbiology*; D010636:Phenols / Q000378:metabolism / Q000494:pharmacology; D010975:Platelet Aggregation Inhibitors / Q000494:pharmacology; D014361:Trypsin Inhibitors / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D005419:Flavonoids; D006027:Glycosides; D010636:Phenols; D010975:Platelet Aggregation Inhibitors; D014361:Trypsin Inhibitors