Metabolism of dietary flavonoids in liver microsomes.

Flavonoids undergo substantial hepatic metabolism and the metabolites might significantly contribute to the effects of these dietary constituents. The metabolites of flavonoids in liver can be summarized as follows: 1) For flavones, the hydroxylation appears to occur at the C-4'-, C-3', C-6 and C-8- position when there is a single or no hydroxy group on the B-ring. The methoxyl groups positioned at the C-7, C-6 or C-4'- position of flavones are demethylated. The glucuronidation occurs at the 6, 7, 4' or 3'- hydroxyl moiety. Flavone glycosides and aglycones appear to undergo similar metabolic pathways. 2) For flavonols, the hydroxylation appears at the 3' and 4'- position and flavonols with a 4'-methoxy group are easily O-demethylated to their corresponding hydroxylated analogs. The glucuronidation takes place at the 7, 3, 3' and 4'- hydroxyl moiety. 3) For isoflavones, the microsomal hydroxylation is observed at the C-3'-, C-6 and C-8- position when there is a single or no hydroxy group on the B-ring. The demethylation takes place at the C-6- or C-4'- position when there is one methoxy group on C-4' or C-6-position, respectively. The glucuronidation occurs at the 4, or 5- hydroxyl moiety. 4) For chalcones, the C-3'-, and C-8- positions undergo hydroxylation. The C-8- position is a very active site for metabolism of chalcones.