Microbial Metabolites of 8-Prenylnaringenin, an Estrogenic Prenylflavanone

Microbial metabolism studies of the phyto-estrogen (+/-)-8-prenylnaringenin (8-PN) (1) has led to the isolation of three pairs of metabolites (2-4). The structures of these compounds were identified as 5,4'-dihydroxy-7,8-[2-(1-hydroxy-1-methylethyl)-2,3-dihydrofurano]flavanones (2), 8-prenylnaringenin 7-O-beta-D-glucopyranosides (3), and 8-prenylnaringenin 7-O-beta-D-(6'-O-alpha-hydroxypropionyl)-glucopyranosides (4) on the basis of the spectroscopic analysis.