Microbial Metabolism of the Prenylated Chalcone Xanthohumol

Microbial metabolism of xanthohumol (1), a prenylated chalcone isolated from hops, gave three novel glucosylated derivatives (2−4) and a known compound, isoxanthohumol (5). The structures of the new compounds were identified as xanthohumol 4'-O-β-glucopyranoside (2), xanthohumol 4,4'-O-β-diglucopyranoside (3), and 5-methoxy-8-prenylnaringenin 7-O-β-glucopyranoside (4) on the basis of spectroscopic methods.