Identification and biological activity of microbial metabolites of xanthohumol

Abstract

Microbial transformation of xanthohumol using the culture broth of Cunninghamella echinulata NRRL 3655 afforded (2S)-8-[4″-hydroxy-3″- methyl-(2″-Z)-butenyl]-4′,7-dihydroxy-5-methoxyflavanone (5) and (2S)-8-[5″-hydroxy-3″-methyl-(2″-E)-butenyl]-4′, 7-dihydroxy-5-methoxyflavanone (6). Xanthohumol (1) and flavanone 6 as well as (E)-2″-(2‴-hydroxyisopropyl)-dihydrofurano[2″,3″: 4′,3′]-2′,4-dihydroxy-6′-methoxychalcone (2), (2S)-2″-(2‴-hydroxyisopropyl)-dihydrofurano[2″,3″:7,8] -4′-hydroxy-5-methoxyflavanone (3) obtained with Pichia membranifaciens showed antimalarial activity against Plasmodium falciparum. © 2003 Pharmaceutical Society of Japan.