Identification and biological activity of microbial metabolites of xanthohumol.
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.
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, MS 38677, USA. ikhan@olemiss.edu
Wimal
W
Herath
Daneel
D
Ferreira
Shabana Iqrar
SI
Khan
Ikhlas Ahmad
IA
Khan
D000818:Animals; D000890:Anti-Infective Agents / Q000378:metabolism / Q000494:pharmacology*; D000962:Antimalarials / Q000378:metabolism / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000378:metabolism / Q000494:pharmacology*; D001419:Bacteria / Q000378:metabolism; D020093:Cunninghamella / Q000378:metabolism; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids; D005658:Fungi / Q000187:drug effects; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects; D011427:Propiophenones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000890:Anti-Infective Agents; D000962:Antimalarials; D000972:Antineoplastic Agents, Phytogenic; D005419:Flavonoids; D011427:Propiophenones; C104536:xanthohumol