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.
Herath
Wimal
W
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, MS 38677, USA. ikhan@olemiss.edu
Ferreira
Daneel
D
Khan
Shabana Iqrar
SI
Khan
Ikhlas Ahmad
IA
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