Microbial metabolism. Part 6. Metabolites of 3- and 7-hydroxyflavones.
Fermentation of 3-hydroxyflavone (1) with Beauveria bassiana (ATCC 13144) yielded 3,4'-dihdroxyflavone (3), flavone 3-O-beta-D-4-O-methylglucopyranoside (4) and two minor metabolites. 7-Hydroxyflavone (2) was transformed by Nocardia species (NRRL 5646) to 7-methoxyflavone (5) whilst Aspergillus alliaceus (ATCC 10060) converted it to 4',7-dihydroxyflavone (6). Flavone 7-O-beta-D-4-O-metylglucopyranoside (7) and 4'-hydroxyflavone 7-O-beta-D-4-O-methylglucopyranoside (8) were the metabolic products of 7-hydroxyflavone (2) when fermented with Beauveria bassiana (ATCC 7159). One of the minor metabolites of 3-hydroxyflavone (1) was tentatively assigned a beta'-chalcanol structure (9). Compounds 4, 7 and 8 are reported as new compounds. Structure elucidation of the metabolites was based on spectroscopic data.
Herath
Wimal
W
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University 38677, USA.
Mikell
Julie Rakel
JR
Hale
Amber Lynn
AL
Ferreira
Daneel
D
Khan
Ikhlas Ahmad
IA
D001230:Aspergillus / Q000378:metabolism; D001419:Bacteria / Q000378:metabolism*; D005285:Fermentation; D005419:Flavonoids / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009615:Nocardia / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D005419:Flavonoids; C429845:7-hydroxyflavone; C041477:3-hydroxyflavone