Microbial metabolism. Part 6. Metabolites of 3- and 7-hydroxyflavones

Chem Pharm Bull (Tokyo). 2006 Mar;54(3):320-4. doi: 10.1248/cpb.54.320.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aspergillus / metabolism
  • Bacteria / metabolism*
  • Fermentation
  • Flavonoids / metabolism*
  • Magnetic Resonance Spectroscopy
  • Nocardia / metabolism
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared

Substances

  • Flavonoids
  • 7-hydroxyflavone
  • 3-hydroxyflavone