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

Chemical & Pharmaceutical Bulletin
Wimal HerathIkhlas Ahmad Khan

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.

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Citations

Jun 2, 2012·TheScientificWorldJournal·Edyta Kostrzewa-Susłow, Tomasz Janeczko
May 10, 2007·Natural Product Research·Wimal HerathIkhlas A Khan
Sep 2, 2008·Chemical & Pharmaceutical Bulletin·Amany IbrahimIkhlas Khan
Jul 24, 2008·Journal of Natural Medicines·Ryota TsuchihashiJunei Kinjo
Jan 28, 2012·Indian Journal of Microbiology·Gurram Shyam PrasadS M Reddy
Mar 13, 2010·Phytochemistry·Amany K IbrahimIkhlas A Khan
Jul 23, 2009·International Journal of Systematic and Evolutionary Microbiology·Andrew S LammJohn P N Rosazza
May 2, 2014·Biotechnology Advances·Jianbo XiaoMilen I Georgiev
Dec 19, 2014·Natural Product Research·Guo-Bo XuGuo-You Li
Sep 29, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Monika DymarskaEdyta Kostrzewa-Susłow
Jan 19, 2012·Chemistry & Biodiversity·Yuqiong DongXiaobo Li
May 12, 2009·Menopause : the Journal of the North American Menopause Society·Evelyne ReiterAlois Jungbauer
Aug 4, 2015·Chemical & Pharmaceutical Bulletin·Julie Rakel MikellIkhlas Ahmad Khan
Aug 4, 2019·Pharmaceutics·Robert AncuceanuVlad Negulescu
Aug 29, 2020·International Journal of Molecular Sciences·Mateusz ŁużnyTomasz Janeczko

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