title: Bioconversion of 7-hydroxyflavanone: isolation, characterization and bioactivity evaluation of twenty-one phase I and phase II microbial metabolites.
abstract: Microbial metabolism of 7-hydroxyflavanone (1) with fungal culture Cunninghamella blakesleeana (ATCC 8688a), yielded flavanone 7-sulfate (2), 7,4'-dihydroxyflavanone (3), 6,7-dihydroxyflavanone (4), 6-hydroxyflavanone 7-sulfate (5), and 7-hydroxyflavanone 6-sulfate (6). Mortierella zonata (ATCC 13309) also transformed 1 to metabolites 2 and 3 as well as 4'-hydroxyflavanone 7-sulfate (7), flavan-4-cis-ol 7-sulfate (8), 2',4'-dihydroxychalcone (9), 7,8-dihydroxyflavanone (10), 8-hydroxyflavanone 7-sulfate (11), and 8-methoxy-7-hydroxyflavanone (12). Beauveria bassiana (ATCC 7159) metabolized 1 to 2, 3, and 8, flavanone 7-O-β-D-O-4-methoxyglucopyranoside (13), and 8-hydroxyflavanone 7-O-β-D-O-4-methoxyglucopyranoside (14). Chaetomium cochlioides (ATCC 10195) also transformed 1 to 2, 3, 9, together with 7-hydroxy-4-cis-ol (15). Mucor ramannianus (ATCC 9628) metabolized 1 in addition to 7, to also 4,2',4'-trihydroxychalcone (16), 7,3',4'-trihydroxyflavanone (17), 4'-hydroxyflavanone 7-O-α-L-rhamnopyranoside (18), and 7,3',4'-trihydroxy-6-methoxyflavanone (19). The organism Aspergillus alliaceus (ATCC 10060) transformed 1 to metabolites 3, 16, 7,8,4'-trihydroxyflavanone (20), and 7-hydroxyflavanone 4'-sulfate (21). A metabolite of 1, flavanone 7-O-β-D-O-glucopyranoside (22) was produced by Rhizopus oryzae (ATCC 11145). Structures of the metabolic products were elucidated by means of spectroscopic data. None of the metabolites tested showed antibacterial, antifungal and antimalarial activities against selected organisms. Metabolites 4 and 16 showed weak antileishmanial activity.
authors.affiliation: National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA. rimikell@olemiss.edu
authors.forename: Julie Rakel
authors.initials: JR
authors.lastname: Mikell
authors.forename: Ikhlas Ahmad
authors.initials: IA
authors.lastname: Khan
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D002597:Chaetomium / Q000737:chemistry / Q000378:metabolism; D020093:Cunninghamella / Q000737:chemistry / Q000378:metabolism; D044950:Flavanones / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry* / Q000187:drug effects / Q000378:metabolism*; D020094:Mortierella / Q000737:chemistry / Q000378:metabolism; D009089:Mucor / Q000737:chemistry / Q000378:metabolism; D009181:Mycoses / Q000188:drug therapy
chemical_list: D000890:Anti-Infective Agents; D044950:Flavanones; C059353:7-hydroxyflavanone