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.
flavonoid, microbial metabolism, Mucor ramannianus, Cunninghamella blakesleeana, Chaetomium cochlioides, Mortierella zonata
NCBI PubMed ID: 22976322Publication DOI: 10.1248/cpb.c12-00296Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: rimikell@olemiss.edu
Institutions: National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Mississippi, USA, Department of Pharmacognosy, School of Pharmacy, University of Mississippi, Mississippi, USA, School of Pharmacy, King Saud University, Riyadh, Saudi Arabia
Methods: 13C NMR, 1H NMR, IR, TLC, UV, extraction, optical rotation measurement, CC, cell growth, HR-ESI-MS, antibacterial assay
Found