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5,7-Dihydroxyflavone (chrysin) (1) when fermented with fungal cultures, Aspergillus alliaceous (ATCC 10060), Beauveria bassiana (ATCC 13144) and Absidia glauco (ATCC 22752) gave mainly 4'-hydroxychrysin (4), chrysin 7-O-β-D-4-O-methylglucopyranoside (5) and chrysin 7-sulfate (6), respectively. Mucore ramannianus (ATCC 9628), however, transformed chrysin into six metabolites: 4'-hydroxy-3'-methoxychrysin (chrysoeriol) (7), 4'-hydroxychrysin (apigenin) (4) 3',4'-dihydroxychrysin (luteolin) (8), 3'-methoxychrysin 4'-O-α-D-6-deoxyallopyranoside (9), chrysin 4'-O-α-D-6-deoxyallopyranoside (10), and luteolin 3'-sulfate (11). Cultures of A. alliaceous (ATCC 10060) and B. bassiana (ATCC 13144) metabolized 5-hydroxyflavone (2) into 5,4'-dihydroxyflavone (12) and 4'-hydroxyflavone 5-O-β-D-4-O-methylglucopyranoside (13), respectively. 6-Hydroxyflavone (3) was transformed into 6-hydroxyflavanone (14), flavone 3-O-β-D-4-O-methylglucopyranoside (15) and (+/-)-flavanone 6-O-β-D-4-O-methylglucopyranoside (16) by cultures of Beauveria bassiana (ATCC 13144). The structures of the metabolic products were elucidated by means of spectroscopic data. The significance of the metabolites as antioxidants in relation to their structure is briefly discussed.

flavonoid, microbial metabolism, Beauveria bassiana, Aspergillus alliaceus, Absidia glauco, Mucore ramannianus

NCBI PubMed ID: 18379084
Publication DOI: 10.1248/cpb.56.418
Journal NLM ID: 0377775
Publisher: Pharmaceutical Society Of Japan
Correspondence: ikhan@olemiss.edu
Institutions: National Center for Natural Products Research, The University of Mississippi, Mississippi, USA, Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, Mississippi, USA
Methods: 13C NMR, 1H NMR, TLC, biological assays, FTIR, UV, extraction, optical rotation measurement, CC, HR-ESI-MS

6-Hydroxyflavanone (1) when fermented with fungal culture Cunninghamella blakesleeana (ATCC 8688a) yielded flavanone 6-O-β-D-glucopyranoside (2), flavanone 6-sulfate (3), and 6-hydroxyflavanone 7-sulfate (4). Aspergillus alliaceus (ATCC 10060) also transformed 1 to metabolite 3 as well as 4'-hydroxyflavanone 6-sulfate (5) and 6,4'-dihydroxyflavanone (6). Beauveria bassiana (ATCC 7159) metabolized 1 to 6 and flavanone 6-O-β-D-4-O-methyglucopyranoside (7). Mucor ramannianus (ATCC 9628) transformed 1 to 2,4-cis-6-hydroxyflavan-4-ol (8), 2,4-trans-6-hydroxyflavan-4-ol (9), 2,4-trans-6,4'-dihydroxyflavan-4-ol 5-sulfate (10), 1,3-cis-1-methoxy-1-(2,5-dihydroxyphenyl)-3-phenylpropane (11) and 2,4-trans-flavan-4-ol 6-sulfate (12). 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. However, weak antileishmanial activity was observed for metabolite 11 when tested against Leishmania donovani

flavonoid, microbial metabolism, Beauveria bassiana, Mucor ramannianus, Aspergillus alliaceus, Cunninghamella blakesleeana

NCBI PubMed ID: 26235165
Publication DOI: 10.1248/cpb.c15-00037
Journal NLM ID: 0377775
Publisher: Pharmaceutical Society Of Japan
Correspondence: rimikell@olemiss.edu
Institutions: School of Pharmacy, King Saud University, Riyadh, Saudi Arabia, National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, USA, Department of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, USA
Methods: 13C NMR, 1H NMR, IR, TLC, biological assays, UV, extraction, optical rotation measurement, CC, cell growth, HR-ESI-MS, antibacterial assay, evaporation, antifungal activity test, antimalarial assays, antileishmanial assays

flavonoid, microbial metabolism, Beauveria bassiana, Mucor ramannianus, Aspergillus alliaceus, Cunninghamella blakesleeana