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Eleven Microbial Metabolites of 6-Hydroxyflavanone.
Chem Pharm Bull (Tokyo). 2015; 63(8):579-83.CP

Abstract

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.

Authors+Show Affiliations

National Center for Natural Products Research, School of Pharmacy, The University of Mississippi.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26235165

Citation

Mikell, Julie Rakel, et al. "Eleven Microbial Metabolites of 6-Hydroxyflavanone." Chemical & Pharmaceutical Bulletin, vol. 63, no. 8, 2015, pp. 579-83.
Mikell JR, Herath W, Khan IA. Eleven Microbial Metabolites of 6-Hydroxyflavanone. Chem Pharm Bull. 2015;63(8):579-83.
Mikell, J. R., Herath, W., & Khan, I. A. (2015). Eleven Microbial Metabolites of 6-Hydroxyflavanone. Chemical & Pharmaceutical Bulletin, 63(8), 579-83. https://doi.org/10.1248/cpb.c15-00037
Mikell JR, Herath W, Khan IA. Eleven Microbial Metabolites of 6-Hydroxyflavanone. Chem Pharm Bull. 2015;63(8):579-83. PubMed PMID: 26235165.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Eleven Microbial Metabolites of 6-Hydroxyflavanone. AU - Mikell,Julie Rakel, AU - Herath,Wimal, AU - Khan,Ikhlas Ahmad, PY - 2015/8/4/entrez PY - 2015/8/4/pubmed PY - 2016/5/3/medline SP - 579 EP - 83 JF - Chemical & pharmaceutical bulletin JO - Chem. Pharm. Bull. VL - 63 IS - 8 N2 - 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. SN - 1347-5223 UR - https://www.unboundmedicine.com/medline/citation/26235165/Eleven_Microbial_Metabolites_of_6_Hydroxyflavanone_ L2 - https://dx.doi.org/10.1248/cpb.c15-00037 DB - PRIME DP - Unbound Medicine ER -