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Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi.
Molecules. 2018 Jun 05; 23(6)M

Abstract

Entomopathogenic filamentous fungi of the genus Isaria are effective biocatalysts in the biotransformation of flavonoids as well as steroids. In the present study, the species Isariafumosorosea and Isariafarinosa isolated from the environment were used. Their catalytic capacity to carry out biotransformations of flavones-unsubstituted, with hydroxy- and amino-substituents as well as a hydroxylated isoflavone-was investigated. Biotransformations of flavone, 5-hydroxyflavone, 6-hydroxyflavone, 7-hydroxyflavone, and daidzein resulted in the formation of O-methylglucosides, in the case of flavone and 5-hydroxyflavone with additional hydroxylations. 7-Aminoflavone was transformed into two acetamido derivatives. The following products were obtained: From flavone⁻flavone 2'-O-β-d-(4''-O-methyl)-glucopyranoside, flavone 4'-O-β-d-(4''-O-methyl)-glucopyranoside and 3'-hydroxyflavone 4'-O-β-d-(4''-O-methyl)-glucopyranoside; from 5-hydroxyflavone⁻5-hydroxyflavone 4'-O-β-d-(4''-O-methyl)-glucopyranoside; from 6-hydroxyflavone⁻flavone 6-O-β-d-(4''-O-methyl)-glucopyranoside; from 7-hydroxyflavone⁻flavone 7-O-β-d-(4''-O-methyl)-glucopyranoside; from daidzein⁻daidzein 7-O-β-d-(4''-O-methyl)-glucopyranoside; and from 7-aminoflavone⁻7-acetamidoflavone and 7-acetamido-4'-hydroxyflavone. Seven of the products obtained by us have not been previously reported in the literature.

Authors+Show Affiliations

Department of Chemistry, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, Poland. monika.dymarska@gmail.com.Department of Chemistry, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, Poland. janeczko13@interia.pl.Department of Chemistry, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, Poland. ekostrzew@gmail.com.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29874813

Citation

Dymarska, Monika, et al. "Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi." Molecules (Basel, Switzerland), vol. 23, no. 6, 2018.
Dymarska M, Janeczko T, Kostrzewa-Susłow E. Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi. Molecules. 2018;23(6).
Dymarska, M., Janeczko, T., & Kostrzewa-Susłow, E. (2018). Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi. Molecules (Basel, Switzerland), 23(6). https://doi.org/10.3390/molecules23061356
Dymarska M, Janeczko T, Kostrzewa-Susłow E. Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi. Molecules. 2018 Jun 5;23(6) PubMed PMID: 29874813.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi. AU - Dymarska,Monika, AU - Janeczko,Tomasz, AU - Kostrzewa-Susłow,Edyta, Y1 - 2018/06/05/ PY - 2018/04/20/received PY - 2018/05/30/revised PY - 2018/06/01/accepted PY - 2018/6/8/entrez PY - 2018/6/8/pubmed PY - 2018/10/23/medline KW - 5-hydroxyflavone KW - 6-hydroxyflavone KW - 7-aminoflavone KW - 7-hydroxyflavone KW - Isaria farinosa KW - Isaria fumosorosea KW - biotransformations KW - daidzein KW - flavone JF - Molecules (Basel, Switzerland) JO - Molecules VL - 23 IS - 6 N2 - Entomopathogenic filamentous fungi of the genus Isaria are effective biocatalysts in the biotransformation of flavonoids as well as steroids. In the present study, the species Isariafumosorosea and Isariafarinosa isolated from the environment were used. Their catalytic capacity to carry out biotransformations of flavones-unsubstituted, with hydroxy- and amino-substituents as well as a hydroxylated isoflavone-was investigated. Biotransformations of flavone, 5-hydroxyflavone, 6-hydroxyflavone, 7-hydroxyflavone, and daidzein resulted in the formation of O-methylglucosides, in the case of flavone and 5-hydroxyflavone with additional hydroxylations. 7-Aminoflavone was transformed into two acetamido derivatives. The following products were obtained: From flavone⁻flavone 2'-O-β-d-(4''-O-methyl)-glucopyranoside, flavone 4'-O-β-d-(4''-O-methyl)-glucopyranoside and 3'-hydroxyflavone 4'-O-β-d-(4''-O-methyl)-glucopyranoside; from 5-hydroxyflavone⁻5-hydroxyflavone 4'-O-β-d-(4''-O-methyl)-glucopyranoside; from 6-hydroxyflavone⁻flavone 6-O-β-d-(4''-O-methyl)-glucopyranoside; from 7-hydroxyflavone⁻flavone 7-O-β-d-(4''-O-methyl)-glucopyranoside; from daidzein⁻daidzein 7-O-β-d-(4''-O-methyl)-glucopyranoside; and from 7-aminoflavone⁻7-acetamidoflavone and 7-acetamido-4'-hydroxyflavone. Seven of the products obtained by us have not been previously reported in the literature. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/29874813/Biotransformations_of_Flavones_and_an_Isoflavone__Daidzein__in_Cultures_of_Entomopathogenic_Filamentous_Fungi_ L2 - http://www.mdpi.com/resolver?pii=molecules23061356 DB - PRIME DP - Unbound Medicine ER -