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Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi

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 Isaria fumosorosea and Isaria farinosa isolated from the environment were used. Their catalytic capacity to carry out biotra...

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Detalles Bibliográficos
Autores principales: Dymarska, Monika, Janeczko, Tomasz, Kostrzewa-Susłow, Edyta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100588/
https://www.ncbi.nlm.nih.gov/pubmed/29874813
http://dx.doi.org/10.3390/molecules23061356
Descripción
Sumario: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 Isaria fumosorosea and Isaria farinosa 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.