Cargando…

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...

Descripción completa

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
_version_ 1783348909623476224
author Dymarska, Monika
Janeczko, Tomasz
Kostrzewa-Susłow, Edyta
author_facet Dymarska, Monika
Janeczko, Tomasz
Kostrzewa-Susłow, Edyta
author_sort Dymarska, Monika
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6100588
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61005882018-11-13 Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi Dymarska, Monika Janeczko, Tomasz Kostrzewa-Susłow, Edyta Molecules Article 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. MDPI 2018-06-05 /pmc/articles/PMC6100588/ /pubmed/29874813 http://dx.doi.org/10.3390/molecules23061356 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Dymarska, Monika
Janeczko, Tomasz
Kostrzewa-Susłow, Edyta
Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi
title Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi
title_full Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi
title_fullStr Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi
title_full_unstemmed Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi
title_short Biotransformations of Flavones and an Isoflavone (Daidzein) in Cultures of Entomopathogenic Filamentous Fungi
title_sort biotransformations of flavones and an isoflavone (daidzein) in cultures of entomopathogenic filamentous fungi
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100588/
https://www.ncbi.nlm.nih.gov/pubmed/29874813
http://dx.doi.org/10.3390/molecules23061356
work_keys_str_mv AT dymarskamonika biotransformationsofflavonesandanisoflavonedaidzeininculturesofentomopathogenicfilamentousfungi
AT janeczkotomasz biotransformationsofflavonesandanisoflavonedaidzeininculturesofentomopathogenicfilamentousfungi
AT kostrzewasusłowedyta biotransformationsofflavonesandanisoflavonedaidzeininculturesofentomopathogenicfilamentousfungi