Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi

Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi

Combining chemical and microbiological methods using entomopathogenic filamentous fungi makes obtaining flavonoid glycosides possible. In the presented study, biotransformations were carried out in cultures of <i>Beauveria bassiana</i> KCH J1.5, <i>Isaria fumosorosea</i> KCH...

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Bibliographic Details
Main Authors: Martyna Perz, Agnieszka Krawczyk-Łebek, Monika Dymarska, Tomasz Janeczko, Edyta Kostrzewa-Susłow
Format: Article
Language:English
Published: MDPI AG 2023-05-01
Series:International Journal of Molecular Sciences
Subjects:
biotransformations
methyl group
nitro group
chlorine
bromine
<i>Beauveria bassiana</i>
Online Access:https://www.mdpi.com/1422-0067/24/11/9500
Description
Summary:Combining chemical and microbiological methods using entomopathogenic filamentous fungi makes obtaining flavonoid glycosides possible. In the presented study, biotransformations were carried out in cultures of <i>Beauveria bassiana</i> KCH J1.5, <i>Isaria fumosorosea</i> KCH J2, and <i>Isaria farinosa</i> KCH J2.6 strains on six flavonoid compounds obtained in chemical synthesis. As a result of the biotransformation of 6-methyl-8-nitroflavanone using the strain <i>I. fumosorosea</i> KCH J2, two products were obtained: 6-methyl-8-nitro-2-phenylchromane 4-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside and 8-nitroflavan-4-ol 6-methylene-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. 8-Bromo-6-chloroflavanone was transformed by this strain to 8-bromo-6-chloroflavan-4-ol 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. As a result of microbial transformation by <i>I. farinosa</i> KCH J2.6 effectively biotransformed only 8-bromo-6-chloroflavone into 8-bromo-6-chloroflavone 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. <i>B. bassiana</i> KCH J1.5 was able to transform 6-methyl-8-nitroflavone to 6-methyl-8-nitroflavone 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, and 3′-bromo-5′-chloro-2′-hydroxychalcone to 8-bromo-6-chloroflavanone 3′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. None of the filamentous fungi used transformed 2′-hydroxy-5′-methyl-3′-nitrochalcone effectively. Obtained flavonoid derivatives could be used to fight against antibiotic-resistant bacteria. To the best of our knowledge, all the substrates and products presented in this work are new compounds and are described for the first time.
ISSN:1661-6596
1422-0067

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