Dataset Information

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

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-?-d-(4''-O-methyl)-glucopyranoside, flavone 4'-O-?-d-(4''-O-methyl)-glucopyranoside and 3'-hydroxyflavone 4'-O-?-d-(4''-O-methyl)-glucopyranoside; from 5-hydroxyflavone?5-hydroxyflavone 4'-O-?-d-(4''-O-methyl)-glucopyranoside; from 6-hydroxyflavone?flavone 6-O-?-d-(4''-O-methyl)-glucopyranoside; from 7-hydroxyflavone?flavone 7-O-?-d-(4''-O-methyl)-glucopyranoside; from daidzein?daidzein 7-O-?-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.

SUBMITTER: Dymarska M

PROVIDER: S-EPMC6100588 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Publications

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

Dymarska Monika M Janeczko Tomasz T Kostrzewa-Susłow Edyta E

Molecules (Basel, Switzerland) 20180605 6

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-hy ...[more]

PMID: 29874813

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Project description:BACKGROUND:Steroid compounds with a 6,19-oxirane bridge possess interesting biological activities including anticonvulsant and analgesic properties, bacteriostatic activity against Gram-positive bacteria and selective anti-glucocorticoid action, while lacking mineralocorticoid and progestagen activity. RESULTS:The study aimed to obtain new derivatives of 3?-acetyloxy-5?-chloro-6,19-oxidoandrostan-17-one by microbial transformation. Twelve filamentous fungal strains were used as catalysts, including entomopathogenic strains with specific activity in the transformation of steroid compounds. All selected strains were characterised by high biotransformation capacity for steroid compounds. However, high substrate conversions were obtained in the cultures of 8 strains: Beauveria bassiana KCh BBT, Beauveria caledonica KCh J3.4, Penicillium commune KCh W7, Penicillium chrysogenum KCh S4, Mucor hiemalis KCh W2, Fusarium acuminatum KCh S1, Trichoderma atroviride KCh TRW and Isaria farinosa KCh KW1.1. Based on gas chromatography (GC) and nuclear magnetic resonance (NMR) analyses, it was found that almost all strains hydrolysed the ester bond of the acetyl group. The strain M. hiemalis KCh W2 reduced the carbonyl group additionally. From the P. commune KCh W7 and P. chrysogenum KCh S4 strain cultures a product of D-ring Baeyer-Villiger oxidation was isolated, whereas from the culture of B. bassiana KCh BBT a product of hydroxylation at the 11? position and oxidation of the D ring was obtained. Three 11?-hydroxy derivatives were obtained in the culture of I. farinosa KCh KW1.1: 3?,11?-dihydroxy-5?-chloro-6,19-oxidoandrostan-17-one, 3?,11?,19-trihydroxy-5?-chloro-6,19-oxidoandrostan-17-one and 3?,11?-dihydroxy-5?-chloro-6,19-oxidoandrostan-17,19-dione. They are a result of consecutive reactions of hydrolysis of the acetyl group at C-3, 11?- hydroxylation, then hydroxylation at C-19 and its further oxidation to lactone. CONCLUSIONS:As a result of the biotransformations, seven steroid derivatives, not previously described in the literature, were obtained: 3?-hydroxy-5?-chloro-6,19-oxidoandrostan-17-one, 3?,17?-dihydroxy-5?-chloro-6,19-oxidoandrostane, 3?-hydroxy-5?-chloro-17?-oxa-D-homo-6,19-oxidoandrostan-17-one, 3?,11?-dihydroxy-5?-chloro-17?-oxa-D-homo-6,19-oxidoandrostan-17-one and the three above-mentioned 11?-hydroxy derivatives. This study will allow a better understanding and characterisation of the catalytic abilities of individual microorganisms, which is crucial for more accurate planning of experiments and achieving more predictable results.

Dataset Information

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

Publications

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

Similar Datasets

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