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Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi.

ABSTRACT: The synthesis and biotransformation of five flavones containing methoxy substituents in the B ring: 2'-, 3'-, 4'-methoxyflavones, 2',5'-dimethoxyflavone and 3',4',5'-trimethoxyflavone are described. Strains of entomopathogenic filamentous fungi were used as biocatalysts. Five strains of the species Beauveria bassiana (KCh J1.5, J2.1, J3.2, J1, BBT), two of the species Beauveria caledonica (KCh J3.3, J3.4), one of Isaria fumosorosea (KCh J2) and one of Isaria farinosa (KCh KW 1.1) were investigated. Both the number and the place of attachment of the methoxy groups in the flavonoid structure influenced the biotransformation rate and the amount of nascent products. Based on the structures of products and semi-products, it can be concluded that their formation is the result of a cascading process. As a result of enzymes produced in the cells of the tested strains, the test compounds undergo progressive demethylation and/or hydroxylation and 4-O-methylglucosylation. Thirteen novel flavonoid 4-O-methylglucosides and five hydroxy flavones were isolated and identified.

SUBMITTER: Luzny M

PROVIDER: S-EPMC7503753 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi.

Łużny Mateusz M Tronina Tomasz T Kozłowska Ewa E Dymarska Monika M Popłoński Jarosław J Łyczko Jacek J Kostrzewa-Susłow Edyta E Janeczko Tomasz T

International journal of molecular sciences 20200825 17

The synthesis and biotransformation of five flavones containing methoxy substituents in the B ring: 2'-, 3'-, 4'-methoxyflavones, 2',5'-dimethoxyflavone and 3',4',5'-trimethoxyflavone are described. Strains of entomopathogenic filamentous fungi were used as biocatalysts. Five strains of the species Beauveria bassiana (KCh J1.5, J2.1, J3.2, J1, BBT), two of the species Beauveria caledonica (KCh J3.3, J3.4), one of Isaria fumosorosea (KCh J2) and one of Isaria farinosa ...[more]

PMID: 32854359

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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

Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi.

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Biotransformation of Methoxyflavones by Selected Entomopathogenic Filamentous Fungi.

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