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New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2'-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi.

ABSTRACT: Flavonoids, including chalcones, are more stable and bioavailable in the form of glycosylated and methylated derivatives. The combined chemical and biotechnological methods can be applied to obtain such compounds. In the present study, 2'-hydroxy-2-methylchalcone was synthesized and biotransformed in the cultures of entomopathogenic filamentous fungi Beauveria bassiana KCH J1.5, Isaria fumosorosea KCH J2 and Isaria farinosa KCH J2.6, which have been known for their extensive enzymatic system and ability to perform glycosylation of flavonoids. As a result, five new glycosylated dihydrochalcones were obtained. Biotransformation of 2'-hydroxy-2-methylchalcone by B. bassiana KCH J1.5 resulted in four glycosylated dihydrochalcones: 2'-hydroxy-2-methyldihydrochalcone 3'-O-β-d-(4″-O-methyl)-glucopyranoside, 2',3-dihydroxy-2-methyldihydrochalcone 3'-O-β-d-(4″-O-methyl)-glucopyranoside, 2'-hydroxy-2-hydroxymethyldihydrochalcone 3'-O-β-d-(4″-O-methyl)-glucopyranoside, and 2',4-dihydroxy-2-methyldihydrochalcone 3'-O-β-d-(4″-O-methyl)-glucopyranoside. In the culture of I. fumosorosea KCH J2 only one product was formed-3-hydroxy-2-methyldihydrochalcone 2'-O-β-d-(4″-O-methyl)-glucopyranoside. Biotransformation performed by I. farinosa KCH J2.6 resulted in the formation of two products: 2'-hydroxy-2-methyldihydrochalcone 3'-O-β-d-(4″-O-methyl)-glucopyranoside and 2',3-dihydroxy-2-methyldihydrochalcone 3'-O-β-d-(4″-O-methyl)-glucopyranoside. The structures of all obtained products were established based on the NMR spectroscopy. All products mentioned above may be used in further studies as potentially bioactive compounds with improved stability and bioavailability. These compounds can be considered as flavor enhancers and potential sweeteners.

SUBMITTER: Krawczyk-Lebek A

PROVIDER: S-EPMC8431761 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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.

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New Glycosylated Dihydrochalcones Obtained by Biotransformation of 2'-Hydroxy-2-methylchalcone in Cultures of Entomopathogenic Filamentous Fungi.

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