Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds
Flavonoid compounds are secondary plant metabolites with numerous biological activities; they naturally occur mainly in the form of glycosides. The glucosyl moiety attached to the flavonoid core makes them more stable and water-soluble. The methyl derivatives of flavonoids also show increased stabil...
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MDPI AG
2022-05-01
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| Series: | International Journal of Molecular Sciences |
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| author | Agnieszka Krawczyk-Łebek Monika Dymarska Tomasz Janeczko Edyta Kostrzewa-Susłow |
| author_facet | Agnieszka Krawczyk-Łebek Monika Dymarska Tomasz Janeczko Edyta Kostrzewa-Susłow |
| author_sort | Agnieszka Krawczyk-Łebek |
| collection | DOAJ |
| description | Flavonoid compounds are secondary plant metabolites with numerous biological activities; they naturally occur mainly in the form of glycosides. The glucosyl moiety attached to the flavonoid core makes them more stable and water-soluble. The methyl derivatives of flavonoids also show increased stability and intestinal absorption. Our study showed that such flavonoids can be obtained by combined chemical and biotechnological methods with entomopathogenic filamentous fungi as glycosylation biocatalysts. In the current paper, two flavonoids, i.e., 2′-hydroxy-4-methylchalcone and 4′-methylflavone, have been synthesized and biotransformed in the cultures of two strains of entomopathogenic filamentous fungi <i>Isaria fumosorosea</i> KCH J2 and <i>Beauveria bassiana</i> KCH J1.5. Biotransformation of 2′-hydroxy-4-methylchalcone resulted in the formation of two dihydrochalcone glucopyranoside derivatives in the culture of <i>I. fumosorosea</i> KCH J2 and chalcone glucopyranoside derivative in the case of <i>B. bassiana</i> KCH J1.5. 4′-Methylflavone was transformed in the culture of <i>I. fumosorosea</i> KCH J2 into four products, i.e., 4′-hydroxymethylflavone, flavone 4′-methylene-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-(4″-<i>O</i>-methyl)-glucopyranoside, flavone 4′-carboxylic acid, and 4′-methylflavone 3-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-(4″-<i>O</i>-methyl)-glucopyranoside. 4′-Methylflavone was not efficiently biotransformed in the culture of <i>B. bassiana</i> KCH J1.5. The computer-aided simulations based on the chemical structures of the obtained compounds showed their improved physicochemical properties and antimicrobial, anticarcinogenic, hepatoprotective, and cardioprotective potential. |
| first_indexed | 2024-03-10T03:44:07Z |
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| spelling | doaj.art-1a9a6965b85e4f6b9a784835902bc7e82023-11-23T11:24:37ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-05-012310555810.3390/ijms23105558Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active CompoundsAgnieszka Krawczyk-Łebek0Monika Dymarska1Tomasz Janeczko2Edyta Kostrzewa-Susłow3Department of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandDepartment of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandFlavonoid compounds are secondary plant metabolites with numerous biological activities; they naturally occur mainly in the form of glycosides. The glucosyl moiety attached to the flavonoid core makes them more stable and water-soluble. The methyl derivatives of flavonoids also show increased stability and intestinal absorption. Our study showed that such flavonoids can be obtained by combined chemical and biotechnological methods with entomopathogenic filamentous fungi as glycosylation biocatalysts. In the current paper, two flavonoids, i.e., 2′-hydroxy-4-methylchalcone and 4′-methylflavone, have been synthesized and biotransformed in the cultures of two strains of entomopathogenic filamentous fungi <i>Isaria fumosorosea</i> KCH J2 and <i>Beauveria bassiana</i> KCH J1.5. Biotransformation of 2′-hydroxy-4-methylchalcone resulted in the formation of two dihydrochalcone glucopyranoside derivatives in the culture of <i>I. fumosorosea</i> KCH J2 and chalcone glucopyranoside derivative in the case of <i>B. bassiana</i> KCH J1.5. 4′-Methylflavone was transformed in the culture of <i>I. fumosorosea</i> KCH J2 into four products, i.e., 4′-hydroxymethylflavone, flavone 4′-methylene-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-(4″-<i>O</i>-methyl)-glucopyranoside, flavone 4′-carboxylic acid, and 4′-methylflavone 3-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-(4″-<i>O</i>-methyl)-glucopyranoside. 4′-Methylflavone was not efficiently biotransformed in the culture of <i>B. bassiana</i> KCH J1.5. The computer-aided simulations based on the chemical structures of the obtained compounds showed their improved physicochemical properties and antimicrobial, anticarcinogenic, hepatoprotective, and cardioprotective potential.https://www.mdpi.com/1422-0067/23/10/5558biotransformationsmethylflavonoidsglycosylation4-<i>O</i>-methylglucopyranoside<i>Beauveria bassiana</i><i>Isaria fumosorosea</i> |
| spellingShingle | Agnieszka Krawczyk-Łebek Monika Dymarska Tomasz Janeczko Edyta Kostrzewa-Susłow Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds International Journal of Molecular Sciences biotransformations methylflavonoids glycosylation 4-<i>O</i>-methylglucopyranoside <i>Beauveria bassiana</i> <i>Isaria fumosorosea</i> |
| title | Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds |
| title_full | Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds |
| title_fullStr | Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds |
| title_full_unstemmed | Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds |
| title_short | Glycosylation of Methylflavonoids in the Cultures of Entomopathogenic Filamentous Fungi as a Tool for Obtaining New Biologically Active Compounds |
| title_sort | glycosylation of methylflavonoids in the cultures of entomopathogenic filamentous fungi as a tool for obtaining new biologically active compounds |
| topic | biotransformations methylflavonoids glycosylation 4-<i>O</i>-methylglucopyranoside <i>Beauveria bassiana</i> <i>Isaria fumosorosea</i> |
| url | https://www.mdpi.com/1422-0067/23/10/5558 |
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