4′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents
Flavonoid compounds exhibit numerous biological activities and significantly impact human health. The presence of methyl or glucosyl moieties attached to the flavonoid core remarkably modifies their physicochemical properties and improves intestinal absorption. Combined chemical and biotechnological...
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MDPI AG
2022-05-01
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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 exhibit numerous biological activities and significantly impact human health. The presence of methyl or glucosyl moieties attached to the flavonoid core remarkably modifies their physicochemical properties and improves intestinal absorption. Combined chemical and biotechnological methods can be applied to obtain such derivatives. In the presented study, 4′-methylflavanone was synthesized and biotransformed in the cultures of three strains of entomopathogenic filamentous fungi, i.e., <i>Isaria fumosorosea</i> KCH J2, <i>Beauveria bassiana</i> KCH J1.5, and <i>Isaria farinosa</i> KCH J2.1. The microbial transformation products in the culture of <i>I. fumosorosea</i> KCH J2, flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, 2-phenyl-(4′-hydroxymethyl)-4-hydroxychromane, and flavanone 4′-carboxylic acid were obtained. Biotransformation of 4′-methylflavanone in the culture of <i>B. bassiana</i> KCH J1.5 resulted in the formation of one main product, i.e., flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. In the case of <i>I. farinosa</i> KCH J2.6 as a biocatalyst, three products, i.e., flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, flavanone 4′-carboxylic acid, and 4′-hydroxymethylflavanone 4<i>-O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside were obtained. The Swiss-ADME online simulations confirmed the increase in water solubility of 4′-methylflavanone glycosides and analyses performed using the Way2Drug Pass Online prediction tool indicated that flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside and 4′-hydroxymethylflavanone 4<i>-O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, which had not been previously reported in the literature, are promising anticarcinogenic, antimicrobial, and hepatoprotective agents. |
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| last_indexed | 2024-03-10T03:45:42Z |
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| spelling | doaj.art-bc73bf6ecd3d4b08b034542de398af202023-11-23T11:21:29ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-05-012310537310.3390/ijms231053734′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective AgentsAgnieszka 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 exhibit numerous biological activities and significantly impact human health. The presence of methyl or glucosyl moieties attached to the flavonoid core remarkably modifies their physicochemical properties and improves intestinal absorption. Combined chemical and biotechnological methods can be applied to obtain such derivatives. In the presented study, 4′-methylflavanone was synthesized and biotransformed in the cultures of three strains of entomopathogenic filamentous fungi, i.e., <i>Isaria fumosorosea</i> KCH J2, <i>Beauveria bassiana</i> KCH J1.5, and <i>Isaria farinosa</i> KCH J2.1. The microbial transformation products in the culture of <i>I. fumosorosea</i> KCH J2, flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, 2-phenyl-(4′-hydroxymethyl)-4-hydroxychromane, and flavanone 4′-carboxylic acid were obtained. Biotransformation of 4′-methylflavanone in the culture of <i>B. bassiana</i> KCH J1.5 resulted in the formation of one main product, i.e., flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. In the case of <i>I. farinosa</i> KCH J2.6 as a biocatalyst, three products, i.e., flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, flavanone 4′-carboxylic acid, and 4′-hydroxymethylflavanone 4<i>-O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside were obtained. The Swiss-ADME online simulations confirmed the increase in water solubility of 4′-methylflavanone glycosides and analyses performed using the Way2Drug Pass Online prediction tool indicated that flavanone 4′-methylene-<i>O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside and 4′-hydroxymethylflavanone 4<i>-O</i>-<i>β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, which had not been previously reported in the literature, are promising anticarcinogenic, antimicrobial, and hepatoprotective agents.https://www.mdpi.com/1422-0067/23/10/5373biotransformations4′-methylflavanoneglycosylation<i>O</i>-methylglucosides<i>Beauveria bassiana</i><i>Isaria fumosorosea</i> |
| spellingShingle | Agnieszka Krawczyk-Łebek Monika Dymarska Tomasz Janeczko Edyta Kostrzewa-Susłow 4′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents International Journal of Molecular Sciences biotransformations 4′-methylflavanone glycosylation <i>O</i>-methylglucosides <i>Beauveria bassiana</i> <i>Isaria fumosorosea</i> |
| title | 4′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents |
| title_full | 4′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents |
| title_fullStr | 4′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents |
| title_full_unstemmed | 4′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents |
| title_short | 4′-Methylflavanone Glycosides Obtained Using Biotransformation in the Entomopathogenic Filamentous Fungi Cultures as Potential Anticarcinogenic, Antimicrobial, and Hepatoprotective Agents |
| title_sort | 4 methylflavanone glycosides obtained using biotransformation in the entomopathogenic filamentous fungi cultures as potential anticarcinogenic antimicrobial and hepatoprotective agents |
| topic | biotransformations 4′-methylflavanone glycosylation <i>O</i>-methylglucosides <i>Beauveria bassiana</i> <i>Isaria fumosorosea</i> |
| url | https://www.mdpi.com/1422-0067/23/10/5373 |
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