Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi
Combining chemical and microbiological methods using entomopathogenic filamentous fungi makes obtaining flavonoid glycosides possible. In the presented study, biotransformations were carried out in cultures of <i>Beauveria bassiana</i> KCH J1.5, <i>Isaria fumosorosea</i> KCH...
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MDPI AG
2023-05-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/11/9500 |
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| author | Martyna Perz Agnieszka Krawczyk-Łebek Monika Dymarska Tomasz Janeczko Edyta Kostrzewa-Susłow |
| author_facet | Martyna Perz Agnieszka Krawczyk-Łebek Monika Dymarska Tomasz Janeczko Edyta Kostrzewa-Susłow |
| author_sort | Martyna Perz |
| collection | DOAJ |
| description | Combining chemical and microbiological methods using entomopathogenic filamentous fungi makes obtaining flavonoid glycosides possible. In the presented study, biotransformations were carried out in cultures of <i>Beauveria bassiana</i> KCH J1.5, <i>Isaria fumosorosea</i> KCH J2, and <i>Isaria farinosa</i> KCH J2.6 strains on six flavonoid compounds obtained in chemical synthesis. As a result of the biotransformation of 6-methyl-8-nitroflavanone using the strain <i>I. fumosorosea</i> KCH J2, two products were obtained: 6-methyl-8-nitro-2-phenylchromane 4-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside and 8-nitroflavan-4-ol 6-methylene-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. 8-Bromo-6-chloroflavanone was transformed by this strain to 8-bromo-6-chloroflavan-4-ol 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. As a result of microbial transformation by <i>I. farinosa</i> KCH J2.6 effectively biotransformed only 8-bromo-6-chloroflavone into 8-bromo-6-chloroflavone 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. <i>B. bassiana</i> KCH J1.5 was able to transform 6-methyl-8-nitroflavone to 6-methyl-8-nitroflavone 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, and 3′-bromo-5′-chloro-2′-hydroxychalcone to 8-bromo-6-chloroflavanone 3′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. None of the filamentous fungi used transformed 2′-hydroxy-5′-methyl-3′-nitrochalcone effectively. Obtained flavonoid derivatives could be used to fight against antibiotic-resistant bacteria. To the best of our knowledge, all the substrates and products presented in this work are new compounds and are described for the first time. |
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| spelling | doaj.art-d93389de7fd946db9e04d57ad1e98c612023-11-18T07:59:58ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-05-012411950010.3390/ijms24119500Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous FungiMartyna Perz0Agnieszka Krawczyk-Łebek1Monika Dymarska2Tomasz Janeczko3Edyta Kostrzewa-Susłow4Department 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, PolandDepartment of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Science, Wrocław University of Environmental and Life Sciences, 50-375 Wrocław, PolandCombining chemical and microbiological methods using entomopathogenic filamentous fungi makes obtaining flavonoid glycosides possible. In the presented study, biotransformations were carried out in cultures of <i>Beauveria bassiana</i> KCH J1.5, <i>Isaria fumosorosea</i> KCH J2, and <i>Isaria farinosa</i> KCH J2.6 strains on six flavonoid compounds obtained in chemical synthesis. As a result of the biotransformation of 6-methyl-8-nitroflavanone using the strain <i>I. fumosorosea</i> KCH J2, two products were obtained: 6-methyl-8-nitro-2-phenylchromane 4-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside and 8-nitroflavan-4-ol 6-methylene-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. 8-Bromo-6-chloroflavanone was transformed by this strain to 8-bromo-6-chloroflavan-4-ol 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. As a result of microbial transformation by <i>I. farinosa</i> KCH J2.6 effectively biotransformed only 8-bromo-6-chloroflavone into 8-bromo-6-chloroflavone 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. <i>B. bassiana</i> KCH J1.5 was able to transform 6-methyl-8-nitroflavone to 6-methyl-8-nitroflavone 4′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside, and 3′-bromo-5′-chloro-2′-hydroxychalcone to 8-bromo-6-chloroflavanone 3′-<i>O-β</i>-D-(4″-<i>O</i>-methyl)-glucopyranoside. None of the filamentous fungi used transformed 2′-hydroxy-5′-methyl-3′-nitrochalcone effectively. Obtained flavonoid derivatives could be used to fight against antibiotic-resistant bacteria. To the best of our knowledge, all the substrates and products presented in this work are new compounds and are described for the first time.https://www.mdpi.com/1422-0067/24/11/9500biotransformationsmethyl groupnitro groupchlorinebromine<i>Beauveria bassiana</i> |
| spellingShingle | Martyna Perz Agnieszka Krawczyk-Łebek Monika Dymarska Tomasz Janeczko Edyta Kostrzewa-Susłow Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi International Journal of Molecular Sciences biotransformations methyl group nitro group chlorine bromine <i>Beauveria bassiana</i> |
| title | Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi |
| title_full | Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi |
| title_fullStr | Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi |
| title_full_unstemmed | Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi |
| title_short | Biotransformation of Flavonoids with -NO<sub>2</sub>, -CH<sub>3</sub> Groups and -Br, -Cl Atoms by Entomopathogenic Filamentous Fungi |
| title_sort | biotransformation of flavonoids with no sub 2 sub ch sub 3 sub groups and br cl atoms by entomopathogenic filamentous fungi |
| topic | biotransformations methyl group nitro group chlorine bromine <i>Beauveria bassiana</i> |
| url | https://www.mdpi.com/1422-0067/24/11/9500 |
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