Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i>
<i>Fusarium</i> is one of the most toxigenic phytopathogens causing diseases and reduced agricultural productivity worldwide. Current chemical fungicides exhibit toxicity against non-target organisms, triggering negative environmental impact, and are a danger to consumers. In order to ex...
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MDPI AG
2020-08-01
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| Series: | Antibiotics |
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| Online Access: | https://www.mdpi.com/2079-6382/9/9/537 |
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| author | Ghislain Wabo Fotso Bathelemy Ngameni Thomas E. Storr Bonaventure Tchaleu Ngadjui Sibongile Mafu G. Richard Stephenson |
| author_facet | Ghislain Wabo Fotso Bathelemy Ngameni Thomas E. Storr Bonaventure Tchaleu Ngadjui Sibongile Mafu G. Richard Stephenson |
| author_sort | Ghislain Wabo Fotso |
| collection | DOAJ |
| description | <i>Fusarium</i> is one of the most toxigenic phytopathogens causing diseases and reduced agricultural productivity worldwide. Current chemical fungicides exhibit toxicity against non-target organisms, triggering negative environmental impact, and are a danger to consumers. In order to explore the chemical diversity of plants for potential antifungal applications, crude extract and fractions from <i>Monotes kerstingii</i> were screened for their activity against two multi-resistant <i>Fusarium oxysporum</i> strains: <i>Fo32931</i> and <i>Fo4287</i>. Antifungal activity was evaluated by the determination of minimum inhibitory concentration (MIC) by broth dilution of fermentative yeasts using kinetic OD<sub>600 nm</sub> reading by a spectrophotometer. The <i>n</i>-butanol fraction showed the best activity against <i>Fo4287</i>. We screened eleven previously reported natural compounds isolated from different fractions, and a stilbene–coumarin 5-[(1<i>E</i>)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-3-methyl-2<i>H</i>-1-benzopyran-2-one (<b>1</b>) was the most active compound against both strains. Compound <b>1</b> was employed as a nucleophile with a selection of electrophilic derivatizing agents to synthesize five novel stilbene–coumarin analogues. These semisynthetic derivatives showed moderate activity against <i>Fo32931</i> with only prenylated derivative exhibiting activity comparable to the natural stilbene–coumarin (<b>1</b>), demonstrating the key role of the phenolic group. |
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| last_indexed | 2024-03-10T16:52:33Z |
| publishDate | 2020-08-01 |
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| series | Antibiotics |
| spelling | doaj.art-07c6b9d06ce64a51b30e04626014d35d2023-11-20T11:15:09ZengMDPI AGAntibiotics2079-63822020-08-019953710.3390/antibiotics9090537Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i>Ghislain Wabo Fotso0Bathelemy Ngameni1Thomas E. Storr2Bonaventure Tchaleu Ngadjui3Sibongile Mafu4G. Richard Stephenson5Department of Organic Chemistry, Faculty of Science University of Yaoundé I, P.O. Box 812 Yaoundé, CameroonDepartment of Pharmacognosy and Pharmaceutical Chemistry, Faculty of Medicine and Biomedical Sciences, University of Yaoundé I, P.O. Box 1364 Yaoundé, CameroonSchool of Chemistry, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, UKDepartment of Organic Chemistry, Faculty of Science University of Yaoundé I, P.O. Box 812 Yaoundé, CameroonDepartment of Biochemistry and Molecular Biology, University of Massachusetts, Amherst, MA 01003, USASchool of Chemistry, University of East Anglia, Norwich Research Park, Norwich NR4 7TJ, UK<i>Fusarium</i> is one of the most toxigenic phytopathogens causing diseases and reduced agricultural productivity worldwide. Current chemical fungicides exhibit toxicity against non-target organisms, triggering negative environmental impact, and are a danger to consumers. In order to explore the chemical diversity of plants for potential antifungal applications, crude extract and fractions from <i>Monotes kerstingii</i> were screened for their activity against two multi-resistant <i>Fusarium oxysporum</i> strains: <i>Fo32931</i> and <i>Fo4287</i>. Antifungal activity was evaluated by the determination of minimum inhibitory concentration (MIC) by broth dilution of fermentative yeasts using kinetic OD<sub>600 nm</sub> reading by a spectrophotometer. The <i>n</i>-butanol fraction showed the best activity against <i>Fo4287</i>. We screened eleven previously reported natural compounds isolated from different fractions, and a stilbene–coumarin 5-[(1<i>E</i>)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-3-methyl-2<i>H</i>-1-benzopyran-2-one (<b>1</b>) was the most active compound against both strains. Compound <b>1</b> was employed as a nucleophile with a selection of electrophilic derivatizing agents to synthesize five novel stilbene–coumarin analogues. These semisynthetic derivatives showed moderate activity against <i>Fo32931</i> with only prenylated derivative exhibiting activity comparable to the natural stilbene–coumarin (<b>1</b>), demonstrating the key role of the phenolic group.https://www.mdpi.com/2079-6382/9/9/537<i>Monotes kerstingii</i>antifungal activity<i>Fusarium oxysporum</i>semisynthesisstilbene–coumarins |
| spellingShingle | Ghislain Wabo Fotso Bathelemy Ngameni Thomas E. Storr Bonaventure Tchaleu Ngadjui Sibongile Mafu G. Richard Stephenson Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i> Antibiotics <i>Monotes kerstingii</i> antifungal activity <i>Fusarium oxysporum</i> semisynthesis stilbene–coumarins |
| title | Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i> |
| title_full | Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i> |
| title_fullStr | Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i> |
| title_full_unstemmed | Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i> |
| title_short | Synthesis of Novel Stilbene–Coumarin Derivatives and Antifungal Screening of <i>Monotes kerstingii</i>-Specialized Metabolites Against <i>Fusarium oxysporum</i> |
| title_sort | synthesis of novel stilbene coumarin derivatives and antifungal screening of i monotes kerstingii i specialized metabolites against i fusarium oxysporum i |
| topic | <i>Monotes kerstingii</i> antifungal activity <i>Fusarium oxysporum</i> semisynthesis stilbene–coumarins |
| url | https://www.mdpi.com/2079-6382/9/9/537 |
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