Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i>
Indanols are a family of chemical compounds that have been widely studied due to their broad range of biological activity. They are also important intermediates used as synthetic precursors to other products with important applications in pharmacology. Enantiomerically pure chloroindanol derivatives...
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MDPI AG
2020-11-01
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| Series: | Plants |
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| Online Access: | https://www.mdpi.com/2223-7747/9/12/1648 |
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| author | Cristina Pinedo-Rivilla Javier Moraga Guillermo Pérez-Sasián Alba Peña-Hernández Isidro G. Collado Josefina Aleu |
| author_facet | Cristina Pinedo-Rivilla Javier Moraga Guillermo Pérez-Sasián Alba Peña-Hernández Isidro G. Collado Josefina Aleu |
| author_sort | Cristina Pinedo-Rivilla |
| collection | DOAJ |
| description | Indanols are a family of chemical compounds that have been widely studied due to their broad range of biological activity. They are also important intermediates used as synthetic precursors to other products with important applications in pharmacology. Enantiomerically pure chloroindanol derivatives exhibiting antifungal activity against the phytopathogenic fungus <i>Botrytis cinerea</i> were prepared using biocatalytic methods. As a result of the biotransformation of racemic 6-chloroindanol (<b>1</b>) and 5-chloroindanol (<b>2</b>) by the fungus <i>B. cinerea</i>, the compounds <i>anti</i>-(+)-6-chloroindan-1,2-diol (<i>anti</i>-(+)-<b>7</b>), <i>anti</i>-(+)-5-chloroindan-1,3-diol (<i>anti</i>-(+)-<b>8</b>), <i>syn</i>-(+)-5-chloroindan-1,3-diol (<i>syn</i>-(+)-<b>8</b>), <i>syn</i>-(-)-5-chloroindan-1,3-diol (<i>syn</i>-(-)-<b>8</b>), and <i>anti</i>-(+)-5-chloroindan-1,2-diol (<i>anti</i>-(+)-<b>9</b>) were isolated for the first time. These products were characterized by spectroscopic techniques and their enantiomeric excesses studied by chromatographic techniques. The results obtained in the biotransformation seem to suggest that the fungus <i>B. cinerea</i> uses oxidation reactions as a detoxification mechanism. |
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| institution | Directory Open Access Journal |
| issn | 2223-7747 |
| language | English |
| last_indexed | 2024-03-10T14:33:45Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Plants |
| spelling | doaj.art-2903ce4b20ee43d8afa469e79ca396cd2023-11-20T22:19:36ZengMDPI AGPlants2223-77472020-11-01912164810.3390/plants9121648Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i>Cristina Pinedo-Rivilla0Javier Moraga1Guillermo Pérez-Sasián2Alba Peña-Hernández3Isidro G. Collado4Josefina Aleu5Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, 11510 Cádiz, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, 11510 Cádiz, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, 11510 Cádiz, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, 11510 Cádiz, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, 11510 Cádiz, SpainDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Puerto Real, 11510 Cádiz, SpainIndanols are a family of chemical compounds that have been widely studied due to their broad range of biological activity. They are also important intermediates used as synthetic precursors to other products with important applications in pharmacology. Enantiomerically pure chloroindanol derivatives exhibiting antifungal activity against the phytopathogenic fungus <i>Botrytis cinerea</i> were prepared using biocatalytic methods. As a result of the biotransformation of racemic 6-chloroindanol (<b>1</b>) and 5-chloroindanol (<b>2</b>) by the fungus <i>B. cinerea</i>, the compounds <i>anti</i>-(+)-6-chloroindan-1,2-diol (<i>anti</i>-(+)-<b>7</b>), <i>anti</i>-(+)-5-chloroindan-1,3-diol (<i>anti</i>-(+)-<b>8</b>), <i>syn</i>-(+)-5-chloroindan-1,3-diol (<i>syn</i>-(+)-<b>8</b>), <i>syn</i>-(-)-5-chloroindan-1,3-diol (<i>syn</i>-(-)-<b>8</b>), and <i>anti</i>-(+)-5-chloroindan-1,2-diol (<i>anti</i>-(+)-<b>9</b>) were isolated for the first time. These products were characterized by spectroscopic techniques and their enantiomeric excesses studied by chromatographic techniques. The results obtained in the biotransformation seem to suggest that the fungus <i>B. cinerea</i> uses oxidation reactions as a detoxification mechanism.https://www.mdpi.com/2223-7747/9/12/1648baker’s yeastlipasebiotransformation<i>Botrytis cinerea</i>chloroindanol derivatives |
| spellingShingle | Cristina Pinedo-Rivilla Javier Moraga Guillermo Pérez-Sasián Alba Peña-Hernández Isidro G. Collado Josefina Aleu Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i> Plants baker’s yeast lipase biotransformation <i>Botrytis cinerea</i> chloroindanol derivatives |
| title | Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i> |
| title_full | Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i> |
| title_fullStr | Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i> |
| title_full_unstemmed | Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i> |
| title_short | Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus <i>Botrytis cinerea</i> |
| title_sort | biocatalytic preparation of chloroindanol derivatives antifungal activity and detoxification by the phytopathogenic fungus i botrytis cinerea i |
| topic | baker’s yeast lipase biotransformation <i>Botrytis cinerea</i> chloroindanol derivatives |
| url | https://www.mdpi.com/2223-7747/9/12/1648 |
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