Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols
Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus <i>Botrytis cinerea</i>. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of <i>B. cinerea</i&...
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| Format: | Article |
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MDPI AG
2021-12-01
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| Series: | Journal of Fungi |
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| Online Access: | https://www.mdpi.com/2309-608X/7/12/1079 |
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| author | Adriana de Almeida Pinto Bracarense Jociani Ascari Giovanni Gontijo de Souza Thays Silva Oliveira Antonio Ruano-González Ana A. Pinto Maria Amélia Diamantino Boaventura Jacqueline Aparecida Takahashi Isidro G. Collado Rosa Durán-Patrón Antonio J. Macías-Sánchez |
| author_facet | Adriana de Almeida Pinto Bracarense Jociani Ascari Giovanni Gontijo de Souza Thays Silva Oliveira Antonio Ruano-González Ana A. Pinto Maria Amélia Diamantino Boaventura Jacqueline Aparecida Takahashi Isidro G. Collado Rosa Durán-Patrón Antonio J. Macías-Sánchez |
| author_sort | Adriana de Almeida Pinto Bracarense |
| collection | DOAJ |
| description | Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus <i>Botrytis cinerea</i>. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of <i>B. cinerea</i>. Further development of both classes of antifungal agent requires exploration of the structure–activity relationships for the antifungal effects on <i>B. cinerea</i> and phytotoxic effects on a model crop. In this paper, we report on the preparation of a series of alkoxy-clovane and -isocaryolane derivatives, some of them described here for the first time (<b>2b</b>, <b>2d</b>, <b>2f</b>–<b>2h</b>, and <b>4c</b>–<b>4e</b>); the evaluation of their antifungal properties against <i>B. cinerea</i>, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of <i>Lactuca sativa</i> (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against <i>B. cinerea</i> for <b>2d</b>, <b>2h</b>, <b>4c</b> and <b>4d</b>. In general terms, while 2-alkoxyclovan-9-ols (<b>2a</b>–<b>2e</b>) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (<b>2f</b>–<b>2i</b>) and 8-alkoxyisocaryolan-9-ols (<b>4a</b>–<b>4d</b>), where stimulating effects would make them suitable candidates for application to plants. |
| first_indexed | 2024-03-10T03:47:12Z |
| format | Article |
| id | doaj.art-b5963c10522e4054983e92ac2521d7fd |
| institution | Directory Open Access Journal |
| issn | 2309-608X |
| language | English |
| last_indexed | 2024-03-10T03:47:12Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Journal of Fungi |
| spelling | doaj.art-b5963c10522e4054983e92ac2521d7fd2023-11-23T09:05:33ZengMDPI AGJournal of Fungi2309-608X2021-12-01712107910.3390/jof7121079Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and AlkoxyisocaryolanolsAdriana de Almeida Pinto Bracarense0Jociani Ascari1Giovanni Gontijo de Souza2Thays Silva Oliveira3Antonio Ruano-González4Ana A. Pinto5Maria Amélia Diamantino Boaventura6Jacqueline Aparecida Takahashi7Isidro G. Collado8Rosa Durán-Patrón9Antonio J. Macías-Sánchez10Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Presidente Antônio Carlos, 6627, Belo Horizonte 31270-901, MG, BrazilDepartamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Presidente Antônio Carlos, 6627, Belo Horizonte 31270-901, MG, BrazilDepartamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Presidente Antônio Carlos, 6627, Belo Horizonte 31270-901, MG, BrazilDepartamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Presidente Antônio Carlos, 6627, Belo Horizonte 31270-901, MG, BrazilDepartamento 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, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Presidente Antônio Carlos, 6627, Belo Horizonte 31270-901, MG, BrazilDepartamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Av. Presidente Antônio Carlos, 6627, Belo Horizonte 31270-901, MG, BrazilDepartamento 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, SpainClovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus <i>Botrytis cinerea</i>. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of <i>B. cinerea</i>. Further development of both classes of antifungal agent requires exploration of the structure–activity relationships for the antifungal effects on <i>B. cinerea</i> and phytotoxic effects on a model crop. In this paper, we report on the preparation of a series of alkoxy-clovane and -isocaryolane derivatives, some of them described here for the first time (<b>2b</b>, <b>2d</b>, <b>2f</b>–<b>2h</b>, and <b>4c</b>–<b>4e</b>); the evaluation of their antifungal properties against <i>B. cinerea</i>, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of <i>Lactuca sativa</i> (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against <i>B. cinerea</i> for <b>2d</b>, <b>2h</b>, <b>4c</b> and <b>4d</b>. In general terms, while 2-alkoxyclovan-9-ols (<b>2a</b>–<b>2e</b>) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (<b>2f</b>–<b>2i</b>) and 8-alkoxyisocaryolan-9-ols (<b>4a</b>–<b>4d</b>), where stimulating effects would make them suitable candidates for application to plants.https://www.mdpi.com/2309-608X/7/12/1079<i>Botrytis cinerea</i>antifungalphytotoxic activityclovaneisocaryolane<i>Lactuca sativa</i> |
| spellingShingle | Adriana de Almeida Pinto Bracarense Jociani Ascari Giovanni Gontijo de Souza Thays Silva Oliveira Antonio Ruano-González Ana A. Pinto Maria Amélia Diamantino Boaventura Jacqueline Aparecida Takahashi Isidro G. Collado Rosa Durán-Patrón Antonio J. Macías-Sánchez Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols Journal of Fungi <i>Botrytis cinerea</i> antifungal phytotoxic activity clovane isocaryolane <i>Lactuca sativa</i> |
| title | Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_full | Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_fullStr | Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_full_unstemmed | Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_short | Synthesis, Fungitoxic Activity against <i>Botrytis cinerea</i> and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_sort | synthesis fungitoxic activity against i botrytis cinerea i and phytotoxicity of alkoxyclovanols and alkoxyisocaryolanols |
| topic | <i>Botrytis cinerea</i> antifungal phytotoxic activity clovane isocaryolane <i>Lactuca sativa</i> |
| url | https://www.mdpi.com/2309-608X/7/12/1079 |
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