Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| Outros Autores: | , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da UFMG |
| Texto Completo: | https://doi.org/10.3390/jof7121079 http://hdl.handle.net/1843/59657 https://orcid.org/0000-0002-7928-9921 https://orcid.org/0000-0001-8190-6127 https://orcid.org/0000-0002-8831-1609 https://orcid.org/0000-0002-8612-0593 https://orcid.org/0000-0002-5307-4164 https://orcid.org/0000-0001-6002-4977 |
Resumo: | CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior |
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2023-10-18T20:53:36Z2023-10-18T20:53:36Z2021-12-15712107917https://doi.org/10.3390/jof71210792309-608Xhttp://hdl.handle.net/1843/59657https://orcid.org/0000-0002-7928-9921https://orcid.org/0000-0001-8190-6127https://orcid.org/0000-0002-8831-1609https://orcid.org/0000-0002-8612-0593https://orcid.org/0000-0002-5307-4164https://orcid.org/0000-0001-6002-4977CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorClovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus Botrytis cinerea. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of B. cinerea. Further development of both classes of antifungal agent requires exploration of the structure–activity relationships for the antifungal effects on B. cinerea 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 (2b, 2d, 2f–2h, and 4c–4e); the evaluation of their antifungal properties against B. cinerea, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of Lactuca sativa (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against B. cinerea for 2d, 2h, 4c and 4d. In general terms, while 2-alkoxyclovan-9-ols (2a–2e) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (2f–2i) and 8-alkoxyisocaryolan-9-ols (4a–4d), where stimulating effects would make them suitable candidates for application to plantsengUniversidade Federal de Minas GeraisUFMGBrasilICX - DEPARTAMENTO DE QUÍMICAJournal of FungiQuímicaFungosAtividade antifúngicaBotrytis cinereaAntifungalPhytotoxic activityClovaneIsocaryolaneLactuca sativaSynthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanolsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://www.mdpi.com/2309-608X/7/12/1079Adrianade Almeida Pinto BracarenseRosa Durán-patrónAntonio J. Macías-sánchezJociani AscariGiovanni Gontijo de SouzaThays Silva OliveiraAntonio Ruano-gonzálezAna A. PintoMaria Amélia Diamantino BoaventuraJacqueline Aparecida TakahashiIsidro G. Colladoapplication/pdfinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGLICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/59657/1/License.txtfa505098d172de0bc8864fc1287ffe22MD51ORIGINALSynthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols.pdfSynthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols.pdfapplication/pdf1788093https://repositorio.ufmg.br/bitstream/1843/59657/2/Synthesis%2c%20Fungitoxic%20Activity%20against%20Botrytis%20cinerea%20and%20Phytotoxicity%20of%20Alkoxyclovanols%20and%20Alkoxyisocaryolanols.pdf7d3bc707cbe99a0ce547b0fb43e5bd10MD521843/596572023-10-18 17:53:36.639oai:repositorio.ufmg.br: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Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2023-10-18T20:53:36Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false |
| dc.title.pt_BR.fl_str_mv |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| spellingShingle |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols Adrianade Almeida Pinto Bracarense Botrytis cinerea Antifungal Phytotoxic activity Clovane Isocaryolane Lactuca sativa Química Fungos Atividade antifúngica |
| title_short |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_full |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_fullStr |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_full_unstemmed |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| title_sort |
Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols |
| author |
Adrianade Almeida Pinto Bracarense |
| author_facet |
Adrianade Almeida Pinto Bracarense Rosa Durán-patrón Antonio J. Macías-sánchez 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 |
| author_role |
author |
| author2 |
Rosa Durán-patrón Antonio J. Macías-sánchez 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 |
| author2_role |
author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Adrianade Almeida Pinto Bracarense Rosa Durán-patrón Antonio J. Macías-sánchez 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 |
| dc.subject.por.fl_str_mv |
Botrytis cinerea Antifungal Phytotoxic activity Clovane Isocaryolane Lactuca sativa |
| topic |
Botrytis cinerea Antifungal Phytotoxic activity Clovane Isocaryolane Lactuca sativa Química Fungos Atividade antifúngica |
| dc.subject.other.pt_BR.fl_str_mv |
Química Fungos Atividade antifúngica |
| description |
CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior |
| publishDate |
2021 |
| dc.date.issued.fl_str_mv |
2021-12-15 |
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2023-10-18T20:53:36Z |
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2023-10-18T20:53:36Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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http://hdl.handle.net/1843/59657 |
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https://doi.org/10.3390/jof7121079 |
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2309-608X |
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https://orcid.org/0000-0002-7928-9921 https://orcid.org/0000-0001-8190-6127 https://orcid.org/0000-0002-8831-1609 https://orcid.org/0000-0002-8612-0593 https://orcid.org/0000-0002-5307-4164 https://orcid.org/0000-0001-6002-4977 |
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https://doi.org/10.3390/jof7121079 http://hdl.handle.net/1843/59657 https://orcid.org/0000-0002-7928-9921 https://orcid.org/0000-0001-8190-6127 https://orcid.org/0000-0002-8831-1609 https://orcid.org/0000-0002-8612-0593 https://orcid.org/0000-0002-5307-4164 https://orcid.org/0000-0001-6002-4977 |
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2309-608X |
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eng |
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eng |
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Journal of Fungi |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Universidade Federal de Minas Gerais |
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UFMG |
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Brasil |
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ICX - DEPARTAMENTO DE QUÍMICA |
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Universidade Federal de Minas Gerais |
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reponame:Repositório Institucional da UFMG instname:Universidade Federal de Minas Gerais (UFMG) instacron:UFMG |
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