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Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea

Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a...

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Autores principales: Olea, Andrés F., Bravo, Angelica, Martínez, Rolando, Thomas, Mario, Sedan, Claudia, Espinoza, Luis, Zambrano, Elisabeth, Carvajal, Denisse, Silva-Moreno, Evelyn, Carrasco, Héctor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6479685/
https://www.ncbi.nlm.nih.gov/pubmed/30934962
http://dx.doi.org/10.3390/molecules24071239
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author Olea, Andrés F.
Bravo, Angelica
Martínez, Rolando
Thomas, Mario
Sedan, Claudia
Espinoza, Luis
Zambrano, Elisabeth
Carvajal, Denisse
Silva-Moreno, Evelyn
Carrasco, Héctor
author_facet Olea, Andrés F.
Bravo, Angelica
Martínez, Rolando
Thomas, Mario
Sedan, Claudia
Espinoza, Luis
Zambrano, Elisabeth
Carvajal, Denisse
Silva-Moreno, Evelyn
Carrasco, Héctor
author_sort Olea, Andrés F.
collection PubMed
description Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a series of phenylpropanoids derived from eugenol were synthesized and characterized. Their effects on the mycelial growth of a virulent and multi-resistant isolate of B. cinerea (PN2) have been evaluated and IC(50) values for the most active compounds range between 31–95 ppm. The antifungal activity exhibited by these compounds is strongly related to their chemical structure, i.e., increasing activity has been obtained by isomerization of the double bond or introduction of a nitro group on the aromatic ring. Based on the relationship between the fungicide activities and chemical structure, a mechanism of action is proposed. Finally, the activity of these compounds is higher than that reported for the commercial fungicide BC-1000 that is currently employed to combat this disease. Thus, our results suggest that these compounds are potential candidates to be used in the design of new and effective control with inspired natural compounds of this pathogen.
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spelling pubmed-64796852019-04-30 Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea Olea, Andrés F. Bravo, Angelica Martínez, Rolando Thomas, Mario Sedan, Claudia Espinoza, Luis Zambrano, Elisabeth Carvajal, Denisse Silva-Moreno, Evelyn Carrasco, Héctor Molecules Article Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a series of phenylpropanoids derived from eugenol were synthesized and characterized. Their effects on the mycelial growth of a virulent and multi-resistant isolate of B. cinerea (PN2) have been evaluated and IC(50) values for the most active compounds range between 31–95 ppm. The antifungal activity exhibited by these compounds is strongly related to their chemical structure, i.e., increasing activity has been obtained by isomerization of the double bond or introduction of a nitro group on the aromatic ring. Based on the relationship between the fungicide activities and chemical structure, a mechanism of action is proposed. Finally, the activity of these compounds is higher than that reported for the commercial fungicide BC-1000 that is currently employed to combat this disease. Thus, our results suggest that these compounds are potential candidates to be used in the design of new and effective control with inspired natural compounds of this pathogen. MDPI 2019-03-29 /pmc/articles/PMC6479685/ /pubmed/30934962 http://dx.doi.org/10.3390/molecules24071239 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Olea, Andrés F.
Bravo, Angelica
Martínez, Rolando
Thomas, Mario
Sedan, Claudia
Espinoza, Luis
Zambrano, Elisabeth
Carvajal, Denisse
Silva-Moreno, Evelyn
Carrasco, Héctor
Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea
title Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea
title_full Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea
title_fullStr Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea
title_full_unstemmed Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea
title_short Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea
title_sort antifungal activity of eugenol derivatives against botrytis cinerea
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6479685/
https://www.ncbi.nlm.nih.gov/pubmed/30934962
http://dx.doi.org/10.3390/molecules24071239
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