Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>

<i>Botrytis cinerea</i> is a ubiquitous fungus that affects hundreds of plants, resulting in economic losses to the horticulture and fruit industry. The search for new antifungal agents is a matter of current interest. Thus, in this work a series of geranylated phenols in which the side...

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Autores principales:	Mauricio Soto, Ana Estevez-Braun, Ángel Amesty, Julia Kluepfel, Susana Restrepo, Katy Diaz, Luis Espinoza, Andrés F. Olea, Lautaro Taborga
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Botrytis cinerea</i> hydrated geranylated phenols docking synthesis fungicidal Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/566a6516f25145ef9e0867e3fbdb27c8
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spelling	oai:doaj.org-article:566a6516f25145ef9e0867e3fbdb27c82021-11-25T18:27:27ZSynthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>10.3390/molecules262268151420-3049https://doaj.org/article/566a6516f25145ef9e0867e3fbdb27c82021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6815https://doaj.org/toc/1420-3049<i>Botrytis cinerea</i> is a ubiquitous fungus that affects hundreds of plants, resulting in economic losses to the horticulture and fruit industry. The search for new antifungal agents is a matter of current interest. Thus, in this work a series of geranylated phenols in which the side alkyl chain has been hydrated have been synthesized, and their activity against <i>B. cinerea</i> has been evaluated. The coupling of phenol and geraniol has been accomplished under microwave irradiation obtaining the highest reaction yields in the shortest reaction times. Hydration of the side chain was carried out in dioxane with <i>p</i>-toluenesulfonic acid polymer-bound as the catalyst. All synthesized compounds were tested against <i>B. cinerea</i> using the growth inhibition assay and EC<sub>50</sub> values were determined. The results show that activity depends on the number and nature of functional groups in the phenol ring and hydration degree of the geranyl chain. The most active compound is 1,4-dihydroquinone with one hydroxyl group attached at the end of the alkyl chain. Results from a molecular docking study suggest that hydroxyl groups in the phenol ring and alkyl chain are important in the binding of compounds to the active site, and that the experimental antifungal activity correlates with the number of H-bond that can be formed in the binding site.Mauricio SotoAna Estevez-BraunÁngel AmestyJulia KluepfelSusana RestrepoKaty DiazLuis EspinozaAndrés F. OleaLautaro TaborgaMDPI AGarticle<i>Botrytis cinerea</i>hydrated geranylated phenolsdockingsynthesisfungicidalOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6815, p 6815 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Botrytis cinerea</i> hydrated geranylated phenols docking synthesis fungicidal Organic chemistry QD241-441
spellingShingle	<i>Botrytis cinerea</i> hydrated geranylated phenols docking synthesis fungicidal Organic chemistry QD241-441 Mauricio Soto Ana Estevez-Braun Ángel Amesty Julia Kluepfel Susana Restrepo Katy Diaz Luis Espinoza Andrés F. Olea Lautaro Taborga Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>
description	<i>Botrytis cinerea</i> is a ubiquitous fungus that affects hundreds of plants, resulting in economic losses to the horticulture and fruit industry. The search for new antifungal agents is a matter of current interest. Thus, in this work a series of geranylated phenols in which the side alkyl chain has been hydrated have been synthesized, and their activity against <i>B. cinerea</i> has been evaluated. The coupling of phenol and geraniol has been accomplished under microwave irradiation obtaining the highest reaction yields in the shortest reaction times. Hydration of the side chain was carried out in dioxane with <i>p</i>-toluenesulfonic acid polymer-bound as the catalyst. All synthesized compounds were tested against <i>B. cinerea</i> using the growth inhibition assay and EC<sub>50</sub> values were determined. The results show that activity depends on the number and nature of functional groups in the phenol ring and hydration degree of the geranyl chain. The most active compound is 1,4-dihydroquinone with one hydroxyl group attached at the end of the alkyl chain. Results from a molecular docking study suggest that hydroxyl groups in the phenol ring and alkyl chain are important in the binding of compounds to the active site, and that the experimental antifungal activity correlates with the number of H-bond that can be formed in the binding site.
format	article
author	Mauricio Soto Ana Estevez-Braun Ángel Amesty Julia Kluepfel Susana Restrepo Katy Diaz Luis Espinoza Andrés F. Olea Lautaro Taborga
author_facet	Mauricio Soto Ana Estevez-Braun Ángel Amesty Julia Kluepfel Susana Restrepo Katy Diaz Luis Espinoza Andrés F. Olea Lautaro Taborga
author_sort	Mauricio Soto
title	Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>
title_short	Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>
title_full	Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>
title_fullStr	Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>
title_full_unstemmed	Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>
title_sort	synthesis and fungicidal activity of hydrated geranylated phenols against <i>botrytis cinerea</i>
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/566a6516f25145ef9e0867e3fbdb27c8
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Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against <i>Botrytis cinerea</i>

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