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Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism

Metabolism and in vitro fungitoxicity of perinaphthenone against three economically important fungi of the citrus, Botryodiplodia spp., Botrytis spp. and Fusarium spp. were investigated. Perinaphthenone exhibited significant antifungal activity at 62.5 μM and above. Even, the inhibitory effect again...

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Autores principales: Castaño, Luisa M., Gómez, Andrés F., Gil, Jesús, Durango, Diego
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7969902/
https://www.ncbi.nlm.nih.gov/pubmed/33748457
http://dx.doi.org/10.1016/j.heliyon.2021.e06354
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author Castaño, Luisa M.
Gómez, Andrés F.
Gil, Jesús
Durango, Diego
author_facet Castaño, Luisa M.
Gómez, Andrés F.
Gil, Jesús
Durango, Diego
author_sort Castaño, Luisa M.
collection PubMed
description Metabolism and in vitro fungitoxicity of perinaphthenone against three economically important fungi of the citrus, Botryodiplodia spp., Botrytis spp. and Fusarium spp. were investigated. Perinaphthenone exhibited significant antifungal activity at 62.5 μM and above. Even, the inhibitory effect against Fusarium spp. was significantly enhanced by exposure to direct light. In addition, the metabolism of perinaphthenone by the three fungi was studied. Results show that perinaphthenone was transformed almost completely during the first 24 h; two major products, whose concentration increased progressively during the twelve days of the test, were isolated and identified as 2,3-dihydro-1H-phenalen-1-ol and 2,3-dihydro-phenalen-1-one. Although both metabolic products displayed a considerable fungistatic effect, their slightly lower activities in comparison to perinaphthenone indicate that the transformation was a detoxification process. Studies on the relationship between the effect of some substituents in the perinaphthenone core and the mycelial growth inhibition of Botryodiplodia spp. were also carried out. Results show that the α, β-unsaturated carbonyl system is an important structural requirement but not the only to be necessary for the strong antifungal activity of perinaphthenone. In general, the antifungal properties of perinaphthenone may be modulated through the incorporation of substituents in the naphthalene core or in the α, β-unsaturated carbonyl system. It is concluded that perinaphthenone could be used as an antifungal agent or as a structural template for the development of new fungicide compounds.
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spelling pubmed-79699022021-03-19 Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism Castaño, Luisa M. Gómez, Andrés F. Gil, Jesús Durango, Diego Heliyon Research Article Metabolism and in vitro fungitoxicity of perinaphthenone against three economically important fungi of the citrus, Botryodiplodia spp., Botrytis spp. and Fusarium spp. were investigated. Perinaphthenone exhibited significant antifungal activity at 62.5 μM and above. Even, the inhibitory effect against Fusarium spp. was significantly enhanced by exposure to direct light. In addition, the metabolism of perinaphthenone by the three fungi was studied. Results show that perinaphthenone was transformed almost completely during the first 24 h; two major products, whose concentration increased progressively during the twelve days of the test, were isolated and identified as 2,3-dihydro-1H-phenalen-1-ol and 2,3-dihydro-phenalen-1-one. Although both metabolic products displayed a considerable fungistatic effect, their slightly lower activities in comparison to perinaphthenone indicate that the transformation was a detoxification process. Studies on the relationship between the effect of some substituents in the perinaphthenone core and the mycelial growth inhibition of Botryodiplodia spp. were also carried out. Results show that the α, β-unsaturated carbonyl system is an important structural requirement but not the only to be necessary for the strong antifungal activity of perinaphthenone. In general, the antifungal properties of perinaphthenone may be modulated through the incorporation of substituents in the naphthalene core or in the α, β-unsaturated carbonyl system. It is concluded that perinaphthenone could be used as an antifungal agent or as a structural template for the development of new fungicide compounds. Elsevier 2021-03-08 /pmc/articles/PMC7969902/ /pubmed/33748457 http://dx.doi.org/10.1016/j.heliyon.2021.e06354 Text en © 2021 The Authors http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Research Article
Castaño, Luisa M.
Gómez, Andrés F.
Gil, Jesús
Durango, Diego
Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism
title Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism
title_full Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism
title_fullStr Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism
title_full_unstemmed Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism
title_short Perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism
title_sort perinaphthenone and derivatives as control agents of phytopathogenic fungi: fungitoxicity and metabolism
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7969902/
https://www.ncbi.nlm.nih.gov/pubmed/33748457
http://dx.doi.org/10.1016/j.heliyon.2021.e06354
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