Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study

Autores
Dambolena, José Sebastián; López, Abel Gerardo; Meriles, Jose Manuel; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Fusarium is a ubiquitous hyalohyphomycete fungus usually isolated from food, which is 23 widespread in different environments (plant, grain, soil) and present at all latitudes. This 24 genus has been widely studied due to its ability to infect, cause tissue destruction and 25 produce mycotoxins on important crops such as corn, wheat and other small grains. 26 Over recent years, much effort has been directed at the search for new  antifungal 27 materials from natural sources, and many antimicrobial compounds coming from plants 28 have been identified. Although the essential oils and their components have been 29 recommended as fumigants for preservation of food commodities, little is known about30 the molecular properties related to the antifungal activity. In the present study, we 31 performed a QSAR study for the inhibition of Fusarium verticillioides growth by ten 32 natural phenolic compounds, which could serve as a guide for the rational design of 33 further inhibitors. The results of the experimental determinations demonstrated that in 34 terms of the antifungal activity of natural phenolic compounds on F. Verticillioides, the 35 following order was found: carvacrol > thymol > isoeugenol > eugenol > vanillin > 36 creosol > m-cresol> o-cresol, p-cresol, and guaiacol. Mathematical models based on 37 molecular properties, Lipophilicity, Molar refractivity and Saturated area were found to 38 be the descriptors that best explained the antifungal activity of these compounds. These 39 models could be used in future to predict the activity of new compounds and to guide 40 the search for the synthesis of phenolic compounds with the capacity to alter F. 41 verticillioides growth.
Fil: Dambolena, José Sebastián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: López, Abel Gerardo. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina
Fil: Meriles, Jose Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Rubinstein, Héctor Ramón. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Materia
Fusarium verticillioides
natural phenolic compounds
QSAR
lipophilicity
molar refractivity
saturated area
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
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Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/272309
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship studyDambolena, José SebastiánLópez, Abel GerardoMeriles, Jose ManuelRubinstein, Héctor RamónZygadlo, Julio AlbertoFusarium verticillioidesnatural phenolic compoundsQSARlipophilicitymolar refractivitysaturated areahttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Fusarium is a ubiquitous hyalohyphomycete fungus usually isolated from food, which is 23 widespread in different environments (plant, grain, soil) and present at all latitudes. This 24 genus has been widely studied due to its ability to infect, cause tissue destruction and 25 produce mycotoxins on important crops such as corn, wheat and other small grains. 26 Over recent years, much effort has been directed at the search for new  antifungal 27 materials from natural sources, and many antimicrobial compounds coming from plants 28 have been identified. Although the essential oils and their components have been 29 recommended as fumigants for preservation of food commodities, little is known about30 the molecular properties related to the antifungal activity. In the present study, we 31 performed a QSAR study for the inhibition of Fusarium verticillioides growth by ten 32 natural phenolic compounds, which could serve as a guide for the rational design of 33 further inhibitors. The results of the experimental determinations demonstrated that in 34 terms of the antifungal activity of natural phenolic compounds on F. Verticillioides, the 35 following order was found: carvacrol > thymol > isoeugenol > eugenol > vanillin > 36 creosol > m-cresol> o-cresol, p-cresol, and guaiacol. Mathematical models based on 37 molecular properties, Lipophilicity, Molar refractivity and Saturated area were found to 38 be the descriptors that best explained the antifungal activity of these compounds. These 39 models could be used in future to predict the activity of new compounds and to guide 40 the search for the synthesis of phenolic compounds with the capacity to alter F. 41 verticillioides growth.Fil: Dambolena, José Sebastián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: López, Abel Gerardo. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; ArgentinaFil: Meriles, Jose Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Rubinstein, Héctor Ramón. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; ArgentinaFil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaElsevier2012-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/272309Dambolena, José Sebastián; López, Abel Gerardo; Meriles, Jose Manuel; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto; Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study; Elsevier; Food Control; 28; 1; 11-2012; 163-1700956-7135CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0956713512002319info:eu-repo/semantics/altIdentifier/doi/10.1016/j.foodcont.2012.05.008info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:48:07Zoai:ri.conicet.gov.ar:11336/272309instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:48:08.108CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
title Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
spellingShingle Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
Dambolena, José Sebastián
Fusarium verticillioides
natural phenolic compounds
QSAR
lipophilicity
molar refractivity
saturated area
title_short Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
title_full Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
title_fullStr Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
title_full_unstemmed Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
title_sort Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study
dc.creator.none.fl_str_mv Dambolena, José Sebastián
López, Abel Gerardo
Meriles, Jose Manuel
Rubinstein, Héctor Ramón
Zygadlo, Julio Alberto
author Dambolena, José Sebastián
author_facet Dambolena, José Sebastián
López, Abel Gerardo
Meriles, Jose Manuel
Rubinstein, Héctor Ramón
Zygadlo, Julio Alberto
author_role author
author2 López, Abel Gerardo
Meriles, Jose Manuel
Rubinstein, Héctor Ramón
Zygadlo, Julio Alberto
author2_role author
author
author
author
dc.subject.none.fl_str_mv Fusarium verticillioides
natural phenolic compounds
QSAR
lipophilicity
molar refractivity
saturated area
topic Fusarium verticillioides
natural phenolic compounds
QSAR
lipophilicity
molar refractivity
saturated area
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Fusarium is a ubiquitous hyalohyphomycete fungus usually isolated from food, which is 23 widespread in different environments (plant, grain, soil) and present at all latitudes. This 24 genus has been widely studied due to its ability to infect, cause tissue destruction and 25 produce mycotoxins on important crops such as corn, wheat and other small grains. 26 Over recent years, much effort has been directed at the search for new  antifungal 27 materials from natural sources, and many antimicrobial compounds coming from plants 28 have been identified. Although the essential oils and their components have been 29 recommended as fumigants for preservation of food commodities, little is known about30 the molecular properties related to the antifungal activity. In the present study, we 31 performed a QSAR study for the inhibition of Fusarium verticillioides growth by ten 32 natural phenolic compounds, which could serve as a guide for the rational design of 33 further inhibitors. The results of the experimental determinations demonstrated that in 34 terms of the antifungal activity of natural phenolic compounds on F. Verticillioides, the 35 following order was found: carvacrol > thymol > isoeugenol > eugenol > vanillin > 36 creosol > m-cresol> o-cresol, p-cresol, and guaiacol. Mathematical models based on 37 molecular properties, Lipophilicity, Molar refractivity and Saturated area were found to 38 be the descriptors that best explained the antifungal activity of these compounds. These 39 models could be used in future to predict the activity of new compounds and to guide 40 the search for the synthesis of phenolic compounds with the capacity to alter F. 41 verticillioides growth.
Fil: Dambolena, José Sebastián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: López, Abel Gerardo. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina
Fil: Meriles, Jose Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Rubinstein, Héctor Ramón. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
description Fusarium is a ubiquitous hyalohyphomycete fungus usually isolated from food, which is 23 widespread in different environments (plant, grain, soil) and present at all latitudes. This 24 genus has been widely studied due to its ability to infect, cause tissue destruction and 25 produce mycotoxins on important crops such as corn, wheat and other small grains. 26 Over recent years, much effort has been directed at the search for new  antifungal 27 materials from natural sources, and many antimicrobial compounds coming from plants 28 have been identified. Although the essential oils and their components have been 29 recommended as fumigants for preservation of food commodities, little is known about30 the molecular properties related to the antifungal activity. In the present study, we 31 performed a QSAR study for the inhibition of Fusarium verticillioides growth by ten 32 natural phenolic compounds, which could serve as a guide for the rational design of 33 further inhibitors. The results of the experimental determinations demonstrated that in 34 terms of the antifungal activity of natural phenolic compounds on F. Verticillioides, the 35 following order was found: carvacrol > thymol > isoeugenol > eugenol > vanillin > 36 creosol > m-cresol> o-cresol, p-cresol, and guaiacol. Mathematical models based on 37 molecular properties, Lipophilicity, Molar refractivity and Saturated area were found to 38 be the descriptors that best explained the antifungal activity of these compounds. These 39 models could be used in future to predict the activity of new compounds and to guide 40 the search for the synthesis of phenolic compounds with the capacity to alter F. 41 verticillioides growth.
publishDate 2012
dc.date.none.fl_str_mv 2012-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/272309
Dambolena, José Sebastián; López, Abel Gerardo; Meriles, Jose Manuel; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto; Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study; Elsevier; Food Control; 28; 1; 11-2012; 163-170
0956-7135
CONICET Digital
CONICET
url http://hdl.handle.net/11336/272309
identifier_str_mv Dambolena, José Sebastián; López, Abel Gerardo; Meriles, Jose Manuel; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto; Inhibitory effect of 10 natural phenolic compounds on Fusarium verticillioides. A structure–property–activity relationship study; Elsevier; Food Control; 28; 1; 11-2012; 163-170
0956-7135
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
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info:eu-repo/semantics/altIdentifier/doi/10.1016/j.foodcont.2012.05.008
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dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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