Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study

Autores
Dambolena, Jose Sebastian; Zygadlo, Julio Alberto; Rubinstein, Héctor
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Fumonisin B1 (FB1) is a Fusarium mycotoxin that has received considerable attention from food regulatory agencies, since it shows immunotoxic, neurotoxic, hepatotoxic, nephrotoxic and carcinogenic properties in animals. Although several publications have reported that some natural phenolic compounds can cause a reduction in mycotoxin production, little is known about the molecular properties related to their antitoxigenic activities. The objective of this work was to evaluate which of these molecular properties are important in antifumonisin activity, with this being the first structure?activity relationship study concerning the antimyctoxigenic activity of natural phenolic compounds. The results of the experimental determination of the FB1 inhibition capacity for ten natural phenolic compounds revealed thymol, carvacrol, and isoeugenol followed by eugenol to be the most active antifumonisin compounds. Lipophilicity, molar refractivity and saturated area were demonstrated to be the molecular properties or descriptors which best explained the antifumonisin activity of these phenolic compounds. A mathematical expression, obtained by QSAR analysis, was able to predict the antifumonisin activity of other structurally related molecules. These findings could provide an important contribution in the search for new compounds with antifumonisin activity.
Fil: Dambolena, Jose Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Rubinstein, Héctor. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Bioquímica Clínica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
Materia
Fumonisin B1
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
OAI Identificador
oai:ri.conicet.gov.ar:11336/13146
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship studyDambolena, Jose SebastianZygadlo, Julio AlbertoRubinstein, HéctorFumonisin B1Natural Phenolic CompoundsQsarLipophilicityMolar RefractivitySaturated Areahttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Fumonisin B1 (FB1) is a Fusarium mycotoxin that has received considerable attention from food regulatory agencies, since it shows immunotoxic, neurotoxic, hepatotoxic, nephrotoxic and carcinogenic properties in animals. Although several publications have reported that some natural phenolic compounds can cause a reduction in mycotoxin production, little is known about the molecular properties related to their antitoxigenic activities. The objective of this work was to evaluate which of these molecular properties are important in antifumonisin activity, with this being the first structure?activity relationship study concerning the antimyctoxigenic activity of natural phenolic compounds. The results of the experimental determination of the FB1 inhibition capacity for ten natural phenolic compounds revealed thymol, carvacrol, and isoeugenol followed by eugenol to be the most active antifumonisin compounds. Lipophilicity, molar refractivity and saturated area were demonstrated to be the molecular properties or descriptors which best explained the antifumonisin activity of these phenolic compounds. A mathematical expression, obtained by QSAR analysis, was able to predict the antifumonisin activity of other structurally related molecules. These findings could provide an important contribution in the search for new compounds with antifumonisin activity.Fil: Dambolena, Jose Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Rubinstein, Héctor. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Bioquímica Clínica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; ArgentinaElsevier Science2011-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/13146Dambolena, Jose Sebastian; Zygadlo, Julio Alberto; Rubinstein, Héctor; Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study; Elsevier Science; International Journal Of Food Microbiology; 145; 1; 1-2011; 140-1460168-1605enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0168160510006732info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ijfoodmicro.2010.12.001info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-17T11:34:31Zoai:ri.conicet.gov.ar:11336/13146instacron: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:34982025-09-17 11:34:31.983CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
title Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
spellingShingle Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
Dambolena, Jose Sebastian
Fumonisin B1
Natural Phenolic Compounds
Qsar
Lipophilicity
Molar Refractivity
Saturated Area
title_short Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
title_full Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
title_fullStr Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
title_full_unstemmed Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
title_sort Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study
dc.creator.none.fl_str_mv Dambolena, Jose Sebastian
Zygadlo, Julio Alberto
Rubinstein, Héctor
author Dambolena, Jose Sebastian
author_facet Dambolena, Jose Sebastian
Zygadlo, Julio Alberto
Rubinstein, Héctor
author_role author
author2 Zygadlo, Julio Alberto
Rubinstein, Héctor
author2_role author
author
dc.subject.none.fl_str_mv Fumonisin B1
Natural Phenolic Compounds
Qsar
Lipophilicity
Molar Refractivity
Saturated Area
topic Fumonisin B1
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 Fumonisin B1 (FB1) is a Fusarium mycotoxin that has received considerable attention from food regulatory agencies, since it shows immunotoxic, neurotoxic, hepatotoxic, nephrotoxic and carcinogenic properties in animals. Although several publications have reported that some natural phenolic compounds can cause a reduction in mycotoxin production, little is known about the molecular properties related to their antitoxigenic activities. The objective of this work was to evaluate which of these molecular properties are important in antifumonisin activity, with this being the first structure?activity relationship study concerning the antimyctoxigenic activity of natural phenolic compounds. The results of the experimental determination of the FB1 inhibition capacity for ten natural phenolic compounds revealed thymol, carvacrol, and isoeugenol followed by eugenol to be the most active antifumonisin compounds. Lipophilicity, molar refractivity and saturated area were demonstrated to be the molecular properties or descriptors which best explained the antifumonisin activity of these phenolic compounds. A mathematical expression, obtained by QSAR analysis, was able to predict the antifumonisin activity of other structurally related molecules. These findings could provide an important contribution in the search for new compounds with antifumonisin activity.
Fil: Dambolena, Jose Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Rubinstein, Héctor. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Bioquímica Clínica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Bioquímica Clínica e Inmunología; Argentina
description Fumonisin B1 (FB1) is a Fusarium mycotoxin that has received considerable attention from food regulatory agencies, since it shows immunotoxic, neurotoxic, hepatotoxic, nephrotoxic and carcinogenic properties in animals. Although several publications have reported that some natural phenolic compounds can cause a reduction in mycotoxin production, little is known about the molecular properties related to their antitoxigenic activities. The objective of this work was to evaluate which of these molecular properties are important in antifumonisin activity, with this being the first structure?activity relationship study concerning the antimyctoxigenic activity of natural phenolic compounds. The results of the experimental determination of the FB1 inhibition capacity for ten natural phenolic compounds revealed thymol, carvacrol, and isoeugenol followed by eugenol to be the most active antifumonisin compounds. Lipophilicity, molar refractivity and saturated area were demonstrated to be the molecular properties or descriptors which best explained the antifumonisin activity of these phenolic compounds. A mathematical expression, obtained by QSAR analysis, was able to predict the antifumonisin activity of other structurally related molecules. These findings could provide an important contribution in the search for new compounds with antifumonisin activity.
publishDate 2011
dc.date.none.fl_str_mv 2011-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/13146
Dambolena, Jose Sebastian; Zygadlo, Julio Alberto; Rubinstein, Héctor; Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study; Elsevier Science; International Journal Of Food Microbiology; 145; 1; 1-2011; 140-146
0168-1605
url http://hdl.handle.net/11336/13146
identifier_str_mv Dambolena, Jose Sebastian; Zygadlo, Julio Alberto; Rubinstein, Héctor; Antifumonisin activity of natural phenolic compounds: A structure–property–activity relationship study; Elsevier Science; International Journal Of Food Microbiology; 145; 1; 1-2011; 140-146
0168-1605
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0168160510006732
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ijfoodmicro.2010.12.001
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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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score 13.001348

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