Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides

Autores
Dambolena, José Sebastián; López, Abel Gerardo; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Menthol is a naturally occurring cyclic terpene alcohol of plant origin from the Lamiaceae family. It has three chiral centres, implying eight possible different stereoisomers, which in turn define four pairs of enantiomers. This is the first work that reports on the stereoselective antifungal and antitoxigenic activities of the menthol stereoisomers on Fusarium verticillioides, with the (-)-menthol and (+)-menthol enantiomers found to be the most active inhibitors of fungal growth and sporulation. The results obtained suggest the importance of the presence of these substituents in the equatorial positions of menthol stereoisomers in the antifungal activity. The stereoisomer (-)-menthol, followed by (+)-menthol, were the most active compounds in the inhibition of fumonisin B1 (FB1) biosynthesis. The different antitoxigenic activities of (-)-menthol and (+)-menthol revealed that the molecular requirements to affect the FB1 production were dependent not only on the presence of the substituents in the equatorial positions, but also on their spatial arrangements.
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: 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
FUMONISIN B1
FUSARIUM VERTICILLIOIDES
MENTHOL
STEREOISOMERS
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:11336/85039
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/85039
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioidesDambolena, José SebastiánLópez, Abel GerardoRubinstein, Héctor RamónZygadlo, Julio AlbertoFUMONISIN B1FUSARIUM VERTICILLIOIDESMENTHOLSTEREOISOMERShttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Menthol is a naturally occurring cyclic terpene alcohol of plant origin from the Lamiaceae family. It has three chiral centres, implying eight possible different stereoisomers, which in turn define four pairs of enantiomers. This is the first work that reports on the stereoselective antifungal and antitoxigenic activities of the menthol stereoisomers on Fusarium verticillioides, with the (-)-menthol and (+)-menthol enantiomers found to be the most active inhibitors of fungal growth and sporulation. The results obtained suggest the importance of the presence of these substituents in the equatorial positions of menthol stereoisomers in the antifungal activity. The stereoisomer (-)-menthol, followed by (+)-menthol, were the most active compounds in the inhibition of fumonisin B1 (FB1) biosynthesis. The different antitoxigenic activities of (-)-menthol and (+)-menthol revealed that the molecular requirements to affect the FB1 production were dependent not only on the presence of the substituents in the equatorial positions, but also on their spatial arrangements.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: 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; ArgentinaElsevier2010-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/85039Dambolena, José Sebastián; López, Abel Gerardo; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto; Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides; Elsevier; Food Chemistry; 123; 1; 11-2010; 165-1700308-8146CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0308814610004802info:eu-repo/semantics/altIdentifier/doi/10.1016/j.foodchem.2010.04.024info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:35:17Zoai:ri.conicet.gov.ar:11336/85039instacron: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:34982025-09-29 09:35:17.876CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
title Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
spellingShingle Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
Dambolena, José Sebastián
FUMONISIN B1
FUSARIUM VERTICILLIOIDES
MENTHOL
STEREOISOMERS
title_short Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
title_full Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
title_fullStr Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
title_full_unstemmed Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
title_sort Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides
dc.creator.none.fl_str_mv Dambolena, José Sebastián
López, Abel Gerardo
Rubinstein, Héctor Ramón
Zygadlo, Julio Alberto
author Dambolena, José Sebastián
author_facet Dambolena, José Sebastián
López, Abel Gerardo
Rubinstein, Héctor Ramón
Zygadlo, Julio Alberto
author_role author
author2 López, Abel Gerardo
Rubinstein, Héctor Ramón
Zygadlo, Julio Alberto
author2_role author
author
author
dc.subject.none.fl_str_mv FUMONISIN B1
FUSARIUM VERTICILLIOIDES
MENTHOL
STEREOISOMERS
topic FUMONISIN B1
FUSARIUM VERTICILLIOIDES
MENTHOL
STEREOISOMERS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Menthol is a naturally occurring cyclic terpene alcohol of plant origin from the Lamiaceae family. It has three chiral centres, implying eight possible different stereoisomers, which in turn define four pairs of enantiomers. This is the first work that reports on the stereoselective antifungal and antitoxigenic activities of the menthol stereoisomers on Fusarium verticillioides, with the (-)-menthol and (+)-menthol enantiomers found to be the most active inhibitors of fungal growth and sporulation. The results obtained suggest the importance of the presence of these substituents in the equatorial positions of menthol stereoisomers in the antifungal activity. The stereoisomer (-)-menthol, followed by (+)-menthol, were the most active compounds in the inhibition of fumonisin B1 (FB1) biosynthesis. The different antitoxigenic activities of (-)-menthol and (+)-menthol revealed that the molecular requirements to affect the FB1 production were dependent not only on the presence of the substituents in the equatorial positions, but also on their spatial arrangements.
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: 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 Menthol is a naturally occurring cyclic terpene alcohol of plant origin from the Lamiaceae family. It has three chiral centres, implying eight possible different stereoisomers, which in turn define four pairs of enantiomers. This is the first work that reports on the stereoselective antifungal and antitoxigenic activities of the menthol stereoisomers on Fusarium verticillioides, with the (-)-menthol and (+)-menthol enantiomers found to be the most active inhibitors of fungal growth and sporulation. The results obtained suggest the importance of the presence of these substituents in the equatorial positions of menthol stereoisomers in the antifungal activity. The stereoisomer (-)-menthol, followed by (+)-menthol, were the most active compounds in the inhibition of fumonisin B1 (FB1) biosynthesis. The different antitoxigenic activities of (-)-menthol and (+)-menthol revealed that the molecular requirements to affect the FB1 production were dependent not only on the presence of the substituents in the equatorial positions, but also on their spatial arrangements.
publishDate 2010
dc.date.none.fl_str_mv 2010-11
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/11336/85039
Dambolena, José Sebastián; López, Abel Gerardo; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto; Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides; Elsevier; Food Chemistry; 123; 1; 11-2010; 165-170
0308-8146
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85039
identifier_str_mv Dambolena, José Sebastián; López, Abel Gerardo; Rubinstein, Héctor Ramón; Zygadlo, Julio Alberto; Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides; Elsevier; Food Chemistry; 123; 1; 11-2010; 165-170
0308-8146
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0308814610004802
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.foodchem.2010.04.024
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
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 13.070432

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