In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis

Autores
Gallucci, Mauro Nicolas; Carezzano, Maria Evangelina; Oliva, Maria de Las Mercedes; Demo, Mirta Susana; Pizzolitto, Romina Paola; Zunino, María Paula; Zygadlo, Julio Alberto; Dambolena, José Sebastián
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Aims: To evaluate the antifungal activity and to analyse the structure–activity relationship of eleven natural phenolic compounds against four Candida species which are resistant to fluconazole. Methods and Results: Four different species of Candida isolates were used: Candida albicans, Candida krusei, Candida tropicalis and Candida dubliniensis. The phenolic compound carvacrol showed the highest anti-Candida bioactivity, followed by thymol and isoeugenol. The obtained minimum inhibitory concentration (MIC) values obtained were used in a quantitative structure– activity relationship (QSAR) analysis where the electronic, steric, thermodynamic and topological descriptors served as dependent variables. According to the descriptors obtained in this QSAR study, the antifungal activity of phenols has a first action specific character which is based on their interaction with plasma or mitochondrial membranes. The second action is based on a steric descriptor— the maximal and minimal projection of the area—which could explain the inability of some phenolic compounds to be biotransformed to quinones methylene by Candida species. Conclusions: According to the descriptors obtained in this QSAR study, the anti-Candida activity of ortho-substituted phenols is due to more than one action mechanism. The anti-Candida activity of phenolic compounds can be predicted by their molecular properties and structural characteristics. Significance and Impact of the Study: These results could be employed to predict the anti-Candida activity of new phenolic compounds in the search for new alternatives or complementary therapies to combat against candidiasis.
Fil: Gallucci, Mauro Nicolas. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Carezzano, Maria Evangelina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Oliva, Maria de Las Mercedes. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Demo, Mirta Susana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina
Fil: Pizzolitto, Romina Paola. 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: Zunino, María Paula. 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: 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
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
Materia
Natural Phenols
Anti-Candidal Activity
Qsar
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:11336/22119
Acceder
id CONICETDig_898a71fcf0f3c1914ac611a52a35576a
oai_identifier_str oai:ri.conicet.gov.ar:11336/22119
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysisGallucci, Mauro NicolasCarezzano, Maria EvangelinaOliva, Maria de Las MercedesDemo, Mirta SusanaPizzolitto, Romina PaolaZunino, María PaulaZygadlo, Julio AlbertoDambolena, José SebastiánNatural PhenolsAnti-Candidal ActivityQsarhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Aims: To evaluate the antifungal activity and to analyse the structure–activity relationship of eleven natural phenolic compounds against four Candida species which are resistant to fluconazole. Methods and Results: Four different species of Candida isolates were used: Candida albicans, Candida krusei, Candida tropicalis and Candida dubliniensis. The phenolic compound carvacrol showed the highest anti-Candida bioactivity, followed by thymol and isoeugenol. The obtained minimum inhibitory concentration (MIC) values obtained were used in a quantitative structure– activity relationship (QSAR) analysis where the electronic, steric, thermodynamic and topological descriptors served as dependent variables. According to the descriptors obtained in this QSAR study, the antifungal activity of phenols has a first action specific character which is based on their interaction with plasma or mitochondrial membranes. The second action is based on a steric descriptor— the maximal and minimal projection of the area—which could explain the inability of some phenolic compounds to be biotransformed to quinones methylene by Candida species. Conclusions: According to the descriptors obtained in this QSAR study, the anti-Candida activity of ortho-substituted phenols is due to more than one action mechanism. The anti-Candida activity of phenolic compounds can be predicted by their molecular properties and structural characteristics. Significance and Impact of the Study: These results could be employed to predict the anti-Candida activity of new phenolic compounds in the search for new alternatives or complementary therapies to combat against candidiasis.Fil: Gallucci, Mauro Nicolas. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Carezzano, Maria Evangelina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Oliva, Maria de Las Mercedes. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Demo, Mirta Susana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; ArgentinaFil: Pizzolitto, Romina Paola. 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: Zunino, María Paula. 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: 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; ArgentinaFil: 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; ArgentinaWiley2014-01info: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/pdfhttp://hdl.handle.net/11336/22119Gallucci, Mauro Nicolas; Carezzano, Maria Evangelina; Oliva, Maria de Las Mercedes; Demo, Mirta Susana; Pizzolitto, Romina Paola; et al.; In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis; Wiley; Journal of Applied Microbiology; 116; 4; 1-2014; 795-8041364-5072CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1111/jam.12432info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1111/jam.12432/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:36:23Zoai:ri.conicet.gov.ar:11336/22119instacron: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 09:36:23.381CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
title In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
spellingShingle In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
Gallucci, Mauro Nicolas
Natural Phenols
Anti-Candidal Activity
Qsar
title_short In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
title_full In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
title_fullStr In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
title_full_unstemmed In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
title_sort In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis
dc.creator.none.fl_str_mv Gallucci, Mauro Nicolas
Carezzano, Maria Evangelina
Oliva, Maria de Las Mercedes
Demo, Mirta Susana
Pizzolitto, Romina Paola
Zunino, María Paula
Zygadlo, Julio Alberto
Dambolena, José Sebastián
author Gallucci, Mauro Nicolas
author_facet Gallucci, Mauro Nicolas
Carezzano, Maria Evangelina
Oliva, Maria de Las Mercedes
Demo, Mirta Susana
Pizzolitto, Romina Paola
Zunino, María Paula
Zygadlo, Julio Alberto
Dambolena, José Sebastián
author_role author
author2 Carezzano, Maria Evangelina
Oliva, Maria de Las Mercedes
Demo, Mirta Susana
Pizzolitto, Romina Paola
Zunino, María Paula
Zygadlo, Julio Alberto
Dambolena, José Sebastián
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Natural Phenols
Anti-Candidal Activity
Qsar
topic Natural Phenols
Anti-Candidal Activity
Qsar
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Aims: To evaluate the antifungal activity and to analyse the structure–activity relationship of eleven natural phenolic compounds against four Candida species which are resistant to fluconazole. Methods and Results: Four different species of Candida isolates were used: Candida albicans, Candida krusei, Candida tropicalis and Candida dubliniensis. The phenolic compound carvacrol showed the highest anti-Candida bioactivity, followed by thymol and isoeugenol. The obtained minimum inhibitory concentration (MIC) values obtained were used in a quantitative structure– activity relationship (QSAR) analysis where the electronic, steric, thermodynamic and topological descriptors served as dependent variables. According to the descriptors obtained in this QSAR study, the antifungal activity of phenols has a first action specific character which is based on their interaction with plasma or mitochondrial membranes. The second action is based on a steric descriptor— the maximal and minimal projection of the area—which could explain the inability of some phenolic compounds to be biotransformed to quinones methylene by Candida species. Conclusions: According to the descriptors obtained in this QSAR study, the anti-Candida activity of ortho-substituted phenols is due to more than one action mechanism. The anti-Candida activity of phenolic compounds can be predicted by their molecular properties and structural characteristics. Significance and Impact of the Study: These results could be employed to predict the anti-Candida activity of new phenolic compounds in the search for new alternatives or complementary therapies to combat against candidiasis.
Fil: Gallucci, Mauro Nicolas. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Carezzano, Maria Evangelina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Oliva, Maria de Las Mercedes. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Demo, Mirta Susana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas, Fisicoquímicas y Naturales. Departamento de Microbiología e Inmunología; Argentina
Fil: Pizzolitto, Romina Paola. 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: Zunino, María Paula. 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: 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
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
description Aims: To evaluate the antifungal activity and to analyse the structure–activity relationship of eleven natural phenolic compounds against four Candida species which are resistant to fluconazole. Methods and Results: Four different species of Candida isolates were used: Candida albicans, Candida krusei, Candida tropicalis and Candida dubliniensis. The phenolic compound carvacrol showed the highest anti-Candida bioactivity, followed by thymol and isoeugenol. The obtained minimum inhibitory concentration (MIC) values obtained were used in a quantitative structure– activity relationship (QSAR) analysis where the electronic, steric, thermodynamic and topological descriptors served as dependent variables. According to the descriptors obtained in this QSAR study, the antifungal activity of phenols has a first action specific character which is based on their interaction with plasma or mitochondrial membranes. The second action is based on a steric descriptor— the maximal and minimal projection of the area—which could explain the inability of some phenolic compounds to be biotransformed to quinones methylene by Candida species. Conclusions: According to the descriptors obtained in this QSAR study, the anti-Candida activity of ortho-substituted phenols is due to more than one action mechanism. The anti-Candida activity of phenolic compounds can be predicted by their molecular properties and structural characteristics. Significance and Impact of the Study: These results could be employed to predict the anti-Candida activity of new phenolic compounds in the search for new alternatives or complementary therapies to combat against candidiasis.
publishDate 2014
dc.date.none.fl_str_mv 2014-01
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/11336/22119
Gallucci, Mauro Nicolas; Carezzano, Maria Evangelina; Oliva, Maria de Las Mercedes; Demo, Mirta Susana; Pizzolitto, Romina Paola; et al.; In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis; Wiley; Journal of Applied Microbiology; 116; 4; 1-2014; 795-804
1364-5072
CONICET Digital
CONICET
url http://hdl.handle.net/11336/22119
identifier_str_mv Gallucci, Mauro Nicolas; Carezzano, Maria Evangelina; Oliva, Maria de Las Mercedes; Demo, Mirta Susana; Pizzolitto, Romina Paola; et al.; In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis; Wiley; Journal of Applied Microbiology; 116; 4; 1-2014; 795-804
1364-5072
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1111/jam.12432
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1111/jam.12432/abstract
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
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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
_version_ 1844613140912799744
score 13.069144

Publicaciones similares