Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

Autores
Derita, Marcos Gabriel; Montenegro, Ivan; Garibotto, Francisco Matías; Enriz, Ricardo Daniel; Cuellar Fritis, Mauricio; Zacchino, Susana Alicia Stella
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5?17 obtained from 1?3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.
Fil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.; Universidad Nacional del Litoral. Facultad de Ciencias Agrarias. Departamento de Producción Vegetal. Cátedra de Cultivos Intensivos; Argentina;
Fil: Montenegro, Ivan. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;
Fil: Garibotto, Francisco Matías. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - San Luis. Instituto Multidiciplinario de Investigación Biológica de San Luis; Argentina; Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia; Argentina;
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina.; Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico -CONICET - San Luis. Instituto Multidisciplinario de Investigación Biológica de San Luis; Argentina.;
Fil: Cuellar Fritis, Mauricio. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.;
Materia
Antifungal agents
Drimanes
Structure-activity relationships
Stereo-electronic studies
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:11336/1543
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/1543
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic StudiesDerita, Marcos GabrielMontenegro, IvanGaribotto, Francisco MatíasEnriz, Ricardo DanielCuellar Fritis, MauricioZacchino, Susana Alicia StellaAntifungal agentsDrimanesStructure-activity relationshipsStereo-electronic studieshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5?17 obtained from 1?3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.Fil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.; Universidad Nacional del Litoral. Facultad de Ciencias Agrarias. Departamento de Producción Vegetal. Cátedra de Cultivos Intensivos; Argentina;Fil: Montenegro, Ivan. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;Fil: Garibotto, Francisco Matías. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - San Luis. Instituto Multidiciplinario de Investigación Biológica de San Luis; Argentina; Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia; Argentina;Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina.; Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico -CONICET - San Luis. Instituto Multidisciplinario de Investigación Biológica de San Luis; Argentina.;Fil: Cuellar Fritis, Mauricio. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.;Molecular Diversity Preservation International2013-02-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/1543Derita, Marcos Gabriel; Montenegro, Ivan; Garibotto, Francisco Matías; Enriz, Ricardo Daniel; Cuellar Fritis, Mauricio; et al.; Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies; Molecular Diversity Preservation International; Molecules; 18; 5-2-2013; 2029-20511420-3049enginfo:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1420-3049/18/2/2029info:eu-repo/semantics/altIdentifier/doi/doi:10.3390/molecules18022029info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:12:10Zoai:ri.conicet.gov.ar:11336/1543instacron: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 10:12:11.075CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
title Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
spellingShingle Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
Derita, Marcos Gabriel
Antifungal agents
Drimanes
Structure-activity relationships
Stereo-electronic studies
title_short Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
title_full Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
title_fullStr Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
title_full_unstemmed Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
title_sort Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
dc.creator.none.fl_str_mv Derita, Marcos Gabriel
Montenegro, Ivan
Garibotto, Francisco Matías
Enriz, Ricardo Daniel
Cuellar Fritis, Mauricio
Zacchino, Susana Alicia Stella
author Derita, Marcos Gabriel
author_facet Derita, Marcos Gabriel
Montenegro, Ivan
Garibotto, Francisco Matías
Enriz, Ricardo Daniel
Cuellar Fritis, Mauricio
Zacchino, Susana Alicia Stella
author_role author
author2 Montenegro, Ivan
Garibotto, Francisco Matías
Enriz, Ricardo Daniel
Cuellar Fritis, Mauricio
Zacchino, Susana Alicia Stella
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Antifungal agents
Drimanes
Structure-activity relationships
Stereo-electronic studies
topic Antifungal agents
Drimanes
Structure-activity relationships
Stereo-electronic studies
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5?17 obtained from 1?3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.
Fil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.; Universidad Nacional del Litoral. Facultad de Ciencias Agrarias. Departamento de Producción Vegetal. Cátedra de Cultivos Intensivos; Argentina;
Fil: Montenegro, Ivan. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;
Fil: Garibotto, Francisco Matías. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - San Luis. Instituto Multidiciplinario de Investigación Biológica de San Luis; Argentina; Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia; Argentina;
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina.; Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico -CONICET - San Luis. Instituto Multidisciplinario de Investigación Biológica de San Luis; Argentina.;
Fil: Cuellar Fritis, Mauricio. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.;
description Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5?17 obtained from 1?3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.
publishDate 2013
dc.date.none.fl_str_mv 2013-02-05
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/11336/1543
Derita, Marcos Gabriel; Montenegro, Ivan; Garibotto, Francisco Matías; Enriz, Ricardo Daniel; Cuellar Fritis, Mauricio; et al.; Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies; Molecular Diversity Preservation International; Molecules; 18; 5-2-2013; 2029-2051
1420-3049
url http://hdl.handle.net/11336/1543
identifier_str_mv Derita, Marcos Gabriel; Montenegro, Ivan; Garibotto, Francisco Matías; Enriz, Ricardo Daniel; Cuellar Fritis, Mauricio; et al.; Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies; Molecular Diversity Preservation International; Molecules; 18; 5-2-2013; 2029-2051
1420-3049
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1420-3049/18/2/2029
info:eu-repo/semantics/altIdentifier/doi/doi:10.3390/molecules18022029
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 Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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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