Structural requirements for the antifungal activities of natural drimane sesquiterpenes and analogues, supported by conformational and electronic studies

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dc.citation.titleMolecules
dc.citation.volume18
dc.contributor.orcidhttps://orcid.org/0000-0002-7112-5500
dc.creatorDerita, Marcos Gabriel
dc.creatorMontenegro, Iván
dc.creatorGaribotto, Francisco
dc.creatorEnriz, Ricardo Daniel
dc.creatorCuellar Fritis, Mauricio
dc.creatorZacchino, Susana
dc.date.accessioned2024-10-24T14:03:06Z
dc.date.available2024-10-24T14:03:06Z
dc.date.issued2013-02-05
dc.description.abstractSeventeen 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.
dc.description.filFil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Farmacognosia; Argentina.
dc.description.filFil: Montenegro, Iván. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos naturales; Chile.
dc.description.filFil: Garibotto, Francisco. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina.
dc.description.filFil: Garibotto, Francisco. Universidad Nacional de San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis (IMIBIO-SL - CONICET); Argentina.
dc.description.filFil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina.
dc.description.filFil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis (IMIBIO-SL - CONICET); Argentina.
dc.description.filFil: Cuellar Fritis, Mauricio. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos naturales; Chile.
dc.description.filFil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Farmacognosia; Argentina.
dc.description.sponsorshipAgencia Nacional de Promoción de la Investigación, el Desarrollo Tecnológico y la Innovación (Agencia I+D+i): PICT-2010 0608, PICT 2010-1832
dc.description.sponsorshipUniversidad Nacional de Rosario (UNR): BIO 258
dc.description.sponsorshipUniversidad Nacional de San Luis (UNSL)
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET)
dc.description.versionpeerreviewed
dc.format.extent1-23
dc.identifier.issn1420-3049
dc.identifier.urihttps://hdl.handle.net/2133/27975
dc.language.isoen
dc.publisherMDPI
dc.relation.publisherversionhttps://doi.org/10.3390/molecules18022029
dc.relation.publisherversionhttps://www.mdpi.com/1420-3049/18/2/2029
dc.rightsopenAccess
dc.rights.holderDerita, Marcos Gabriel
dc.rights.holderMontenegro, Iván
dc.rights.holderGaribotto, Francisco
dc.rights.holderEnriz, Ricardo Daniel
dc.rights.holderCuellar Fritis, Mauricio
dc.rights.holderZacchino, Susana
dc.rights.holderUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas
dc.rights.textAttribution 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectAntifungal agents
dc.subjectDrimanes
dc.subjectStructure-activity relationships
dc.subjectStereo-electronic studies
dc.titleStructural requirements for the antifungal activities of natural drimane sesquiterpenes and analogues, supported by conformational and electronic studies
dc.typearticulo
dc.type.collectionarticulo
dc.type.versionpublishedVersion

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