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First total synthesis of chromanone A, preparation of related compounds and evaluation of their antifungal activity against Candida albicans, a biofilm forming agent

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dc.citation.titleRSC Advances
dc.citation.volume19587-19597
dc.citation.volume11
dc.contributor.orcidhttps://orcid.org/0000-0002-8069-2793
dc.contributor.orcidhttps://orcid.org/0000-0002-6574-1702
dc.contributor.orcidhttps://orcid.org/0000-0003-3173-2178
dc.contributor.orcidhttps://orcid.org/0000-0002-4271-1690
dc.contributor.orcidhttps://orcid.org/0000-0002-1023-1641
dc.contributor.orcidhttps://orcid.org/0000-0003-2647-475X
dc.creatorCortés, Iván
dc.creatorCordisco, Estefanía
dc.creatorKaufman, Teodoro Saúl
dc.creatorSortino, Maximiliano Andrés
dc.creatorSvetaz, Laura Andrea
dc.creatorBracca, Andrea Beatriz Juana
dc.date.accessioned2024-04-18T18:52:21Z
dc.date.available2024-04-18T18:52:21Z
dc.date.issued2021-06-01
dc.description.abstractA straightforward and convenient approach for the first total syntheses of chromanone A and a related 7-OMe substituted natural product is reported. These unique C-3 substituted 2-hydroxymethyl chromones were recently isolated as fungal metabolites. Chromanone A was synthesized in 25.3% overall yield from the readily available pyrocatechol, whereas the second natural product was prepared in 39.7% global yield. A small library of chromones, including both natural products and some of their synthetic heterocyclic precursors, was evaluated against Candida albicans ATCC 10231, a biofilm forming agent. It was found that 8-methoxy-3-methyl-4-oxo-4H-chromene-2-carbaldehyde, a partially oxidized form of chromanone A, exhibited a minimum inhibitory concentration of 7.8 μg mL−1 and significantly inhibited the yeast's virulence factors, including the adherence to buccal epithelial cells and the secretion of phospholipases, as well as the formation of germ tubes and the generation of the hyphal pseudomycelium. In addition, despite the heterocycle exhibiting non-significant inhibition of the formation of the Candida biofilm, it completely inhibited the growth of C. albicans in preformed biofilms at 62.5 μg mL−1.
dc.description.filFil: Cortés, Iván. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Rosario (CONICET-IQUIR); Argentina.
dc.description.filFil: Cordisco, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina
dc.description.filFil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Rosario (CONICET-IQUIR); Argentina.
dc.description.filFil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina
dc.description.filFil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina
dc.description.filFil: Bracca, Andrea Beatriz Juana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Rosario (CONICET-IQUIR); Argentina.
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológica (ANPCyT): PICT 2017-0149, PICT 2016-1833
dc.identifier.issn2046-2069
dc.identifier.urihttps://hdl.handle.net/2133/26908
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlelanding/2021/ra/d1ra02553h
dc.relation.publisherversionhttps://doi.org/10.1039/d1ra02553h
dc.rightsopenAccess
dc.rights.holderCortés, Iván
dc.rights.holderCordisco, Estefanía
dc.rights.holderKaufman, Teodoro Saúl
dc.rights.holderSortino, Maximiliano Andrés
dc.rights.holderSvetaz, Laura Andrea
dc.rights.holderBracca, Andrea Beatriz Juana
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.subjectTotal synthesis
dc.subjectChromanone a
dc.subjectCandida albicans
dc.subjectBiofilms
dc.titleFirst total synthesis of chromanone A, preparation of related compounds and evaluation of their antifungal activity against Candida albicans, a biofilm forming agent
dc.typearticulo
dc.type.collectionarticulo
dc.type.versionpublishedVersion

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