Repositorio UFRO · Omeka S

Bromination of eudesmin isolated from araucaria araucana induces epimerization and give bromine derivatives with loss of anti-Candida activity

Primer Autor	Paz, Cristian
Co-autores	Bravo-Arrepol, Gaston Becerra, Jose Ortiz, Leandro Cabrera-Pardo, Jaime Schmidt, Bernd Heydenreich, Matthias Kelling, Alexandra Sperlich, Eric Karpinski, Tomasz M.
Título	Bromination of eudesmin isolated from araucaria araucana induces epimerization and give bromine derivatives with loss of anti-Candida activity
Editorial	TAYLOR & FRANCIS LTD
Revista	NATURAL PRODUCT RESEARCH
Lenguaje	en
Resumen	Furofuran lignanes show important biological activities for the treatment of infectious diseases, inflammatory and metabolic pathologies. They have been isolated from leaves and barks of many plants. In Chile the native conifer Araucaria araucana produces eudesmin, matairesinol, secoisolariciresinol and lariciresinol in stemwood, branchwood and knotwood. These compounds were previously isolated by laborious flash chromatography on silica gel. Here we report the easy isolation of eudesmin by soxhlet extraction from milled knots of Araucaria araucana with hexane, followed by cryo-crystallization at -20 degrees C. Upon bromination of the isolated eudesmin epimerization at one benzylic position occurs, giving epieudesmin and the corresponding mono and di-brominated derivatives. The structures were determined by 1D, 2D NMR and X-ray diffraction. The analysis of products against Candida yeast showed that eudesmin has a moderate activity against different strains of Candida from 62.5 to 500 mu g/mL. This activity decreases for epieudesmin, while bromine derivatives are not active.
Fecha Publicación	2023
Tipo de Recurso	artículo original
Derecho de Acceso	resgistro bibliográfico
doi	10.1080/14786419.2022.2089140
Formato Recurso	PDF
Palabras Claves	Eudesmin purification Eudesmin bromination X-ray diffraction anti-Candida activity
Ubicación del archivo	http://dx.doi.org/10.1080/14786419.2022.2089140
Categoría OCDE	Química Farmacología y Farmacia Química Orgánica Biología Molecular Biotecnología Relacionada con la Salud
Materias	Purificación de Eudesmina bromación de eudesmina Difracción de rayos X actividad anti-Candida
Ubicación geográfica	Araucanía, Chile
Página de inicio (Recomendado-único)	2466.0
Página final (Recomendado-único)	2471
Identificador del recurso (Mandatado-único)	artículo original
Versión del recurso (Recomendado-único)	versión publicada
Derechos de acceso	metadata
Access Rights	metadata
Id de Web of Science	WOS:000812052000001
ISSN	1478-6419
Tipo de ruta	hibrido
Categoría WOS	Química Farmacología y Farmacia
Referencia del Financiador (Mandatado si es aplicable-repetible)	ANID FONDECYT 11181076