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
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
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