Bromination of eudesmin isolated from araucaria araucana induces epimerization and give bromine derivatives with loss of anti-Candida activity
Primer Autor |
Paz, Cristian
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Co-autores |
Bravo-Arrepol, Gaston
Becerra, Jose
Ortiz, Leandro
Cabrera-Pardo, Jaime
Schmidt, Bernd
Heydenreich, Matthias
Kelling, Alexandra
Sperlich, Eric
Karpinski, Tomasz M.
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Título |
Bromination of eudesmin isolated from araucaria araucana induces epimerization and give bromine derivatives with loss of anti-Candida activity
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Editorial |
TAYLOR & FRANCIS LTD
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Revista |
NATURAL PRODUCT RESEARCH
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Lenguaje |
en
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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.
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Fecha Publicación |
2023
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Tipo de Recurso |
artículo original
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Derecho de Acceso |
resgistro bibliográfico
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doi |
10.1080/14786419.2022.2089140
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Formato Recurso |
PDF
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Palabras Claves |
Eudesmin purification
Eudesmin bromination
X-ray diffraction
anti-Candida activity
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Ubicación del archivo | |
Categoría OCDE |
Química
Farmacología y Farmacia
Química Orgánica
Biología Molecular
Biotecnología Relacionada con la Salud
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Materias |
Purificación de Eudesmina
bromación de eudesmina
Difracción de rayos X
actividad anti-Candida
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Ubicación geográfica |
Araucanía, Chile
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Página de inicio (Recomendado-único) |
2466.0
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Página final (Recomendado-único) |
2471
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Identificador del recurso (Mandatado-único) |
artículo original
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Versión del recurso (Recomendado-único) |
versión publicada
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Derechos de acceso |
metadata
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Access Rights |
metadata
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Id de Web of Science |
WOS:000812052000001
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ISSN |
1478-6419
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Tipo de ruta |
hibrido
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Categoría WOS |
Química
Farmacología y Farmacia
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Referencia del Financiador (Mandatado si es aplicable-repetible) |
ANID FONDECYT 11181076
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