Repositorio UFRO · Omeka S

Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum

Primer Autor	Paz, Cristian
Co-autores	Cortez, Nicole Marin, Victor Jimenez, Veronica A. Silva, Victor Leyton, Oscar Cabrera-Pardo, Jaime R. Schmidt, Bernd Heydenreich, Matthias Burgos, Viviana Duran, Paola
Título	Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum
Editorial	MDPI
Revista	INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
Lenguaje	en
Resumen	Fungal biotransformation is an attractive synthetic strategy to produce highly specific compounds with chemical functionality in regions of the carbon skeleton that are not easily activated by conventional organic chemistry methods. In this work, Cladosporium antarcticum isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against Candida yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH4 in methanol. Cladosporium antarcticum produced two major products from drimendiol, identified as 9 alpha-hydroxydrimendiol (1, 41.4 mg, 19.4% yield) and 3 beta-hydroxydrimendiol (2, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9 beta-hydroxyepidrimendiol (3, 86.6 mg, 41.6% yield). The products were purified by column chromatography and their structure elucidated by NMR and MS. The antifungal activity of compounds 1-3 was analyzed against Candida albicans, C. krusei and C. parapsilosis, showing that compound 2 has a MIC lower than 15 mu g/mL against the three-pathogenic yeast. In silico studies suggest that a possible mechanism of action for the novel compounds is the inhibition of the enzyme lanosterol 14 alpha-demethylase, affecting the ergosterol synthesis.
Tipo de Recurso	artículo original
Description	This research was funded by the Chilean Institute INACH with the grant RT33-18 and by ANID Chile under Fondecyt 1220831 granted to C.P. MALDI-TOF MS analyses were partially developed using an equipment funded by CONICYT/Chile through the project Fondequip EQM160054 2016. Esta investigación fue financiada por el Instituto Chileno INACH con la beca RT33-18 y por ANID Chile bajo el Fondecyt 1220831 otorgado a C.P. Los análisis MALDI-TOF MS se desarrollaron parcialmente utilizando un equipo financiado por CONICYT/Chile a través del proyecto Fondequip EQM160054 2016.
doi	10.3390/ijms232112995
Formato Recurso	PDF
Palabras Claves	Drimys winteri Cladosporium antarcticum drimendiol epidrimendiol biotransformation Candida yeast lanosterol 14 alpha-demethylase biocontrol ANTIFUNGAL DERIVATIVES MECHANISM EXTRACTS
Ubicación del archivo	http://dx.doi.org/10.3390/ijms232112995
Categoría OCDE	Bioquímica y Biología Molecular Química Multidisciplinar
Materias	Drimys winteri Cladosporium antarcticum drimendiol epidrimendiol biotransformación levadura Candida lanosterol 14 alfa-desmetilasa biocontrol ANTIFÚNGICOS DERIVADOS MECANISMO EXTRACTOS
Disciplinas de la OCDE	Biotecnología Relacionada con la Salud Química Orgánica Micología
Título de la cita (Recomendado-único)	Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum
Identificador del recurso (Mandatado-único)	artículo original
Versión del recurso (Recomendado-único)	version publicada
License	CC BY 4.0
Condición de la licencia (Recomendado-repetible)	CC BY 4.0
Derechos de acceso	acceso abierto
Access Rights	acceso abierto
Referencia del Financiador (Mandatado si es aplicable-repetible)	ANID-FONDECYT 1220831 ANID-FONDEQUIP EQM160054 ANID FONDECYT 1220831 ANID FONDEQUIP EQM160054
Id de Web of Science	WOS:000882640800001