Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum
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 G...
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ftpubmed:oai:pubmedcentral.nih.gov:9653998 2023-05-15T14:04:15+02:00 Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum Cortez, Nicole Marín, Víctor Jiménez, Verónica A. Silva, Víctor Leyton, Oscar Cabrera-Pardo, Jaime R. Schmidt, Bernd Heydenreich, Matthias Burgos, Viviana Duran, Paola Paz, Cristian 2022-10-27 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9653998/ http://www.ncbi.nlm.nih.gov/pubmed/36361785 https://doi.org/10.3390/ijms232112995 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9653998/ http://www.ncbi.nlm.nih.gov/pubmed/36361785 http://dx.doi.org/10.3390/ijms232112995 © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). CC-BY Int J Mol Sci Article Text 2022 ftpubmed https://doi.org/10.3390/ijms232112995 2022-11-20T02:25:41Z 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 NaBH(4) in methanol. Cladosporium antarcticum produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (1, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (2, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-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 µg/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 14α-demethylase, affecting the ergosterol synthesis. Text Antarc* Antarctica PubMed Central (PMC) International Journal of Molecular Sciences 23 21 12995 |
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Article Cortez, Nicole Marín, Víctor Jiménez, Verónica A. Silva, Víctor Leyton, Oscar Cabrera-Pardo, Jaime R. Schmidt, Bernd Heydenreich, Matthias Burgos, Viviana Duran, Paola Paz, Cristian Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum |
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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 NaBH(4) in methanol. Cladosporium antarcticum produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (1, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (2, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-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 µg/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 14α-demethylase, affecting the ergosterol synthesis. |
format |
Text |
author |
Cortez, Nicole Marín, Víctor Jiménez, Verónica A. Silva, Víctor Leyton, Oscar Cabrera-Pardo, Jaime R. Schmidt, Bernd Heydenreich, Matthias Burgos, Viviana Duran, Paola Paz, Cristian |
author_facet |
Cortez, Nicole Marín, Víctor Jiménez, Verónica A. Silva, Víctor Leyton, Oscar Cabrera-Pardo, Jaime R. Schmidt, Bernd Heydenreich, Matthias Burgos, Viviana Duran, Paola Paz, Cristian |
author_sort |
Cortez, Nicole |
title |
Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum |
title_short |
Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum |
title_full |
Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum |
title_fullStr |
Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum |
title_full_unstemmed |
Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum |
title_sort |
drimane sesquiterpene alcohols with activity against candida yeast obtained by biotransformation with cladosporium antarcticum |
publisher |
MDPI |
publishDate |
2022 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9653998/ http://www.ncbi.nlm.nih.gov/pubmed/36361785 https://doi.org/10.3390/ijms232112995 |
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Antarc* Antarctica |
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Antarc* Antarctica |
op_source |
Int J Mol Sci |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9653998/ http://www.ncbi.nlm.nih.gov/pubmed/36361785 http://dx.doi.org/10.3390/ijms232112995 |
op_rights |
© 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
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CC-BY |
op_doi |
https://doi.org/10.3390/ijms232112995 |
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International Journal of Molecular Sciences |
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23 |
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21 |
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12995 |
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1766275271769456640 |