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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ftmdpi:oai:mdpi.com:/1422-0067/23/21/12995/ 2023-08-20T04:02:19+02:00 Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum Nicole Cortez Víctor Marín Verónica A. Jiménez Víctor Silva Oscar Leyton Jaime R. Cabrera-Pardo Bernd Schmidt Matthias Heydenreich Viviana Burgos Paola Duran Cristian Paz agris 2022-10-27 application/pdf https://doi.org/10.3390/ijms232112995 EN eng Multidisciplinary Digital Publishing Institute Molecular Microbiology https://dx.doi.org/10.3390/ijms232112995 https://creativecommons.org/licenses/by/4.0/ International Journal of Molecular Sciences; Volume 23; Issue 21; Pages: 12995 Drimys winteri Cladosporium antarcticum drimendiol epidrimendiol biotransformation Candida yeast lanosterol 14α-demethylase biocontrol Text 2022 ftmdpi https://doi.org/10.3390/ijms232112995 2023-08-01T07:03:39Z 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 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 MDPI Open Access Publishing International Journal of Molecular Sciences 23 21 12995 |
institution |
Open Polar |
collection |
MDPI Open Access Publishing |
op_collection_id |
ftmdpi |
language |
English |
topic |
Drimys winteri Cladosporium antarcticum drimendiol epidrimendiol biotransformation Candida yeast lanosterol 14α-demethylase biocontrol |
spellingShingle |
Drimys winteri Cladosporium antarcticum drimendiol epidrimendiol biotransformation Candida yeast lanosterol 14α-demethylase biocontrol Nicole Cortez Víctor Marín Verónica A. Jiménez Víctor Silva Oscar Leyton Jaime R. Cabrera-Pardo Bernd Schmidt Matthias Heydenreich Viviana Burgos Paola Duran Cristian Paz Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum |
topic_facet |
Drimys winteri Cladosporium antarcticum drimendiol epidrimendiol biotransformation Candida yeast lanosterol 14α-demethylase biocontrol |
description |
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 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 |
Nicole Cortez Víctor Marín Verónica A. Jiménez Víctor Silva Oscar Leyton Jaime R. Cabrera-Pardo Bernd Schmidt Matthias Heydenreich Viviana Burgos Paola Duran Cristian Paz |
author_facet |
Nicole Cortez Víctor Marín Verónica A. Jiménez Víctor Silva Oscar Leyton Jaime R. Cabrera-Pardo Bernd Schmidt Matthias Heydenreich Viviana Burgos Paola Duran Cristian Paz |
author_sort |
Nicole Cortez |
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 |
Multidisciplinary Digital Publishing Institute |
publishDate |
2022 |
url |
https://doi.org/10.3390/ijms232112995 |
op_coverage |
agris |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
International Journal of Molecular Sciences; Volume 23; Issue 21; Pages: 12995 |
op_relation |
Molecular Microbiology https://dx.doi.org/10.3390/ijms232112995 |
op_rights |
https://creativecommons.org/licenses/by/4.0/ |
op_doi |
https://doi.org/10.3390/ijms232112995 |
container_title |
International Journal of Molecular Sciences |
container_volume |
23 |
container_issue |
21 |
container_start_page |
12995 |
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1774712727412932608 |