Nicole Cortez, Victor Marin, Veronica A. Jimenez, Victor Silva, Oscar Leyton, Jaime R. Cabrera-Pardo, Bernd Schmidt, Matthias Heydenreich, Viviana Burgos, Paola Duran, Cristian Paz
- 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 analyzedFungal 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.…
MetadatenAuthor details: | Nicole Cortez, Victor Marin, Veronica A. Jimenez, Victor Silva, Oscar Leyton, Jaime R. Cabrera-PardoORCiD, Bernd SchmidtORCiDGND, Matthias HeydenreichORCiDGND, Viviana Burgos, Paola DuranORCiD, Cristian Paz |
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DOI: | https://doi.org/10.3390/ijms232112995 |
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ISSN: | 1422-0067 |
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Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/36361785 |
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Title of parent work (English): | International journal of molecular sciences |
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Publisher: | MDPI |
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Place of publishing: | Basel |
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Publication type: | Article |
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Language: | English |
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Date of first publication: | 2022/10/27 |
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Publication year: | 2022 |
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Release date: | 2024/09/16 |
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Tag: | Candida yeast; Cladosporium antarcticum; Drimys winteri; biocontrol; biotransformation; drimendiol; epidrimendiol; lanosterol 14 alpha-demethylase |
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Volume: | 23 |
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Issue: | 21 |
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Article number: | 12995 |
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Number of pages: | 12 |
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Funding institution: | Chilean Institute INACH [RT33-18]; ANID Chile [Fondecyt 1220831];; CONICYT/Chile [Fondequip EQM160054 2016] |
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Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
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DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
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Peer review: | Referiert |
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Publishing method: | Open Access / Gold Open-Access |
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| DOAJ gelistet |
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License (German): | CC-BY - Namensnennung 4.0 International |
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