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

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, <i<Cladosporium antarcticum</i< isolated...
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Gespeichert in:

Autor*in:	Nicole Cortez [verfasserIn] Víctor Marín [verfasserIn] Verónica A. Jiménez [verfasserIn] Víctor Silva [verfasserIn] Oscar Leyton [verfasserIn] Jaime R. Cabrera-Pardo [verfasserIn] Bernd Schmidt [verfasserIn] Matthias Heydenreich [verfasserIn] Viviana Burgos [verfasserIn] Paola Duran [verfasserIn] Cristian Paz [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	drimendiol epidrimendiol biotransformation

Übergeordnetes Werk:	In: International Journal of Molecular Sciences - MDPI AG, 2003, 23(2022), 21, p 12995
Übergeordnetes Werk:	volume:23 ; year:2022 ; number:21, p 12995

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc Journal toc

DOI / URN:	10.3390/ijms232112995

Katalog-ID:	DOAJ028693663

Internformat


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allfields	10.3390/ijms232112995 doi (DE-627)DOAJ028693663 (DE-599)DOAJe5f2377139654bd387b07920063ed5b5 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Nicole Cortez verfasserin aut Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i< 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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. <i<Drimys winteri</i< <i<Cladosporium antarcticum</i< drimendiol epidrimendiol biotransformation <i<Candida</i< yeast Biology (General) Chemistry Víctor Marín verfasserin aut Verónica A. Jiménez verfasserin aut Víctor Silva verfasserin aut Oscar Leyton verfasserin aut Jaime R. Cabrera-Pardo verfasserin aut Bernd Schmidt verfasserin aut Matthias Heydenreich verfasserin aut Viviana Burgos verfasserin aut Paola Duran verfasserin aut Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 21, p 12995 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:21, p 12995 https://doi.org/10.3390/ijms232112995 kostenfrei https://doaj.org/article/e5f2377139654bd387b07920063ed5b5 kostenfrei https://www.mdpi.com/1422-0067/23/21/12995 kostenfrei https://doaj.org/toc/1661-6596 Journal toc kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 23 2022 21, p 12995
spelling	10.3390/ijms232112995 doi (DE-627)DOAJ028693663 (DE-599)DOAJe5f2377139654bd387b07920063ed5b5 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Nicole Cortez verfasserin aut Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i< 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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. <i<Drimys winteri</i< <i<Cladosporium antarcticum</i< drimendiol epidrimendiol biotransformation <i<Candida</i< yeast Biology (General) Chemistry Víctor Marín verfasserin aut Verónica A. Jiménez verfasserin aut Víctor Silva verfasserin aut Oscar Leyton verfasserin aut Jaime R. Cabrera-Pardo verfasserin aut Bernd Schmidt verfasserin aut Matthias Heydenreich verfasserin aut Viviana Burgos verfasserin aut Paola Duran verfasserin aut Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 21, p 12995 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:21, p 12995 https://doi.org/10.3390/ijms232112995 kostenfrei https://doaj.org/article/e5f2377139654bd387b07920063ed5b5 kostenfrei https://www.mdpi.com/1422-0067/23/21/12995 kostenfrei https://doaj.org/toc/1661-6596 Journal toc kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 23 2022 21, p 12995
allfields_unstemmed	10.3390/ijms232112995 doi (DE-627)DOAJ028693663 (DE-599)DOAJe5f2377139654bd387b07920063ed5b5 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Nicole Cortez verfasserin aut Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i< 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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. <i<Drimys winteri</i< <i<Cladosporium antarcticum</i< drimendiol epidrimendiol biotransformation <i<Candida</i< yeast Biology (General) Chemistry Víctor Marín verfasserin aut Verónica A. Jiménez verfasserin aut Víctor Silva verfasserin aut Oscar Leyton verfasserin aut Jaime R. Cabrera-Pardo verfasserin aut Bernd Schmidt verfasserin aut Matthias Heydenreich verfasserin aut Viviana Burgos verfasserin aut Paola Duran verfasserin aut Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 21, p 12995 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:21, p 12995 https://doi.org/10.3390/ijms232112995 kostenfrei https://doaj.org/article/e5f2377139654bd387b07920063ed5b5 kostenfrei https://www.mdpi.com/1422-0067/23/21/12995 kostenfrei https://doaj.org/toc/1661-6596 Journal toc kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 23 2022 21, p 12995
allfieldsGer	10.3390/ijms232112995 doi (DE-627)DOAJ028693663 (DE-599)DOAJe5f2377139654bd387b07920063ed5b5 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Nicole Cortez verfasserin aut Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i< 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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. <i<Drimys winteri</i< <i<Cladosporium antarcticum</i< drimendiol epidrimendiol biotransformation <i<Candida</i< yeast Biology (General) Chemistry Víctor Marín verfasserin aut Verónica A. Jiménez verfasserin aut Víctor Silva verfasserin aut Oscar Leyton verfasserin aut Jaime R. Cabrera-Pardo verfasserin aut Bernd Schmidt verfasserin aut Matthias Heydenreich verfasserin aut Viviana Burgos verfasserin aut Paola Duran verfasserin aut Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 21, p 12995 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:21, p 12995 https://doi.org/10.3390/ijms232112995 kostenfrei https://doaj.org/article/e5f2377139654bd387b07920063ed5b5 kostenfrei https://www.mdpi.com/1422-0067/23/21/12995 kostenfrei https://doaj.org/toc/1661-6596 Journal toc kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 23 2022 21, p 12995
allfieldsSound	10.3390/ijms232112995 doi (DE-627)DOAJ028693663 (DE-599)DOAJe5f2377139654bd387b07920063ed5b5 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Nicole Cortez verfasserin aut Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i< 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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. <i<Drimys winteri</i< <i<Cladosporium antarcticum</i< drimendiol epidrimendiol biotransformation <i<Candida</i< yeast Biology (General) Chemistry Víctor Marín verfasserin aut Verónica A. Jiménez verfasserin aut Víctor Silva verfasserin aut Oscar Leyton verfasserin aut Jaime R. Cabrera-Pardo verfasserin aut Bernd Schmidt verfasserin aut Matthias Heydenreich verfasserin aut Viviana Burgos verfasserin aut Paola Duran verfasserin aut Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 21, p 12995 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:21, p 12995 https://doi.org/10.3390/ijms232112995 kostenfrei https://doaj.org/article/e5f2377139654bd387b07920063ed5b5 kostenfrei https://www.mdpi.com/1422-0067/23/21/12995 kostenfrei https://doaj.org/toc/1661-6596 Journal toc kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 23 2022 21, p 12995
language	English
source	In International Journal of Molecular Sciences 23(2022), 21, p 12995 volume:23 year:2022 number:21, p 12995
sourceStr	In International Journal of Molecular Sciences 23(2022), 21, p 12995 volume:23 year:2022 number:21, p 12995
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	<i<Drimys winteri</i< <i<Cladosporium antarcticum</i< drimendiol epidrimendiol biotransformation <i<Candida</i< yeast Biology (General) Chemistry
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container_title	International Journal of Molecular Sciences
authorswithroles_txt_mv	Nicole Cortez @@aut@@ Víctor Marín @@aut@@ Verónica A. Jiménez @@aut@@ Víctor Silva @@aut@@ Oscar Leyton @@aut@@ Jaime R. Cabrera-Pardo @@aut@@ Bernd Schmidt @@aut@@ Matthias Heydenreich @@aut@@ Viviana Burgos @@aut@@ Paola Duran @@aut@@ Cristian Paz @@aut@@
publishDateDaySort_date	2022-01-01T00:00:00Z
hierarchy_top_id	316340715
id	DOAJ028693663
language_de	englisch
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author	Nicole Cortez
spellingShingle	Nicole Cortez misc QH301-705.5 misc QD1-999 misc <i<Drimys winteri</i< misc <i<Cladosporium antarcticum</i< misc drimendiol misc epidrimendiol misc biotransformation misc <i<Candida</i< yeast misc Biology (General) misc Chemistry Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i<
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topic_title	QH301-705.5 QD1-999 Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i< <i<Drimys winteri</i< <i<Cladosporium antarcticum</i< drimendiol epidrimendiol biotransformation <i<Candida</i< yeast
topic	misc QH301-705.5 misc QD1-999 misc <i<Drimys winteri</i< misc <i<Cladosporium antarcticum</i< misc drimendiol misc epidrimendiol misc biotransformation misc <i<Candida</i< yeast misc Biology (General) misc Chemistry
topic_unstemmed	misc QH301-705.5 misc QD1-999 misc <i<Drimys winteri</i< misc <i<Cladosporium antarcticum</i< misc drimendiol misc epidrimendiol misc biotransformation misc <i<Candida</i< yeast misc Biology (General) misc Chemistry
topic_browse	misc QH301-705.5 misc QD1-999 misc <i<Drimys winteri</i< misc <i<Cladosporium antarcticum</i< misc drimendiol misc epidrimendiol misc biotransformation misc <i<Candida</i< yeast misc Biology (General) misc Chemistry
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title	Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i<
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title_full	Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i<
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author_browse	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
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title_sort	drimane sesquiterpene alcohols with activity against <i<candida</i< yeast obtained by biotransformation with <i<cladosporium antarcticum</i<
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title_auth	Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i<
abstract	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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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.
abstractGer	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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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.
abstract_unstemmed	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, <i<Cladosporium antarcticum</i< isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against <i<Candida</i< yeast from drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH<sub<4</sub< in methanol. <i<Cladosporium antarcticum</i< produced two major products from drimendiol, identified as 9α-hydroxydrimendiol (<b<1</b<, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (<b<2</b<, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (<b<3</b<, 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 <b<1</b<–<b<3</b< was analyzed against <i<Candida albicans</i<, <i<C. krusei</i< and <i<C. parapsilosis</i<, showing that compound <b<2</b< 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.
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container_issue	21, p 12995
title_short	Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i<
url	https://doi.org/10.3390/ijms232112995 https://doaj.org/article/e5f2377139654bd387b07920063ed5b5 https://www.mdpi.com/1422-0067/23/21/12995 https://doaj.org/toc/1661-6596 https://doaj.org/toc/1422-0067
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Drimane Sesquiterpene Alcohols with Activity against <i<Candida</i< Yeast Obtained by Biotransformation with <i<Cladosporium antarcticum</i<

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