Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients

<i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterd...
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Autor*in:	Víctor Marín [verfasserIn] Bryan Bart [verfasserIn] Nicole Cortez [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] Cristian Paz [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	drimane sesquiterpenoids isotadeonal winterdial lanosterol 14-α-demethylase

Übergeordnetes Werk:	In: International Journal of Molecular Sciences - MDPI AG, 2003, 23(2022), 19, p 11753
Übergeordnetes Werk:	volume:23 ; year:2022 ; number:19, p 11753

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

DOI / URN:	10.3390/ijms231911753

Katalog-ID:	DOAJ028319818

Internformat


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allfields	10.3390/ijms231911753 doi (DE-627)DOAJ028319818 (DE-599)DOAJdcdc3b010a8a4cdda1c8a5f48ae35cc2 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Víctor Marín verfasserin aut Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds. drimane sesquiterpenoids <i<Drimys winteri</i< isotadeonal winterdial <i<Candida</i< yeast lanosterol 14-α-demethylase Biology (General) Chemistry Bryan Bart verfasserin aut Nicole Cortez 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 Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 19, p 11753 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:19, p 11753 https://doi.org/10.3390/ijms231911753 kostenfrei https://doaj.org/article/dcdc3b010a8a4cdda1c8a5f48ae35cc2 kostenfrei https://www.mdpi.com/1422-0067/23/19/11753 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 19, p 11753
spelling	10.3390/ijms231911753 doi (DE-627)DOAJ028319818 (DE-599)DOAJdcdc3b010a8a4cdda1c8a5f48ae35cc2 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Víctor Marín verfasserin aut Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds. drimane sesquiterpenoids <i<Drimys winteri</i< isotadeonal winterdial <i<Candida</i< yeast lanosterol 14-α-demethylase Biology (General) Chemistry Bryan Bart verfasserin aut Nicole Cortez 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 Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 19, p 11753 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:19, p 11753 https://doi.org/10.3390/ijms231911753 kostenfrei https://doaj.org/article/dcdc3b010a8a4cdda1c8a5f48ae35cc2 kostenfrei https://www.mdpi.com/1422-0067/23/19/11753 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 19, p 11753
allfields_unstemmed	10.3390/ijms231911753 doi (DE-627)DOAJ028319818 (DE-599)DOAJdcdc3b010a8a4cdda1c8a5f48ae35cc2 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Víctor Marín verfasserin aut Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds. drimane sesquiterpenoids <i<Drimys winteri</i< isotadeonal winterdial <i<Candida</i< yeast lanosterol 14-α-demethylase Biology (General) Chemistry Bryan Bart verfasserin aut Nicole Cortez 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 Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 19, p 11753 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:19, p 11753 https://doi.org/10.3390/ijms231911753 kostenfrei https://doaj.org/article/dcdc3b010a8a4cdda1c8a5f48ae35cc2 kostenfrei https://www.mdpi.com/1422-0067/23/19/11753 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 19, p 11753
allfieldsGer	10.3390/ijms231911753 doi (DE-627)DOAJ028319818 (DE-599)DOAJdcdc3b010a8a4cdda1c8a5f48ae35cc2 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Víctor Marín verfasserin aut Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds. drimane sesquiterpenoids <i<Drimys winteri</i< isotadeonal winterdial <i<Candida</i< yeast lanosterol 14-α-demethylase Biology (General) Chemistry Bryan Bart verfasserin aut Nicole Cortez 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 Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 19, p 11753 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:19, p 11753 https://doi.org/10.3390/ijms231911753 kostenfrei https://doaj.org/article/dcdc3b010a8a4cdda1c8a5f48ae35cc2 kostenfrei https://www.mdpi.com/1422-0067/23/19/11753 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 19, p 11753
allfieldsSound	10.3390/ijms231911753 doi (DE-627)DOAJ028319818 (DE-599)DOAJdcdc3b010a8a4cdda1c8a5f48ae35cc2 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Víctor Marín verfasserin aut Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds. drimane sesquiterpenoids <i<Drimys winteri</i< isotadeonal winterdial <i<Candida</i< yeast lanosterol 14-α-demethylase Biology (General) Chemistry Bryan Bart verfasserin aut Nicole Cortez 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 Cristian Paz verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 23(2022), 19, p 11753 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:23 year:2022 number:19, p 11753 https://doi.org/10.3390/ijms231911753 kostenfrei https://doaj.org/article/dcdc3b010a8a4cdda1c8a5f48ae35cc2 kostenfrei https://www.mdpi.com/1422-0067/23/19/11753 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 19, p 11753
language	English
source	In International Journal of Molecular Sciences 23(2022), 19, p 11753 volume:23 year:2022 number:19, p 11753
sourceStr	In International Journal of Molecular Sciences 23(2022), 19, p 11753 volume:23 year:2022 number:19, p 11753
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	drimane sesquiterpenoids <i<Drimys winteri</i< isotadeonal winterdial <i<Candida</i< yeast lanosterol 14-α-demethylase Biology (General) Chemistry
isfreeaccess_bool	true
container_title	International Journal of Molecular Sciences
authorswithroles_txt_mv	Víctor Marín @@aut@@ Bryan Bart @@aut@@ Nicole Cortez @@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@@ Cristian Paz @@aut@@
publishDateDaySort_date	2022-01-01T00:00:00Z
hierarchy_top_id	316340715
id	DOAJ028319818
language_de	englisch
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callnumber-first	Q - Science
author	Víctor Marín
spellingShingle	Víctor Marín misc QH301-705.5 misc QD1-999 misc drimane sesquiterpenoids misc <i<Drimys winteri</i< misc isotadeonal misc winterdial misc <i<Candida</i< yeast misc lanosterol 14-α-demethylase misc Biology (General) misc Chemistry Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients
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topic_title	QH301-705.5 QD1-999 Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients drimane sesquiterpenoids <i<Drimys winteri</i< isotadeonal winterdial <i<Candida</i< yeast lanosterol 14-α-demethylase
topic	misc QH301-705.5 misc QD1-999 misc drimane sesquiterpenoids misc <i<Drimys winteri</i< misc isotadeonal misc winterdial misc <i<Candida</i< yeast misc lanosterol 14-α-demethylase misc Biology (General) misc Chemistry
topic_unstemmed	misc QH301-705.5 misc QD1-999 misc drimane sesquiterpenoids misc <i<Drimys winteri</i< misc isotadeonal misc winterdial misc <i<Candida</i< yeast misc lanosterol 14-α-demethylase misc Biology (General) misc Chemistry
topic_browse	misc QH301-705.5 misc QD1-999 misc drimane sesquiterpenoids misc <i<Drimys winteri</i< misc isotadeonal misc winterdial misc <i<Candida</i< yeast misc lanosterol 14-α-demethylase misc Biology (General) misc Chemistry
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title	Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients
ctrlnum	(DE-627)DOAJ028319818 (DE-599)DOAJdcdc3b010a8a4cdda1c8a5f48ae35cc2
title_full	Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients
author_sort	Víctor Marín
journal	International Journal of Molecular Sciences
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author_browse	Víctor Marín Bryan Bart Nicole Cortez Verónica A. Jiménez Víctor Silva Oscar Leyton Jaime R. Cabrera-Pardo Bernd Schmidt Matthias Heydenreich Viviana Burgos Cristian Paz
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author-letter	Víctor Marín
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title_sort	drimane sesquiterpene aldehydes control <i<candida</i< yeast isolated from candidemia in chilean patients
callnumber	QH301-705.5
title_auth	Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients
abstract	<i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds.
abstractGer	<i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds.
abstract_unstemmed	<i<Drimys winteri</i< J.R. (Winteraceae) produce drimane sesquiterpenoids with activity against <i<Candida</i< yeast. In this work, drimenol, polygodial (<b<1</b<), isotadeonal (<b<2</b<), and a new drimane α,β-unsaturated 1,4-dialdehyde, named winterdial (<b<4</b<), were purified from barks of <i<D. winteri</i<. The oxidation of drimenol produced the monoaldehyde drimenal (<b<3</b<). These four aldehyde sesquiterpenoids were evaluated against six <i<Candida</i< species isolated from candidemia patients in Chilean hospitals. Results showed that <b<1</b< displays fungistatic activity against all yeasts (3.75 to 15.0 µg/mL), but irritant effects on eyes and skin, whereas its non-pungent epimer <b<2</b< has fungistatic and fungicide activities at 1.9 and 15.0 µg/mL, respectively. On the other hand, compounds <b<3</b< and <b<4</b< were less active. Molecular dynamics simulations suggested that compounds <b<1</b<–<b<4</b< are capable of binding to the catalytic pocket of lanosterol 14-alpha demethylase with similar binding free energies, thus suggesting a potential mechanism of action through the inhibition of ergosterol synthesis. According to our findings, compound <b<2</b< appears as a valuable molecular scaffold to pursue the future development of more potent drugs against candidiasis with fewer side effects than polygodial. These outcomes are significant to broaden the alternatives to treat fungal infections with increasing prevalence worldwide using natural compounds as a primary source for active compounds.
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title_short	Drimane Sesquiterpene Aldehydes Control <i<Candida</i< Yeast Isolated from Candidemia in Chilean Patients
url	https://doi.org/10.3390/ijms231911753 https://doaj.org/article/dcdc3b010a8a4cdda1c8a5f48ae35cc2 https://www.mdpi.com/1422-0067/23/19/11753 https://doaj.org/toc/1661-6596 https://doaj.org/toc/1422-0067
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author2	Bryan Bart Nicole Cortez Verónica A. Jiménez Víctor Silva Oscar Leyton Jaime R. Cabrera-Pardo Bernd Schmidt Matthias Heydenreich Viviana Burgos Cristian Paz
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