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Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones

Three β-cyclocitral-derived halolactones, which exhibit antifeedant activity towards storage product pests, were subjected to microbial transformation processes. Among the thirty tested strains of filamentous fungi and yeast, the most effective biocatalysts were Absidia cylindrospora AM336, Mortiere...

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Autores principales: Mazur, Marcelina, Gładkowski, Witold, Srček, Višnja Gaurina, Radošević, Kristina, Maciejewska, Gabriela, Wawrzeńczyk, Czesław
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5570294/
https://www.ncbi.nlm.nih.gov/pubmed/28837605
http://dx.doi.org/10.1371/journal.pone.0183429
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author Mazur, Marcelina
Gładkowski, Witold
Srček, Višnja Gaurina
Radošević, Kristina
Maciejewska, Gabriela
Wawrzeńczyk, Czesław
author_facet Mazur, Marcelina
Gładkowski, Witold
Srček, Višnja Gaurina
Radošević, Kristina
Maciejewska, Gabriela
Wawrzeńczyk, Czesław
author_sort Mazur, Marcelina
collection PubMed
description Three β-cyclocitral-derived halolactones, which exhibit antifeedant activity towards storage product pests, were subjected to microbial transformation processes. Among the thirty tested strains of filamentous fungi and yeast, the most effective biocatalysts were Absidia cylindrospora AM336, Mortierella isabellina AM212 and Mortierella vinaceae AM149. As a result of regio- and enantioselective hydroxylation four new oxygenated derivatives were obtained. Regardless of the biocatalyst applied, the δ-iodo- and δ-bromo-γ-lactones were hydroxylated in an inactivated position C-5 of cyclohexane ring. The analogous transformation of chlorolactone was observed in Mortierella isabellina AM212 culture but in the case of two other biocatalysts the hydroxy group was introduced at C-3 position. All obtained hydroxylactones were enantiomerically pure (ee = 100%) or enriched (ee = 50%). The highest enantioselectivity of hydroxylation was observed for M. isabellina AM212. The cytotoxic activity of halolactones was also examined by WST-1 assay wherein tested compounds did not exhibit significant effect on the viability of tumor HeLa and normal CHO-K1 cells.
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spelling pubmed-55702942017-09-09 Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones Mazur, Marcelina Gładkowski, Witold Srček, Višnja Gaurina Radošević, Kristina Maciejewska, Gabriela Wawrzeńczyk, Czesław PLoS One Research Article Three β-cyclocitral-derived halolactones, which exhibit antifeedant activity towards storage product pests, were subjected to microbial transformation processes. Among the thirty tested strains of filamentous fungi and yeast, the most effective biocatalysts were Absidia cylindrospora AM336, Mortierella isabellina AM212 and Mortierella vinaceae AM149. As a result of regio- and enantioselective hydroxylation four new oxygenated derivatives were obtained. Regardless of the biocatalyst applied, the δ-iodo- and δ-bromo-γ-lactones were hydroxylated in an inactivated position C-5 of cyclohexane ring. The analogous transformation of chlorolactone was observed in Mortierella isabellina AM212 culture but in the case of two other biocatalysts the hydroxy group was introduced at C-3 position. All obtained hydroxylactones were enantiomerically pure (ee = 100%) or enriched (ee = 50%). The highest enantioselectivity of hydroxylation was observed for M. isabellina AM212. The cytotoxic activity of halolactones was also examined by WST-1 assay wherein tested compounds did not exhibit significant effect on the viability of tumor HeLa and normal CHO-K1 cells. Public Library of Science 2017-08-24 /pmc/articles/PMC5570294/ /pubmed/28837605 http://dx.doi.org/10.1371/journal.pone.0183429 Text en © 2017 Mazur et al http://creativecommons.org/licenses/by/4.0/ This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
spellingShingle Research Article
Mazur, Marcelina
Gładkowski, Witold
Srček, Višnja Gaurina
Radošević, Kristina
Maciejewska, Gabriela
Wawrzeńczyk, Czesław
Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones
title Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones
title_full Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones
title_fullStr Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones
title_full_unstemmed Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones
title_short Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones
title_sort regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5570294/
https://www.ncbi.nlm.nih.gov/pubmed/28837605
http://dx.doi.org/10.1371/journal.pone.0183429
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