Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2

Estrone, estradiol, ethynylestradiol and estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transfo...

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Autores principales: Kozłowska, Ewa, Dymarska, Monika, Kostrzewa-Susłow, Edyta, Janeczko, Tomasz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6656742/
https://www.ncbi.nlm.nih.gov/pubmed/31341201
http://dx.doi.org/10.1038/s41598-019-47225-1
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author Kozłowska, Ewa
Dymarska, Monika
Kostrzewa-Susłow, Edyta
Janeczko, Tomasz
author_facet Kozłowska, Ewa
Dymarska, Monika
Kostrzewa-Susłow, Edyta
Janeczko, Tomasz
author_sort Kozłowska, Ewa
collection PubMed
description Estrone, estradiol, ethynylestradiol and estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transformed to D-ring lactone. Ethynylestradiol was coupled with methylglucoside and 6β-hydroxyderivative was obtained. Estrone 3-methyl ether was not transformed indicating that a free hydroxyl group at C-3 is necessary for glycosylation. Baeyer–Villiger oxidation combined with hydroxylation and glycosylation was observed. All glycosides obtained in this study are 3-O-β-methylglucosides.
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spelling pubmed-66567422019-07-29 Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2 Kozłowska, Ewa Dymarska, Monika Kostrzewa-Susłow, Edyta Janeczko, Tomasz Sci Rep Article Estrone, estradiol, ethynylestradiol and estrone 3-methyl ether underwent a biotransformation process in the submerged culture of Isaria fumosorosea KCh J2. Estrone was transformed into seven metabolites, four of which were glycosylated. Estradiol was selectively glycosylated at C-3 and then transformed to D-ring lactone. Ethynylestradiol was coupled with methylglucoside and 6β-hydroxyderivative was obtained. Estrone 3-methyl ether was not transformed indicating that a free hydroxyl group at C-3 is necessary for glycosylation. Baeyer–Villiger oxidation combined with hydroxylation and glycosylation was observed. All glycosides obtained in this study are 3-O-β-methylglucosides. Nature Publishing Group UK 2019-07-24 /pmc/articles/PMC6656742/ /pubmed/31341201 http://dx.doi.org/10.1038/s41598-019-47225-1 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Kozłowska, Ewa
Dymarska, Monika
Kostrzewa-Susłow, Edyta
Janeczko, Tomasz
Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2
title Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2
title_full Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2
title_fullStr Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2
title_full_unstemmed Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2
title_short Cascade biotransformation of estrogens by Isaria fumosorosea KCh J2
title_sort cascade biotransformation of estrogens by isaria fumosorosea kch j2
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6656742/
https://www.ncbi.nlm.nih.gov/pubmed/31341201
http://dx.doi.org/10.1038/s41598-019-47225-1
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