Cargando…

Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288

The application of steroids has steadily increased thanks to their therapeutic effects. However, alternatives are required due their severe side effects; thus, studies on the activities of steroid derivatives are underway. Sugar derivatives of nandrolone, which is used to treat breast cancer, as wel...

Descripción completa

Detalles Bibliográficos
Autores principales: Yu, Eun-Ji, Yamaguchi, Tokutaro, Lee, Joo-Ho, Lim, A-Rang, Lee, Jun Hyuck, Park, Hyun, Oh, Tae-Jin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Korean Society for Microbiology and Biotechnology 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9728329/
https://www.ncbi.nlm.nih.gov/pubmed/31893610
http://dx.doi.org/10.4014/jmb.1911.11057
_version_ 1784845225742565376
author Yu, Eun-Ji
Yamaguchi, Tokutaro
Lee, Joo-Ho
Lim, A-Rang
Lee, Jun Hyuck
Park, Hyun
Oh, Tae-Jin
author_facet Yu, Eun-Ji
Yamaguchi, Tokutaro
Lee, Joo-Ho
Lim, A-Rang
Lee, Jun Hyuck
Park, Hyun
Oh, Tae-Jin
author_sort Yu, Eun-Ji
collection PubMed
description The application of steroids has steadily increased thanks to their therapeutic effects. However, alternatives are required due their severe side effects; thus, studies on the activities of steroid derivatives are underway. Sugar derivatives of nandrolone, which is used to treat breast cancer, as well as cortisone and prednisone, which reduce inflammation, pain, and edema, are unknown. We linked O-glucose to nandrolone and testosterone using UDP-glucosyltransferase (UGT-1) and, then, tested their bioactivities in vitro. Analysis by NMR showed that the derivatives were 17β-nandrolone β-D-glucose and 17β-testosterone β-D-glucose, respectively. The viability was higher and cytotoxicity was evident in PC12 cells incubated with rotenone and, testosterone derivatives, compared to the controls. SH-SY5Y cells incubated with H(2)O(2) and nandrolone derivatives remained viable and cytotoxicity was attenuated. Both derivatives enhanced neuronal protective effects and increased the amounts of cellular ATP.
format Online
Article
Text
id pubmed-9728329
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Korean Society for Microbiology and Biotechnology
record_format MEDLINE/PubMed
spelling pubmed-97283292022-12-13 Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288 Yu, Eun-Ji Yamaguchi, Tokutaro Lee, Joo-Ho Lim, A-Rang Lee, Jun Hyuck Park, Hyun Oh, Tae-Jin J Microbiol Biotechnol Research article The application of steroids has steadily increased thanks to their therapeutic effects. However, alternatives are required due their severe side effects; thus, studies on the activities of steroid derivatives are underway. Sugar derivatives of nandrolone, which is used to treat breast cancer, as well as cortisone and prednisone, which reduce inflammation, pain, and edema, are unknown. We linked O-glucose to nandrolone and testosterone using UDP-glucosyltransferase (UGT-1) and, then, tested their bioactivities in vitro. Analysis by NMR showed that the derivatives were 17β-nandrolone β-D-glucose and 17β-testosterone β-D-glucose, respectively. The viability was higher and cytotoxicity was evident in PC12 cells incubated with rotenone and, testosterone derivatives, compared to the controls. SH-SY5Y cells incubated with H(2)O(2) and nandrolone derivatives remained viable and cytotoxicity was attenuated. Both derivatives enhanced neuronal protective effects and increased the amounts of cellular ATP. The Korean Society for Microbiology and Biotechnology 2020-04-28 2019-12-30 /pmc/articles/PMC9728329/ /pubmed/31893610 http://dx.doi.org/10.4014/jmb.1911.11057 Text en Copyright© 2020 by The Korean Society for Microbiology and Biotechnology https://creativecommons.org/licenses/by/4.0/This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Research article
Yu, Eun-Ji
Yamaguchi, Tokutaro
Lee, Joo-Ho
Lim, A-Rang
Lee, Jun Hyuck
Park, Hyun
Oh, Tae-Jin
Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288
title Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288
title_full Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288
title_fullStr Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288
title_full_unstemmed Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288
title_short Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288
title_sort enzymatic synthesis of anabolic steroid glycosides by glucosyltransferase from terribacillus sp. pamc 23288
topic Research article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9728329/
https://www.ncbi.nlm.nih.gov/pubmed/31893610
http://dx.doi.org/10.4014/jmb.1911.11057
work_keys_str_mv AT yueunji enzymaticsynthesisofanabolicsteroidglycosidesbyglucosyltransferasefromterribacillussppamc23288
AT yamaguchitokutaro enzymaticsynthesisofanabolicsteroidglycosidesbyglucosyltransferasefromterribacillussppamc23288
AT leejooho enzymaticsynthesisofanabolicsteroidglycosidesbyglucosyltransferasefromterribacillussppamc23288
AT limarang enzymaticsynthesisofanabolicsteroidglycosidesbyglucosyltransferasefromterribacillussppamc23288
AT leejunhyuck enzymaticsynthesisofanabolicsteroidglycosidesbyglucosyltransferasefromterribacillussppamc23288
AT parkhyun enzymaticsynthesisofanabolicsteroidglycosidesbyglucosyltransferasefromterribacillussppamc23288
AT ohtaejin enzymaticsynthesisofanabolicsteroidglycosidesbyglucosyltransferasefromterribacillussppamc23288