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Biotransformation of celastrol to a novel, well-soluble, low-toxic and anti-oxidative celastrol-29-O-β-glucoside by Bacillus glycosyltransferases.
- Source :
-
Journal of bioscience and bioengineering [J Biosci Bioeng] 2021 Feb; Vol. 131 (2), pp. 176-182. Date of Electronic Publication: 2020 Oct 23. - Publication Year :
- 2021
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Abstract
- Celastrol is a quinone-methide triterpenoid isolated from the root extracts of Tripterygium wilfordii (Thunder god vine). Although celastrol possesses multiple bioactivities, the potent toxicity and rare solubility in water hinder its clinical application. Biotransformation of celastrol using either whole cells or purified enzymes to form less toxic and more soluble derivatives has been proven difficult due to its potent antibiotic and enzyme-conjugation property. The present study evaluated biotransformation of celastrol by four glycosyltransferases from Bacillus species and found one glycosyltransferase (BsGT110) from Bacillus subtilis with significant activity toward celastrol. The biotransformation metabolite was purified and identified as celastrol-29-O-β-glucoside by mass and nuclear magnetic resonance spectroscopy. Celastrol-29-O-β-glucoside showed over 53-fold higher water solubility than celastrol, while maintained 50% of the free radical scavenging activity of celastrol. When using zebrafish as the in vivo animal model, celastrol-29-O-β-glucoside exhibited 50-fold less toxicity than celastrol. To our knowledge, the present study is not only the first report describing the biotransformation of celastrol, but also the first one detailing a new compound, celastrol-29-O-β-glucoside, that is generated in the biotransformation process. Moreover, celastrol-29-O-β-glucoside may serve as a potential candidate in the future medicine application due to its higher water solubility and lower toxicity.<br /> (Copyright © 2020 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.)
- Subjects :
- Animals
Antioxidants toxicity
Bacillus subtilis metabolism
Biotransformation
Glucosides toxicity
Pentacyclic Triterpenes
Solubility
Antioxidants chemistry
Antioxidants metabolism
Bacillus subtilis enzymology
Glucosides chemistry
Glucosides metabolism
Glycosyltransferases metabolism
Triterpenes metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1347-4421
- Volume :
- 131
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Journal of bioscience and bioengineering
- Publication Type :
- Academic Journal
- Accession number :
- 33268318
- Full Text :
- https://doi.org/10.1016/j.jbiosc.2020.09.017