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Molecules 2018, 23(7), 1783; https://doi.org/10.3390/molecules23071783

Bioconversion of Corticosterone into Corticosterone-Glucoside by Glucosyltransferase

1
Department of Pharmaceutical Engineering and Biotechnology, Sun Moon University, 70 Sunmoon-ro 221, Tangjeong-myeon, Asan-si, Chungnam 31460, Korea
2
Genome-based BioIT Convergence Institute, 70 Sunmoon-ro 221, Tangjeong-myeon, Asan-si, Chungnam 31460, Korea
3
Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sunmoon-ro 221, Tangjeong-myeon, Asan-si, Chungnam 31460, Korea
4
Korea Institute of Oriental Medicine, 1672 Yuseongdae-ro, Yuseong-gu, Daejeon 305-811, Korea
5
Genomics Division, National Institute of Agricultural Science, RDA, Jeonju 54874, Korea
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Jia Zhou
Received: 6 June 2018 / Revised: 16 July 2018 / Accepted: 17 July 2018 / Published: 19 July 2018
(This article belongs to the Special Issue Neuroprotective Agents)
Full-Text   |   PDF [2325 KB, uploaded 19 July 2018]   |  

Abstract

Glucosylation of the 21-hydroxyl group of glucocorticoid changes its solubility into hydrophilicity from hydrophobicity and, as with glucocorticoid glucuronides as a moving object in vivo, it is conceivable that it exhibits the same behavior. Therefore, glucosylation to the 21-hydroxyl group while maintaining the 11β-hydroxyl group is particularly important, and glucosylation of corticosterone was confirmed by high-resolution mass spectrometry and 1D (1H and 13C) and 2D (COSY, ROESY, HSQC-DEPT and HMBC) NMR. Moreover, the difference in bioactivity between corticosterone and corticosterone 21-glucoside was investigated in vitro. Corticosterone 21-glucoside showed greater neuroprotective effects against H2O2-induced cell death and reactive oxygen species (ROS) compared with corticosterone. These results for the first time demonstrate that bioconversion of corticosterone through the region-selective glucosylation of a novel compound can present structural potential for developing new neuroprotective agents. View Full-Text
Keywords: corticosterone; enzymatic glucosylation; glucocorticoid; NMR; steroid corticosterone; enzymatic glucosylation; glucocorticoid; NMR; steroid
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Yamaguchi, T.; Lee, J.-H.; Lim, A.-R.; Sim, J.-S.; Yu, E.-J.; Oh, T.-J. Bioconversion of Corticosterone into Corticosterone-Glucoside by Glucosyltransferase. Molecules 2018, 23, 1783.

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