One-Pot Synthesis of Ginsenoside Rh2 and Bioactive Unnatural Ginsenoside by Coupling Promiscuous Glycosyltransferase from Bacillus subtilis 168 to Sucrose Synthase

Journal of Agricultural and Food Chemistry
Longhai DaiYuanxia Sun

Abstract

Ginsenosides, the major effective ingredients of Panax ginseng, exhibit various biological properties. UDP-glycosyltransferase (UGT)-mediated glycosylation is the last biosynthetic step of ginsenosides and contributes to their immense structural and functional diversity. In this study, UGT Bs-YjiC from Bacillus subtilis 168 was demonstrated to transfer a glucosyl moiety to the free C3-OH and C12-OH of protopanaxadiol (PPD) and PPD-type ginsenosides to synthesize natural and unnatural ginsenosides. In vitro assays showed that unnatural ginsenoside F12 (3- O-β-d-glucopyranosyl-12- O-β-d-glucopyranosyl-20( S)-protopanaxadiol) exhibited remarkable activity against diverse human cancer cell lines. A one-pot reaction by coupling Bs-YjiC to sucrose synthase (SuSy) was performed to regenerate UDP-glucose from sucrose and UDP. With PPD as the aglycon, an unprecedented high yield of ginsenosides F12 (3.98 g L-1) and Rh2 (0.20 g L-1) was obtained by optimizing the conversion conditions. This study provides an efficient approach for the biosynthesis of ginsenosides using a UGT-SuSy cascade reaction.

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Citations

Nov 5, 2020·Bioprocess and Biosystems Engineering·Bin YuanAiling Liu
Aug 14, 2021·Acta Pharmaceutica Sinica. B·Maoqi HouZhengtao Wang
Nov 6, 2018·Journal of Agricultural and Food Chemistry·Yu-Jia Zhao, Chun Li
Mar 29, 2020·ACS Synthetic Biology·Xiangdong PuJingyuan Song
Oct 19, 2019·Journal of Agricultural and Food Chemistry·Feng LiuGuangji Wang
Oct 27, 2021·Journal of Agricultural and Food Chemistry·Yaping MaoYong Wang

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