117666-46-3Relevant articles and documents
One-Pot Synthesis of Ginsenoside Rh2 and Bioactive Unnatural Ginsenoside by Coupling Promiscuous Glycosyltransferase from Bacillus subtilis 168 to Sucrose Synthase
Dai, Longhai,Liu, Can,Li, Jiao,Dong, Caixia,Yang, Jiangang,Dai, Zhubo,Zhang, Xueli,Sun, Yuanxia
, p. 2830 - 2837 (2018)
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.
