67400-17-3Relevant 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 (2018/03/26)
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.
Highly efficient biotransformation of ginsenoside Rb1 and Rg3 using β-galactosidase from Aspergillus sp.
Wan, Hui-Da,Li, Dan
, p. 78874 - 78879 (2015/10/05)
A preliminary study on the enzymatic biotransformation of ginsenosides is evaluated. β-Galactosidase from Aspergillus sp. displayed β-glucosidase activity, which was responsible for its ability to transform major ginsenoside Rb1 to rare ginsenoside F2 via ginsenoside Rd. The Rb1 conversion, Rd and F2 yields reached 100%, 80.7% and 14.3% after 60 h at 60 °C, respectively. Ginsenoside Rg3 can be selectively hydrolyzed and only Rh2 was obtained with this β-galactosidase as well. Before hydrolysis, an Rg3 inclusion complex was prepared with hydroxypropyl-β-cyclodextrin (HP-β-CD) to improve the aqueous solubility. The solubility of Rg3 increased 74.6 fold, and the phase solubility curve displayed a typical AL-type, which indicates the formation of a 1 : 1 inclusion complex. Using an enzyme loading of 500 U g-1 Rg3, the highest Rg3 conversion of 90.6% and Rh2 yield of 88.5% were obtained after 24 h at 60 °C. These results indicate that β-galactosidase from Aspergillus sp. could be useful for the mass production of rare ginsenosides.
Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor
Liao, Jinxi,Sun, Jiansong,Niu, Yiming,Yu, Biao
scheme or table, p. 3075 - 3078 (2011/06/26)
Glycosylation of the acid labile protopanaxadiol derivatives was succeeded with a glycosyl ortho-hexynylbenzoate as donor under the catalysis of PPh 3AuNTf2, leading to the subsequent elaboration of ginsenoside Rh2 and chikusetsusaponin-LT8 in a concise manner.
