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Semi-Synthesis and Cellular Effects of Three Different Ginsenosides Derived from Re, Rh1, and PPT
- Ding, Hongda, Chen, Yanping, Chen, Shuang, Li, Man Man, Tan, Zhao Yi, Lu, Zhen Yao, Zhang, Pengfei, Gao, Wei, Xu, Yan, Xu, Fangfei, Wang, Zhicai
- Chemistry of natural compounds 2019 v.55 no.1 pp. 66-73
- acetylation, cytotoxicity, erythrocytes, ginsenosides, neoplasm cells, neoplasms, nuclear magnetic resonance spectroscopy, saponification
- 3β,12β,25-Trihydroxydammar-(E/Z)-20(22)-ene-6-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside, 3β,2β,25-trihydroxydammar-(E/Z)-20(22)-ene-6-O-β-D-glucopyranoside, and dammar-20(22)-ene-3,6,12,25-tetrol(3β,6β,12β,20E/Z) were synthesized from the ginsenosides Re, Rh1, and PPT, respectively, via a simple three-step process involving acetylation, elimination-addition, and saponification. We obtained the detailed structures of these compounds by 1D and 2D NMR, and by HR-ESI-MS. Among them, dammar-20(22)-ene-3,6,12,25-tetrol(3β,6β,12β,20Z) was identified as a new triterpenoid ginsenoside. The cytotoxic and hemolytic effects of these compounds towards cancer cells and erythrocytes were also evaluated.