Semi-Synthesis and Cellular Effects of Three Different Ginsenosides Derived from Re, Rh.sub.1, and PPT

• Published in: Chemistry of natural compounds Vol. 55; no. 1; pp. 66 - 73
• Main Authors: Ding, Hongda, Chen, Yanping, Chen, Shuang, Li, Man Man, Tan, Zhao Yi, Lu, Zhen Yao, Zhang, Pengfei
• Format: Journal Article
• Language: English
• Published: Springer 01.01.2019
• Subjects: Cancer cells
• ISSN: 0009-3130; 1573-8388
• DOI: 10.1007/s10600-019-02615-9

3[beta],12[beta],25-Trihydroxydammar-(E/Z)-20(22)-ene-6-O-[alpha]-L-rhamnopyranosyl-(1[right arrow]2)-[beta]-D-glucopyranoside, 3[beta],2[beta],25-trihydroxydammar-(E/Z)-20(22)-ene-6-O-[beta]-D-glucopyranoside, and dammar-20(22)-ene-3,6,12,25-tetrol(3[beta],6[beta],12[beta],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(3[beta],6[beta],12[beta],20Z) was identified as a new triterpenoid ginsenoside. The cytotoxic and hemolytic effects of these compounds towards cancer cells and erythrocytes were also evaluated.