کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
2027509 | 1542702 | 2016 | 9 صفحه PDF | دانلود رایگان |
• Twenty-two ginsenosides were systematically synthesized and cytotoxicity was evaluated.
• Eight ginsenosides were firstly identified based on 1D, 2D NMR and HR-ESIMS.
• The number of glycosyl and C-configuration have great influence on the cytotoxicity.
• Eleven ginsenosides have cytotoxicity and deserved further investigation.
A series of oxidized products have been systematically semisynthesized from 20(S)-ginsenoside Rg3, Rh2, 20(S)-protopanaxadiol (PPD) and their 20(R)-epimers and the majority of these products were evaluated for their cytotoxic activity against HeLa cells and HepG2 cells by MTT assay for the first time. Twenty-two products were obtained and elucidated based on comprehensive 1H NMR, 13C NMR, two-dimensional (2D) NMR, and mass spectral data and the results reported in previous literature. All the four ocotillol type saponins (20S,24R(δ86, δ85); 20S,24S(δ87, δ88); 20R,24R(δ86, δ86); 20R,24S(δ86, δ87) were obtained. In addition, eight compounds (3, 8, 9, 10, 15, 16, 19 and 22) with the cyclized side chain were firstly identified. Most of the tested compounds possessed cytotoxicity to a certain degree against the two types of cells which implied these oxidized products could play a certain role on anti-cancer functions of the raw materials in vivo. Meanwhile, the results proved that the configurations at C-20 or C-24 and the number of glycosyl at C-3 have important influence on the cytotoxicity. The products 1, 2, 11–17, 20 and 22 should possess great activities and deserved further investigation as potential cytotoxic agents.
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Journal: Steroids - Volume 106, February 2016, Pages 26–34