Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity

Abstract

Diosgenyl saponins, as a type of natural products derived from plants, are the main active component of traditional chinese medicine. Inspiringly, a large number of natural diosgensyl saponins have been shown to exert excellent toxicity to hepatocellular cancer (HCC) cells. In order to better understand the relationship between the structures and their biological effects, a group of diosgenyl saponins (1–4 as natural products and 5 and 6 as their analogs) were efficiently synthesized. The cytotoxic activity of these compounds was evaluated on human hepatocellular carcinoma (HepG2) cells. Structure–activity relationship studies showed that the pentasaccharide or hexasaccharide saponin analogs were relatively less active than their corresponding disaccharide analogue or dioscin. The extension of 4-branched rhamnose moiety on these saponin does not exhibit significant effect on their cytotoxic activity, which disclosed that a certain number and the linkage mode of rhamnose moieties could influence the cytotoxicity of steroid saponins on HepG2 cells.