Semi-Synthesis and Cellular Effects of Three Different Ginsenosides Derived from Re, Rh1, and PPT

Biological and Pharmacological Effects of Synthetic Saponins

“…The roles of carbohydrate in the bioactivity of saponin has been discussed extensively in cytotoxicity assays and can significantly influence the activity. In assays against cancer cells, the existence of carbohydrates showed both positive [58,71,107,108] and negative [37,55,[98][99][100][101] effects. Changing the composition of sugar chains could enhance the cytotoxic effect [14,29,67,70] but also showed no differences in some studies [13,34].…”

“…Although the naturally occurring dammarane-type saponins have been studied for a long time [102], SAR studies revealed that chemically generated synthetic saponins were mainly on ginsenoside derivatives and were still far from satisfactory [103,104]. Based on the recent progress in organic synthesis (Figure 4) [105,106], several studies showed cytotoxicity against cancer cells [58,107,108], as well as antioxidative [59], antiasthma [60] and skin-protective effects [61] of ginsenoside derivatives (Table 1).…”

“…Modifications to the C-20 side chain of the ginsenosides demonstrated that the hydroxylation site and configuration at C-20 and C-24 profoundly influenced cytotoxicity, in which ginsenoside derivatives bearing a monosaccharide at C-3 and a disaccharide at C-6 were more cytotoxic than those without modification [58,107,108]. Another study found that ginsenosides incorporating a Z-configuration at C-20 exhibited higher antioxidative activity than those not, and those bearing a disaccharide moiety at the C-3 position exerted a stronger hemolytic effect [59].…”