Synthesis and Evaluation of Saponins with All-Nitrogenated Sugars

Saponins exhibit multiple biological and pharmacological activities, and the sugar moiety of saponins is known to play a crucial role in bioactivity. In this report, we focus on the synthesis and evaluation of saponins with all-nitrogenated sugar (ANS), in which all oxygen atoms are replaced with nitrogen atoms. OSW-1 derivative-, cholesterol-, and diosgenin-ANS glycosides are synthesized by glycosylation with ANS in the presence of TMSOTf. As a result, the OSW-1 mimic, with ANS, exhibits good cytotoxic activity (IC50 = 7.31 mu M) and induces apoptosis.

Automated summary

Saponins have various biological and pharmacological activities, with the sugar moiety playing a crucial role in bioactivity. This report focuses on the synthesis and evaluation of saponins with all-nitrogenated sugar (ANS), where all oxygen atoms are replaced with nitrogen atoms. ANS glycosides of OSW-1 derivative, cholesterol, and diosgenin are synthesized through glycosylation with ANS in the presence of TMSOTf. The OSW-1 mimic with ANS exhibits significant cytotoxic activity (IC50 = 7.31 μM) and induces apoptosis.