Synthesis and Evaluation of Saponins with All-Nitrogenated Sugars

Abstract

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 μM) and induces apoptosis.

Key words

aminosugar - all-nitrogenated sugar - saponins - glycosylation - apoptosis

Publication History

Received: 09 May 2023

Accepted after revision: 05 June 2023

Accepted Manuscript online:
05 June 2023

Article published online:
21 July 2023

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