Synlett 2024; 35(04): 427-430
DOI: 10.1055/a-2106-1345
cluster
11th Singapore International Chemistry Conference (SICC-11)

Synthesis and Evaluation of Saponins with All-Nitrogenated Sugars

Ayaha Kage
,
Yuya Okuyama
,
Erina Kato
,
Tomoe Matagawa
,
Sayaka Kawano
,
,
,
,
Takaaki Sato


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.

Supporting Information



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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