A new triterpenoid saponin from Gleditisia sinensis and structure–activity relationships of inhibitory effects on lipopolysaccharide-induced nitric oxide production

Abstract

A phytochemical investigation of the anomalous fruits of Gleditisia sinensis led to one new oleanane-type triterpenoid saponin acylated with one monoterpenic acid, 3-O-β-D-glucopyranosyl oleanolic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2,7-octadienoyl-(1 → 6)]-β-D-glucopyranosyl ester, named gleditsioside Z (1), together with nine known ones (2–10). Their structural details were mainly established on the basis of 1D, 2D NMR and HR–MS analysis as well as some chemical methods. Structure–activity relationships of the isolated saponins that affected nitric oxide production from cultured mouse macrophages (RAW 264.7 cell lines) induced by lipopolysaccharide were discussed.

Keywords:

• Gleditisia sinensis
• Triterpenoid saponins
• Structure–activity relationships

Acknowledgements

This study was partially supported by 2006 Hi-Tech Research Programs (BG2006601), Education Department Blue Project and 333 High-Level Personnel Training of Jiangsu Province.