A new triterpenoid saponin from Gleditisia sinensis and structure-activity relationships of inhibitory effects on lipopolysaccharide-induced nitric oxide production.
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-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2,7-octadienoyl-(1 --> 6)]-beta-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.
Gao
Zheng-Zhen
ZZ
Department of Chinese Materia Medica Analysis, China Pharmaceutical University, Nanjing, 210038 Jiangsu, China.
Xia
Yu-Feng
YF
Yao
Xiu-Juan
XJ
Dai
Yue
Y
Wang
Qiang
Q
D000818:Animals; D002460:Cell Line; D031501:Gleditsia / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis*; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry*
D008070:Lipopolysaccharides; D012503:Saponins; D014315:Triterpenes; C082161:lipopolysaccharide A; D009569:Nitric Oxide