Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (4): 639-643.doi: 10.1007/s40242-014-3522-3

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Synthesis and Tumor Cytotoxicity of Novel N-Substituted Glucosamine-bearing Oleanolic Acid Derivatives

REN Li, LIU Yang, YU Guihua, GAO Yuan, LIU Xin, WANG Bo, DENG Xiaonan, CHENG Maosheng   

  1. Key Laboratory of Structure-based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China
  • Online:2014-08-01 Published:2014-05-19
  • Contact: LIU Yang, CHENG Maosheng E-mail:mscheng@syphu.edu.cn;y.liu@syphu.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(Nos.21142010, 81273358) and the PhD Scientific Research Opening Foundation Projects of Liaoning Province of China(No.20091081).

Abstract:

Eleven novel triterpenoid saponins, N-substituted-β-D-glucosaminide derivatives of oleanolic acid, were designed and synthesized via a stepwise glycosylation strategy. These compounds were evaluated for in vitro cytotoxic activity against six different tumor cell lines. Most of the compounds inhibited the growth of, at least, one tumor cell line effectively at micromolar concentrations. Preliminary structure-activity relationships(SARs) indicate that acylation of the nitrogen of the glucosamine-bearing triterpenoid saponins affords the compounds that are highly cytotoxic towards specific tumor cell lines.

Key words: N-Substituted glucosamine-bearing triterpenoid saponin, Tumor cytotoxicity, Oleanolic acid