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2β-羟基熊果酸的合成及其抗肿瘤活性

黄丽荣1,2,陈磊2,杨小生1,2*,马琳2,张建新2,王道平2   

  1. (1.贵州大学精细化工研究开发中心教育部绿色农药与农业生物工程重点实验室 贵阳 550025；
    2.中国科学院天然产物化学重点实验室 贵阳 550002)
  • 收稿日期:2012-12-03 修回日期:2013-01-11 出版日期:2013-10-10 发布日期:2013-10-10
  • 通讯作者: 杨小生，研究员; Tel:0851-3806465; Fax:0851-3805081; E-mail:gzcnp@yahoo.com.cn; 研究方向：天然产物的结构修饰及全合成
  • 基金资助:
    国家自然科学基金(30973620)贵州省科技厅基金（黔科合J字[2011]2310号）资助项目

Synthesis and Antitumor Activity of 2β-Hydroxyursolic Acid

HUANG Lirong1,2, CHEN Lei2, YANG Xiaosheng1,2*, MA Lin2, ZHANG Jianxin2, WANG Daoping2   

  1. (1.Ministry of Education Key Laboratory of Green Pesticide and Ago-Bioengineering,Center for
    Research and Development of Fine Chemicals of Guizhou University,Guiyang 550025,China;
    2.The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences,Guiyang 550002,China)
  • Received:2012-12-03 Revised:2013-01-11 Published:2013-10-10 Online:2013-10-10
  • Contact: xiao

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摘要： 以熊果酸为原料，经C-3羟基氧化、C-28羧基苄酯化保护、C-2乙酰化及水解、还原、脱保护得到2β-羟基熊果酸，6步反应的总收率为60.1%。 中间体及目标化合物结构经IR、1H NMR、13C NMR和MS测试技术确证。 以噻唑蓝(MTT)比色法检测2β-羟基熊果酸对人白血病细胞K562及人肺癌细胞A549肿瘤细胞的体外抑制活性，结果表明，对2种肿瘤细胞的生长均表现出一定的抑制作用。

关键词: 熊果酸, 2&, beta, -羟基熊果酸, 合成, 体外肿瘤细胞抑制活性

Abstract: Using ursolic acid as the precursor, 2β-hydroxyursolic acid was synthesized by 6-step successive reactions including oxidation, benzylation, acetylation, hydrolysis, reduction, and group deprotection reactions. The overall yield is 60.1%. Its structure was determined by IR, 1H NMR, 13C NMR and MS. The antitumor activity of the target compound was evaluated against the proliferation of human leukemia cell K562 and human lung carcinoma cell A549 by the MTT assay. The results indicate that the target compound has inhibitive activity toward cell growth for the two tumor cells.

Key words: ursolic acid, 2&, beta, -hydroxyursolic acid, synthesis, inhibition activity to tumor cell

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