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有机化学
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有机化学 ›› 2013, Vol. 33 ›› Issue (12): 2551-2558.DOI: 10.6023/cjoc201307008 上一篇    下一篇

研究论文

柚皮苷半合成E-柚皮素肟类化合物及细胞活性

刘志平a,b, 韦万兴b, 甘春芳a, 黄燕敏a, 刘盛b, 周敏b, 崔建国a   

  1. a 广西师范学院化学与生命科学学院 南宁 530001;
    b 广西大学化学化工学院 南宁 530004
  • 收稿日期:2013-07-05 修回日期:2013-07-30 发布日期:2013-08-16
  • 通讯作者: 韦万兴 E-mail:wxwei@yahoo.com.cn
  • 基金资助:

    国家自然科学基金(No. 81060261)、广西自然科学基金重点(No. 2011jjD20002)和广西师范学院博士点建设开放课题资助项目.

Semisynthesis and Cytotoxicity of E-Naringenin Oximes from Naringin

Liu Zhipinga,b, Wei Wanxingb, Gan Chunfanga, Huang Yanmina, Liu Shengb, Zhou Minb, Cui Jianguoa   

  1. a College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001;
    b College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
  • Received:2013-07-05 Revised:2013-07-30 Published:2013-08-16

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从丰富价廉的天然柚皮苷(Naringin)出发，经水解、选择性甲基化、异戊烯基化分别得到了柚皮素N-1及柚皮素衍生物N-2～N-6. N-1～N-6分别与盐酸羟胺、盐酸甲氧胺、盐酸苄氧胺反应合成了6个E-柚皮素肟N-1a～N-6a和10个E-柚皮素肟醚化合物N-1b～N-6c. 所合成产物通过NMR，HR-ESI-MS方法进行了结构确证；MTT法体外抑制肿瘤增值活性测试显示N-1a，N-1b，N-1c，N-2a，N-4a对胃癌细胞SGC-7901有一定的抑制活性.

关键词: 柚皮苷, 柚皮素, E-柚皮素肟, 半合成, 细胞活性

Naringenin (N-1) and naringenin derivatives N-2～N-6 were synthesized by the hydrolysis, selective methylation or selective O-prenylation using natural naringin as starting material. Six E-naringenin oximes N-1a～N-6a and ten E-naringenin oxime ethers N-1b～N-6c were synthesiszed by reacting N-1～N-6 with hydroxylamine hydrochloride, methoxylamine hydrochloride and benzyloxygen amine hydrochloride, respectively. The structures of the compounds were identified by NMR and HR-ESI-MS. The cytotoxicities of the compounds were evaluated by MTT assay and the results showed that N-1a, N-1b, N-1c, N-2a, N-4a displayed moderate activity against human cancer cell line SGC-7901.

Key words: naringin, naringenin, E-naringenin oximes, semisynthesis, cytotoxicity