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2013 , Vol. 33 >Issue 12: 2551 - 2558

DOI: https://doi.org/10.6023/cjoc201307008

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 ,
  • 韦万兴 ,
  • 甘春芳 ,
  • 黄燕敏 ,
  • 刘盛 ,
  • 周敏 ,
  • 崔建国
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  • 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

  网络出版日期: 2013-08-16

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.

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Semisynthesis and Cytotoxicity of E-Naringenin Oximes from Naringin

  • Liu Zhiping ,
  • Wei Wanxing ,
  • Gan Chunfang ,
  • Huang Yanmin ,
  • Liu Sheng ,
  • Zhou Min ,
  • Cui Jianguo
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  • 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 date: 2013-07-05

  Revised date: 2013-07-30

  Online published: 2013-08-16

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摘要

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

本文引用格式

刘志平 , 韦万兴 , 甘春芳 , 黄燕敏 , 刘盛 , 周敏 , 崔建国 . 柚皮苷半合成E-柚皮素肟类化合物及细胞活性[J]. 有机化学, 2013 , 33(12) : 2551 -2558 . DOI: 10.6023/cjoc201307008

Abstract

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

参考文献

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