应用化学

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橙皮素席夫碱类衍生物的合成及抗氧化作用

段志芳,张少平,付莉,李充璧*   

  1. (肇庆学院生命科学学院,生物医药工程中心 肇庆 526061)
  • 收稿日期:2013-07-10 修回日期:2013-09-18 出版日期:2014-05-10 发布日期:2014-05-10
  • 通讯作者: 李充璧,教授; Tel/Fax:0758-2752538; E-mail:lcb@zqu.edu.cn; 研究方向:天然药物开发
  • 基金资助:
    广东省科学技术厅基金项目(2011101),肇庆市科技创新计划项目(2012G25)

Synthesis and Antioxidant Activities of Hesperitin Schiff Base Derivatives

DUAN Zhifang, ZHANG Shaoping, FU Li, LI Chongbi*   

  1. (College of Life Science,Biopharmaceutical Research and Development Center,Zhaoqing University,Zhaoqing 526061,China)
  • Received:2013-07-10 Revised:2013-09-18 Published:2014-05-10 Online:2014-05-10
  • Contact: li

摘要: 从中药陈皮中提取橙皮苷,通过酸水解制备橙皮素,再分别与苯肼类、苯甲酰肼类、苯氨基脲类、苯氨基硫脲类、苯乙酰肼类、苯氧乙酰肼类和苯氨基乙酰肼类化合物缩合得到相应的橙皮素席夫碱类化合物。 用紫外、红外、核磁共振氢谱、质谱及元素分析等技术手段对化合物的结构进行了表征。 测定并比较了橙皮苷、橙皮素及其席夫碱新化合物清除超氧自由基(O-·2)、羟自由基(·OH)和2,2-二苯基-1-苦味酰基自由基(DPPH·)的活性及总还原能力。 结果表明,在1.0 g/L时,这些化合物均具有抗氧化活性,其中部分橙皮素席夫碱化合作用强于橙皮苷和橙皮素。

关键词: 橙皮苷, 橙皮素, 席夫碱, 合成, 抗氧化

Abstract: Hesperidin was extracted from citrus peels. Hesperetin was then prepared by acid-catalyed hydrolysis reaction of hesperidin. Eighteen hesperitin Schiff base derivatives were synthesized by the condensation reaction of hesperetin with amino compounds. These compounds were characterized by UV, IR, 1H NMR, MS and elemental analysis. The scavenging effects of hesperidin, hesperitin and these Schiff base compounds on the superoxide radical(O-·2), hydroxyl radical(·OH) and 2,2-diphenyl-1-picrylhydrazyl radical(DPPH·) and their total reduction activities were also compared. The results show that all of the Schiff bases used herein have scavenging effects on these radicals, and some hydrazones derivatives have stronger effect than hesperidin and hesperitin at the concentration of 1.0 g/L.

Key words: hesperidin, hesperitin, Schiff bases, synthesis, antioxidation

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