高等学校化学学报

高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (2): 346.doi: 10.7503/cjcu20120972

• 有机化学 • 上一篇    下一篇

β-D-吡喃型葡萄糖酚苷类天然类似物的合成及抗HCV病毒活性

韩文霞, 朱华结   

  1. 中国科学院昆明植物研究所, 植物化学与西部植物资源持续利用国家重点实验室, 昆明 650204
  • 收稿日期:2012-08-18 出版日期:2013-02-10 发布日期:2013-01-21
  • 通讯作者: 朱华结,男,博士,教授,主要从事天然有机合成与计算化学研究.E-mail:zhuhuajie@hotmail.com. E-mail:zhuhuajie@hotmail.com
  • 基金资助:

    国家自然科学基金(批准号: 30873141)和国家"九七三"计划项目(批准号: 2009CB522300)资助.

Synthesis and Anti-HCV Activity of Analogues of the Natural Phenolic β-D-Glucopyranosides

HAN Wen-Xia, ZHU Hua-Jie   

  1. State Key Laboratory of Phytochemistry and Plant Reasources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China
  • Received:2012-08-18 Online:2013-02-10 Published:2013-01-21
  • Contact: Hua-Jie Zhu E-mail:zhuhuajie@hotmail.com

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摘要：

以α-溴代四乙酰基葡萄糖(或β-D-葡萄糖五乙酸酯)和酚为原料, 经2步反应合成了15个新的β-D-吡喃型葡萄糖酚苷类天然产物类似物, 采用质谱(MS)及核磁共振(NMR)等手段对其结构进行了表征. 生物活性测定结果表明, 化合物8a和10a对丙型肝炎病毒(HCV)有一定的抑制作用, 它们的EC50值分别为21和9.4 μmol/L, CC50值分别为150.4和145.9 μmol/L.

关键词: 酚苷, 1,2-反式糖苷化, 抗HCV病毒活性

Abstract:

Phenolic β-D-glucopyranosides exist widely in nature and exhibit many important physiological activities. For example, gastrodia isolated from Pholidota chinensis Lind1. has such a sketch and play an important bioactivity on nerve system. Recently, we found another phenolic β-D-glucopyranoside from the Pulicaria insignis which had definite anti-HCV activity. Based on the results achieved in our research group, we tried to design and synthesize series of phenolic β-D-glucopyranosides to wish to find new and better bioactive compounds used in anti-HCV study. Fifteen novel natural analogues of phenolic β-D-glucopyranosides were synthesized from phenolic aglycones and acetobromo-α-D-glucose or β-D-glucose pentaacetate. Their structures were characterized by MS, 1H NMR and 13C NMR. Preliminary anti-HCV activity tests showed that compounds 8a and 10a exhibited definite anti-viral activity, their EC50 are 21 and 9.4 μmol/L, and the CC50 of them are 150.4 and 145.9 μmol/L, respectively.

Key words: β-D-Glucoside, Phenolic glycoside, Anti-HCV activity

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