有机化学 ›› 2012, Vol. 32 ›› Issue (01): 138-144.DOI: 10.6023/cjoc1104084 上一篇    下一篇

研究论文

11-脱氧甘草次酸乙酯3-单糖链皂苷的合成及其活性研究

王军a,b, 文伟河b, 胡小丽b, 朱玉亮b   

  1. a 江苏警官学院公安科技系 南京 210012;
    b 南京工业大学生物与制药工程学院 南京 210009
  • 收稿日期:2011-04-08 修回日期:2011-08-05 发布日期:2012-01-28
  • 通讯作者: 王军 E-mail:kwangjun@163.com

Synthesis and Activity of 11-Deoxoglycyrrhetinic Acid 3-Monodesmosides

Wang Juna,b, Wen Weiheb, Hu Xiaolib, Zhu Yuliangb   

  1. a Department of Forensic Science, Jiangsu Police Institute, Nanjing 210012;
    b College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009
  • Received:2011-04-08 Revised:2011-08-05 Published:2012-01-28
  • Contact: Wang Jun E-mail:kwangjun@163.com

合成了5 种11-脱氧甘草次酸3-单糖链皂苷并初步探讨其生物活性. 以苯甲酰基保护的糖基三氯乙酰亚胺酯为供体, 在三氟甲磺酸三甲基硅脂(TMSOTf)的催化作用下与11-脱氧甘草次酸乙酯C(3)位羟基发生糖苷化反应, 以较好的产率制备得苯甲酰基保护的11-脱氧甘草次酸乙酯3-单糖链皂苷7a7e, 用NaOMe/MeOH 溶液脱除苯甲酰基得11-脱氧甘草次酸乙酯3-单糖链皂苷8a8e. 合成的5 个11-脱氧甘草次酸3-单糖链皂苷均为新化合物, 结构经1H NMR、质谱、元素分析确证, 活性实验表明化合物8a 对高浓度N,N-二甲基甲酰胺(DMF)中枯草芽孢杆菌的生长具有保护作用,化合物8e 对高浓度DMF 中大肠杆菌、酵母菌的生长具有保护作用.

关键词: 11-脱氧甘草次酸乙酯, 糖苷化, 合成

Five 11-deoxoglycyrrhetinic acid 3-monodesmosides were synthesized and the bacteriostatic activities were studied. Before the glycosylation, benzoyl glycoyl trichloroacetimidates were synthesized as donors, then, 3-OH of acetyl 11-deoxoglycyrrhetinate was coupled as glycosyl-receptors with the donors through glycosylation method at the promotion of trimethylsilyl trifluoromethanesulphonate (TMSOTf) to afford 5 benzoyl glycosyl derivatives of acetyl 11-deoxoglycyrrhetinate 7a7e. Deprotection of the derivatives afforded acetyl 11-deoxoglycyrrhetinate 3-monodesmoside 8a8e. The structures all compounds were characterized by 1H NMR, MS and Ultimate analysis. The preliminary pharmacological research showed that compound 8a could protect the growth of E. col while 8e could protect the growth of Bacillus subtilis and yeast at high level of N,N-dimethylformamide (DMF).

Key words: acetyl 11-deoxoglycyrrhetinate, glycosylation, synthesis