首都医科大学学报 ›› 2012, Vol. 33 ›› Issue (4): 494-497.doi: 10.3969/j.issn.1006-7795.2012.04.016

• 基础研究 • 上一篇    下一篇

齐墩果酸和去氧胆酸衍生物合成及抗血管生成活性研究

王鹏龙, 程亚涛, 汪林, 徐士勋, 王艳慧, 李强, 雷海民   

  1. 北京中医药大学中药学院中药化学系, 北京 100102
  • 收稿日期:2012-05-08 修回日期:1900-01-01 出版日期:2012-08-21 发布日期:2012-08-21
  • 通讯作者: 雷海民

Synthesis and antiangiogenic activity of oleanolic acid and deoxycholic acid derivatives

WANG Peng-long, CHENG Ya-tao, WANG Lin, XU Shi-xun, WANG Yan-hui, LI Qiang, LEI Hai-min   

  1. Department of Chinese Medicinal Chemistry, School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China
  • Received:2012-05-08 Revised:1900-01-01 Online:2012-08-21 Published:2012-08-21

摘要: 目的 合成齐墩果酸、去氧胆酸-丙酮基衍生物并评价2者对新生血管生成的影响。方法 以丙酮/K2CO3作为反应体系,利用溴代川芎嗪分别与齐墩果酸和去氧胆酸发生亲核取代反应,得到齐墩果酸和去氧胆酸衍生物。采用鸡胚绒毛尿囊膜模型(chorioallantoic membrane,CAM)对其进行在体新生血管活性评价。结果 产物结构经1H-NMR、13C-NMR及IR确证为齐墩果酸乙酰甲酯和和去氧胆酸乙酰甲酯;二者作用于CAM模型后,新生血管的数目均比空白组减少。结论 在丙酮/K2CO3/溴代川芎嗪反应体系中,得到齐墩果酸和去氧胆酸-丙酮基衍生物;经CAM模型测试发现去氧胆酸-丙酮基衍生物对新生血管具有较好抑制活性。

关键词: 齐墩果酸和去氧胆酸-丙酮基衍生物, 鸡胚绒毛尿囊膜模型, 抗血管生成活性

Abstract: Objective Two oleanolic acid and deoxycholic acid-acetonyl derivatives were synthesized; and the angiogenetic activities of the two compounds were aslo evaluated. Methods In the acetone/K2CO3 reaction system, TMP-Br took place nucleophilic substitution reaction with oleanolic acid and deoxycholic acid, respectively. And two novel oleanolic acid and deoxycholic acid-acetonyl derivatives were obtained. The two compounds’ angiogenic activity was evaluated on chick chorioallantoic membrane(CAM) model. Results The oleanolic acid and deoxycholic acid-acetonyl derivatives’ structure were confirmed by 1H-NMR, 13C-NMR and IR spectra. Both of the two compounds could suppress normal angiogenesis in CAM. Conclusion In the acetone/K2CO3/TMP-Br reaction system, we got oleanolic acid and deoxycholic acid-acetonyl derivatives, respectively. Moreover deoxycholic acid-acetonyl derivatives showed well anti-angiogenic activity on CAM assay.

Key words: oleanolic acid-acetonyl and deoxycholic acid-acetonyl derivatives, chorioallantoic membrane, anti-angiogenic activity

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