Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1530-1536.DOI: 10.6023/cjoc201703006 Previous Articles     Next Articles



杨刚强, 李阳, 杨青, 岳馨, 姚雷, 姜永涛   

  1. 烟台大学新型制剂与生物技术药物研究山东省高校协同创新中心 分子药理和药物评价教育部重点实验室(烟台大学) 烟台 264005
  • 收稿日期:2017-03-02 修回日期:2017-04-07 发布日期:2017-05-02
  • 通讯作者: 杨刚强,姜永涛;
  • 基金资助:


Simple and Efficient Synthesis of Pseudoginsenoside HQ

Yang Gangqiang, Li Yang, Yang Qing, Yue Xin, Yao Lei, Jiang Yongtao   

  1. School of Pharmacy, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Yantai University, Yantai 264005
  • Received:2017-03-02 Revised:2017-04-07 Published:2017-05-02
  • Contact: 10.6023/cjoc201703006;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21502164), the Research Fund for Excellent Young and Middle-age Scientists of Shandong Province (No. BS2015YY039), and the Startup Project of Doctor Scientific Research in Yantai University (No. YX14B17).

Pseudoginsenoside HQ[PHQ, 3β-O-β-D-glucopyranosyl-(20S,24S)-epoxydammarane-12β,25-diol] is the main in vivo metabolite of 20(S)-ginsenoside Rh2 which has high biological activities, with potential medicinal value. The reported chemical synthesis of PHQ suffered complex synthetic route and low overall yield because the rational protecting group strategies were required for the key glycosylation on C-3 position of sapogenins. In this paper, the glycosylation conditions on C-3 position of ocotillol type sapogenins were investigated, and it was found that it could realize the selective glycosylation on C-3-position of sapogenins to prepare PHQ under the Ag2CO3 promoter without the protecting group strategy. A new synthesis of PHQ was achieved in three steps via epoxidation, selective glycosylation and debenzoylation reaction of glycon using commercially available 20(S)-protopanoxadiol as the starting material. This method provides a simple and efficient way for the preparation of PHQ and its derivatives.

Key words: pseudoginsenoside HQ, glycosylation, ocotillol type ginsenoside, chemical synthesis