Citation: Yang Gangqiang, Li Yang, Yang Qing, Yue Xin, Yao Lei, Jiang Yongtao. Simple and Efficient Synthesis of Pseudoginsenoside HQ[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1530-1536. doi: 10.6023/cjoc201703006 shu

Simple and Efficient Synthesis of Pseudoginsenoside HQ

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

Corresponding author: Yang Gangqiang, oceanygq@hotmail.com Jiang Yongtao, yongtao@luye.cn
Received Date: 2 March 2017
Revised Date: 7 April 2017

Fund Project: the National Natural Science Foundation of China 21502164the Research Fund for Excellent Young and Middle-age Scientists of Shandong Province BS2015YY039the Startup Project of Doctor Scientific Research in Yantai University YX14B17

Figures(4)

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.
- pseudoginsenoside HQ,
- glycosylation,
- ocotillol type ginsenoside,
- chemical synthesis
1. [1]
2. [2]
  Zhang, J. W.; Zhou, F.; Wu, X. L.; Zhang, X. X.; Chen, Y. C.; Zha, B. S.; Niu, F.; Lu, M.; Hao, G.; Sun, Y.; Sun, J. G.; Peng, Y.; Wang, G. J. Br. J. Pharmacol. 2012, 165, 120. doi: 10.1111/j.1476-5381.2011.01505.x
3. [3]
  Yang, J. Ph.D. Dissertation, Jilin University, Changchun, 2016 (in Chinese)
4. [4]
  Li, L.; Chen, X. Y.; Zhou, J. L.; Zhong, D. F. Drug Metab. Dispos. 2012, 40, 2041. doi: 10.1124/dmd.112.046995
5. [5]
  Yang, J.; Li, X. W.; Sun, T.; Gao, Y.; Chen, Y. X.; Jin, Y. R.; Li, Y. Steroids 2016, 106, 26. doi: 10.1016/j.steroids.2015.12.005
6. [6]
  Liu, J. Ph.D. Dissertation, Shenyang Pharmaceutical University, Shenyang, 2016 (in Chinese).
7. [7]
  Shen, R. Z.; Xin, C.; Laval, S.; Sun, J. S.; Yu, B. J. Org. Chem. 2016, 81, 10279. doi: 10.1021/acs.joc.6b01265
8. [8]
  Yang, N.; Yang, S. L.; Zhao, Y. Q. Drugs Clinic 2014, 29, 574 (in Chinese)
9. [9]
  Liao, J. X.; Sun, J. S.; Niu, Y. M.; Yu, B. Tetrahedron Lett. 2011, 52, 3075. doi: 10.1016/j.tetlet.2011.04.003
10. [10]
  (a) Atopkina, L. N. Uvarova, N. I. Chem. Nat. Compd. 1981, 17, 254.
  (b) Samoshina, N. F.; Novikov, V. L.; Denisenko, V. A.; Uvarova, N. I. Chem. Nat. Compd. 1983, 19, 299.
  (c) Atopkina, L. N.; Novikov, V. L.; Denisenko, V. A.; Uvarova, N. I. Chem. Nat. Compd. 1985, 21, 674.
  (d) Atopkina, L. N.; Uvarova, N. I. Chem. Nat. Compd. 1986, 22, 421.
  (e) Atopkina, L. N.; Samoshina, N. F.; Denisenko, V. A.; Pokhilo, N. D.; Uvarova, N. I. Chem. Nat. Compd. 1986, 22, 415.
11. [11]
  (a) Yosioka, I.; Yamauchi, H.; Kitagawa, I. Chem. Pharm. Bull. 1972, 20, 502.
  (b) Appendino, G.; Gariboldi, P.; Wollenweber, E. Sironi, A.; Molinari, H. Phytochemistry 1992, 31, 923.
  (c) Bi, Y.; Tian, J. W.; Wang, L.; Zhao, F. L.; Zhang, J. F.; Wang, N.; Sun, H. J.; Meng, Q. G. J. Med. Plant. Res. 2011, 5, 2424.
  (d) Li, L.; Chen, X. Y.; Li, D.; Zhong, D. F. Drug Metab. Dispos. 2011, 39, 472.
12. [12]
  Ren Y. Y. M.S. Thesis, Jilin University, Changchun, 2012 (in Chinese).
13. [13]
  Meng, Q. G.; Tan, W. J.; Hou, G. G.; Zhang, X. Y.; Hu, X. Y.; Yang, F.; Bai, G. J.; Zhu, W. W.; Cai, Y.; Bi, Y. J. Mol. Struct. 2013, 1054–1055, 1.
14. [14]
  Ueda, M.; Yang, G. Q.; Ishimaru, Y.; Itabashi, T.; Tamura, S.; Kiyota, H.; Kuwahara, S.; Inomata, S.; Shoji, M.; Sugai, T. Bioorg. Med. Chem. 2012, 20, 5832. doi: 10.1016/j.bmc.2012.08.003
15. [15]
  Li, Y.; Yang, X. Y.; Liu, Y. P.; Zhun, C. S.; Yang, Y.; Yu, B. Chem.-Eur. J. 2010, 16, 1871. doi: 10.1002/chem.v16:6
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