Citation: KAI Guiqing, LIU Liu, WANG Huanming. Separation mechanism of oleanane and ursane pentacyclic triterpenoid isomers by coordination chromatography[J]. Chinese Journal of Chromatography, ;2014, 32(3): 235-241. doi: 10.3724/SP.J.1123.2013.09015 shu

Separation mechanism of oleanane and ursane pentacyclic triterpenoid isomers by coordination chromatography

1.
1. School of Life Science, Anhui University, Hefei 230601, China;

Corresponding author: KAI Guiqing,
Received Date: 11 September 2013
Available Online: 11 December 2013

This paper focuses on the study of the separation mechanism of oleanane and ursane pentacyclic triterpenoid isomers by a coordination chromatographic method. Based on the calculation analysis,β-cyclodextrin (β-CD) and its derivatives were selected as the suitable agents. The experimental results showed that the resolution of madecassoside isomers with the addition of glucosyl-β-cyclodextrin (Glu-β-CD) to the mobile phase (11.95) was higher than that of the addition of β-CD (9.61) or dimethyl-β-cyclodextrin (DM-β-CD) (9.89). The formation of 1:1 inclusion complexes was assumed. The apparent formation constants (K_F) of pentacyclic triterpenes with β-CD were determined by HPLC method. For asiaticoside-B, the K_F value with the addition of Glu-β-CD (2534 L/mol) was larger than that with the addition of β-CD (1467 L/mol) or DM-β-CD (1373 L/mol). According to the infrared characteristic absorbing peaks and simulation, the methyl part of asiaticoside-B might enter into β-CD cavity while the carbonyl group of asiaticoside-B might not enter into the cavity of β-CD, and the large glycoside parts were kept outside, forming hydrogen-bond interaction with the exterior of β-CD cavity. The results of the separation of oleanane and ursane pentacyclic triterpenoid isomers by coordination chromatography indicated that, the separation mechanism might be attributed to the steric differences (the place of methyl group in E cyclic), which lead to different chromatographic behaviors.
- high performance liquid chromatography (HPLC),
- madecassoside,
- asiaticoside-B,
- isomeric compound,
- cyclodextrin
1. [1]
  [1] Zhang M F, Shen Y Q. Anti-Infection Pharmacy, 2012, 9: 13
2. [2]
  [2] Jana U, Sur T K, Maity L N, et al. Nepal Med Coll J, 2010, 12: 8
3. [3]
  [3] Aree W, Mayuree H T, Boonyong T, et al. J Ethnopharmacol, 2012, 143: 579
4. [4]
  [4] Hu C P, Chen L S, Xin Y, et al. Chinese Journal of Chromatography, 2006, 24(5): 492
5. [5]
  [5] Tan Q, Shou Q Y, Zhang S, et al. Chinese Journal of Chromatography, 2010, 28(12): 1150
6. [6]
  [6] Xiao C Z, Sheng H W. J Chromatogr B, 2009, 877: 477
7. [7]
  [7] Ha J K, Jae H P, Gyu T K. Microchem J, 2011, 98: 115
8. [8]
  [8] Rhourrhi-Friha B, Westa C, Pasquierb L, et al. J Chromatogr A, 2012, 1256: 177
9. [9]
  [9] Xie Y F, Yang Y Y, Liu J J, et al. Chinese Journal of Chromatography, 2013, 31(7): 679
10. [10]
  [10] Chi Y M, Zhang Y, Wang Q X, et al. Chinese Journal of Chromatography, 2013, 31(9): 838
11. [11]
  [11] Lesellier E, Destandau E, Grigoras C, et al. J Chromatogr A, 2012, 1268: 157
12. [12]
  [12] Li Z H, Tang G L, Pang Y Q, et al. Chinese Journal of Chromatography, 2010, 28(8): 790
13. [13]
  [13] Silvia A C, Stefano M. J Pharm Biomed Anal, 2012, 70: 647
14. [14]
  [14] Gao M Z, Yuan X Y, Xiao H B, et al. Chinese Journal of Chromatography, 2008, 26(3): 362
15. [15]
  [15] Pan J, Kai G Q, Yuan C X, et al. Chinese Journal of Chromatography, 2007, 25(3): 316
16. [16]
  [16] Kai G Q, Pan J. Bull Korean Chem Soc, 2008, 29: 551
17. [17]
  [17] Pan J, Kai G Q, Yuan C X, et al. Chromatographia, 2007, 66: 121
18. [18]
  [18] Yan L, Gong P, Yuan L, et al. Chinese Journal of Chromatography, 2007, 25(3): 337
19. [19]
  [19] Xu X H, Su Q, Zang Z H. Journal of Pharmaceutical Analysis, 2012, 2: 238
20. [20]
  [20] Zhang Y. Chinese Journal of Chromatography, 2014, 32(1): 47
21. [21]
  [21] Claude B, Morina P, Lafossea M, et al. J Chromatogr A, 2004, 1049: 37
22. [22]
  [22] Fujimura K, Ueda T, Kitagawa M. Anal Chem, 1986, 58: 2668
23. [23]
  [23] Clarot I, Clédat D, Battu S, et al. J Chromatogr A, 2000, 903: 67
24. [24]
  [24] Ravelet C, Geze A, Villet A, et al. J Pharm Biomed Anal, 2002, 29: 425
25. [25]
  [25] Moeder C, O'Brien T, Thompson R, et al. J Chromatogr A, 1996, 736: 1
26. [26]
  [26] Gazpio C, Sánchez M, García-Zubiri I X, et al. J Pharm Biomed Anal, 2005, 37: 487
27. [27]
  [27] Bielejewska A, Duszczyk K, Sybilska D. J Chromatogr A, 2001, 931: 81
28. [28]
  [28] Mohseni R M, Hurtubise R J. J Chromatogr A, 1990, 499: 395
29. [29]
  [29] Schneiderman E, Stalcup A M. J Chromatogr B, 2000, 745: 83
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沈阳化工大学材料科学与工程学院沈阳 110142