Synthesis and Solubility of Hydrophilic Derivatives of ${\beta}$- Sitosterol

Chung, Dae-Won;Choi, Young-Tai

  • Published : 20070500

Abstract

In this study, hydrophilic derivatives of β-sitosterol, which is known to have potential to reduce blood cholesterol levels, were synthesized by the esterification of poly(ethylene glycol) (PEG) and β-sitosterol with carboxylic functionality in the presence of dehydrating agents and a basic catalyst. By adjusting the molar ratios of reactants in the esterification reaction, hydrophilic β-sitosterol derivatives (HPSs) with various degrees of substitution (DS, average molar number of β-sitosterol moieties per molecule of HPS) were synthesized. The chemical structure and the distribution of isomers in HPSs were characterized by 1H-NMR spectroscopy and MALDI-TOF mass spectrometry, respectively. The solubility of HPS in water was significantly affected by the value of DS of HPS.

Keywords

References

  1. H. T. Vanhanen and T. A. Miettinen, Clin. Chim. Acta, 205, 97 (1992)
  2. H. Gylling and T. A. Miettinen, J. Lipid Res., 37, 1776 (1996)
  3. P. J. H. Jones, D. E. MacDougall, F. Ntanios, and C. A. Vanstone, Can. J. Physiol. Pharmacol., 75, 217 (1997)
  4. U. S. Patent 6,184,397 (2001)
  5. F. H. Mattson, R. A. Volpenhein, and J. B. Martin, J. Lipid Res., 5, 374 (1964)
  6. K. G. Pinter, J. G. Hamilton, and J. E. Muldrey, J. Lipid Res., 5, 273 (1964)
  7. D.-W. Chung and Y. T. Cho, J. Korean Ind. Eng. Chem., 17, 375 (2006)
  8. U. S. Patent 6,660,491 (2003)
  9. P. J. H. Jones, D. E. MacDougall, F. Ntanios, and C. A. Vanstone, Can, J. Pharmacol., 75, 217 (1997)
  10. U. S. Patent 5,502,045 (1996)
  11. J. A. Weststrate and G. W. Meijer, Eur. J. Clin. Nutr., 52, 334 (1998)
  12. U. S. Patent 5,215,759 (1993)
  13. W.-X. Ding, X.-R. Qi, P. Li, Y. Maitani, and T. Nagai, Int. J. Pharm., 300, 38 (2005)
  14. Y. G. Skornick, G. H. Rong, W. F. Sindelar, L. Richert, J. M. Klausner, R. R. Rozin, and M. Shinitzky, Cancer, 58, 650 (1986)
  15. X.-B. Yuan, H. Li, and Y.-B. Yuan, Carbohydr. Polym., 65, 337 (2006)
  16. R. W. Kuhn, W. T. Schrader, R. G. Smith, and B. W. O'Malley, J. Biol. Chem., 250, 4220 (1975)
  17. C. J. Pouchert and J. Behnke, The Aldrich Library of $^{13} C$ and $^{1} H$FT NMR Spectra, Aldrich Chemical Company, Inc. (1993)
  18. S. P. Mun, E. M. Hassan, and T. H. Yoon, J. Korean Ind. Eng. Chem., 7, 430 (2001)
  19. S. P. Mun, I. A. Gilmour, and P. J. Jordan, J. Ind. Eng. Chem., 12, 720 (2006)
  20. S. B. Lee, K. A. Park, and I. K. Hong, J. Korean Ind. Eng. Chem., 10, 438 (1999)
  21. L. A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester (1995)