Ion-Exchange Chromatography of Bile Acids

  • A. Kuksis


The common bile acids and their glycine and taurine conjugates are relatively freely soluble in aqueous solutions and possess dissociation constants that range from near neutrality to values exhibited by the strongest of organic acids. Ion-exchange chromatography should therefore be theoretically suitable for an efficient separation of such molecules. In practice, however, the adaptation of ion-exchange techniques to bile acid work has been limited and progress extremely slow. This has been partly due to the great success of the thin-layer and gas-liquid chromatographic techniques as means of analysis of bile acids, as well as to the discovery of extremely selective solvent pairs for the separate extraction of the glycine and taurine conjugates from natural sources. The main difficulty has been the complex behavior of these natural detergents in aqueous solutions. The realized separations apparently have involved certain sorbent properties of the ion exchangers as well as chromatography of ions by ion exchange.


Bile Acid Lithocholic Acid Bile Acid Conjugate Fecal Bile Acid Glycine Conjugate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    D. Kritchevsky and P. P. Nair, in “The Bile Acids” (D. Kritchevsky and P. P. Nair, eds.), Vol. 1, Chapter 1, Plenum Press, New York (1971).Google Scholar
  2. 2.
    B. A. Gordon, A. Kuksis, and J. M. R. Beveridge, Can. J. Biochem. Physiol. 41, 77 (1963).PubMedCrossRefGoogle Scholar
  3. L. Peric-Golia and R. S. Jones, Science 142, 245 (1963).PubMedCrossRefGoogle Scholar
  4. 4.
    R. H. Palmer, Proc. Natl. Acad. Sci. U.S.A. 58, 1047 (1967).PubMedCrossRefGoogle Scholar
  5. 5.
    D. M. Small, in “The Bile Acids” (P. P. Nair and D. Kritchevsky, eds.), Vol. 1, Chapter 8, Plenum Press, New York (1971).Google Scholar
  6. 6.
    A. F. Hofmann and D. M. Small, Ann. Revs. Med. 18, 333 (1967).CrossRefGoogle Scholar
  7. 7.
    B. A. Josephson, Biochem. Z. 263, 428 (1933).Google Scholar
  8. 8.
    W. D. Kumler and I. F. Halverstadt, J. Biol. Chem. 137, 765 (1941)Google Scholar
  9. 9.
    P. Ekwall, T. Rosendahi, and N. Lofman, Acta Chem. Scand. 11, 590 (1957).CrossRefGoogle Scholar
  10. 10.
    O. M. Henriques, Acta Pathol. Microbiol. Scand. Suppl. 111, 149 (1930).Google Scholar
  11. 11.
    F. Helfferich, “Ion Exchange,” McGraw-Hill, New York (1962).Google Scholar
  12. 12.
    C. J. O. R. Morris and P. Morris, “Separation Methods in Biochemistry,” Chapters 8, 9, and 10, Pitman, London (1963).Google Scholar
  13. 13.
    F. Helfferich, in “Advances in Chromatograph,” (J. Calvin Giddings and R. A. Keller, eds.), Vol. 1, Chapter 1, Marcel Dekker, New York (1965).Google Scholar
  14. 14.
    Dowex-lon Exchange,“ Second Ed., Dow Chemical Company, Midland, Michigan (1959)Google Scholar
  15. 15.
    D. F. Zinkel and J. W. Rowe, Ana! Chem. 36, 1160 (1964).CrossRefGoogle Scholar
  16. 16.
    B. A. Gordon, “The Analysis of Bile Acid Conjugates by Ion Exchange Chromatography,” M.Sc. thesis, Queen’s University, Kingston, Canada (1961).Google Scholar
  17. 17.
    K. Randerath, “Thin Layer Chromatography” (Translated by D. D. Libman), Second Ed., Academic Press, New York (1966).Google Scholar
  18. 18.
    J. Blanchard, “A Study of [on Exchange Resins and Certain Bile Acids, M.Sc thesis, University of Toronto, Toronto, Canada (1966).Google Scholar
  19. 19.
    J. Blanchard and J. G. Nairn, J. Phys. Chem. 72, 1204 (1968).PubMedCrossRefGoogle Scholar
  20. 20.
    D. H. Sandberg, J. Sjövall, K. Sjövall, and D. A.Turner, J. Lipid Res. 6, 182 (1965).PubMedGoogle Scholar
  21. 21.
    B. A. Gordon, A. Kuksis, and J. M. R. Beveridge, Can. J. Biochem. 42, 897 (1964).PubMedCrossRefGoogle Scholar
  22. 22.
    D. M. Tcnnent, H. Siegel, M. E. Zanetti, G. W. Kuron, W. H. Ott, and F. J. Wolf, J. Lipid Res. 1, 469 (1960).Google Scholar
  23. 23.
    D. M. Tennent, S. A. Hashim, and T. B. Van Itallie, Fed. Proc. 21 (Suppl. 11), 77 (1962).PubMedGoogle Scholar
  24. 24.
    C. H. Whiteside, H. B. Fluckiger, and H. P. Sarett, Proc. Soc. Exptl. Biol. Med. 121, 153 (1966).CrossRefGoogle Scholar
  25. 25.
    W. E. Cohn, J. Am. Chem. Soc. 72, 1471 (1950).CrossRefGoogle Scholar
  26. 26.
    C. W. Davies, Biochem. J. 45, 38 (1949).PubMedGoogle Scholar
  27. 27.
    G. W. Bodamer and R. Kunin, Indust. Engng. Chem. (Industr.) 45, 2577 (1953).CrossRefGoogle Scholar
  28. 28.
    C. W. Davies and B. D. R. Owen, J. Chem. Soc. 1956, 1676.Google Scholar
  29. 29.
    C. W. Davies and B. D. R. Owen, J. Chem. Soc. 1956, 1681.Google Scholar
  30. 30.
    G. W. Kuron and D. M. Tennent, Fed. Proc. 20, 268 (1961).Google Scholar
  31. 31.
    A Kuksis, unpublished results.Google Scholar
  32. 32.
    B. A. Gordon, A. Kuksis, and J. M. R. Beveridge, Fed. Proc. 20, 248 (1961).Google Scholar
  33. 33.
    J. Sjövall, in “Methods of Biochemical Analysis” (D. Glick, ed.), Vol. 12, page 97, Wiley, New York (1964).Google Scholar
  34. 34.
    G. Rouser, G. Kritchevsky, D. Heller, and E. Lieber, J. Am. Oil Chemists’ Soc. 40, 425 (1963).CrossRefGoogle Scholar
  35. 35.
    E. Hogfeldt, in “Ion Exchange” (J. A. Marinsky, ed.), Vol. 1, Chapter 4, Marcel Dekker, New York (1966).Google Scholar
  36. 36.
    A. F. Hofmann, J. Lipid Res. 8, 55 (1967).PubMedGoogle Scholar
  37. 37.
    R. M. Smillie, Arch. Biochem. Biophys. 85, 557 (1959).PubMedCrossRefGoogle Scholar
  38. 38.
    B. A. Gordon, unpublished results.Google Scholar
  39. 39.
    M. T. Subbiah and A. Kuksis, manuscript in preparation.Google Scholar
  40. 40.
    T. Briggs, M. W. Whitehouse, and E. Staple, Nature 182, 394 (1958).PubMedCrossRefGoogle Scholar
  41. 41.
    G. Biserte, J. Vanlerenberghe, and F. Guerrin, Compt. Rend. Soc. Bio/., 153, 618 (1959).Google Scholar
  42. 42.
    A. Norman, Proc. Soc. Exptl. Biol. Med. 115, 936 (1964).CrossRefGoogle Scholar
  43. 43.
    H. Shimura, Hirosaki Igaku 8, 483 (1957); in C. A. 52, 3269g (1958).Google Scholar
  44. 44.
    A. Norman, Proc. Soc. Exptl. Biol. Med. 116, 902 (1964).CrossRefGoogle Scholar
  45. 45.
    H. P. Gregor, G. K. Hoeschele, J. Potenza, A. G. Tsuk, R. Feinland, M. Shoda, and P. Teyssie, J. Am. Chem. Soc. 87, 5525 (1965).CrossRefGoogle Scholar
  46. 46.
    M. Lambiotte, Bull. Soc. Chim. Biol. 37, 1023 (1955).PubMedGoogle Scholar
  47. 47.
    O. A. Roels and S. A. Hashim, Fed. Proc. 21 (Suppl. 11), 71 (1962).PubMedGoogle Scholar
  48. 48.
    S. S. Ali and A. Kuksis, unpublished results.Google Scholar
  49. 49.
    I. Hornstein, J. A. Alford, L. E. Elliott, and P. F. Crowe, Anal. Chem. 32, 540 (1960).CrossRefGoogle Scholar
  50. 50.
    S. S. Ali, A. Kuksis, and J. M. R. Beveridge, Can. J. Biochem. 44, 957 (1966).PubMedCrossRefGoogle Scholar
  51. 51.
    K. Sjövall and J. Sjövall, Clin. Chim. Acta 13, 207 (1966).PubMedCrossRefGoogle Scholar
  52. 52.
    T. Okishio, P. P. Nair, and M. Gordon, Biochem. J. 102, 654 (1967).PubMedGoogle Scholar
  53. 53.
    P. P. Nair, M. Gordon, S. A. Tepper, and D. Kritchevsky, J. Biol. Chem. 243, 4034, (1968).PubMedGoogle Scholar
  54. 54.
    M. Lambiotte, Rev. Intern. Hepatol. 7, 521 (1957).Google Scholar
  55. 55.
    B. A. Gordon, “Studies on Bile Acid Metabolism,” Ph.D. thesis, Queen’s University, Kingston, Canada (1963).Google Scholar
  56. 56.
    R. R. Redfield, Biochim. Biophys. Acta 10, 344 (1953).PubMedCrossRefGoogle Scholar
  57. 57.
    L. Peric-Golia and R. S. Jones, Proc. Soc. Exptl. Biot Med. 110, 327 (1962).CrossRefGoogle Scholar
  58. 58.
    S. S. Bergen, Jr., T. B. Van Itallie, D. M. Tennent, and W. H. Sebrell, Proc. Soc. Exptl. Biol. Med. 102, 676 (1959).CrossRefGoogle Scholar
  59. 59.
    T. B. Van Itallie and S. A. Hashim, Med. Clin. N. Amer. 47, 629 (1963).Google Scholar
  60. 60.
    S. A. Hashim and T. B. Van Itallie, J. Am. Med. Assoc. 192, 289 (1965).CrossRefGoogle Scholar
  61. 61.
    J. B. Carey, Jr., and G. Williams, J. Am. Med. Assoc. 176, 432 (1961).CrossRefGoogle Scholar
  62. 62.
    L. J. Schoenfield and J. Sjövall, Am. J. Physiol. 211, 1069 (1966).PubMedGoogle Scholar
  63. 63.
    Anon., J. Am. Med. Assoc. 197, 261 (1966).Google Scholar
  64. 64.
    W. T. Beher, M. E. Beher, and B. Rao, Proc. Soc. Exptl. Biol. Med. 122, 881 (1966).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1971

Authors and Affiliations

  • A. Kuksis
    • 1
  1. 1.Banting and Best Department of Medical ResearchUniversity of TorontoTorontoCanada

Personalised recommendations