Bilirubin and Its Carbohydrate Conjugates

  • Norbert J. C. Blanckaert
Part of the Biological Methods book series (BM)


In mammals, the open tetrapyrrole bilirubin (structure 2, Fig. 1) is the principal degradation product of iron-protoporphyrin-IX (heme). The latter molecule is a tetrapyrrolic macrocycle and plays a critical role in aerobic metabolism by reversibly binding oxygen in hemoglobin and myoglobin, and by serving as the active site in oxidation reactions catalyzed by hemoprotein enzymes. Important cyclic tetrapyrroles in nature related to heme are chlorophylls, which contain magnesium and are derived from protoporphyrin-IX, and vitamin B12, a corrinoid derived from uroporphyrinogen-III.


Dimethyl Ester Hepatobiliary Disease Bile Pigment Unconjugated Bilirubin Tetrapyrrolic Macrocycle 
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.


  1. 1.
    Berk, P. D., and Javitt, N. B., Am. J. Med 64, 311 (1978).CrossRefGoogle Scholar
  2. 2.
    Billing, B. H., Gut 19, 481 (1978).CrossRefGoogle Scholar
  3. 3.
    Fevery, J. Blanckaert, N., Degroote, J., and Heirwegh, K. P. M., Bilirubin conjugates: formation and detection, in Progress in Liver Disease, Popper, H., and Schaffner, F., eds., vol. 5, Grune and Stratton, New York, 1976, pp. 183–214.Google Scholar
  4. 4.
    Schmid, R., Gastroenterology 74, 1307 (1978).Google Scholar
  5. 5.
    Schmid, R., and McDonagh, A. F., Hyperbilirubinemia, in The Metabolic Basis of Inherited Disease, Stanbury, J. B., Wyngaarden, J. B., and Frederickson, D. S., eds., McGraw-Hill, New York, 1978, pp. 1221–1257.Google Scholar
  6. 6.
    Bonnett, R., Nomenclature, in The Porphyrins, Dolphin, D., ed., vol. 1, Academic Press, New York, 1978, pp. 1–27.CrossRefGoogle Scholar
  7. 7.
    Heirwegh, K. P. M., Fevery, J., Meuwissen, J. A. T. P., Degroote, J., Compernolle, F., Desmet, V., and Van Roy, F. P., Methods Biochem. Anal 11, 205 (1974).CrossRefGoogle Scholar
  8. 8.
    Brodersen, R., and Theilgaard, J., Scand J. Clin. Lab. Med. 24, 395 (1969).CrossRefGoogle Scholar
  9. 9.
    Fog, J., and Jellum, E., Nature 198, 88 (1963).CrossRefGoogle Scholar
  10. 10.
    Bonnett, R., Davies, J. E., Hursthouse, M. B., and Sheldrick, G. M., Proc. Roy. Soc. Lond B. 202, 249 (1978).CrossRefGoogle Scholar
  11. 11.
    Mugnoli, A., Manitto, P., and Monti, D., Nature 273, 568 (1978).CrossRefGoogle Scholar
  12. 12.
    Lester, R., and Klein, P., J. Clin. Invest. 45, 1839 (1966).CrossRefGoogle Scholar
  13. 13.
    Blanckaert, N., Heirwegh, K. P. M., and Zaman, Z., Biochem. J. 164, 229 (1977).Google Scholar
  14. 14.
    Jones, E. A., Shrager, R., Bloomer, J. R., Berk, P. D., Howe, R. B., and Berlin, N. I., J. Clin. Invest. 51, 2450 (1972).CrossRefGoogle Scholar
  15. 15.
    Heirweigh, K. P. M., Formation, metabolism and significance of bilirubin-IX glycosides, in Conjugation Reactions in Drug Biotransformation, Aitio, A., ed., Elsevier/North, Holland Biomedical Press, Amsterdam, 1978, pp. 67–76.Google Scholar
  16. 16.
    Blanckaert, N., Compernolle, F., Leroy, P., Van Houtte, R., Fevery, J., and Heirwegh, K. P. M., Biochem. J., 171, 203 (1978).Google Scholar
  17. 17.
    Compernolle, F., Van Hees, G. P., Blanckaert, N., and Heirwegh, K. P. M., Biochem. J. 171, 185 (1978).Google Scholar
  18. 18.
    Kuenzle, C. C, Bilirubin conjugates in human bile, in Metabolic Conjugation and Metabolic Hydrolysis, Fishman, W. H., ed., vol. 3, Academic Press, New York, 1973, pp. 351–386.Google Scholar
  19. 19.
    Compernolle, F., Biochem. J. 175, 1095 (1978).Google Scholar
  20. 20.
    Isselbacher, K. J., and McCarthy, E. A., J. Clin. Invest. 38, 645 (1959).CrossRefGoogle Scholar
  21. 21.
    Noir, B., and Nanet, H., Biochim. Biophys. Acta. 372, 230 (1974).CrossRefGoogle Scholar
  22. 22.
    Kondo, T., Kawai, T., Yamamoto, T., and Izawa, T., Gastroenterol. Jap. 6, 217 (1971).Google Scholar
  23. 23.
    Ettner-Kjelsaas, H., and Kuenzle, C. C., Biochim. Biophys. Acta. 400, 83 (1975).CrossRefGoogle Scholar
  24. 24.
    Weber, A. P., and Schalm, L., Acta. Med. Scand 177, 519 (1965).Google Scholar
  25. 25.
    Jansen, P. L. M., Chowdhury, J. R., Fischberg, E. B., and Arias, I. M., J. Biol. Chem. 252, 2710 (1977).Google Scholar
  26. 26.
    Blanckaert, N., Gollan, J., and Schmid, R., Proc. Natl. Acad. Sci., USA 76, 2037 (1979).CrossRefGoogle Scholar
  27. 27.
    Gordon, E. R., and Goresky, C. A., Gastroenterol. 75, 966 (1978).Google Scholar
  28. 28.
    Blanckaert, N., Gollan, J., and Schmid, R., J. Clin. Invest. 65, 1332 (1980).CrossRefGoogle Scholar
  29. 29.
    Watson, C. J., Ann. Intern. Med. 70, 839 (1969).CrossRefGoogle Scholar
  30. 30.
    Bloomer, J. R., Berk, P. D., Howe, W. B., Waggoner, J. G., and Berlin, N. I., Clin. Chim. Acta. 29, 463 (1970).CrossRefGoogle Scholar
  31. 31.
    Billing, B. H., Cole, P. G., and Lathe, G. H., Biochem. J. 65, 774 (1957).Google Scholar
  32. 32.
    Schmid, R., J. Biol. Chem. 11, 881 (1957).Google Scholar
  33. 33.
    Talafant, E., Nature (London) 178, 312 (1956).CrossRefGoogle Scholar
  34. 34.
    Blanckaert, N., Kabra, P. M., Farina, F. A., Stafford, B. E., Marton, L. J., and Schmid, R., J. Lab. Clin. Med. 96, 198 (1980).Google Scholar
  35. 35.
    Ehrlich, P., Centr. klin. Med. 4, 721 (1883).Google Scholar
  36. 36.
    Van den Bergh, A. A. H., and Muller, P., Biochem. Z., 77, 90 (1916).Google Scholar
  37. 37.
    Billing, B. H., Haslam, R., and Wald, N., Ann. Clin. Biochem., 8, 21 (1971).Google Scholar
  38. 38.
    Van Roy, F. P., and Heirwegh, K. P. M., Biochem. J. 107, 507 (1968).Google Scholar
  39. 39.
    Hertz, H., Dybkaer, R., and Lauritzen, M., Scand. J. Clin. Lab. Invest. 34, 265 (1974).CrossRefGoogle Scholar
  40. 40.
    Jackson, S. H., and Hernandez, A. H., Clin. Chem. 16, 462 (1970).Google Scholar
  41. 41.
    Liley, A., Amer. J. Obstet. Gynecol. 82, 1359 (1961).Google Scholar
  42. 42.
    Ostrow, J. D., and Murphy, N. H., Biochem. J. 120, 311 (1970).Google Scholar
  43. 43.
    Brodersen, R., and Jacobsen, J., Separation and determination of bile pigments, in Methods of Biochemical Analysis, Glick, D., ed., Vol. 17, Wiley-Interscience, New York, 1969, pp. 3–54.Google Scholar
  44. 44.
    Weber, A. P., and Schalm, L., Clin. Chim. Acta. 7, 805 (1962).CrossRefGoogle Scholar
  45. 45.
    Eberlein, W. R., Pediatrics 25, 878 (1960).Google Scholar
  46. 46.
    Ostrow, J. D., and Boonyapisit, S. T., Biochem. J. 173, 263 (1978).Google Scholar
  47. 47.
    Bratlid, D., and Winsnes, A., Scand. J. Clin. Lab. Invest. 28, 41 (1971).CrossRefGoogle Scholar
  48. 48.
    Schoenfield, L. J., Foulk, W. T., and Bollman, J. L., Gastroenterology 47, 35 (1964).Google Scholar
  49. 49.
    Cole, P. G., Lathe, G. H., and Billing, B. H., Biochem. 57, 514 (1954).Google Scholar
  50. 50.
    Kuenzle, C. C., Maier, C., and Ruttner, J. R., J. Lab. Clin. Med. 67, 294 (1966).Google Scholar
  51. 51.
    Wolkoff, A. W., Scharschmidt, B. F., Plotz, P. H., and Berk, P. D., Proc. Soc. Exptl. Biol. Med 152, 20 (1976).CrossRefGoogle Scholar
  52. 52.
    Billing, B. H., J. Clin. Path. 8, 130 (1955).CrossRefGoogle Scholar
  53. 53.
    Gordon, E. R., Chan, T. H., Samodai, K., and Goresky, C. A., Biochem. J. 167, 1 (1977).Google Scholar
  54. 54.
    Thompson, R. P. H., and Hofmann, A. F. Clin. Chim. Acta. 35, 517 (1971).CrossRefGoogle Scholar
  55. 55.
    Salmon, M., Fenselau, C, Life Sci. 15, 2069 (1974).CrossRefGoogle Scholar
  56. 56.
    Heirwegh, K. P. M., Fevery, J., Michiels, R., Van Hees, G. P., and Compernolle, F., Biochem. J. 145, 185 (1975).Google Scholar
  57. 57.
    Noir, B. A., Biochem. J. 155, 365 (1976).Google Scholar
  58. 58.
    Blumenthal, S. G., Taggart, D. B., Ikeda, R. M., Ruebner, B. H., and Bergstrom, D. E., Biochem. J. 167, 535 (1977).Google Scholar
  59. 59.
    Jansen, F. H., and Billing, B. H., Biochem. J. 125, 917 (1971).Google Scholar
  60. 60.
    Lim, C. K., J. Liq. Chromatog. 2, 37 (1979).CrossRefGoogle Scholar
  61. 61.
    Onishi, S., Itoh, S., Kawade, N., Isobe, K., and Sugiyama, S., Biochem. J. 185, 281 (1980).Google Scholar
  62. 62.
    Yamaguchi, T., Yamaguchi, N., Nakajima, H., Komoda, Y., and Ishikawa, M., Proc. Japan Acad. 55, Ser. B., 89 (1979).CrossRefGoogle Scholar
  63. 63.
    Blanckaert, N., Biochem. J. 185, 115 (1980).Google Scholar
  64. 64.
    Scharschmidt, B. F., Blanckaert, N., Farina, F., Kabra, P., Weisiger, R., Marton, L., and Schmid, R., Gastroenterology 77, A–39 (1979).Google Scholar
  65. 65.
    Rosenthal, P., Blanckaert, N., Kabra, P. M., and Thaler, M. M., Gastroenterology 77, A–35 (1979).Google Scholar
  66. 66.
    Bratlid, D., and Winsnes, A., Scand. J. Clin. Lab. Invest. 31, 231 (1973).CrossRefGoogle Scholar
  67. 67.
    Blanckaert, N., Fevery, J., Heirwegh, K. P. M., and Compernolle, F., Biochem. J. 164, 237 (1977).Google Scholar
  68. 68.
    Blumenthal, S. G., Stucker, T., Rasmusssen, R. D., Ikeda, R. M., Ruebner, B. H., Bergstrom, D. E., and Hanson, F. W., Biochem. J. 186, 693 (1980).Google Scholar
  69. 69.
    Blanckaert, N., Heirwegh, K. P. M., and Compernolle, Biochem. J. 155, 405 (1976).Google Scholar
  70. 70.
    Yamaguchi, T., Yamaguchi, N., Nakajima, H., Komoda, Y., and Ishikawa, M., Proc. Japan Acad. 55, Ser. B., 84 (1979).CrossRefGoogle Scholar
  71. 71.
    McDonagh, A. F., and Assisi, F.: FEBS Lett. 18, 315 (1971).CrossRefGoogle Scholar
  72. 72.
    Wooldridge, T. A., and Lightner, D. A., J. Liq. Chromatog. 1, 653 (1978).CrossRefGoogle Scholar
  73. 73.
    Lightner, D. A., Wooldridge, T. A., and McDonagh, A. F., Proc. Natl. Acad. Sci. USA 76, 29 (1979).CrossRefGoogle Scholar
  74. 74.
    Onishi, S., Itoh, S., Kawade, N., Isobe, K., and Sugiyama, S., Biochem. Biophys. Res. Comm. 90, 890 (1979).CrossRefGoogle Scholar
  75. 75.
    Brodersen, R., Detection of free bilirubin: a criterion for exchange transfusion, in Liver Diseases in Infancy and Childhood, Berenberg, S. R., ed., Martinus Nijhoff, The Hague, 1976, pp. 18–24.CrossRefGoogle Scholar
  76. 76.
    Lu, K. C., Gooding, K. M., and Regnier, F. E., Clin. Chem. 25, 1608 (1979).Google Scholar
  77. 77.
    Schoch, S., Lempert, U., Wieschoff, H., and Scheer, H., J. Chromatog. 157, 357 (1978).CrossRefGoogle Scholar
  78. 78.
    Fu, E., Friedman, L., and Siegelman, H. W., Biochem. J. 179, 1 (1979).Google Scholar
  79. 79.
    Rasmussen, R. D., Yokoyama, W. H., Blumenthal, S. G., Bergstrom, D. E., and Reubner, B. H., Anal. Biochem. 101, 66 (1980).CrossRefGoogle Scholar

Copyright information

© The Humana Press, Inc. 1981

Authors and Affiliations

  • Norbert J. C. Blanckaert
    • 1
    • 2
  1. 1.Department of Laboratory Medicine and Liver CenterUniversity of California Medical CenterSan Francisco
  2. 2.Department of Medical Research, Campus GasthuisbergUniversity of LeuvenLeuvenBelgium

Personalised recommendations