Skip to main content
SpringerLink
Log in

Bilirubin and Its Carbohydrate Conjugates

  • Protocol
Liquid Chromatography In Clinical Analysis

Part of the book series: Biological Methods ((BM))

  • 543 Accesses

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Notes

  1. 1.

    *

    Dipyrrole exchange is used to denote disproportionation of bilirubins. This reaction involves cleavage of each molecule at either side of the central C-10 bridge into two dipyrrolic fragments, followed by random recombination of dipyrrole moieties from different molecules (71).

References

  1. Berk, P. D., and Javitt, N. B., Am. J. Med 64, 311 (1978).

    Article  CAS  Google Scholar 

  2. Billing, B. H., Gut 19, 481 (1978).

    Article  CAS  Google Scholar 

  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. Schmid, R., Gastroenterology 74, 1307 (1978).

    CAS  Google Scholar 

  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. Bonnett, R., Nomenclature, in The Porphyrins, Dolphin, D., ed., vol. 1, Academic Press, New York, 1978, pp. 1–27.

    Chapter  Google Scholar 

  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).

    Article  Google Scholar 

  8. Brodersen, R., and Theilgaard, J., Scand J. Clin. Lab. Med. 24, 395 (1969).

    Article  CAS  Google Scholar 

  9. Fog, J., and Jellum, E., Nature 198, 88 (1963).

    Article  CAS  Google Scholar 

  10. Bonnett, R., Davies, J. E., Hursthouse, M. B., and Sheldrick, G. M., Proc. Roy. Soc. Lond B. 202, 249 (1978).

    Article  CAS  Google Scholar 

  11. Mugnoli, A., Manitto, P., and Monti, D., Nature 273, 568 (1978).

    Article  CAS  Google Scholar 

  12. Lester, R., and Klein, P., J. Clin. Invest. 45, 1839 (1966).

    Article  CAS  Google Scholar 

  13. Blanckaert, N., Heirwegh, K. P. M., and Zaman, Z., Biochem. J. 164, 229 (1977).

    CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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. Blanckaert, N., Compernolle, F., Leroy, P., Van Houtte, R., Fevery, J., and Heirwegh, K. P. M., Biochem. J., 171, 203 (1978).

    CAS  Google Scholar 

  17. Compernolle, F., Van Hees, G. P., Blanckaert, N., and Heirwegh, K. P. M., Biochem. J. 171, 185 (1978).

    CAS  Google Scholar 

  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. Compernolle, F., Biochem. J. 175, 1095 (1978).

    CAS  Google Scholar 

  20. Isselbacher, K. J., and McCarthy, E. A., J. Clin. Invest. 38, 645 (1959).

    Article  CAS  Google Scholar 

  21. Noir, B., and Nanet, H., Biochim. Biophys. Acta. 372, 230 (1974).

    Article  CAS  Google Scholar 

  22. Kondo, T., Kawai, T., Yamamoto, T., and Izawa, T., Gastroenterol. Jap. 6, 217 (1971).

    CAS  Google Scholar 

  23. Ettner-Kjelsaas, H., and Kuenzle, C. C., Biochim. Biophys. Acta. 400, 83 (1975).

    Article  Google Scholar 

  24. Weber, A. P., and Schalm, L., Acta. Med. Scand 177, 519 (1965).

    CAS  Google Scholar 

  25. Jansen, P. L. M., Chowdhury, J. R., Fischberg, E. B., and Arias, I. M., J. Biol. Chem. 252, 2710 (1977).

    CAS  Google Scholar 

  26. Blanckaert, N., Gollan, J., and Schmid, R., Proc. Natl. Acad. Sci., USA 76, 2037 (1979).

    Article  CAS  Google Scholar 

  27. Gordon, E. R., and Goresky, C. A., Gastroenterol. 75, 966 (1978).

    Google Scholar 

  28. Blanckaert, N., Gollan, J., and Schmid, R., J. Clin. Invest. 65, 1332 (1980).

    Article  CAS  Google Scholar 

  29. Watson, C. J., Ann. Intern. Med. 70, 839 (1969).

    Article  CAS  Google Scholar 

  30. Bloomer, J. R., Berk, P. D., Howe, W. B., Waggoner, J. G., and Berlin, N. I., Clin. Chim. Acta. 29, 463 (1970).

    Article  CAS  Google Scholar 

  31. Billing, B. H., Cole, P. G., and Lathe, G. H., Biochem. J. 65, 774 (1957).

    CAS  Google Scholar 

  32. Schmid, R., J. Biol. Chem. 11, 881 (1957).

    Google Scholar 

  33. Talafant, E., Nature (London) 178, 312 (1956).

    Article  CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  35. Ehrlich, P., Centr. klin. Med. 4, 721 (1883).

    Google Scholar 

  36. Van den Bergh, A. A. H., and Muller, P., Biochem. Z., 77, 90 (1916).

    Google Scholar 

  37. Billing, B. H., Haslam, R., and Wald, N., Ann. Clin. Biochem., 8, 21 (1971).

    CAS  Google Scholar 

  38. Van Roy, F. P., and Heirwegh, K. P. M., Biochem. J. 107, 507 (1968).

    Google Scholar 

  39. Hertz, H., Dybkaer, R., and Lauritzen, M., Scand. J. Clin. Lab. Invest. 34, 265 (1974).

    Article  CAS  Google Scholar 

  40. Jackson, S. H., and Hernandez, A. H., Clin. Chem. 16, 462 (1970).

    CAS  Google Scholar 

  41. Liley, A., Amer. J. Obstet. Gynecol. 82, 1359 (1961).

    CAS  Google Scholar 

  42. Ostrow, J. D., and Murphy, N. H., Biochem. J. 120, 311 (1970).

    CAS  Google Scholar 

  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. Weber, A. P., and Schalm, L., Clin. Chim. Acta. 7, 805 (1962).

    Article  CAS  Google Scholar 

  45. Eberlein, W. R., Pediatrics 25, 878 (1960).

    Google Scholar 

  46. Ostrow, J. D., and Boonyapisit, S. T., Biochem. J. 173, 263 (1978).

    CAS  Google Scholar 

  47. Bratlid, D., and Winsnes, A., Scand. J. Clin. Lab. Invest. 28, 41 (1971).

    Article  CAS  Google Scholar 

  48. Schoenfield, L. J., Foulk, W. T., and Bollman, J. L., Gastroenterology 47, 35 (1964).

    CAS  Google Scholar 

  49. Cole, P. G., Lathe, G. H., and Billing, B. H., Biochem. 57, 514 (1954).

    CAS  Google Scholar 

  50. Kuenzle, C. C., Maier, C., and Ruttner, J. R., J. Lab. Clin. Med. 67, 294 (1966).

    CAS  Google Scholar 

  51. Wolkoff, A. W., Scharschmidt, B. F., Plotz, P. H., and Berk, P. D., Proc. Soc. Exptl. Biol. Med 152, 20 (1976).

    Article  CAS  Google Scholar 

  52. Billing, B. H., J. Clin. Path. 8, 130 (1955).

    Article  CAS  Google Scholar 

  53. Gordon, E. R., Chan, T. H., Samodai, K., and Goresky, C. A., Biochem. J. 167, 1 (1977).

    CAS  Google Scholar 

  54. Thompson, R. P. H., and Hofmann, A. F. Clin. Chim. Acta. 35, 517 (1971).

    Article  CAS  Google Scholar 

  55. Salmon, M., Fenselau, C, Life Sci. 15, 2069 (1974).

    Article  CAS  Google Scholar 

  56. Heirwegh, K. P. M., Fevery, J., Michiels, R., Van Hees, G. P., and Compernolle, F., Biochem. J. 145, 185 (1975).

    CAS  Google Scholar 

  57. Noir, B. A., Biochem. J. 155, 365 (1976).

    CAS  Google Scholar 

  58. Blumenthal, S. G., Taggart, D. B., Ikeda, R. M., Ruebner, B. H., and Bergstrom, D. E., Biochem. J. 167, 535 (1977).

    CAS  Google Scholar 

  59. Jansen, F. H., and Billing, B. H., Biochem. J. 125, 917 (1971).

    CAS  Google Scholar 

  60. Lim, C. K., J. Liq. Chromatog. 2, 37 (1979).

    Article  CAS  Google Scholar 

  61. Onishi, S., Itoh, S., Kawade, N., Isobe, K., and Sugiyama, S., Biochem. J. 185, 281 (1980).

    CAS  Google Scholar 

  62. Yamaguchi, T., Yamaguchi, N., Nakajima, H., Komoda, Y., and Ishikawa, M., Proc. Japan Acad. 55, Ser. B., 89 (1979).

    Article  CAS  Google Scholar 

  63. Blanckaert, N., Biochem. J. 185, 115 (1980).

    CAS  Google Scholar 

  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. Rosenthal, P., Blanckaert, N., Kabra, P. M., and Thaler, M. M., Gastroenterology 77, A–35 (1979).

    Google Scholar 

  66. Bratlid, D., and Winsnes, A., Scand. J. Clin. Lab. Invest. 31, 231 (1973).

    Article  CAS  Google Scholar 

  67. Blanckaert, N., Fevery, J., Heirwegh, K. P. M., and Compernolle, F., Biochem. J. 164, 237 (1977).

    CAS  Google Scholar 

  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).

    CAS  Google Scholar 

  69. Blanckaert, N., Heirwegh, K. P. M., and Compernolle, Biochem. J. 155, 405 (1976).

    CAS  Google Scholar 

  70. Yamaguchi, T., Yamaguchi, N., Nakajima, H., Komoda, Y., and Ishikawa, M., Proc. Japan Acad. 55, Ser. B., 84 (1979).

    Article  CAS  Google Scholar 

  71. McDonagh, A. F., and Assisi, F.: FEBS Lett. 18, 315 (1971).

    Article  CAS  Google Scholar 

  72. Wooldridge, T. A., and Lightner, D. A., J. Liq. Chromatog. 1, 653 (1978).

    Article  CAS  Google Scholar 

  73. Lightner, D. A., Wooldridge, T. A., and McDonagh, A. F., Proc. Natl. Acad. Sci. USA 76, 29 (1979).

    Article  CAS  Google Scholar 

  74. Onishi, S., Itoh, S., Kawade, N., Isobe, K., and Sugiyama, S., Biochem. Biophys. Res. Comm. 90, 890 (1979).

    Article  CAS  Google Scholar 

  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.

    Chapter  Google Scholar 

  76. Lu, K. C., Gooding, K. M., and Regnier, F. E., Clin. Chem. 25, 1608 (1979).

    CAS  Google Scholar 

  77. Schoch, S., Lempert, U., Wieschoff, H., and Scheer, H., J. Chromatog. 157, 357 (1978).

    Article  CAS  Google Scholar 

  78. Fu, E., Friedman, L., and Siegelman, H. W., Biochem. J. 179, 1 (1979).

    CAS  Google Scholar 

  79. Rasmussen, R. D., Yokoyama, W. H., Blumenthal, S. G., Bergstrom, D. E., and Reubner, B. H., Anal. Biochem. 101, 66 (1980).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Laboratory Medicine and Liver Center, University of California Medical Center, San Francisco, California

    Norbert J. C. Blanckaert

  2. Department of Medical Research, Campus Gasthuisberg, University of Leuven, Leuven, Belgium

    Norbert J. C. Blanckaert

Authors
  1. Norbert J. C. Blanckaert
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. University of California School of Medicine, San Francisco, California

    Pokar M. Kabra  & Laurence J. Marton  & 

Rights and permissions

Reprints and permissions

Copyright information

© 1981 The Humana Press, Inc.

About this protocol

Cite this protocol

Blanckaert, N.J.C. (1981). Bilirubin and Its Carbohydrate Conjugates. In: Kabra, P.M., Marton, L.J. (eds) Liquid Chromatography In Clinical Analysis. Biological Methods. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-60327-404-3_15

Download citation

  • DOI: https://doi.org/10.1007/978-1-60327-404-3_15

  • Publisher Name: Humana Press, Totowa, NJ

  • Print ISBN: 978-0-89603-026-8

  • Online ISBN: 978-1-60327-404-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation