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. 1971 Dec;125(4):929–934. doi: 10.1042/bj1250929a

Formation of bilirubin glucoside

Kim Ping Wong 1
PMCID: PMC1178253  PMID: 5144254

Abstract

1. Rat liver microsomal preparation can effect the transglucosylation from UDP-glucose to bilirubin in the presence of Mg2+. 2. Other nucleotides, namely CDP-glucose, ADP-glucose and GDP-glucose, were not active as glucosyl donors. 3. Only trace amounts of galactose, galacturonic acid and N-acetylglucosamine were conjugated to bilirubin when their respective UDP derivatives were used in the reaction mixture. 4. The azobilirubin glucosides produced by coupling with p-diazobenzenesulphonic acid and diazotized ethyl anthranilic acid were separable from the corresponding azobilirubin glucuronides by t.l.c. 5. The glucoside was, however, hydrolysed by both β-glucosidase and various preparations of β-glucuronidase; azobilirubin and glucose were liberated in the process. 6. Kinetic studies showed that the effects of pH and Mg2+ on the two conjugating systems were similar. 7. The specific activities of hepatic bilirubin UDP-glucosyltransferase, expressed as μg of bilirubin `equivalents' conjugated/h per mg of protein, are respectively 1.7 and 2.4 for male and female rats. 8. The Km values for bilirubin and UDP-glucose are 5.7×10−5m and 1.6×10−3m respectively. 9. The glucoside and glucuronide conjugations of bilirubin are discussed in relation to the availability of the conjugating agents and aglycone in the liver.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Adlard B. P., Lathe G. H. The effect of steroids and nucleotidesoon solubilized bilirubin uridine diphosphate-glucuronyltransferase. Biochem J. 1970 Sep;119(3):437–445. doi: 10.1042/bj1190437. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. BRODERSEN R., HERMANN L. S., VIND I. NORMAL BILIRUBIN CONCENTRATION AND THE OCCURRENCE OF OTHER BILE PIGMENTS IN HUMAN BLOOD SERA. Scand J Clin Lab Invest. 1963;15:523–528. [PubMed] [Google Scholar]
  3. Collins D. C., Williamson D. G., Layne D. S. Steroid glucosides. Enzymatic synthesis by a partially purified transferase from rabbit liver microsomes. J Biol Chem. 1970 Feb 25;245(4):873–876. [PubMed] [Google Scholar]
  4. GOLDBERG N. D., DAHL J. L., PARKS R. E., Jr URIDINE DIPHOSPHATE GLUCOSE DEHYDROGENASE. PH DEPENDENCE OF THE REACTIONS WITH THE 5-FLUOROURACIL AND 6-AZAURACIL ANALOGUES OF URIDINE DIPHOSPHATE GLUCOSE. J Biol Chem. 1963 Sep;238:3109–3114. [PubMed] [Google Scholar]
  5. HSIA D. Y., RIABOV S., DOWBEN R. M. INHIBITION OF GLUCURONOSYL TRANSFERASE BY STEROID HORMONES. Arch Biochem Biophys. 1963 Nov;103:181–185. doi: 10.1016/0003-9861(63)90392-8. [DOI] [PubMed] [Google Scholar]
  6. Heirwegh K. P., Van Hees G. P., Compernolle F., Fevery J. Excretion of bilirubin conjugated with glucose in dog bile. Biochem J. 1970 Dec;120(4):17P–17P. doi: 10.1042/bj1200017pa. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. ISSELBACHER K. J., McCARTHY E. A. Studies on bilirubin sulfate and other nonglucuronide conjugates of bilirubin. J Clin Invest. 1959 Apr;38(4):645–651. doi: 10.1172/JCI103842. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Illing H. P., Dutton G. J. Observations on the biosynthesis of thioglucuronides and thioglucosides in vertebrates and molluscs. Biochem J. 1970 Dec;120(4):16P–17P. doi: 10.1042/bj1200016p. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. KALCKAR H. M., MAXWELL E. S., STROMINGER J. L. Some properties of uridine diphosphoglucose dehydrogenase. Arch Biochem Biophys. 1956 Nov;65(1):2–10. doi: 10.1016/0003-9861(56)90171-0. [DOI] [PubMed] [Google Scholar]
  10. Kuenzle C. C. Bilirubin conjugates of human bile. The excretion of bilirubin as the acyl glycosides of aldobiouronic acid, pseudoaldobiouronic acid and hexuronosylhexuronic acid, with a branched-chain hexuronic acid as one of the components of the hexuronosylhexuronide. Biochem J. 1970 Sep;119(3):411–435. doi: 10.1042/bj1190411. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  12. MAXWELL E. S. The enzymic interconversion of uridine diphosphogalactose and uridine diphosphoglucose. J Biol Chem. 1957 Nov;229(1):139–151. [PubMed] [Google Scholar]
  13. Müller-Oerlinghausen B., Künzel B. Sex differences in the activity of rat liver UDPG-dehydrogenase. Life Sci. 1968 Nov 15;7(22):1129–1133. doi: 10.1016/0024-3205(68)90219-1. [DOI] [PubMed] [Google Scholar]
  14. NEUFELD E. F., HALL C. W. INHIBITION OF UDP-D-GLUCOSE DEHYDROGENASE BY UDP-D-XYLOSE: A POSSIBLE REGULATORY MECHANISM. Biochem Biophys Res Commun. 1965 May 3;19:456–461. doi: 10.1016/0006-291x(65)90146-4. [DOI] [PubMed] [Google Scholar]
  15. Noir B. A., De Walz A. T., Rodriguez Garay E. A. Studies on the bilirubin sulphate conjugate excreted in human bile. Biochim Biophys Acta. 1970 Oct 27;222(1):15–27. doi: 10.1016/0304-4165(70)90347-8. [DOI] [PubMed] [Google Scholar]
  16. SAAYMAN H. M., ROUX D. G. CONFIGURATION OF GUIBOURTACACIDIN, AND SYNTHESIS OF ISOMERIC RACEMATES. Biochem J. 1965 Jul;96:36–42. doi: 10.1042/bj0960036. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. STEINER D. F., YOUNGER L., KING J. PURIFICATION AND PROPERTIES OF URIDINE DIPHOSPHATE GLUCOSE-GLYCOGEN GLUCOSYLTRANSFERASE FROM RAT LIVER. Biochemistry. 1965 Apr;4:740–751. doi: 10.1021/bi00880a020. [DOI] [PubMed] [Google Scholar]
  18. Smith J. N., Turbert H. B. Comparative detoxication. 11. Conjugations of 1-naphthol and some other phenols in houseflies and locusts. Biochem J. 1964 Jul;92(1):127–131. doi: 10.1042/bj0920127. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Van Heyningen R. Fluorescent glucoside in the human lens. Nature. 1971 Apr 9;230(5293):393–394. doi: 10.1038/230393a0. [DOI] [PubMed] [Google Scholar]
  20. Van Roy F. P., Heirwegh K. P. Determination of bilirubin glucuronide and assay of glucuronyltransferase with bilirubin as acceptor. Biochem J. 1968 Apr;107(4):507–518. doi: 10.1042/bj1070507. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Williamson D. G., Collins D. C., Layne D. S., Conrow R. B., Bernstein S. Isolation of 17-alpha-estradiol 17-beta-D-glucopyranoside from rabbit urine, and its synthesis and characterization. Biochemistry. 1969 Nov;8(11):4299–4304. doi: 10.1021/bi00839a012. [DOI] [PubMed] [Google Scholar]
  22. Williamson D. G., Polakova A., Layne D. S. Estrogen glucosides and galactosides: formation by rabbit liver microsomes in vitro. Biochem Biophys Res Commun. 1971 Mar 19;42(6):1057–1062. doi: 10.1016/0006-291x(71)90011-8. [DOI] [PubMed] [Google Scholar]
  23. Wong K. P. Bilirubin glucuronyltransferase. Specific assay and kinetic studies. Biochem J. 1971 Nov;125(1):27–35. doi: 10.1042/bj1250027. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. Wong K. P., Sourkes T. L. Determination of UDPG and UDPGA in tissues. Anal Biochem. 1967 Dec;21(3):444–453. doi: 10.1016/0003-2697(67)90319-3. [DOI] [PubMed] [Google Scholar]

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