Abstract
1. Bilirubin-IXalpha, -IXalpha diglucuronide, -IXalpha monoglucuronide, -IXalpha monoglucoside -IXalpha monoxyloside, a bilirubin-IXalpha diconjugate containing glucose and another unknown compound, and bilirubin-IXbeta are present in gall-bladder bile of adult human, rhesus monkey and dog. Dog bile normally also contains other bilirubin-IXalpha diconjugates, i.e. compounds containing two conjugating sugars such as glucuronic acid and glucose, glucuronic acid and xylose and glucose xylose. 2. Azopigments alphaF, alphaO, alpha2, alpha3, betax and delta derived from human and rhesus-monkey bilirubins are identical in their chemical composition with those obtained from the dog. 3. Azopigments alphaF and betax found in diazotized biles of adult humans, rhesus monkeys and dogs are products of unconjugated bilirubin-IXbeta. 4. Technical modifications of previously published procedures [Heirwegh, Fevery, Michiels, Van Hees & Compernolle, (1975) Biochem. J. 145, 185-199] were introduced which make it possible to separate the bilirubins, diazotize the separated bilirubins, extract the azopigments and chromatograph them in one working day (6-8h).
Full text
PDF













Images in this article
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Blanckaert N., Heirwegh K. P., Compernolle F. Synthesis and separation by thin-layer chromatography of bilirubin-IX isomers. Their identification as tetrapyrroles and dipyrrolic ethyl anthranilate azo derivatives. Biochem J. 1976 May 1;155(2):405–417. doi: 10.1042/bj1550405. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Blumenthal S. G., Ikeda R. M., Ruebner B. H. Bile pigments in humans and in nonhuman primates during the perinatal period: composition of meconium and gallbladder bile of newborns and adults. Pediatr Res. 1976 Jul;10(7):664–668. doi: 10.1203/00006450-197607000-00007. [DOI] [PubMed] [Google Scholar]
- Bonnett R., McDonagh A. F. The meso-reactivity of porphyrins and related compounds. VI. Oxidative cleavage of the haem system. The four isomeric biliverdins of the IX series. J Chem Soc Perkin 1. 1973;9:881–888. doi: 10.1039/p19730000881. [DOI] [PubMed] [Google Scholar]
- Combe M. G., Henbest H. B., Jackson W. R. Aspects of stereochemistry. XXI. Hydrogenation of 3-oxo-delta-4-steroids over a palladium-calcium carbonate catalyst. J Chem Soc Perkin 1. 1967;22:2467–2469. [PubMed] [Google Scholar]
- Compernolle F., Blanckaert N., Heirwegh K. P. Mass spectral study of derivatives of the four bilirubin-IX isomers. Biomed Mass Spectrom. 1976 Aug;3(4):155–160. doi: 10.1002/bms.1200030403. [DOI] [PubMed] [Google Scholar]
- Compernolle F., Jansen F. H., Heirwegh K. P. Mass-spectrometric study of the azopigments obtained from bile pigments with diazotized ethyl anthranilate. Biochem J. 1970 Dec;120(4):891–894. doi: 10.1042/bj1200891. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Compernolle F., Van Hees G. P., Fevery J., Heirwegh K. P. Mass-spectrometric structure elucidation of dog bile azopigments as the acyl glycosides of glucopyranose and xylopyranose. Biochem J. 1971 Dec;125(3):811–819. doi: 10.1042/bj1250811. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Fevery J., Van Damme B., Michiels R., De Groote J., Heirwegh K. P. Bilirubin conjugates in bile of man and rat in the normal state and in liver disease. J Clin Invest. 1972 Sep;51(9):2482–2492. doi: 10.1172/JCI107062. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Fevery J., Van Hees G. P., Leroy P., Compernolle F., Heirwegh K. P. Excretion in dog bile of glucose and xylose conjugates of bilirubin. Biochem J. 1971 Dec;125(3):803–810. doi: 10.1042/bj1250803. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gordon E. R., Dadoun M., Goresky C. A., Chan T. H., Perlin A. S. The isolation of an azobilirubin beta-D-monoglucoside from dog gall-bladder bile. Biochem J. 1974 Oct;143(1):97–105. doi: 10.1042/bj1430097. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gordon E. R., Goresky C. A., Chang T. H., Perlin A. S. The isolation and characterization of bilirubin diglucuronide, the major bilirubin conjugate in dog and human bile. Biochem J. 1976 Jun 1;155(3):477–486. doi: 10.1042/bj1550477. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Heirwegh K. P., Fevery J., Meuwissen J. A., De Groote J., Compernolle F., Desmet V., Van Roy F. P. Recent advances in the separation and analysis of diazo-positive bile pigments. Methods Biochem Anal. 1974;22:205–250. doi: 10.1002/9780470110423.ch5. [DOI] [PubMed] [Google Scholar]
- Heirwegh K. P., Fevery J., Michiels R., van Hees G. P., Compernolle F. Separation by thin-layer chromatography and structure elucidation of bilirubin conjugates isolated from dog bile. Biochem J. 1975 Feb;145(2):185–199. doi: 10.1042/bj1450185. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Heirwegh K. P., Van Hees G. P., Leroy P., Van Roy F. P., Jansen F. H. Heterogeneity of bile pigment conjugates as revealed by chromatography of their ethyl anthranilate azopigments. Biochem J. 1970 Dec;120(4):877–890. doi: 10.1042/bj1200877. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Jansen F. H., Stoll M. S. Separation and structural analysis of vinyl- and isovinyl-azobilirubin derivatives. Biochem J. 1971 Nov;125(2):585–597. doi: 10.1042/bj1250585. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Noir B. A. Bilirubin conjugates in bile of man, rat and dog. Semi-quantitative analysis of bile composition by thin-layer chromatography. Biochem J. 1976 May 1;155(2):365–373. doi: 10.1042/bj1550365. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Schmid R., McDonagh A. F. The enzymatic formation of bilirubin. Ann N Y Acad Sci. 1975 Apr 15;244:533–552. doi: 10.1111/j.1749-6632.1975.tb41553.x. [DOI] [PubMed] [Google Scholar]
- Vaisman S. L., Lee K. S., Gartner L. M. Various bilirubin conjugates in pregnant and nonpregnant rats with and without phenobarbital treatment. Pediatr Res. 1976 Feb;10(2):111–113. doi: 10.1203/00006450-197602000-00008. [DOI] [PubMed] [Google Scholar]