{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T02:46:23Z","timestamp":1788921983072,"version":"build-2803163510"},"reference-count":39,"publisher":"Ovid Technologies (Wolters Kluwer Health)","issue":"2","license":[{"start":{"date-parts":[[2015,9,1]],"date-time":"2015-09-01T00:00:00Z","timestamp":1441065600000},"content-version":"tdm","delay-in-days":11872,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["lww.com","ovid.com"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[1983,3]]},"abstract":"<jats:sec>\n            <jats:title\/>\n            <jats:p>A method was developed to extract quantitatively the bilirubins from bile, urine, serum, stool, and preparations from liver with a chloroform\u2013ethanol mixture at pH 1.8 in the presence of ascorbic acid and NaCl. Extracted pigment was submitted to thin\u2013layer chromatography, and the separated bilirubins were either immediately eluted and determined spectrophotometrically or individually converted to ethyl anthranilate azo derivatives for thin\u2013layer chromatographic analysis of each isolated pigment band. Bilirubins in duodenal bile of eight healthy adults comprised 1.5 \u00b1 1.3% unconjugated bilirubin\u2013IX\u03b1, 69 \u00b1 6% bilirubin diglucuronide, and 16 \u00b1 4% bilirubin monoglucuronides. Mixed diconjugates containing one glucuronosyl moiety and either one xylosyl or one glucosyl group amounted to 10 \u00b1 3%. Most samples (6 of 8) contained trace amounts (0.6 \u00b1 0.6%) of unconjugated bilirubin\u2013IX\u03b2, in agreement with nearly exclusive cleavage of heme at the \u03b1\u2013meso position. The composition of the bilirubins in bile was normal in 6 patients with cholesterol gallstones, 4 with chronic hepatitis, and 3 with hemolysis. In duodenal bile of individuals with Gilbert's syndrome (n = 10), the concentration of bttirubin conjugates was comparable to that in healthy adults, but the proportion of bilirubin diglucuronides (52 \u00b1 8%) was decreased. The concentration of unconjugated bilirubin\u2013IX\u03b1 showed a fair positive correlation with that of bilirubin monoglucuronide and was increased in half of the patients with Gilbert's syndrome.<\/jats:p>\n          <\/jats:sec>","DOI":"10.1002\/hep.1840030207","type":"journal-article","created":{"date-parts":[[2010,7,5]],"date-time":"2010-07-05T11:59:58Z","timestamp":1278331198000},"page":"177-183","update-policy":"https:\/\/doi.org\/10.1097\/lww.0000000000001000","source":"Crossref","is-referenced-by-count":60,"title":["Analysis of Bilirubins in Biological Fluids by Extraction and Thin\u2013Layer Chromatography of the Intact Tetrapyrroles: Application to Bile of Patients With Gilbert's Syndrome, Hemolysis, or Cholelithiasis"],"prefix":"10.1097","volume":"3","author":[{"given":"Johan","family":"Fevery","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Norbert","family":"Blanckaert","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pol","family":"Leroy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roger","family":"Michiels","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karel P.M.","family":"Heirwegh","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"276","reference":[{"key":"10.1002\/hep.1840030207-BIB1|cit1","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1042\/bj1640737","article-title":"Comparison in different species of bilirubin-IXa conjugates with the activities of hepatic and renal bilirubin-IX\u03b1-uridine diphosphate glycosyltrans-ferases","volume":"164","author":"Fevery","year":"1977","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB2|cit2","doi-asserted-by":"crossref","first-page":"2482","DOI":"10.1172\/JCI107062","article-title":"Bilirubin conjugates in bile of man and rat in the normal state and in liver disease","volume":"51","author":"Fevery","year":"1972","journal-title":"J Clin Invest"},{"key":"10.1002\/hep.1840030207-BIB3|cit3","doi-asserted-by":"crossref","first-page":"970","DOI":"10.1172\/JCI108877","article-title":"Unconjugated bilirubin and an increased proportion of bilirubin monoconjugates in the bile of patients with Gilberts syndrome and Crigler-Najjar disease","volume":"60","author":"Fevery","year":"1977","journal-title":"J Clin Invest"},{"key":"10.1002\/hep.1840030207-BIB4|cit4","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1111\/j.1365-2362.1980.tb00023.x","article-title":"Glucuronidation of bilirubin and the occurrence of pigment gallstones in patients with chronic haemolytic diseases","volume":"10","author":"Fevery","year":"1980","journal-title":"Eur J Clin Invest"},{"key":"10.1002\/hep.1840030207-BIB5|cit5","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1042\/cs0550063","article-title":"Definition of a conjugation dysfunction in Gilbert's syndrome: studies of the handling of bilirubin loads and of the pattern of bilirubin conjugates secreted in bile","volume":"55","author":"Goresky","year":"1978","journal-title":"Clin Sci Molec Dis"},{"key":"10.1002\/hep.1840030207-BIB6|cit6","doi-asserted-by":"crossref","first-page":"458","DOI":"10.1016\/S0021-9673(00)97973-1","article-title":"Separation and identification of biliverdin isomers and isomer analysis of phycobilins and bilirubin","volume":"50","author":"O'Carra","year":"1970","journal-title":"J Chromat"},{"key":"10.1002\/hep.1840030207-BIB7|cit7","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1042\/bj1640237","article-title":"Characterization of the major diazo-positive bile pigments in bile of homozygous Gunn rats","volume":"164","author":"Blanckaert","year":"1977","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB8|cit8","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1042\/bj1670535","article-title":"Conjugated and unconjugated bilirubins in bile of humans and rhesus monkeys. Structure of adult human and rhesus-monkey bilirubins compared with dog bilirubins","volume":"167","author":"Blumenthal","year":"1977","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB9|cit9","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1042\/bj1850115","article-title":"Analysis of bilirubin and bilirubin mono- and diconjugates. Determination of their relative amounts in biological fluids","volume":"185","author":"Blanckaert","year":"1980","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB10|cit10","first-page":"198","article-title":"Measurement of bilirubin and its monoconjugates and diconjugates in human serum by alkaline methanolysis and high-performance liquid chromatography","volume":"96","author":"Blanckaert","year":"1980","journal-title":"J Lab Clin Med"},{"key":"10.1002\/hep.1840030207-BIB11|cit11","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1016\/0009-8981(71)90234-8","article-title":"Separation of bilirubin and its conjugates by thin layer chromatography","volume":"35","author":"Thompson","year":"1971","journal-title":"Clin Chim Acta"},{"key":"10.1002\/hep.1840030207-BIB12|cit12","first-page":"857","article-title":"Measurement of conjugated and unconjugated bilirubin in bile. II. A new thin-layer chromatographic method","volume":"88","author":"Boonyapisit","year":"1976","journal-title":"J Lab Clin Med"},{"key":"10.1002\/hep.1840030207-BIB13|cit13","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1042\/bj1450185","article-title":"Separation by thin-layer chromatography and structure elucidation of bilirubin conjugates isolated from dog bile","volume":"145","author":"Heirwegh","year":"1975","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB14|cit14","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1042\/bj1670001","article-title":"The isolation and further characterization of the bilirubin tetrapyrroles in bile-containing human duodenal juice and dog gall-bladder bile","volume":"167","author":"Gordon","year":"1977","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB15|cit15","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1002\/9780470110423.ch5","article-title":"Recent advances in the separation and analysis of diazo-positive bile pigments","volume":"22","author":"Heirwegh","year":"1974","journal-title":"Meth Biochem Anal"},{"key":"10.1002\/hep.1840030207-BIB16|cit16","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/0009-8981(71)90367-6","article-title":"Determination of bilirubin in liver homogenates and serum with diazotized p-iodoaniline","volume":"31","author":"Van Roy","year":"1971","journal-title":"Clin Chim Acta"},{"key":"10.1002\/hep.1840030207-BIB17|cit17","doi-asserted-by":"crossref","first-page":"2069","DOI":"10.1016\/0024-3205(74)90023-X","article-title":"Rapid transesterification of bilirubin glucuronides in methanol","volume":"15","author":"Salmon","year":"1974","journal-title":"Life Sci"},{"key":"10.1002\/hep.1840030207-BIB18|cit18","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1172\/JCI110458","article-title":"Uridine diphosphate-glucuronic acid-dependent conversion of bilirubin monoglucuronides to diglucuronide in presence of plasma membranes from rat liver is nonenzymic","volume":"69","author":"Sieg","year":"1982","journal-title":"J Clin Invest"},{"key":"10.1002\/hep.1840030207-BIB19|cit19","doi-asserted-by":"crossref","first-page":"2037","DOI":"10.1073\/pnas.76.4.2037","article-title":"Bilirubin diglucuronide synthesis by a UDP-glucuronic acid-dependent enzyme system in rat liver microsomes","volume":"76","author":"Blanckaert","year":"1979","journal-title":"Proc Natl Acad Sci USA"},{"key":"10.1002\/hep.1840030207-BIB20|cit20","doi-asserted-by":"crossref","first-page":"797","DOI":"10.1042\/bj1290797","article-title":"The ready isomerization of bilirubin-IX in aqueous solution","volume":"129","author":"McDonagh","year":"1972","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB21|cit21","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1042\/bj1730263","article-title":"Inaccuracies in measurement of conjugated and unconjugated bilirubin in bile with ethyl anthranilate diazo and solvent-partition methods","volume":"173","author":"Ostrow","year":"1978","journal-title":"Biochem J"},{"key":"10.1002\/hep.1840030207-BIB22|cit22","first-page":"381","article-title":"Excretion of conjugated bilirubin in the isolated perfused rat kidney","volume":"54","author":"Gollan","year":"1978","journal-title":"Clin Sci Molec Med"},{"key":"10.1002\/hep.1840030207-BIB23|cit23","doi-asserted-by":"crossref","first-page":"622","DOI":"10.1002\/hep.1840010610","article-title":"Bilirubin mono- and diglucuronide formation by human liver in vitro: assay by high-pressure liquid chromatography","volume":"1","author":"Chowdhury","year":"1981","journal-title":"Hepatology"},{"key":"10.1002\/hep.1840030207-BIB24|cit24","doi-asserted-by":"crossref","first-page":"2109","DOI":"10.1016\/0006-2952(79)90191-6","article-title":"Micro-analytic detection and structure elucidation of ester-glycosides","volume":"28","author":"Heirwegh","year":"1979","journal-title":"Biochem Pharmacol"},{"key":"10.1002\/hep.1840030207-BIB25|cit25","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1002\/bms.1200050707","article-title":"Rearranged glucuronic acid conjugates of bilirubin-IXa in post-obstructive bile. 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