scholarly journals Bilirubin conjugates in bile of man, rat and dog. Semi-quantitative analysis of bile composition by thin-layer chromatography

1976 ◽  
Vol 155 (2) ◽  
pp. 365-373 ◽  
Author(s):  
B A. Noir
Keyword(s):  
Gall Bladder ◽  
Glucuronic Acid ◽  
Bile Pigments ◽  
Human Bile ◽  
Bile Composition ◽  
Hexuronic Acid ◽  
Normal Rat ◽  
Phenol Water ◽  
Layer Chromatography ◽  
Rat Bile

1. Conjugated bile pigments, separated in two fractions by semi-quantitative t.l.c. performed on silicic acid with phenol/water as the developing solvent, were treated with diazotized ethyl anthranilate. Resulting dipyrrylazo derivatives were analysed by quantitative t.l.c. 2. The tentative structure elucidation of tetrapyrrolic bilirubin conjugates and semi-quantitative evaluation of rat bile, post-obstructive human bile and dog bile composition is presented. 3. Homogeneous and mixed hexuronic acid diesters of bilirubin containing glucuronic acid constitute 51% of the total conjugates in normal rat bile, 45% of those in human post-obstructive bile and 38% of those in obstructed rat biles. 4. Monoconjugated bilirubin amounts to 33% of total conjugated bile pigments in normal rat bile, and 17 and 14% in post-obstructive hepatic human bile and gall-bladder bile of dog respectively. After loading with unconjugated bilirubin a greater amount of monoconjugates (56%) occur in the rat bile, whereas bilirubin diglucuronide excretion is decreased (34%). 5. In gall-bladder bile of normal dog, 40% of glucose-containing diconjugates, 32% of homogeneous and/or mixed hexuronic acid (mainly glucuronic acid) diesters of bilirubin and 14% of xylose-containing diconjugates are estimated. 6. Increased amounts of bilirubin conjugates, including some with unidentified uronic acid groups, were observed in cholestatic rat biles and quantities of conjugates with glucuronic acid were decreased.

scholarly journals An accurate and sensitive analysis by high-pressure liquid chromatography of conjugated and unconjugated bilirubin IX-α in various biological fluids

1980 ◽  
Vol 185 (1) ◽  
pp. 281-284 ◽  
Author(s):  
S Onishi ◽  
S Itoh ◽  
N Kawade ◽  
K Isobe ◽  
S Sugiyama
Keyword(s):  
High Pressure ◽  
Liquid Chromatography ◽  
High Pressure Liquid Chromatography ◽  
Glucuronic Acid ◽  
Biological Fluids ◽  
Reversed Phase ◽  
Complete Separation ◽  
Bile Pigments ◽  
Human Bile ◽  
Neonatal Liver

An accurate and sensitive method was developed for the complete separation of the native tetrapyrroles, such as bilirubin and its mono- and di-conjugates of glucuronic acid, glucose and xylose, by ion-pair reversed-phase high-pressure liquid chromatography. The application of this method was demonstrated by the analysis of bile pigments in human bile and urine, and the method also makes it possible to estimate very low UDP-glucuronyltransferase activity, such as is found in the human foetal and neonatal liver.

scholarly journals Mass-spectrometric study of the azopigments obtained from bile pigments with diazotized ethyl anthranilate

1970 ◽  
Vol 120 (4) ◽  
pp. 891-894 ◽  
Author(s):  
F. Compernolle ◽  
F. H. Jansen ◽  
K. P. M. Heirwegh
Keyword(s):  
Mass Spectrometry ◽  
Mass Spectrum ◽  
Mass Spectra ◽  
Mass Spectrometric Study ◽  
Side Chain ◽  
Bile Pigments ◽  
Trimethylsilyl Derivative ◽  
Spectrometric Study ◽  
Human Bile ◽  
Rat Bile

The structures of some azopigments obtained by diazotization of conjugated and unconjugated bile pigments with diazotized ethyl anthranilate were studied by mass spectrometry. The α0-azopigments derived from rat bile and human bile were shown to be identical (t.l.c. and mass spectra) with azobilirubin derived from unconjugated bilirubin. The presence of two methyl vinyl isomers (Ia) and (Ib) in equal amounts was shown by t.l.c. and mass spectrometry. The structure of the δ-azopigment derived from rat bile was studied by two methods: (a) ammonolysis gave rise to an amide having a CH2·CH2·CO·NH2 side chain as shown by its mass spectrum; (b) the mass spectrum of a trimethylsilyl derivative of the δ-azopigment methyl ester confirmed the ester to be a β-d-monoglucuronide ester of azobilirubin I.

scholarly journals Structure revision of disaccharidic conjugates of bilirubin-IX α in human bile and identification of phenylazo derivatives B4, B5, and B6 as 2-, 3- and 4-O-acylglucuronides

1978 ◽  
Vol 175 (3) ◽  
pp. 1095-1101 ◽  
Author(s):  
F Compernolle
Keyword(s):  
Mass Spectrometry ◽  
Glucuronic Acid ◽  
Chain Structure ◽  
Positional Isomers ◽  
Human Bile ◽  
Hexuronic Acid ◽  
Structure Revision ◽  
Branched Chain ◽  
Trimethylsilyl Derivatives

Aniline azopigments B4, B5 and B6, derived from conjugates of bilirubin-IX alpha in human bile, and previously characterized as disaccharidic esters [Kuenzle (1970) Biochem. J. 119, 387-394 and 411-435], were analysed by using t.l.c. and mass spectrometry. The compounds were identified as partially separated mixtures of 2-, 3- and 4-O-acylglucuronide positional isomers. The 1-O-acylglucuronide was not detected in the mixtures and was the only compound hydrolysed with beta-glucuronidase. Further scrutiny of structural assignments made by Kuenzle [(1970) Biochem. J. 119, 411-435] led to identification of the lactone and hexuronic acid derivatives that were obtained from azopigment B5 along with glucuronolactone and glucuronic acid. A branched-chain structure, i.e. 3-C-hydroxy-methyl-D-riburonic acid, was assigned previously, but the derivatives have now been identified as various incompletely silylated forms of glucuronolactone and glucuronic acid. Several trimethylsilyl derivatives glucuronolactone were isolated and characterized by n.m.r. and mass spectrometry.

scholarly journals Separation by thin-layer chromatography and structure elucidation of bilirubin conjugates isolated from dog bile

1975 ◽  
Vol 145 (2) ◽  
pp. 185-199 ◽  
Author(s):  
K P Heirwegh ◽  
J Fevery ◽  
R Michiels ◽  
G P van Hees ◽  
F Compernolle
Keyword(s):  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Alkaline Medium ◽  
Structure Elucidation ◽  
Glucuronic Acid ◽  
Structural Information ◽  
Bile Pigments ◽  
Ester Linkage ◽  
Layer Chromatography ◽  
Isomer Determination

1. A system for separation of bile pigments by t.l.c. and for their structure elucidation is presented. Separated bile pigments are characterized by t.l.c. of derived dipyrrolic azopigments. 2. At the tetrapyrrolic stage hydrolysis in strongly alkaline medium followed by t.l.c. demonstrates the presence of bilirubin-IIIalpha, -IXalpha and -XIIIalpha and allows assessment of their relative amounts. 3. Most structural information is derived from analysis of dipyrrolic azopigments. Such derivatives, obtained by treatment of separated bile pigments with diazotized ethyl anthranilate, were separated and purified by t.l.c. Micro methods showed (a) the nature of the dipyrrolic aglycone, (b) the nature of the bonds connecting aglycone to a conjugating group, (c) the ratio of vinyl/isovinyl isomers present in the aglycone and, (d) the nature of the conjugating groups (by suitable derivative formation and t.l.c. with reference to known compounds). 4. In bile of normal dogs at least 20 tetrapyrrolic, diazo-positive bile pigments could be recognized. Except for two pigments the tetrapyrrolic nucleus corresponded predominantly to bilirubin-IXalpha. All conjugated pigments had their conjugating groups connected in ester linkage to the tetrapyrrolic aglycone, Apart from bilirubin-IXalpha, monoconjugates and homogeneous and mixed diconjugates of bilirubin were demonstrated; conjugating groups of major importance were xylose, glucose and glucuronic acid. 5. Bilirubin isomer determination on native bile and isolated bile pigments, and dipyrrole-exchange assays with [14C8]bilirubin indicated (a) that the conjugates pre-exist in bile, and (b) that no significant dipyrrole exchange occurs during isolation of the pigments.

scholarly journals Conjugated and unconjugated bilirubins in bile of humans and rhesus monkeys. Structure of adult human and rhesus-monkey bilirubins compared with dog bilirubins

1977 ◽  
Vol 167 (3) ◽  
pp. 535-548 ◽  
Author(s):  
S G Blumenthal ◽  
D B Taggart ◽  
R Ikeda ◽  
B H Ruebner ◽  
D E Bergstrom
Keyword(s):  
Chemical Composition ◽  
Gall Bladder ◽  
Rhesus Monkey ◽  
Rhesus Monkeys ◽  
Glucuronic Acid ◽  
Unknown Compound ◽  
Adult Human ◽  
Adult Humans ◽  
Technical Modifications ◽  
Working Day

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).

scholarly journals V. An account some experiments made with the bile of persons dead of the plague at Marseilles, with what appear'd upon the dissection of the bodies; as likewise some experiments made with the bile of persons dead of other diseases

1723 ◽  
Vol 32 (370) ◽  
pp. 20-32
Keyword(s):  
Gall Bladder ◽  
Human Bile

The Human Bile, taken from the Gall-Bladder of the Bodies of those that dy'd of the Plague at Marseilles , has been always found to be of a black and greenish Colour.

scholarly journals The effects of short term lipid infusion on plasma and hepatic bile lipids in humans

Gut ◽  
1999 ◽  
Vol 45 (3) ◽  
pp. 453-458 ◽  
Author(s):  
R Pakula ◽  
F M Konikoff ◽  
A M Moser ◽  
F Greif ◽  
A Tietz ◽  
...  
Keyword(s):  
Gall Bladder ◽  
Lipid Emulsions ◽  
Medium Chain Triglycerides ◽  
Hepatic Bile ◽  
Lipid Infusion ◽  
Bile Composition ◽  
Medium Chain ◽  
Increased Risk ◽  
Long Chain Triglycerides ◽  
Long Chain

BACKGROUNDPatients on parenteral nutrition have an increased incidence of gall bladder sludge and gallstone disease, thought to be related to bile stasis. Intravenous lipid emulsions, especially those containing medium chain triglycerides, have also been shown to have a lithogenic effect on the composition of bile in the gall bladder.AIMSTo determine whether lipid infusion influences hepatic bile composition in patients with an indwelling T tube following cholecystectomy and choledochotomy.METHODSIn eight patients undergoing the above surgical procedure, the time at which effects of the interrupted enterohepatic circulation were minimal was determined. Twenty two cholesterol gallstone patients with bile fistula were then randomised to receive an infusion of a lipid emulsion containing either long chain triglycerides or a mixture of long and medium chain triglycerides.RESULTSLipid infusion resulted in a significant increase in plasma levels of triglycerides and phospholipids. Both lipid emulsions caused an increase in hepatic biliary cholesterol level and cholesterol saturation index, but this effect was more pronounced with medium chain triglycerides. The fatty acid composition of biliary phospholipids showed a significant enrichment of linoleic acid by both lipid infusions.CONCLUSIONSInfusion of triglycerides causes lithogenic changes in hepatic bile composition in humans, the lithogenic effect of infusion of medium chain triglycerides being more pronounced than that of long chain triglycerides. This effect, coupled with gall bladder stasis, may be responsible for the increased risk of biliary sludge and gallstone formation in patients on long term lipid infusion.

Carbohydrate Moieties of Glycoproteins in Human Hepatic and Gall-Bladder Bile, Gall-Bladder Mucosa and Gall Stones

1979 ◽  
Vol 56 (6) ◽  
pp. 533-538 ◽  
Author(s):  
S. P. Lee ◽  
T. H. Lim ◽  
A. J. Scott
Keyword(s):  
Liquid Chromatography ◽  
Gall Bladder ◽  
Mixed Micelles ◽  
Gas Liquid Chromatography ◽  
Variable Amount ◽  
Bladder Mucosa ◽  
Human Bile ◽  
Acetylneuraminic Acid ◽  
Gall Stones ◽  
Cholesterol Solubilization

1. The soluble glycoproteins of human bile, gall-bladder mucosa and gall stones have been extracted and hydrolysed, and the monosaccharides analysed by gas-liquid chromatography. 2. Human biliary glycoproteins contained 55–75% of carbohydrate, the major monosaccharide components being galactose, fucose and N-acetylglucosamine, accounting for 70–85% of all the monosaccharides. Mannose, glucose, N-acetylgalactosamine and N-acetylneuraminic acid (sialic acid) were also present. N-Acetylneuraminic acid was present in large amounts in the gall-bladder mucosa and bile of one ulcerated and markedly inflamed gall bladder. 3. The proportion of monosaccharides in soluble glycoproteins of mucosa and bile were not different in samples from subjects with or without gall stones. 4. Gall stones were analysed for cholesterol, calcium and bilirubin and classified as ‘cholesterol stones’ (7/10) and ‘pigment stones’ (3/10). Both cholesterol and pigment stones contain a variable amount of glycoprotein. The pattern of carbohydrate constituents was similar to that present in the gall-bladder mucosa and bile in the same subject. There was also no major difference between the pattern found in ‘cholesterol’ and ‘pigment’ stones. 5. Evidence and argument are presented suggesting that some glycoprotein is secreted by the gall bladder and incorporated into gall stones. This calls for further work upon the influence of these carbohydrate-rich macromolecules on cholesterol solubilization in mixed micelles.

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