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Chemical Structure of a New Family of Bile Pigments from Human Urine
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1994
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Bioorganic ChemistryMetabolomic ProfilingSecondary MetaboliteBile PigmentsChemical BiologyMedicinal ChemistryBioanalysisAnalytical ChemistryClinical ChemistryBiochemistryChemical PathologyMetabolomicsPharmacologyPrimary MetaboliteBiomolecular EngineeringHuman UrineNew FamilyBiliary TractNatural SciencesSeven Bilirubin MetabolitesBilirubin MetabolitesMedicineDrug DiscoveryPigmentDrug Analysis
Seven bilirubin metabolites negative to the diazo reaction were identified in the urine of healthy persons by enzyme-linked immunosorbent assay (ELISA) using the anti-bilirubin monoclonal antibody 24G7. Two of the seven metabolites were isolated and their chemical structures were determined using fast-atom bombardment-mass spectroscopy (FAB-MS) and 1H-NMR. The two metabolites are 1,14,15,17-tetrahydro-2,7,13-trimethyl-1,14- dioxo-3-vinyl-16H-tripyrrin-8,12-dipropionic acid and 1,14,15,17-tetrahydro-3,7,13-trimethyl-1,14-dioxo-2-vinyl-16H- tripyrrin-8,12-dipropionic acid. They are regioisomers of each other. The two bilirubin metabolites are novel tripyrrole biocompounds and belong to a third group of bile pigments following biliverdin and bilirubin. We gave these compounds the generic names biotripyrrin-a and biotripyrrin-b, respectively.