Chemical structure of a new family of bile pigments from human urine.
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.
Yamaguchi
T
T
Department of Biochemical Genetics, Tokyo Medical and Dental University.
Shioji
I
I
Sugimoto
A
A
Komoda
Y
Y
Nakajima
H
H
D000328:Adult; D000911:Antibodies, Monoclonal; D001654:Bile Pigments / Q000737:chemistry* / Q000302:isolation & purification / Q000652:urine*; D001663:Bilirubin / Q000652:urine; D004797:Enzyme-Linked Immunosorbent Assay; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008297:Male; D011758:Pyrroles / Q000737:chemistry* / Q000302:isolation & purification / Q000652:urine*; D013056:Spectrophotometry, Ultraviolet
D000911:Antibodies, Monoclonal; D001654:Bile Pigments; D011758:Pyrroles; D001663:Bilirubin