A hydrophilic tetrahydro-beta-carboline in human urine.
A substance that exhibited a tryptophan-like fluorescence peak at 354 nm on excitation at 295 nm at neutral pH was isolated from human urine. This compound was determined by visible-light absorption spectroscopy, fluorescence spectroscopy, 1H and 13C NMR spectroscopies, and FAB-MS to be 1-(1',2',3',4',5'-pentahydroxypentyl)-1,2,3,4-tetrahydro-2-carboli ne-3- carboxylic acid. This compound, named tetrahydropentoxyline, is a new type of hydrophilic tetrahydro-beta-carboline, and its elution position was between those of 4-pyridoxic acid and kynurenic acid on C18 reversed-phase HPLC. The amount of tetrahydropentoxyline excreted in the urine of normal subjects [n = 21; age, 45 (SD 20) years] was about 5.2 (SD 1.0) mg per day.
Horiuchi
K
K
Department of Chemistry, Hamamatsu University School of Medicine, Shizuoka.
Yonekawa
O
O
Iwahara
K
K
Kanno
T
T
Kurihara
T
T
Fujise
Y
Y
D002243:Carbolines / Q000652:urine*; D002851:Chromatography, High Pressure Liquid; D003924:Diabetes Mellitus, Type 2 / Q000652:urine*; D005260:Female; D006801:Humans; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D012016:Reference Values; D012995:Solubility; D013050:Spectrometry, Fluorescence; D016339:Spectrometry, Mass, Fast Atom Bombardment
D002243:Carbolines; C087650:tetrahydropentoxyline; C009804:tryptoline