Biotransformation of diethenylbenzenes. IV. A simple high-performance liquid chromatographic method for separation of urinary metabolites of 1,3-diethenylbenzene on analytical and semi-preparative scales.
A simple ion-suppression separation on reversed-phase columns, which is applicable for both analytical and semi-preparative work, is described. Six urinary metabolites of 1,3-diethenylbenzene (I), namely 1-(3-ethenylphenyl)-1,2-dihydroxyethane beta-D-glucosiduronates (two isomers, II and III), N-acetyl-S-[1-(3-ethenylphenyl)-2-hydroxyethyl]cysteine (IV), N-acetyl-S-[2-(3-ethenylphenyl)-2-hydroxyethyl]cysteine (V), 3-ethenylphenylmandelic acid (VI) and 3-ethenylphenylglyoxylic acid (VII), were isolated (Fig. 1). Four of them, IV-VII, have been identified in our previous work; the two glucosiduronates were identified for the first time by 1H NMR spectroscopy, fast atom bombardment mass spectrometry, and enzymic hydrolysis yielding 1-(3-ethenylphenyl)-1,2-dihydroxyethane as an aglycone. The method was reproducible the concentration range 0.05-5 mg/ml, the coefficient of variation being less than 7% (n = 5). Excretion of II-VI within 24 h in the urine of rats dosed with a single intraperitoneal injection of 100, 300 and 600 mg/kg I was determined quantitatively. The utility of the method is discussed in comparison with gas chromatographic-mass spectrometric techniques used previously.
Linhart
I
I
National Institute of Public Health, Centre of Industrial Hygiene and Occupational Diseases, Prague, Czechoslovakia.
Vosmanská
M
M
Mitera
J
J
Smejkal
J
J
D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D051381:Rats; D017208:Rats, Wistar; D015203:Reproducibility of Results; D013056:Spectrophotometry, Ultraviolet; D013343:Styrenes / Q000302:isolation & purification / Q000378:metabolism* / Q000493:pharmacokinetics / Q000652:urine
D013343:Styrenes; C076011:1,3-diethenylbenzene