The mercapturic acid pathway metabolites of a glutathione conjugate of aflatoxin B1.
A glutathione conjugate of aflatoxin B1 (AFB1) which has previously been identified as 8,9-dihydro-8-(S-glutathionyl)-9-hydroxy aflatoxin B1 (AFB1-GSH) (E.J. Moss, D.J. Judah, M. Przybylski and G.E. Neal, Biochem. J., 210 (1983) 227-233) has been degraded in vitro to all of the intermediates of the mercapturic acid pathway (MAP) and the chromatographic and spectral characteristics of each of these compounds investigated. The cysteinylglycyl conjugate (AFB1-Cys.Gly) was prepared by incubating the AFB1-GSH conjugate with a rat hepatoma cell line rich in gamma-glutamyl-transpeptidase (GGT). Incubations of the AFB1-Cys.Gly conjugate with dipeptidase produced a metabolite, which was purified and characterized by 1H-NMR spectroscopy as 8,9-dihydro-8-(S-cysteinyl)-9-hydroxy aflatoxin B1 (AFB1-Cys). The N-acetyl derivative of the AFB1-Cys conjugate resulted from the incubation of the AFB1-GSH conjugate in vitro with isolated rat kidney cells. Mass spectral data were consistent with the compound being 8,9-dihydro-8-(S-cysteinyl-(N-acetyl))-9-hydroxy aflatoxin B1 (AFB1-Nac.Cys). A chromatographically identical compound was obtained by the chemical acetylation of AFB1-Cys.
D000111:Acetylcysteine / Q000378:metabolism*; D016604:Aflatoxin B1 / Q000031:analogs & derivatives; D000348:Aflatoxins / Q000378:metabolism*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000031:analogs & derivatives / Q000378:metabolism; D004150:Dipeptidases / Q000378:metabolism; D004151:Dipeptides / Q000378:metabolism; D005978:Glutathione / Q000031:analogs & derivatives* / Q000378:metabolism; D007668:Kidney / Q000201:enzymology / Q000378:metabolism; D008297:Male; D051381:Rats; D011916:Rats, Inbred F344; D013552:Swine
D000348:Aflatoxins; D004151:Dipeptides; C028505:cysteinylglycine; C047285:8,9-dihydro-8-(S-glutathionyl)-9-hydroxyaflatoxin B1; D016604:Aflatoxin B1; D004150:Dipeptidases; D005978:Glutathione; D003545:Cysteine; D000111:Acetylcysteine