Metabolism of polycyclic compounds. 18. The secretion of metabolites of naphthalene, 1:2-dihydronaphthalene and 1:2-epoxy-1:2:3:4-tetrahydronaphthalene in rat bile

Publisher Website
Google Scholar
Abstract
The bile of rats treated with naphthalene contains 1- and 2-naphthol, 1-naphthylglucosiduronic acid, the 1- and 2-glucosiduronic acids of trans-l,2-dihydro-l,2-dihydroxynaphthalene and 1,2-dihydroxynaphthalene, and sometimes the free dihydrodihydroxy compound. Sulphuric esters were not detected. The bile also containedS-(l,2-dihydro-2-hydroxy-l-naphthyl)glutathione, together with the corresponding S-cysteinylglycine, S-cysteine and N-acetyl-S-cysteine conjugates. Two other conjugates present in small amounts appeared to be taurine conjugates of the glutathione derivative. The bile of rats treated with 1,2-dihydro-naphthalene contained all the above naphthalene metabolites, together with S-(l,2,3,4-tetrahydro-2-hydroxy-l-naphthyl)glutathione and the corresponding S-cysteinylglycine, S-cysteine and N-acetyl-S-cysteine conjugates. An unidentified metabolite, which yielded cysteine, glycine and 2-tetralone on acid-hydrolysis, appeared to be related to the above conjugates and it was also present in the urine of animals treated with the above glutathione conjugate. The bile also contained trans-1,2,3,4-tetrahydro-1,2-dihydroxynaphthalene and its glucosiduronic acid and relatively large amounts of 2-naphthol. The bile of rats treated with l,2-epoxy-l,2,3,4-tetrahydronaphthalene contained 5 amino acid conjugates indistinguishable from those present in the bile of rats treated with 1,2-dihydronaphthalene. trans-l,2,3,4-Tetrahydro-l,2-dihydroxy-naphthalene and its glucosiduronic acid were also present. A method for the establishment of bile fistula in rats is described.