Metabolism of polycyclic compounds. 17. The reaction of 1:2-dihydronaphthalene and 1:2-epoxy-1:2:3:4-tetrahydronaphthalene with glutathione catalysed by tissue preparations

Publisher Website
Google Scholar
Abstract
The preparation of S-(2-hydroxy-l,2,3,4-tetrahydro-l-naphthyl)glutathione (I) is described. 1,2-Dihydronaphthalene was converted by rat-liver slices into the glutathione derivative (I), which, with rat-kidney homogenate, yielded S-(2-hydroxy-1,2,3,4-tetrahydro-l-naphthyl)-L-cysteine (II) and with rat-kidney slices yielded N-acetyl-S-(2-hydroxy-l,2,3,4-tetrahydro-l-naphthyl)-L-cysteine (III). Trans-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene and 2-naphthol were also formed by the action of rat-liver slices on 1,2-dihydronaph-thalene. A rat-liver microsomal system converted 1,2-dihydronaph-thalene into trans-l,2-dihydroxy-l,2,3,4-tetrahydronaphthalene, and, in the presence of glutathione, cysteine or N-acetylcysteine, to the respective S-(2-hydroxy- 1,2,3,4-tetrahydro-l-naphthyl) derivatives (I), (II) or (HI). The formation of the glutathione derivative (I), but not of the derivatives (II) and (III), was increased by the addition of supernatant from the preparation of the microsomes. The addition of glutathione to l,2-epoxy-l,2,3,4-tetrahydronaphthalene was increased in the presence of the supernatant fraction of rat liver, whereas the addition of cysteine and N-acetylcysteine to the epoxide was not affected. The supernatant fraction of a rat-liver homogenate in 0.1 [image]-phosphate buffer, pH 7.4, appears to contain an enzyme which activates glutathione.