New products in the hepoxilin pathway: Isolation of 11-glutathionyl hepoxilin A3 through reaction of hepoxilin A3 with glutathione S-transferase

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Abstract

We describe herein the metabolism of hepoxilin A3 (HxA3) by glutathione S-transferase (GST) into a glutathione conjugate. The reaction was carried out with HxA3 (unlabelled and 14C-labelled) and glutathione (unlabelled and tritium labelled). When two isomers of HxA3 were reacted with GST, two products were formed. Only one product was formed when a single isomer of HxA3 was used. The isomeric product HxB3 was marginally active indicating considerable specificity in the reaction with GST. The products were characterized by retention of tritium from glutathione and by comparison of their migration on high performance liquid chromatography with authentic reference compounds. The products bear the structure, 11-glutathionyl HxA3.

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    Hepoxilin A3 is subject to metabolism through the glutathione S-transferase route as is known for the leukotrienes [112–116]. This transformation into glutathionyl hepoxilin A3 (named hepoxilin A3-C in keeping with the leukotriene nomenclature) is carried out by enzymes in the liver [26] and enzyme activity has been ascribed to isozymes containing the Yb2 subunit and not the Ya or Yc subunit [24]. Hepoxilin A3-C was formed in rat hippocampal slices in the presence of the epoxide inhibitor, TCPO thereby blocking the transformation of the hepoxilin A3 precursor into the inactive trihydroxy metabolite.

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