Novel glutathione conjugates formed from epoxyeicosatrienoic acids (EETs)

Arch Biochem Biophys. 1985 Oct;242(1):225-30. doi: 10.1016/0003-9861(85)90496-5.

Abstract

The catalysis of glutathione (GSH) conjugation to epoxyeicosatrienoic acids (EETs) by various purified isozymes of glutathione S-transferase was studied. A GSH conjugate of 14,15-EET was isolated by HPLC and TLC; this metabolite contained one molecule of EET and one molecule of GSH. Fast atom bombardment mass spectrometry of the isolated metabolite confirmed the structure as a GSH conjugate of 14,15-EET. Studies designed to determine the isozyme specificity of this reaction demonstrated that two isozymes, 3-3, and 5-5, efficiently catalyzed this conjugation reaction. The Km values for 14,15-EET were approximately 10 microM and the Vmax values ranged from 25 to 60 nmol conjugate formed min-1 mg-1 purified transferase 3-3 and 5-5. The 5,6-, 8,9-, and 11,12-EETs were also substrates for the reaction, albeit at lower rates. These results demonstrate that the EETs can serve as substrates for the cytosolic glutathione S-transferases.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 8,11,14-Eicosatrienoic Acid / analogs & derivatives
  • 8,11,14-Eicosatrienoic Acid / metabolism*
  • Animals
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Fatty Acids, Unsaturated / metabolism*
  • Glutathione / metabolism*
  • Glutathione Transferase / metabolism
  • Isoenzymes / metabolism
  • Kinetics
  • Male
  • Mass Spectrometry
  • Rats
  • Rats, Inbred Strains
  • Substrate Specificity

Substances

  • Fatty Acids, Unsaturated
  • Isoenzymes
  • 5,6-epoxy-8,11,14-eicosatrienoic acid
  • Glutathione Transferase
  • 8,11,14-Eicosatrienoic Acid
  • Glutathione