13-Oxo-ODE is an endogenous ligand for PPARgamma in human colonic epithelial cells

Biochem Pharmacol. 2007 Aug 15;74(4):612-22. doi: 10.1016/j.bcp.2007.05.027. Epub 2007 Jun 7.

Abstract

Background: The ligand activated nuclear hormone receptor peroxisome proliferator-activated receptor gamma (PPARgamma) induces transcriptional repression of pro-inflammatory factors. Activation of PPARgamma is followed by amelioration of colitis in animal models of inflammatory bowel disease (IBD). A reduced expression of PPARgamma was found in epithelial cells of patients with ulcerative colitis. The eicosanoids 13-HODE and 15-HETE are products of 12/15-lipoxygenase (LOX) and endogenous ligands for PPARgamma. Dehydrogenation of 13-HODE by 13-HODE dehydrogenase results in formation of the 13-Oxo-ODE. Highest activity of 13-HODE dehydrogenase is found in colonic epithelial cells (CECs). We therefore investigated whether 13-Oxo-ODE is a new endogenous ligand of PPARgamma in CECs.

Methods: LOX activity and 13-HODE dehydrogenase in CECs were investigated after stimulation with arachidonic or linoleic acid. LOX metabolites were identified by RP-18 reversed-phase HPLC. Binding of (14)C-labelled 13-Oxo-ODE was demonstrated using a His-tagged PPARgamma.

Results: Stimulation of HT-29 and primary CECs homogenates with and without Ca-ionophor was followed by the formation of high amounts of the linoleic acid metabolite 13-Oxo-ODE (155 and 85 ng/ml). The decrease of IL-8 secretion from IEC was more pronounced after pre-incubation with 13-Oxo-ODE compared to the PPARgamma agonist troglitazone and higher as with the known PPARgamma ligands 13-HODE and 15-HETE. Binding assays with (14)C-labelled 13-Oxo-ODE clearly demonstrated a direct interaction.

Conclusion: High amounts of 13-Oxo-ODE can be induced in CECs by stimulation of linoleic acid metabolism. 13-Oxo-ODE binds to PPARgamma and has anti-inflammatory effects. 13-HODE dehydrogenase might be a therapeutic target in IBD.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arachidonic Acid / metabolism
  • Arachidonic Acid / pharmacology
  • Blotting, Western
  • Carbon Radioisotopes
  • Cattle
  • Chromatography, High Pressure Liquid
  • Colon / metabolism
  • Colon / pathology
  • Epithelial Cells / drug effects
  • Epithelial Cells / metabolism*
  • Epithelial Cells / pathology
  • HT29 Cells
  • Humans
  • Hydroxyeicosatetraenoic Acids / pharmacology
  • Immunoprecipitation
  • Interleukin-8 / metabolism
  • Ligands*
  • Linoleic Acid / metabolism
  • Linoleic Acid / pharmacology
  • Linoleic Acids / pharmacology
  • Linolenic Acids / chemistry
  • Linolenic Acids / metabolism*
  • Linolenic Acids / pharmacology
  • Molecular Structure
  • PPAR gamma / genetics
  • PPAR gamma / metabolism*
  • Protein Binding / drug effects
  • Reverse Transcriptase Polymerase Chain Reaction
  • Spectrometry, Mass, Electrospray Ionization
  • Transfection

Substances

  • Carbon Radioisotopes
  • Hydroxyeicosatetraenoic Acids
  • Interleukin-8
  • Ligands
  • Linoleic Acids
  • Linolenic Acids
  • PPAR gamma
  • Arachidonic Acid
  • 13-oxo-9,11-octadecadienoic acid
  • 5-hydroxy-6,8,11,14-eicosatetraenoic acid
  • 13-hydroxy-9,11-octadecadienoic acid
  • 15-hydroxy-5,8,11,13-eicosatetraenoic acid
  • Linoleic Acid