Identification of novel bioactive aldehyde-modified phosphatidylethanolamines formed by lipid peroxidation.

Guo L, Chen Z, Amarnath V, Davies SS
Free Radic Biol Med. 2012 53 (6): 1226-38

PMID: 22898174 · PMCID: PMC3461964 · DOI:10.1016/j.freeradbiomed.2012.07.077

Lipid aldehydes generated by lipid peroxidation induce cell damage and inflammation. Recent evidence indicates that γ-ketoaldehydes (isolevuglandins, IsoLGs) form inflammatory mediators by modifying the ethanolamine headgroup of phosphatidylethanolamines (PEs). To determine if other species of aldehyde-modified PEs (al-PEs) with inflammatory bioactivity were generated by lipid peroxidation, we oxidized liposomes containing arachidonic acid and characterized the resulting products. We detected PE modified by IsoLGs, malondialdehyde (MDA), and 4-hydroxynonenal (HNE), as well as a novel series of N-acyl-PEs and N-carboxyacyl-PEs in these oxidized liposomes. These al-PEs were also detected in high-density lipoproteins exposed to myeloperoxidase. When we tested the ability of al-PEs to induce THP-1 monocyte adhesion to cultured endothelial cells, we found that PEs modified by MDA, HNE, and 4-oxononenal induced adhesion with potencies similar to those of PEs modified by IsoLGs (∼2μM). A commercially available medium-chain N-carboxyacyl-PE (C11:0CAPE) also stimulated adhesion, whereas C4:0CAPE and N-acyl-PEs did not. PEs modified by acrolein or by glucose were only partial agonists for adhesion. These studies indicate that lipid peroxidation generates a large family of al-PEs, many of which have the potential to drive inflammation.

Copyright © 2012 Elsevier Inc. All rights reserved.

MeSH Terms (16)

Aldehydes Analysis of Variance Arachidonic Acid Cells, Cultured Humans Human Umbilical Vein Endothelial Cells Inflammation Mediators Lipid Peroxidation Lipoproteins, HDL Liposomes Malondialdehyde Oxidation-Reduction Oxidative Stress Phosphatidylethanolamines Prostaglandins Tandem Mass Spectrometry

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