J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
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A more recent version of this article appeared on May 1, 2003

Papers In Press, published online ahead of print February 16, 2003
J. Lipid Res., doi:10.1194/jlr.M200450-JLR200
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Submitted on November 27, 2002
Revised on February 4, 2003
Accepted on February 5, 2003

Covalent binding of hydroxy-alkenals (4-HDDE, 4-HHE and 4-HNE) to ethanolamine phospholipid subclasses

Sandrine Bacot, Nathalie Bernoud-Hubac, Naïma Baddas, Bernard Chantegrel, Christian Deshayes, Alain Doutheau, Michel Lagarde, and Michel Guichardant

Biochemistry Dept., INSA / INSERM U 585, Villeurbanne 69621

Corresponding Author: Michel.Guichardant{at}insa-lyon.fr

Lipid oxidation is implicated in a wide range of pathophysiogical disorders, which leads to reactive compounds such as fatty aldehydes, the most well-known being 4-hydroxynonenal (4-HNE) issued from 15-hydroperoxyeicosatetraenoic acid (15-HpETE), an arachidonic acid product. In addition to 15-HpETE, 12(S)-HpETE is synthesized by 12-lipoxygenation of platelet arachidonic acid. We first show that 12-HpETE can be degraded in vitro into 4-hydroxydodecadienal (4-HDDE), a specific aldehyde homologous to 4-HNE. Moreover, 4-HDDE can be detected in human plasma. Secondly, we compared the ability of 4-HNE, 4-HDDE and 4-hydroxyhexenal (4-HHE) from n-3 fatty acids to covalently modify different ethanolamine phospholipids (PE) chosen for their biological relevance, namely arachidonoyl- (20:4n-6) or docosahexaenoyl- (22:6n-3) containing diacyl-glycerophosphoethanolamine (diacyl-GPE) and alkenylacyl-GPE (plasmalogen PE) molecular species. 4-HDDE, the most hydrophobic aldehyde used, generates more adducts with the PE subclasses than 4-HNE, which itself appears more reactive than 4-HHE. Moreover, the aldehydes show higher reactivity toward plasmalogen PE compared to diacyl-GPE, the docosahexaenoyl-containing species being more reactive than the arachidonoyl-containing ones. We conclude that the different PE species are differently targeted by fatty aldehydes, the higher their hydrophobicity, the higher the amount of adducts made. In addition to their antioxidant potential, plasmalogen PE may efficiently scavenge fatty aldehydes.


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