J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M600340-JLR200 on January 12, 2007

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Journal of Lipid Research, Vol. 48, 816-825, April 2007
Copyright © 2007 by American Society for Biochemistry and Molecular Biology

Evidence for in situ ethanolamine phospholipid adducts with hydroxy-alkenals

Sandrine Bacot*, Nathalie Bernoud-Hubac*, Bernard Chantegrel{dagger}, Christian Deshayes{dagger}, Alain Doutheau{dagger}, Gabriel Ponsin*, Michel Lagarde* and Michel Guichardant1,*

* Institut National de la Santé et de la Recherche Médicale U585, Institut National des Sciences Appliquées de Lyon, Lyon, Institut Multidisciplinaire de Biochimie des Lipides, F-69621 Villeurbanne, France
{dagger} Chimie Organique, Centre National de la Recherche Scientifique, Institut National des Sciences Appliquées de Lyon, Lyon, Institut Multidisciplinaire de Biochimie des Lipides, F-69621 Villeurbanne, France

Published, JLR Papers in Press, January 12, 2007.

1 To whom correspondence should be addressed. e-mail: michel.guichardant{at}insa-lyon.fr

Hydroxy-alkenals, such as 4-hydroxy-2(E)-nonenal (4-HNE; from n-6 fatty acids), are degradation products of fatty acid hydroperoxides, including those generated by free radical attack of membrane polyunsaturated fatty acyl moieties. The cytotoxic effects of hydroxy-alkenals are well known and are mainly attributable to their interaction with different molecules to form covalent adducts. Indeed, ethanolamine phospholipids (PEs) can be covalently modified in a cellular system by hydroxy-alkenals, such as 4-HNE, 4-hydroxy-2(E)-hexenal (4-HHE; from n-3 fatty acids), and 4-hydroxy-dodecadienal (4-HDDE; from the 12-lipoxygenase product of arachidonic acid), to form mainly Michael adducts. In this study, we describe the formation of PE Michael adducts in human blood platelets in response to oxidative stress and in retinas of streptozotocin-induced diabetic rats. We have successfully characterized and evaluated, for the first time, PEs coupled with 4-HHE, 4-HNE, and 4-HDDE by gas chromatography-mass spectrometry measurement of their ethanolamine moieties. We also report that aggregation of isolated human blood platelets enriched with PE-4-hydroxy-alkenal Michael adducts was altered. These data suggest that these adducts could be used as specific markers of membrane disorders occurring in pathophysiological states with associated oxidative stress and might affect cell function.

Supplementary key words lipid peroxidation • Michael adducts • human blood platelets • rat retinas

Abbreviations: AA, arachidonic acid; DHA, docosahexaenoic acid; 4-HDDE, 4-hydroxy-2(E),6(Z)-dodecadienal; 4-HHE, 4-hydroxy-2(E)-hexenal; 4-HNE, 4-hydroxy-2(E)-nonenal; NICI, negative ion chemical ionization; PE, ethanolamine phospholipid; PRP, platelet-rich plasma; SIM, selected ion monitoring; TFAI, 1-(trifluoroacetyl)imidazole


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Copyright © 2007 by the American Society for Biochemistry and Molecular Biology.