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Journal of Lipid Research, Vol. 44, 917-926, May 2003
Copyright © 2003 by Lipid Research, Inc.

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^1,*

^* Physiologie des lipides et membranes, INSERM U585, France
Chimie Organique, INSA-Lyon, Villeurbanne, France

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

Lipid oxidation is implicated in a wide range of pathophysiogical disorders, and leads to reactive compounds such as fatty aldehydes, of which the most well known is 4-hydroxy-2E-nonenal (4-HNE) issued from 15-hydroperoxyeicosatetraenoic acid (15-HpETE), an arachidonic acid (AA) product. In addition to 15-HpETE, 12(S)-HpETE is synthesized by 12-lipoxygenation of platelet AA. We first show that 12-HpETE can be degraded in vitro into 4-hydroxydodeca-(2E,6Z)-dienal (4-HDDE), a specific aldehyde homologous to 4-HNE. Moreover, 4-HDDE can be detected in human plasma. Second, we compare the ability of 4-HNE, 4-HDDE, and 4-hydroxy-2E-hexenal (4-HHE) from n-3 fatty acids to covalently modify different ethanolamine phospholipids (PEs) chosen for their biological relevance, namely AA- (20: 4n-6) or docosahexaenoic acid- (22:6n-3) containing diacyl-glycerophosphoethanolamine (diacyl-GPE) and alkenylacyl-glycerophosphoethanolamine (alkenylacyl-GPE) molecular species. The most hydrophobic aldehyde used, 4-HDDE, generates more adducts with the PE subclasses than does 4-HNE, which itself appears more reactive than 4-HHE. Moreover, the aldehydes show higher reactivity toward alkenylacyl-GPE compared with diacyl-GPE, because the docosahexaenoyl-containing species are more reactive than those containing arachidonoyl.

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, alkenylacyl-GPEs may efficiently scavenge fatty aldehydes.

Abbreviations: AA, arachidonic acid (20:4n-6); alkenylacyl-GPE, alkenylacyl-glycerophosphoethanolamine; BSTFA, N,O-bis(trimethylsilyl)trifluoroacetamide; diacyl-GPE, diacyl-glycerophosphoethanolamine; DIBAL, diisobutylaluminium hydride; DHA, docosahexaenoic acid (22:6n-3); EI, electron ionization; FAME, fatty acid methyl ester; GC, gas chromatography; GC-MS, gas chromatography-mass spectrometry; (18:0/20:4-GPE), 1-stearoyl,2-arachidonoyl-GPE; (18:0/22:6-GPE), 1-stearoyl,2-docosahexaenoyl-GPE; (18:0p/20:4-GPE), 1-O-stearyl-1'-enyl, 2-arachidonoyl-GPE; (18:0p/22:6-GPE), 1-O-stearyl-1'-enyl,2-docosahexaenoyl-GPE; GPx, glutathione peroxidase; 4-HDDE, 4-hydroxydodeca-(2E,6Z)-dienal; 4-HHE, 4-hydroxy-2E-hexenal; 4-HNE, 4-hydroxy-2E-nonenal; HpETE, hydroperoxyeicosatetraenoic acid; NICI, negative ion chemical ionization; PE, ethanolamine phospholipid; PFB, pentafluorobenzyl; ROS, reactive oxygen species; RP-HPLC, reverse-phase HPLC; TMS, trimethylsilyl

Supplementary key words 4-hydroxydodeca-(2E,6Z)-dienal • 4-hydroxy-2E-hexenal • 4-hydroxy-2E-nonenal

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