HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text Full Text (PDF) All Versions of this Article: M200450-JLR200v1 44/5/917    most recent Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Request Permissions Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Bacot, S. Articles by Guichardant, M. Search for Related Content PubMed PubMed Citation Articles by Bacot, S. Articles by Guichardant, M. Social Bookmarking                      What's this?

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

CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				C. Marantos, V. Mukaro, J. Ferrante, C. Hii, and A. Ferrante Inhibition of the Lipopolysaccharide-Induced Stimulation of the Members of the MAPK Family in Human Monocytes/Macrophages by 4-Hydroxynonenal, a Product of Oxidized Omega-6 Fatty Acids Am. J. Pathol., October 1, 2008; 173(4): 1057 - 1066. [Abstract] [Full Text] [PDF]

				T. Ruf and W. Arnold Effects of polyunsaturated fatty acids on hibernation and torpor: a review and hypothesis Am J Physiol Regulatory Integrative Comp Physiol, March 1, 2008; 294(3): R1044 - R1052. [Abstract] [Full Text] [PDF]

				S. Bacot, N. Bernoud-Hubac, B. Chantegrel, C. Deshayes, A. Doutheau, G. Ponsin, M. Lagarde, and M. Guichardant Evidence for in situ ethanolamine phospholipid adducts with hydroxy-alkenals J. Lipid Res., April 1, 2007; 48(4): 816 - 825. [Abstract] [Full Text] [PDF]