| Covalent binding of hydroxy-alkenals 4-HDDE, 4-HHE, and 4-HNE to ethanolamine phospholipid subclasses. | |
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MedLine Citation:
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PMID: 12588949 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Sandrine Bacot; Nathalie Bernoud-Hubac; Naima Baddas; Bernard Chantegrel; Christian Deshayes; Alain Doutheau; Michel Lagarde; Michel Guichardant |
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Publication Detail:
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Type: Comparative Study; Journal Article; Research Support, Non-U.S. Gov't Date: 2003-02-16 |
Journal Detail:
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Title: Journal of lipid research Volume: 44 ISSN: 0022-2275 ISO Abbreviation: J. Lipid Res. Publication Date: 2003 May |
Date Detail:
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Created Date: 2003-05-07 Completed Date: 2004-01-23 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0376606 Medline TA: J Lipid Res Country: United States |
Other Details:
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Languages: eng Pagination: 917-26 Citation Subset: IM |
Affiliation:
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Physiologie des lipides et membranes, INSERM U585, France. |
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| MeSH Terms | |
Descriptor/Qualifier:
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Aldehydes
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chemical synthesis,
chemistry*,
metabolism Animals Binding Sites Brain / metabolism Chromatography, High Pressure Liquid Eicosapentaenoic Acid / chemistry Gas Chromatography-Mass Spectrometry Humans Phosphatidylethanolamines / chemistry*, metabolism Phospholipids / chemistry, metabolism Rats Time Factors |
| Chemical | |
Reg. No./Substance:
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0/4-hydroxydodeca-2,6-dienal; 0/Aldehydes; 0/Phosphatidylethanolamines; 0/Phospholipids; 1553-41-9/Eicosapentaenoic Acid; 17427-08-6/4-hydroxy-2-hexenal; 29343-52-0/4-hydroxy-2-nonenal |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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