Document Detail

F4-isoprostanes: a novel class of prostanoids formed during peroxidation of docosahexaenoic acid (DHA).
MedLine Citation:
PMID:  9446796     Owner:  NLM     Status:  MEDLINE    
Isoprostanes are prostaglandin (PG)-like compounds derived from free radical-catalyzed peroxidation of polyunsaturated fatty acids. F2-isoprostanes are produced in vivo by a non-cyclooxygenase mechanism involving free radical peroxidation of arachidonic acid. Peroxidation of eicosapentaenoic acid produces F3-isoprostanes. In this study, we explore the possibility of formation of F4-isoprostanes during peroxidation of docosahexaenoic acid (DHA) in vitro. DHA-liposomes were exposed at 37 degrees C to either 2,2'-azobis-(2-amidinopropane) hydrochloride (AAPH) or copper ions at final concentrations of 10 mM and 50 microM, respectively. Sample processing involved solid-phase extraction on a C18 and an NH2- cartridge. After conversion to pentafluorobenzyl ester and trimethylsilyl derivatives, F4-isoprostanes were analysed by negative ion-chemical ionisation mass spectrometry using tetradeuterated PGF2 alpha (PGF2-d4) as the internal standard. Quantitative analysis was carried out by selected ion monitoring (SIM) of the carboxylated anion [M-180]- at m/z 593 and 573 for the F4-isoprostanes and PGF2-d4, respectively. DHA oxidised by AAPH or by copper ions gave rise to a similar family of F4-isoprostanes. Formation of F4-isoprostanes increased throughout the oxidation period and was correlated with other indices of lipid peroxidation (hydroperoxides and thiobarbituric acid reactive substances). The possibility of analyzing F4-isoprostanes should provide new opportunities for studying the role of lipid peroxidation in nutritional studies and in the pathogenesis of neurodegenerative diseases.
J Nourooz-Zadeh; E H Liu; E Anggård; B Halliwell
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biochemical and biophysical research communications     Volume:  242     ISSN:  0006-291X     ISO Abbreviation:  Biochem. Biophys. Res. Commun.     Publication Date:  1998 Jan 
Date Detail:
Created Date:  1998-02-27     Completed Date:  1998-02-27     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0372516     Medline TA:  Biochem Biophys Res Commun     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  338-44     Citation Subset:  IM    
Centre for Clinical Pharmacology and Therapeutic Toxicology, Department of Medicine, London, England.
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MeSH Terms
Amidines / metabolism
Chromatography, High Pressure Liquid
Copper / metabolism
Docosahexaenoic Acids / metabolism*
Lipid Peroxidation / physiology*
Liposomes / metabolism
Mass Spectrometry
Molecular Structure
Oxidants / metabolism
Prostaglandins / analysis,  chemistry*
Thiobarbituric Acid Reactive Substances / analysis
Time Factors
Reg. No./Substance:
0/Amidines; 0/Liposomes; 0/Oxidants; 0/Prostaglandins; 0/Thiobarbituric Acid Reactive Substances; 13217-66-8/2,2'-azobis(2-amidinopropane); 25167-62-8/Docosahexaenoic Acids; 7440-50-8/Copper

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