Document Detail

Analysis of epoxyeicosatrienoic and monohydroxyeicosatetraenoic acids esterified to phospholipids in human red blood cells by electrospray tandem mass spectrometry.
MedLine Citation:
PMID:  9269087     Owner:  NLM     Status:  MEDLINE    
Electrospray ionization (ESI) and tandem mass spectrometry (MS/MS) were used to analyze epoxyeicosatrienoic acids (EETs) and monohydroxyeicosatetraenoic acids (HETEs) isolated from human red blood cell membranes following base hydrolysis. ESI results in the formation of an abundant isobaric carboxylate anion at m/z 319 for both of these oxidized metabolites of arachidonic acid. The product ion spectra from the collision-induced dissociation of this carboxylate anion could be used to identify each of the isomeric eicosanoids from the unique fragment ions of each eicosanoid. The observed product ion spectra were identical with those previously obtained by fast atom bombardment ionization; however, ESI required less EET and HETE for analysis. Both EET and HETE phospholipids were present in human red blood cells (RBCs) and their abundance could be substantially increased by treatment under conditions that would induce free radical oxidation of membrane phospholipids. Following incubation of human RBCs with tert-butyl hydroperoxide (tBuOOH), phospholipids were extracted and purified by normal-phase high-performance liquid chromatography (HPLC) as to glycerophospholipid class containing ethanolamine (GPE), serine (GPS) and choline (GPC) as the polar head group. Each class of phospholipid was hydrolyzed to yield the free carboxylic acid prior to on-line HPLC/ESI-MS/MS analysis. The formation of oxidized arachidonic acid esterified to phospholipids in treated RBCs was found to increase significantly for both esterified EETs in GPE, GPS and GPC which increased 49-, 34- and 59-fold, respectively, and also for esterified HETEs in GPE, GPS and GPC which increased 3-, 4- and 11-fold, respectively, compared with untreated RBCs. These results provide the first characterization of EETs formed non-enzymatically as intact phospholipids in a lipid peroxidation model system.
T Nakamura; D L Bratton; R C Murphy
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of mass spectrometry : JMS     Volume:  32     ISSN:  1076-5174     ISO Abbreviation:  J Mass Spectrom     Publication Date:  1997 Aug 
Date Detail:
Created Date:  1997-09-17     Completed Date:  1997-09-17     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  9504818     Medline TA:  J Mass Spectrom     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  888-96     Citation Subset:  IM    
National Jewish Medical and Research Center, Denver, Colorado 80206, USA.
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MeSH Terms
8,11,14-Eicosatrienoic Acid / analogs & derivatives*,  chemistry,  metabolism
Arachidonic Acid / metabolism
Chromatography, High Pressure Liquid
Erythrocyte Membrane / chemistry*
Esters / chemistry
Hydroxyeicosatetraenoic Acids / chemistry*,  metabolism
Mass Spectrometry* / methods
Membrane Lipids / chemistry*
Molecular Structure
Peroxides / metabolism
Phosphatidic Acids / chemistry*,  isolation & purification,  metabolism
Grant Support
Reg. No./Substance:
0/Esters; 0/Hydroxyeicosatetraenoic Acids; 0/Membrane Lipids; 0/Peroxides; 0/Phosphatidic Acids; 506-32-1/Arachidonic Acid; 7324-41-6/8,11,14-Eicosatrienoic Acid; 75-91-2/tert-Butylhydroperoxide

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