Document Detail

Identification of all classes of spin-trapped carbon-centered radicals in soybean lipoxygenase-dependent lipid peroxidations of omega-6 polyunsaturated fatty acids via LC/ESR, LC/MS, and tandem MS.
MedLine Citation:
PMID:  12684086     Owner:  NLM     Status:  MEDLINE    
Using the combined techniques of on-line high performance liquid chromatography/electron spin resonance (LC/ESR) and mass spectrometry (MS), we previously identified spin-trapped adducts of all expected carbon-centered lipid-derived radicals ((*)L(d)) formed in linoleic acid peroxidation. In the present study, spin trapped lipid-derived carbon-centered radicals formed from the reactions of two omega-6 polyunsaturated fatty acids (PUFAs: linoleic and arachidonic acids) with soybean lipoxygenase in the presence of alpha-[4-pyridyl 1-oxide]-N-tert-butyl nitrone (POBN) were identified using a combination of LC/ESR and LC/MS. All expected lipid-derived carbon-centered radicals in lipoxygenase-dependent peroxidations of linoleic acid and arachidonic acid were detected and identified by the combination of LC/ESR and LC/MS with confirmation by tandem mass spectrometry (MS/MS). The five classes of (*)L(d) formed from both omega-6 PUFAs including lipid alkyl radicals (L(*)), epoxyallyic radicals (OL(*)), dihydroxyallyic radicals ((*)L(OH)(2)), and a variety of R(*) and (*)RCOOH from beta-scission of lipid alkoxyl radicals, gave distinct retention times: POBN/(*)L(OH)(2) approximately 4-6 min, POBN/R(*) and POBN/(*)RCOOH approximately 8-22 min, POBN/L(*) and PBON/OL(*) approximately 25-36 min. The major beta-scission products in peroxidations of omega-6 PUFAs were the pentyl radicals. The ratio of beta-scission products, however, varied significantly depending on pH, [PUFA], as well as [O(2)].
Steven Yue Qian; Gui-Hua Yue; Kenneth B Tomer; Ronald P Mason
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Free radical biology & medicine     Volume:  34     ISSN:  0891-5849     ISO Abbreviation:  Free Radic. Biol. Med.     Publication Date:  2003 Apr 
Date Detail:
Created Date:  2003-04-09     Completed Date:  2003-12-05     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8709159     Medline TA:  Free Radic Biol Med     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1017-28     Citation Subset:  IM    
Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, National Institutes of Health, Research Triangle Park, NC 27709, USA. qian
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MeSH Terms
Arachidonic Acid / chemistry,  metabolism
Carbon / chemistry*
Chromatography, Liquid
Electron Spin Resonance Spectroscopy
Fatty Acids, Omega-6 / metabolism*
Free Radicals
Linoleic Acid / metabolism
Lipid Metabolism
Lipid Peroxidation*
Lipoxygenase / chemistry*
Mass Spectrometry
Models, Chemical
Oxygen / metabolism
Time Factors
Reg. No./Substance:
0/Fatty Acids, Omega-6; 0/Free Radicals; 2197-37-7/Linoleic Acid; 506-32-1/Arachidonic Acid; 7440-44-0/Carbon; 7782-44-7/Oxygen; EC 1.13.11.-/lipoxygenase L-1; EC

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