| 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. | |
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MedLine Citation:
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PMID: 12684086 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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)]. |
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Authors:
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Steven Yue Qian; Gui-Hua Yue; Kenneth B Tomer; Ronald P Mason |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Free radical biology & medicine Volume: 34 ISSN: 0891-5849 ISO Abbreviation: Free Radic. Biol. Med. Publication Date: 2003 Apr |
Date Detail:
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Created Date: 2003-04-09 Completed Date: 2003-12-05 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8709159 Medline TA: Free Radic Biol Med Country: United States |
Other Details:
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Languages: eng Pagination: 1017-28 Citation Subset: IM |
Affiliation:
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Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, National Institutes of Health, Research Triangle Park, NC 27709, USA. qian 1@niehs.nih.gov |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Arachidonic Acid
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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 |
| Chemical | |
Reg. No./Substance:
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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 1.13.11.12/Lipoxygenase |
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