Identification of spin trapped carbon-centered radicals in soybean lipoxygenase-dependent peroxidations of ω-3 polyunsaturated fatty acids by LC/ESR, LC/MS, and tandem MS

Free Radical Biology and Medicine

Volumn 35, Issue 1, 2003, Pages 33-44

  Qian, Steven Yue ^a   Guo, Qiong ^a   Mason, Ronald P ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

Free radicals; Lipid derived radicals; Lipoxygenase dependent peroxidation; On line LC ESR; On line LC MS; Tandem mass spectrometry

Indexed keywords

CARBON; DOCOSAHEXAENOIC ACID; FREE RADICAL; LINOLENIC ACID; LIPOXYGENASE; N TERT BUTYL ALPHA (4 PYRIDYL 1 OXIDE) NITRONE; NITRONE DERIVATIVE; OMEGA 3 FATTY ACID;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON SPIN RESONANCE; ENZYME MECHANISM; ISOMERISM; LIQUID CHROMATOGRAPHY; ONLINE ANALYSIS; PEROXIDATION; PRIORITY JOURNAL; SOYBEAN; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

GLYCINE MAX;

EID: 0037524249     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(03)00217-X     Document Type: Article

References (31)

1. Halliwell B. Antioxidants in human health and disease. Annu. Rev. Nutr. 16:1996;33-50.
2. Gutteridge J.M.C. Free radicals in disease processes a compilation of cause and consequence . Free Radic. Res. Commun. 19:1993;141-158.
3. Ashok B.T., Ali R. The aging paradox free radical theory of aging . Exp. Gerontol. 34:1999;293-303.
4. Chandra M., Chandra N., Agrawal R., Kumar A., Ghatak A., Pandey V.C. The free radical system in ischemic heart disease. Int. J. Cardiol. 43:1994;121-125.
5. Dreher D., Junod A.F. Role of oxygen free radicals in cancer development. Eur. J. Cancer. 32A:1996;30-38.
6. Knight J.A. Free radicals their history and current status in aging and disease . Ann. Clin. Lab. Sci. 28:1998;331-346.
7. Girotti A.W. Mechanisms of lipid peroxidation. Free Radic. Biol. Med. 1:1985;87-95.
8. Gardner H.W. Oxygen radical chemistry of polyunsaturated fatty acids. Free Radic. Biol. Med. 7:1989;65-86.
9. Janzen E.G., Blackburn B.J. Detection and identification of short-lived free radicals by an electron spin resonance trapping technique. J. Am. Chem. Soc. 90:1968;5909-5910.
10. Janzen E.G., Blackburn B.J. Detection and identification of short-lived free radicals by electron spin resonance trapping techniques (spin trapping). Photolysis of organolead, -tin, and -mercury compounds. J. Am. Chem. Soc. 91:1969;4481-4490.
11. Janzen E.G. Spin trapping. Acc. Chem. Res. 4:1971;31-40.
12. Buettner G.R. Spin trapping EPR parameters of spin adducts . Free Radic. Biol. Med. 3:1987;259-303.
13. Buettner G.R., Kelley E.E., Burns C.P. Membrane lipid free radicals produced from L1210 murine leukemia cells by photofrin photosensitization an EPR spin trapping study . Free Radic. Biol. Med. 15:1993;528.
14. Buettner G.R., Kelley E.E., Burns C.P. Membrane lipid free radicals produced from L1210 murine leukemia cells by photofrin photosensitization an electron paramagnetic resonance spin trapping study . Cancer Res. 53:1993;3670-3673.
15. North J.A., Spector A.A., Buettner G.R. Cell fatty acid composition affects free radical formation during lipid peroxidation. Am. J. Physiol. 267:1994;C177-C188.
16. Wagner B.A., Buettner G.R., Burns C.P. Free radical mediated lipid peroxidation in cells oxidizability is a function of cell lipid bis-allylic hydrogen content . Biochemistry. 33:1994;4449-4453.
17. Qian S.Y., Buettner G.R. Iron and dioxygen chemistry is an important route to initiation of biological free radical oxidations an electron paramagnetic resonance spin trapping study . Free Radic. Biol. Med. 26:1999;1447-1456.
18. Kadiiska M.B., Hanna P.M., Jordan S.J., Mason R.P. Electron spin resonance evidence for free radical generation in copper-treated vitamin E- and selenium-deficient rats in vivo spin-trapping investigation . Mol. Pharmacol. 44:1993;222-227.
19. Kadiiska M.B., Mason R.P., Dreher K.L., Costa D.L., Ghio A.J. In vivo evidence of free radical formation in the rat lung after exposure to an emission source air pollution particle. Chem. Res. Toxicol. 10:1997;1104-1108.
20. 2-isoprostanes in vivo by acute Cr(VI) poisoning. Chem. Res. Toxicol. 11:1998;1516-1520.
21. Ghio A.J., Kadiiska M.B., Xiang Q.-H., Mason R.P. In vivo evidence of free radical formation after asbestos instillation an ESR spin trapping investigation . Free Radic. Biol. Med. 24:1998;11-17.
22. Iwahashi H., Deterding L.J., Parker C.E., Mason R.P., Tomer K.B. Identification of radical adducts formed in the reactions of unsaturated fatty acids with soybean lipoxygenase using continuous flow fast atom bombardment with tandem mass spectrometry. Free Radic. Res. 25:1996;255-274.
23. Qian S.Y., Tomer K.B., Yue G.H., Guo Q., Kadiiska M.B., Mason R.P. Characterization of the initial carbon-centered pentadienyl radical and subsequent radicals in lipid peroxidation identification via LC-ESR and MS . Free Radic. Biol. Med. 33:2002;998-1009.
24. Qian S.Y., Chen Y.-R., Deterding L.J., Fann Y.C., Chignell C.F., Tomer K.B., Mason R.P. Identification of protein-derived tyrosyl radical in the reaction of cytochrome c and hydrogen peroxide characterization by ESR spin-trapping, HPLC and MS . Biochem. J. 363:2002;281-288.
25. Qian S.Y., Yue G.-H., Tomer K.B., Mason R.P. Identification of all classes of spin-trapped carbon-centered radicals in soybean lipoxygenase-dependent lipid peroxidations of ω-6 polyunsaturated fatty acids via LC/ESR, LC/MS, and tandem MS. Free Radic. Biol. Med. 34:2003;1017-1028.
26. Albro P.W., Knecht K.T., Schroeder J.L., Corbett J.T., Marbury D., Collins B.J., Charles J. Isolation and characterization of the initial radical adduct formed from linoleic acid and alpha-(4-pyridyl 1-oxide)-N-tert-butylnitrone in the presence of soybean lipoxygenase. Chem. Biol. Interact. 82:1992;73-89.
27. Ortiz de Montellano P.R., Augusto O., Viola F., Kunze K.L. Carbon radicals in the metabolism of alkyl hydrazines. J. Biol. Chem. 258:1983;8623-8629.
28. Moseley M.A., Deterding L.J., Tomer K.B., Jorgenson J.W. Nanoscale packed capillary liquid chromatography coupled with mass spectrometry using a coaxial continuous flow fast atom bombardment interface. Anal. Chem. 63:1991;1467-1473.
29. Porter N.A. Mechanisms for the autoxidation of polyunsaturated lipids. Acc. Chem. Res. 19:1986;262-268.
30. Nunez A., Foglia T.A., Piazza G.J. Characterization of lipoxygenase oxidation products by high-performance liquid chromatography with electron impact-mass spectrometric detection. Lipids. 36:2001;851-856.
31. Wilcox A.L., Marnett L.J. Polyunsaturated fatty acid alkoxyl radicals exist as carbon-centered epoxyallylic radicals a key step in hydroperoxide amplified lipid peroxidation . Chem. Res. Toxicol. 6:1993;413-416.