Simultaneous determination by GC-MS of epoxy and hydroxy FA as their methoxy derivatives

Lipids

Volumn 37, Issue 9, 2002, Pages 917-924

  Wilson, R ^a   Lyall, K ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; ESTERS; FATTY ACIDS; GAS CHROMATOGRAPHY; HYDROGENATION; MASS SPECTROMETRY; OXIDATION; SAPONIFICATION; TISSUE;

FRAGMENTATION;

LIPIDS;

BORON TRIFLUORIDE; ESTER DERIVATIVE; FATTY ACID; TETRAMETHYLAMMONIUM;

ADIPOSE TISSUE; ARTICLE; CONTROLLED STUDY; GAS CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; HYDROGENATION; LIPID ANALYSIS; LIPID OXIDATION; MALE; MASS SPECTROMETRY; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SAPONIFICATION; SOLID PHASE EXTRACTION;

EID: 0036757304     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-002-0980-5     Document Type: Article

References (35)

1. de Zwart, L.L., Meerman, J.H., Commandeur, J.N., and Vermeulen, N.P. (1999) Biomarkers of free radical damage applications in experimental animals and in humans, Free Radic. Biol. Med., 26:202-226.
2. Gutteridge, J.M. (1995) Lipid peroxidation and antioxidants as biomarkers of tissue damage, Clin. Chem. 41:1819-1828.
3. Halliwell, B. (1996) Mechanisms involved in the generation of free radicals, Pathol. Biol. 44:6-13.
4. Offord, E., van Poppel, G., and Tyrrell, R. (2000) Markers of oxidative damage and antioxidant protection: Current status and relevance to disease, Free Radic. Res. 33 (Suppl.), S5-S19.
5. Moore, K., and Roberts, L.J. (1998) Measurement of lipid peroxidation, Free Radic. Res. 28:659-671.
6. Morrow, J.D., Awad, J.A., Wu, A., Zackert, W.E., Daniel, V.C., and Roberts, L.J. (1996) Nonenzymatic free radical-catalyzed generation of thromboxane-like compounds (isothromboxanes) in vivo, J. Biol. Chem. 271, 23185-23190.
7. Johnson, J.A., Blackburn, M.L., Bull, A.W., Welsch C.W., and Watson, J.T. (1997) Separation and quantitation of linoleic acid oxidation products in mammary gland tissue from mice fed low- and high-fat diets, Lipids 32, 369-375.
8. Schneider, C., Schreier, P., and Herderich, M. (1997) Analysis of lipoxygenase-derived fatty acid hydroperoxides by electrospray ionization tandem mass spectrometry, Lipids 32, 331-336.
9. Hall, L.M., and Murphy, R.C. (1998) Activation of human polymorphonuclear leukocytes by products derived from the peroxidation of human red blood cell membranes, Chem. Res. Toxicol. 11, 1024-1031.
10. Phillips, M., Greenberg, J., and Cataneo, R.N. (2000) Effect of age on the profile of alkanes in normal human breath, Free Radic. Res. 33, 57-63.
11. Moghaddam, M.F., Motoba, K., Borhan, B., Pinot, F., and Hammock, B.D. (1996) Novel metabolic pathways for linoleic and arachidonic acid metabolism, Biochim. Biophys. Acta 1290, 327-339.
12. Moghaddam, M.F., Grant, D.F., Cheek, J.M., Greene, J.F., Williamson, K.C., and Hammock, B.D. (1997) Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase, Nature Med. 3, 562-566.
13. Oliw, E.H. (1994) Oxygenation of polyunsaturated fatty acids by cytochrome P450 monooxygenases, Prog. Lipid Res. 33, 329-354.
14. Kleinman, R., and Spencer, G.F. (1972) Gas chromatography-mass spectroscopy of methyl esters of unsaturated oxygenated fatty acids, J. Am. Oil Chem. Soc. 50, 31-38.
15. Oliw, E.H. (1985) Analysis of epoxyeicostrienoic acids by gas chromatography-mass spectrometry using chlorohydrin adducts, J. Chromatogr. 339, 175-181.
16. VanRollins, M., and Knapp H.R. (1995) Identification of arachidonate epoxides/diols by capillary chromatography-mass spectrometry, J. Lipid Res. 36, 952-966.
17. Fang, X., Kaduce, T.L., Weintraub, N.L., VanRollins, M., and Spector, A.A. (1996) Functional implications of a newly characterized pathway of 11,12-epoxyeicosatrienoic acid metabolism in arterial smooth muscle, Circ. Res. 79, 784-793.
18. Yamane, M., Abe, A., and Yamane, S. (1994) High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate, J. Chromatogr. B 652, 123-136.
19. Ulsaker, G.A., and Teien, G. (1983) Gas chromatographic-mass spectrometric identification of 9,10-epoxystearate in human blood, Analyst 108, 521-524.
20. Ulsaker, G.A., and Teien, G. (1986) Gas chromatographic-mass spectrometric identification of 9,10-epoxyoctadeca-12-enoate ester and 12,13-epoxyoctadeca-9-enoate ester in human blood, Analyst 111, 559-561.
21. Ulsaker, G.A., and Teien, G. (1995) Identification of 9,10-epoxyoctadecanoic acid in human urine using gas chromatography-mass spectrometry, Biomed. Chromatogr. 9, 183-187.
22. Dudda, A., Spiteller, G., and Kobelt, F. (1996) Lipid oxidation products in ischemic porcine heart tissue, Chem. Phys. Lipids 82, 39-51.
23. Wilson, R., Smith, R., Wilson, P., Shepherd, M.J., and Riemersma, R.A. (1997) Quantitative gas chromatography-mass spectrometry isomer-specific measurement of hydroxy fatty acids in biological samples and food as a marker of lipid peroxidation, Anal. Biochem. 248, 76-85.
24. Christie, W.W. (1982) The preparation of derivatives of lipids, in Lipid Analysis (Christie, W.W., ed.), pp. 51-61, Pergamon Press, Oxford.
25. Gardner, H.W. (1997) Analysis of plant lipoxygenase metabolites, in Advances in Lipid Methodology Four (Christie, W.W., ed.), pp. 1-44, The Oily Press, Dundee, Scotland.
26. Christie, W.W. (1997) Structural analysis of fatty acids, in Advances in Lipid Methodology Four (Christie, W.W., ed.), pp. 119-169, The Oily Press, Dundee, Scotland.
27. Logan, R.L., Riemersma, R.A., Thomson M., Oliver, M.F., Olsson, A.G., Walldius, G., Rossner, S., Kaijser, L., Callmer, E., Carlson, L.A., et al. (1978) Risk factors for ischaemic heart-disease in normal men aged 40. Edinburgh-stockholm study. Lancet 1, 949-954.
28. Wilson, R., Lyall, K., Smyth, L., Fernie, C.E., and Riemersma R.A. (2002) Dietary hydroxy fatty acids are absorbed in humans - Implications for the measurement of 'oxidative stress' in vivo, Free Radic. Biol. Med. 32, 162-168.
29. Kubow, S. (1992) Routes of formation and toxic consequences of lipid oxidation products in foods, Free Radic. Biol. Med. 12, 63-81.
30. Wilson, R., Fernie, C.E., Scrimgeour, C.M., Lyall, K., Smyth, L., and Riemersma, R.A. (2002) Dietary epoxy fatty acids are absorbed in healthy women, Eur. J. Clin. Invest. 32, 79-83.
31. Nourooz-Zadeh, J., Tajaddini-Sarmadi, J., Ling, K.E., and Wolff, S.P. (1996) Low-density lipoprotein is the major carrier of lipid hydroperoxides in plasma. Relevance to determination of total plasma lipid hydroperoxide concentrations, Biochem. J. 313, 781-786.
32. Zamburlini, A., Maiorino, M., Barbera, P., Roveri, A., and Ursini, F. (1995) Direct measurement by single photon counting of lipid hydroperoxides in human plasma and lipoproteins, Anal. Biochem. 232, 107-113.
33. Castle, L., Mayo, A., and Gilbert, J. (1990) Migration of epoxidized soya bean oil into foods from retail packaging materials and from plasticised PVC film used in the home, Food Addit. Contam. 7, 29-36.
34. Blee, E., and Schuber, F. (1990) Efficient epoxidation of unsaturated fatty acids by a hydroperoxide-dependent oxygenase, J. Biol. Chem. 265, 12887-12894.
35. Carpenter, K.L., Taylor, S.E., Ballantine, J.A., Fussell, B., Halliwell, B., and Mitchinson, M.J. (1993) Lipids and oxidized lipids in human atheroma and normal aorta. Biochim. Biophys. Acta 1167, 121-130.