Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA): I. Direct evidence for cis-EODA formation from oleic acid oxidation by liver microsomes and isolated hepatocytes

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 784, Issue 2, 2003, Pages 351-365

  Tsikas, Dimitrios ^a   Sawa, Masayuki ^a,c   Brunner, Gorig ^a   Gutzki, Frank Mathias ^a   Meyer, Hartmut H ^b   Frölich, Jürgen C ^a  

^a HANNOVER MEDICAL SCHOOL   (Germany)

^b LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^c ASAHIKAWA MEDICAL COLLEGE   (Japan)

Author keywords

Cis 9,10 Epoxyoctadecanoic acid; Oleic acid

Indexed keywords

BODY FLUIDS; ENZYMES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OLEIC ACID; PEROXIDES;

EPOXIDATION; LIVER MICROSOMES;

ANIMAL CELL CULTURE;

9,10 EPOXYOCTADECANOIC ACID; CYTOCHROME P450; ETHER DERIVATIVE; FATTY ACID; OLEIC ACID; STEARIC ACID DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BLOOD; CATALYSIS; CATALYST; CELL ISOLATION; CONCENTRATION RESPONSE; EPOXIDATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDRATION; INCUBATION TIME; LIVER CELL; LIVER MICROSOME; MAMMAL; MASS SPECTROMETRY; OXIDATION; PHYSIOLOGY; PRIORITY JOURNAL; URINE;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; EPOXY COMPOUNDS; FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEPATOCYTES; KINETICS; MICROSOMES, LIVER; OLEIC ACID; OXIDATION-REDUCTION; RATS;

MAMMALIA; ORYCTOLAGUS CUNICULUS;

EID: 0347297485     PISSN: 15700232     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1570-0232(02)00821-8     Document Type: Article

References (47)

1. Kupfer D. Pharmacol. Ther. 11:1980;469.
2. Örning L. Biochem. Biophys. Res. Commun. 143:1987;337.
3. VanRollins M., Baker R.C., Sprecher H.W., Murphy R.C. J. Biol. Chem. 259:1984;5776.
4. Oesch F. Xenobiotica. 3:1972;305.
5. Fjestedt T.A., Allen R.H., Duncan B.K., Jakoby W.B. J. Biol. Chem. 248:1973;3702.
6. Keppler D., Hagmann W., Rapp S., Denzlinger C., Koch H.K. Hepatology. 5:1985;883.
7. Samuelsson B., Dahlen S-E., Lindgren J.A., Rouzer C.A., Serhan C.N. Science. 237:1987;1171.
8. Dickey B.F., Thrall R.S., McCormick J.R., Ward P.A. Am. J. Pathol. 103:1981;376.
9. Ehrhart I.C., Hofmann W.F. J. Appl. Physiol. Respir. Environ. Exerc. Physiol. 50:1981;1115.
10. Spragg R.G., Abraham J.L., Loomis W.H. Am. Rev. Respir. Dis. 126:1982;553.
11. Ulsaker G.A., Teien G. Analyst. 108:1983;521.
12. Ulsaker G.A., Teien G. Analyst. 115:1990;259.
13. Ulsaker G.A., Teien G. Biomed. Chromatogr. 9:1995;183.
14. Toto R., Siddhanta A., Manna S., Pramanik B., Falck J.R., Capdevilla J. Biochim. Biophys. Acta. 919:1987;132.
15. Swern D., Findley T.W., Scanlan J.T. J. Am. Chem. Soc. 66:1944;1925.
16. D. Tsikas, Ph.D. Thesis, University of Hannover, Hannover, Germany, 1987.
17. Omura T., Sato R. J. Biol. Chem. 239:1964;2370.
18. Seglen P.O. Exp. Cell Res. 74:1974;450.
19. Mito M., Ebata H., Kusano M., Onishi T., Saito T., Sakamoto S. Transplantation. 28:1979;499.
20. Borch R.F. Anal. Chem. 47:1975;2437.
21. Blair I.A., Barrow S.E., Waddel K.A., Lewis P.J., Dollery C.T. Prostaglandins. 23:1983;579.
22. Durst H.D., Milano M., Kikta E.J. Jr., Connelly S.A., Grushka E. Anal. Chem. 47:1975;1797.
23. Engelhardt H., Elgass H. J. Chromatogr. 158:1978;249.
24. Lam S., Grushka E. Sep. Purif. Methods. 14:1985;67.
25. Oliw E.H., Guengerich F.P., Oates J.A. J. Biol. Chem. 257:1982;3771.
26. Chacos N., Folck J.R., Wixtrom C., Capdevila J. Biochem. Biophys. Res. Commun. 104:1982;916.
27. Watabe T., Ueno Y., Imazumi J. Biochem. Pharmacol. 20:1971;912.
28. Oesch F., Kaubisch N., Jerina D.M., Dally J.W. Biochemistry. 10:1971;4858.
29. Lu A.Y.H., Miwa G.T. Annu. Rev. Pharmacol. Toxicol. 20:1980;513.
30. Nunez D., Randon J., Gandhi C., Siafaka-Kapadai A., Olson M.S., Hanahan D.J. J. Biol. Chem. 265:1990;18330.
31. Sharma R., Gupta S., Singhal S.S., Ansari G.A.S., Awasthi Y.C. J. Biochem. Toxicol. 6:1991;147.
32. Egan B.M., Lu G., Green E.L. Prostaglandins Leukot. Essent. Fatty Acids. 60:1999;411.
33. Tsikas D., Brunner G. Fresenius J. Anal. Chem. 343:1992;330.
34. Vallvé J.-C., Uliaque K., Girona J., Cabré A., Ribalta J., Heras M., Masana L. Atherosclerosis. 164:2002;45.
35. Yount E.A., Harris R.A. Arch. Biochem. Biophys. 217:1982;503.
36. Nomura T., Tachibana M., Nomura H., Chihara M., Hagino Y. Lipids. 22:1987;474.
37. Sevanian A., Mead J.F., Stein R.A. Lipids. 14:1979;634.
38. Sevanian A., Stein R.A., Mead J.F. Lipids. 16:1981;781.
39. Blée E., Schuber F. J. Biol. Chem. 265:1990;12887.
40. Knoche H.W. Lipids. 6:1971;581.
41. Hamberg M., Hamberg G. Arch. Biochem. Biophys. 283:1990;409.
42. Chu I., Villeneuve D.C., Secours V., Viau A. Bull. Environ. Contam. Toxicol. 22:1979;462.
43. Fahlstadius P. Lipids. 23:1988;1015.
44. Pinot F., Salaun J.P., Bosch H., Lesot A., Mioskowski C., Durst F. Biochem. Biophys. Res. Commun. 184:1992;183.
45. Sharma R., Gupta S., Ahmad H., Ansari G.A., Awasthi Y.C. Toxicol. Appl. Pharmacol. 104:1990;421.
46. Waddington E., Sienuarine K., Puddey I., Croft K. Anal. Biochem. 292:2001;234.
47. Waddington E.I., Puddey I.B., Mori T.A., Croft K.D. Redox Rep. 7:2002;179.