Coordination (ag+) ion spray - Mass spectrometry of peroxidation products of cholesterol linoleate and cholesterol arachidonate: High-performance liquid chromatography - Mass spectrometry analysis of peroxide products from polyunsaturated lipid autoxidation

Journal of the American Chemical Society

Volumn 122, Issue 33, 2000, Pages 8042-8055

  Havrilla, Christine M ^a,c   Hachey, David L ^b   Porter, Ned A ^a,b,c  

^a VANDERBILT UNIVERSITY   (United States)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONIC ACID DERIVATIVE; CHOLESTEROL DERIVATIVE; HYDROPEROXIDE; LINOLEIC ACID; PEROXIDE; SILVER;

ARTICLE; AUTOOXIDATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION MONITORING; LIPID PEROXIDATION; MASS SPECTROMETRY; STEREOISOMERISM;

EID: 0034705975     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001180f     Document Type: Article

References (47)

1. (a) Nicholson, A. C.; Hajjar, D. P. Am. Scientist 1995, 83, 460-467.
2. (b) Feher, J.; Lengyel, G; Blazovics, A. Scand. J. Gastroenterol. 1998, 288S, 38-46.
3. (c) Welsch, C. W. Free Rad. Biol. Med. 1995, 18, 757-773.
4. (d) Knight, J. A. Ann. Clin. Lab. Sci. 1997, 27, 11-25.
5. Steinberg, D.; Parhsarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. N. Engl. J. Med. 1989, 320, 915-924.
6. (a) Steinbrecher, H. P.; Lougheed, M.; Kwan, W. C.; Dirks, M. J. Biol. Chem. 1989, 264, 15216-15223.
7. (b) Morel, D. W.; DiCorleto, P. E.; Chilsom, G. M. Arteriosclerosis 1984, 4, 357-364.
8. (c) Steinbrecher, U. P.; Parthasarathy, S.; Leake, D. S.; Witztum, J. L.; Steinberg, D. Proc. Natl. Acad. Sci., U.S.A. 1984, 81, 3883-3887.
9. (d) Ingold, K. U.; Bowry, V. W.; Stocker, R.; Walling, C. Proc. Natl. Acad. Sci., U.S.A. 1993, 90, 45-49.
10. (e) Esterbauer, H.; Gebicki, J.; Puhl, H.; Jürgens, G. Free Radical Biol. Med. 1992, 13, 341-390.
11. (f) Sato, K.; Niki, E.; Shimasaki, H. Arch. Biochem. Biophys. 1990, 279, 402-405.
12. (g) Bowry, V. W.; Stocker, R. J. Am. Chem. Soc. 1993, 115, 6029-6044.
13. (h) Bowry, V. W.; Stanley, K. K.; Stocker, R. Proc. Natl. Acad. Sci., U.S.A. 1992, 89, 10316-10320.
14. (i) Fu, S.; Davies, M. J.; Stocker, R.; Dean, R. T. Biochem. J. 1998, 333, 519-525.
15. (j) Berliner, J. A.; Heinecke, J. W. Free Radical Biol. Med. 1996, 20, 707-727.
16. (k) McIntyre, T. M.; Zimmerman, G. A.; Prescott, S. M. J Biol Chem. 1999, 274, 25189-25192.
17. For a complete discussion of cholesterol autoxidation, see Smith, L. L. Cholesterol Autoxidation; Plenum Press: New York, 1981.
18. Kenar, J. A.; Havrilla, C. M.; Porter, N. A.; Guyton, J. R.; Brown, S. A.; Klemp, K. R.; Selinger, E. Chem. Res. Tox. 1996, 9, 737-744.
19. (a) Porter, N. A.; Logan, J.; Kontoyiannidou, V. J. Org. Chem. 1979, 44, 3177-3181.
20. (b) Porter, N. A.; Wolf, R. A.; Yarboro, E. M.; Weenen, H. Biochem. Biophys. Res. Comm. 1979, 89, 1058-1064.
21. (a) MacMillian, D. K.; Murphy, R. C. J. Am. Soc. Mass Spectrom. 1995, 6, 1190-1201.
22. (b) See also, Nakamura, T.; Hall, L.; Murphy R. C. In Eicosanoids and Other Bioactive Lipids in Cancer, Inflammation, and Radiation Injury, 4; Honn, K. V., Ed.; Advances in Experimental Medicine and Biology; Kluwer Academic/Plenum: New York, 1999; Vol. 469, pp 539-545.
23. (b) See also, Nakamura, T.; Hall, L.; Murphy R. C. In Eicosanoids and Other Bioactive Lipids in Cancer, Inflammation, and Radiation Injury, 4; Honn, K. V., Ed.; Advances in Experimental Medicine and Biology; Kluwer Academic/Plenum: New York, 1999; Vol. 469, pp 539-545.
24. (a) Bayer, E.; Gfrorer, P.; Rentel, C. Angew. Chem.-Int. Ed. 1999, 38, 992-995.
25. (b) See also, Suma, K.; Raju, N. P., and Vairamani, M., Rapid Comm. Mass Spectrom. 1997, 11, 1939-1944.
26. (a) Hock, H. Angew. Chem. 1936, 49, 595.
27. (b) For a review see, Frimer, A. A. Chem. Rev. 1979, 79, 359-387.
28. (c) Tanigawa, S.; Kajiware, T.; Hatanaka, A. Photochemistry 1984, 23, 2439-2444.
29. (d) Gardner, H. W.; Planter, R. D. Lipids 1984, 19, 294-298.
30. Autoxidation was initiated by 10% di-tert-butyl hyponitrite (DTBN), see (a) Mendenhall, G. D. Tetrahedron Lett 1983, 24, 451-454. (b) Traylor, T. G.; Kiefer, H. Tetrahedron Lett. 1966, 49, 6163-6168.
31. Autoxidation was initiated by 10% di-tert-butyl hyponitrite (DTBN), see (a) Mendenhall, G. D. Tetrahedron Lett 1983, 24, 451-454. (b) Traylor, T. G.; Kiefer, H. Tetrahedron Lett. 1966, 49, 6163-6168.
32. (a) Porter, N. A., Caldwell, S. E., Mills, K. A. Lipids 1995, 30, 277-290.
33. (b) Porter, N. A. Acc. Chem. Res. 1986, 19, 262-268.
34. (c) O'Connor, D. E.; Mihelech, E. D.; and Coleman, M. C. J. Am. Chem. Soc. 1983, 106, 3577-3584.
35. (d) Porter, N. A.; Funk, M. O.; Gilmore, D.; Isaac, R.; Nixon, J. J. Am. Chem. Soc. 1976, 98, 6000-6005.
36. (e) Funk, M. O.; Isaac, R.; Porter, N. A. J. Am. Chem. Soc. 1975, 97, 1281-1282.
37. (f) Porter, N. A.; Funk, M. O. J. Org. Chem. 1975, 40, 3614-3615.
38. (g) Pryor, W. A.; Stanley, J. P. J. Org. Chem. 1975, 40, 3615-3617.
39. Khan, J. A.; Porter, N. A., Angew. Chem. 1982, 94, 220-221.
40. Dussault, P.; Sahli, A. J. Org. Chem. 1992, 57, 1009-1012.
41. (a) Adam, W.; Duran, N. J. Am. Chem. Soc. 1977, 99, 2729-2734.
42. (b) Adam, W.; Duran, N. J. Org. Chem. 1973, 38, 1434-1436.
43. (c) Bloodworth, A. J.; Baker, D. S. Chem. Commun. 1981, 11, 547-549.
44. (d) Bloodworth, A. J.; Eggelte, H. J. Tetrahedron Lett. 1984, 25, 1525-1528.
45. (e) Balci, M.; Suetbeyaz, Y. Tetrahedron Lett. 1983, 24, 311-314.
46. (f) Yoshida, M.; Miura, M.; Nojima, M.; Kusabayashi. S. J. Am.Chem. Soc. 1983, 105, 6279-6285.
47. Morrow, J. D.; Minton, T. A.; Mukundan, C. R.; Campbell, M. D.; Zacker, W. E.; Daniel, V. C.; Badr, K. R.; Blair, I. A.; Roberts, J. L., Jr. J. Biol. Chem. 1994, 269, 4317-4326 and references cited.