Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals

Journal of Biological Chemistry

Volumn 276, Issue 24, 2001, Pages 20831-20838

  Schneider, Claus ^a   Tallman, Keri A ^a   Porter, Ned A ^a   Brash, Alan R ^a,b  

^a VANDERBILT UNIVERSITY   (United States)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CARBOXYLATION; LIPIDS; PEROXIDES; TOXIC MATERIALS;

NONENZYMATIC TRANSFORMATIONS;

ENZYMES;

12 OXO 9 DODECENOIC ACID; 13 HYDROPEROXY 9,11 OCTADECADIENOIC ACID; 4 HYDROXYNONENAL; 9 HYDROPEROXY 10.12 OCTADECADIENOIC ACID; FATTY ACID DERIVATIVE; HYDROPEROXIDE DERIVATIVE; LINOLEIC ACID; UNCLASSIFIED DRUG; 13-HYDROPEROXY-9,11-OCTADECADIENOIC ACID; 4-HYDROXY-2-NONENAL; 9 HYDROPEROXY 11,12 OCTADECADIENOIC ACID; 9-HYDROPEROXY-11,12-OCTADECADIENOIC ACID; ALDEHYDE; ALPHA TOCOPHEROL; CYTOCHROME P450; HYDROPEROXIDE LYASE; LIPID PEROXIDE; LIPOXYGENASE; LYASE; RECOMBINANT PROTEIN;

ARTICLE; CHIRALITY; LIPID PEROXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; CHEMISTRY; CUCUMBER; ENZYMOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; METABOLISM; SOYBEAN; STEREOISOMERISM; ULTRAVIOLET SPECTROPHOTOMETRY;

PERO;

ALDEHYDE-LYASES; ALDEHYDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CUCURBITACEAE; CYTOCHROME P-450 ENZYME SYSTEM; KINETICS; LINOLEIC ACIDS; LIPID PEROXIDES; LIPOXYGENASE; RECOMBINANT PROTEINS; SOYBEANS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; VITAMIN E;

EID: 0035877699     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M101821200     Document Type: Article

References (30)

1. Benedetti, A., Comporti, M., and Esterbauer, H. (1980) Biochim. Biophys. Acta 620, 281-296
2. Benedetti, A., Esterbauer, H., Ferrali, M., Fulceri, R., and Comporti, M. (1982) Biochim. Biophys. Acta 711, 345-356
3. Esterbauer, H., Benedetti, A., Lang, J., Fulceri, R., Fauler, G., and Comporti, M. (1986) Biochim. Biophys. Acta 876, 154-166
4. Esterbauer, H., Schaur, R. J., and Zollner, H. (1991) Free Radic. Biol. Med. 11, 81-128
5. Comporti, M. (1998) Free Radic. Res. 28, 623-635
6. Fazio, V. M., Rinaldi, M., Ciafre, S., Barrera, G., and Farace, M. G. (1993) Mol. Aspects Med. 14, 217-228
7. Markesbery, W. R., and Carney, J. M. (1999) Brain Pathol. 9, 133-146
8. Keller, J. N., and Mattson, M. P. (1998) Rev. Neurosci. 9, 105-116
9. Nair, J., Barbin, A., Velic, I., and Bartsch, H. (1999) Mutat. Res. 424, 59-69
10. Porter, N. A., and Pryor, W. A. (1990) Free Radic. Biol. Med. 8, 541-543
11. Gardner, H. W., and Hamberg, M. (1993) J. Biol. Chem. 268, 6971-6977
12. Gardner, H. W., and Grove, M. J. (1998) Plant Physiol. 116, 1359-1366
13. Noordermeer, M. A., Feussner, I., Kolbe, A., Veldink, G. A., and Vliegenthart, J. F. G. (2000) Biochem. Biophys. Res. Commun. 277, 112-116
14. Lee, S. H., and Blair, I. A. (2000) Chem. Res. Toxicol. 13, 698-702
15. Matthew, J. A., Chan, H. W.-S., and Galliard, T. (1977) Lipids 12, 324-326
16. Tijet, N., Schneider, C., Muller, B. L., and Brash, A. R. (2001) Arch. Biochem. Biophys. 386, 281-289
17. Havrilla, C. M., Hachey, D. L., and Porter, N. A. (2000) J. Am. Chem. Soc. 122, 8042-8055
18. Ingram, C. D., and Brash, A. R. (1988) Lipids 23, 340-344
19. Silverstein, R. M., Bassler, G. C., and Morrill, T. C. (1981) Spectrometric Identification of Organic Compounds, 4th Ed., pp. 181-247, John Wiley & Sons, Inc., New York
20. Schneider, C., Schreier, P., and Humpf, H.-U. (1997) Chirality 9, 563-567
21. Brash, A. R. (2000) Lipids 35, 947-952
22. Corey, E. J., and Nagata, R. (1987) Tetrahedron Lett. 45, 5391-5394
23. Frimer, A. A. (1979) Chem. Rev. 79, 359-387
24. Gardner, H. W., and Plattner, R. D. (1984) Lipids 19, 294-299
25. Gardner, H. W. (1998) Lipids 33, 745-749
26. Hatanaka, A. (1993) Phytochemistry 34, 1201-1218
27. Hamberg, M. (1983) Biochim. Biophys. Acta 752, 191-197
28. Porter, N. A., Weber, B. A., Weenen, H., and Khan, J. A. (1980) J. Am. Chem. Soc. 102, 5597-5601
29. Porter, N. A., Caldwell, S. E., and Mills, K. A. (1995) Lipids 30, 277-290
30. Bowry, V. W., and Ingold, K. U. (1999) Acc. Chem. Res. 32, 27-34