An update on products and mechanisms of lipid peroxidation

Molecular Nutrition and Food Research

Volumn 53, Issue 3, 2009, Pages 315-321

  Schneider, Claus ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antioxidant; Bis allylic; Hydroperoxide; Linoleic acid; Peroxyl radical

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; LIPID PEROXIDE; OCTADECADIENOIC ACID; PERHYDROXYL RADICAL; PEROXIDE; UNSATURATED FATTY ACID;

CHEMISTRY; KINETICS; LIPID PEROXIDATION; REVIEW; THERMODYNAMICS;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; FATTY ACIDS, UNSATURATED; KINETICS; LIPID PEROXIDATION; LIPID PEROXIDES; PEROXIDES; THERMODYNAMICS;

EID: 62749143041     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.200800131     Document Type: Review

References (39)

1. Bergström, S., Autoxidation of linoleic acid. Nature 1945, 156, 717-718.
2. Bolland, J. L., Kinetics of olefin oxidation. Q. Rev., Chem. Soc. 1949, 3, 1-21.
3. Bergström, S., Blomstrand, R., Laurell, S., On the autoxidation of linoleic acid in aqueous colloidal solution. Acta Chem. Scand. 1950, 4, 245-250.
4. Bateman, L., Olefin oxidation. Q. Rev., Chem. Soc. 1954, 8, 147-167.
5. Ingold, K. U., Inhibition of the autoxidation of organic substances in the liquid phase. Chem. Rev. 1961, 61, 563-589.
6. Gardner, H. W., Oxygen radical chemistry of polyunsaturated fatty acids. Free Radical Biol. Med. 1989, 7, 65-86.
7. Gerwick, W. H., Epoxy allylic carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipins. Lipids 1996, 31, 1215-1231.
8. Grechkin, A., Recent developments in biochemistry of the plant lipoxygenase pathway. Prog. Lipid Res. 1998, 37, 317-352.
9. Tijet, N., Brash, A. R., Allene oxide synthases and allene oxides. Prostaglandins Other Lipid Mediat. 2002, 68-69, 423-431.
10. Schneider, C., Niisuke, K., Boeglin, W. E., Voehler, M., et al., Enzymatic synthesis of a bicyclobutane fatty acid by a hemoprotein lipoxygenase fusion protein from the cyanobacterium Anabaena PCC 7120. Proc. Natl. Acad. Sci. USA 2007, 104, 18941-18945.
11. Haslbeck, F., Grosch, W., Firl, J., Formation of hydroperoxides with unconjugated diene systems during autoxidation and enzymic oxygenation of linoleic acid. Biochim. Biophys. Acta 1983, 750, 185-193.
12. Porter, N. A., Caldwell, S. E., Mills, K. A., Mechanisms of free radical oxidation of unsaturated lipids. Lipids 1995, 30, 277-290.
13. Maillard, B., Ingold, K. U., Scaiano, J. C., Rate constants for the reactions of free radicals with oxygen in solution. J. Am. Chem. Soc. 1983, 105, 5095-5099.
14. Porter, N. A., Mechanism for the autoxidation of polyunsaturated lipids. Acc. Chem. Res. 1986, 19, 262-268.
15. Marnett, L. J., Peroxyl free radicals: potential mediators of tumor initiation and promotion. Carcinogenesis 1987, 8, 1365-1373.
16. Burton, G. W., Ingold, K. U., Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vivo. J. Am. Chem. Soc. 1981, 103, 6472-6477.
17. Schneider, C., Chemistry and biology of vitamin E. Mol. Nutr. Food Res. 2005, 49, 7-30.
18. Ingold, K. U., Bowry, V. W., Stocker, R., Walling, C., Autoxidation of lipids and antioxidation by alpha-tocopherol and ubiquinol in homogeneous solution and in aqueous dispersions of lipids: unrecognized consequences of lipid particle size as exemplified by oxidation of human low density lipoprotein. Proc. Natl. Acad. Sci. USA 1993, 90, 45-49.
19. Bowry, V. W., Ingold, K. U., The unexpected role of vitamin E (alpha-tocopherol) in the peroxidation of human low-density lipoprotein. Acc. Chem. Res. 1999, 32, 27-34.
20. Upston, J. M., Terentis, A. C., Stocker, R., Tocopherol-mediated peroxidation of lipoproteins: implications for vitamin E as a potential antiatherogenic supplement. FASEB J. 1999, 13, 977-994.
21. O'Connor, D. E., Mihelich, E. D., Coleman, M. C., Stereochemical course of the autoxidative cyclization of lipid hydroperoxides to prostaglandin-like bicyclo endoperoxides. J. Am. Chem. Soc. 1984, 106, 3577-3584.
22. Musiek, E. S., Yin, H., Milne, G. L., Morrow, J. D., Recent advances in the biochemistry and clinical relevance of the isoprostane pathway. Lipids 2005, 40, 987-994.
23. Schneider, C., Pratt, D. A., Porter, N. A., Brash, A. R., Control of oxygenation in lipoxygenase and cyclooxygenase catalysis. Chem. Biol. 2007, 14, 473-488.
24. Pratt, D. A., Mills, J. H., Porter, N. A., Theoretical calculations of carbon-oxygen bond dissociation enthalpies of peroxyl radicals formed in the autoxidation of lipids. J. Am. Chem. Soc. 2003, 125, 5801-5810.
25. Brash, A. R., Autoxidation of methyl linoleate: identification of the bis-allylic 11-hydroperoxide. Lipids 2000, 35, 947-952.
26. Peers, K. F., Coxon, D. T., Controlled synthesis of monohydroperoxides by α-tocopherol inhibited autoxidation of polyunsaturated lipids. Chem. Phys. Lipids 1983, 32, 49-56.
27. Tallman, K. A., Pratt, D. A., Porter, N. A., Kinetic products of linoleate peroxidation: rapid β-fragmentation of nonconjugated peroxyls. J. Am. Chem. Soc. 2001, 123, 11827-11828.
28. Yeola, S. N., Saleh, S. A., Brash, A. R., Prakash, C., et al., Synthesis of 10(S)-hydroxyeicoatetraenoic acid: a novel cytochrome P-450 metabolite of arachidonic acid. J. Org. Chem. 1996, 61, 838-841.
29. Schneider, C., Boeglin, W. E., Yin, H., Stec, D. F., et al., Synthesis of dihydroperoxides of linoleic and linolenic acids and studies on their transformation to 4-hydroperoxynonenal. Lipids 2005, 40, 1155-1162.
30. Zhang, W., Sun, M., Salomon, R. G., Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo. J. Org. Chem. 2006, 71, 5607-5615.
31. Chan, H. W.-S., Levett, G., Matthew, J. A., The mechanism of the rearrangement of linoleate hydroperoxides. Chem. Phys. Lipids 1979, 24, 245-256.
32. Porter, N. A., Wujek, D. G., Autoxidation of polyunsaturated fatty acids, an expanded mechanistic study. J. Am. Chem. Soc. 1984, 106, 2626-2629.
33. Su, C., Oliw, E. H., Manganese lipoxygenase. Purification and characterization. J. Biol. Chem. 1998, 273, 13072-13079.
34. Brash, A. R., Lipoxygenases: Occurrence, functions, catalysis, and acquisition of substrate. J. Biol. Chem. 1999, 274, 23679-23682.
35. Hamberg, M., Su, C., Oliw, E., Manganese lipoxygenase. Discovery of a bis-allylic hydroperoxide as product and intermediate in a lipoxygenase reaction. J. Biol. Chem. 1998, 273, 13080-13088.
36. Oliw, E. H., Factors influencing the rearrangement of bisallylic hydroperoxides by manganese lipoxygenase. J. Lipid Res. 2008, 49, 420-428.
37. Oliw, E. H., Cristea, M., Hamberg, M., Biosynthesis and isomerization of 11-hydroperoxylinoleates by manganese- and iron-dependent lipoxygenases. Lipids 2004, 39, 319-323.
38. Schneider, C., Schreier, P., Catalytic properties of allene oxide synthase from flaxseed (Linum usitatissimum L.). Lipids 1998, 33, 191-196.
39. Hamberg, M., Gerwick, W. H., Åsen, P. A., Linoleic acid metabolism in the red alga Lithothamnion corallioides, Biosynthesis of 11(R)-hydroxy-9(Z),12(Z)-octadecadienoic acid. Lipids 1992, 27, 487-493.