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Mechanisms of Oxidation of Hydrocarbons, Lipids and Low Density Lipoproteins

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Free Radicals in Biology and Environment

Part of the book series: NATO ASI Series ((ASHT,volume 27))

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Abstract

Low density lipoprotein (LDL) is the major carrier of cholesterol and its esters in human blood plasma. Free radical-peroxidation of LDL may play a crucial role in the development of atherosclerosis, and much effort has been devoted to the study of lipoprotein oxidation and its prevention over the last decade [1, 2]. Peroxidation of the LDL’s lipids affords hydroperoxides principally from cholesteryl linoleate (Ch18:2), the predominant lipid component in the lipoprotein core [3]. Hydroperoxide formation is generally thought to precede and result in the modification of apoprotein B-100, the single protein associated with LDL. Once modified, the apoprotein is taken up by scavenger receptors of monocyte-derived macrophages. Internalization of lipids in this manner is uncontrolled, and leads to intracellular lipid accumulation and the appearance of lipid-laden foam cells similar to those found in early atherosclerotic lesions.

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References

  1. Esterbauer, H., Cheeseman, K. H., eds. (1987) Lipid Peroxidation: Part I Biochemical and Biophysical Aspects. Chem. Phys. Lipids 44, 2–4.

    Google Scholar 

  2. Steinberg, D., Parhasarathy, S., Carew, T. E., Khoo, J. C., Witztum, J. L. (1989) Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320, 915–924 and cited references.

    Google Scholar 

  3. Stocker, R. Bowry, V. W., Frei, B. (1991) Ubiquinol-10 protects human low density lipoprotein more efficiently against lipid peroxidation than does a-tocopherol. Proc. Natl. Acad. Sci. USA 88, 1646–1650.

    CAS  Google Scholar 

  4. For a discussion of the antioxidant effects of a—tocopherol see: Burton, G. W., Ingold, K. U. (1986) Vitamin E: Application of the principles of physical organic chemistry to the exploration of its structure and function. Acc. Chem. Res. 19, 194–201.

    Google Scholar 

  5. Bowry, V. W., Ingold, K. U., Stocker, R., (1992) Vitamin E in human low-density lipoprotein: When and how this antioxidant becomes a pro-oxidant. Biochem. J. 288, 341–344.

    CAS  Google Scholar 

  6. Ingold, K. U., Bowry, V. W., Stocker, R., Walling, C. (1993) Autoxidation of lipids and antioxidation by a-tocopherol and ubiquinol in homogeneous solution and in aqueous dispersions of lipids: Unrecognized consequences of lipid particle size as exemplified by the oxidation of human low density lipoprotein. Proc. Natl. Acad. Sci USA 90, 45–49.

    Article  PubMed  CAS  Google Scholar 

  7. Bowry, V. W., Stocker, R. (1993) Tocopheryl-mediated peroxidation. The prooxidant effect of vitamin E on radical-initiated oxidation of human low-density lipoprotein. J. Am. Chem. Soc. 115, 6029–6044.

    CAS  Google Scholar 

  8. Bowry, V. W., Stanley, K. K., Stocker, R. (1992) High density lipoprotein is the major carrier of lipid hydroperoxides in human blood plasma from fasting donors. Proc. Natl. Acad. Sci USA 89, 10316–10320.

    Article  PubMed  CAS  Google Scholar 

  9. Folcik, V. A., Nivar-Aristy, R. A., Krajewski, J. P., Cathcart, M. K. (1995) Lipoxygenase Contributes to the Oxidation of Lipids in Human Atherosclerotic Plaques. J. Clin. Invest. 96, 504–510.

    Article  PubMed  CAS  Google Scholar 

  10. Corongiu, F., Banni S. (1994) Detection Of Conjugated Dienes By 2nd-derivative Ultraviolet Spectrophotometry. Methods in Enzymology 233, 303–310.

    Article  PubMed  CAS  Google Scholar 

  11. Kenar, J. A., Havrilla, C. M., Porter, N. A., Guyton, J. R., Brown, S. A., Klemp, K. F., Selinger, E. (1996) Identification and Quantification of the Regioisomeric Cholesteryl Linoleate Hydro-peroxides in Oxidized Human Low Density Lipoprotein (LDL) and High Density Lipoprotein (HDL). Chemical Research in Toxicology 9, 737–744.

    Article  PubMed  CAS  Google Scholar 

  12. Porter, N. A., Wujek, D. G. (1984) Autoxidation of polyunsaturated fatty acids, an expanded mechanistic study. J. Am. Chem. Soc. 106, 2626–2629.

    Article  CAS  Google Scholar 

  13. Porter, N. A., Lehman, L. S., Weber, B. A., Smith, K. J. (1981) A Unified Mechanism for Polyunsaturated Fatty Acid Autoxidation: Competition of Peroxy Radical Hydrogen Atom Abstraction, 0-Scission, and Cyclization. J. Am. Chem. Soc. 103, 6447–6455.

    Article  CAS  Google Scholar 

  14. Porter, N. A. (1986) Mechanisms for the Autoxidation of Polyunsaturated Lipids. Acc. Chem. Res. 19, 262–268.

    Article  CAS  Google Scholar 

  15. Porter, N. A., Caldwell, S. E., Mills, K. A. (1995) Mechanisms of Free Radical Oxidation of Unsaturated Lipids. Lipids 30, 277–290.

    Article  PubMed  CAS  Google Scholar 

  16. Sattler, W., Christison, J., Stocker, R. (1995) Cholesterylester hydroperoxide reducing activity associated with isolated high-and low-density lipoproteins. Free Rad. Biol. Med. 18, 421–429.

    Article  PubMed  CAS  Google Scholar 

  17. Sattler, W., Maiorino, M., Stocker, R. (1994) Reduction of HDL- and LDL-associated cholesteryl-ester and phospholipid hydroperoxides by phospholipid hydroperoxide glutathione peroxidase and ebselen (PZ 51). Archives Biochem. Biophys. 309, 214–221.

    Article  CAS  Google Scholar 

  18. Hajjar, D., Nicholson, A. C. (1995) Atherosclerosis. Amer. Scientist 83, 460–467, and references cited therein.

    Google Scholar 

  19. Ku, G., Thomas, C. E., Akeson, A. L., Jackson, R. L. (1992) Induction of interleukin 1-b expression from human peripheral blood monocyte-derived macrophages by 9-hydroxyocta-decadienoic acid. J. Biol. Chem. 267, 14183–14188.

    PubMed  CAS  Google Scholar 

  20. Eling, T. E., Glasgow, W. C. (1994) Cellular proliferation and lipid metabolism: Importance of lipoxygenases in modulating epidermal growth factor-dependent mitogenesis. Cancer and Metastasis Rev. 13, 397–410.

    Article  CAS  Google Scholar 

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Porter, N.A., Havrilla, C.M., Kenar, J.A. (1997). Mechanisms of Oxidation of Hydrocarbons, Lipids and Low Density Lipoproteins. In: Minisci, F. (eds) Free Radicals in Biology and Environment. NATO ASI Series, vol 27. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-1607-9_9

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  • DOI: https://doi.org/10.1007/978-94-017-1607-9_9

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-90-481-4831-8

  • Online ISBN: 978-94-017-1607-9

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