Regioisomeric distribution of cholesteryl linoleate hydroperoxides and hydroxides in plasma from healthy humans provides evidence for free radical- mediated lipid peroxidation in vivo

Journal of Lipid Research

Volumn 41, Issue 1, 2000, Pages 109-115

  Mashima, Ryuichi ^a   Onodera, Koji ^a   Yamamoto, Yorihiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Cholesteryl linoleate hydroperoxides; Free radicals; Human blood plasma; Lipid peroxidation; Regioisomers

Indexed keywords

ARACHIDIC ACID; ARACHIDONATE 15 LIPOXYGENASE; CHOLESTEROL 11,14 EICOSADIENOATE; CHOLESTEROL ESTER; CHOLESTEROL LINOLEATE; FREE RADICAL; HYDROXIDE; LIPID HYDROPEROXIDE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CONTROLLED STUDY; HUMAN; IN VIVO STUDY; LIPID COMPOSITION; LIPID PEROXIDATION; MALE; PLASMA; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOISOMERISM;

ADULT; CHOLESTEROL ESTERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FREE RADICALS; HUMANS; HYDROXIDES; ISOMERISM; LIPID PEROXIDATION; MALE; PEROXIDES; REFERENCE VALUES;

EID: 0033966008     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. Yamamoto, Y., M. H. Brodsky, J. C. Baker, and B. N. Ames. 1987. Detection and characterization of lipid hydroperoxides at picomole levels by high-performance liquid chromatography. Anal. Biochem. 160: 7-13.
2. Yamamoto, Y., and E. Niki. 1989. Presence of cholesteryl ester hydroperoxide in human blood plasma. Biochem. Biophys. Res. Commun. 165: 988-993.
3. Yamamoto, Y., K. Wakabayashi, E. Niki, and M. Nagao. 1992. Comparison of plasma levels of lipid hydroperoxides and antioxidants in hyperlipidemic Nagase analbuminemic rats, Sprague-Dawley rats, and humans. Biochem. Biophys. Res. Commun. 189: 518-523.
4. Porter, N. A., B. A. Weber, H. Weenen, and J. A. Khan. 1980. Autoxidation of polyunsaturated lipids. Factors controlling the stereochemistry of product hydroperoxides. J. Am. Chem. Soc. 102: 5597-5601.
5. Kenar, J. A., C. M. Havrilla, N. A. Porter, J. R. Guyton, S. A. Brown, K. F. Klemp, and E. Selinger. 1996. Identification and quantification of regioisomeric cholesteryl linoleate hydroperoxides in oxidized human low density lipoprotein and high density lipoprotein. Chem. Res. Toxicol. 9: 737-744.
6. Belkner, J., R. Wiesner, H. Kühn, and V. Z. Lankin. 1991. The oxygenation of cholesterol esters by the reticulocyte lipoxygenase. FEBS Lett. 279: 110-114.
7. Belkner, J., R. Wiesner, J. Rathman, E. Sigal, and H. Kühn. 1993. Oxygenation of lipoproteins by mammalian lipoxygenases. Eur. J. Biochem. 213: 251-261.
8. Garner, B., P. K. Witting, A. R. Waldeck, J. K. Christison, M. Raftery, and R. Stocker. 1998. Oxidation of high density lipoproteins. I. Formation of methionine sulloxide in apolipoproteins AI and All is an early event that accompanies lipid peroxidation and can be enhanced by alpha-tocopherol. J. Biol. Chem. 273: 6080-6087.
9. Garner, B., A. R. Waldeck, P. K. Witting, K. A. Rye, and R. Stocker. 1998. Oxidation of high density lipoproteins. II. Evidence for direct reduction of lipid hydroperoxides by methionine residues of apolipoproteins A-I and A-II. J. Biol. Chem. 273: 6088-6095.
10. Mashima, R., S. Yoshimura, and Y. Yamamoto. 1999. Reduction of lipid hydroperoxides by apolipoprotein B-100. Biochem. Biophys. Res. Commun 259: 185-189.
11. Nagata, Y., Y. Yamamoto, and E. Niki. 1996. Reaction of phosphatidylcholine hydroperoxide in human plasma: the role of peroxidase and lecithin:cholesterol acyltransferase. Arch. Biochem. Biophys. 329: 24-30.
12. Peers, K. E., and D. T. Coxon. 1983. Controlled synthesis of monohydroperoxides by α-tocopherol inhibited autoxidation of polyunsaturated lipids. Chem. Phys. Lipids. 32: 49-56.
13. Chan, H. W-S., and G. Levett. 1977. Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates. Lipids. 12: 99-104.
14. 2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc. Natl. Sci. USA. 87: 9383-9387.
15. 2-isoprostanes) in smokers. N. Engl. J. Med. 332: 1198-1203.
16. 2α, in acute coronary angioplasly. Circulation. 96: 3314-3320.
17. 2α in patients with end stage renal failure. Redox Report. 3: 207-211.
18. 2α-I: An index of lipid peroxidation in humans. Proc. Natl. Acad. Sci. USA. 95: 3449-3454.
19. Yamamoto, Y., Y. Nagata, E. Niki, K. Watanabe, and S. Yoshimura. 1993. Plasma glutathione peroxidase reduces phosphatidylcholine hydroperoxide. Biochem. Biophys. Res. Commun. 193: 133-138.