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. 2002 Jun 15;364(Pt 3):625–628. doi: 10.1042/BJ20020491

Evidence for the nitration of gamma-tocopherol in vivo: 5-nitro-gamma-tocopherol is elevated in the plasma of subjects with coronary heart disease.

Lincoln W Morton 1, Natalie C Ward 1, Kevin D Croft 1, Ian B Puddey 1
PMCID: PMC1222608  PMID: 11960550

Abstract

This study investigated the hypothesis that nitration of gamma-tocopherol may be an important mechanism for the detoxification of reactive nitrogen oxide species in vivo. Using liquid chromatography-tandem MS we have shown that gamma-tocopherol can be nitrated in vivo to form 5-nitro-gamma-tocopherol and that concentrations of this compound are elevated in the plasma of subjects with coronary heart disease. In addition, we demonstrate in carotid-artery atherosclerotic plaque that nitration of gamma-tocopherol is also evident at levels similar to that seen in the plasma of subjects with coronary heart disease.

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Selected References

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  1. Christen S., Woodall A. A., Shigenaga M. K., Southwell-Keely P. T., Duncan M. W., Ames B. N. gamma-tocopherol traps mutagenic electrophiles such as NO(X) and complements alpha-tocopherol: physiological implications. Proc Natl Acad Sci U S A. 1997 Apr 1;94(7):3217–3222. doi: 10.1073/pnas.94.7.3217. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Cooney R. V., Franke A. A., Harwood P. J., Hatch-Pigott V., Custer L. J., Mordan L. J. Gamma-tocopherol detoxification of nitrogen dioxide: superiority to alpha-tocopherol. Proc Natl Acad Sci U S A. 1993 Mar 1;90(5):1771–1775. doi: 10.1073/pnas.90.5.1771. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Denicola Ana, Batthyány Carlos, Lissi Eduardo, Freeman Bruce A., Rubbo Homero, Radi Rafael. Diffusion of nitric oxide into low density lipoprotein. J Biol Chem. 2001 Oct 31;277(2):932–936. doi: 10.1074/jbc.M106589200. [DOI] [PubMed] [Google Scholar]
  4. Hensley K., Williamson K. S., Floyd R. A. Measurement of 3-nitrotyrosine and 5-nitro-gamma-tocopherol by high-performance liquid chromatography with electrochemical detection. Free Radic Biol Med. 2000 Feb 15;28(4):520–528. doi: 10.1016/s0891-5849(00)00155-6. [DOI] [PubMed] [Google Scholar]
  5. Hertog M. G., Kromhout D., Aravanis C., Blackburn H., Buzina R., Fidanza F., Giampaoli S., Jansen A., Menotti A., Nedeljkovic S. Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Arch Intern Med. 1995 Feb 27;155(4):381–386. [PubMed] [Google Scholar]
  6. Ischiropoulos H. Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch Biochem Biophys. 1998 Aug 1;356(1):1–11. doi: 10.1006/abbi.1998.0755. [DOI] [PubMed] [Google Scholar]
  7. Jiang Q., Christen S., Shigenaga M. K., Ames B. N. gamma-tocopherol, the major form of vitamin E in the US diet, deserves more attention. Am J Clin Nutr. 2001 Dec;74(6):714–722. doi: 10.1093/ajcn/74.6.714. [DOI] [PubMed] [Google Scholar]
  8. Jiang Q., Elson-Schwab I., Courtemanche C., Ames B. N. gamma-tocopherol and its major metabolite, in contrast to alpha-tocopherol, inhibit cyclooxygenase activity in macrophages and epithelial cells. Proc Natl Acad Sci U S A. 2000 Oct 10;97(21):11494–11499. doi: 10.1073/pnas.200357097. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Kontush A., Spranger T., Reich A., Baum K., Beisiegel U. Lipophilic antioxidants in blood plasma as markers of atherosclerosis: the role of alpha-carotene and gamma-tocopherol. Atherosclerosis. 1999 May;144(1):117–122. doi: 10.1016/s0021-9150(99)00044-1. [DOI] [PubMed] [Google Scholar]
  10. Kristenson M., Ziedén B., Kucinskienë Z., Elinder L. S., Bergdahl B., Elwing B., Abaravicius A., Razinkovienë L., Calkauskas H., Olsson A. G. Antioxidant state and mortality from coronary heart disease in Lithuanian and Swedish men: concomitant cross sectional study of men aged 50. BMJ. 1997 Mar 1;314(7081):629–633. doi: 10.1136/bmj.314.7081.629. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Liu X., Miller M. J., Joshi M. S., Thomas D. D., Lancaster J. R., Jr Accelerated reaction of nitric oxide with O2 within the hydrophobic interior of biological membranes. Proc Natl Acad Sci U S A. 1998 Mar 3;95(5):2175–2179. doi: 10.1073/pnas.95.5.2175. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Ohrvall M., Sundlöf G., Vessby B. Gamma, but not alpha, tocopherol levels in serum are reduced in coronary heart disease patients. J Intern Med. 1996 Feb;239(2):111–117. doi: 10.1046/j.1365-2796.1996.410753000.x. [DOI] [PubMed] [Google Scholar]
  13. Suarna C., Dean R. T., May J., Stocker R. Human atherosclerotic plaque contains both oxidized lipids and relatively large amounts of alpha-tocopherol and ascorbate. Arterioscler Thromb Vasc Biol. 1995 Oct;15(10):1616–1624. doi: 10.1161/01.atv.15.10.1616. [DOI] [PubMed] [Google Scholar]
  14. Waddington E., Sienuarine K., Puddey I., Croft K. Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography. Anal Biochem. 2001 May 15;292(2):234–244. doi: 10.1006/abio.2001.5075. [DOI] [PubMed] [Google Scholar]

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