Nitration of γ-tocopherol prevents its oxidative metabolism by HepG2 cells

Free Radical Biology and Medicine

Volumn 39, Issue 4, 2005, Pages 483-494

  Wu, Jason H Y ^a   Hodgson, Jonathan M ^a   Ward, Natalie C ^a   Clarke, Michael W ^a   Puddey, Ian B ^a   Croft, Kevin D ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

Cytochrome P450; Metabolism; Nitration; Tocopherol; Vitamin E

Indexed keywords

ANTIDIABETIC AGENT; CHROMAN DERIVATIVE; GAMMA CARBOXYETHYLHYDROXYCHROMAN; GAMMA TOCOPHEROL; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG METABOLISM; DRUG STRUCTURE; DRUG UPTAKE; GAS CHROMATOGRAPHY; HEPATOMA CELL; HUMAN; HUMAN CELL; ISCHEMIC HEART DISEASE; MALE; MASS SPECTROMETRY; NITRATION; NON INSULIN DEPENDENT DIABETES MELLITUS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; URINE;

ADULT; CARCINOMA, HEPATOCELLULAR; CELL LINE, TUMOR; CHROMANS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; GAMMA-TOCOPHEROL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; MALE; PROPIONIC ACIDS; REACTIVE NITROGEN SPECIES;

EID: 22544451582     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2005.04.001     Document Type: Article

References (39)

1. R. Brigelius-Flohe, F.J. Kelly, J.T. Salonen, J. Neuzil, J.M. Zingg, and A. Azzi The European perspective on vitamin E: current knowledge and future research Am. J. Clin. Nutr. 76 2002 703 716
2. Q. Jiang, S. Christen, M.K. Shigenaga, and B.N. Ames gamma-tocopherol, the major form of vitamin E in the US diet, deserves more attention Am. J. Clin. Nutr. 74 2001 714 722
3. K. Hensley, E.J. Benaksas, R. Bolli, P. Comp, P. Grammas, L. Hamdheydari, S. Mou, Q.N. Pye, M.F. Stoddard, G. Wallis, K.S. Williamson, M. West, W.J. Wechter, and R.A. Floyd New perspectives on vitamin E: gamma-tocopherol and carboxyelthylhydroxychroman metabolites in biology and medicine Free Radic. Biol. Med. 36 2004 1 15
4. Y. Yoshida, E. Niki, and N. Noguchi Comparative study on the action of tocopherols and tocotrienols as antioxidant: chemical and physical effects Chem. Phys. Lipids 123 2003 63 75
5. S. Christen, A.A. Woodall, M.K. Shigenaga, P.T. Southwell-Keely, M.W. Duncan, and B.N. Ames gamma-tocopherol traps mutagenic electrophiles such as NO(X) and complements alpha-tocopherol: physiological implications Proc. Natl. Acad. Sci. U. S. A. 94 1997 3217 3222
6. R. Radi Nitric oxide, oxidants, and protein tyrosine nitration Proc. Natl. Acad. Sci. U. S. A. 101 2004 4003 4008
7. Q. Jiang, J. Lykkesfeldt, M.K. Shigenaga, E.T. Shigeno, S. Christen, and B.N. Ames Gamma-tocopherol supplementation inhibits protein nitration and ascorbate oxidation in rats with inflammation Free Radic. Biol. Med. 33 2002 1534 1542
8. S.W. Leonard, R.S. Bruno, E. Paterson, B.C. Schock, J. Atkinson, T.M. Bray, C.E. Cross, and M.G. Traber 5-nitro-gamma-tocopherol increases in human plasma exposed to cigarette smoke in vitro and in vivo Free Radic. Biol. Med. 35 2003 1560 1567
9. L.W. Morton, N.C. Ward, K.D. Croft, and I.B. Puddey Evidence for the nitration of gamma-tocopherol in vivo: 5-nitro-gamma-tocopherol is elevated in the plasma of subjects with coronary heart disease Biochem. J. 364 2002 625 628
10. K.S. Williamson, S.P. Gabbita, S. Mou, M. West, Q.N. Pye, W.R. Markesbery, R.V. Cooney, P. Grammas, U. Reimann-Philipp, R.A. Floyd, and K. Hensley The nitration product 5-nitro-gamma-tocopherol is increased in the Alzheimer brain Nitric. Oxide 6 2002 221 227
11. T.J. Sontag, and R.S. Parker Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status J. Biol. Chem. 277 2002 25290 25296
12. W. Stahl, P. Graf, R. Brigelius-Flohe, W. Wechter, and H. Sies Quantification of the alpha- and gamma-tocopherol metabolites 2,5,7, 8-tetramethyl-2-(2′-carboxyethyl)-6-hydroxychroman and 2,7, 8-trimethyl-2-(2′-carboxyethyl)-6-hydroxychroman in human serum Anal. Biochem. 275 1999 254 259
13. J.E. Swanson, R.N. Ben, G.W. Burton, and R.S. Parker Urinary excretion of 2,7, 8-trimethyl-2-(beta-carboxyethyl)-6-hydroxychroman is a major route of elimination of gamma-tocopherol in humans J. Lipid Res. 40 1999 665 671
14. M. Birringer, D. Drogan, and R. Brigelius-Flohe Tocopherols are metabolized in HepG2 cells by side chain omega-oxidation and consecutive beta-oxidation Free Radic. Biol. Med. 31 2001 226 232
15. S. Christen, Q. Jiang, M.K. Shigenaga, and B.N. Ames Analysis of plasma tocopherols alpha, gamma, and 5-nitro-gamma in rats with inflammation by HPLC coulometric detection J. Lipid Res. 43 2002 1978 1985
16. R.V. Cooney, P.J. Harwood, A.A. Franke, K. Narala, A.K. Sundstrom, P.O. Berggren, and L.J. Mordan Products of gamma-tocopherol reaction with NO2 and their formation in rat insulinoma (RINm5F) cells Free Radic. Biol. Med. 19 1995 259 269
17. W.J. Wechter, D. Kantoci, E.D. Murray Jr., D.C. D'Amico, M.E. Jung, and W.H. Wang A new endogenous natriuretic factor: LLU-alpha Proc. Natl. Acad. Sci. U. S. A. 93 1996 6002 6007
18. F. Galli, R. Lee, J. Atkinson, A. Floridi, and F.J. Kelly gamma-Tocopherol biokinetics and transformation in humans Free Radic. Res. 37 2003 1225 1233
19. H.Y. Huang, and L.J. Appel Supplementation of diets with alpha-tocopherol reduces serum concentrations of gamma- and delta-tocopherol in humans J. Nutr. 133 2003 3137 3140
20. R.S. Parker, T.J. Sontag, and J.E. Swanson Cytochrome P4503A-dependent metabolism of tocopherols and inhibition by sesamin Biochem. Biophys. Res. Commun. 277 2000 531 534
21. N. Miyata, K. Taniguchi, T. Seki, T. Ishimoto, M. Sato-Watanabe, Y. Yasuda, M. Doi, S. Kametani, Y. Tomishima, T. Ueki, M. Sato, and K. Kameo HET0016, a potent and selective inhibitor of 20-HETE synthesizing enzyme Br. J. Pharmacol. 133 2001 325 329
22. V.K. Turan, V.M. Mishin, and P.E. Thomas Clotrimazole is a selective and potent inhibitor of rat cytochrome P450 3A subfamily-related testosterone metabolism Drug Metab. Dispos. 29 2001 837 842
23. W. Zhang, Y. Ramamoorthy, T. Kilicarslan, H. Nolte, R.F. Tyndale, and E.M. Sellers Inhibition of cytochromes P450 by antifungal imidazole derivatives Drug Metab. Dispos. 30 2002 314 318
24. E.A. Podrez, D. Schmitt, H.F. Hoff, and S.L. Hazen Myeloperoxidase- generated reactive nitrogen species convert LDL into an atherogenic form in vitro J. Clin. Invest. 103 1999 1547 1560
25. C. Leeuwenburgh, M.M. Hardy, S.L. Hazen, P. Wagner, S. Oh-ishi, U.P. Steinbrecher, and J.W. Heinecke Reactive nitrogen intermediates promote low density lipoprotein oxidation in human atherosclerotic intima J. Biol. Chem. 272 1997 1433 1436
26. S. Pennathur, C. Bergt, B. Shao, J. Byun, S.Y. Kassim, P. Singh, P.S. Green, T.O. McDonald, J. Brunzell, A. Chait, J.F. Oram, K. O'brien, R.L. Geary, and J.W. Heinecke Human atherosclerotic intima and blood of patients with established coronary artery disease contain high density lipoprotein damaged by reactive nitrogen species J. Biol. Chem. 279 2004 42977 42983
27. A. Ceriello, F. Mercuri, L. Quagliaro, R. Assaloni, E. Motz, L. Tonutti, and C. Taboga Detection of nitrotyrosine in the diabetic plasma: evidence of oxidative stress Diabetologia 44 2001 834 838
28. M. Birringer, P. Pfluger, D. Kluth, N. Landes, and R. Brigelius-Flohe Identities and differences in the metabolism of tocotrienols and tocopherols in HepG2 cells J. Nutr. 132 2002 3113 3118
29. A. Hosomi, M. Arita, Y. Sato, C. Kiyose, T. Ueda, O. Igarashi, H. Arai, and K. Inoue Affinity for alpha-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogs FEBS Lett. 409 1997 105 108
30. N. Landes, P. Pfluger, D. Kluth, M. Birringer, R. Ruhl, G.F. Bol, H. Glatt, and R. Brigelius-Flohe Vitamin E activates gene expression via the pregnane X receptor Biochem. Pharmacol. 65 2003 269 273
31. R. Brigelius-Flohe Vitamin E and drug metabolism Biochem. Biophys. Res. Commun. 305 2003 737 740
32. P.R. Baker, F.J. Schopfer, S. Sweeney, and B.A. Freeman Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation Proc. Natl. Acad. Sci. U. S. A. 101 2004 11577 11582
33. B. Coles, A. Bloodsworth, S.R. Clark, M.J. Lewis, A.R. Cross, B.A. Freeman, and V.B. O'Donnell Nitrolinoleate inhibits superoxide generation, degranulation, and integrin expression by human neutrophils: novel antiinflammatory properties of nitric oxide-derived reactive species in vascular cells Circ. Res. 91 2002 375 381
34. R. Gao, W.L. Stone, T. Huang, A.M. Papas, and M. Qui The uptake of tocopherols by RAW 264.7 macrophages Nutr. J. 1 2002 2
35. N. Noguchi, R. Hanyu, A. Nonaka, Y. Okimoto, and T. Kodama Inhibition of THP-1 cell adhesion to endothelial cells by alpha-tocopherol and alpha-tocotrienol is dependent on intracellular concentration of the antioxidants Free Radic. Biol. Med. 34 2003 1614 1620
36. K. Tran, and A.C. Chan Comparative uptake of alpha- and gamma-tocopherol by human endothelial cells Lipids 27 1992 38 41
37. S.E. Campbell, W.L. Stone, S.G. Whaley, M. Qui, and K. Krishnan Gamma (gamma) tocopherol upregulates peroxisome proliferator activated receptor (PPAR) gamma (gamma) expression in SW 480 human colon cancer cell lines BMC. Cancer 3 2003 25
38. D. Goti, H. Reicher, E. Malle, G.M. Kostner, U. Panzenboeck, and W. Sattler High-density lipoprotein (HDL3)-associated alpha-tocopherol is taken up by HepG2 cells via the selective uptake pathway and resecreted with endogenously synthesized apo-lipoprotein B-rich lipoprotein particles Biochem. J. 332 1998 57 65
39. P. Mardones, and A. Rigotti Cellular mechanisms of vitamin E uptake: relevance in alpha-tocopherol metabolism and potential implications for disease J. Nutr. Biochem. 15 2004 252 260