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Chemical Compound Review

Tocopherols     2,7,8-trimethyl-2-(4,8,12...

Synonyms: Methyltocols, E-MIX 80, SureCN39640, AGN-PC-00EZ3W, CHEMBL420898, ...
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Disease relevance of gamma-Tocopherol


Psychiatry related information on gamma-Tocopherol


High impact information on gamma-Tocopherol


Chemical compound and disease context of gamma-Tocopherol


Biological context of gamma-Tocopherol

  • On the other hand, cultivation of target cells with supplemental tocopherol protected them from the toxic effects of the enzymatic oxidant-producing system, indicating a role for membrane-associated free radicals in the mechanism of sister chromatid exchange induction [18].
  • To test whether tocopherols (vitamin E) are essential in the protection against oxidative stress in plants, a series of Arabidopsis thaliana vitamin E (vte) biosynthetic mutants that accumulate different types and levels of tocopherols and pathway intermediates were analyzed under abiotic stress [19].
  • The vte mutant phenotypes also explain the strong selection for retention of tocopherol biosynthesis during the evolution of seed-bearing plants [20].
  • These results confirm that At-VTE3 protein catalyzes the methylation of 2-methyl-6-phytylbenzoquinol in planta and show the utility of this gene in altering soybean tocopherol composition [21].
  • Complementation of the mutation with the wild-type transgene largely restored the wild-type tocopherol phenotype [22].

Anatomical context of gamma-Tocopherol


Associations of gamma-Tocopherol with other chemical compounds


Gene context of gamma-Tocopherol

  • Expression of VTE1 in Escherichia coli resulted in the production of a protein with high tocopherol cyclase and tocotrienol cyclase activity [29].
  • In the presence of PKC or PP2A inhibitors, the reduction of PKB phosphorylation by tocopherols was still observed, thus excluding the direct involvement of these enzymes [30].
  • Thus, the tocopherols interfere with PKB phosphorylation and reduce proliferation of HMC-1 cells, possibly by modulating either phosphatidylinositol 3-kinase, a kinase phosphorylating PKB (PDK1/2), or a phosphatase that dephosphorylates it [30].
  • To investigate whether HPT activity is limiting for tocopherol synthesis in plants, the gene encoding Arabidopsis HPT, HPT1, was constitutively overexpressed in Arabidopsis [31].
  • We describe the cloning and expression of two novel genes highly similar to the tocopherol-associated protein (hTAP/SEC14L2/SPF) [32].

Analytical, diagnostic and therapeutic context of gamma-Tocopherol


  1. Failure of high-dose tocopherol to prevent alopecia induced by doxorubicin. Martin-Jimenez, M., Diaz-Rubio, E., Gonzalez Larriba, J.L., Sangro, B. N. Engl. J. Med. (1986) [Pubmed]
  2. Lack of tocopherol in peripheral nerves of vitamin E-deficient patients with peripheral neuropathy. Traber, M.G., Sokol, R.J., Ringel, S.P., Neville, H.E., Thellman, C.A., Kayden, H.J. N. Engl. J. Med. (1987) [Pubmed]
  3. Adriamycin: the role of lipid peroxidation in cardiac toxicity and tumor response. Myers, C.E., McGuire, W.P., Liss, R.H., Ifrim, I., Grotzinger, K., Young, R.C. Science (1977) [Pubmed]
  4. Effect of vitamin E and beta carotene on the incidence of angina pectoris. A randomized, double-blind, controlled trial. Rapola, J.M., Virtamo, J., Haukka, J.K., Heinonen, O.P., Albanes, D., Taylor, P.R., Huttunen, J.K. JAMA (1996) [Pubmed]
  5. Serologic precursors of cancer. Retinol, carotenoids, and tocopherol and risk of prostate cancer. Hsing, A.W., Comstock, G.W., Abbey, H., Polk, B.F. J. Natl. Cancer Inst. (1990) [Pubmed]
  6. Effect of vitamin E on serum cholesterol and triglycerides in hyperlipidemic patients treated with diet and clofibrate. Leonhardt, E.T. Am. J. Clin. Nutr. (1978) [Pubmed]
  7. Vitamin E and colon cancer: is there an association? Slattery, M.L., Edwards, S.L., Anderson, K., Caan, B. Nutrition and cancer. (1998) [Pubmed]
  8. Tocopherol (vitamin E) in Alzheimer's disease and other neurodegenerative disorders. Berman, K., Brodaty, H. CNS drugs. (2004) [Pubmed]
  9. Concentrations of tocopherols and carotenoids in maternal and cord blood plasma. Kiely, M., Cogan, P.F., Kearney, P.J., Morrissey, P.A. European journal of clinical nutrition. (1999) [Pubmed]
  10. Antioxidant status in anorexia nervosa. Moyano, D., Sierra, C., Brandi, N., Artuch, R., Mira, A., García-Tornel, S., Vilaseca, M.A. The International journal of eating disorders. (1999) [Pubmed]
  11. Tocopherols and the etiology of colon cancer. Stone, W.L., Papas, A.M. J. Natl. Cancer Inst. (1997) [Pubmed]
  12. Impaired ability of patients with familial isolated vitamin E deficiency to incorporate alpha-tocopherol into lipoproteins secreted by the liver. Traber, M.G., Sokol, R.J., Burton, G.W., Ingold, K.U., Papas, A.M., Huffaker, J.E., Kayden, H.J. J. Clin. Invest. (1990) [Pubmed]
  13. Bovine milk lipoprotein lipase transfers tocopherol to human fibroblasts during triglyceride hydrolysis in vitro. Traber, M.G., Olivecrona, T., Kayden, H.J. J. Clin. Invest. (1985) [Pubmed]
  14. Highly divergent methyltransferases catalyze a conserved reaction in tocopherol and plastoquinone synthesis in cyanobacteria and photosynthetic eukaryotes. Cheng, Z., Sattler, S., Maeda, H., Sakuragi, Y., Bryant, D.A., DellaPenna, D. Plant Cell (2003) [Pubmed]
  15. Lower prostate cancer risk in men with elevated plasma lycopene levels: results of a prospective analysis. Gann, P.H., Ma, J., Giovannucci, E., Willett, W., Sacks, F.M., Hennekens, C.H., Stampfer, M.J. Cancer Res. (1999) [Pubmed]
  16. Randomized, placebo-controlled trial of combined pentoxifylline and tocopherol for regression of superficial radiation-induced fibrosis. Delanian, S., Porcher, R., Balla-Mekias, S., Lefaix, J.L. J. Clin. Oncol. (2003) [Pubmed]
  17. Mobilization of triglyceride but not cholesterol or tocopherol from human adipocytes during weight reduction. Schaefer, E.J., Woo, R., Kibata, M., Bjornsen, L., Schreibman, P.H. Am. J. Clin. Nutr. (1983) [Pubmed]
  18. Effects of antioxidants on oxidant-induced sister chromatid exchange formation. Weitberg, A.B., Weitzman, S.A., Clark, E.P., Stossel, T.P. J. Clin. Invest. (1985) [Pubmed]
  19. Tocopherols play a crucial role in low-temperature adaptation and Phloem loading in Arabidopsis. Maeda, H., Song, W., Sage, T.L., Dellapenna, D. Plant Cell (2006) [Pubmed]
  20. Vitamin E is essential for seed longevity and for preventing lipid peroxidation during germination. Sattler, S.E., Gilliland, L.U., Magallanes-Lundback, M., Pollard, M., DellaPenna, D. Plant Cell (2004) [Pubmed]
  21. Engineering vitamin E content: from Arabidopsis mutant to soy oil. Van Eenennaam, A.L., Lincoln, K., Durrett, T.P., Valentin, H.E., Shewmaker, C.K., Thorne, G.M., Jiang, J., Baszis, S.R., Levering, C.K., Aasen, E.D., Hao, M., Stein, J.C., Norris, S.R., Last, R.L. Plant Cell (2003) [Pubmed]
  22. The Arabidopsis vitamin E pathway gene5-1 mutant reveals a critical role for phytol kinase in seed tocopherol biosynthesis. Valentin, H.E., Lincoln, K., Moshiri, F., Jensen, P.K., Qi, Q., Venkatesh, T.V., Karunanandaa, B., Baszis, S.R., Norris, S.R., Savidge, B., Gruys, K.J., Last, R.L. Plant Cell (2006) [Pubmed]
  23. Plastoglobules are lipoprotein subcompartments of the chloroplast that are permanently coupled to thylakoid membranes and contain biosynthetic enzymes. Austin, J.R., Frost, E., Vidi, P.A., Kessler, F., Staehelin, L.A. Plant Cell (2006) [Pubmed]
  24. Vitamin E biosynthesis: biochemistry meets cell biology. Hofius, D., Sonnewald, U. Trends Plant Sci. (2003) [Pubmed]
  25. Reduced tocopherol content of B cells from patients with chronic lymphocytic leukemia. Kayden, H.J., Hatam, L., Traber, M.G., Conklyn, M., Liebes, L.F., Silber, R. Blood (1984) [Pubmed]
  26. Oxidants, antioxidants, and the degenerative diseases of aging. Ames, B.N., Shigenaga, M.K., Hagen, T.M. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  27. Gamma-tocopherol detoxification of nitrogen dioxide: superiority to alpha-tocopherol. Cooney, R.V., Franke, A.A., Harwood, P.J., Hatch-Pigott, V., Custer, L.J., Mordan, L.J. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  28. Isoprenoids: an evolutionary pool for photoprotection. Peñuelas, J., Munné-Bosch, S. Trends Plant Sci. (2005) [Pubmed]
  29. Isolation of an Arabidopsis mutant lacking vitamin E and identification of a cyclase essential for all tocopherol biosynthesis. Porfirova, S., Bergmuller, E., Tropf, S., Lemke, R., Dormann, P. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  30. Inhibition of HMC-1 mast cell proliferation by vitamin E: involvement of the protein kinase B pathway. Kempná, P., Reiter, E., Arock, M., Azzi, A., Zingg, J.M. J. Biol. Chem. (2004) [Pubmed]
  31. Homogentisate phytyltransferase activity is limiting for tocopherol biosynthesis in Arabidopsis. Collakova, E., DellaPenna, D. Plant Physiol. (2003) [Pubmed]
  32. Cloning of novel human SEC14p-like proteins: ligand binding and functional properties. Kempná, P., Zingg, J.M., Ricciarelli, R., Hierl, M., Saxena, S., Azzi, A. Free Radic. Biol. Med. (2003) [Pubmed]
  33. Hepatic tocopherol content in primary hepatocellular carcinoma and liver metastases. Rocchi, E., Seium, Y., Camellini, L., Casalgrandi, G., Borghi, A., D'Alimonte, P., Cioni, G. Hepatology (1997) [Pubmed]
  34. Oxidative stress in fatty livers of obese Zucker rats: rapid amelioration and improved tolerance to warm ischemia with tocopherol. Soltys, K., Dikdan, G., Koneru, B. Hepatology (2001) [Pubmed]
  35. Endothelial relaxation is disturbed by oxidative stress in the diabetic rat heart: influence of tocopherol as antioxidant. Rösen, P., Ballhausen, T., Bloch, W., Addicks, K. Diabetologia (1995) [Pubmed]
  36. Novel HPLC analysis of tocopherols, tocotrienols, and cholesterol in tissue. Katsanidis, E., Addis, P.B. Free Radic. Biol. Med. (1999) [Pubmed]
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