Inhibitory effects of different forms of tocopherols, tocopherol phosphates, and tocopherol quinones on growth of colon cancer cells

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 36, 2013, Pages 8533-8540

  Dolfi, Sonia C ^a   Yang, Zhihong ^a   Lee, Mao Jung ^a   Guan, Fei ^a   Hong, Jungil ^b   Yang, Chung S ^a  

^a RUTGERS UNIVERSITY   (United States)

^b Seoul Women University   (South Korea)

Author keywords

apoptosis; tocopherol; tocopherol quinone; tocopheryl phosphate; uptake

Indexed keywords

CANCER CELL APOPTOSIS; CANCER CELL GROWTH; COLON CANCER CELLS; HUMAN COLON CANCER; INHIBITORY ACTIVITY; TOCOPHEROL; TOCOPHEROL QUINONE; UPTAKE;

PHOSPHATES;

CELL DEATH;

ANTINEOPLASTIC AGENT; PHOSPHATE; QUINONE DERIVATIVE; TOCOPHEROL;

APOPTOSIS; ARTICLE; CELL PROLIFERATION; COLON TUMOR; DRUG EFFECT; HCT116 CELL LINE; HT 29 CELL LINE; HUMAN; METABOLISM; PATHOLOGY;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL PROLIFERATION; COLONIC NEOPLASMS; HCT116 CELLS; HT29 CELLS; HUMANS; PHOSPHATES; QUINONES; TOCOPHEROLS;

EID: 84884271213     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf401076g     Document Type: Article

References (40)

1. Traber, M. G. Vitamin E, 10 th ed.; Lippincott Williams and Wilkins: Baltimore, MD, 2006; pp 396-441.
2. Eitenmiller, R. R.; Lee, J. Vitamin E: Food Chemistry, Composition, and Analysis, 1 st ed.; Marcel Dekker: New York, 2004; p 14.
3. Ju, J.; Picinich, S. C.; Yang, Z.; Zhao, Y.; Suh, N.; Kong, A. N.; Yang, C. S. Cancer-preventive activities of tocopherols and tocotrienols Carcinogenesis 2010, 31, 533-542
4. Lippman, S. M.; Klein, E. A.; Goodman, P. J.; Lucia, M. S.; Thompson, I. M.; Ford, L. G.; Parnes, H. L.; Minasian, L. M.; Gaziano, J. M.; Hartline, J. A.; Parsons, J. K.; Bearden, J. D., 3rd; Crawford, E. D.; Goodman, G. E.; Claudio, J.; Winquist, E.; Cook, E. D.; Karp, D. D.; Walther, P.; Lieber, M. M.; Kristal, A. R.; Darke, A. K.; Arnold, K. B.; Ganz, P. A.; Santella, R. M.; Albanes, D.; Taylor, P. R.; Probstfield, J. L.; Jagpal, T. J.; Crowley, J. J.; Meyskens, F. L., Jr.; Baker, L. H.; Coltman, C. A., Jr. Effect of selenium and vitamin E on risk of prostate cancer and other cancers: The Selenium and Vitamin E Cancer Prevention Trial (SELECT) JAMA, J. Am. Med. Assoc. 2009, 301, 39-51
5. Klein, E. A.; Thompson, I. M., Jr.; Tangen, C. M.; Crowley, J. J.; Lucia, M. S.; Goodman, P. J.; Minasian, L. M.; Ford, L. G.; Parnes, H. L.; Gaziano, J. M.; Karp, D. D.; Lieber, M. M.; Walther, P. J.; Klotz, L.; Parsons, J. K.; Chin, J. L.; Darke, A. K.; Lippman, S. M.; Goodman, G. E.; Meyskens, F. L., Jr.; Baker, L. H. Vitamin E and the risk of prostate cancer: The Selenium and Vitamin E Cancer Prevention Trial (SELECT) JAMA, J. Am. Med. Assoc. 2011, 306, 1549-1556
6. Gaziano, J. M.; Glynn, R. J.; Christen, W. G.; Kurth, T.; Belanger, C.; MacFadyen, J.; Bubes, V.; Manson, J. E.; Sesso, H. D.; Buring, J. E. Vitamins E and C in the prevention of prostate and total cancer in men: The Physicians' Health Study II randomized controlled trial JAMA, J. Am. Med. Assoc. 2009, 301, 52-62
7. Guan, F.; Li, G.; Liu, A. B.; Lee, M. J.; Yang, Z.; Chen, Y. K.; Lin, Y.; Shih, W.; Yang, C. S. δ- and γ-tocopherols, but not α-tocopherol, inhibit colon carcinogenesis in azoxymethane-treated F344 rats Cancer Prev. Res. 2012, 5, 644-654
8. Li, G. X.; Lee, M. J.; Liu, A. B.; Yang, Z.; Lin, Y.; Shih, W. J.; Yang, C. S. δ-Tocopherol is more active than α- or γ-tocopherol in inhibiting lung tumorigenesis in vivo Cancer Prev. Res. 2011, 4, 404-413
9. Yang, C. S.; Suh, N.; Kong, A. N. Does vitamin E prevent or promote cancer Cancer Prev. Res. 2012, 5, 701-705
10. Ju, J.; Hao, X.; Lee, M. J.; Lambert, J. D.; Lu, G.; Xiao, H.; Newmark, H. L.; Yang, C. S. A γ-tocopherol-rich mixture of tocopherols inhibits colon inflammation and carcinogenesis in azoxymethane and dextran sulfate sodium-treated mice Cancer Prev. Res. 2009, 2, 143-152
11. Newmark, H. L.; Huang, M. T.; Reddy, B. S. Mixed tocopherols inhibit azoxymethane-induced aberrant crypt foci in rats Nutr. Cancer 2006, 56, 82-85
12. Lee, H. J.; Ju, J.; Paul, S.; So, J. Y.; DeCastro, A.; Smolarek, A.; Lee, M. J.; Yang, C. S.; Newmark, H. L.; Suh, N. Mixed tocopherols prevent mammary tumorigenesis by inhibiting estrogen action and activating PPAR-γ Clin. Cancer Res. 2009, 15, 4242-4249
13. Suh, N.; Paul, S.; Lee, H. J.; Ji, Y.; Lee, M. J.; Yang, C. S.; Reddy, B. S.; Newmark, H. L. Mixed tocopherols inhibit N-methyl-N-nitrosourea-induced mammary tumor growth in rats Nutr. Cancer 2007, 59, 76-81
14. Barve, A.; Khor, T. O.; Nair, S.; Reuhl, K.; Suh, N.; Reddy, B.; Newmark, H.; Kong, A. N. γ-Tocopherol-enriched mixed tocopherol diet inhibits prostate carcinogenesis in TRAMP mice Int. J. Cancer 2009, 124, 1693-1699
15. Lambert, J. D.; Lu, G.; Lee, M. J.; Hu, J.; Ju, J.; Yang, C. S. Inhibition of lung cancer growth in mice by dietary mixed tocopherols Mol. Nutr. Food Res. 2009, 53, 1030-1035
16. Lu, G.; Xiao, H.; Li, G. X.; Picinich, S. C.; Chen, Y. K.; Liu, A.; Lee, M. J.; Loy, S.; Yang, C. S. A γ-tocopherol-rich mixture of tocopherols inhibits chemically induced lung tumorigenesis in A/J mice and xenograft tumor growth Carcinogenesis 2010, 31, 687-694
17. Jiang, Q.; Yin, X.; Lill, M. A.; Danielson, M. L.; Freiser, H.; Huang, J. Long-chain carboxychromanols, metabolites of vitamin E, are potent inhibitors of cyclooxygenases Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 20464-20469
18. Jiang, Z.; Yin, X.; Jiang, Q. Natural forms of vitamin E and 13′-carboxychromanol, a long-chain vitamin E metabolite, inhibit leukotriene generation from stimulated neutrophils by blocking calcium influx and suppressing 5-lipoxygenase activity, respectively J. Immunol. 2011, 186, 1173-1179
19. Rezk, B. M.; van der Vijgh, W. J.; Bast, A.; Haenen, G. R. Alpha-tocopheryl phosphate is a novel apoptotic agent Front. Biosci. 2007, 12, 2013-9
20. Munteanu, A.; Zingg, J. M.; Ogru, E.; Libinaki, R.; Gianello, R.; West, S.; Negis, Y.; Azzi, A. Modulation of cell proliferation and gene expression by α-tocopheryl phosphates: Relevance to atherosclerosis and inflammation Biochem. Biophys. Res. Commun. 2004, 318, 311-316
21. Mukherjee, S.; Lekli, I.; Das, M.; Azzi, A.; Das, D. K. Cardioprotection with α-tocopheryl phosphate: Amelioration of myocardial ischemia reperfusion injury is linked with its ability to generate a survival signal through Akt activation Biochim. Biophys. Acta 2008, 1782, 498-503
22. Zingg, J. M.; Libinaki, R.; Lai, C. Q.; Meydani, M.; Gianello, R.; Ogru, E.; Azzi, A. Modulation of gene expression by α-tocopherol and α-tocopheryl phosphate in THP-1 monocytes Free Radical Biol. Med. 2010, 49, 1989-2000
23. Gille, L.; Staniek, K.; Rosenau, T.; Duvigneau, J. C.; Kozlov, A. V. Tocopheryl quinones and mitochondria Mol. Nutr. Food Res. 2010, 54, 601-615
24. Calviello, G.; Di Nicuolo, F.; Piccioni, E.; Marcocci, M. E.; Serini, S.; Maggiano, N.; Jones, K. H.; Cornwell, D. G.; Palozza, P. γ-Tocopheryl quinone induces apoptosis in cancer cells via caspase-9 activation and cytochrome c release Carcinogenesis 2003, 24, 427-433
25. Jones, K. H.; Liu, J. J.; Roehm, J. S.; Eckel, J. J.; Eckel, T. T.; Stickrath, C. R.; Triola, C. A.; Jiang, Z.; Bartoli, G. M.; Cornwell, D. G. γ-Tocopheryl quinone stimulates apoptosis in drug-sensitive and multidrug-resistant cancer cells Lipids 2002, 37, 173-184
26. Ogawa, Y.; Saito, Y.; Nishio, K.; Yoshida, Y.; Ashida, H.; Niki, E. γ-Tocopheryl quinone, not α-tocopheryl quinone, induces adaptive response through up-regulation of cellular glutathione and cysteine availability via activation of ATF4 Free Radical Res. 2008, 42, 674-687
27. Schudel, P.; Mayer, H.; Metzger, J.; Rüegg, R.; Isler, O. Über die chemie des vitamins E. 1. Mitteilung. Die umkehrung der konfiguration am kohlenstoffatom 2 von natürlichem (2 R, 4′ R, 8′ R)-α-tocopherol Helv. Chim. Acta 1963, 46, 333-343
28. Cornwell, D. G.; Jones, K. H.; Jiang, Z.; Lantry, L. E.; Southwell-Keely, P.; Kohar, I.; Thornton, D. E. Cytotoxicity of tocopherols and their quinones in drug-sensitive and multidrug-resistant leukemia cells Lipids 1998, 33, 295-301
29. Gianello, R.; Libinaki, R.; Azzi, A.; Gavin, P. D.; Negis, Y.; Zingg, J. M.; Holt, P.; Keah, H. H.; Griffey, A.; Smallridge, A.; West, S. M.; Ogru, E. α-Tocopheryl phosphate: A novel, natural form of vitamin E Free Radical Biol. Med. 2005, 39, 970-976
30. Zhao, Y.; Lee, M. J.; Cheung, C.; Ju, J. H.; Chen, Y. K.; Liu, B.; Hu, L. Q.; Yang, C. S. Analysis of multiple metabolites of tocopherols and tocotrienols in mice and humans J. Agric. Food Chem. 2010, 58, 4844-4852
31. Yang, Z.; Xiao, H.; Jin, H.; Koo, P. T.; Tsang, D. J.; Yang, C. S. Synergistic actions of atorvastatin with γ-tocotrienol and celecoxib against human colon cancer HT29 and HCT116 cells Int. J. Cancer 2010, 126, 852-863
32. Campbell, S. E.; Stone, W. L.; Lee, S.; Whaley, S.; Yang, H.; Qui, M.; Goforth, P.; Sherman, D.; McHaffie, D.; Krishnan, K. Comparative effects of RRR-alpha- and RRR-gamma-tocopherol on proliferation and apoptosis in human colon cancer cell lines BMC Cancer 2006, 6, 13
33. McIntyre, B. S.; Briski, K. P.; Gapor, A.; Sylvester, P. W. Antiproliferative and apoptotic effects of tocopherols and tocotrienols on preneoplastic and neoplastic mouse mammary epithelial cells Proc. Soc. Exp. Biol. Med. 2000, 224, 292-301
34. McIntyre, B. S.; Briski, K. P.; Tirmenstein, M. A.; Fariss, M. W.; Gapor, A.; Sylvester, P. W. Antiproliferative and apoptotic effects of tocopherols and tocotrienols on normal mouse mammary epithelial cells Lipids 2000, 35, 171-80
35. Nishio, K.; Ishida, N.; Saito, Y.; Ogawa-Akazawa, Y.; Shichiri, M.; Yoshida, Y.; Hagihara, Y.; Noguchi, N.; Chirico, J.; Atkinson, J.; Niki, E. α-Tocopheryl phosphate: Uptake, hydrolysis, and antioxidant action in cultured cells and mouse Free Radical Biol. Med. 2011, 50, 1794-800
36. Libinaki, R.; Tesanovic, S.; Heal, A.; Nikolovski, B.; Vinh, A.; Widdop, R. E.; Gaspari, T. A.; Devaraj, S.; Ogru, E. Effect of tocopheryl phosphate on key biomarkers of inflammation: Implication in the reduction of atherosclerosis progression in a hypercholesterolaemic rabbit model Clin. Exp. Pharmacol. Physiol. 2010, 37, 587-92
37. Abushita, A. A.; Daood, H. G.; Biacs, P. A. Change in carotenoids and antioxidant vitamins in tomato as a function of varietal and technological factors J. Agric. Food Chem. 2000, 48, 2075-81
38. Faustman, C.; Liebler, D. C.; Burr, J. A. α-Tocopherol oxidation in beef and in bovine muscle microsomes J. Agric. Food Chem. 1999, 47, 1396-9
39. Verleyen, T.; Verhe, R.; Huyghebaert, A.; Dewettinck, K.; De Greyt, W. Identification of α-tocopherol oxidation products in triolein at elevated temperatures J. Agric. Food Chem. 2001, 49, 1508-11
40. Jiang, Q.; Christen, S.; Shigenaga, M. K.; Ames, B. N. γ-Tocopherol, the major form of vitamin E in the US diet, deserves more attention Am. J. Clin. Nutr. 2001, 74, 714-22