Tocopherols and Tocotrienols in Cereal Grains

화곡류 종실의 토코페롤과 토코트리에놀 연구현황과 전망

  • 이동진 (단국대학교 생명자원과학대학) ;
  • 이지영 (단국대학교 생명자원과학대학)
  • Published : 2003.12.01

Abstract

Vitamin E is a fat-soluble vitamin that exists in eight different forms, which are $\alpha$, $\beta$, $\gamma$, and $\delta$ tocopherol, and $\alpha$, $\beta$, $\gamma$, and $\delta$ tocotrienol. Tocopherols and tocotrienols are important antioxidant in foods, feeds and their raw materials, where they scavenge lipid radicals. Each form has its own biological activity, the measure of potency or functional use in the body. Antioxidants such as vitamin E act to protect cells against the effects of free radicals, which are potentially damaging by-products of the body's metabolism. Free radicals can cause cell dam-age that may contribute to the development of cardiovascular disease and cancer, The content of tocopherols and tocotrienols vary depending on the environmental condition such as growing regions, temperature, crops and varieties. This report deals with chemical and physical properties and extends to their nutritional and health effect on the tocopherols and tocotrienols in cereal grains.

Keywords

References

  1. Abidi, S. L., T. L. Mounts. 1997. J. Chromatogr. A. 782 : 25 https://doi.org/10.1016/S0021-9673(97)00471-8
  2. Abidi, S.L. 2000. Chromatographic analysis of tocol-derived lipid antioxidants, J. Chromatogr. A. 881: 197-216 https://doi.org/10.1016/S0021-9673(00)00131-X
  3. Ayasolla, K., S. Giri., M. Khan., A. Singh and I. Singh. 2002. Amyloidinduced upregulation of inducible nithc oxide synthase by amy-loid peptide in glial cells : implications to alzheimer's disease.SFRR 2002 PARIS. S186 : 489
  4. Ball, G. H. 1988. Fat-soluble vitamin assays infood analysis: A com-prehensive riview. Elsevier Applid Science, London
  5. Ball, G. H. 1998. Vitamin E, in bioavailability and analysis of vitamins in foods, ed by Ball, G. H. Chapman & Hall. London. : 195-232
  6. Ballesteros, E. Gallego, M., Valcarcel, M. 1996. J. Chromatogr. A. 719 :221 https://doi.org/10.1016/0021-9673(95)00198-0
  7. Balz, M. K., E. Schulte., H. P. Thier. 1992. FatSci. TechnoI, 94 : 209
  8. Balz, M., E. Schulte. and H.-P. Thier. 1992. Trennung von toco- pherolen und tocotrienolen durch HPLC. Fat Sci. Technol. 94 :209-213
  9. Barnes, P. J. 1983. In 'Progress in cereal chemistry and technology.proc. 7th World cereal and bread congress' (J. Holas and J. Kra-tochvil, eds), Elsevier, Amsterdam.: 1095-1100
  10. Blankenhom, G and Clewing S. 1993. Human studies of vitamin Eand rheumatic inflammatory disease, in Vitamin E in Health and Diseas, ed by Packer L and Fuchs J, Marcel-Dekker, New York. :563-575
  11. Bogumila Kupczyk and Marek Gogolewski. 2003. Effect of menadi-one (vitamin K3) addition on lipid oxidation and tocopherols con-tent in plant oils, Nahrung/Food. 47 (1): 11-16 https://doi.org/10.1002/food.200390000
  12. Bourgeois, E. 1992. Determination of vitamin E: Tocopherols andtocotrienots. Elsevier Science Publishers, Barking, Essex
  13. Braanen, A. L. 1975. Toxicology and biochemistry of butylated hydroxyanisole and butylate hydroxytolune. JAOCS 52 : 59-63 https://doi.org/10.1007/BF02901825
  14. Bramley, P. M., I. Elmadfa., A. Kafatos., F. J. Kelly., Y. Manios., H. E.Roxborough., W. Schuch., P. J. A. Sheey., K-H. Wagner. 2000.Review Vitamin E, J. Sci. Food. Agric. 80 : 913-938 https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7<913::AID-JSFA600>3.0.CO;2-3
  15. Buck, D. F. 1981. Eastman chemical products Inc., Kingsport, T. N. J.Am. Oil Chem. Soc., March: 275.
  16. Campbell, S., W. Stone., S. Whaley., K. Khshnan. 2003. Develop-ment of gamma ($\gamma$)-tocophero1 as a colorectal cancer chemopre-ventive agent, Critical Reviews in Oncology/Hematology.47 :249-259 https://doi.org/10.1016/S1040-8428(03)00042-8
  17. Campbell, S., W. Stone., W. Sarah., K. Koyamangalth. 2003. Develop-ment of gamma ($\gamma$)-tocophero1 as a colorectal cancer chemopreven-tive agent, Critical Reviews in Oncology/Hematology. 47 : 249-259 https://doi.org/10.1016/S1040-8428(03)00042-8
  18. Carroll, K. K., Guthrie, N., Nesaretnam, K., Gapor, A., and Chambers, A.F. 1995. Anticancer properties oftocopherols from palm oil, in nutri-tion, lipids, health and disease. Ong, A. S. N., Niki, E. and Packer, L.(eds.) Champaign, IL: Am. Oil Chem. Soc. Press.: 117-121
  19. Chan, R. I. M., H. F. Rosin and W. D. Powrie. 1979. Antimutagenicactivity of vrowning reaction products. Cancer Lett. 15 : 27-33 https://doi.org/10.1016/0304-3835(82)90072-6
  20. Choi, Y. S. 1996. Nutritional evaluation of soybean oil, Kor. Soybean Res. Rep. 13 (I): 7-18
  21. Cillard, J. and P. Cillard. 1980. Behavior of alpha, gamma, and delta tocopherols with linoleic acid in aqueous media. JAOCS. 57 : 39 https://doi.org/10.1007/BF02675523
  22. Cillard, J., Cillard, P., Cormier, M. and Girre, L. 1980. JAOCS. 57 : 252 https://doi.org/10.1007/BF02668254
  23. Cook, M. G. and P. McNamara. 1980. Effect of dietry vitamin E on dimethylhydrazine-induced colonic tumors in mice. Cancer Res 40: 1329-1331
  24. Das, S. 1994. Vitamin E in the geneis and prevention of cancer. A Review. Acta Oncol. 33 ; 615-619 https://doi.org/10.3109/02841869409121771
  25. Day, A. J., and W. D. Brown., A. R. Johnson. 1959. Aust. J. Exp. Biol. Med. Sci. 37 : 295 https://doi.org/10.1038/icb.1959.31
  26. Dolde, D., Vlahakis, C., and Hazebroek, J., 1999. Tocopherols in breeding lines and effrcts of planting location, fatty acid composi-tion, and temperature during development. J. Am. Oil Chem. Soc.76: 349-355 https://doi.org/10.1007/s11746-999-0242-9
  27. Ebata, J., K.. Kawai and H. Furukawa. 1993. Inhibitory effects of dietry leafly vegetables on mutagens and active oxygens. In: Bronzetti, Get al edit, Antimutagenesis and anticarcinogenesis mechanism III,Plenum press, New York. : 99-102
  28. Feeter, D. K. 1974. J. Am. Oil Chem. Soc. 51 : 184 https://doi.org/10.1007/BF02639736
  29. Fredrich. W. 1988. Vitamins. Walter de Gruyter. Berlin. New York.,: 251 Gottstein, T. and Grosch, W. 1990. Fat Sci. Technol. 92 : 139
  30. Hartman, K. T. 1977. J. Am. Oil Chem. Soc. 54 : 421 https://doi.org/10.1007/BF02671024
  31. Hodge, W. K., K. W. Fassett., E. A. Maynard., W. L. Kowns. and R. D.Coye., Jr. 1964. Tosicol. Appl. PharmocoI. 6 : 512 https://doi.org/10.1016/0041-008X(64)90083-3
  32. Hood, R. L 1998. Tocotrienols in metabolism, in phytochemicals-A new paradigm. Bidlack, W. R., Omaye, S. T., Meskin, M. S. and Jahner, D. (eds.) Lancaster, PA : Technomic Publishing Co., Inc. : 33-51
  33. Ikeda, N. and K. Fukuzumi. 1977. Synergistic antioxidant effect ofnucleic acid and tocopherols. JAOCS. 54 : 360 https://doi.org/10.1007/BF02802036
  34. Jung, J. and D-H. Kim. 1982. $\alpha$-Tocopherol as a fluorescent probe its spectroscopic characterization and use as a probe of liposome,J. Korean. AgricuItural Chemical Society. 25 (4): Dec
  35. Kahb, S. G., S. K. Katiyar, R. Agarwakal and H. Mukhta. 1992.Enhancement of antioxidantand phase II enzyme by oral feedinggreen tea polyphenols in drinking water to SHK-l hairless mice; Pos-sible role in cancer chemoprevention. Cancer Res. 52 : 4050-4052
  36. Kamal-Eldin, A. and Andersson R. 1997. Multivariate study of thecorrelation between tocopherol content and fatty acid compositionin vegetable oils. J. Am. Oil Chem. Soc. 74 : 375-380 https://doi.org/10.1007/s11746-997-0093-1
  37. Kamal-Eldin, A., S. Gorgen., J. Pettersson., A-M. Lampi. 2000. Nor-mal-phase high-performance liquid chromatography of toco-pherols and tocotrienols Comparison of different chromatographiccolumns, J. Chromatogr. A. 881 : 217-227 https://doi.org/10.1016/S0021-9673(99)01346-1
  38. Keles, Y., I. Oncel. 2002. Response of antioxidative defence system totemperature and water stress combinations in wheat seedlings,Plant Science. 163 : 783-790 https://doi.org/10.1016/S0168-9452(02)00213-3
  39. Kim, H-G, H-S. Cheigh. 1992. Effect of lipoxygenase on oxidative stablility of $\beta$-carotene and $\alpha$-tocopherol, Korean J. Food Sci.Technol.24(1):37-41
  40. Kim, H-G., H-S. Cheigh. 1995. Oxidative stability of wheat germ lipidand changes in the concentration of carotenoid and tocopherol dur-ing oxidation, Korean J. Food Sci. Technol. 27 (4) : 478-482
  41. Kim, H-J., S-B, Lee., K-A. Park., I-K. Hong. 1999. Characterization of extraction and separation of rice bran oil rich in EFA using SFE process, Separation and Purification Technology. 15 : 1-8 https://doi.org/10.1016/S1383-5866(98)00048-3
  42. Kim, H-L., D-H. Kim. 1972. Relative effectiveness of BHA and Ascorbic acid in retarding the rancidity development of potato chips stored in various conditions, Korean J. Food Sci. Technot. 4 (4): 245-251
  43. Kline, K., Yu, W., and Sanders, B.G. 1998. Vitamin E : mechanism of action of as tumor cell growth inhibitors, in cancer and nutrition Prasad, K-. N. and Cole, W. C. (eds.) Amsterdam, The Netherlands ; I0S. : 37-53
  44. Ko, S-N., C-J. Kim., I-H. Kim. 2003. Effects of roasting condition onthe quality characteristics and oxidative stabilities of rice germ,Korean J. Food Sci. Technol. 35 (3): 347-352
  45. Kong, Z. L., M. Mitsuiki, H. Murakami and H. Omura. 1989. Desmu- tagenicity of furan compounds toward some mutagens. Agric. Biol. Chem. 53 : 2073-2079 https://doi.org/10.1271/bbb1961.53.2073
  46. Lang, J. K., M. Schillaci, and G. Irvin. 1985. Vitamin E, in Modern chromatographic analysis of the vitamins, ed by de Leenheer AP, Lambert WE and de Ruyter MGM. Marcel-Dekker, New York. : 129-200
  47. Lawson, T, J. Nunnally, B. Walker, E. Bresnik, D. Wheeler and M.Wheeler. 1989. Isolation of compounds with anti-mutagenic activityfrom savory chieften cabbage. J. Agric. Food Chem. 37 : 1363-1367 https://doi.org/10.1021/jf00089a034
  48. Lee, H. O. 1993. Antioxidant effect of tocopherols and rocotrienollsand cis/trans-, trans/trans-hydroperoxide isomer from linoleic acidmethylester, Korean J. Food Sci Technol. 25 (4): 307-312
  49. Lee, H. O. 1993. Oxidations product of $\alpha$-, $\gamma$-Tocopherol and $\gamm-tocot-rienol, J. Korean Agric. Chem. Soc. 36 (1): 33-37
  50. Lee, K. L., S. H. Rhee, K. Y. Park and J. O. Kim. 1992. Anti-mutagenic compound identified from perilla leaf (in Korean). J.Korean Soc. Food Nutr. 21 : 302-307
  51. Marks, C. 1988. J. Am. Oil Chem. Soc. 65 : 1936 https://doi.org/10.1007/BF02546011
  52. Marquard, V. 1990. Investigations on the influence of genotype and location on the tocopherol content of the oil from different oil crops. Fat Sci. Technol. 92 : 452-455
  53. Meijboom, P. W., G. A. Jongenotter. 1979. J. Am. Oil Chem. Soc. 56 : 33 https://doi.org/10.1007/BF02671757
  54. Mergens, W., J. J. Kamm, H. L. Newmark, W. Fiddler and J. Pensa- bene. 1978. In Environmental aspects of N-nitrosocompounds:$\alpha$- tocopherol; uses in preventing nitrosamin formation. Walker, E.A.,Casegnaro, M., Griciute, L., and Lyle, R.E., Ed, NoI6 LARC Publi- cation, Lyon, France
  55. Meydani S. N., M. Meydani., J. B. Blumber., L. S. Leka., G. Siber., R. Loszewske., C. Thompson., M. C. Pedrosa., R. D. Diamond and B. D. Stollar. 1997. Vitamin E supplementation and in vivo immuneresponse in healthy elderly sujects. A randomized controlled trial.JAm Med Ass. 277: 1380-1386 https://doi.org/10.1001/jama.277.17.1380
  56. Meydani, S. N. and R. P. Tengerdy. 1993. Vitamin E and immune response, in Vitamin E in Health and Disease, ed by Packer L andFuchs J, Marcel-Dekker, New York..: 549-561
  57. Minkin, V. I., O. A. Osipov, and Y. A. Zhdanov. 1970. In 'Dipole moments in organic chemistry' translation ad. by Vaughan, W. E., p.67, Plenum press, New York
  58. Namiki, M,, S. Udaka, T. Osawa, K. Tsuji and T. Kada. 1980. Formation of ascorbic acid-nitrite reaction: effects of reaction conditions on biological activities. Mutation Res. 73 : 21-28 https://doi.org/10.1016/0027-5107(80)90132-3
  59. Newmark, H. L. 1984. A hypothesis for dietary components as block-ing agents of chemical carcinogenesis: plant phenolics and pyrrolepigments. Nutr. Cancer. 6 : 58-70 https://doi.org/10.1080/01635588509513807
  60. Niki, E., J. Tsuchiya., Y. Yoshikawa., Y. Yamamoto. and Y. K-amiya. 1986. Oxidation of lipids. XIII. Antioxidant activities of $\alpha$-, $\beta$-, $\ga-and $\delta$-tocopherols. Bull. Chem. Soc. Japan. 59 : 497 https://doi.org/10.1246/bcsj.59.497
  61. Osawa, T. 1992. Phenolic antioxidants in dietary plants as anti- mutagen. In: M.T. Huang, C.T. Ho and C. Y. Lee, editors, Phenolic compound in food and their effects on health II. Antioxidants andcancer prevention. ACS. symposium series. 507, American Chemi- cal Society, Washington D.C.: 135-149
  62. Osawa, T., A. Ide, D. S. Jeng and M. Namiki. 1987. Inhibition of lipid peroxidation by ellgic acid, J. Agric. Food Chem. 35 : 808-812 https://doi.org/10.1021/jf00077a042
  63. Patterson, R. E., White, E., Kristal, A.R., Neuhouser, M.L., and Potter, J.D. 1997. Vitamin supplements and cancer risk : the epidemio- logic evidence. Cancer Causes Control. 8 : 786-802 https://doi.org/10.1023/A:1018443724293
  64. Peterson, D. M. and Qureshi, A. A. 1993. Genotype and environmen teffects on tocols of barley and oats. Cereat Chem. 70: 157-162
  65. Piironen, V, E.-L. Syvaoja., P. Varo., K. Salminen. and P. Koivisto- men. 1986. Tocopherols and tocotrienols in cereal products fromfinland. Cereal Chem. 63 : 78-81
  66. Pimmentel and McClellan. 1960. in 'the Hydrogen Bonds' Freeman,San Francisco
  67. Podda, M., C. Weber., M. G. Trber. and L. Packer. 1996. Simultaneous determination of tissue tocopherols, tocotrienols, ubiquinols, and ubiquinones. J. Lipid Res. 37 : 893-901
  68. Qureshi, A. A., H. Mo., L. Packer. and D. M. Peterson. 2000. Isolation and identification of novel tocotrienols from rice bran with hypoc- holesterolemic, antioxidant, and antitumor properties, J. Aeric. Food Chem. 48: 3130-3140 https://doi.org/10.1021/jf000099t
  69. Qureshi, A. A., W. C. Burger., D. M. Peterson. and C. E. Elson. 1986. The structure of an inhibitor of cholesterol biosynthesis isolated from barley. J. BiotogicaI Chemistry, Issue of August 75. 261 (23) : 10544-10550
  70. Ramel, C., U. K. Alekperov, B. N. Ames, T. Kada and L. W. Watten- berg. 1986. Inhibitors of mutagenesis and their relevance to car- cinogenesis. Mutation Res. 168 : 47-65 https://doi.org/10.1016/0165-1110(86)90021-7
  71. Ryu, B. H. 1991. Eating habits preventing against cancer (in Korean). Korean J. Food & Nutrition. 40 : 213-229
  72. Ryu, B. H., D. S. Kim and D. B. Sin. 1989. Antitumor activity of sea weed toward sarcoma-180 (in Korean). Korean J. Food Sci. Technol. 21 (5): 595-599
  73. Ryu, T. H. 1985. Food, nutrition and cancer (in Korean). J. Korean Soc. Food Nutrition. 14 (3): 305-313
  74. Saatomura, Y, Kimura, M., Itokawa, Y. 1992. J. Chromatogr. 625 : 372 https://doi.org/10.1016/0021-9673(92)85224-H
  75. Samejima, K.., K. Kanazawa and G. Nanno. 1995. Luteoline: a strong antimutagen against dietry carcinogen, Trp-P-2 in peppermint, sage and thyme. J. Agric. Food. Chem. 43 : 410-414 https://doi.org/10.1021/jf00050a029
  76. SchueP, W., R. Reattenmaier. 1994. Method Enzymol. 234 : 294 https://doi.org/10.1016/0076-6879(94)34096-X
  77. Sheppard, A. J., J. A. T. Pennington. and J. L. Weihrauch. 1993. Analysis and distribution of vitamin E in vegetable oils and foods, in Vitamin E in health and disease, ed by Packer L and Fuchs J. Mar- cel-Dekker, New York.: 9-31
  78. Shin, T. S. and J. S. Godber. 1993. Improved high-performance liquid chromatography of vitamin E vitamers on normal-phase columns. J. Amer. OiI Chem. Soc. 10: 1289-1290
  79. Shklar, G. and Oh, S.K. 2000. Experimental basis for cancer prevention by vitamin E. Cancer Invest. 18 : 214-222 https://doi.org/10.3109/07357900009031826
  80. Slover, H. T, R. H. Thompson Jr., G. V. Merola. 1983. J. Am. Oil Chem. Soc. 60 : 1524 https://doi.org/10.1007/BF02666576
  81. Sponsler, S. 1996. Food Test Anal. 1 (3): 45
  82. Stampfer, M. J. and Rimm, E. B. 1995. Epidemiologic evidence for vitamin E in prevention of cardiovascular disease. Am. J. Clin. Nutr. 62 : 1365-1369
  83. Stone, W. L., and Papas, A. M. 1997. Tocopherols and the etiology of colon cancer. J. Natl. Cancer lnst. 89 : 1006-1014 https://doi.org/10.1093/jnci/89.14.1006
  84. Summerfield, F. W. and Tappel, A. A. 1984. Effect of dietary polyun- saturated fats and vitamin E on aging and peroxidation damages to DNS. Arch. Biochem. Biophys. 233 : 408-416 https://doi.org/10.1016/0003-9861(84)90462-4
  85. Tsuneo, K., K. Masayuki, A. Katsuhiro and K. Shuhach. 1984 Adsorption of pyrolysate mutagen by vegetable fibers. Mutation Res. 141 : 149-152 https://doi.org/10.1016/0165-7992(84)90088-5
  86. Txsuneo, K., M. Kazuyoshi and I. Tadashi. 1978. Antimutagenic action of vegetable factors on the mutagenic principle of tryp- tothan pyrolysate. Mutation Res. 53 : 351-353
  87. Vinogradov, S. N. and R. H. Linnell. 1971. in 'Hydrogen Bonding',p. 15, Van Nostrand Reinhold Co
  88. Wahyuni, W. T, K. Jinno. 1988. J. Chromatogr. 448 : 398 https://doi.org/10.1016/S0021-9673(01)84602-1
  89. Wattenberg, L. W., J. B. Coccia and L. K. T. Lan. 1980. Inhibitory effects of phenolic compounds on benzo'a'Pyren-induced neoplasia. Cancer Res. 40 : 2820-2823
  90. Weiss, J. J. 1993. Food oil and their uses. 2nd edition, The Avi Pub- lishing Co. Inc., Westport, Connecticut.: 110
  91. White, P. J. and Xing, Y. 1997. Antioxidants from cereals and legumes, in natural antioxidant chemistry, health effects, and appli- cation. Shadihi, F. (eds.) Champaign, IL: Am. Oil Chem. Soc. Press.: 25-63
  92. Wilder, O. H. M., P. C. Ostby. and B. A. Gregoey. 1960. J. Agr. Food Chem. 8 : 504 https://doi.org/10.1021/jf60112a025
  93. Yoon, S-H. and J-W. Kim. 1988. Antioxidative effects of various antiox- idants on the soybean oil, J. Korean Soc. Food Nutr. 17(1): 19-23
  94. Yu, W., M. Simmons-Menchaca., A. Gapor., B. G. Sanders., and K. Kline. 1999. Induction of apoptosis in human breast cancer cells by tocopherols and tocotrienols. Nutr. Cancer. 33 : 26-32 https://doi.org/10.1080/01635589909514744
  95. Zhai, C. K., T. A. Yin, W. R. Yao, D. K. Liu, W. S. Qian. 1992. Analysis of nutritional compositon of chinese wild rice. Acta Nutrimenta Sinica. 14: 210-214
  96. Zhai, D. K., C. M. Lu., X. Q. Zhang., G. J. Sun. and K. J. Lorenz. 2001. Comparative study on nutritional value of chinese and north american wild rice, J. Food Comp. and Anal. 14 : 370-382
  97. Zhang, Y., P. Talalay, C. G. Cho and G. H. Posner. 1992. A major inducer of anticarcinogenic protective enzyme from broccoli. Pro. Natl. Acad. Sci., U.A.S. 89 : 2399-2403 https://doi.org/10.1073/pnas.89.6.2399
  98. Zielinski, H., H. Kozlowska., B. Lewczuk. 2001. Bioactive compounds in the cereal grains before and agter hydrothermal processing, Inno- vative Food Science & Emerging Technologies. 2 : 159-169 https://doi.org/10.1016/S1466-8564(01)00040-6