The Antioxidant Functions of Tocopherol and Tocotrienol Homologues in Oils, Fats, and Food Systems

  • Christine M. Seppanen
  • Qinghua Song
  • A. Saari Csallany
Review

Abstract

This review paper is focused on the relative antioxidant activities of tocopherols and tocotrienols in oils and fats and certain food systems. α-Tocopherol generally showed better antioxidant activity than γ-tocopherol in fats and oils, but at higher concentrations γ-tocopherol was found to be a more active antioxidant. The results of studies on the optimum antioxidant concentrations of tocopherols in oils and fats indicated that the optimal level for α-tocopherol is usually lower than other tocopherols, meaning less α-tocopherol is needed for maximum antioxidant protection. There are comparatively very few studies related to the antioxidant activities of tocotrienols in oils and fats. It has been stated that generally γ-tocotrienol has higher antioxidant effect than α-tocotrienol, and tocotrienols may be better antioxidants than their corresponding tocopherols in certain oils and fats systems. Studies on the antioxidant activity of various tocopherols in food systems are varied and cannot be uniformly evaluated because experiments have generally focused on different foods and used various methods for the detection of antioxidant activities. Depending on the food system, in certain cases tocopherols were better antioxidants than synthetic antioxidants such as butylhydroxy toluene (BHT) or butylhydroxy anisole (BHA). However, in certain other food systems the synthetic antioxidants were more effective to increase the shelf life and the stability of foods than those containing tocopherols.

Keywords

Tocopherols Tocotrienols Review paper Antioxidant function Oils Fats Food 

References

  1. 1.
    Evans HM, Bishop KS (1922) On the existence of a hitherto unrecognized dietary factor essential for reproduction. Science 56:650–651CrossRefGoogle Scholar
  2. 2.
    Evans HM (1925) Invariable occurrence of male sterility with dietaries lacking fat soluble vitamin E. Proc Natl Acad Sci USA 11:373–377CrossRefGoogle Scholar
  3. 3.
    Evans HM, Emerson OH, Emerson GA (1936) The isolation from wheat germ oil of an alcohol, α-tocopherol having the properties of vitamin E. J Biol Chem 113:319–332Google Scholar
  4. 4.
    Mason KE (1980) The first two decades of vitamin E history. In: Machlin LJ (ed) Vitamin E: a comprehensive treatise. Marcel Dekker, New York, pp 1–6Google Scholar
  5. 5.
    Stern MH, Robeson CD, Weisler L, Baxter JG (1947) Γ-Tocopherol. I. Isolation from soybean oil and properties. J Am Chem Soc 69:869–874CrossRefGoogle Scholar
  6. 6.
    Pennock JF, Hemming FW, Kerr JD (1964) A reassessment of tocopherol in chemistry. Biochem Biophys Res Commun 17:542–548CrossRefGoogle Scholar
  7. 7.
    Whittle KJ, Dunphy PJ, Pennock JF (1966) The isolation and properties of Δ-tocotrienol from Hevea Latex. Biochem J 100:138–145Google Scholar
  8. 8.
    Azzi A, Stocker A (2000) Vitamin E: non-antioxidant roles. Prog Lipid Res 39:231–255CrossRefGoogle Scholar
  9. 9.
    Bauernfeind JC, Desai ID (1977) The tocopherol content of food and influencing factors. Crit Rev Food Sci Nutr 8:337–382CrossRefGoogle Scholar
  10. 10.
    Schneider C (2005) Chemistry and biology of vitamin E. Mol Nutr Food Res 49:7–30CrossRefGoogle Scholar
  11. 11.
    Kamal-Eldin A, Appelqvist LA (1996) The chemistry and antioxidant properties of tocopherols and tocotrienols. Lipids 31:671–701CrossRefGoogle Scholar
  12. 12.
    Telegdy KL, Berndorfer KE (1968) On the antioxidative mechanism of tocopherols (α-, β-, γ-, δ-) in Lard. Nahrung 12:407–414CrossRefGoogle Scholar
  13. 13.
    Parkhurst RM, Skinner WA, Sturm PA (1968) The effect of various concentrations of tocopherols and tocopherol mixtures on the oxidative stability of a sample of Lard. J Am Oil Chem Soc 45:641–642CrossRefGoogle Scholar
  14. 14.
    Yuki E (1971) Studies on the utilization of a natural tocopherol mixture in fats and fatty foods. I. Comparison of its thermostability with butylated hydroxyanisole by the continuous water-spraying and heating system. J Jpn Oil Chem Soc 20:488–491Google Scholar
  15. 15.
    Cort WM (1974) Antioxidant activity of tocopherols, ascorbyl palmitate, and ascorbic acid and their mode of action. J Am Oil Chem Soc 51:321–325CrossRefGoogle Scholar
  16. 16.
    Ke PJ, Nash DM, Ackman RG (1977) Mackerel skin lipids as an unsaturated fat model system for the determination of antioxidative potency of TBHQ and other antioxidants compounds. J Am Oil Chem Soc 54:417–420CrossRefGoogle Scholar
  17. 17.
    Reinton R, Rogstad A (1981) Antioxidant activity of tocopherols and ascorbic acid. J Food Sci 46:970–971CrossRefGoogle Scholar
  18. 18.
    Hudson BJF, Ghavami M (1984) Stabilising factors in soybean oil-natural components with antioxidant activity. Lebensm Wiss Technol 17:82–85Google Scholar
  19. 19.
    Lampi AM, Piironen V (1998) α- and γ-Tocopherols as efficient antioxidants in butter oil triacylglycerols. Fett-Lipid 100:292–295CrossRefGoogle Scholar
  20. 20.
    Kanno C, Hayashi M, Yamauchi K, Tsugo T (1970) Antioxidant effect of tocopherols on autoxidation of milk fat. I. Antioxidant activity of tocopherols in fatty acid methyl esters of milk fat. Agric Biol Chem 34:878–885Google Scholar
  21. 21.
    Hamilton RJ, Kalu C, McNeill GP, Padley FB, Pierce JH (1998) Effects of tocopherols, ascorbyl palmitate, and lecithin on autoxidation of fish oil. J Am Oil Chem Soc 75:813–822CrossRefGoogle Scholar
  22. 22.
    Kulas E, Ackman RG (2001) Properties of α-, γ-, and Δ-tocopherol in purified fish oil triacylglycerols. J Am Oil Chem Soc 78:361–367CrossRefGoogle Scholar
  23. 23.
    Réblová Z (2006) The effect of temperature on the antioxidant activity of tocopherols. Eur J Lipid Sci Tech 108:858–863CrossRefGoogle Scholar
  24. 24.
    CheMan YB, Jialong L, Liu JL (1999) The effects of TBHQ and α-tocopherol on quality characteristics of refined, bleached and deodorized palm olein during deep-fat frying. J Food Lipids 6:117–129CrossRefGoogle Scholar
  25. 25.
    Jung MY, Choe E, Min DB (1991) α-, γ-, and Δ-tocopherol effects on chlorophyll photosensitized oxidation of soybean oil. J Food Sci 56: 807–810, 815Google Scholar
  26. 26.
    Fuster MD, Lampi AM, Hopia A, Kamal-Eldin A (1998) Effects of α- and γ-tocopherols on the autooxidation of purified sunflower triacylglycerols. Lipids 33:715–722CrossRefGoogle Scholar
  27. 27.
    Lampi AM, Kataja L, Kamal-Eldin A, Vieno P (2000) Antioxidant activities of α- and Γ-tocopherols in the oxidation of rapeseed oil triacylglycerols. J Am Oil Chem Soc 76:749–755CrossRefGoogle Scholar
  28. 28.
    Yanishlieva NV, Kamal-Eldin A, Marinova EM, Toneva AG (2002) Kinetics of antioxidant action of α- and Γ-tocopherols in sunflower and soybean triacylglycerols. Eur J Lipid Sci Technol 104:262–270CrossRefGoogle Scholar
  29. 29.
    Makinen M, Kamal EA, Lampi AM, Hopia A (2000) Effects of α- and Γ-tocopherol on formation of hydroperoxides and two decomposition products from methyl linoleate. J Am Oil Chem Soc 77:801–806CrossRefGoogle Scholar
  30. 30.
    Isnardy B, Wagner KH, Elmadfa I (2003) Effects of alpha-, gamma-, and delta-tocopherols on the autoxidation of purified rapeseed oil triacylglycerols in a system containing low oxygen. J Agric Food Chem 51:7775–7780CrossRefGoogle Scholar
  31. 31.
    Önal B, Ergin G (2002) Antioxidative effects of alpha-tocopherol and ascorbyl palmitate on thermal oxidation of canola oil. Nahrung 46:420–426CrossRefGoogle Scholar
  32. 32.
    Nogala-Kalucka M, Korczak J, Elmadfa I, Wagner KH (2005) Effect of alpha- and delta-tocopherol on the oxidative stability of a mixed hydrogenated fat under frying conditions. Eur Food Res Tech 221:291–297CrossRefGoogle Scholar
  33. 33.
    Aoyama M, Maruyana T, Niiya I, Akatsuka S (1986) Antioxidant effect of tocopherols on palm oil by frying tests. J Jpn Soc Food Sci Technol 34:714–719Google Scholar
  34. 34.
    Aoyama M, Maruyana T, Niiya I, Akatsuka S (1986) Effect of addition of tocopherols on oxidative stability of potato chips. J Jpn Soc Food Sci Technol 33:407–413Google Scholar
  35. 35.
    Nenadis N, Zafiropoulou I, Tsimidou M (2003) Commonly used food antioxidants: a comparative study in dispersed systems. Food Chem 82:403–407CrossRefGoogle Scholar
  36. 36.
    Chaiyasit W, McClements DJ, Decker EA (2005) The relationship between the physicochemical properties of antioxidants and their ability to inhibit lipid oxidation in bulk oil and oil-in-water emulsions. J Agric Food Chem 53:4982–4988CrossRefGoogle Scholar
  37. 37.
    Khafizov RKH, Nadirov NK, Sibirtsev AI, Kazzhan ZM (1970) The effect of tocopherols on soybean oil resistance to oxidation. Izv Vuz Pishch Tekh 5:30–33Google Scholar
  38. 38.
    Shishkov D, Shunanov G, Andreev A (1979) Quantitative composition and antioxidative action of tocopherols contained in vegetable oils rendered by various technological means. Nauchni Trudove, Institut po Rastitelni, Protein i Mieshchi Sredstva 3:17–22Google Scholar
  39. 39.
    Timmermann F, Adams WF (1989) Antioxidant effect of tocopherols and ascorbyl palmitate. Eur Food Drink Rev 48:51–52Google Scholar
  40. 40.
    Clark JP, Huncker JC, Megremis CJ (1990) Tocopherols: nature’s antioxidant. Food Aust 42:262–263Google Scholar
  41. 41.
    Jung MY, Min DB (1990) Effects of α-, γ-, and Δ-tocopherol on oxidative stability of soybean oil. J Food Sci 55:1464–1465CrossRefGoogle Scholar
  42. 42.
    Jung MY, Min DB (1992) Effects of oxidized α-, γ-, and Δ-tocopherol on the oxidative stability of purified soybean oil. Food Chem 45:183–187CrossRefGoogle Scholar
  43. 43.
    Yoshida H, Kajimoto G, Emura S (1993) Antioxidant effects of Δ-tocopherols at different concentrations in oils during microwave heating. J Am Oil Chem Soc 70:989–995CrossRefGoogle Scholar
  44. 44.
    Huang SW, Frankel EN, German JB (1994) Antioxidant activity of α- and Γ-tocopherols in bulk oil and in oil-in-water emulsions. J Agric Food Chem 42:2108–2114CrossRefGoogle Scholar
  45. 45.
    Huang SW, Frankel EN, German JB (1995) Effects of individual tocopherols and tocopherol mixtures on the oxidative stability of corn oil. J Agric Food Chem 43:2345–2350CrossRefGoogle Scholar
  46. 46.
    Blekas G, Tsimidou M, Boskou D (1995) Contribution of α-tocopherol to olive oil stability. Food Chem 52:289–294CrossRefGoogle Scholar
  47. 47.
    Evans JC, Kodali DR, Addis PB (2002) Optimal tocopherol concentrations to inhibit soybean oil oxidation. J Am Oil Chem Soc 79:47–51CrossRefGoogle Scholar
  48. 48.
    Kajimoto G, Yoshida H, Miyake S (1970) Relationship between heat stability of tocopherol derivatives and synergist. J Jpn Soc Food Nutr 23:437–442Google Scholar
  49. 49.
    Ha KH, Igarashi O (1990) The oxidation products from two kinds of tocopherols co-existing in autoxidation system of methyl linoleate. J Nutr Sci Vitaminol 36:411–421Google Scholar
  50. 50.
    Yoshida H, Hirooka N, Kajimoto G (1991) Microwave heating effects on relative stabilities of tocopherols in oils. J Food Sci 56:1042–1046CrossRefGoogle Scholar
  51. 51.
    Yoshida H, Kondo I, Kajimoto G (1992) Effects of microwave energy on the relative stability of vitamin e in animal fats. J Sci Food Agric 58:531–534CrossRefGoogle Scholar
  52. 52.
    Seher A, Ivanov SA (1973) Natural antioxidants: I. Antioxidative action of tocotrienols. Fette Seifen Anstrichm 75:606–608CrossRefGoogle Scholar
  53. 53.
    Yamaoka M, Tanaka A, Kato A (1985) Antioxidative activity of tocotrienols. Yukagaku 34:120–122Google Scholar
  54. 54.
    Top ABG, Ong ASH, Kato A, Watanabe H, Kawada T (1989) Antioxidant activities of palm vitamin e with special reference to tocotrienols. ELAEIS: Int J Palm Oil Res Dev 1:63–67Google Scholar
  55. 55.
    Feng HP (1996) Preparative techniques for isolation of vitamin e homologues and evaluation of their antioxidant activities. Diss Abstr Int B 56:5243Google Scholar
  56. 56.
    Wagner KH, Wotruba F, Elmadfa I (2001) Antioxidative potential of tocotrienols and tocopherols in coconut fat at different oxidation temperatures. Eur J Lipid Sci Technol 103:746–751CrossRefGoogle Scholar
  57. 57.
    Romero N, Robert P, Masson L, Ortiz J, González K (2006) Effect of alpha-tocopherol and rosa mosqueta shell extract on the performance of antioxidant-stripped canola oil (Brassica Sp.) at high temperature. Food Chem 104:383–389CrossRefGoogle Scholar
  58. 58.
    Kuwahara M, Uno H, Fujiwara A, Yoshikawa T, Uda I (1971) Antioxidative effect of natural vitamin E on lard used for frying instant ramen. I. Effect of natural vitamin e of various concentration in comparison to synthetic antioxidants. J Food Sci Technol 18:64–69Google Scholar
  59. 59.
    Kuwahara M, Uno H, Fujiwara A, Yoshikawa T, Uda I (1971) Antioxidative effect of natural vitamin E on lard used for frying instant ramen. II. Antioxidative effect of natural vitamin E for commercial production. J Food Sci Technol 18:70–74Google Scholar
  60. 60.
    Rho KL, Seib PA (1990) Antioxidant effect of tocopherols in instant fried noodles (Ramyon). ASEAN Food J 5:12–16Google Scholar
  61. 61.
    Kanematsu H, Morise E, Niiya I, Imamura M, Matsumoto A, Katsui G (1972) Influence of tocopherols on oxidative stability of margarines. J Jpn Soc Food Nutr 25:343–348Google Scholar
  62. 62.
    King CC (1986) Effects of antioxidants and modified atmosphere on the storage stability of the pecan kernel. Diss Abstr Int B 47:1347Google Scholar
  63. 63.
    Ochi T, Tsuchiya K, Aoyama M, Maruyama T, Niiya I (1988) Effects of tocopherols on qualitative stability of cookies and influence of powdered milk and egg. J Jpn Soc Food Sci Technol 35:259–264Google Scholar
  64. 64.
    Inagaki C, Igarashi O, Arakawa N, Ohta T (1968) Antioxidative components in the flavedo oil from unshu-orange. J Agric Chem Soc Jpn 42:731–734Google Scholar
  65. 65.
    Mallet JF, Cerrati C, Ucciani E, Gamisans J, Gruber M (1994) Antioxidant activity of plant leaves in relation to their α-tocopherol content. Food Chem 49:61–65CrossRefGoogle Scholar
  66. 66.
    Taga MS, Miller EE, Pratt DE (1984) Chia seeds as a source of natural lipid antioxidants. J Am Oil Chem Soc 61:928–931CrossRefGoogle Scholar
  67. 67.
    Elez-Martínez P, Soliva-Fortuny R, Martín-Belloso O (2007) Oxidative rancidity in avocado puree as affected by Α-tocopherol, sorbic acid and storage atmosphere. Eur Food Res Technol 226:295–300CrossRefGoogle Scholar
  68. 68.
    Frankel EN (1996) Antioxidants in lipid foods and their impact on food quality. Food Chem 57:51–55CrossRefGoogle Scholar

Copyright information

© AOCS 2010

Authors and Affiliations

  • Christine M. Seppanen
    • 1
  • Qinghua Song
    • 1
  • A. Saari Csallany
    • 1
  1. 1.Department of Food Science and NutritionUniversity of MinnesotaSt. PaulUSA

Personalised recommendations