Phenolic Antioxidants

Critical Reviews in Food Science and Nutrition

Volumn 32, Issue 1, 1992, Pages 67-103

  Shahidi, Fereidoon ^a   Janitha, P K ^a   Wanasundara, P D ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

antioxidants; natural; phenolic; synthetic

Indexed keywords

ANTIOXIDANT; FOOD ADDITIVE; LIPID; PHENOL DERIVATIVE;

CHEMISTRY; FOOD; OXIDATION REDUCTION REACTION; PLANT; REVIEW;

ANTIOXIDANTS; FOOD; FOOD ADDITIVES; LIPIDS; OXIDATION-REDUCTION; PHENOLS; PLANTS, EDIBLE;

EID: 0027021438     PISSN: 10408398     EISSN: 15497852     Source Type: Journal    
DOI: 10.1080/10408399209527581     Document Type: Article

References (111)

1. Abdo, K. M., Rao, G., and Montgomery, C. A., Thirteen week toxicity study of d-α-tocopheryl acetate (vitamin E) in Fisher 344 rats, Food Chem. Toxicol., 24, 1043, 1986.
2. Akaranta, O. and Odozi, T. O., Antioxidant properties of red onion skin tannin extracts, Agric. Wastes, 18, 299, 1986.
3. Anon., Joint FAO/WHO Expert Committee on Food Additives. Tech. Rep. Ser. 751-18. World Health Organization, Geneva, 1987.
4. Aoyama, T., Nakakita, Y., Nakagawa, M., and Sakai, H., Screening for antioxidants of microbiol origin, Agric. Biol. Chem., 46, 2369, 1982.
5. Arai, S., Suzuki, H., Fujimaki, M., and Sakrai, Y., Studies on flavor components in soybeans, II. Phenolic acids in defatted soybean flour, Agric. Biol. Chem., 30, 364, 1966.
6. Barlow, S. M., Toxicological aspects of antioxidants used as food additives, in Food Antioxidants, Hudson, B. J. F., Ed., Elsevier, Amsterdam, 1990, 253.
7. Barylko-Pikielna, N., Contribution of smoke components to sensory, bacteriostatic and antioxidative effects in smoke foods, in Advances in Smoking of Foods, Rutkowski, A., Ed., Pergamon Press, Oxford, 1977 1667.
8. Bateman, L., Hughes, H., and Morris, A. L., Hydroperoxide decomposition in relation to the initiation of radical chain reactions, Discuss. Faraday Soc., 14, 190, 1953.
9. Bateman, L., Olefin oxidation, Q. Rev., 8, 147, 1954.
10. Belitz, H. D. and Grosch, W., Food Chemistry, Springer-Verlag, New York, 1986, 175.
11. Boland, J. L. and Gee, G., Kinetics in the chemistry of rubber and related materials, Trans. Faraday Soc., 42, 236, 1946.
12. Boland, J. L. and ten-Have, P., Kinetics in the chemistry of rubber and related materials; the inhibitory effect of hydroquinone on the thermal oxidation of ethyl linoleate, Trans. Faraday Soc., 43, 201, 1947.
13. Buck, D. F., Food antioxidants — applications and uses in snack foods, Cereal Foods World, 29, 301, 1984.
14. Catignani, G. L. and Carter, M. E., Antioxidant properties of lignin, 47, 1745, 1982.
15. Chan, H. W. S., Photosensitized oxidation of unsaturated fatty acid methyl esters: The identification of different pathways, J. Am. Oil Chem. Soc., 54, 100, 1977.
16. Chang, S. S., Ostric-Matijasevic, B., Hsieh, O. A. L., and Huang, C. L., Natural antioxidants from rosemary and sage, J. Food Sci, 42, 1102, 1977.
17. Chang, H., Prescott, F. F. A., and Swoboda, P. A. T., Thermal decomposition of individual isomers of methyl linoleate hydroperoxide, J. Am. Oil Chem. Soc., 53, 573, 1976.
18. Chipault, J. R., Mizuno, G. R., Hawkins, J. M., and Lundberg, W. P., The antioxidant properties of natural spices, Food Res., 17, 46, 1952.
19. Chipault, J. R., Mizuno, G. R., and Lundberg, W. P., The antioxidant properties of spices in foods, Food Technol., 10, 209, 1956.
20. Cillard, J., Cillard, P., and Cormier, M., Effect of experimental factors on the pro-oxidant behaviour of tocopherol, J. Am. Oil Chem. Soc., 57, 255, 1980.
21. Coppen, P. P., Use of antioxidants, in Rancidity in Foods, Allen, J. C. and Hamilton, R. J., Eds., Applied Science, London, 1983, 76.
22. Dziedzic, S. Z. and Hudson, B. J. F., Hydroxyi-soflavones as antioxidant for edible oils, Food Chem., 11, 161, 1983.
23. Dziedzic, S. Z. and Hudson, B. J. F., Polyhydroxy chalcones and flavanones as antioxidant for edible oils, Food Chem., 12, 205, 1983.
24. Dziezak, J. D., Preservatives: Antioxidants, Food Technol., 9, 94, 1986.
25. Eidridge, A. C. and Kwolek, W. F., Soybean isoflavones: effect of environment and variety on composition, J. Agric. Food Chem., 31, 394, 1983.
26. Endo, Y., Usuki, R., and Kareda, T., Antioxidant effects on chlorophyll and pheophytin on the autoxidation of oils in the dark. II, J. Am. Oil Chem. Soc., 62, 1387, 1985.
27. Erikkson, C. F., Lipid oxidation catalysts and inhibitors in raw materials and processed foods, Food Chem., 9, 3, 1982.
28. Farmer, E. H., Bloomfield, G. F., Sundaralingam, A., and Sutton, D. A., The course and mechanism of autoxidation reactions in olefinic and polyolefinic substances including rubber, Trans. Faraday Soc., 38, 348, 1942.
29. Fukuda, Y., Osawa, T., Namiki, M., and Ozaki, T., Studies on antioxidative substances in sesame seeds, Agric. Biol. Chem., 49, 301, 1985.
30. Gordon, M. H., The mechanism of antioxidant action in vitro, in Food Antioxidants, Hudson, B. J. F., Ed., Elsevier, Amsterdam, 1990, 1.
31. Gunstone, F. D. and Morris, F. A., Lipids in Foods: Chemistry, Biochemistry and Technology, Pergamon Press, Oxford, 1983, 163.
32. Gyorgy, P., Murata, K., and Ikehata, H., Antioxidants isolated from fermented soybean (tempeh), Nature, 203, 870, 1964.
33. Hammerschmidt, P. A. and Pratt, D. E., Phenolic antioxidants of dried soybeans, J. Food Sci., 43, 557, 1978.
34. Hayes, R. E., Bookwalter, G. N., and Bagley, E. B., Antioxidant activities of soybean flour and derivatives—a review, J. Food Sci., 42, 1527, 1977.
35. Hayes, F. and Kato, H., Antioxidative compounds of sweet potatoes, J. Nutr. Sci. Vitaminol., 30, 37, 1984.
36. Hermann, K., Flavanols and flavones in food plants — a review, J. Food Technol., 11, 433, 1976.
37. Herting, D. C. and Durry, E. J. E., α-Tocopherol content of cereal grains and processed cereals, J. Agric. Food Chem., 17, 785, 1969.
38. Houlihan, C. M., Ho, C. T., and Chang, S. S., Elucidation of the chemical structure of novel antioxidant, rosmaridiphenol, isolated from rosemary, J. Am. Oil Chem. Soc., 61, 1036, 1984.
39. Huang, M. F., Inhibition of the mutagenicity of Bay Region diol epoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids, Carcinogenesis, 4, 1631, 1983.
40. Hudson, B. J. F. and Lewis, J. I., Polyhydroxy flavonoid antioxidants for edible oils: structural criteria for activity, Food Chem., 10, 47, 1983.
41. Hudson, B. J. F. and Lewis, J. I., Polyhydroxy flavonoid antioxidants for edible oils: phospholipids as synergists, Food Chem., 10, 111, 1983.
42. Ishikawa, Y. and Yuki, E., Reaction products from various tocopherols with trimethyl oxide and their antioxidative activities, Agric. Biol. Chem., 39, 851, 1975.
43. Ishikawa, Y., Marimoto, K., and Hamasaki, T., Flavoglaucin, a metabolite of Eurotium chavalieri, its oxidation and synergism with tocopherol, J. Am. Oil Chem. Soc., 61, 1864, 1984.
44. Ito, N., Hirose, M., Fukushima, H., Tsuda, T., Shirai, T., and Tatematsu, M., Studies on antioxidants their carcinogenic and modifying effects on chemical carcinogens, Food Chem. Toxicol., 24, 1071, 1986.
45. Kahl, R. and Hildebrandt, A. G., Methodology for studying antioxidant activity and mechanisms of action of antioxidants, Food Chem. Toxicol., 24, 1007, 1986.
46. Kochhar, S. P. and Rossell, J. D., Detection, estimation and evaluation of antioxidants in food systems, in Food Antioxidants, Hudson, B. J. F., Ed., Elsevier, Amsterdam, 1990, 19.
47. Korycka-Daht, M. B. and Richardson, T., Activated oxygen species and oxidation of food constituents, Crit. Rev. Food Sci. Nutr., 10, 209, 1978.
48. Kozlowska, H., Naczk, M., Shahidi, F., and Zadernowski, R., Phenolic acids and tannins in ra~ peseed and canola, in Canola and Rapeseed: ProductionChemistry, Nutrition and Processing Technology, Shahidi, F., Ed., Van Nostrand Reinhold, New York, 1990, 193.
49. Kikugawa, K., Kunugi, A., and Kurechi, T., Chemistry and implication of degradation of phenolic antioxidants, in Food Antioxidants, Hudson, B. J. F., Ed., Elsevier, Amsterdam, 1990, 65.
50. Kikuzaki, H. and Nakatani, N., Structure of a new antioxidative phenolic acid from oregano, Agric. Biol. Chem., 53, 519, 1989.
51. Kurechi, T. and Kato, J., Studies on antioxidants. XI. Oxidation products of concomitant use of BHA and BHT, J. Am. Oil Chem. Soc., 57, 220, 1980.
52. Kurechi, T. and Yamaguchi, T., Studies on antioxidants. X. Oxidation products of concomitant use of BHA and ethyl protocatechuate, J. Am. Oil Chem. Soc., 57, 216, 1980.
53. Kurechi, T., Aizawa, N., and Kunugi, A., Studies on antioxidants. XVIII. Oxidation products of TBHQ. II, J. Am. Oil Chem. Soc., 60, 1878, 1983.
54. Kurechi, T. and Kunugi, A., Studies on antioxidants XVII. Photoxidation products of concomitantly used BHA and PG. J. Am. Oil Chem. Soc., 60, 109, 1983.
55. Kurechi, T. and Kunugi, A., Studies on antioxidants. XIX. Photoxidation products of TBHQ. III, J. Am. Oil Chem. Soc., 60, 1882, 1983.
56. Loliger, J., Natural antioxidants, in Rancidity in Foods, Allen, J. C. and Hamilton, R. J., Applied Science, London, 1983, 100.
57. Lyon, C. K., Sesame, present knowledge of composition and use, J. Am. Oil Chem. Soc., 49, 245, 1972.
58. Mabarouk, A. F. and Dugan, L. R., Kinetic investigation into glucose, fructose and sucrose activated oxidation of methyl linoleate emulsion, J. Am. Oil Chem. Soc., 53, 572, 1961.
59. Maga, J. A., Smoke in Food Processing, CRC Press, Boca Raton, FL, 1988, 99.
60. Matsuzaki, T. and Hara, M., Antioxidative activity of tea leaf catechins, Nippon Nogeikagatu Kai Shi, 59, 129, 1985.
61. Mehta, A. C. and Seshadri, T. R., Flavonoids as antioxidants, J. Sci. Ind. Res., 18B, 24, 1959.
62. Miller, G. J. and Quackenbush, F. W., A comparison of alkylated phenols as antioxidants for lard, J. Am. Oil Chem. Soc., 34, 249, 1957.
63. Murakani, H., Asakawa, T., Terao, J., and Matsushita, S., Antioxidative stability of tempeh and liberation of isoflavones by fermentation, Agric. Biol. Chem., 48, 2971, 1984.
64. Naim, M., Gestetner, B., Zilkah, S., Birk, Y., and Bondi, A., A new isoflavone from soybean, Phytochemistry, 12, 169, 1973.
65. Naim, M., Gestetner, B., Zilkah, S., Birk, Y., and Bondi, A., Soybean isoflavones characterization, detection and anti-fungal activity, J. Agric. Food Chem., 22, 806, 1974.
66. Naim, M., Gestetner, B., Zilkah, S., Birk, Y., and Bondi, A., Antioxidative and antihemolytic activity of soybean isoflavones, J. Agric. Foood Chem., 24, 1174, 1976.
67. Nakadate T., Yamamoto, S., Aizu, E., and Kato, R., Effects of flavonoids and antioxidants on 13-otetradecanoyl phorbol acetate caused epidermal ornithine decarboxylase induction and tumor promotion in relation to lipoxygenase inhibition by these compounds, Gann, 73, 214, 1984.
68. Nakatani, N. and Ikeda, K., Isolation of antioxidative lignan from papua mace, Nippon Kasei Giakkaishi, 79, 1984.
69. Nakatani, N., Inatani, R., Ohta, H., and Nishioka, A., Chemical constituents of pepper (Piper spp.) and application to food preservation for naturally occurring antioxidative compounds, Environ. Health Perspect., 67, 135, 1986.
70. Nakatani, N. and Kikuzaki, H., A new antioxidative glycoside isolated from oregano, Agric. Biol Chem., 51, 2727, 1987.
71. Nakatani, N., Tachibana, Y., and Kikuzaki, H., Medical, biochemical and chemical aspects of free radicals, in Proc. 4th Biennial General Meet. Society for Free Radical Research, Kyoto, 1988, 453.
72. Namiki, M., Antioxidants/antimutagens in food, Crit. Rev. Food Sci. Nutr., 29, 273, 1990.
73. Nawar, W. W., Lipids, in Food Chemistry, Fennema, O. R., Marcel Dekker, New York, 1985, 198.
74. Nergiz, C. and Unal, K., Determination of phenolic acids in virgin olive oil, Food Chem., 39, 237, 1991.
75. Osawa, T., Ramarathnam, N., Kawakishi, S., Namiki, M., and Tashiro, T., Autoxidative defence system in rice hull against damage caused by oxygen radicals, Agric. Biol. Chem., 49, 3085, 1985.
76. Osawa, T., Ramarathnam, N., Kawakishi, S., Namiki, M., and Tashiro, T., Sesamolinol: A novel antioxidant isolated from sesame seeds, Agric. Biol. Chem., 49, 3351, 1985.
77. Osawa, T., Inayoshi, M., Kawakishi, S., Mimura, Y., and Tahara, T., A new antioxidant, tetrahy-drocurcumin, Nippon Nogeikagku Kaishi, 63, 345, 1989.
78. Pokorny, J., Stabilisation of fats by phenolic antioxidants, Can. Inst. Food Technol. J., 4, 68, 1981.
79. Porter, W. L., Recent trends in food applications of antioxidants, in Autoxidation in Food and Biological Systems, Simic, M. G. and Karel, M., Eds., Plenum Press, New York, 1980, 295.
80. Pratt, D. E. and Watts, B. M., The antioxidant activity of vegetable extracts. I. Flavone aglycones, J. Food Sci., 29, 27, 1964.
81. Pratt, D. E., Lipid antioxidants in plant tissues, J. Food Sci., 30, 737, 1965.
82. Pratt, D. E., Water soluble antioxidant activity of soybeans, J. Food Sci., 37, 322, 1972.
83. Pratt, D. E. and Birac, P., Source of antioxidant activity of soybean and soy products, J. Food Sci., 44, 1720, 1979.
84. Pratt, D. E., Pietor, C. D., Porter, W. L., and Giffee, J. W., Phenolic antioxidant of soy protein hydrolysate, J. Food Sci., 47, 24, 1981.
85. Pratt, D. E. and Miller, E. E., A flavonoid antioxidant in Spanish peanuts, J. Am. Oil Chem. Soc., 61, 1064, 1984.
86. Pratt, D. E. and Hudson, B. J. F., Natural antioxidants not exploited commercially, in Food Antioxidants, Hudson, B. J. F., Ed., Elsevier, Amsterdam, 1990, 171.
87. Rackis, J. J., Biologically active compounds, in Soybean Chemistry and Technology, Smith, A. K. and Gircler, S. J., Eds., AVI Publishing, Westport, CT, 1972, 33.
88. Ramanathan, L. and Das, N. P., Studies on the control of lipid oxidation in ground fish by some polyphenolic natural products, J. Agric. Food Chem., 40, 17, 1992.
89. Ramarathnam, N., Osawa, T., Namiki, M., and Tashiro, T., Studies on the relationship between antioxidative activity of rice hull and germination ability of rice seeds, J. Sci. Food Agric., 37, 7019, 1986.
90. Ramarathnam, N., Osawa, T., Namiki, M., and Kawakishi, S., Chemical studies of novel rice antioxidants. II. Identification of isovitexin, a C-glycosyl flavonoid, J. Agric. Food Chem., 37, 316, 1989.
91. Rosenwald, R. H. and Chenicek, J. A., Alkyl hydroxy anisoles as antioxidants, J. Am. Oil Chem. Soc., 28, 185, 1951.
92. Rhee, K. S., Ziprin, Y. A., and Rhee, K. C., Water soluble antioxidant activity of oilseed protein derivatives in model lipid peroxidation system of meat, J. Food Sci., 44, 1132, 1979.
93. Shahidi, F., Wanasundara, P. K. J. P. D., and Hong, C., Antioxidant activity of phenolic compounds in meat model systems, in Phenolic Compounds and Health, American Chemical Society, Washington, D.C., in press.
94. Sheabar, F. Z. and Neeman, I., Separation and concentration of natural antioxidants from the rape of olives, J. Am. Oil Chem. Soc., 65, 990, 1988.
95. Sherwin, E. R., Oxidation and antioxidants in fat and oil processing, J. Am. Oil Chem. Soc., 55, 809, 1978.
96. Schuler, P., Natural antioxidants exploited commercially, in Food Antioxidants, Hudson, B. J. F., Ed., Elsevier, Amsterdam, 1990, 99.
97. Stuckey, B. N., Antioxidants as food stabilizers, in CRC Handbook of Food Additives, Furia, T. E., Ed., CRC Press, Boca Raton, FL, 1972, 185.
98. Su, J.-D., Osawa, T., and Namiki, M., Screening for antioxidant activity of crude drugs, Agric. Biol. Chem., 50, 199, 1986.
99. Su, J.-D., Osawa, T., Kawakishi, S., and Namiki, M., Tannin antioxidants from Osbeckia chinensis, Phytochemistry, 27, 1315, 1988.
100. Takagi, T. and Iida, T., Antioxidant for fats and oils from canary seeds: sterol and triterpin alcohol esters of caffeic acid, J. Am. Oil Chem. Soc., 57, 326, 1980.
101. Tappel, A. L., Vitamin, E., free radical peroxidation of lipids, Ann. N. Y. Acad. Sci., 203, 12, 1972.
102. Tappel, A. L., Vitamin, E., free radical peroxidation of lipids, Ann. N. Y. Acad. Sci., 203, 12, 1972.
103. Tomasi, G., An assessment of the safety of tocoferolsm as food additives, Food Chem. Toxicol., 24, 1051, 1986.
104. Uri, N., Mechanism of antioxidants, in Autoxidation and Antioxidants, Lundbert, W. O., Ed., Wiley Interscience, New York, 1961.
105. VanEsch, G. J., Toxicology of TBHQ, Food Chem. Toxicol., 24, 1063, 1986.
106. Van Der Heijden, C. D., Janseen, P. J. C. M., and Strik, J. J. T. W. A., Toxicology of gallates, a review and evaluation, Food Chem. Toxicol., 24, 1067, 1986.
107. Watanabe, Y. and Ayano, Y., The antioxidative activities of distilled water soluble and ethanol soluble fraction from ground spices, J. Jpn. Soc. Food Nutr., 27, 181, 1974.
108. Whiltern, C. C., Miller, E. E., and Pratt, D. E., Cottonseed flavonoid as lipid antioxidants, J. Am. Oil Chem. Soc., 61, 1075, 1984.
109. Yousseff, A. H. and Rahman, A., Flavonoids of cotton seed and peanut as antioxidants, Riv. Ital. Sostanze Grasse, 42, 147, 1985.
110. Zadernowski, R., Nowak, H., and Kozlowska, H., Natural antioxidants from rapeseeds, in Proc 8th Int. Rapeseed Congress, Vol. 3, McGregor, D. I., Ed., 1991, 883.
111. Ziprin, Y. A., Rhee, K. S., Carpenter, Z. L., Hostetler, R. L., Terrel, R. N., and Rhee, K. C., Glandless cottonseed, peanut and soyprotein ingredients in ground beef patties, effect on rancidity and other quality factors, J. Food Sci., 46, 58, 1981.