Food Processing and Lipid Oxidation

  • J. Bruce German

Abstract

Food lipids are principally triacylglycerides, phospholipids and sterols found naturally in most biological materials consumed as food and added as functional ingredients in many processed foods. As nutrients, lipids, especially triglycerides, are a concentrated caloric source, provide essential fatty acids and are a solvent and absorption vehicle for fat-soluble vitamins and other nutrients. The presence of fat significantly enhances the organoleptic perception of foods, which partly explains the strong preference and market advantage of fat-rich foods. As a class, lipids contribute many desirable qualities to foods, including attributes of texture, structure, mouthfeel, flavor and color. However, lipids are also one of the most chemically unstable food components and will readily undergo free-radical chain reactions that not only deteriorate the lipids but also: (a) produce oxidative fragments, some of which are volatile and are perceived as the off-flavors of rancidity, (b) degrade proteins, vitamins and pigments and (c) cross-link lipids and other macromolecules into non-nutritive polymers. Free-radical chain reactions are thermodynamically favorable, and as a result, evolutionary selection has strongly influenced the chemistry, metabolism and structure of biological cells to prevent these reactions kinetically. However, the loss of native structure and the death of cells can dramatically accelerate the deteriorative reactions of lipid oxidation. The effects of all processing steps, including raw product selection, harvesting, storage, refining, manufacturing and distribution, on the quality of lipids in the final commodity are considerable. Certain key variables now known to influence oxidative processes can be targeted to increase food lipid stability during and after processing. Retention of or addition of exogenous antioxidants is a well-known consideration, but the presence and activity of catalysts, the integrity of tissues and cells, the quantity of polyunsaturated lipids and the structural properties of the final food product, including total surface area of lipids, and the nature of surfactant materials all play important roles in final product stability.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Alexander, J. C.; Chemical and biological properties related to toxicity of heated fats, J. Toxicol. Environ. Health 1981, 7, 125–138.CrossRefGoogle Scholar
  2. Allen, R. R. Hydrogenation. In Bailey’s Industrial Oil and Fat Products; Vol. 2; Swern, D., Ed.; J. Wiley: New York, 1982; pp 1–90.Google Scholar
  3. Ames, B. N. Endogenous oxidative DNA damage, aging, and cancer. Free Radical Res. Commun. 1989, 7, 121–128.CrossRefGoogle Scholar
  4. Ames, B. N.; Shigenaga, M. K.; Hagen, T. M. Oxidants, antioxidants, and the degenerative diseases of aging. Proc. Nat. Acad. Sci. (USA) 1992, 90, 7915–7922.CrossRefGoogle Scholar
  5. Anonymous. The Surgeon Genera’s Report on Nutrition and Health. U.S. Department of Health and Human Services, Publication No. 88–50210. U.S. Government Printing Office: Washington, DC, 1988.Google Scholar
  6. Aruoma, O. I.; Halliwell, B.; Aeschbach, R.; Loligers, J. Antioxidant and proxidant properties of active rose-mary constituents: carnosol and carnosic acid. Xenobiotica 1992,22, 257–268.CrossRefGoogle Scholar
  7. Billek. G., Heated fats in the diet, in The Role of Fats in Human Nutrition, Padley, F. B.; Podmore, J., Eds.; Horwood: Chichester, UK, 1985; pp 163–172.Google Scholar
  8. Buettner, G. R. The pecking order of free radicals and antioxidants: lipid peroxidation, alpha-tocopherol, and ascorbate. Arch. Biochem. Biophys. 1993, 300, 535–543.CrossRefGoogle Scholar
  9. Burton, G.; Ingold, K. I. Autoxidation of biological molecules I. The antioxidant activity of vitamin E and related chain breaking phenolic antioxidants in vitro, J. Am. Chem. Soc. 1981, 103, 6472–6477.CrossRefGoogle Scholar
  10. Buttery, R. G.; Teranishi, R. Gas-liquid chromatography of aroma of vegetables and fruits. Direct injection of aqueous vapors. Anal. Chem. 1961,33, 1439–1441.CrossRefGoogle Scholar
  11. Das, N. P.; Ramanathan, L. Studies on flavonoids and related compounds as antioxidant in food. In Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications; Ong, A. S. H.; Packer, L., Eds.; Birkhauser: Basel, 1992; 295–306.CrossRefGoogle Scholar
  12. Dhopeshwarkar, G.A., Naturally occurring food toxicants: toxic lipids. Prog. Lipid Res. 1980,19, 107–118.CrossRefGoogle Scholar
  13. Drewnowski, A.; Greenwood, M. R. C. Cream and sugar: human preferences for high fat foods. Physiol. Behav. 1983,30, 629-633.CrossRefGoogle Scholar
  14. Drewnowski, A. Taste preferences and food intake. Ann. Rev. Nutr. 1997,17, 237–253.CrossRefGoogle Scholar
  15. Eriksson, C. E; Na, A. Antioxidant agents in raw materials and processed foods. Biochem. Soc. Symp. 1995, 61, 221–234.Google Scholar
  16. Esterbauer, H., Cytotoxicity and genotoxicity of lipid-oxidation products. Am. J. Clin. Nutr. 1993, 57 (Suppl. 5), 779S-786S.Google Scholar
  17. Fielding, C. J.; Bist, A.; Fielding, P. E. Caveolin mRNA levels are up-regulated by free cholesterol and down-regulated by oxysterols in fibroblast monolayers. Proc. Natl. Acad. Sci. USA 1997, 94, 3753–3758.CrossRefGoogle Scholar
  18. Fontana, A.; Antoniazzi, F; Cimino, G.; Mazza, G.; Trivellone, E.; Zanone, B. High-resolution NMR detection of cholesterol oxides in spray dried egg yolk. J. Food Sci. 1992, 57, 869–872.CrossRefGoogle Scholar
  19. Frankel, E. N. The antioxidant and nutritional effects of tocopherols, ascorbic acid and beta-carotene in relation to processing of edible oils. Bibl. Nutr. Dieta 1989,43, 297–312.Google Scholar
  20. Frankel, E. N. Recent advances in lipid oxidation. J. Sci. Food Agric. 1991, 54, 495–511.CrossRefGoogle Scholar
  21. Frankel, E. N.; Huang, S. W.; Kanner, J.; German, J. B. Interfacial phenomena in the evaluation of antioxidants: bulk oils versus emulsions. J. Agric. Food Chem. 1994, 42, 1054–1059.CrossRefGoogle Scholar
  22. Fritsche, K. L.; Johnston, P. V. Rapid autoxidation of fish oil in diets without added antioxidants. J. Nutr. 1988, 118, 425–426.Google Scholar
  23. Gere, A. Decrease in essential fatty acid content of edible fats during the frying process. Z. Ernaehrungswiss 1982, 21, 191–201.CrossRefGoogle Scholar
  24. German, J. B. Muscle lipids. J. Muscle Foods 1989, 1, 339–361.CrossRefGoogle Scholar
  25. Halliwell, B. The role of oxygen radicals in human disease, with particular reference to the vascular system. Haemostasis 1993, 23 (Suppl. 1), 118–126.Google Scholar
  26. Hanasaki, Y; Ogawa, S.; Fukui, S. The correlation between active oxygen scavenging and antioxidative effects of flavonoids. Free Radical Biol. Med. 1994,16, 845–850.CrossRefGoogle Scholar
  27. Hetherington, M. M.; Rolls, B. J. Eating behavior in eating disorders: response to preloads. Physiol. Behav. 1991, 50, 101–108.CrossRefGoogle Scholar
  28. Hopia, A. I.; Huang, S.-W.; Schwarz, K.; German, J. B.; Frankel; E. N. Effect of different lipid systems on antioxidant activity of rosemary constituents carnosol and carnosic acid with and without a-tocopherol. J. Agric. Food Chem. 1996, 44, 2030–2036.CrossRefGoogle Scholar
  29. Huang, S.-W.; Frankel, E. N.; German, J. B. Antioxidant activity of alpha- and gamma-tocopherols in bulk oils and in oil-in-water emulsions. J. Agric. Food Chem. 1994, 42, 2108–2114.CrossRefGoogle Scholar
  30. Huang, S.-W.; Frankel, E. N.; German, J. B. Effects of individual tocopherols and tocopherol mixtures on the oxidative stability of corn oil triglycerides. J. Agric. Food Chem. 1995,43, 2345–2350.CrossRefGoogle Scholar
  31. Huang, S. W.; Frankel, E. N.; Aeschbach, R.; German J. B. (1997) Partition of selected antioxidants in corn oil-water model systems. J. Agric. Food Chem. 1997, 45, 1991–1994.CrossRefGoogle Scholar
  32. Jessup, W.; Rankin, S. M.; De Whalley, C. V.; Hoult, J. R.; Scott, J.; Leake, D. S. Alpha-tocopherol consumption during low-density-lipoprotein oxidation. Biochem. J. 1990, 265, 399–405.Google Scholar
  33. Johnson, S. L.; McPhee, L.; Birch, L. L. Conditioned preferences: young children prefer flavors associated with high dietary fat. Physiol. Behav. 1991,50, 1245–1251.CrossRefGoogle Scholar
  34. Kanner, J.; German, J. B; Kinsella, J. E. Initiation of lipid oxidation in biological systems. Crit. Rev. Food Sci. Nutr. 1987, 25, 317–364.CrossRefGoogle Scholar
  35. Keen, C. L.; German, J. B.; Mareschi, J. P.; Gershwin, M. E. Nutritional modulation of murine models of autoimmunity. Rheum. Dis. Clin. North Am. 1991,17, 223–234.Google Scholar
  36. Larson, R. A. Antoxidant mechanisms of secondary natural products. In Oxidative Stress and Antioxidant Defenses in Biology; Ahmad, S., Ed.; Chapman and Hall: New York, 1995, pp 210–233.CrossRefGoogle Scholar
  37. Laughton, M. J.: Evans, P. J.; Moroney, M. A.; Hoult, J. R.; Halliwell, B. Inhibition of mammalian 5-lipoxygenase and cyclo-oxygenase by flavonoids and phenolic dietary additives. Relationship to antioxidant activity and to iron ion-reducing ability. Biochem. Pharmacol. 1991, 42, 1673–1681.CrossRefGoogle Scholar
  38. Love, J. Mechanism of iron catalysis of lipid oxidation in warmed-over flavor of meat. In Food Lipids and Health; McDonald, R. E.; Min, D. B., Eds.; Marcel Dekker: New York, 1996, pp 269–286.Google Scholar
  39. Miller, K. S; Krochta, J. M. Oxygen and aroma barrier properties of edible films: A review. Trends Food Sci. Tech. 1997, 8, 228–237.CrossRefGoogle Scholar
  40. Morin, R. J.; Peng, S. K. The role of cholesterol oxidation products in the pathogenesis of atherosclerosis. Ann. Clin. Lab. Sci. 1989, 19, 225–237.Google Scholar
  41. Moser, H. A.; Dutton, H. J.; Evans, C. D.; Cowan, J. C. Conducting a taste panel for the evaluation of edible oils. Food Technol. 1950, 4, 105–109.Google Scholar
  42. Muggli, R. Dietary fish oils increase the requirement for vitamin E in humans. In Health Effects of Fish and Fish Oils; Chandra, R. K., Ed.; ARTS Biomedical Publishers and Distributors: St. John’s, Newfoundland, 1989; pp 201–210.Google Scholar
  43. Norris, F. A. Extraction of fats and oils. In Bailey’s Industrial Oil and Fat Products; Vol. 2; Swern, D., Ed.; J. Wiley: New York, 1982; pp 178–245.Google Scholar
  44. Osman, A., M. Wootton, R.S. Baker, A. Arlauskas, and T.M. Bonin, Mutagenic Activity of Heated Potato/Oil Systems, Nutr. Cancer 1983, 5, 146–151.CrossRefGoogle Scholar
  45. Paniangvait, P.; King, A. J.; Jones, A. D.; German, J. B. Cholesterol oxides in foods of animal origin. J. Food Sci. 1995, 60, 1159–1174.CrossRefGoogle Scholar
  46. Porter, N. A.; Caldwell, S. E.; Mills, S. A. Mechanisms of free radical oxidation of unsaturated lipids. Lipids 1995, 30, 277–290.CrossRefGoogle Scholar
  47. Qu, Y. H.; Xu, G. X.; Zhou, J. Z.; Chen, T. D.; Zhu, L. F.; Shields, P. G.; Wang, H. W.; Gao, Y. T. Genotoxicity of heated cooking oil vapors. Mutat. Res. 1992, 298, 105–111.CrossRefGoogle Scholar
  48. Schwarz, K.; Frankel, E. N.; German, J. B. Partition behavior of antioxidative phenolic compounds in heterophasic systems. Fett/Lipid 1996, 98, 115–121.CrossRefGoogle Scholar
  49. Sevanian, A.; Berliner, J.; Peterson, H. Uptake, metabolism, and cytotoxicity of isomeric cholesterol-5,6-epoxides in rabbit aortic endothelial cells. J. Lipid Res. 1991, 32, 147–155.Google Scholar
  50. Simoneau, C; McCarthy, M. J.; Reid, D. S.; German, J. B. Measurement of fat crystallization using NMR imaging and spectroscopy. Trends Food Sci. Technol. 1992, 3, 208–211.CrossRefGoogle Scholar
  51. Smouse, T. H. Significance of lipid oxidation to food processors. In Food Lipids and Health; McDonald, R. E.; Min, D. B., Eds.; Marcel Dekker: New York, 1996; pp 269–286.Google Scholar
  52. St. Angelo, A. J. Lipid oxidation in foods. Crit. Rev. Food Sci. Nutr. 1996, 36, 175–224.CrossRefGoogle Scholar
  53. Steinberg, D.; Parthasarathy, S.; Carew, T. E.; Khoo, J. C; Witztum, J. L. Beyond cholesterol, modifications of low-density lipoprotein that increase its atherogenicity. New Eng. J. Med. 1989, 320. 915–924.CrossRefGoogle Scholar
  54. Teranishi, R.; Buttery, R. G.; Lundin, R. Gas chromatography-direct vapor analyses of food products with programmed temperature control of dual column with dual flame ionization detectors. Anal. Chem. 1962, 34, 1033–1035.CrossRefGoogle Scholar
  55. Terao, J., Piskula, M.; Yao, Q. Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Arch. Biochem. Biophys. 1994, 308, 278–284.CrossRefGoogle Scholar
  56. Tournaire, C; Croux, S.; Maurette, M. T.; Beck, I.; Hocquaux, M.; Braun, A. M.; Oliveros, E. J. Antioxidant activity of flavonoids: efficiency of singlet oxygen (1 delta g) quenching. J. Photochem. Photobiol. B, Biol. 1993, 19, 205–215.CrossRefGoogle Scholar
  57. Warwick, Z. S.; Schiffman, S. S. Role of dietary fat in calorie intake and weight gain. Neurosci. Biobehav. Rev. 1992, 76, 585–596.CrossRefGoogle Scholar
  58. Zhang, W. B.; Addis, P. B. Prediction of levels of cholesterol oxides in heated tallow by dielectric measurement. J. Food Sci. 1990, 55, 1673–1675.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1999

Authors and Affiliations

  • J. Bruce German
    • 1
  1. 1.Department of Food Science and TechnologyUniversity of CaliforniaDavisUSA

Personalised recommendations