Skip to main content
SpringerLink
Log in
Book cover

Nutritional and Toxicological Consequences of Food Processing pp 255–268Cite as

Dietary N-3 Polyunsaturated Fatty Acids of Fish Oils, Autoxidation ex vivo and Peroxidation in vivo: Implications

  • Chapter

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 289))

Abstract

Because of their apparent efficacy in reducing the occurrence of a number of pathophysiologies related to heart disease, thrombosis, inflammation and immune functions the omega (w), or n-3polyunsaturated fatty acids (n-3 PUFA) of seafoods and fish oils are receiving much attention (Kinsella et al., 1990a,b,c). Increased consumption of n-3 PUFA is being promoted and products containing n-3 PUFA are being developed. The n-3 PUFA being highly unsaturated have a tendency to undergo rapid autoxidation and cause off-flavors (Hsieh and Kinsella, 1989). Hence, there is some concern about the potential deleterious effects resulting from peroxidation of n-3 PUFA, especially in vivo.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Begin, M.E., Ells, G. and Das, U.N. (1986) Selected fatty acids as possible intermediates for selective cytotoxic activity of anticancer agents involving oxygen radicals. Anticancer Res. 6(2), 291–5.

    CAS  Google Scholar 

  • Begin M.E. (1987) Effects of polyunsaturated fatty acids and of their oxidation products on cell survival. Chem. Phvs. Lipids. 45(2–4), 269–313.

    Article  CAS  Google Scholar 

  • Burton, G.W. and Ingold, K.U. (1986) Vitamin E applications of the principles of physical organic chemistry to the exploration of its structure and function. Acc. Chem. Res. 19, 194.

    Article  CAS  Google Scholar 

  • Chan, H.W. (1987) Autoxidation of unsaturated lipids. Academic Press, London.

    Google Scholar 

  • Charnock, J.S., Abeywardena, M.Y. and McLellan, R.L. (1986) Comparative changes in the fatty acid composition of rat cardiac phospholipids after long-term feeding of sunflower seed oil or tuna fish oil supplemented diets. Ann. Nutr. Metab. 30:393–406.

    Article  CAS  Google Scholar 

  • Charnock, J.S., Turner, J. and Macintosh, G.H. (1987) The occurrence of cardiac lipidosis and the chronic lesions in the hearts of rats following long term feeding of different lipid supplemented diets. J. Nutr. Sci. Vitaminol. 33, 75.

    Article  CAS  Google Scholar 

  • Chaudiere, J., Clement, M., Driss, J. and Bourre, J.M. (1987) Unaltered brain membranes after prolonged intake of highly oxidizable long-chain fatty acids of the (n-3) series. Neurosci-Lett. 82(2), 233–9.

    Article  CAS  Google Scholar 

  • Corrocher, R., Ferrari, S., de-Gironcoli, M., Bassi, A., Olivieri, O., Guarini, P., Stanziai, A., Barba, A.L. and Gregolini, L. (1989) Effect of *fish* oil supplementation on erythrocyte lipid pattern, malondialdehyde production and glutathioneperoxidase activity in psoriasis. Clin. Chem. Acta. 179(2), 121–31.

    Article  CAS  Google Scholar 

  • Cosgrove, J.P., Church, D.F. and Prior, W.A. (1987) The kinetics of the autoxidation of polyunsaturated fatty acids. Lipids. 22(5), 299–304.

    Article  CAS  Google Scholar 

  • Croset, M., Guichardant, M. and Lagarde, M. (1988) Different metabolic behavior of long chain n-3 PUFA in human platelets. Biochim. Biophvs. Acta. 961, 262.

    Article  CAS  Google Scholar 

  • Curtis-Prior, P.B. (1988) Prostaglandins, Biology and Chemistry of Prostaglandins and Related Eicosanoids. Churchill Livingston, NY.

    Google Scholar 

  • Das, U.N., Huang, Y.S., Begin, M.E., Ellis, G. and Horrobin, D.F. (1987) Uptake and distribution of cis-unsaturated fatty acids and their effect on free radical generation in normal and tumor cells in vitro. Free Radic. Biol. Med. 3, 9–14.

    Article  CAS  Google Scholar 

  • Dhanakoti, S.N. and Drapper, H.H. (1987) Response of urinary malondioldehyde to factors that stimulate lipid peroxidation in vivo. Lipids 22, 643.

    Article  CAS  Google Scholar 

  • Duthie, G., Arthur, J.R. and Mills, C.F. (1987) Tissue damage in vitamin E deficient rats is not detected by expired ethane and pentane. Free Radical Research Commun. 4, 21.

    Article  CAS  Google Scholar 

  • Fiatmark, T., Nilsson, A., Kvannes, J., Eikhom, T.S., Fukami, M.H., Kryvi, H. and Christiansen, E.N. (1988) On the mechanism of induction of the enoyme systems for peroxisomal beta-oxidation of fatty acids in rat liver by diets rich in partially hydrogenated fish oil. Biochem. Bioohvs. Acta. 962(1), 122–30.

    Article  Google Scholar 

  • Frankel, E.N., Hu, M.L. and Tappet, A.L. (1989) Rapid head space gas chromatography as a measure of lipid peroxidation in biological samples. Lipids 24, 976.

    Article  CAS  Google Scholar 

  • Fox, P.L. and DiCorleto, P.E. (1988) Fish oils inhibit endothelial cell production of platelet-derived growth factor-like protein. Science 241(4864), 453–6.

    Article  CAS  Google Scholar 

  • Frankel, E.N. (1987) Secondary products of lipid oxidation. Chem. Phvs. Lipids 44, 73.

    Article  CAS  Google Scholar 

  • Frankel, E.N. (1987) Biological significance of secondary lipid oxidation products. Free Rad. Res. Comm. 3, 213.

    Article  CAS  Google Scholar 

  • Fritsche, K. and Johnston, P.V. (1988) Rapid autoxidation of fish oil in diets without added antioxidants. J. Nutr. 118:425.

    CAS  Google Scholar 

  • Hagve, T.A. and Christophersen, B.O. (1986) Evidence for peroxisomal retrocon version of adrenic acid (22:4(n-6)) and docosahexaenoic acids (22:6(n-3)) in isolated liver cells. Biochem. Biophvs. Acta. 875(2), 165–73.

    Article  CAS  Google Scholar 

  • Harris, W.S. (1989) Fish oils and plasma lipid and lipoprotein metabolism in humans: A critical review. J. Lipid Res. 30. 785.

    CAS  Google Scholar 

  • Hartog, J.N., Glammers, J.M., Montfoort, A., Becker, A.E., Klompe, N., Morse, H., Tencate, F.J., Vanderwert, L., Huelsman, N.W.C., Hugenholtz, P. and Verdouw, P.D. (1987) Comparison of mackerel oil and lard fed enriched diets on plasma lipids, cardiac membrane phospholipids, cardiovascular performance and morphology in young pigs. Am. J. Clin. Nutr. 46, 258.

    CAS  Google Scholar 

  • Hietanen, E., Ahotupa, M., Bereziat, J.C., Bussacchini, V., Camus, A.M. and Bartsch, H. (1987) Elevated lipid peroxidation in rats induced by dietary lipids and N-nitrosodimethylamine and its inhibition by indomethacin monitored via ethane exhalation. Toxicol. Pathol. 15(1), 93–6.

    Article  CAS  Google Scholar 

  • Hock, E.C., Holahan, M.A. and Reibel, D.K. (1987) Effect of dietary fish oil on myocardial phospholipids and myocardial ischemic damage. Am. J. Phvsiol. 252, H554–H560.

    CAS  Google Scholar 

  • Horton, A.A. and Fairhurst, S. (1987) Lipid peroxidation and mechanisms of toxicity. CRC Rev. in Toxicology 18:27.

    Article  CAS  Google Scholar 

  • Hsieh, R. and Kinsella, J.E. (1989) Oxidation of polyunsaturated fatty acids: Mechanisms, products and inhibition with emphasis on fish. Advances Food & Nutr. Res. 33, 233.

    Article  CAS  Google Scholar 

  • Jubb, J.V., Kennedy, P.C., and Palmer, N. (1985) Pathology of domestic animals 3rd edition, Academic Press, Orlando, FL.

    Google Scholar 

  • Kanner, J., German, B. and Kinsella, J.E. (1987) Initiation of lipid peroxidation in biological systems. Crit. Rev. Food Sci. and Nutr. 25, 317.

    Article  CAS  Google Scholar 

  • Karmali, R.A. (1987) Omega-3 fatty acids and Cancer: A review. In Polyunsaturated Fatty Acids and Eicosanoids. Lands, W.E.M., editor, Champaign, IL. AOCS p. 225.

    Google Scholar 

  • Ke, P.J., Nash, D. and Ackman, R.G. (1977) Mackerel skin lipids as an unsaturated fat model system for determination of antioxidant potency of TBHQ and other antioxidant compounds. J. Am. Oil. Chem. Soc. 54. 417.

    Article  CAS  Google Scholar 

  • Kinsella, J.E. (1987) Seafoods and Fish Oils in Human Health and Disease. Marcel Dekker, Inc. Publishers, NY. p. 1–400.

    Google Scholar 

  • Kinsella, J.E., Lokesh, B. and Stone, R. (1989) Dietary n-3 polyunsaturated fatty acids and amelioration of cardiovascular disease: Possible mechanisms. Am. J. Clin. Nutr. 46 (press).

    Google Scholar 

  • Kinsella, J.E., Broughton, S.K. and Whelan, J.W. (1990) Dietary unsaturated fatty acids: interactions and possible needs in relation to eicosanoid synthesis. J. Nutr. Biochem. 1, 123–141.

    Article  CAS  Google Scholar 

  • Kinsella, J.E. and Lokesh, B. (1990) Dietary lipids, eicosanoids and the immune system. Critical Care Med. 18(2), S94–S113.

    CAS  Google Scholar 

  • Kockmann, V., Vericel, E., Croset, M. and Lagarde, M. (1988) Vitamin E fails to alter the aggregation and oxygenated metabolism of arachidonic acid in normal human platelets. Prostaelandins. 36, 67.

    Google Scholar 

  • Lamers, J.M., Hartog, J.M., Guarins, F., Vaona, I., Verdouw, P.D. and Koster, J.F. (1988) Lipid peroxidation in normoxic and ischaemic-reperfused hearts of fish oil and lard fat fed pigs. J. Mol. Cell. Cardiol. 20(7), 605–15.

    Article  CAS  Google Scholar 

  • Lamers, J.M., Hartog, J.M, Verdouw, P.D. and Hulsamm, W.C. (1987) Dietary fatty acids and myocardial function. Basic Res. Cardiol. 82 Suppl 1., 209–21.

    CAS  Google Scholar 

  • Lands, W.E.M. (1986) Fish and Human Health. Academic Press, Orlando, FL.

    Google Scholar 

  • Lands, W.E.M. Editor. (1987) Polyunsaturaed fatty acids and eicosanoids. Am. Oil Chem. Soc, Champaign, IL.

    Google Scholar 

  • Lands, W.E.M. (1985) Interactions of lipid hydroperoxides with eicosanoid biosynthesis. J. Free Rad. Biol. Med. 1, 97.

    Article  CAS  Google Scholar 

  • Lands, W.E.M. and Kulmac, R.J. (1986) The regulation of the biosynthesis of prostaglandins and leukotrienes. Prog. Lioid Res. 25, 105.

    Article  CAS  Google Scholar 

  • Lands, W.E.M., Miller, J.F. and Rich, S. (1987) Influence of dietary fish oil on plasma lipids hydroperoxides. Advance PG. TX and Leukotr. Res. 17, 876.

    Google Scholar 

  • Leaf, A. and Weber, P.C. (1988) Cardiovascular effects of n-3 fatty acids. New Eng. J. Med. 318. 549.

    Article  CAS  Google Scholar 

  • Leedle, R.A. and Aust, S.D. (1986) Importance of the polyunsaturated fatty acid to vitamin E ration in the resistance of rat lung microsomes to lipid peroxidation. J. Free. Radic. Biol. Med. 2(5-6), 397–403.

    Article  CAS  Google Scholar 

  • Leika, L.S., Remali, K.M., Bizinkausakas, P.A. and Meydani, M. (1989) Effect of fish oil in intestinal absorption of vitamin E in the rat. FASEB J. 3, #4214.

    Google Scholar 

  • McKenzie, G.G., McKenzie, J.B. and Mccollum, E.V. (1941) J. Nutr. 5, 21, 225.

    Google Scholar 

  • Marx, J.L. (1987) Oxygen free radicals linked to many diseases. Science 235, 529.

    Article  CAS  Google Scholar 

  • Matsuo, N. (1961) Studies on the toxicity of fish oil. Toxicity of Autoxidized unsaturated fatty acid ester applied to rat. Tokushima. J. Exot. Med. 8, 90.

    CAS  Google Scholar 

  • McCord, J.M. (1985) Oxygen derived free radicals in post-ischemie tissue injury. New Engl. J. Med. 312. 159.

    Article  CAS  Google Scholar 

  • Meydani, S.N., Yogeesarran, G., Liu, S., Baskar, F. and Meydani, M. (1988) Fish oil and tocopherol induced changes in natural killer cell-mediated cytotoxicity and PGE2 synthesis in young and old mice. J. Nutr. 118, 1245.

    CAS  Google Scholar 

  • Meydani, S.N., Shapiro, S.C., Meydani, M., Macaulley, J.V. and Blumberg, J.B. (1987) Effect of age and dietary fat on tocopherol status of C57BL mice. Lipids 22, 345.

    Article  CAS  Google Scholar 

  • Meydani, S.N., Stocking, L.M., Shapiro, A.C., Meydani, M. and Blumberg, J.B. (1988) Fish oil and tocopherol induced changes in ex-vivo synthesis of spleen and lung leukotriene B4 in mice. Ann. NY Acad. Sci. 524:395–398.

    Article  Google Scholar 

  • Meydani, S.N., Shapiro, S.C., Meydani, M., Macaulley, J.V. and Blumberg, J.B. (1987) Effect of age and dietary fat on tocopherol status of C57BL mice. Lipids 22, 345.

    Article  CAS  Google Scholar 

  • Meydani, S.N., Stocking, L.M., Shapiro, A.C., Meydani, M. and Blumberg, J.B. (1988) Fish oil and tocopherol induced changes in ex-vivo synthesis of spleen and lung leukotriene B4 in mice. Ann. NY Acad. Sci. 524:395–398.

    Article  Google Scholar 

  • Mounie, J.B., Faye, J., Maqdalou, H., Gondonnet, R., Reuchot, and Siest, G. (1986) Modulation of UDP glucoronosyltransferase activity in rats by dietary lipids. J. Nutr. 116,2034.

    CAS  Google Scholar 

  • Muggli, R. (1989) Dietary fish oils increase the requirement for vitamin E in humans. In Health Effects of Fish and Fish Oils, Chandra, S.K. editor, ARTS Press, St. Johns, Newfoundland, 1989.

    Google Scholar 

  • Nalbone, G., Termine, E., Leonardi, J., Portugal, H., Lechene, P., Calaf, R., Lafonte, R. and Lafonte, H. (1988) Effect of dietary salmon oil feeding on rat heart lipid status. J. Nutr. 118.809–17.

    CAS  Google Scholar 

  • Nalbone, G., Leonardi, J., Termine, E., Portugal, H., Lechene, P., Pauli, A.M. and Lafonte, H. (1989) Effects of fish oil, corn oil and lard diets on lipid peroxidation status and glutathione peroxidase activities in rat heart. Lipids 24, 179.

    Article  CAS  Google Scholar 

  • Nelson, G.J. and Ackman, R. (1988) Absorption and transport of fat in mammals with emphasis on n-3 polyunsaturated fatty acids. Lipids 23, 1005.

    Article  CAS  Google Scholar 

  • Nelson, R.L., Tenaure, J.C., Andrianopolous, G., Souza, and Lands, W.E. (1988) A comparison of dietary fish oil and corn oil in experimental colo-rectal carcinogenesis. Nutr. Cancer 11, 215.

    Article  CAS  Google Scholar 

  • O’Connor, T.P., Roebuck, B.D., Peterson, F.J., Lokesh, B., Kinsella, J.E. and Campbell, T. (1989) Effect of dietary w-3 fatty acids on development of azaserien induced preneoplastic lesions in rat pancreas. J. Natl. Cancer Institute 81, 858.

    Article  Google Scholar 

  • Olivieri, O, Negri, M., De-Gironcoli, M., Bassi, A., Guarini, P., Stanziai, A.M., Grigolini, L., Ferrari, S. and Corrocher, R. (1988) Effects of dietary fish oil on malondialdehyde production and glutathione peroxidase activity in hyperlipidaemic patients. Scand. J. Clin. Lab. Invest. 48(7), 659–65.

    Article  CAS  Google Scholar 

  • Piche, L.A., Draper, H.H. and Cole, P.D. (1988) Malendehyde excretion by subjects consuming cod liver oil and a concentrate of n-3 fatty acids. Lioids 23, 370.

    Article  CAS  Google Scholar 

  • Pompella, A., Maellaro, E., Casine, A., Ferrali, M. Ciccoli, L. and Comporti, M. (1987) Measurement of lipid peroxidation in vivo, a comparison of different procedures. Lioids 22, 206.

    Article  CAS  Google Scholar 

  • Rasheed, A.A., Oldfield, J., Kaufmes, J., Sinnhuber, R.O. (1963) Nutritional value of marine oils. 1. Menhaden oil at varying oxidation levels with and without antioxidants in rat diets. J. Nutr. 79, 323.

    CAS  Google Scholar 

  • Ruiter, A., Jung-Bloed, W., Vangent, CM., Danse, L.H. and Metts, S.H. (1978) The influence of dietary mackerel oil on the condition of organ and on blood lipid composition in the young growing pig. Am. J. Clin. Nutr. 31, 2159.

    CAS  Google Scholar 

  • Shapiro, A.C., Meydani, S.N., Meydani, M., Blumberg, J., Andres, S. and Dinarello, C. The effect of fish oil supplementation on human plasma alphatocopherol levels. In Health Effects of Fish and Fish Oils, R.K. Chandra editor. St. Johns Newfoundland, Canada, Press, (1989).

    Google Scholar 

  • Shapiro, A., Meydani, S., Meydani, N. and Shaeffer, A.E. (1989) Effect of fish oil supplementation on plasma alpha-tocopherol, retinol, triglyceride and cholesterol levels. FASEB Abstr. #4204, FASEB J. 3.

    Google Scholar 

  • Swanson, J.E. and Kinsella, J.E. (1986) Dietary n-3 polyunsaturated fatty acids: modification of rat crdiac lipids and fatty acid composition. J. Nutr. 116:514–523.

    CAS  Google Scholar 

  • Tappel, A. (1973) Lipid peroxidation damage to cell components. Fed. Proc. 32, 1870.

    CAS  Google Scholar 

  • Wade, A., Bellows, J. and Dharwadkar, S. (1986) Influence of dietary menhaden oil on enoymes metabolzing drugs and carcinogens. Drug. Nutr. Interactions 4, 339.

    CAS  Google Scholar 

  • Warso, M.A. and Lands, W.E.M. (1984) Presence of lipid hydroperoxide in human plasma. J. Clin. Invest. 75, 667.

    Article  Google Scholar 

  • Willis, A.L. (1987) Handbook of Eicosanoids, Prostaglandins and Related Compounds. CRC Press, Boca Rato, FL.

    Google Scholar 

  • Yamazaki, R.K., Shen, T. and Schade, G.B. (1987) A diet rich in (n-3) fatty acids increases peroxisomal beta-oxidation activity and lowers plasma triacylglycerols without inhibiting glutathione-dependent detoxication activities in the rat liver. Biochem. Biophvs. Acta. 920(1), 62–7.

    Article  CAS  Google Scholar 

  • Yagi, K. Lipid peroxides in biology and medicine. Academic Press, NY. (1982).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Food Science, Cornell University, Ithaca, NY, 14853, USA

    John E. Kinsella

Authors
  1. John E. Kinsella
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. U.S. Department of Agriculture, Albany, California, USA

    Mendel Friedman

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Springer Science+Business Media New York

About this chapter

Cite this chapter

Kinsella, J.E. (1991). Dietary N-3 Polyunsaturated Fatty Acids of Fish Oils, Autoxidation ex vivo and Peroxidation in vivo: Implications. In: Friedman, M. (eds) Nutritional and Toxicological Consequences of Food Processing. Advances in Experimental Medicine and Biology, vol 289. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-2626-5_18

Download citation

  • DOI: https://doi.org/10.1007/978-1-4899-2626-5_18

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-2628-9

  • Online ISBN: 978-1-4899-2626-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation