Dietary advanced lipid oxidation endproducts are risk factors to human health

Molecular Nutrition and Food Research

Volumn 51, Issue 9, 2007, Pages 1094-1101

  Kanner, Joseph ^a  

^a VOLCANI CENTER   (Israel)

Author keywords

ALEs; Diet; Lipid oxidation; Oxycholesterols; Reactive carbonyls

Indexed keywords

ANTIOXIDANT; LIPID PEROXIDE;

ANIMAL; DIET; FOOD; GASTROINTESTINAL TRACT; HUMAN; INTESTINE ABSORPTION; LIPID PEROXIDATION; METABOLISM; REVIEW; RISK FACTOR;

ANIMALS; ANTIOXIDANTS; DIET; FOOD; GASTROINTESTINAL TRACT; HUMANS; INTESTINAL ABSORPTION; LIPID PEROXIDATION; LIPID PEROXIDES; RISK FACTORS;

ANIMALIA;

EID: 34948892098     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.200600303     Document Type: Review

References (83)

1. Addis, P. B., Occurrence of lipid oxidation products in foods, Food Chem. Toxicol. 1986, 24, 1021-1030.
2. Kanner, J., German, J. B., Kinsella, J. E., Initiation of lipid peroxidation in biological systems, Crit. Rev. Food Sci. Nutr. 1987, 25, 317-364.
3. Kubow, S., Routes of formation and toxic consequences of lipid oxidation products in foods, Free Radic. Biol. Med. 1992, 12, 63-81.
4. German, J. B., Food processing and lipid oxidation, Adv. Exp. Med. Biol. 1999, 459, 23-50.
5. Hung, H. C., Joshipura, J. K., Jiang, R., Hu, F. B., et al., Fruit and vegetable intake and risk of major chronic disease, J. Natl. Cancer Inst. 2004, 96, 1577-1584.
6. Hu, F., J., Willett, W. C., Optimal diets for prevention of coronary heart disease, Am. Med. Assoc. 2002, 288, 2569-2578.
7. Steffen, L. M., Jacobs, D. R., Jr., Stevens, J., Shahar, E., et al., Associations of whole-grain, refined-grain, and fruit and vegetable consumption with risks of all-cause mortality and incident coronary artery disease and ischemic stroke: the Atherosclerosis Risk in Communities (ARIC) Study, Am. J. Clin. Nutr. 2003, 78, 383-390.
8. Riboli, E., Norat, T., Epidemiologic evidence of the protective effect of fruit and vegetables on cancer risk, Am. J. Clin. Nutr. 2003, 78, 5598-5698.
9. Terry, P., Giovannucci, E., Michels, K. B., Bergkvist, L., et al., Fruit, vegetables, dietary fiber, and risk of colorectal cancer, J. Natl. Cancer Inst. 2001, 93, 525-533.
10. Goldstein, J. L., Brown, M. S., The low-density lipoprotein pathway and its relation to atherosclerosis, Annu. Rev. Biochem. 1977, 46, 897-930.
11. Steinberg, D., Parthasarathy, S., Carew, T. E., Khoo, J. C., Witztum, J. L., Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity, N. Engl. J. Med. 1989, 320, 915-924.
12. Stocker, R., Keaney, J. F., Jr., New insights on oxidative stress in the artery wall, J. Thromb. Haemost. 2005, 3, 1825-1834.
13. Conn, J., Oxidized fat in the diet, postprandial lipaemia and cardiovascular disease, Curr. Opin. Lipidol. 2003, 13, 19-24.
14. Kanner, J., Oxidative processes in meat and meat products: quality implications, Meat Sci. 1994, 36, 169-189.
15. Gorelik, S., Lapidot, T., Shaham, I., Granit, R., et al., Lipid peroxidation and coupled vitamin oxidation in simulated and human gastric fluid inhibited by dietary polyphenols: health implications, J. Agric. Food Chem. 2005, 53, 3397-3402.
16. Frankel, E., Lipid Oxidation, The Oil Press, Dundee 1998.
17. Wolff, S. P., Nourooz-Zadeh, J., Hypothesis: UK consumption of dietary lipid hydroperoxides - a possible contributory factor to atherosclerosis, Atherosclerosis 1996, 119, 261-263.
18. Shacham, I., MSc. Thesis, Hebrew University of Jerusalem 2006.
19. Chang, S. S., Peterson, R. J., Ho, C. T., Chemical reactions involved in the deep-fat frying of foods, J. Am. Oil Chem. Soc. 1978, 56, 718-727.
20. Esterbauer, H., Schaur, R. J., Zolhner, H., Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes, Free Radic. Biol. Med. 1991, 11, 81-128.
21. Uchida, K., Role of reactive aldehyde in cardiovascular diseases, Free Redic. Biol. Med. 2000, 28, 1685-1696.
22. Sakai, T., Yamauchi, K., Kuwazuru, S., Gotoh, N., Relationships between 4-hydroxy-2-nonenal, 2-thiobarbituric acid reactive substances and n-6 polyunsaturated fatty acids in refrigerated and frozen pork, Biosci. Biotechnol. Biochem. 1998, 62, 2028-2029.
23. Surh, J., Kwon, H., Estimation of daily exposure to 4-hydroxy-2-alkenals in Korean foods containing n-3 and n-6 polyunsaturated fatty acids, Food Addit. Contam. 2005, 22, 701-708.
24. Fu, M. X., Requena, J. R., Jenkins, A. J., Lyons, T. J., et al., The advanced glycation end product, N-epsilon-(carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions, J. Biol. Chem. 1996, 271, 9982-9986.
25. Morachiello, C., Esteve, E., Regueiro, G., Cholesterol oxidation in meat from chikens fed alpha-tocopherol and beta-carotene supplemented diets with different unsaturation grades, Lipids 1998, 33, 705-713.
26. Osada, K., Hoshina, S., Nakamura, S., Sugano, M., Cholesterol oxidation in meat products and its regulation by supplementation of sodium nitrite and apple polyphenol before processing, J. Agric. Food Chem. 2000, 48, 3823-3829.
27. Staprans, I., Pan, X., Rapp, J., Fiengold, K., Oxidized cholesterol in the diet accelerates the development of aortic atherosclerosis in cholesterol-fed rabbits, Atheroscler. Thromb. Vasc. Biol. 1998, 18, 977-983.
28. Staprans, I., Pan, X., Rapp, J., Fiengold, K., Oxidized cholesterol in the diet is a source of oxidized lipoproteins in human serum, J. Lipid Res. 2003, 44, 705-715.
29. Jacobson, M., Cholesterol oxides in Indian ghee: possible cause of unexplained high risk of atherosclerosis in Indian immigrant populations, Lancet 1987, 19, 656-658.
30. Lemaire-Ewing, S., Prunet, C., Montange, T., Vejux, A., et al., Comparison of the cytotoxic, pro-oxidant and pro-inflammatory characteristics of different oxysterols, Cell Biol. Toxicol. 2005, 21, 97-114.
31. Larsson, A. O., Baird, S., Nyhalah, J., Yuan, X. M., Li, W., Oxysterol mixtures, in atheroma-relevant proportions, display synergistic and proapoptotic effects, Free Radic. Biol. Med. 2006, 41, 902-910.
32. Kanner, J., Lapidot, T., The stomach as a bioreactor: dietary lipid peroxidation in the gastric fluid and the effects of plant-derived antioxidants, Free Radic. Biol. Med. 2001, 37, 1388-1395.
33. Lapidot, T., Granit, R., Kanner, J., Lipid hydroperoxidase activity of myoglobin and phenolic antioxidants in simulated gastric fluid, J. Agric. Food Chem. 2001, 53, 3391-3396.
34. Halliwell, B., Zhao, K., Whiteman, M., The gastrointestinal tract: a major site of antioxidant action?, Free Rad. Res. 2000, 33, 819-830.
35. Gorelik, S., Kohen, R., Ligumsky, M., Kanner, J., Saliva plays a dual role in oxidation process in stomach medium, Arch. Biochem. Biophys. 2007, 458, 236-243.
36. Kamazawa, K., Ashida, H., Dietary hydroperoxides of linoleic acid decompose to aldehydes in stomach before being absorbed into the body, Biochem. Biophys. Acta 1998, 1393, 349-361.
37. Suomela, J., Ahotupa, M., Kallio, H., Triacylglycerol oxidation in pig lipoproteins after a diet rich in oxidized sunflower seed oil, Lipids 2005, 40, 437-444.
38. Hayashi, T., Uchida, K., Takebe, G., Takahashi, K., Rapid formation of 4-hydroxy-2-nonenal, malondialdehyde and phosphatidylcholine aldehyde foam phospholipid hydroproxide by hemoproteins, Free Radic. Biol. Med. 2004, 36, 1025-1033.
39. Piche, L. A., Cole, P. D., Hadley, M., van den Bergh, R., Draper, H., Identification of N-epsilon-(2-propenal)lysine as the main form of malondialdehyde in food digesta, Carcinogenesis 1988, 9, 473-477.
40. Giron-Calle, J., Alaiz, M., Millan, F., Rutz-Gutierrez, V., Vioque, E., Bound malondialdehyde in foods: bioavailability of the N-2-propenals of lysine, J. Agric. Food Chem. 2002, 50, 6194-6198.
41. Flohe-Brigelius, R., Tissue - specific functions of individual glutathione peroxidases, Free Radic. Biol. Med. 1999, 27, 951-965.
42. Loguercio, C., Di-Pierro, M., The role of glutathione in the gastrointestinal tract: a review, Ital. J. Gastroenterol. Hepatol. 1999, 37, 401-407.
43. Loguercio, C., Tarante, D., Beneduce, F., Del Vecchio, B. C., de Vicentiis, A., Nardi, G., Glutathione prevents ethanol induced gastric mucosal damage and depletion of sulfhydryl compounds in humans, Gut 1993, 34, 161-165.
44. Martin, M. J., La-Casa, C., Alarco de la Lastra, C., Cobeza, J. et al., Anti-oxidant mechanisms involved in gastroprotective effects of quercetin, Z. Naturforsch. 1998, 53, 82-88.
45. Akbulut, H., Akbulut, K., Gomel, B., Malondialdehyde and glutathione in rat gastric mucosa and effects of exogenous melatonin, Dig. Dis. Sci. 1997, 42, 1381-1382.
46. Aw, T. Y., Absorption and lymphatic transport of peroxidized lipids by rat small intestine in vivo: role of mucosal GSH, Toxic. Appl. Pharmacol. 2005, 204, 320-328.
47. Bosh-Morell, F., Flohe, L., Marin, N., Romero, F. J., 4-Hydroxynonenal inhibits glutathione peroxidase: protection by glutathione, Free Radic. Biol. Med. 1999, 26, 1383-1387.
48. Aw, T. Y., Williams, M., Gray, L., Absorption and lymphatic transport of peroxidized lipids by rat small intestine in vivo: role of mucosal GSH, Am. J. Physiol. 1992, 262, G99-G106.
49. Nagatsugawa, K., Kaneda, T., Absorption and metabolism of methyllinoleate hydroperoxides in rats, J. Jpn. Oil Chem. Soc. 1983, 52, 362-366.
50. Staprans, I., Rapp, J., Pan, X., Kim, K. Y., Feingold, K. R., Oxidized lipids in the diet are a source of oxidized lipid in chylomicrons of human serum, Arterioscler. Thromb. 1994, 14, 1900-1905.
51. Staprans, I., Hardman, D., Pan, X. H., Feingold, K. R., Effect of oxidized lipids in the diet on oxidized lipid levels in post-prandial serum chylomicrons of diabetic patients, Diabetes Care 1999, 22, 300-306.
52. Ursini, F., Zamburlini, A., Cazzolato, G., Maiorino, M. et al., Postprandial plasma lipid hydroperoxides: a possible link between diet and atherosclerosis, Free Radic. Biol. Med. 1998, 25, 250-252.
53. Draper, H. H., Polensek, L., Hadley, M., McGirr, L. G., Urinary malondialdehyde as an indicator of lipid peroxidation in the diet and in the tissues, Lipids 1984, 19, 836-843.
54. Brown, E. D., Morris, V. C., Rhodes, D. G., Sinha, R. G., Lavender, O. A., Urinary malondialdehyde-equivalents during ingestion of meat cooked at high or low temperatures, Lipids 1995, 50, 1053-1056.
55. Grootveld, M., Atherton, M. D., Sheerin, A. N., Hawkes, J., Blake, D. R., et al., In vivo absorption, metabolism, and urinary excretion of alpha, beta-unsaturated aldehydes in experimental animals. Relevance to the development of cardiovascular diseases by the dietary ingestion of the thermally stressed polyunsaturated - rich culinary oils, J. Clin. Invest. 1998, 101, 1210-1218.
56. Koschinsky, T., He, C. J., Mitsuhashi, T., Bucala, R., et al., Orally absorbed reactive glycation products (glycotoxins): an enviromental risk factor in diabetic nephropathy, Proc. Natl. Acad. Sci. USA 1997, 94, 6474-6479.
57. Vlassara, H., Cai, W., Craudalt, J., Goldberg, T., et al., Inflammatory mediators are induced by dietary glycotoxins, a major risk factor for diabetic angiopathy, Proc. Natl. Acad. Sci. USA 2002, 99, 15596-15601.
58. Monnier, V. M., Intervention against the maillard reaction in vivo, Arch. Biochem. Biophys. 2003, 419, 1-15.
59. Goldberg, T., Cai, W., Peppa, M., Dardaine, V, et al., Advanced glycoxidation end products in commonly consumed foods, J. Am. Diet Assoc. 2004, 104, 1287-1291.
60. Vine, D. F., Mamo, J. C. L., Beilin, L. J., Mori, T. A., Croft, K. D., Dietary oxycholesterols are incorporated in plasma triglyceride-rich lipoproteins, increase their susceptibility to oxidation and increase aortic cholesterol concentration of rabbits, J. Lipid Res. 1998, 39, 1995-2004.
61. Proctor, S. D., Mamo, J. C. L., Retention of fluorescent-labelled chylomicrons reminants within the intima of the arterial wall-evidence that plaque cholesterol may be derived from post-prandial lipoproteins, Eur. J. Clin. Invest. 1998, 28, 497-503.
62. Staprans, I., Pan, X.-M., Rapp, J. H., Feingold, K. R., The role of dietary oxidizes cholesterol and oxidized fatty acids in the development of atherogenesis, Mol. Nutr. Food Res. 2005, 49, 1075-1082.
63. Vivekananthan, D. P., Penn, M. S., Sapp, S. K., Hsu, A., Topol, E. J., Use of antioxidant vitamins for the prevention of cardiovascular disease: meta-analysis of randomised trials, Lancet 2003, 361, 2017-2023.
64. Van Berkel, T. J., De Ryjke, Y. B., Kruijt, J. K., Different fate in vivo of oxidatively modified low density lipoprotein and acetylated low density lipoprotein in rats. Recognition by various scavenger receptors on Kupffer and endothelial liver cells, J. Biol. Chem. 1991, 266, 2282-2289.
65. Boullier, A., Gillote, K. L., Horkko, S., Green, S. R., et al., The binding of oxidized low density lipoprotein to mouse CD36 is mediated in part by oxidized phospholipids that are assciated with both the lipid and protein moieties of the lipo-protein, J. Biol. Chem. 2000, 275, 9163-9169.
66. Palinski, W., Horkko, S., Miller, E., Cloning of monoclonal antoantibodies to epitopes of oxidized lipoproteins from apo-lipoprotein E-deficient mice. Demonstration of epitopes of oxidized low density lipoprotein in human plasma, J. Clin. Invest. 1996, 98, 800-814.
67. Holvoet, P., Collen, D., van de Werf, F., Malondialdehyde - modified LDL as a marker of actute coronary syndromes, JAMA 1999, 281, 1721-1727.
68. Schmidt, A., Yan, S. O., Van, S. F., Stern, D. M., The biology of the receptor for advanced glycation end products and its ligands, Biochim. Biophys. Acta 2000, 1498, 99-111.
69. Slolnik, E., Yang, Z., Makita, Z., Radoft, S., et al., Human and rat mesangial cell receptors for glucose-modified proteins: potential role in kidney tissue remodelling and diabetic nephropathy, J. Exp. Med. 1991, 174, 931-939.
70. Zill, H., Gunther, R., Etbersdobler, H. F., Flosch, U. R., Faist, V, RAGE expression and AGE-induced MAP kinase activation in Caco-2 cells, Biochim. Biophys. Res. Commun. 2001, 288, 1108-1111.
71. Basta, G., Schmidt, A. M., De Caterina, R., Advanced glycation end products and vascular inflammation: implications for accelerated atherosclerosis in diabetes, Cardiovasc. Res. 2004, 65, 583-592.
72. Ross, R., The pathogenesis of atherosclerosis: a perspective for the 1990s, Nature 1993, 362, 801-809.
73. Libby, P., Inflammation in atherosclerosis, Nature 2002, 420, 868-874.
74. Libby, P., Inflammation and cardiovascular disease mechanisms, Am. J. Clin. Nutr. 2006, 83, 456S-460S.
75. Spiteller, G., The relation of lipid peroxidation processes with atherogenesis: A new theory on atherogenesis, Mol. Nutr. Food Res. 2005, 49, 999-1013.
76. Domoto, K., Taniguchi, T., Takaishi, H., Takahashi, T., et al., Chylomicron remnants induce monocyte chemoattractant protein-1 expression via p38 MAPK activation in vascular smooth muscle cells, Atherogenesis 2003, 171, 193-200.
77. Williams, M. J., Sutherland, W. H., McCormick, M. P., deJong, S. A., et al., Impaired endothelial function following a meal rich in used cooking fat, J. Am. Coll. Cardiol. 1999, 33, 1050-1055.
78. Vogel, R., Correntti, M., Plotnick, G., The postprandial effect of components of the mediterranean diet on edothelial function, J. Am. Coll. Cardiol. 2000, 36, 1455-1460.
79. Burdge, G. C., Calder, P. C., Plasma cytokine response during the postprandial period: a potential causal process in vascular disease?, Br. J. Nutr. 2005, 93, 3-9.
80. Uribarri, J., Peppa, M., Cai, W., Goldberg, T., et al., Restriction of dietary of glycotoxins reduces excessive advanced glycation end products in renal failure patients, J. Am. Soc. Nephrol. 2003, 14, 728-731.
81. Nathan, C., Points of control in inflammation, Nature 2002, 420, 846-852.
82. Zilversmit, D., Atherogenesis: a postprandial phenomenon, Circulation 1979, 60, 473-485.
83. Gorelik, S., Ligumsky, M., Kohen, R., Kanner, J., A novel function of red wine polyphenols: Prevention of absorption of cytotoxic lipid peroxidation products, FASEB J., 2007 (in press).