Changes and effects of dietary oxidized lipids in the gastrointestinal tract

Lipid Insights

Volumn 2 1, Issue , 2008, Pages 11-19

  Marquez Ruiz G ^a   Garcia Martinez M C ^a   Holgado, F ^a  

^a INSTITUTO DEL FRÍO CSIC   (Spain)

Author keywords

Dietary oxidized lipids; Gastric conditions; Gastrointestinal tract; Hydroperoxides; Nonabsorbed lipids; Polymers

Indexed keywords

EID: 77956538312     PISSN: None     EISSN: 11786353     Source Type: Journal    
DOI: 10.4137/lpi.s904     Document Type: Review

References (85)

1. Aw, T.Y. 2005. Absorption and lymphatic transport of peroxidized lipids by rat small intestine in vivo: role of mucosal GSH. Toxicol Applied Pharmacol., 204:320-8.
2. Arroyo, R., Sánchez-Muniz, F.J., Cuesta, C. et al. 1996. Hydrolysis of used frying palm olein and sunfl ower oil catalyzed by porcine pancreatic lipase. Lipids, 31:1133-9.
3. Bosh-Morell, F., Flohe, L., Marin, N. et al. 1999. 4-Hydroxynonenal inhibits glutathione peroxidase:protection by glutathione. Free Rad. Biol. Med., 26:1383-7.
4. Brown, A.J. and Jessup, W. 1999. Oxysterols and atherosclerosis. Atherosclerosis, 142:1-28.
5. Bull, A.W. and Bronstein, J.C. 1990. Production of unsaturated carbonyl compounds during metabolism of hydroperoxy fatty acids by colonic homogenates. Carcinogenesis, 11:1699-704.
6. Bull, A.W., Earles, S.M. and Bronstein, J.C. 1991. Metabolism of oxidized linoleic acid: distribution of activity for the enzymatic oxidation of 13-hydroxyoctadecadienoic acid to 13-oxooctadecadienoic acid in rat tissues. Prostaglandins, 41:43-50.
7. Bull, A.W., Nigro, N.D., Golembieski, W.A. et al. 1984. In vivo stimulation of dna synthesis and induction of ornithine decarboxylase in rat colon by fatty acid hydroperoxides, autoxidation products of unsaturated fatty acids. Cancer Res., 44:4924-8.
8. Bull, A.W., Nigro, N.D. and Marnett, L.J. 1988. Structural requirements for stimulation of colonic cell proliferation by oxidized fatty acids. Cancer Res., 48:1771-6.
9. Campbell, S., Stone, W.L., Whaley, S. et al. 2003. Development of gamma (©)-tocopherol as a colorectal cancer chemopreventive agent. Crit. Rev. Onc. Hematol., 47:249-59.
10. Chisolm, G.M. and Steinberg, D. 2000. The oxidative modifi cation hypothesis of atherogenesis: an overview. Free Radic. Biol. Med., 28:1815-26.
11. Cohn, J. 2002. Oxidized fat in the diet, postprandial lipaemia and cardiovascular disease. Curr. Opin. Lipidol., 13:19-24.
12. Chung, F.L., Nath, R.G., Ocando, J. et al. 2000. Deoxyguanosine adducts of t-4-hydroxy-2-nonenal are endogenous DNA lesions in rodents and humans: detection and potential sources. Cancer Res., 1507-11.
13. Diggle, C.P. 2002. In vitro studies on the relationship between polyunsaturated fatty acids and cancer. Tumour or tissue specifi c effects? Prog. Lipid. Res., 41:240-53.
14. Dobarganes, M.C. and Márquez-Ruiz, G. 2003. Oxidized fats in foods. Curr. Opin. Clin. Nutr. Metabol. Care, 6:157-63.
15. Dobarganes, M.C. and Márquez-Ruiz, G. 2006. Formation and analysis of oxidized monomeric, dimeric and higher oligomeric triglycerides. In: Erickson MD, ed. Deep Frying: Chemistry, Nutrition and Practical Applications. Champaign, IL: AOCS Press 87-110.
16. Earles, S.M., Bronstein, J.C., Winner, D.L. et al. 1991. Metabolism of oxidized linoleic acid: characterization of 13-hydroxyoctadecadienoic acid dehydrogenase activity from rat colonic tissue. Biochim. Biophys. Acta., 1081:174-80.
17. Elitsur, Y., Bull, A.W. and Luk, G.D. 1990. Modulation of human colonic lamina propria lymphocite proliferation. Digest Dis. Sci., 35:212-20.
18. Firestone, D. 1996. Regulation of frying fats and oils. Chemistry, Nutrition and Practical Applications. In: Perkins EG, Erickson MD, ed. Deep Frying. Champaign, IL: AOCS Press 323-34.
19. Frankel, E.N. 2005. Lipid Oxidation 2nd ed. Dundee (UK): The Oily Press
20. Gilgun-Sherkin, Y., Melaned, E. and Offen, D. 2003. Antioxidant treatment in Alzheimer's disease - Current state. J. Mol. Neuroscience, 21:1-11.
21. Gilgun-Sherkin, Y., Melaned, E. and Offen, D. 2004. The role of oxidative stress in the pathogenesis of multiple sclerosis: the need for effective antioxidant therapy. J. Neurol., 251:261-8.
22. Giuffrida, F., Destaillats, F., Robert, F. et al. 2004. Formation and hydrolysis of triacylglycerol and sterol epoxides: role of unsaturated triacylglycerol peroxyl radicals. Free Rad. Biol. Med., 37:104-14.
23. González-Muñoz, M.J., Bastida, S. and Sánchez-Muniz, J.F. 2003. Shortterm in vivo digestibility assessment of a highly oxidized and polymerized sunfl ower oil. J. Sci. Food Agric., 83:413-8.
24. Gorelik, S., Lapidot, T., Shaham, I. et al. 2005. Lipid peroxidation and coupled vitamin oxidation in simulated and human gastric fl uid inhibited by dietary polyphenols: health implications. J. Agric. Food Chem., 53:3397-402.
25. Govind Rao, M.K., Risser, N. and Perkins, E.G. 1969. Incorporation of ricinoleic acid into rat lymph lipids. Proc. Soc. Exp. Biol. Med., 131:1369-72.
26. Gualde, N., Chable-Rabinovuitch, H., Motta, C. et al. 1983. Hydroperoxyeicosatetraenoic acids. Potent inhibitors of lymphocyte responses. Biochim. Biophys. Acta., 750:429-33.
27. Guardiola, F., Dutta, P., Codony, R. and Savage, G. 2002. Cholesterol and Phytosterol Oxidation Products: Analysis, Occurrence, and Biological Effects. Champaign, IL: AOCS Press.
28. Hamosh, M. 1984. Lingual lipase. In: Borgstrom B., Brockman HL ed. Lipases., New York: Elsevier 49-80.
29. Hochgraf, E., Mokady, S. and Cogan, E. 1997. Dietary oxidized linoleic acid modifi es lipid composition of rat liver microsomes and increases their fl uidity. J. Nutr., 127:681-6.
30. Hochgraf, E., Mokady, S. and Cogan, E. 2000. Dietary oxidized linoleic acid enhances liver cholesterol biosynthesis and secretion in rats. J. Nutr. Biochem., 11:176-80.
31. Jurek, D., Udilova, N., Jozkowicz, A. et al. 2005. Dietary lipid hydroperoxides induce expression of vascular endothelial growth factor (VEGF) in human colorectal tumor cells. FASEB. J., 19:97-9.
32. Kanazawa, K. and Ashida, H. 1998a. Catabolic fate of dietary trilinoleoylglycerol hydroperoxides in rat gastrointestines. Biochim. Biophys. Acta., 1393:336-48.
33. Kanazawa, K. and Ashida, H. 1998b. Dietary hydroperoxides of linoleic acid decompose to aldehydes in stomach before being absorbed into the body. Biochim. Biophys. Acta., 1393:349-61.
34. Kanazawa, A., Ashida, H., Minamoto, S. et al. 1988. The effects of orally administered linoleic acid and its autoxidation products on intestinal mucosa in rat. J. Nutr. Sci. Vitaminol., 34:363-73.
35. Kanazawa, A., Sawa, T., Akaik, T. et al. 2000. Formation of abasic sites in DNA by t-butyl peroxyl radicals: implication for potent genotoxicity of lipid peroxyl radicals. Cancer Letters, 156:51-5.
36. Kanazawa, A., Sawa, T., Akaik, T. et al. 2002. Dietary lipid peroxidation products and DNA damage in colon carcinogenesis. Eur. J. Lipid. Sci. Technol., 104:439-47.
37. Kanner, J. 2007. Dietary advanced lipid oxidation endproducts are risk factors to human health. Mol. Nutr. Food Res., 51:1094-101.
38. Kanner, J. and Lapidot, T. 2001. The stomach as a bioreactor: dietary lipid peroxidation in the gastric fl uid and the effects of plant-derived antioxidants. Free Radic. Biol. Med., 31:1388-95.
39. Kieckebusch, W., Griem, W., Czok, G. et al. 1963. Nutrition physiological properties of ricinoleic acid methyl ester. Z Ernaehrungswiss, 93:26-34.
40. Kuda, T., Enomoto, T., Yano, T. et al. 2000. Cecal environment and TBARS level in mice fed corn oil, beef tallow and menhaden fi sh oil. J. Nutr. Sci. Vitamin., 46:65-70.
41. Lapidot, T., Granit, R. and Kanner, J. 2005. Lipid peroxidation by " free" iron ions and myoglobin as affected by dietary antioxidants in simulated gastric fl uids. J. Agric. Food Chem., 53:3383-90.
42. Lapidot, T., Granit, R. and Kanner, J. 2005. Lipid hydroperoxidase activity of myoglobin and phenolic antioxidants in simulated gastric fl uid. J. Agric. Food Chem., 53:3391-6.
43. Loguercio, C. and Di Pierro, M. 1999. The role of glutathione in the gastrointestinal tract: a review. Ital. J. Gastroenterol. Hepatol., 31:401-7.
44. Maerker, G., Nungesser, E.H. and Bunick, F. 1988. Reaction of cholesterol 5,6-epoxides with simulated gastric juice. Lipids, 23:761-65.
45. Marnett, L.J. 1999. Lipid peroxidation-DNA damage by malondialdehyde. Mutation Res., 424:83-95.
46. Márquez-Ruiz, G. and Dobarganes, M.C. 1992. Changes in endogenous lipid excretion in rats fed diets containing non-heated and thermally oxidized olive oils. Scand J. Gastroenterol., 27:1069-76.
47. Márquez-Ruiz, G. and Dobarganes, M.C. 1995. Assessments on the digestibility of oxidized compounds from [1-14C]-linoleic acid using a combination of chromatographic techniques. J. Chromatog. B., 675:1-8.
48. Márquez-Ruiz, G. and Dobarganes, M.C. 2006. Nutritional and physiological effects of used frying oils and fats. In: Erickson MD, ed. Deep Frying: Chemistry, Nutrition and Practical Applications. Champaign, IL: American Oil Chemists 'Society' 173-203.
49. Márquez-Ruiz, G., Guevel, G. and Dobarganes, M.C. 1998. Application of chromatographic techniques to evaluate enzymatic hydrolysis of oxidized and polymeric triglycerides by pancreatic lipase " in vitro" J. Am. Oil Chem. Soc., 75:119-26.
50. Márquez-Ruíz, G., Pérez-Camino, M.C. and Dobarganes, M.C. 1993. Evaluation of hydrolysis and absorption of thermally oxidized olive oil in non-absorbed lipids in the rat. Ann. Nutr. Metabol., 37:121-28.
51. Márquez-Ruiz, G., Pérez-Camino, M.C., Ruiz-Gutiérrez, V. et al. 1991. Absorción de grasas termoxidadas. I. Reproducibilidad y exactitud de las técnicas previas a la evaluación de lípidos no absorbidos. Grasas y Aceites, 42:32-7.
52. Márquez-Ruiz, G., Pérez-Camino, M.C. and Dobarganes, M.C. 1992. Digestibility of fatty acid monomers, dimers and polymers in the rat. J. Am. Oil Chem. Soc., 69:930-4.
53. Márquez-Ruiz, G., Pérez-Camino, M.C., Ruiz-Gutiérrez, V. et al. 1992. Absorción de grasas termoxidadas. II. Infl uencia del nivel de alteración y porcentaje de grasa en la dieta. Grasas y Aceites, 431:98-203.
54. Márquez-Ruiz, G., Pérez-Camino, M.C. and Dobarganes, M.C. 1992. In vitro action of pancreatic lipase on complex glycerides from thermally oxidized oils. Fat. Sci. Technol., 94:307-12.
55. Muller, C., Friedrichs, R., Wingler, K. et al. 2002. Perturbation of lipid metabolism by linoleic acid hydroperoxide in caco-2 cells. Biol. Chem., 383:637-48.
56. Nagatsugawa, K. and Kaneda, T. 1983. Absorption and metabolism of methyl linoleate hydroperoxides in rats. J. Jpn. Oil Chem. Soc., 32:362-66.
57. Penumetcha, M., Khan-Merchant, N. and Parthasarathy, S. 2000. Dietary oxidized fatty acids: an atherogenic risk? J. Lipid Res., 41:1473-80.
58. Penumetcha, M., Khan-Merchant, N. and Parthasarathy, S. 2002. Enhanced solubilization and intestinal absorption of cholesterol by oxidized linoleic acid. J. Lipid Res., 43:895-903.
59. Perkins, E.G., Endres, J.G. and Kummerow, F.A. 1961. The Metabolism of Fats I. Effect of dietary hydroxy acids and their triglycerides on growth, carcass, and fecal fat composition in the rat. J. Nutr., 73:291-8.
60. Piazza, G.J., Nunez, A. and Foglia, T.A. 2003. Isolation of unsaturated diols after oxidation of conjugated linoleic acid with peroxygenase. Lipids, 38:255-65.
61. Reber, R.J. and Draper, H.H. 1970. Absorption and metabolism of 1-14Chydroxy octadecadienoate in the rat. Lipids, 5:983-7.
62. Rong, R., Ramachandran, S., Penumetcha, M. et al. 2002. Dietary oxidized fatty acids may enhance intestinal apolipoprotein A-I production. J. Lipid Res., 43:557-64.
63. Saguy, I.S. and Dana, D. 2003. Integrated approach to deep fat frying: engineering, nutrition, health and consumer aspects. J. Food Eng., 56:143-52.
64. Sánchez-Muniz, F.J., Arroyo, R., Sánchez-Montero, J.M. et al. 2000. In vitro digestibility study of thermal oxidised palm oleins. Food Sci. Technol. Int., 6:449-56.
65. Sánchez-Muniz, F.J., Bastida, S. and Gónzalez-Muñoz, M.J. 1999. Column and high-performance size exclusion chromatography applications to the in vivo digestibility study of a thermoxidized and polymerized olive oil. Lipids, 34:1187-92.
66. Sánchez-Muniz, F.J., Bastida, S., Márquez-Ruiz, G. et al. 2007. Effect of heating and frying on oil and food fatty acids. In: Chow, CK, ed. Fatty Acids in Foods and Their Health Implications. Boca Raton, FL: CRC Press. 511-43.
67. Sawa, T., Akaike, T., Kida, K. et al. 1998. Lipid peroxyl radicals from oxidized oils and heme-iron: Implication of a high fat diet in colon carcinogenesis. Cancer Epidemiol. Biomarkers Prev., 7:1007-12.
68. Spiteller, G. 2006. Peroxyl radicals:Induction of neurodegenerative and other infl ammatory diseases. Their origin and how they transform cholesterol, phospholipids, plasmalogens, polyunsaturated fatty acids, sugars and proteins into deleterious products. Free Rad. Biol. Med., 41:362-87.
69. Staprans, I., Rapp, J., Pan, X.H. et al. 1994. Oxidized lipids in the diet are a source of oxidized lipids in chylomicrons of human serum. Arterioscler. Thromb., 14:1900-5.
70. Staprans, I., Hardman, D., Pan, X.H. et al. 1999. Effect of oxidized lipids in the diet on oxidized lipid levels in postprancial serum chylomicrons of diabetic patients. Diabetes Care, 22:300-6.
71. Staprans, I., Pan, X.M., Rapp, J.H. et al. 2000. Oxidized cholesterol in the diet accelerates the development of atherosclerosis in LDL receptorand apolipoprotein E-defi cient mice. Arterioscler Thromb. Vasc. Biol., 20:708-14.
72. Stone, W.L. and Papas, A.M. 1997. Tocopherols and the etiology of colon cancer. J. Nat. Cancer Institute, 89:1006-14.
73. Suomela, J.P., Ahotupa, M. and Kallio, H. 2005. Triacylglycerol hydroperoxides not detected in pig small intestinal epithelial cells after a diet rich in oxidized triacylglycerols. Lipids, 40:349-53.
74. Suomela, J.P., Ahotupa, M., Sjovall, O. et al. 2004. Diet and lipoprotein oxidation: Analysis of oxidized triacylglycerols in pig lipoproteins. Lipids, 39:639-47.
75. Terao, J., Nagao, A., Yuki, H. et al. 1993. Reduction of fatty acid hydroperoxides by human parotid saliva. Lipids, 28:121-4.
76. Terao, J. and Fukino, N. 1993. Decomposition of phospholipid hydroperoxides in simulated gastric juice. J. Food Lipids, 1:79-86.
77. Tsunada, S., Iwakiri, R., Fujimoto, K. et al. 2003. Chronic lipid hydroperoxide stress suppresses mucosal proliferation in rat intestine: potentiation of ornithine decarboxylase activity by epidermal growth factor. Digest Dis. Sci., 48:2333-41.
78. Tsunada, S., Iwakiri, R., Noda, T. et al. 2003. Chronic exposure to subtoxic levels of peroxidized lipids suppresses mucosal cell turnover in rat small intestine and reversal by glutathione. Digest Dis. Sci., 48:210-22.
79. Ursini, F., Zamburlini, A., Cazzolato, G. et al. 1998. Posprandial plasma lipid hydroperoxides: a possible link between diet and atherosclerosis. Free Radic. Biol. Med., 25:250-2.
80. Velasco, J., Marmesat, S., Berdeaux, O. et al. 2004. Formation and evolution of monoepoxy fatty acids in thermoxidized olive and sunfl ower oils and quantitation in used frying oils from restaurants and fried food outlets. J. Agric. Food Chem., 52:4438-43.
81. Velasco, J., Marmesat, S., Márquez-Ruiz, G. et al. 2004. Formation of short-chain fatty acids and oxidized monomeric triglycerides during deep-frying and occurrence in used frying fats. Eur. J. Lipid Sci. Technol., 106:728-35.
82. Vonk, R.J., Kalivianakis, M., Minich, D.M. et al. 1997. The metabolic importance of unabsorbed dietary lipids in the colon. Scand J. Gastroenterol., 32:65-7.
83. Wang, T.G., Gotoh, Y., Jennings, M.H. et al. 2000. Lipid hydroperoxideinduced apoptosis in human colonic CaCo-2 cells is associated with an early loss of cellular redox balance. FASEB. J., 14:1567-76.
84. Wilson, R., Lyall, K., Smyth, L. et al. 2002a. Dietary hydroxy fatty acids are absorbed in humans: implications for the measurement of " oxidative stress" in vivo. Free Rad. Biol. Med., 32:162-8.
85. Wilson, R., Fernie, C.E., Scrimgeour, C.M. et al. 2002b. Dietary epoxy fatty acids are absorbed in healthy women. Eur. J. Clin. Invest, 32:79-83.