A novel function of red wine polyphenols in humans: Prevention of absorption of cytotoxic lipid peroxidation products

FASEB Journal

Volumn 22, Issue 1, 2008, Pages 41-46

  Gorelik, Shlomit ^a   Ligumsky, Moshe ^b   Kohen, Ron ^a   Kanner, Joseph ^c  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b HADASSAH HEBREW UNIVERSITY MEDICAL CENTER   (Israel)

^c VOLCANI CENTER   (Israel)

Author keywords

Antioxidants; Human plasma; Malondialdehyde; Red muscle

Indexed keywords

MALONALDEHYDE; POLYPHENOL DERIVATIVE; FLAVONOID; PHENOL DERIVATIVE; POLYPHENOLS; UNCLASSIFIED DRUG;

ADULT; ARTICLE; BLOOD ANALYSIS; CARDIOVASCULAR DISEASE; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CROSSOVER PROCEDURE; CYTOTOXICITY; DIET; FEMALE; HUMAN; LIPID ABSORPTION; LIPID PEROXIDATION; MALE; PRIORITY JOURNAL; RED WINE; URINALYSIS; BLOOD; DRUG EFFECT; RANDOMIZED CONTROLLED TRIAL; WINE;

CROSS-OVER STUDIES; FEMALE; FLAVONOIDS; HUMANS; LIPID PEROXIDATION; MALE; MALONDIALDEHYDE; PHENOLS; WINE;

EID: 38049144598     PISSN: 08926638     EISSN: None     Source Type: Journal    
DOI: 10.1096/fj.07-9041com     Document Type: Article

References (51)

1. Lotito, S. B., and Frei, B. (2006) Consumption of flavonoid-rich foods and increased plasma antioxidant capacity in humans: cause, consequence, or epiphenomenon? Free Radic. Biol. Med. 41, 1727-1746
2. Kuhnau, J. (1976) The flavonoids. A class of semi-essential food components: their role in human nutrition. World Rev. Nutr. Diet 24, 117-191
3. Bors, W., and Saran, M. (1987) Radical scavenging by flavonoid antioxidants. Free Radic. Res. Commun. 2, 289-294
4. Aviram, M., Dornfeld, L., Kaplan, M., Coleman, R., Gaitini, D., Nitecki, S., Hofman, A., Rosenblat, M., Volkova, N., Presser, D., et al. (2002) Pomegranate juice flavonoids inhibit low-density lipoprotein oxidation and cardiovascular diseases: studies in atherosclerotic mice and in humans. Drugs Exp. Clin. Res. 28, 49-62
5. Cuevas, A. M., Guasch, V., Castillo, O., Irribarra, V., Mizon, C., San Martin, A., Strobel, P., Perez, D., Germain, A. M., and Leighton, F. (2000) A high-fat diet induces and red wine counteracts endothelial dysfunction in human volunteers. Lipids 35, 143-148
6. Carlsen, H., Myhrstad, M. C., Thoresen, M., Moskaug, J. O., and Blomhoff, R. (2003) Berry intake increases the activity of the gamma-glutamylcysteine synthetase promoter in transgenic reporter mice. J. Nutr. 133, 2137-2140
7. Baur, J. A., Pearson, K. J., Price, N. L., Jamieson, H. A., Lerin, C., Kalra, A., Prabhu, V. V., Allard, J. S., Lopez-Lluch, G., Lewis, K., et al. (2006) Resveratrol improves health and survival of mice on a high-calorie diet. Nature 444, 337-342
8. Manach, C., Williamson, G., Morand, C., Scalbert, A., and Remesy, C. (2005) Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 81, 230S-242S
9. Hu, F. B., and Willett, W. C. (2002) Optimal diets for prevention of coronary heart disease. J. Am. Med. Assoc. 288, 2569-2578
10. Ross, R. (1993) The pathogenesis of atherosclerosis: a perspective for the 1990s. Nature 362, 801-809
11. Steinberg, D., Parthasarathy, S., Carew, T. E., Khoo, J. C., and Witztum, J. L. (1989) Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320, 915-924
12. Ursini, F., Zamburlini, A., Cazzolato, G., Maiorino, M., Bon, G. B., and Sevanian, A. (1998) Postprandial plasma lipid hydroperoxides: a possible link between diet and atherosclerosis. Free Radic. Biol. Med. 25, 250-252
13. Cohn, J. S. (2002) Oxidized fat in the diet, postprandial lipaemia and cardiovascular disease. Curr. Opin. Lipidol. 13, 19-24
14. Sies, H., Stahl, W., and Sevanian, A. (2005) Nutritional, dietary and postprandial oxidative stress. J. Nutr. 135, 969-972
15. Staprans, I., Hardman, D. A., Pan, X. M., and Feingold, K. R. (1999) Effect of oxidized lipids in the diet on oxidized lipid levels in postprandial serum chylomicrons of diabetic patients. Diabetes Care 22, 300-306
16. Williams, M. J., Sutherland, W. H., McCormick, M. P., de Jong, S. A., Walker, R. J., and Wilkins, G. T. (1999) Impaired endothelial function following a meal rich in used cooking fat. J. Am. Coll. Cardiol. 33, 1050-1055
17. Kanner, J., and Lapidot, T. (2001) The stomach as a bioreactor: dietary lipid peroxidation in the gastric fluid and the effects of plant-derived antioxidants. Free Radic. Biol. Med. 31, 1388-1395
18. Kubow, S. (1992) Routes of formation and toxic consequences of lipid oxidation products in foods. Free Radic. Biol. Med. 12, 63-81
19. Halliwell, B., Zhao, K., and Whiteman, M. (2000) The gastrointestinal tract: a major site of antioxidant action? Free Radic. Res. 33, 819-830
20. Brown, E. D., Morris, V. C., Rhodes, D. G., Sinha, R., and Levander, O. A. (1995) Urinary malondialdehyde-equivalents during ingestion of meat cooked at high or low temperatures. Lipids 30, 1053-1056
21. Staprans, I., Pan, X. M., Rapp, J. H., and Feingold, K. R. (2003) Oxidized cholesterol in the diet is a source of oxidized lipoproteins in human serum. J. Lipid Res. 44, 705-715
22. Norat, T., and Riboli, E. (2001) Meat consumption and colorectal cancer: a review of epidemiologic evidence. Nutr. Rev. 59, 37-47
23. Kanner, J., and Harel, S. (1985) Initiation of membranal lipid peroxidation by activated metmyoglobin and methemoglobin. Arch. Biochem. Biophys. 237, 314-321
24. Stocker, R., and Keaney, J. F., Jr. (2005) New insights on oxidative stress in the artery wall. J. Thromb. Haemost. 3, 1825-1834
25. Kanner, J. (1994) Oxidative processes in meat and meat products: quality implications. Meat Sci. 36, 169-189
26. Kadiiska, M. B., Gladen, B. C., Baird, D. D., Germolec, D., Graham, L. B., Parker, C. E., Nyska, A., Wachsman, J. T., Ames, B. N., Basu, S., et al. (2005) Biomarkers of oxidative stress study II: are oxidation products of lipids, proteins, and DNA markers of CCl4 poisoning? Free Radic. Biol. Med. 38, 698-710
27. Hadley, M., and Draper, H. H. (1989) Identification of N-(2-propenal)ethanolamine as a urinary metabolite of malondialdehyde. Free Radic. Biol. Med. 6, 49-52
28. Suomela, J. P., Ahotupa, M., and Kallio, H. (2005) Triacylglycerol oxidation in pig lipoproteins after a diet rich in oxidized sunflower seed oil. Lipids 40, 437-444
29. Vlassara, H., Cai, W., Crandall, J., Goldberg, T., Oberstein, R., Dardaine, V., Peppa, M., and Rayfield, E. J. (2002) Inflammatory mediators are induced by dietary glycotoxins, a major risk factor for diabetic angiopathy. Proc. Natl. Acad. Sci. U. S. A. 99, 15596-15601
30. Goldberg, T., Cai, W., Peppa, M., Dardaine, V., Baliga, B. S., Uribarri, J., and Vlassara, H. (2004) Advanced glycoxidation end products in commonly consumed foods. J. Am. Diet Assoc. 104, 1287-1291
31. Uchida, K. (2000) Role of reactive aldehyde in cardiovascular diseases. Free Radic. Biol. Med. 28, 1685-1696
32. Aldini, G., Dalle-Donne, I., Facino, R. M., Milzani, A., and Carini, M. (2006) Intervention strategies to inhibit protein carbonylation by lipoxidation-derived reactive carbonyls. Med. Res. Rev. In press
33. Palinski, W., Rosenfeld, M. E., Yla-Herttuala, S., Gurtner, G. C., Socher, S. S., Butler, S. W., Parthasarathy, S., Carew, T. E., Steinberg, D., and Witztum, J. L. (1989) Low density lipoprotein undergoes oxidative modification in vivo. Proc. Natl. Acad. Sci. U. S. A. 86, 1372-1376
34. Holvoet, P., Perez, G., Zhao, Z., Brouwers, E., Bernar, H., and Collen, D. (1995) Malondialdehyde-modified low density lipoproteins in patients with atherosclerotic disease. J. Clin. Invest. 95, 2611-2619
35. Niedernhofer, L. J., Daniels, J. S., Rouzer, C. A., Greene, R. E., and Marnett, L. J. (2003) Malondialdehyde, a product of lipid peroxidation, is mutagenic in human cells. J. Biol. Chem. 278, 31426-31433
36. Feng, Z., Hu, W., Marnett, L. J., and Tang, M. S. (2006) Malondialdehyde, a major endogenous lipid peroxidation product, sensitizes human cells to UV- and BPDE-induced killing and mutagenesis through inhibition of nucleotide excision repair. Mutat. Res. 601, 125-136
37. Ichinose, T., Nobuyuki, S., Takano, H., Abe, M., Sadakane, K., Yanagisawa, R., Ochi, H., Fujioka, K., Lee, K. G., and Shibamoto, T. (2004) Liver carcinogenesis and formation of 8-hydroxydeoxyguanosine in C3H/HeN mice by oxidized dietary oils containing carcinogenic dicarbonyl compounds. Food Chem. Toxicol. 42, 1795-1803
38. West, J. D., and Marnett, L. J. (2006) Endogenous reactive intermediates as modulators of cell signaling and cell death. Chem. Res. Toxicol. 19, 173-194
39. Zhang, Q., Powers, E. T., Nieva, J., Huff, M. E., Dendle, M. A., Bieschke, J., Glabe, C. G., Eschenmoser, A., Wentworth, P., Jr., Lerner, R. A., and Kelly, J. W. (2004) Metabolite-initiated protein misfolding may trigger Alzheimer's disease. Proc. Natl. Acad. Sci. U. S. A. 101, 4752-4757
40. Plastaras, J. P., Riggins, J. N., Otteneder, M., and Marnett, L. J. (2000) Reactivity and mutagenicity of endogenous DNA oxopropenylating agents: base propenals, malondialdehyde, and N(epsilon)-oxopropenyllysine. Chem. Res. Toxicol. 13, 1235-1242
41. Gopaul, N. K., Halliwell, B., and Anggard, E. E. (2000) Measurement of plasma F2-isoprostanes as an index of lipid peroxidation does not appear to be confounded by diet. Free Radic. Res. 33, 115-127
42. Giron-Calle, J., Alaiz, M., Millan, F., Ruiz-Gutierrez, V., and Vioque, E. (2002) Bound malondialdehyde in foods: bioavailability of the N-2-propenals of lysine. J. Agric. Food Chem. 50, 6194-6198
43. Gorelik, S., Kohen, R., Ligumsky, M., and Kanner, J. (2007) Saliva plays a dual role in oxidation process in stomach medium. Arch. Biochem. Biophys. 458, 236-243
44. Gorelik, S., Lapidot, T., Shaham, I., Granit, R., Ligumsky, M., Kohen, R., and Kanner, J. (2005) Lipid peroxidation and coupled vitamin oxidation in simulated and human gastric fluid inhibited by dietary polyphenols: health implications. J. Agric. Food Chem. 53, 3397-3402
45. Lo, C. Y., Li, S., Tan, D., Pan, M. H., Sang, S., and Ho, C. T. (2006) Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions. Mol. Nutr. Food Res. 50, 1118-1128
46. Totlani, V. M., and Peterson, D. G. (2006) Epicatechin carbonyl-trapping reactions in aqueous maillard systems: identification and structural elucidation. J. Agric. Food Chem. 54, 7311-7318
47. Piche, L. A., Cole, P. D., Hadley, M., van den Bergh, R., and Draper, H. H. (1988) Identification of N-epsilon-(2-propenal)lysine as the main form of malondialdehyde in food digesta. Carcinogenesis 9, 473-477
48. Gee, J. M., DuPont, M. S., Rhodes, M. J., and Johnson, I. T. (1998) Quercetin glucosides interact with the intestinal glucose transport pathway. Free Radic. Biol. Med. 25, 19-25
49. McDougall, G. J., and Stewart, D. (2005) The inhibitory effects of berry polyphenols on digestive enzymes. Biofactors 23, 189-195
50. Kandra, L., Gyemant, G., Zajacz, A., and Batta, G. (2004) Inhibitory effects of tannin on human salivary alpha-amylase. Biochem. Biophys. Res. Commun. 319, 1265-1271
51. Kanner, J. (2007) Dietary advanced lipid oxidation end products are risk factors to human health. (Review) Mol. Nutr. Food Res. In press.