Chemical modeling of heme-induced lipid oxidation in gastric conditions and inhibition by dietary polyphenols

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 1, 2010, Pages 676-683

  Lorrain, Bénédicte ^a   Dangles, Olivier ^a   Genot, Claude ^b   Dufour, Claire ^a,c  

^a UNIVERSITY OF AVIGNON   (France)

^b INRA   (France)

^c UMR A 408 INRA University of Avignon   (France)

Author keywords

Antioxidant; Gastric tract; Lipid oxidation; Metmyoglobin; Oil in water emulsion; Polyphenol

Indexed keywords

BOVINE SERUM ALBUMIN; FLAVONOID; LIPID; METMYOGLOBIN; PHENOL DERIVATIVE; PHOSPHOLIPID; POLYPHENOLS;

ANIMAL; ARTICLE; BIOLOGICAL MODEL; CATTLE; CHEMICAL MODEL; CHEMISTRY; CHICKEN; LIPID METABOLISM; METABOLISM; OXIDATION REDUCTION REACTION; STOMACH;

ANIMALS; CATTLE; CHICKENS; FLAVONOIDS; LIPID METABOLISM; LIPIDS; METMYOGLOBIN; MODELS, BIOLOGICAL; MODELS, CHEMICAL; OXIDATION-REDUCTION; PHENOLS; PHOSPHOLIPIDS; SERUM ALBUMIN, BOVINE; STOMACH;

BOVINAE;

EID: 75249097116     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf903054e     Document Type: Article

References (37)

1. (1) Hung, H. C.; Joshipura, K. J.; Jiang, R.; Hu, F. B.; Hunter, D.; Smith-Warner, S. A.; Colditz, G. A.; Rosner, B.; Spiegelman, D.; Willett, W. C. Fruit and vegetable intake and risk of major chronic disease J. Natl. Cancer Inst. 2004, 96, 1577-1584. (Pubitemid 39534881)
2. Arts, I. C. W.; Hollman, P. C. H. Polyphenols and disease risk in epidemiologic studies, Am. J. Clin. Nutr. 2005, 57, 317S-325S.
3. Manach, C.; Scalbert, A.; Morand, C.; Remesy, C.; Jimenez, L. Polyphenols: food sources and bioavailability, J. Am. J. Clin. Nutr. 2004, 79, 727-747.
4. Day, A. J.; Bao, Y.; Morgan, M. R. A.; Williamson, G. Conjugation position of quercetin glucuronides and effect on biological activity. Free Radical Biol. Med. 2000, 29, 1234-1243.
5. (5) Halliwell, B.; Zhao, K. C.; Whiteman, M. The gastrointestinal tract: A major site of antioxidant action? Free Radical Res. 2000, 33, 819-830. (Pubitemid 32208490)
6. (6) Armand, M.; Borel, P.; Dubois, C.; Senft, M.; Peyrot, J.; Salducci, J.; Lafont, H.; Lairon, D. Characterization of emulsions and lipolysis of dietary lipids in the human stomach. Am J. Physiol. 1994, 266, G372-G381. (Pubitemid 24115911)
7. (7) Kanner, J.; Lapidot, T. The stomach as a bioreactor: dietary lipid peroxidation in the gastric fluid and the effects of plant-derived antioxidants. Free Radical Biol. Med. 2001, 31, 1388-1395. (Pubitemid 33145308)
8. (8) Kanazawa, K.; Ashida, H. Dietary hydroperoxides of linoleic acid decompose to aldehydes in stomach before being absorbed into the body. Biochim. Biophys. Acta 1998, 1393, 349-361. (Pubitemid 28467060)
9. (9) Kanner, J. Dietary advanced lipid oxidation end-products are risk factors to human health. Mol. Nutr. Food Res. 2007, 51, 1094-1101. (Pubitemid 47522801)
10. (10) Uchida, K. Role of reactive aldehydes in cardiovascular diseases. Free Radical Biol. Med. 2000, 28, 1685-1696. (Pubitemid 30628655)
11. Staprans, I.; Rapp, J. H.; Pan, X.; Feingold, K. R. Oxidized lipids in the diet are incorporated by the liver into very low density lipoprotein in. rats, J. Lipid Res. 1996, 37, 420-430.
12. Ursini, F.; Sevanian, A. Postprandial oxidative stress. Biol. Chem. 2002, 383, 599-605.
13. (13) Gorelik, S.; Lapidot, T.; Shaham, I.; Granit, R.; Ligumsky, M.; Kohen, R.; Kanner, J. Lipid peroxidation and coupled vitamin oxidation in simulated and human gastric fluid inhibited by dietary polyphenols: health implications. J. Agric. Food Chem.. 2005, 55, 3397-3402. (Pubitemid 40758173)
14. Goupy, P.; Vulcain, E.; Caris-Veyrat, C. Dangles, O. Dietary antioxidants as inhibitors of the heme-induced peroxidation of linoleic acid: Mechanism, of action and synergism, Free Radical Biol. Med. 2007, 43, 933-946.
15. Vulcain, E.; Goupy, P.; Caris-Veyrat, C. Dangles, O. Inhibition of the metmyoglobin-induced peroxidation of linoleic acid by dietary antioxidants: action in the aqueous vs. lipid phase. Free Radical. Res. 2005, 39, 547-563.
16. (16) Jungbluth, G.; Ruhling, I.; Ternes, W. Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media. J. Chem. Soc., Perkin Trans. 2000, 2, 1946-1952. (Pubitemid 35165790)
17. (17) Villiere, A.; Viau, M.; Bronnec, I.; Moreau, N.; Genot, C. Oxidative stability of bovine serum albumin- and sodium caseinate-stabilized emulsions depends on metal availability. J. Agric Food Chem. 2005, 55, 1514-1520. (Pubitemid 40322145)
18. Mikkelsen, A.; Skibsted, L. H. Acid-catalysed reduction of ferrylmyoglobin: product distribution, and kinetics of autoreduction and reduction by NADH. Z. Lebensm.-Unters. Forsch. 1995, 200, 171-177.
19. (19) Pryor, W. A.; Castle, L. Chemical Methods for the Detection of Lipid Hydroperoxydes. In Oxygen Radicals in Biological Systems; Packer, L., Ed.; Academic Press: Orlando, FL, 1984; pp 293-295. (Pubitemid 14165389)
20. Rampon, V.; Lethuaut, L.; Mouhous-Riou, N.; Genot, C. Interface characterization and aging of bovine serum, albumin stabilized oil-inwater emulsions as revealed by front-surface fluorescence. J. Agric. Food Chem. 2001, 49, 4046-4051.
21. (21) Dufour, C.; Dangles, O. Flavonoid-serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy. BioChim. Biophys. Acta 2005, 1721, 164-173. (Pubitemid 40093524)
22. Tyssandier, V.; Reboul, E.; Dumas, J. F.; Bouteloup-Demange, C.; Armand, M.; Marcand, J.; Sallas, M.; Borel, P. Processing of vegetable-borne carotenoids in the human stomach and duodenum. Am. J. Physiol. 2003, 284, G913-G923.
23. (23) Dosi, R.; Maro, A. D.; Chambery, A.; Colonna, G.; Costantini, S.; Geraci, G.; Parente, A. Characterization and kinetics studies of water buffalo (Bubalus bubalis) myoglobin. Comp. Biochem. Physiol., Part B: Biochem. Mol. Biol. 2006, 145, 230-238. (Pubitemid 44428213)
24. Baron, C. P.; Andersen, H. J. Myoglobin-induced lipid oxidation; a review. J. Agric. Food Chem. 2002, 50, 3887-3897.
25. Genot, C.; Meynier, A.; Riaublanc, A. Lipid Oxidation in Emulsions. In Lipid Oxidation Pathways; Kamal-Eldin, A. Ed.; AOCS Press: Champaign, IL, 2003; pp 190-234.
26. Kong, L. G.; Beattie, J. K.; Hunter, R. J. Electroacoustic study of BSA or lecithin stabilised soybean oil-in-water emulsions and SDS effect. Colloids Surf, B 2003, 27, 11-21.
27. Pathirana, S.; Neely, W. C.; Vodyanoy, V. Condensing and expanding effects of the odorants (+)-and (-)-carvone on phospholipid monolayers. Langmuir 1998, 14, 679-682.
28. (28) Keszler, A.; Kriska, T.; Nemeth, A. Mechanism of volatile compound production during storage of sunflower oil. J. Agric. Food Qfm. 2000, 48, 5981-5985. (Pubitemid 32056837)
29. (29) Refsgaard, H. H. F.; Tsai, L.; Stadtman, E. R. Modifications of proteins by polyunsaturated fatty acid peroxidation products. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 611-616. (Pubitemid 30070357)
30. Clifford, M.; Brown, J. E. Dietary Flavonoids and Health: Broadening the Perspective. In Flavonoids: Chemistry, Biochemistry and Applications; Andersen, O., Markham, K., Eds; CRC Press: Boca Raton, FL, 2006; pp 319-370.
31. Dufour, C.; Loonis, M. Flavonoids and their oxidation products protect efficiently albumin-bound linoleic acid in a model of plasma oxidation. Biochim. Biophys. Acta 2007, 1770, 958-965.
32. Krishnamachari, V.; Levine, L. H.; Zhou, C.; Pare, P. W. In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern. Chem. Res. Toxicol. 2004, 17, 795-804.
33. (33) Dangles, O.; Fargeix, G.; Dufour, C. Antioxidant properties of anthocyanins and tannins: a mechanistic investigation with catechin and the 3′,4′,7-trihydroxyflavylium ion. J. Chem. Soc., Perkin Trans. 2000, 2, 1653-1663. (Pubitemid 35165800)
34. (34) Roche, M.; Dufour, C.; Mora, N.; Dangles, O. Antioxidant activity of olive phenols: mechanistic investigation and characterization of oxidation products by mass spectrometry. Org. Biomol. Chem. 2005, 3, 423-430. (Pubitemid 40285707)
35. (35) Adzet, T.; Camarasa, J.; Escubedo, E.; Merlos, M. In vitro study of caffeic acid - BSA interaction. Eur. J. Drug Metab. Pharm. 1988, 13, 11-14. (Pubitemid 18132823)
36. Prigent, S. V. E.; Gruppen, H.; Visser, A.; van Koningsveld, G. A.; de Jong, G. A. H.; Voragen, A. G. J. Effects of non-covalent interactions with 5-O-caffeoylquinic acid (chlorogenic acid) on the heat denaturation and solubility of globular proteins. J. Agric Food Chem. 2003, 51, 5088-5095.
37. (37) Rawel, H. A.; Meidtner, K.; Kroll, J. Binding of selected phenolic compounds to proteins. J. Agric. Food Chem. 2005, 53, 4228-4235. (Pubitemid 40936789)