LDL isolated from plasma-loaded red wine procyanidins resist lipid oxidation and tocopherol depletion

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 10, 2008, Pages 3798-3804

  Lourenço, Cátia F ^a   Gago, Bruno ^a   Barbosa, Rui M ^a   De Freitas, Víctor ^b   Laranjinha, João ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF PORTO   (Portugal)

Author keywords

tocopherol recycling; LDL oxidation; Procyanidins; Wine

Indexed keywords

ALPHA TOCOPHEROL; FREE RADICAL; LOW DENSITY LIPOPROTEIN; PROANTHOCYANIDIN;

ARTICLE; BLOOD; CHEMISTRY; DRUG EFFECT; HUMAN; LIPID PEROXIDATION; WINE;

ALPHA-TOCOPHEROL; FREE RADICALS; HUMANS; LIPID PEROXIDATION; LIPOPROTEINS, LDL; PROANTHOCYANIDINS; WINE;

EID: 45549089760     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0733259     Document Type: Article

References (38)

1. Witztum, J. L.; Steinberg, D. The oxidative modification hypothesis of atherosclerosis: does it hold for humans. Trends Cardiovasc. Med. 2001, 11, 93-102.
2. Aviram, M.; Fuhrman, B. Wine flavonoids protect against LDL oxidation and atherosclerosis. Ann. N.Y. Acad. Sci. 2002, 957, 146-61.
3. Berliner, J. A.; Heinecke, J. W. The role of oxidized lipoproteins in atherogenesis. Free Radical Biol. Med. 1996, 20, 707-27.
4. Bors, W.; Heller, W.; Michel, C.; Saran, M. Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods Enzymol. 1990, 186, 343-55.
5. Simonetti, P.; Gardana, C.; Pietta, P. Caffeic acid as biomarker of red wine intake. Methods Enzymol. 2001, 335, 122-30.
6. Walle, T. Absorption and metabolism of flavonoids. Free Radical Biol. Med. 2004, 36, 829-37.
7. Rice-Evans, C. Flavonoids and isoflavones: absorption, metabolism, and bioactivity. Free Radical Biol. Med. 2004, 36, 827-8.
8. De Azevedo, W. F., Jr.; Mueller-Dieckmann, H. J.; Schulze-Gahmen, U.; Worland, P. J.; Sausville, E.; Kim, S. H. Structural basis for specificity and potency of a flavonoid inhibitor of human CDK2, a cell cycle kinase. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 2735-40.
9. Williams, R. J.; Spencer, J. P.; Rice-Evans, C. Flavonoids: antioxidants or signalling molecules. Free Radical Biol. Med. 2004, 36, 838-49.
10. Corder, R.; Mullen, W.; Khan, N. Q.; Marks, S. C.; Wood, E. G.; Carrier, M. J.; Crozier, A. Oenology: red wine procyanidins and vascular health. Nature 2006, 444, 566.
11. Rahman, I.; Biswas, S. K.; Kirkham, P. A. Regulation of inflammation and redox signaling by dietary polyphenols. Biochem. Pharmacol. 2006, 72, 1439-52.
12. Steffen, Y.; Schewe, T.; Sies, H. (-)-Epicatechin elevates nitric oxide in endothelial cells via inhibition of NADPH oxidase. Biochem. Biophys. Res. Commun. 2007, 359, 828-33.
13. Laranjinha, J.; Cadenas, E. Redox cycles of caffeic acid, alphatocopherol, and ascorbate: implications for protection of low-density lipoproteins against oxidation. IUBMB Life 1999, 48, 57-65.
14. Laranjinha, J.; Vieira, O.; Madeira, V.; Almeida, L. Two related phenolic antioxidants with opposite effects on vitamin E content in low density lipoproteins oxidized by ferrylmyoglobin: consumption vs regeneration. Arch. Biochem. Biophys. 1995, 323, 373-81.
15. Terao, J.; Piskula, M. K. Flavonoids and membrane lipid peroxidation inhibition. Nutrition 1999, 15, 790-1.
16. Fraga, C. G. Plant polyphenols: how to translate their in vitro antioxidant actions to in vivo conditions. IUBMB Life 2007, 59, 308-15.
17. Stocker, R.; Keaney, J. F., Jr. Role of oxidative modifications in atherosclerosis. Physiol Rev 2004, 84, 1381-478.
18. Waterhouse, A. L. Wine phenolics. Ann. N.Y. Acad. Sci. 2002, 957, 21-36.
19. Nigdikar, S. V.; Williams, N. R.; Griffin, B. A.; Howard, A. N. Consumption of red wine polyphenols reduces the susceptibility of low-density lipoproteins to oxidation in vivo. Am. J. Clin. Nutr. 1998, 68, 258-65.
20. Fuhrman, B.; Aviram, M. Flavonoids protect LDL from oxidation and attenuate atherosclerosis. Curr. Opin. Lipidol. 2001, 12, 41-8.
21. Howard, A.; Chopra, M.; Thurnham, D.; Strain, J.; Fuhrman, B.; Aviram, M. Red wine consumption and inhibition of LDL oxidation: what are the important components. Med. Hypotheses 2002, 59, 101-4.
22. da Silva Porto, P. A.; Laranjinha, J. A.; de Freitas, V. A. Antioxidant protection of low density lipoprotein by procyanidins: structure/activity relationships. Biochem. Pharmacol. 2003, 66, 947-54.
23. Pace-Asciak, C. R.; Hahn, S.; Diamandis, E. P.; Soleas, G.; Goldberg, D. M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: implications for protection against coronary heart disease. Clin. Chim. Acta 1995, 235, 207-19.
24. Pace-Asciak, C. R.; Rounova, O.; Hahn, S. E.; Diamandis, E. P.; Goldberg, D. M. Wines and grape juices as modulators of platelet aggregation in healthy human subjects. Clin. Chim. Acta 1996, 246, 163-82.
25. Halpern, M. J.; Dahlgren, A. L.; Laakso, I.; Seppanen-Laakso, T.; Dahlgren, J.; McAnulty, P. A. Red-wine polyphenols and inhibition of platelet aggregation: possible mechanisms, and potential use in health promotion and disease prevention. J. Int. Med. Res. 1998, 26, 171-80.
26. Dell'Agli, M.; Busciala, A.; Bosisio, E. Vascular effects of wine polyphenols. Cardiovasc. Res. 2004, 63, 593-602.
27. Fumagalli, F.; Rossoni, M.; Iriti, M.; di Gennaro, A.; Faoro, F.; Borroni, E.; Borgo, M.; Scienza, A.; Sala, A.; Folco, G. From field to health: a simple way to increase the nutraceutical content of grape as shown by NO-dependent vascular relaxation. J. Agric. Food Chem. 2006, 54, 5344-9.
28. Ivanov, V.; Carr, A. C.; Frei, B. Red wine antioxidants bind to human lipoproteins and protect them from metal ion-dependent and -independent oxidation. J. Agric. Food Chem. 2001, 49, 4442-9.
29. Freitas, V. D.; Glories, Y.; Bourgeois, G.; Vitry, C. Characterisation of oligomeric and polymeric procyanidins from grape seeds by Liquid Secondary Ion Mass Spectrometry (LSIMS). Phytochemistry 1998, 49, 1434-1441.
30. Vieira, O. V.; Laranjinha, J. A.; Madeira, V. M.; Almeida, L. M. Rapid isolation of low density lipoproteins in a concentrated fraction free from water-soluble plasma antioxidants. J. Lipid Res. 1996, 37, 2715-21.
31. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193, 265-75.
32. Laranjinha, J. A.; Almeida, L. M.; Madeira, V. M. Lipid peroxidation and its inhibition in low density lipoproteins: quenching of cis-parinaric acid fluorescence. Arch. Biochem. Biophys. 1992, 297, 147-54.
33. Frank, J.; Budek, A.; Lundh, T.; Parker, R. S.; Swanson, J. E.; Lourenco, C. F.; Gago, B.; Laranjinha, J.; Vessby, B.; Kamal-Eldin, A. Dietary flavonoids with a catechol structure increase alpha-tocopherol in rats and protect the vitamin from oxidation in vitro. J. Lipid Res. 2006, 47, 2718-25.
34. Holt, R. R.; Lazarus, S. A.; Sullards, M. C.; Zhu, Q. Y.; Schramm, D. D.; Hammerstone, J. F.; Fraga, C. G.; Schmitz, H. H.; Keen, C. L. Procyanidin dimer B2 [epicatechin-(4beta-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa. Am. J. Clin. Nutr. 2002, 76, 798-804.
35. Bonanome, A.; Pagnan, A.; Caruso, D.; Toia, A.; Xamin, A.; Fedeli, E.; Berra, B.; Zamburlini, A.; Ursini, F.; Galli, G. Evidence of postprandial absorption of olive oil phenols in humans. Nutr. Metab. Cardiovasc. Dis. 2000, 10, 111-20.
36. Bowry, V. W.; Ingold, K. U.; Stocker, R. Vitamin E in human low-density lipoprotein. When and how this antioxidant becomes a pro-oxidant. Biochem. J. 1992, 288 (Pt 2), 341-4.
37. Zhou, B.; Wu, L. M.; Yang, L.; Liu, Z. L. Evidence for alpha-tocopherol regeneration reaction of green tea polyphenols in SDS micelles. Free Radical Biol. Med. 2005, 38, 78-84.
38. Deckert, V.; Desrumaux, C.; Athias, A.; Duverneuil, L.; Palleau, V.; Gambert, P.; Masson, D.; Lagrost, L. Prevention of LDL alpha-tocopherol consumption, cholesterol oxidation, and vascular endothelium dysfunction by polyphenolic compounds from red wine. Atherosclerosis 2002, 165, 41-50.