Biobased epicatechin conjugates protect erythrocytes and nontumoral cell lines from H2O2-induced oxidative stress

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 10, 2009, Pages 4459-4465

  Ugartondo, Vanessa ^a   Mitjans, Montserrat ^a   Torres, Josep Lluís ^b   Vinardell, María Pilar ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

Author keywords

Antioxidants; Catechins; Lipid peroxidation; Polyphenols

Indexed keywords

ANTIOXIDANT; CATECHIN; DRUG DERIVATIVE; HYDROGEN PEROXIDE;

ANIMAL; ARTICLE; CELL LINE; CELL STRAIN 3T3; CELL SURVIVAL; DRUG EFFECT; ERYTHROCYTE; HEMOLYSIS; HUMAN; LIPID PEROXIDATION; METABOLISM; MOUSE; OXIDATIVE STRESS;

3T3 CELLS; ANIMALS; ANTIOXIDANTS; CATECHIN; CELL LINE; CELL SURVIVAL; ERYTHROCYTES; HEMOLYSIS; HUMANS; HYDROGEN PEROXIDE; LIPID PEROXIDATION; MICE; OXIDATIVE STRESS;

EID: 66149106589     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf900240a     Document Type: Article

References (42)

1. Torres, J. L.; Bobet, R. New flavanol-derivatives from grape (Vitis vinifera) byproducts. Antioxidant aminoethylthiol-flavan-3-ol conjugates from a polymeric waste fraction used as a source of flavanols. J. Agric. Food Chem. 2001, 49, 4627-4634.
2. Yilmaz, Y.; Toledo, R. T. Major flavonoids in grape seeds and skins: antioxidant capacity of catechin, epicatechin, and gallic acid. J. Agric. Food Chem. 2004, 52, 255-260.
3. Rice-Evans, C. Flavonoid antioxidants. Curr. Med. Chem. 2001, 5, 797-807.
4. Dai, F.; Miao, Q.; Zhou, B.; Yang, L.; Liu, Z. Protective effects of flavonols and their glycosides against free radical-induced oxidative hemolysis of red blood cells. Life Sci. 2006, 78, 2488-2493.
5. Kondo, K.; Kurihara, M.; Miyata, N.; Suzuki, T.; Toyoda, M. Scavenging mechanisms of (-)-epigallocatechin gallate and (-)-epicatechin gallate on peroxyl radicals and formation of superoxide during the inhibitory action. Free Radical Biol. Med. 1999, 27 (7-8), 855-863.
6. Middleton, E.; Kandaswami, C.; Theoharides, T. C. The effect of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 2000, 52, 673-751.
7. Chung, F. L.; Schwartz, J.; Herzog, C. R.; Yang, Y. M. Tea and cancer prevention: studies in animals and humans. J. Nutr. 2003, 133, 3268S-3274S.
8. Lozano, C.; Juliá, L.; Jiménez, A.; Touriño, S.; Centelles, J. J.; Cascante, M.; Torres, J. L. Electron-transfer capacity of catechin derivatives and influence on the cell cycle and apoptosis in HT29 cells. FEBS J. 2006, 273, 2475-2486.
9. Torres, J. L; Lozano, C.; Juliá, L.; Sánchez, F. J.; Anglada, J.; Centelles, J. J.; Cascante, M. Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties. Bioorg. Med. Chem. 2002, 10, 2497-2509.
10. Ugartondo, V.; Mitjans, M.; Lozano, C.; Torres, J. L.; Vinardell, M. P. Comparative study of the cytotoxicity induced by antioxidant epicatechin conjugates obtained from grape. J. Agric. Food Chem. 2006, 54, 6945-6950.
11. Torres, J.; Lozano, C.; Mather, P. Conjugation of cathechins with cysteine generates antioxidant compounds with enhanced neuroprotective activity. Phytochemistry 2005, 66, 2032-2037.
12. Maher, P.; Lewerenz, J.; Lozano, C.; Torres, J. L. A novel approach to enhancing cellular glutathione levels. J. Neurochem. 2008, 107 (3), 690-700.
13. Mitjans, M.; Martínez, V.; Del Campo, J.; Abajo, C.; Lozano, C.; Torres, J. L.; Vinardell, M P. Novel epicatechin derivatives with antioxidant activity modulate interleukin-1α release in lipopolysaccharide-stimulated human blood. Bioorg. Med. Chem. Lett. 2004, 14, 5031-5034.
14. Mitjans, M.; Del Campo, J.; Abajo, C.; Martínez, V.; Selga, A.; Lozano, C.; Torres, J. L.; Vinardell, M. P. Immunomodulatory activity of a new family of antioxidants obtained from grape polyphenols. J. Agric. Food Chem. 2004, 52, 7297-7299.
15. Lozano, C.; Torres, J.; Juliá, L.; Jiménez, A.; Centelles, J. J.; Cascante, M. Effect of new antioxidant cysteinyl-flavanol conjugates on skin cancer cells. FEBS Lett. 2005, 579, 4219-4225.
16. Grinberg, L. N.; Newmark, H.; Kitrossky, N.; Rahamim, E.; Chevion, M.; Rachmilewitz, E. A. Protective effects of tea polyphenols against oxidative damage to red blood cells. Biochem. Pharmacol. 1997, 54 (9), 973-978.
17. Teng, C. M.; Hsiao, G; Ko, F. N.; Lin, D. T.; Lee, S. S. N-Allylsecoboldine as a novel antioxidant against peroxidative damage. Eur. J. Pharmacol. 1996, 303 (1-2), 129-139.
18. Stocks, J.; Dormandy, T. L. The autooxidation of human red cell lipids induced by hydrogen peroxide. Br. J. Hamaetol 1971, 20, 95-111.
19. Srour, M. A.; Bilto, Y. Y.; Juma, M. Evaluation of different methods used to measure malonyldialdehyde in human erythrocytes. Clin. Hemorheol. Microcirc. 2000, 23 (1), 23-30.
20. Park, Y. H.; Han, D. W.; Suh, H.; Ryu, G. H.; Hyon, S. H.; Cho, B. K.; Park, J. C. Protective effects of green tea polyphenol against reactive oxigen species-induced oxidative stress in cultured rat calvarial osteoblast. Cell Biol. Toxicol. 2003, 19, 325-337.
21. Borenfreund, E.; Puerner, J. A. Toxicity determined in vitro by morphological alterations and neutral red absorption. Toxicol. Lett. 1985, 24(2/3), 119-124.
22. Riddell, R. J.; Clothier, R. H.; Ball, M. An evaluation of three in vitro cytotoxicity assays. Food Chem. Toxicol. 1986, 24 (6/7), 469-471.
23. Sroka, Z.; Cisowski, W. Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food Chem. Toxicol. 2003, 41, 753-758.
24. Caturla, N.; Vera-Samper, E.; Villalaín, J.; Mateo, C.; Micol, V. The relationship between the antioxidant and the antibacterial preperties of galloylated catechins and the structure of phospholipid model membranes. Free Radical Biol. Med. 2003, 34 (6), 648-662.
25. Sultana, R.; Ravagna, A.; Mohmmad-Abdul, H.; Calíbrese, V.; Butterfield, D. A. Ferulic acid ethyl ester protects neurons against amyloid β-peptide(1-42)-induced oxidative stress and neurotoxicity: relationship to antioxidant activity. J. Neurochem. 2005, 92, 749-758.
26. Lázaro, E.; Castillo, J. A.; Ráfols, C.; Rosés, M.; Clapés, P.; Torres, J. L. Interaction of antioxidant biobased epicatechin conjugates with biomembrane models. J. Agric. Food Chem. 2007, 55, 2901-2905.
27. Erlejman, A. G.; Verstraeten, S. V.; Fraga, C. G.; Oteiza, P. I. The interaction of flavonoids with membranes: potential determination of flavonoid antioxidant effects. Free Radical Res. 2004, 38 (12), 1311-1320.
28. Verstraeten, S. V.; Keen, C. L.; Schmitz, H. H.; Fraga, C. G.; Oteiza, P. I. Flavan-3-ols and procyanidins protect liposomes against lipid oxidation and disruption of the bilayer structure. Free Radical Biol. Med. 2003, 34 (1), 84-92.
29. Sroka, Z. Antioxidative and antiradical properties of plant phenolics. Z. Naturforsch. C 2005, 60 (11-12), 833-843.
30. Shi, J.; Yu, J.; Pohorly, J. E.; Kakuda, Y. Polyphenolics in grape seeds-biochemistry and functionality. J. Med. Food 2003, 6 (4), 291-299.
31. Pool-Zobel, B. L.; Adlercreutz, H.; Glei, M.; Liegibel, U. M.; Sittlingon, J.; Rowland, I.; Wähälä, K.; Rechkemmer, G. Isoflavonoids and lignans have different potentials to modulate oxidative genetic damage in human colon cells. Carcinogenesis 2000, 21 (6), 1247-1252
32. Fan, P.; Lou, H. Effects of polyphenols from grape seeds on oxidative damage to cellular DNA. Mol. Cell. Biochem. 2004, 267, 67-74.
33. Zhu, Q. X.; Shen, T.; Tu, D. Y.; Ding, R.; Liang, Z. Z.; Zhang, X. J. Protective effects of Ginkgo biloba leak extracts on trichloroethylene-induced human keratinocyte cytotoxicity and apoptosis. Skin Pharmacol. Physiol. 2005, 18, 160-169.
34. Morley, N.; Clifford, T.; Salter, L.; Campbell, S.; Gould, D.; Curnow, A. Tea green polyphenol (-)-epigallocatechin gallate and green tea can protect human cellular DNA from ultraviolet and visible radiation-induced damage. Photodermatol. Photoimmunol. Photomed. 2005, 21, 15-22.
35. Maier, K.; Schmitt-Landgraf, R.; Siegemund, B. Development of an in vitro test system with human skin cells for evaluation of phototoxicity. Toxicol. In Vitro 1991, 5, 457-461.
36. Zanatta, C. F.; Ugartondo, V.; Mitjans, M.; Rocha-Filho, P. A.; Vinardell, M. P. Low cytotoxicity of creams and lotions formulated with Buriti oil (Mauritia flexuosa) assessed by the neutral red release test. Food Chem. Toxicol. 2008, 46, 2776-2781.
37. Dijoux, N.; Guingand, Y.; Bourgeois, C.; Durand, S.; Fromageot, C.; Combe, C.; Ferret, P. J. Assessment of the phototoxic hazard of some essential oils using modified 3T3 neutral red uptake assay. Toxicol. In Vitro 2006, 20, 480-489.
38. Llópiz, N; Puiggròs, F.; Céspedes, E.; Arola, L.; Ardévol, A.; Bladé, C.; Salvadó, M. J. Antigenotoxic effect of grape seed procyanidin extract in Fao cells submitted to oxidative stress. J. Agric. Food Chem. 2004, 52, 1083-1087.
39. Roig, R.; Cascón, E.; Arola, L.; Bladé, C.; Salvadó, M. J. Procyanidins protect Fao cells against hydrogen peroxide-induced oxidative stress. Biochim. Biophys. Acta 2002, 1572 (1), 25-30.
40. Puiggròs, F.; Llópiz, N.; Ardévol, A.; Bladé, C.; Arola, Ll.; Salvadó, M. J. Grape seed procyanidins prevent oxidative injury by modulating the expression of antioxidant enzyme system. J. Agric. Food Chem. 2005, 53, 6080-6086.
41. Frankel, E. N.; Finley, J. W. How to standardize the multiplicity of methods to evaluate natural antioxidants. J. Agric. Food Chem. 2008, 56, 4901-4908.
42. Fraga, C. G. Plant polyphenols: how to translate their in vitro antioxidant actions to in vivo conditions. IUBMB Life 2007, 59, 308-315.