Grape epicatechin conjugates prevent erythrocyte membrane protein oxidation

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 16, 2012, Pages 4090-4095

  Martinez V ^a   Ugartondo, V ^a   Vinardell, M P ^a   Torres, J L ^b   Mitjans, M ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

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

Author keywords

AAPH; band 3; cell morphology; epicatechin; erythrocytes; membrane fluidity; membrane protein

Indexed keywords

AAPH; BAND 3; CELL MORPHOLOGY; EPICATECHIN; ERYTHROCYTES; MEMBRANE FLUIDITY; MEMBRANE PROTEINS;

AGENTS; CYTOLOGY; ELECTROPHORESIS; FLUIDITY; FRUITS; LIPID BILAYERS; MEMBRANES; MORPHOLOGY; SCANNING ELECTRON MICROSCOPY; SODIUM; SODIUM SULFATE;

CELL MEMBRANES;

CATECHIN; MEMBRANE PROTEIN; PLANT EXTRACT;

ARTICLE; CHEMISTRY; DRUG EFFECT; ERYTHROCYTE; ERYTHROCYTE MEMBRANE; HUMAN; METABOLISM; OXIDATION REDUCTION REACTION; VITIS;

CATECHIN; ERYTHROCYTE MEMBRANE; ERYTHROCYTES; HUMANS; MEMBRANE PROTEINS; OXIDATION-REDUCTION; PLANT EXTRACTS; VITIS;

VITACEAE;

EID: 84860342090     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2051784     Document Type: Article

References (26)

1. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biol. Med. 1996, 20, 933-956 (Pubitemid 26157509)
2. Proteggente, A. R.; Pannala, A. S.; Paganga, G.; Van Buren, L.; Wagner, E.; Wiseman, S.; Van De Put, F.; Dacombe, C.; Rice-Evans, C. A. The antioxidant activity of regularly consumed fruit and vegetables reflects their phenolic and vitamin C composition Free Radical Res. 2002, 36, 217-233
3. Rice-Evans, C. A. Implications of the mechanisms of action of tea polyphenols as antioxidants in vitro for chemoprevention in humans Proc. Soc. Exp. Biol. Med. 1999, 220, 262-266
4. Salah, N.; Miller, N. J.; Paganga, G.; Tijburg, L.; Bolwell, G. P.; Rice-Evans, C. Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants Arch. Biochem. Biophys. 1995, 322, 339-346
5. Torres, J. L.; Bobet, R. New flavanol-derivatives from grape (Vitis vinifera) byproducts. Antioxidant aminothylthiol-flavan-3-ol conjugates from a polymeric waste fraction used as a source of flavanols J. Agric. Food Chem. 2001, 49, 4627-4634 (Pubitemid 32988696)
6. 2-induced oxidative stress J. Agric. Food Chem. 2009, 57, 4459-4465
7. 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 (Pubitemid 44426981)
8. Beckman, K. B.; Ames, B. N. The free radical theory of aging matures Physiol. Rev. 1998, 78, 547-581 (Pubitemid 28182903)
9. Sato, Y.; Sato, K.; Suzuki, Y. Mechanism of free radical-induced hemolysis of human erythrocytes: Comparison of calculated rate constants for hemolysis with experimental rate constants Arch. Biochem. Biophys. 1999, 366, 61-69 (Pubitemid 29394229)
10. Lozano, C.; Julià, L.; Jimenez, 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 (Pubitemid 43736660)
11. Shinitzky, M.; Barenholz, Y. Fluidity parameters of lipid regions determined by fluorescence polarization Biochim. Biophys. Acta 1978, 515, 367-394 (Pubitemid 9099585)
12. Fairbanks, G.; Theodore, L.; Steck, S.; Wallach, D. F. H. Electrophoretic analysis of the major polypeptides of the human erythrocyte membrane Biochemistry 1971, 10, 2606-2617
13. 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 (Pubitemid 34626214)
14. Srour, M. A.; Bilto, Y. Y.; Juma, M.; Irhimeh, M. R. Exposure of human erythrocytes to oxygen radicals causes loss of deformability, increased osmotic fragility, lipid peroxidation and protein degradation Clin. Hemorheol. Microcirc. 2000, 23, 13-21 (Pubitemid 32047488)
15. 3+-mediated lipid oxidation: Effect of galactolipids Biochem. J. 1998, 333, 833-838
16. Kaiser, R. D.; London, E. Location of diphenylhexatriene (DPH) and its derivatives within membranes: Comparison of different fluorescence quenching analyses of membrane depth Biochemistry 1998, 37, 8180-8190 (Pubitemid 28307081)
17. Mély-Goubert, B.; Freedman, M. H. Lipid fluidity and membrane protein monitoring using 1,6-diphenyl-1,3,5-hexatriene Biochim. Biophys. Acta 1980, 601, 315-317
18. Lázaro, E.; Castillo, J. A.; Ràfols, 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 (Pubitemid 46668296)
19. Schnitzer, E.; Pinchuk, I.; Lichtenberg, D. Peroxidation of liposomal lipids Eur. Biophys. J. 2007, 36, 499-515 (Pubitemid 46626218)
20. Arora, A.; Byrem, T. M.; Nair, M. G.; Strasburg, G. M. Modulation of liposomal membrane fluidity by flavonoids and isoflavonoids Arch. Biochem. Biophys. 2000, 373, 102-109 (Pubitemid 30046494)
21. Tsuchiya, H. Structure-dependent membrane interaction of flavonoids associated with their bioactivity Food. Chem. 2010, 120, 1089-1096
22. Lim, H. W. G.; Wortis, M.; Mukhopadhyay, R. Stomatocyte-discocyte- echinocyte sequence of the human red blood cell: Evidence for the bilayer-couple hypothesis from membrane mechanics Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 16766-16769 (Pubitemid 36034047)
23. Celedón, G.; González, G.; Ferrer, V.; Lissi, E. A. Peroxyl-oxidized erythrocyte membrane band 3 protein with anion transport capacity is degraded by membrane-bound proteinase Free Radical Res. 2004, 38, 1055-1059 (Pubitemid 39504340)
24. Celedón, G.; González, G.; Lissi, E. A.; Hidalgo, G. Free radical-induced protein degradation of erythrocyte membrane is influenced by the localization of radical generation IUBMB Life 2001, 51, 377-380 (Pubitemid 33096659)
25. Celedon, G.; Gonzalez, G.; Pino, J.; Lissi, E. A. Peroxynitrite oxidizes erythrocyte membrane band 3 protein and disminishes its anion transport capacity Free Radical Res. 2007, 41, 316-323 (Pubitemid 46404474)
26. Chen, R.; Wang, J. B.; Zhang, X. Q.; Ren, J.; Zeng, C. M. Green tea polyphenol epigallocatechin-3-gallate (EGCG) induced intermolecular cross-linking of membrane proteins Arch. Biochem. Biophys. 2011, 507, 343-349