The EGCg-induced redox-sensitive activation of endothelial nitric oxide synthase and relaxation are critically dependent on hydroxyl moieties

Biochemical and Biophysical Research Communications

Volumn 393, Issue 1, 2010, Pages 162-167

  Auger, Cyril ^a   Kim, Jong Hun ^a   Chabert, Philippe ^b   Chaabi, Mehdi ^b   Anselm, Eric ^a   Lanciaux, Xavier ^a   Lobstein, Annelise ^b   Schini Kerth, Valérie B ^a  

^a University Louis Pasteur of Strasbourg   (France)

^b Institut du Médicament de Strasbourg   (France)

Author keywords

EGCg; Endothelial function; eNOS; Hydroxyl function; Polyphenols

Indexed keywords

APAMIN; CATALASE; CHARYBDOTOXIN; CYTOCHROME P450; ENDOTHELIAL NITRIC OXIDE SYNTHASE; EPICATECHIN; EPIGALLOCATECHIN; EPIGALLOCATECHIN GALLATE; HYDROETHIDINE; HYDROXYL GROUP; INDOMETACIN; PROTEIN KINASE B; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; SUPEROXIDE; SUPEROXIDE DISMUTASE; XANTHINE OXIDASE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CORONARY ARTERY; ENDOTHELIUM CELL; ENZYME ACTIVATION; ENZYME PHOSPHORYLATION; EXPERIMENTAL PIG; MITOCHONDRIAL RESPIRATION; MOLECULAR MECHANICS; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; VASODILATATION; WESTERN BLOTTING;

ANIMALS; CATECHIN; CORONARY VESSELS; ENDOTHELIUM, VASCULAR; ENZYME ACTIVATION; HYDROGEN PEROXIDE; NITRIC OXIDE SYNTHASE TYPE III; OXIDATION-REDUCTION; REACTIVE OXYGEN SPECIES; SUPEROXIDES; SWINE; VASODILATION;

SUS;

EID: 77249137656     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2010.01.112     Document Type: Article

References (34)

1. Hertog M.G., Feskens E.J., Hollman P.C., et al. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen elderly study. Lancet 342 (1993) 1007-1011
2. Renaud S., and de Lorgeril M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 339 (1992) 1523-1526
3. Kuriyama S., Shimazu T., Ohmori K., et al. Green tea consumption and mortality due to cardiovascular disease, cancer, and all causes in Japan: the Ohsaki study. JAMA 296 (2006) 1255-1265
4. Sasazuki S., Kodama H., Yoshimasu K., et al. Relation between green tea consumption and the severity of coronary atherosclerosis among Japanese men and women. Ann. Epidemiol. 10 (2000) 401-408
5. Kobayashi M., Unno T., Suzuki Y., et al. Heat-epimerized tea catechins have the same cholesterol-lowering activity as green tea catechins in cholesterol-fed rats. Biosci. Biotechnol. Biochem. 69 (2005) 2455-2458
6. Kavantzas N., Chatziioannou A., Yanni A.E., et al. Effect of green tea on angiogenesis and severity of atherosclerosis in cholesterol-fed rabbit. Vascul. Pharmacol. 44 (2006) 461-463
7. Cabrera C., Artacho R., and Gimenez R. Beneficial effects of green tea - a review. J. Am. Coll. Nutr. 25 (2006) 79-99
8. Di Paola R., Mazzon E., Muia C., et al. Green tea polyphenol extract attenuates lung injury in experimental model of carrageenan-induced pleurisy in mice. Respir. Res. 6 (2005) 66
9. Fitzpatrick D.F., Hirschfield S.L., and Coffey R.G. Endothelium-dependent vasorelaxing activity of wine and other grape products. Am. J. Physiol. Heart Circ. Physiol. 265 (1993) H774-H778
10. Engler M.B., Engler M.M., Chen C.Y., et al. Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults. J. Am. Coll. Nutr. 23 (2004) 197-204
11. Ndiaye M., Chataigneau M., Lobysheva I., et al. Red wine polyphenol-induced, endothelium-dependent NO-mediated relaxation is due to the redox-sensitive PI3-kinase/Akt-dependent phosphorylation of endothelial NO-synthase in the isolated porcine coronary artery. FASEB J. 19 (2005) 455-457
12. Ndiaye M., Chataigneau T., Chataigneau M., et al. Red wine polyphenols induce EDHF-mediated relaxations in porcine coronary arteries through the redox-sensitive activation of the PI3-kinase/Akt pathway. Br. J. Pharmacol. 142 (2004) 1131-1136
13. Stoclet J.C., Chataigneau T., Ndiaye M., et al. Vascular protection by dietary polyphenols. Eur. J. Pharmacol. 500 (2004) 299-313
14. Anselm E., Chataigneau M., Ndiaye M., et al. Grape juice causes endothelium-dependent relaxation via a redox-sensitive Src- and Akt-dependent activation of eNOS. Cardiovasc. Res. 73 (2007) 404-413
15. Kane M.O., Anselm E., Rattmann Y.D., et al. Role of gender and estrogen receptors in the rat aorta endothelium-dependent relaxation to red wine polyphenols. Vascul. Pharmacol. 51 (2009) 140-146
16. Kim J.A., Formoso G., Li Y., et al. Epigallocatechin gallate, a green tea polyphenol, mediates NO-dependent vasodilation using signaling pathways in vascular endothelium requiring reactive oxygen species and Fyn. J. Biol. Chem. 282 (2007) 13736-13745
17. Madeira S.V., Auger C., Anselm E., et al. eNOS activation induced by a polyphenol-rich grape skin extract in porcine coronary arteries. J. Vasc. Res. 46 (2009) 406-416
18. Ullrich V., and Bachschmid M. Superoxide as a messenger of endothelial function. Biochem. Biophys. Res. Commun. 278 (2000) 1-8
19. Mochizuki M., Yamazaki S., Kano K., et al. Kinetic analysis and mechanistic aspects of autoxidation of catechins. Biochim. Biophys. Acta 1569 (2002) 35-44
20. Hou Z., Sang S., You H., et al. Mechanism of action of (-)-epigallocatechin-3-gallate: auto-oxidation-dependent inactivation of epidermal growth factor receptor and direct effects on growth inhibition in human esophageal cancer KYSE 150 cells. Cancer Res. 65 (2005) 8049-8056
21. Sang S., Yang I., Buckley B., et al. Autoxidative quinone formation in vitro and metabolite formation in vivo from tea polyphenol (-)-epigallocatechin-3-gallate: studied by real-time mass spectrometry combined with tandem mass ion mapping. Free Radic. Biol. Med. 43 (2007) 362-371
22. Anselm E., Socorro V.F., Dal-Ros S., et al. Crataegus special extract WS 1442 causes endothelium-dependent relaxation via a redox-sensitive Src- and Akt-dependent activation of endothelial NO synthase but not via activation of estrogen receptors. J. Cardiovasc. Pharmacol. 53 (2009) 253-260
23. Miller Jr. F.J., Gutterman D.D., Rios C.D., et al. Superoxide production in vascular smooth muscle contributes to oxidative stress and impaired relaxation in atherosclerosis. Circ. Res. 82 (1998) 1298-1305
24. Utenova B.T., Malterud K.E., and Rise F. Antioxidant activity of O-protected derivatives of (-)-epigallocatechin-3-gallate: inhibition of soybean and rabbit 15-lipoxygenases. Arkiv. Org. Chem. 9 (2007) 6-16
25. Osanai K., Huo C., Landis-Piwowar K.R., et al. Synthesis of (2R, 3R)-epigallocatechin-3-O-(4-hydroxybenzoate), a novel catechin from Cistus salvifolius, and evaluation of its proteasome inhibitory activities. Tetrahedron 63 (2007) 7565-7570
26. Schroeter H., Heiss C., Balzer J., et al. (-)-Epicatechin mediates beneficial effects of flavanol-rich cocoa on vascular function in humans. Proc. Natl. Acad. Sci. USA 103 (2006) 1024-1029
27. Alexopoulos N., Vlachopoulos C., Aznaouridis K., et al. The acute effect of green tea consumption on endothelial function in healthy individuals. Eur. J. Cardiovasc. Prev. Rehabil. 15 (2008) 300-305
28. Stein J.H., Keevil J.G., Wiebe D.A., et al. Purple grape juice improves endothelial function and reduces the susceptibility of LDL cholesterol to oxidation in patients with coronary artery disease. Circulation 100 (1999) 1050-1055
29. Karatzi K., Papamichael C., Aznaouridis K., et al. Constituents of red wine other than alcohol improve endothelial function in patients with coronary artery disease. Coron. Artery Dis. 15 (2004) 485-490
30. Schini V.B., Boulanger C., Regoli D., et al. Bradykinin stimulates the production of cyclic GMP via activation of B2 kinin receptors in cultured porcine aortic endothelial cells. J. Pharmacol. Exp. Ther. 252 (1990) 581-585
31. Lorenz M., Wessler S., Follmann E., et al. A constituent of green tea, epigallocatechin-3-gallate, activates endothelial nitric oxide synthase by a phosphatidylinositol-3-OH-kinase-, cAMP-dependent protein kinase-, and Akt-dependent pathway and leads to endothelial-dependent vasorelaxation. J. Biol. Chem. 279 (2004) 6190-6195
32. Fraga C.G. Plant polyphenols: how to translate their in vitro antioxidant actions to in vivo conditions. IUBMB. Life 59 (2007) 308-315
33. Hong J., Lu H., Meng X., et al. Stability, cellular uptake, biotransformation, and efflux of tea polyphenol (-)-epigallocatechin-3-gallate in HT-29 human colon adenocarcinoma cells. Cancer Res. 62 (2002) 7241-7246
34. Edirisinghe I., Burton-Freeman B., and Kappagoda C.T. Mechanism of the endothelium-dependent relaxation evoked by a grape seed extract. Clin. Sci. 114 (2008) 331-337