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Review Article

Natural and synthetic antioxidants: An updated overview

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Pages 1216-1262 | Received 15 Mar 2010, Published online: 13 Sep 2010

References

  • Sies H. Oxidative stress. Orlando: Academic Press; 1958.
  • Cipak A, Gasparovic A, Lovakovic T, Zarkovic N. Oxidative stress and antioxidants: biological response modifiers of oxidative homeostasis in cancer. Period Biol 2010; in press.
  • Cipak A, Jaganjac M, Tehlivets O, Kohlwein SD, Zarkovic N. Adaptation to oxidative stress induced by polyunsaturated fatty acids in yeast. Biochim Biophys Acta 2008;1781: 283–287.
  • Hyoudou K, Nishikawa M, Kobayashi Y, Umeyama Y, Yamashita F, Hashida M. PEGylated catalase prevents metastatic tumor growth aggravated by tumor removal. Free Radic Biol Med 2006;41:1449–1458.
  • Child R, Brown S, Day S, Donnelly A, Roper H, Saxton J. Changes in indices of antioxidant status, lipid peroxidation and inflammation in human skeletal muscle after eccentric muscle actions. Clin Sci (Lond) 1999;96:105–115.
  • Ji LL, Radak Z, Goto S. Hormesis and exercise: how the cell copes with oxidative stress. Am J Pharm Toxicol 2008;3: 41–55.
  • Venskutonis PR. Food additives: the dilemma of “synthetic or natural”. Acta Aliment Hung 2004;33:1–5.
  • Nijveldt RJ, van Nood E, van Hoorn DEC, Boelens PG, van Norren K, van Leeuwen PAM. Flavonoids: a review of probable mechanisms of action and potential applications. Am J Clin Nutr 2001;74:418–425.
  • Tomczyk M, Latté KP. Potentilla-A review of its phytochemical and pharmacological profile. J Ethnopharmacol 2009;122: 184–204.
  • Kokoska L, Janovska D. Chemistry and pharmacology of Rhaponticum carthamoides: a review. Phytochemistry 2009; 70:842–855.
  • Miliauskas G, Venskutonis PR, van Beek TA. Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food Chem 2004;85:231–237.
  • Miliauskas G, van Beek TA, Venskutonis PR, Linssen JPH, de Waard P, Sudholter EJ. Antioxidant activity of Potentilla fruticosa. J Food Sci Agric 2004;84:1997–2009.
  • Miliauskas G, van Beek TA, de Waard P, Venskutonis PR, Sudholter EJR. Identification of radical scavenging compounds in Rhaponticum carthamoides by means of LC-DAD-SPE-NMR. J Nat Prod 2005;68:168–172.
  • Miliauskas G, van Beek TA, Venskutonis PR, Linssen JPH, de Waard P. Antioxidative activity of Geranium macrorrhizum. Eur Food Res Technol 2004;218:253–261.
  • Venskutonis PR, Dedonytė V, Lazutka J, Slapšytė G, Marozienė A, Nemeikaitė-Čėnienė A, Če.ėnas N, Miliauskas G. A preliminary assessment of singlet oxygen scavenging, cytotoxic and genotoxic properties of Geranium macrorrhizum extracts. Acta Biochim Pol 2010;57:157–163.
  • Schilter B, Andersson C, Anton R, Constable A, Kleiner J, O’Brien J, Renwick AG, Korver O, Smit F, Walker R. Guidance for the safety assessment of botanicals and botanical preparations for use in food and food supplements. Food Chem Toxicol 2003;41:1625–1649.
  • Bandonienė D, Pukalskas A, Venskutonis PR, Gruzdienė D. Preliminary screening of antioxidant activity of some plant extracts in rapeseed oil. Food Res Int 2000;33:785–791.
  • Pukalskas A, van Beek TA, Venskutonis RP, Linssen JPH, van Veldhuizen A, de Groot A. Identification of radical scavengers in sweet grass (Hierochloe odorata). J Agric Food Chem 2002;50:2914–2929.
  • Nemeikaite-Ceniene A, Maroziene A, Pukalskas A, Venskutonis PR, Cenas N. Redox properties of novel antioxidant 5,8-dihydroxycoumarin: implications for its prooxidant cytotoxicity. Z Naturforsch C 2005;60:849–854.
  • Venskutonis PR, Pukalskas A, Cenas N, Maroziene A, Lazutka J, Slapsyte G, Kevelaitis E, Laukeviciene A. Chemical and toxicological characterisation of strong antioxidants from sweet grass (Hierochloe odorata L.). Molecular and physiological Effects of Bioactive Food Compounds. Part 1 - Dietary Phytochemicals and Health: from Molecular Targets to Biomarkers of Efficacy. Vienna; Medicinishe Universität Wien & Universität Wien; 2006: 221.
  • Grigonis D, Venskutonis PR, Sivik B, Sandahl M, Eskilsson CS. Comparison of different extraction techniques for isolation of antioxidants from sweet grass (Hierochloe odorata). J Supercrit Fluids 2005;33:223–233.
  • Pukalskas A, Venskutonis PR, Linssen JPH. Effect of plant extracts on lipid oxidation in Dutch style fermented sausage. Molecular and physiological Effects of Bioactive Food Compounds. Part 1 - Dietary Phytochemicals and Health: from Molecular Targets to Biomarkers of Efficacy. Vienna; Medicinishe Universität Wien & Universität Wien; 2006: 199.
  • Damašius J, Venskutonis PR, Fogliano V. Influence of sweet grass extract and from it isolated strong antioxidant 5,8-dihydroxycoumarin on the formation of PhIP in meat. Sørensen H, Sørensen S, Sørensen AD, Sørensen JC, Andersen KE, Bjergegaard C., Møller P. Food for the Future – the Contribution of Chemistry to Improvement of Food Quality 2. Copenhagen: Faculty of Life Sciences, University of Copenhagen, Denmark; 2009: 138 – 141.
  • Zainuddin A, Pokorny J, Venskutonis R. Antioxidant activity of sweetgrass (Hierochloe odorata Wahlnb.) extract in lard and rapeseed oil emulsions. Food/Nahrung 2002;46:15–17.
  • Tirzitis G, Bartosz G. Determination of antiradical and antioxidant activity: basic principles and new insights. Acta Biochim Pol 2010;57:139–142.
  • Miliauskas G, Mulder E, Linssen JPH, Houben JH, van Beek TA, Venskutonis PR. Evaluation of antioxidative properties of Geranium macrorrhizum and Potentilla fruticosa extracts in Dutch style fermented sausages. Meat Sci 2007;77:703–708.
  • Yanishlieva NV, Marinova E, Pokorny J. Natural antioxidants from herbs and spices. Eur J Lipid Sci Technol 2006;108: 776–793.
  • Carbone F, Mourgues F, Perrotta G, Rosati C. Advances in functional research of antioxidants and organoleptic traits in berry crops. Biofactors 2008;34:23–36.
  • Amarowicz R, Pegg RB. Legumes as a source of natural antioxidants. Eur J Lipid Sci Technol 2008;110:865–878.
  • Patil BS, Jayaprakasha GK, Murthy KNC, Vikram A. Bioactive compounds: historical perspectives, opportunities, and challenges. J Agric Food Chem 2009;57:8142–8160.
  • Ali SS, Kasoju N, Luthra A, Singh A, Sharanabasava H, Sahu A, Bora U. Indian medicinal herbs as sources of antioxidants. Food Res Int 2008;41:1–15.
  • Suhaj M. Spice antioxidants isolation and their antiradical activity: a review. J Food Compos Anal 2006;19:531–537.
  • Kiokias S, Varzakas T, Oreopoulou V. In vitro activity of vitamins, flavonoids, and natural phenolic antioxidants against the oxidative detereioration of oi-based systems. Crit Rev Food Sci Nutr 2008;48:48–78.
  • Moure A, Cruz JM, Franco D, Domínguez JM, Sineiro J, Domínguez H, Núñez MJ, Parajó JC. Natural antioxidants from residual sources. Food Chem 2001;72:145–171.
  • Dvaranauskaite A, Venskutonis PR, Raynaud C, Talou T, Viškelis P, Dambrauskiene E. Characterization of steam volatiles in the essentials oil of black currant buds and the antioxidant properties of different bud extracts. J Agric Food Chem 2008;56:3279–3286.
  • Bartosz G. Total antioxidant capacity. Adv Clin Chem 2003; 37:219–292.
  • Niederländer HA, van Beek TA, Bartasiute A, Koleva II. Antioxidant activity assays on-line with liquid chromatography. J Chromatogr A 2008;1210:121–134.
  • Bartosz G. Nonenzymatic antioxidant capacity assays: limitations of use in biomedicine. Free Radic Res 2010; 44:711–720.
  • Prior RL, Wu X, Schaich K. Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J Agric Food Chem 2005;53: 4290–4302.
  • Huang D, Ou B, Prior RL. The chemistry behind antioxidant capacity assays. J Agric Food Chem 2005;53:1841–1856.
  • Roginsky V, Lissi EA. Review of methods to determine chain-breaking antioxidant activity in food. Food Chem 2005;92: 235–254.
  • Moon J-K, Shibamoto T. Antioxidant assays for plant and food components. J Agric Food Chem 2009;57:1655–1666.
  • Pastore D, Laus MN, Tozzi D, Fogliano V, Soccio M, Flagella Z. New tool to evaluate a comprehensive antioxidant activity in food extracts: bleaching of 4-nitroso-N,N-dimethylaniline catalyzed by soybean lipoxygenase-1. J Agric Food Chem 2009;57:9682–9692.
  • Shi S-Y, Zhou H-H, Zhang Y-P, Jiang X-Y, Chen X-Q, Huang K-L. Coupling HPLC to on-line, post-column (bio)chemical assays for high-resolution screening of bioactive compounds from complex mixtures. TRAC-Trend Anal Chem 2009;28: 865–877.
  • Tung Y-T, Wu J-H, Hsieh C-Y, Chen P-S, Chang S-T. Free radical-scavenging phytochemicals of hot water extracts of Acacia confusa leaves detected by an on-line screening method. Food Chem 2009;115:1019–1024.
  • Jimenez-Alvarez D, Giuffrida F, Vanrobaeys F, Golay PA, Cotring C, Lardeau A, Keely BJ. High-throughput methods to assess lipophilic and hydrophilic antioxidant capacity of food extracts in vitro. J Agric Food Chem 2008;56: 3470–3477.
  • Blasco AJ, Crevillén AG, González MC, Escarpa A. Direct electrochemical sensing and detection of natural antioxidants and antioxidant capacity in vitro systems. Electroanal 2007;19:2275–2286.
  • Gazdik Z, Krska B, Adam V, Saloun J, Pokorna T, Reznicek V, Horna A, Kizek R. Electrochemical determination of the antioxidant potential of some less common fruit species. Sensors 2008;8:7564–7570.
  • Magalhães LM, Segundo MA, Reis S, Lima JLFC, Rangel AOSS. Automatic method for the determination of Folin-Ciocalteu reducing capacity in food products. J Agric Food Chem 2006;54:5241–5246.
  • Karyakina EE, Vokhmyanina DV, Sizova NV, Sabitov AN, Borisova AV, Sazontova TG, Arkhipenko YV, Tkachuk VA, Zolotov YA, Karyakin AA. Kinetic approach for evaluation of total antioxidant activity. Talanta 2009;80:749–753.
  • Omata Y, Saito Y, Yoshida Y, Niki E. Simple assessment of radical scavenging capacity of beverages. J Agric Food Chem 2008;56:3386–3390.
  • Becker EM, Nissen LR, Skibsted LH. Antioxidant evaluation protocols: food quality or health effects. Eur Food Res Technol 2004;219:561–571.
  • Bartasiute A, Westerink BHC, Verpoorte E, Niederlander HAG. Improving the in vivo predictability of an on-line HPLC stable free radical decoloration assay for antioxidant activity in methanol-buffer medium. Free Radic Biol Med 2007;42: 413–423.
  • Wolfe KL, Liu RH. Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements. J Agric Food Chem 2007;55:8896–8907.
  • Wolfe KL, Liu RH. Structure-activity relationships of flavonoids in the cellular antioxidant activity. J Agric Food Chem 2008;56:8404–8411.
  • Wolfe KL, Kang XM, He XJ, Dong M, Zhang QY, Liu RH. Cellular antioxidant activity of common fruits. J Agric Food Chem 2008;56:8418–8426.
  • Tsao R, Deng Z. Separation procedures for naturally occurring antioxidant phytochemicals. J Chromatogr B 2004;812: 85–99.
  • Herrero M, Ibáñez E, Cifuentes A. Analysis of natural antioxidants by capillary electromigration methods. J Sep Sci 2005;28:883–897.
  • Harold N, Graham PD. Green tea composition, consumption and polyphenol chemistry. Prev Med 1992;21:334–350.
  • Freiburg ES, Heidelberg BB. Camellia sinensis (L.) O. Kumtze Der Teestrauch: Inhaltsstoffe und Wirkungen von grünen und schwarzen Tee. Portrait einer Arzneipflanze. Z Phytother 1995;16:231–246.
  • Balentine AD. Manufacturing and chemistry of tea. Chi-Tang H, Chang YL, Mou-Tuan H. Phenolic compounds in food and their effects of health. Washington, D.C.: American Chemical Society; 1992. 103–117.
  • Katiyar SK, Mukhtar H. Tea in chemoprevention of cancer: epidemiologic and experimental studies. Int J Oncol 1996; 8:221–238.
  • Łuczaj W, Skrzydlewska E. Antioxidant properties of black tea in alcohol intoxication. Food Chem Toxicol 2004;42: 2045–2051.
  • Ostrowska J, Luczaj W, Augustyniak A, Skrzydlewska E. Green and black tea in brain protection. Qureshi GA, Parvez SH. Oxidative stress and neurodegenerative disorders: Elsevier, Amsterdam; 2007. 581–600.
  • Ostrowska J, Łuczaj W, Skrzydlewska E. Are teas the universal antioxidants? Panglossi HV. Leading edge antioxidants research. New York: Nova Science; 2007. 65–87.
  • Zapora E, Hołub M, Waszkiewicz E, Dąbrowska M, Skrzydlewska E. Green tea effect on antioxidant status of erythrocytes and on haematological parameters in rats. Bull Vet Inst Puławy 2009;53:139–145.
  • Łuczaj W, Zapora E, Skrzydlewska E. Influence of green tea on erythrocytes antioxidant status of different age rats intoxicated with ethanol. Phytother Res 2010;24:424–428.
  • Haslam E. Thoughts on thearubigins. Phytochemistry 2003; 64:61–73.
  • Davies AP, Goodsall C, Cai Y, Davis AL, Lewis JR, Wilkins J, Wan X, Clifford MN, Powel C, Parry A, Thiru A, Safford R, Nursten HE. Black tea dimeric and oligomeric pigments-structures and formation. Gross CG, Hemingway RW, Yoshida T. Plant polyphenols 2: Chemistry, biology, pharmacology, ecology. New York: Kluwar Academic/Plenum Press; 1999;697–725.
  • Tanaka T, Watarumi S, Matsuo Y, Kamei M, Kouno I. Production of theasinensins A and D, epigallocatechin gallate dimers of black tea, by oxidation - reduction of dehydrotheasinensin A. Tetrahedron Lett 2003;59:7939–7947.
  • Rice-Evans CA, Miller NJ, Paganga G. Antioxidant properties of phenolic compounds. Trends Plant Sci 1997;2: 152–159.
  • Hazakira M, Mahanta PK. Some studies on carotenoids and their degradation in black tea manufacture. J Sci Food Agric 1983;34:1390–1396.
  • Higdon JV, Frei B. Tea catechins and polyphenols: health effects, metabolism, and antioxidant functions. Crit Rev Food Sci Nutr 2003;43:89–143.
  • Łuczaj W, Waszkiewicz E, Roszkowska-Jakimiec W, Skrzydlewska E. Green tea protection against age-dependent ethanol-induced oxidative stress. J Toxicol Env Health 2004;67:595–606.
  • Ostrowska J, Łuczaj W, Kasacka I, Różański A, Skrzydlewska E. Green tea protects against ethanol-induced lipid peroxidation in rat organs. Alcohol Clin Exp Res 2004;32:25–32.
  • Skrzydlewska E, Ostrowska J, Luczaj W, Augustyniak A. Green and black tea in brain protection. Qureshi GA, Parvez SH. Oxidative Stress and Neurodegenerative Disorders. : Elsevier; 2007. 581–600.
  • Łuczaj W, Walerowicz T, Skrzydlewska E, Buszewski B. Chromatographic examinations of tea protection against lipid oxidative modifications. Toxicol Mech Methods 2008;18: 483–490.
  • Feng WY. Metabolism of green tea catechins: an overview. Curr Drug Metab 2006;7:755–809.
  • Manach C, Scalbert A, Morand C, Rémésy C, Am CJ. Polyphenols: food sources and bioavailability. J Clin Nutr 2004;79:727–747.
  • Yang F, Oz HS, Barve S, DeVilliers WJ, McClain CJ, Varilek GW. The green tea polyphenol EGCG blocks nuclear factor-kappa B activation by inhibiting I kappa B kinase activity in the intestinal epithelial cell line IEC-6. Mol Pharmacol 2001;60:528–533.
  • Mulder TP, Rietveld AG, van Amelsvoort JM. Consumption of both black tea and green tea results in an increase in the excretion of hippuric acid into urine. Am J Clin Nutr 2005;81:256–260.
  • Augustyniak A, Waszkiewicz E, Skrzydlewska E. Preventive action of green tea from changes in the liver antioxidant abilities of different aged rats intoxicated with ethanol. Nutrition 2005;21:925–932.
  • Łuczaj W, Siemieniuk E, Roszkowska-Jakimiec W, Skrzydlewska E. Protective effect of black tea against ethanol-induced oxidative modifications of liver proteins and lipids. J Stud Alcohol 2006;67:510–518.
  • Skrzydlewska E, Augustyniak A, Michalak K, Farbiszewski R. Green tea supplementation in rats of different ages mitigates ethanol-induced changes in brain antioxidant abilities. Alcohol 2005;37:89–98.
  • Warden BA, Smith LS, Beecher GR, Balentine DA, Clevidence BA. Catechins are bioavailable in men and women drinking black tea throughout the day. J Nutr 2001;131: 1731–1737.
  • Agarwal A, Prasad R, Jain A. Effect of green tea extract (catechins) in reducing oxidative stress seen in patients of pulmonary tuberculosis on DOTS Cat I regimen. Phytomedicine 2010;17:23–72.
  • Sharma V, Rao LJ. A thought on the biological activities of black tea. Crit Rev Food Sci Nutr 2009;49:379–404.
  • Dou QP. Molecular mechanisms of green tea polyphenols. Nutr Cancer 2009;61:827–835.
  • Lin JK, Chen PC, Ho CT, Lin-Shiau S, Y. Inhibition of xanthine oxidase and suppression of intracellular reactive oxygen species in HL-60 cells by theaflavin-3,3’-digallate, (-)-epigallocatechin-3-gallate, and propyl gallate. J Agric Food Chem 2000;48:2736–2743.
  • Dew TP, Day AJ, Morgan MRA. Xanthine oxidase activity in vitro: effects of food extracts and components. J Agric Food Chem 2005;53:6510–6515.
  • Persson IA, Persson K, Hägg S, Andersson RG. Effects of green tea, black tea and Rooibos tea on angiotensin-converting enzyme and nitric oxide in healthy volunteers. 2010;10:1–8.
  • Kostyuk VA, Kraemer T, Sies H, Schewe T. Myeloperoxidase/nitrite mediated lipid peroxidation of LDL as modulated by flavonoids. FEBS Lett 2003;537:146–150.
  • Zhu QY, Hackman RM, Ensuna JL, Holt RR, Keen CL. Antioxidative activities of oolong tea. J Agric Food Chem 2002;50:6929–6934.
  • Roy P, Nigam N, Singh M, George J, Srivastava S, Naqvi H, Shukla Y. Tea polyphenols inhibit cyclooxygenase-2 expression and block activation of nuclear factor-kappa B and Akt in diethylnitrosoamine induced lung tumors in Swiss mice. Invest New Drugs 2009;28:466–471.
  • Leung LK, Su Y, Chen R, Zhang Z, Huang Y, Chen ZY. Theaflavins in black tea and catechins in green tea are equally effective antioxidants. J Nutr 2001;131:2248–2251.
  • Yang Z, Jie G, Dong F, Xu Y, Watanabe N, Tu Y. Radical-scavenging abilities and antioxidant properties of theaflavins and their gallate esters in H2O2-mediated oxidative damage system in the HPF-1 cells. Toxicol in Vitro 2008;22: 1250–1256.
  • Jovanavic SV, Steenken S, Simic MG. Reduction potentials of flavonoid and model phenoxyl radicals. J Chem Soc Perkins Trans 1996;2:2497–2503.
  • Jovanavic SV, Hara Y, Steenken S, Simic MG. Antioxidant potential of gallocatechins. A pulse radiolysis and laser photolysis study. J Am Chem Soc 1997;119:5337–5343.
  • Łuczaj W, Skrzydlewska E. Antioxidative properties of black tea. Prev Med 2005;40:910–918.
  • Kazi A, Wang Z, Kumar N, Falesti SC, Chan TH, Dou QP. Structure-activity relationship of synthetic analogs of (-)- epigallocatechin-3-gallate as proteasome inhibitors. Anticancer Res 2004;24:943–954.
  • Hurrell RF, Reddy M, Cook JD. Inhibition of non-haem iron absorption in man by polyphenolic-containing beverages. Br J Nutr 1999;81:189–195.
  • Augustyniak A, Ostrowska J, Łuczaj W, Skrzydlewska E. Comparison of antioxidative properties of green and black tea. Panglossi HV. Leading edge antioxidants research. New York: Nova Science Publishers; 2007. 17–34.
  • Arora A, Byrem TM, Nair MG, Strasburg GM. Modulation of liposomal membrane fluidity by flavonoids and isoflavonoids. Arch Biochem Biophys 2000;373:102–109.
  • Tsuchiya H. Effects of green tea catechins on membrane fluidity. Pharmacology 1999;59:34–44.
  • Szachowicz-Petelska B, Dobrzyńska I, Skrzydlewska E, Figaszewski Z. Influence of green tea on surface charge density and phospholipids composition of erythrocytes membrane in ethanol intoxicated rats. Cell Biol Toxicol 2005; 21:61–70.
  • Dobrzyńska I, Szachowicz-Petelska B, Ostrowska J, Skrzydlewska E, Figaszewski Z. Protective effect of green tea on erythrocyte membrane of different age rats intoxicated with ethanol. Chem Biol Int 2005;156:41–53.
  • Dobrzyńska I, Szachowicz-Petelska B, Skrzydlewska E, Figaszewski Z. Effects of green tea on physico-chemical properties of liver cell membranes of rats intoxicated with ethanol. Pol J Env Stud 2008;17:327–333.
  • Szachowicz-Petelska B, Skrzydlewska E, Figaszewski Z. Changes in protein composition in erythrocyte membrane of ethanol-poisoned rats after administration of teas. Anal Lett 2010;43:721–734.
  • Saija A, Scalese M, Lanza M, Marzullo D, Bonina F, Castelli F. Flavonoids as antioxidant agents: importance of their interaction with biomembranes. Free Radic Biol Med 1995;19:481–486.
  • Ostrowska J, Skrzydlewska E. The comparison of effect of catechins and green tea extract on oxidative modification of LDL in vitro. Adv Med Sci 2006;51:298–303.
  • Hall ED. Free radicals and neuroprotection in traumatic brain and spinal cord injury. Lajtha A, Banik N, Ray SK. Handbook of neurochemistry and molecular neurobiology. 3rd. Springer, New York; 2009. 203–228.
  • Satoh E, Tohyama N, Nishimura M. Comparison of the antioxidant activity of roasted tea with green, oolong, and black teas. Int J Food Sci Nutr 2005;56:551–559.
  • Vinson JA, Teufel K, Wu N. Green and black teas inhibit atherosclerosis by lipid, antioxidant and fibrinolytic mechanisms. J Agric Food Chem 2004;52:3661–3665.
  • Stangl V, Dreger H, Stangl K, Lorenz M. Molecular targets of tea polyphenols in the cardiovascular system. Cardiovasc Res 2007;73:348–358.
  • Łuczaj W, Zapora E, Szczepański M, Wnuczko K, Skrzydlewska E. Polyphenols action against oxidative stress formation in endothelial cells. Acta Pol Pharm 2009;66:617–624.
  • Dell’Agli M, Buscialà A, Bosisio E. Vascular effects of wine polyphenols. Cardiovasc Res 2004;63:593–602.
  • Pal S, Ho N, Santos C, Dubois P, Mamo J, Croft K, Allister E. Red wine polyphenolics increase LDL receptor expression and activity and suppress the secretion of ApoB100 from human HepG2 cells. J Nutr 2003;133:700–706.
  • Li L, Stillemark-Billton P, Beck C, Boström P, Andersson L, Rutberg M, Ericsson J, Magnusson B, Marchesan D, Ljungberg A, Borén J, Olofsson SO. Epigallocatechin gallate increases the formation of cytosolic lipid droplets and decreases the secretion of apoB-100 VLDL. J Lipid Res 2006;47:67–77.
  • Grove KA, Lambert JD. Laboratory, epidemiological, and human intervention studies show that tea (Camellia sinensis) may be useful in the prevention of obesity. J Nutr 2010; 140:446–453.
  • Siddiqui IA, Zaman N, Aziz MH, Reagan-Shaw SR, Sarfaraz S, Adhami VM, Ahmad N, Raisuddin S, Mukhtar H. Inhibition of CWR22R 1 tumor growth and PSA secretion in athymic nude mice by green and black teas. Carcinogenesis 2006;27:833–839.
  • Chen X, Sun CK, Han GZ, Peng JY, Li Y, Liu YX, Lv YY, Liu KX, Zhou Q, Sun HJ. Protective effect of tea polyphenols against paracetamol-induced hepatotoxicity in mice is significantly correlated with cytochrome P450 suppression. World J Gastroenterol 2009;15:1829–1835.
  • Srinivasan P, Suchalatha S, Babu PV, Devi RS, Narayan S, Sabitha KE, Shyamala CS. Chemopreventive and therapeutic modulation of green tea polyphenols on drug metabolizing enzymes in 4-nitroquinoline 1-oxide induced oral cancer. Chem Biol Int 2008;172:224–234.
  • Klaunig JE, Kamendulis LM, Hocevar BA. Oxidative stress and oxidative damage in carcinogenesis. Toxicol Pathol 2010;38:96–109.
  • Díaz de la Loza MC, Wellinger RE. A novel approach for organelle-specific DNA damage targeting reveals different susceptibility of mitochondrial DNA to the anticancer drugs camptothecin and topotecan. Nucleic Acids Res 2009; 37:e26.
  • Feng Q, Torii Y, Uchida K, Nakamura Y, Hara Y, Osawa T. Black tea polyphenols, theaflavins, prevent cellular DNA damage by inhibiting oxidative stress and suppressing cytochrome P450 1A1 in cell cultures. J Agric Food Chem 2002;50:213–220.
  • Weisburger JH, Chung FL. Mechanisms of chronic disease causation by nutritional factors and tobacco products and their prevention by tea polyphenols. Food Chem Toxicol 2002;40:1145–1154.
  • Aktas O, Prozorovski T, Smorodchenko A, Savaskan NE, Lauster R, Kloetzel PM, Infante-Duarte C, Brocke S, Zipp F. Green tea epigallocatechin-3-gallate mediates T cellular NF-kappa B inhibition and exerts neuroprotection in autoimmune encephalomyelitis. J Immunol 2004;173:5794–5800.
  • Shimizu M, Deguchi A, Lim JTE, Moriwaki H, Kopelovich L, Weinstein IB. (–)-Epigallocatechin gallate and Polyphenon E inhibit growth and activation of the epidermal growth factor receptor and human epidermal growth factor receptor-2 signaling pathways in human colon cancer cells. Clin Cancer Res 2005;11:2735–2746.
  • Kobayashi H, Tanaka Y, Asagiri K, Asakawa T, Tanikawa K, Kage M, Yagi M. The antioxidant effect of green tea catechin ameliorates experimental liver injury. Phytomedicine 2010; 17:197202.
  • Guo W, Wise ML, Collins FW, Meydani M. Avenanthramides, polyphenols from oats, inhibit IL-1beta-induced NF-kappaB activation in endothelial cells. Free Radic Biol Med 2008;44:415–429.
  • Lambert JD, Hong J, Yang G, Liao J, Yang CS. Inhibition of carcinogenesis by polyphenols: evidence from laboratory investigations. Am J Clin Nutr 2005;81:284S–291S.
  • Zykova TA, Zhang Y, Zhu F, Bode AM, Dong Z. The signal transduction networks required for phosphorylation of STAT1 at Ser727 in mouse epidermal JB6 cells in the UVB response and inhibitory mechanisms of tea polyphenols. Carcinogenesis 2005;26:331–342.
  • Tu Y, Tang A, Watanabe N. The theaflavin monomers inhibit the cancer cells growth in vitro. Acta Biochim Biophys Sin 2004;36:508–512.
  • Ravindranath MH, Saravanan TS, Monteclaro CC, Presser N, Ye X, Selvan SR, Brosman S. Epicatechins purified from green tea (Camellia sinensis) differentially suppress growth of gender-dependent human cancer cell lines. Evid Based Complement Altern Med 2006;3:237–247.
  • Ostrowska J, Skrzydlewska E. The comparison of effect of catechins and green tea extract on oxidative modification of LDL in vitro. Adv Med Sci 2006;51:298–303.
  • Skrzydlewska E, Ostrowska J, Stankiewicz A, Farbiszewski R. Green tea as a potent antioxidant in alcohol intoxication. Addict Biol 2002;7:307–314.
  • Oikawa S, Furukawa A, Asada H, Hirakawa K, Kawanishi S. Catechins induced oxidative damage to cellular and isolated DNA through the generation of reactive oxygen species. Free Radic Biol Med 2003;37:881–890.
  • Babich H, Gottesman RT, Liebling EJ, Schuck AG. Theaflavin- 3-gallate and theaflavin-3’-gallate, polyphenols in black tea with prooxidant properties. Basic Clin Pharmacol Toxicol 2008;103:66–74.
  • Il'yasova D, Arab L, Martinchik A, Sdvizhkov A, Urbanovich L, Weisgerber U. Black tea consumption and the risk of rectal cancer in Moscow population. Ann Epidemiol 2003;13: 405–411.
  • Il'yasova D, Martin C, Sandler RS. Tea intake and risk of cancer in African-Americans and whites: North Carolina colon cancer study. Cancer Causes Contr 2003;14:767–772.
  • Tan LC, Venketasubramanian N, Jamora RD, Heng D. Incidence of Parkinson's disease in Singapore. Parkinsonism Relat Disord 2007;13:40–43.
  • Kuriyama S. The relation between green tea consumption and cardiovascular disease as evidenced by epidemiologica. J Nutr 2008;138:1548–1553.
  • Cabrera C, Artacho R, Giménez R. Beneficial effects of green tea - a review. J Am Coll Nutr 2006;25:79–99.
  • Mandel SA, Amit T, Kalfon L, Reznichenko L, Youdim MBH. Targeting multiple neurodegenerative diseases etiologies with multimodal-acting green tea catechins. J Nutr 2008;138:1578–1583.
  • Mennen L, Saphino D, de Bree A, Arnault N, Bertrais S, Galan P, Hercberg S. Consumption of foods rich in flavonoids is related to a decreased cardiovascular risk in apparently healthy French women. J Nutr 2004;134:923–926.
  • Wang QM, Gong QY, Yan JJ, Zhu J, Tang JJ, Wang MW, Yang ZJ, Wang LS. Association between green tea intake and coronary artery disease in a Chinese population. Circ J 2010;74:294–300.
  • Kuriyama S, Shimazu T, Ohmori K, Kikuchi N, Nakaya N, Nishino Y, Tsubono Y, Tsuji I. Green tea consumption and mortality due to cardiovascular disease, cancer, and all causes in Japan: The Ohsaki Study. JAMA 2006;296: 1255–1265.
  • Sharma V, Rao LJ. A thought on the biological activities of black tea. Crit Rev Food Sci Nutr 2009;49:379–404.
  • Clement Y. Can green tea do that? A literature review of the clinical evidence. Prev Med 2009;49:83–87.
  • Zhong L, Goldberg MS, Gao YT, Hanley JA, Parent ME, Jin F. A population-based case-control study of lung cancer and green tea consumption among women living in Shanghai, China. Epidemiology 2001;12:695–700.
  • Inoue M, Tajima K, Mizutani M, Iwata H, Iwase T, Miura S, Hirose K, Hamajima N, Tominaga S. Regular consumption of green tea and the risk of breast cancer recurrence: follow-up study from the Hospital-based Epidemiologic Research Program at Aichi Cancer Center (HERPACC). Japan Cancer Lett 2001;167:175–182.
  • Wu AH, Yu MC, Tseng CC, Hankin J, Pike MC. Green tea and risk of breast cancer in Asian Americans. Int J Cancer 2003;106:574–579.
  • Zhang M, Binns CW, Lee AH. Tea consumption and ovarian cancer risk: a case-control study in China. Cancer Epidemiol Biomarkers Prev 2002;11:713–718.
  • Jian L, Xie LP, Lee AH, Binns CW. Protective effect of green tea against prostate cancer: a case-control study in southeast China. Int J Cancer 2004;108:130–135.
  • Ruhul Amin ARM, Khuri FR, Chen Z, Shin DM. Synergistic growth inhibition of squamous cell carcinoma of the head and neck by erlotinib and epigallocatechin-3-gallate: the role of p53-dependent inhibition of nuclear factor-kB. Cancer Prev Res 2009;2:538–545.
  • Kogure K, Hama S, Kisaki M, Takemasa H, Tokumura A, Suzuki I, Fukuzawa K. Structural characteristic of terminal dicarboxylic moiety required for apoptogenic activity of alpha-tocopheryl esters. Biochim Biophys Acta 2004;1672: 93–99.
  • Weber T, Dalen H, Andera L, Negre-Salvayre A, Auge N, Sticha M, Lloret A, Terman A, Witting PK, Higuchi M, Plasilova M, Zivny J, Gellert N, Weber C, Neuzil J. Mitochondria play a central role in apoptosis induced by alpha-tocopheryl succinate, an agent with antineoplastic activity: comparison with receptor-mediated pro-apoptotic signaling. Biochemistry 2003;42:4277–4291.
  • Pussinen PJ, Lindner H, Glatter O, Reicher H, Kostner GM, Wintersperger A, Malle E, Sattler W. Lipoprotein-associated alpha-tocopheryl-succinate inhibits cell growth and induces apoptosis in human MCF-7 and HBL-100 breast cancer cells. Biochim Biophys Acta 2000;1485:129–144.
  • Neuzil J, Weber T, Schroder A, Lu M, Ostermann G, Gellert N, Mayne GC, Olejnicka B, Negre-Salvayre A, Sticha M, Coffey RJ, Weber C. Induction of cancer cell apoptosis by alpha-tocopheryl succinate: molecular pathways and structural requirements. FASEB J 2001;15:403.
  • Weber T, Lu M, Andera L, Lahm H, Gellert N, Fariss MW, Korinek V, Sattler W, Ucker DS, Terman A, Schroder A, Erl W, Brunk UT, Coffey RJ, Weber C, Neuzil J. Vitamin E succinate is a potent novel antineoplastic agent with high selectivity and cooperativity with tumor necrosis factor-related apoptosis-inducing ligand (Apo2 ligand) in vivo. Clin Cancer Res 2002;8:863–869.
  • Israel K, Sanders BG, Kline K. RRR-alpha-tocopheryl succinate inhibits the proliferation of human prostatic tumor cells with defective cell cycle/differentiation pathways. Nutr Cancer 1995;24:161–169.
  • Birringer M, EyTina JH, Salvadore BA, Neuzil J. Vitamin E analogues as inducers of apoptosis: structure-function relation. Br J Cancer 2003;88:1948–1955.
  • Neuzil J, Tomasetti M, Mellick AS, Alleva R, Salvatore BA, Birringer M, Fariss MW. Vitamin E analogues: a new class of inducers of apoptosis with selective anti-cancer effects. Curr Canc Drug Targ 2004;4:355–372.
  • Zhao Y, Neuzil J, Wu K. Vitamin E analogues as mitochondria-targeting compounds: from the betch to the bedside? Mol Nutr Food Res 2009;53:129–139.
  • Yu W, Liao QY, Hantash FM, Sanders BG, Kline K. Activation of extracellular signal-regulated kinase and c-Jun-NH(2)-terminal kinase but not p38 mitogen-activated protein kinases is required for RRR-alpha-tocopheryl succinate-induced apoptosis of human breast cancer cells. Cancer Res 2001;61:6569–6576.
  • Turley JM, Fu T, Ruscetti FW, Mikovits JA, Bertolette DCR, Birchenall-Roberts MC. Vitamin E succinate induces Fas-mediated apoptosis in estrogen receptor-negative human breast cancer cells. Cancer Res 1997;57:881–890.
  • You H, Yu W, Munoz-Medellin D, Brown P, Birrer MJ, Sanders BG, Kline K. Role of extracellular signal-regulated kinase pathway in RRR-alpha-tocopheryl succinate-induced differentiation of human MDA-MB-435 breast cancer cells. Mol Carcinogen 2002;33:228–236.
  • Tomasetti M, Andera L, Alleva R, Borghi B, Neuzil J, Procopio A. Alpha-tocopheryl succinate induces DR4 and DR5 expression by a p53-dependent route: implication for sensitisation of resistant cancer cells to TRAIL apoptosis. FEBS Lett 2006;580:1925–1931.
  • Campbell SE, Stone WL, Whaley S, Yang H, Qui M, Goforth P, Sherman D, Hchaffie D, Krishnan K. Comparative effects of RRR-alpha- and RRR-gamma-tocopherol on proliferation and apoptosis in human colon cancer cell lines. BMC Cancer 2006;6:13–26.
  • Malafa MP, Fokum FFD, Andoh J, Neitzel LT, Bandyopadhyay S, Zhan R, Iiizumi M, Furuta E, Horvath E, Watabe K. Vitamin E succinate suppresses prostate tumor growth by inducing apoptosis. Int J Cancer 2006;118: 2441–2447.
  • Zu K, Hawthorn L, Ip C. Up-regulation of c-Jun-NH2-kinase pathway contributes to the induction of mitochondria-mediated apoptosis by alpha-tocopheryl succinate in human prostate cancer cells. Mol Cancer Ther 2005;4: 43–50.
  • Yu W, Sanders BG, Kline K. RRR-alpha-tocopheryl succinate-induced apoptosis of human breast cancer cells involves Bax translocation to mitochondria. Cancer Res 2003;63:2483–2491.
  • Shiau CW, Huang JWDS, Weng JR, Yang CC, Lin C, Chen CS. Alpha-Tocopheryl succinate induces apoptosis in prostate cancer cells in part through inhibition of Bcl-xL/Bcl-2 function. J Biol Chem 2006;281:11819–11825.
  • Neuzil J, Wang XF, Dong LF, Low P, Ralph SJ. Molecular mechanism of ‘mitocan’-induced apoptosis in cancer cells epitomizes the multiple roles of reactive oxygen species and Bcl-2 family proteins. FEBS Lett 2006;580:5125–5129.
  • Zhao Y, Wu K, Xia W, Ahan YJ, Wu LJ, Yu WP. The effects of vitamin E succinate on the expression of c-jun gene and protein in human gastric cancer SGC-7901 cells. World J Gastoenterol 2002;8:782–786.
  • Donapaty S, Louis S, Horvath E, Kun J, Sebti SM, Malafa M. RRR-alpha-tocopherol succinate down-regulates oncogenic Ras signaling. Mol Cancer Ther 2006;5:309–316.
  • Dalen H, Neuzil J. α-Tocopheryl succinate sensitizes a T lymphoma cell line to TRAIL-induced apoptosis by suppressing NF-κB activation. Br J Cancer 2003;88:153–158.
  • Constantinou C, Hyatt JA, Vraka PS, Papas A, Papas KA, Neophytou C, Hadjivassiliou V, Constantinou AI. Induction of caspase-independent programmed cell death by vitamin E natural homologs and synthetic derivatives. Nutr Cancer 2009;61:864–874.
  • Zhang M, Altuwaijri S, Yeh S. RRR-alpha-tocopheryl succinate inhibits human prostate cancer cell invasiveness. Oncogene 2004;23:3080–3088.
  • Chinery R, Brockman JA, Peeler MO, Shyr Y, Beauchamp RD, Coffey RJ. Antioxidants enhance the cytotoxicity of chemotherapeutic agents in colorectal cancer: a p53- independent induction of p21WAF1/CIP1 via C/EBPbeta. Nat Med 1997;3:1233–1241.
  • Arya P, Alivia N, Qin H, Burton GW, Batist G, You SX, Alaoui-Jamali MA. Design and synthesis of analogs of vitamin E: antiproliferative activity against human breast adenocarcinoma cells. Bioorg Med Chem Lett 1998;8: 2433–1241.
  • Vraka PS, Drouza C, Rikkou MP, Odysseos AD, Keramidas AD. Synthesis and study of the cancer cell growth inhibitory properties of alpha-, gamma-tocopheryl and gamma- tocotrienyl 2-phenylselenyl succinates. Bioorg Med Chem 2006;14:2684–2696.
  • El-Bayoumy K. The protective role of selenium on genetic damage and on cancer. Mutat Res 2001;475:123–139.
  • Ip C, El-Bayoumy K, Upadhyaya P, Ganther H, Vadhanavikit S, Thompson H. Comparative effect of inorganic and organic selenocyanate derivatives in mammary cancer chemoprevention. Carcinogenesis 1994;15:187–192.
  • Ip C. Lessons from basic research in selenium and cancer prevention. J Nutr 1998;128:1845–1854.
  • Redman C, Scott JA, Baines AT, Basyc JL, Clark LC, Calley C, Roe D, Payne CM. Inhibitory effect of selenomethionine on the growth of three selected human tumor cell lines. Cancer Lett 1998;125:103–110.
  • Jiang C, Wang Z, Ganther H, Lu J. Distinct effects of methylseleninic acid versus selenite on apoptosis, cell cycle, and protein kinase pathways in DU145 human prostate cancer cells. Molec Cancer Ther 2002;1:1059–1066.
  • Ip C, Dong Y, Ganther H. New concepts in selenium chemoprevention. Cancer Metastasis Rev 2002;21:281–289.
  • Jiang C, Hu H, Malewicz B, Wang Z, Lu J. Selenite-induced p53 Ser-15 phosphorylation and caspase-mediated apoptosis in LNCaP human prostate cancer cells. Mol Cancer Ther 2004;3:877–884.
  • Tsukagoshi H, Koketsu M, Kato M, Kurabayashi M, Nishina A, Kimura H. Superoxide radical-scavenging effects from polymorphonuclear leukocytes and toxicity in human cell lines of newly synthesized organic selenium compounds. FEBS J 2007;274:6046–6054.
  • Zu K, Ip C. Synergy between selenium and vitamin E in apoptosis induction is associated with activation of distinctive initiator caspases in human prostate cancer cells. Cancer Res 2003;63:6988–6995.
  • Day BJ. Antioxidants as potential therapeutics for lung fibrosis. Antioxid Redox Signal 2008;10:355–370.
  • Esposito E, Cuzzocrea S. Role of nitroso radicals as drug targets in circulatory shock. Br J Pharmacol 2009;157:494–508.
  • Chatterjee PK. EUK-134 reduces renal dysfunction and injury caused by oxidative and nitrosative stress of the kidney. Am J Nephrol 2004;24:165–177.
  • Pandolfo M. Drug Insight: antioxidant therapy in inherited ataxias. Nature Clin Pract Neurology 2008;4:86–96.
  • Kavanagh RJ, Kam PC. Lazaroids: efficacy and mechanism of action of the 21-aminosteroids in neuroprotection. Br J Anaesth 2001;86:110–119.
  • Aruoma OI. Methodological considerations for characterizing potential antioxidant actions of bioactive components in plant foods. Mutat Res 2003;523–524:9–20.
  • Süzen S. Antioxidant activities of synthetic indole derivatives and possible activity mechanisms. Top Heterocycl Chem 2007;11:145–178.
  • Stefek M, Benes L. Pyridoindole stobadine is a potent scavenger of hydroxyl radicals. FEBS Lett 1991;294:264–266.
  • Steenken S, Sunquist AR, Jovanovic SV, Crockett R, Sies H. Antioxidant activity of the pyridoindole stobadine. Pulse radiolytic characterization of one-electron-oxidized stobadine and quenching of singlet molecular oxygen. Chem Res Toxicol 1992;5:355–360.
  • Kagan VE, Tsuchiya M, Serbinova E, Packer L, Sies H. Interaction of the pyridoindole stobadine with peroxyl, superoxide and chromanoxyl radicals. Biochem Pharmacol 1993;45:393–400.
  • Horakova K, Sies H, Steenken S. Antioxidant action of stobadine. Methods Enzymol. 1994;234:572–580.
  • Stolc S, Vlkolinsky R, Pavlasek J. Neuroprotection by the pyridoindole stobadine: a minireview. Brain Res Bull 1997; 42:335–340.
  • Horakova L, Stolc S. Antioxidant and pharmacodynamic effects of pyridoindole stobadine. Gen Pharmacol 1998;30: 627–638.
  • Juranek I, Horakova L, Rackova L, Stefek M. Antioxidants in treating pathologies involving oxidative damage: an update on medicinal chemistry and biological activity of stobadine and related pyridoindoles. Curr Med Chem 2010;17: 552–570.
  • Barclay LRC, Vinqvist MR. Membrane peroxidation: inhibiting effects of watersoluble antioxidants on phospholipids of different charge types. Free Radic Biol Med 1994;16: 779–788.
  • Stefek M, Benes L, Zelník V. N-oxygenation of stobadine, a gamma-carboline antiarrhythmic and cardioprotective agent: the role of flavin-containing monooxygenase. Xenobiotica 1989;19:143–150.
  • Barclay LR, Artz JD, Mowat JJ. Partitioning and antioxidant action of the water-soluble antioxidant, Trolox, between the aqueous and lipid phases of phosphatidylcholine membranes: 14C tracer and product studies. Biochim Biophys Acta 1995;1237:77–85.
  • Stefek M, Snirc V, Djoubissie P-O, Majekova M, Demopoulos V, Rackova L, Bezakova Z, Karasu C, Carbone V, El-Kabbani O. Carboxymethylated pyridoindole antioxidants as aldose reductase inhibitors: synthesis, activity, partitioning, and molecular modelling. Bioorg Med Chem 2008;16:4908–4920.
  • Rackova L, Majekova M, Kostalova D, Stefek M. Antiradical and antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects. Bioorg Med Chem 2004;12: 4709–4715.
  • Rackova L, Stefek M, Majekova M. Structural aspects of antioxidant activity of substituted pyridoindoles. Redox Rep 2002;7:207–214.
  • Juskova M, Snirc V, Krizanova L, Stefek M. Effect of carboxymethylated pyridoindoles on free radical-induced haemolysis of rat erythrocytes in vitro. Acta Biochim Pol 2010;57:153–156.
  • Horakova L, Licht A, Sandig G, Jakstadt M, Durackova Z, Grune T. Standardized extracts of flavonoids increase the viability of PC12 cells treated with hydrogen peroxide: effects on oxidative injury. Arch Toxicol 2003;77:22–29.
  • Davies MJ, Fornit LG, Willson RL. Vitamin E analogue Trolox: C E.S.R. And pulse-radiolysis studies of free-radical reactions. Biochem J 1988;255:513–522.
  • Svanholm U, Beckgaard K, Parker VD. Electrochemistry in media of intermediate activity. VIII. Reversible oxidation products of α-tocopherol model compound. Cation radical, cation, and dication. J Am Chem Soc 1974;96:2409–2413.
  • Musialik M. Scavenging of dpph• radicals by Vitamin E is accelerated by its partial ionization: the role of sequential proton loss electron transfer. Org Lett 2005;7:4951–4954.
  • Nishikimi M, Machlin LJ. Oxidation of alpha-tocopherol model compound by superoxide anion. Arch Biochem Biophys 1975;170:684–689.
  • Bielski BHJ. Evaluation of the reactivities of HO2./O2−. with compounds of biological interest. Cohen G, Greenwald RE. Oxy radicals and their scavenger systems. Amsterdam: Elsevier; 1982. 1–7.
  • Aruoma OI, Evans PJ, Kaur H, Sutcliffe L, Halliwell B. An evaluation of the antioxidant and potential pro-oxidant properties of food additives and of Trolox C,vitamin E and probucol. Free Radic Res Commun 1990;10:143–157.
  • Kyselova Z, Rackova L, Stefek M. Pyridoindole antioxidant stobadine protected bovine serum albumin against the hydroxyl radical mediated cross-linking in vitro. Arch Gerontol Geriatr 2003;36:221–229.
  • Horakova L, Briviba K, Sies H. Antioxidant activity of the pyridoindole stobadine in liposomal and microsomal lipid peroxidation. Chem Biol Interact 1992;83:85–93.
  • Neta P, Steenken S. One electron redox potentials of phenols, hydroxy- and aminophenols and related compounds of biological interest. J Phys Chem 1982;86:3661–3667.
  • Stefek M, Kyselova Z, Rackova L, Krizanova L. Oxidative modification of rat lens proteins by peroxyl radicals in vitro: protection by the chain-breaking antioxidants Stobadine and Trolox. Biochim Biophys Acta 2005;1741:183–190.
  • Stefek M, Krizanova L, Trnkova Z. Oxidative modification of serum albumin in an experimental glycation model of diabetes mellitus in vitro: effect of the pyridoindole antioxidant stobadine. Life Sci 1999;65:1995–1997.
  • Rackova L, Snirc V, Majekova M, Majek P, Stefek M. Free radical scavenging and antioxidant activities of substituted hexahydropyridoindoles.quantitative structure-activity relationships. J Med Chem 2006;49:2543–2548.
  • Horakova L, Giessauf A, Raber G, Esterbauer H. Effect of stobadine on Cu (++)-mediated oxidation of low-density lipoprotein. Biochem Pharmacol 1996;51:1277–1282.
  • Horáková L, Ondrejicková O, Bachratá K, Vajdová M. Preventive effect of several antioxidants after oxidative stress on rat brain homogenates. Gen Physiol Biophys 2000;19: 195–205.
  • Stefek M, Trnkova Z. The pyridoindole antioxidant stobadine prevents alloxan-induced lipid peroxidation by inhibiting its propagation. Pharmacol Toxicol 1996;78:77–81.
  • Štefek M, Šnirc V, Djoubissie PO, Májeková M, Demopoulos V, Račková L, Bezáková Z, Karasu Ç, Carbone V, El-Kabbani O. Carboxymethylated pyridoindole antioxidants as aldose reductase inhibitors: synthesis; activity; partitioning; and molecular modeling. Bioorgan Med Chem 2008;16:4908–4920.
  • Spartan`08. Irvine, CA: Wavefunction; Inc.; 2009.
  • Duburs G, Vigante B, Plotniece A, Krauze A, Sobolevs A, Briede J, Kluša V, Velána A. Dihydropyridine derivatives as bioprotectors. Chem Today 2008;26:68–70.
  • Giller SA, Dubur GY, Uldrikis YR, Tirzit GD, Valdman AR, Zakharchenko IM, Spruz YY, Ronis VY, Makarov AA. Improvements in or relating to the stabilization of carotene. UK Patent. 1 294 650. 1970.
  • Kourimska L, Pokorny J, Tirzitis G. The antioxidant activity of 2,6-dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridine in edible oils. Nahrung 1993;37:91–93.
  • Abdalla AE, Tirzite D, Tirzitis G, Roozen JP. Antioxidant activity of 1,4-dihydropyridien derivatives in ß-carotene-methyl linoleate, sunflower oil and emulsions. Food Chem 1999;66:189–195.
  • Tirzit GD, Dubur GJ. [1,4-Dihydropyridines - inhibitors of free radical reactions]. Khim Geterotsikl Soed 1972;8: 133–134.
  • Tirzitis G, Kirule I, Duburs G. Antioxidationsaktivität der 3,5-Dicarbonylderivative des 2,6-Dimethyl-1,4-dihydropyridins. Fat Sci Technol 1988;90:411–413.
  • Duburs G, Zilbers JA, Velena A, Kumerova AO, Tirzitis GD. [Multistage studies of control of peroxidation processes in biological membranes with antioxidants of 1,4-dihydropyridine series]. Izv AN Latv SSR 1975;7:65–68
  • Dubur GJ, Velena AH, Gurasov BM, Vladimirov JA. [Regulation of peroxidation of mitochondrial membrane lipids initiated by Fe2+ ions by 1,4-dihydropyridine antioxidants in vitro]. Vopr Med Khimii 1976;22:665–672.
  • Dubur GJ. 1,4-Dihydropyridines, their reaction possibilities and biological properties. Riga: Latvian University; 1978.
  • Tirzitis GD, Kirule IE, Dubur GY. Antioxidant activity of some 1,4-dihydropyridine and 1,4-dihydroindeno[1,2-b]pyridine derivatives and their action as α-tocopherol synergists. Proc 16th World Congr Int Soc Fat Res, Budapest: ; 1983; 655–661.
  • Tirzit GD, Byteva IM, Salokhiddinov KI, Gurinovich GP, Dubur GYa. Derivatives of 1,4-dihydropyridine as deactivators of singlet oxygen. Chem Heterocycl Comp 1981;17:924–926.
  • Tirzit GD, Byteva IM, Salokhiddinov KI, Gurinovich GP, Dubur GY. Derivatives of 1,4-dihydropyridine as deactivators of singlet oxygen. Chem Heterocycl Comp 1981;17:924–926.
  • Tirzite D, Tirzitis G, Antipova D. Reductive ability of 1,4-dihydropyridine derivatives in relation to ions of trivalent iron. Chem Heterocycl Comp 1999;35:592–594.
  • Borovic S, Tirzitis G, Tirzite D, Cipak A, Khoschsorur GW, Tatzber F, Scukanec-Spoljar M, Zarkovic N. Bioactive 1,4-dihydroisonicotinic acid derivatives prevent oxidative damage of liver cells. Eur J Pharmacol 2006;637:12–19.
  • Tirzitis G, Tirzite D, Hyvonen Z. Antioxidant activity of 2,6-dimethyl-3,5-dialkoxycarbonyl-1,4-dihydropyridines in metal-ion catalyzed lipid peroxidation. Czech J Food Sci 2001;19:81–84.
  • Panasenko OM, Tirzite DJ, Tirzitis GD, Duburs GJ. Effect of some 1,4-dihydropyridine derivatives on structural organization of erythrocyte membranes. Biol Membr (Moscow) 1984;9:919–925.
  • Yáñez C, López-Alarcón C, Camargo C, Valenzuela V, Squella JA, Núñez-Vergara LJ. Structural effects of reactivity 1,4-dihydropyridines with alkylperoxyl radicals and ABTS radical cation. Bioorg Med Chem 2004;12:2459–2468.
  • Mulder P, Litwinienko G, Lin SD, McLean P, Barclay LRC, Ingold KU. The L-type calcium channel blockers, Hantzsch 1,4-dihydropyridines, are not peroxyl radical-trapping, chain-breaking antioxidants. Chem Res Toxicol 2006;19: 79–85.
  • Kirule IE, Rubene DJ, Bisenieks EA, Tirzit GD, Dubur GJ. [4-Nitrophenyl-1,4-dihydropyridines - a new group of inhibitors of peroxide oxidation]. Khim Geterotsikl Soed 1982; 18:416–417.
  • Tirzit GD, Kirule IE, Baumane LK, Gavar RA, Stradin JP, Dubur GY. [Mechanism of the antioxidant action of 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(2-nitrophenyl)- 1,4-dihydropyridine]. Khim Geterotsikl Soed 1984;20: 1120–1122.
  • Misík V, Stasko A, Gergel D, Ondrias K. Spin-trapping and antioxidant properties of illuminated and nonilluminated nifedipine and nimodipine in heart homogenate and model system. Mol Pharmacol 1991;40:435–439.
  • Ondrias K, Misík V, Stasko A, Gergel D, Hromadová M. Comparison of antioxidant properties of nifedipine and illuminated nifedipine with nitroso spin traps in low density lipoproteins and phosphatidylcholine liposomes. Biochim Biophys Acta 1994;1211:114–119.
  • Rojstaczer N, Triggle DJ. Structure-function relationships of calcium antagonists. Effect on oxidative modification of low density lipoprotein. Biochem Pharmacol 1996;51:141–150.
  • Rosenkranz AC, Lob H, Breitenbach T, Berkels R, Roesen R. Endothelial antioxidant actions of dihydropyridines and angiotensin converting enzyme inhibitors. Eur J Pharmacol 2006;529:55–62.
  • Letelier ME, Entrala P, López-Alarcón C, González-Lira V, Molina-Berríos A, Cortés-Troncoso J, Jara-Sandoval J, Santander P, Núñez-Vergara LJ. Nitroaryl-1,4-dihydropyridines as antioxidants against rat liver microsomes oxidation induced by iron/ascorbate, nitrofurantoin and naphthalene. Toxicol In Vitro 2007;21:1610–1618.
  • Fernandes MA, Santos MS, Moreno AJ, Chernova L, Krauze A, Duburs G, Vicente JA. Effects of 5-acetyl(carbamoyl)-6-methylsulfanyl-1,4-dihydropyridine-5-carbonitriles on rat liver mitochondrial function. Toxicol In Vitro 2009;23:1333–1341.
  • Levy L. The anti-inflammatory action of some compounds with antioxidant properties. Inflammation 1976;1:333–345.
  • Matsumori A, Ono K, Nishio R, Nose Y, Sasayama S. Amlodipine inhibits the production of cytokines induced by ouabain. Cytokine 2000;12:294–297.
  • Yuan Z, Kishimoto C, Shioji K. Beneficial effects of low-dose benidipine in aorta myocarditis: suppressive effects on inflammatory cytokines and inducible nitric oxide synthase. Circ J 2003;67:545–550.
  • Hishikawa K, Lüscher TF. Felodipine inhibits free-radical production by cytokines and glucose in human smooth muscle cells. Hypertension 1998;32:1011–1015.
  • Klegeris A, Liutkevicius E, Mikalauskiene G, Duburs G, McGeer PL, Klusa V. Anti-inflammatory effects of cerebrocrast in a model of rat paw edema and on mononuclear THP-1 cells. Eur J Pharmacol 2002;441:203–208.
  • Briede J, Daija D, Stivrina M, Duburs G. Effect of cerebrocrast on the lymphocyte blast transformation activity in normal and streptozotocin-induced diabetic rats. Cell Biochem Funct 1999;17:89–96.
  • Fukuo K, Yang J, Suzuki T, Kaimoto T, Takemura Y, Yasuda O, Suhara T, Sato N, Ogihara T. Nifedipine upregulates manganese superoxide dismutase expression in vascular smooth muscle cells via endothelial cell-dependent pathways. Hypertens Res 2003;26:503–508.
  • Cominacini L, Fratta Pasini A, Garbin U, Pastorino AM, Davoli A, Nava C, Campagnola M, Rossato P, Lo Cascio V. Antioxidant activity of different dihydropyridines. Biochem Biophys Res Commun 2003;302:679–684.
  • Klimavicčiusa L, Kalda A, Kaasik A, Zarkovsky A, Bisenieks E, Uldriķis J, Duburs G, Kluša V. Neuroprotective activity of 1,4-dihydropyridine derivatives: structure determinants. Proc Latv Acad Sci B 2007;61:33–37.
  • Ryabokon NI, Goncharova RI, Duburs G, Hancock R, Rzeszowska-Wolny J. Changes in poly(ADP-ribose) level modulate the kinetics of DNA strand break rejoining. Mutat Res 2008;637:173–181.
  • Goncharova RI, Kuzhir TD, Levina AB, Dubur GJ. [Anti-mutagenic activity of several dihydropyridines]. Dokl Akad Nauk BSSR 1974;18:167–168.
  • Wojewódzka M, Gradzka I, Buraczewska I, Brzóska K, Sochanowicz B, Goncharova R, Kuzhir T, Szumiel I. Dihydropyridines decrease X-ray-induced DNA base damage in mammalian cells. Mutat Res 2009;671:45–51.
  • Ryabokon NI, Nikitchenko NV, Dalivelya OV, Goncharova RI, Duburs G, Konopacka M, Rzeszowska-Wolny J. Modulation of cellular defense processes in human lymphocytes in vitro by a 1,4-dihydropyridine derivative. Mutat Res 2009;679:33–83.
  • East JM. Sarco(endo)plasmic reticulum calcium pumps: recent advances in our understanding of structure/function and biology (review). Mol Membr Biol 2000;17:189–200.
  • Starling AP, East JM, Lee AG. Stimulation of the Ca2+ATPase of the sarcoplasmic reticulum by disulfiram. Biochem J 1996;320:101–105.
  • Dremina ES, Sharov VS, Schoneich C. Displacement of SERCA from SR lipid caveolae-related domains by Bcl-2: a possible mechanism for SERCA inactivation. Biochemistry 2006;45:175–184.
  • Sharov VS, Dremina ES, Galeva NA, Williams TD, Schöneich C. Quantitative mapping of oxidation-sensitive cysteine residues in SERCA in vivo and in vitro by HPLC-electrospraytandem MS: selective protein oxidation during biological aging. Biochem J 2006;394:605–615.
  • Fusi F, Tzankova V, Valoti M, Pessina F, Sgaragli G. 3,5-di-t-butyl-4-hydroxyanisole (DTBHA) activation of rat skeletal muscle sarcoplasmic reticulum Ca2+-ATPase. Biochem Pharmacol 2001;62:1613–1619.
  • Štrosová M, Karlovská J, Balgavý P, Horáková L. Effect of some antioxidants on sarcoplasmic reticulum Ca2+-ATPase activity from rabbit skeletal muscle. Neuro Endocrinol Lett 2006;27(Suppl 2):164–167.
  • Štolc S, Bauer V, Beneš L, Tichý M. Medicine with antiarrhythmic and antihypoxic activity and its method of preparation. Patents: CS 229067, SWED 8204693-9, BELG 894148, SWISS 651 754, BRD P-323 1088, SPAIN 553 017, JAP 151 4040 1983.
  • Štolc S, Považanec F, Bauer V, Májeková M, Willcox AL, Šnirc V, Račková L, Sotníková R, Štefek M, Gáspárová Z, Gajdošíková A, Mihalová D, Alföldi J. Pyridoindolové deriváty s antioxidančnými vlastnosťami, spôsob ich prípravy a použitie v liečebnej praxi. Slovak Patent Application 1321–2003 2003.
  • Štefek M, Šnirc V, Demopoulos VJ, Djoubissie P-O, Račková L, Májeková M, Karasu Ç. Použitie karboxy-metylovaných pyridoindolov a farmaceutický prostriedok, ktorý ich obsahuje. Patent: SLOVAK 286958 2009.
  • Rackova L. Structure-activity relationships of the pyridoindole antioxidants. PhD Thesis, Institute of Experimental Pharmacology and Toxicology, Slovak Academy of Sciences, Bratislava Slovakia. 2002.
  • Rohdewald P. A review of the French maritime pine bark extract (Pycnogenol®), a herbal medication with a diverse clinical pharmacology. Int J Clin Pharmacol Ther 2002;40: 158-168.
  • Bilmen JG, Khan ZS, Javed M-H, Michelangeli F. Inhibition of the SERCA Ca2+ pumps by curcumin. Eur J Biochem 2001;268:6318–6327.
  • Kelloff GJ, Boone CW, Crowell JA, Steele VE, Lubet RA, Doody LA, Malone WF, Hawk ET, Sigman CC. New agents for cancer chemoprevention. J Cell Biochem 1996;26: 1–28.
  • Piwocka K, Zablocki K, Wieckowski MR, Skierski J, Feiga I, Szopa J, Drela N, Wojtczak L, Sikora E. A novel apoptosis-like pathway, independent of mitochondria and caspases, induced by curcumin in human lymphoblastoid T (Jurkat) cells. Exp Cell Res 1999;249:299–307.
  • Shah BH, Nawaz Z, Pertani SA, Roomi A, Mahmood H, Saeed SA, Gilani AH. Inhibitory effect of curcumin, a food spice from turmeric, on platelet-activating factor- and arachidonic acid-mediated platelet aggregation through inhibition of thromboxane formation and Ca2+ signaling. Biochem Pharmacol 1999;58:1167–1172.
  • Orrenius S, McConkey DJ, Nicotera P. Role of calcium in toxic and programmed cell death. Adv Exp MedBiol 1991; 283:419–425.
  • Laporte R, Hui A, Laher I. Pharmacological modulation of sarcoplasmic reticulum function in smooth muscle. Pharmacol Rev 2004;56:439–513.
  • Horakova L, Sies H, Steenken S. Antioxidant action of stobadine. Meth Enzymol 1994;234:572–581.
  • Juranek I, Horakova L, Rackova L, Stefek M. Antioxidants in treating pathologies involving oxidative damage: an update on medicinal chemistry and biological activity of stobadine and related pyridoindoles. Curr Med Chem 2009;17: 552–570.
  • Packer L, Weber SU, Rimbach G. Molecular aspects of alpha-tocotrienol antioxidant action and cell signalling. J Nutr 2001;131:369–373.
  • Drieu K. Preparation and definition of the extract of Ginkgo biloba. Pres Méd 1986;15:1455–1457.
  • Sastre J, Millan A, De La Asuncion JG, Pla JG, Pallardo FV, O´Connor E, Martin JA, Droy-Lefaix MT, Viña J. A Ginkgo biloba extract (EGb 761) prevents mitochondrial aging by protecting against oxidative stress. Free Radic Biol Med 1998;24:298–304.
  • Packer L, Rimbach G, Virgili F. Antioxidant activity and biologic properties of a procyanidin-rich extract from pine (Pinus maritima) bark, pycnogenol. Free Radic Biol Med 1999;27:704–724.
  • Schroeter H, Williams RJ, Matin R, Iversen L, Rice-Evans CA. Phenolic antioxidants attenuate neuronal cell death following uptake of oxidized low-density lipoprotein. Free Radic Biol Med 2000;29:1222–1233.
  • Ishige K, Schubert D, Sagara Y. Flavonoids protect neuronal cells from oxidative stress by three distinct mechanisms. Free Radic Biol Med 2001;30:433–446.
  • Strosova M, Skuciova M, Horakova L. Oxidative damage to Ca2+-ATPase sarcoplasmic reticulum by HOCl and protective effect of some antioxidants. Biofactors 2005;24: 111–116.
  • Strosova M, Karlovska J, Spickett CM, Grune T, Orszaghova Z, Horakova Ľ. Oxidative injury induced by hypochlorous acid to Ca-ATPase from sarcoplasmic reticulum of skeletal muscle and protective effect of trolox. Gen Physiol Biophys 2009;28:195–209.
  • Pick U, Karlish SJD. Indications for an oligomeric structure and for conformational changes in sarcoplasmic reticulum Ca2+-ATPase labelled selectively with fluorescein. Biochim Biophys Acta 1980;626:255–261.
  • Pekiner B, Ulusu NN, Das-Evcimen N, Sahilli M, Aktan F, Štefek M, Štolc S, Karasu Ç. In vivo treatment with stobadine prevents lipid peroxidation, protein glycation and calcium overload but does not ameliorate Ca2+-ATPase activity in heart and liver of streptozotocin-diabetic rats: comparison with vitamin E. Biochim Biophys Acta 2002; 1588:71–78.
  • Sivonová M, Zitnanová I, Horáková L, Strosová M, Muchová J, Balgavý P, Dobrota D, Duracková Z. The combined effect of pycnogenol with ascorbic acid and trolox on the oxidation of lipids and proteins. Gen Physiol Biophys 2006;25: 379–396.
  • Golod EA. [The membrane phospholipid peroxidation and Ca-dependent ATPase activity of the microsomal fractions isolated from rat renal tissue in thermal ischemia with and without alpha-tocopherol protection]. Urol Nephrol (Moscow) 1997;5:5–9.
  • Kuzmina IL, Timofeev AA, Germanov SV, Levchenko LV, Kulish MA. Protective effect of alpha-tocopherol on the Ca2+-transport system of the sarcoplasmic reticulum membranes in hypercholesterolemia. Byull Exp Biol Med (Moscow) 1986;101:163–165.
  • Tappia PS, Hata T, Hozaima L, Sandhu MS, Panagia V, Dhalla NS. Role of oxidative stress in catecholamineinduced changes in cardiac sarcolemmal Ca2+ transport. Arch Biochem Biophys 2001;387:85–92.
  • Pekiner BD, Daş Evcimen N, Ulusu NN, Bali M, Karasu C. Effects of vitamin E on microsomal Ca2+-ATPase activity and calcium levels in streptozotocin-induced diabetic rat kidney. Cell Biochem Funct 2003;21:177–182.
  • Qiu Y, Li YY, Li SG, Song BG, Zhao GF. Effect of Qingyitang on activity of intracellular Ca2+-Mg2+-ATPase in rats with acute pancreatitis. World J Gastroenterol 2004;10: 100–104.
  • Wauben MHM, Wagenaar-Hilbers JPA, van Eden W. Adjuvant arthritis. Cohen IR, Miller A. Autoimmune disease models a guidebook. Academic Press, San Diego; 1994. 201–215.
  • Squier TC, Bigelow DJ. Protein oxidation and agedependent alterations in calcium homeostasis. Front Biosci 2000;5: 504–526.
  • Restall CJ, Coke M, Phillips E, Chapman D. Derivative spectroscopy of tryptophan fluorescence used to study conformational transitions in the (Ca2+ + Mg2+)-adenosine triphosphatase of sarcoplasmic reticulum. Biochim Biophys Acta 1986;874:305–311.
  • Strosová M, Tomaskova I, Ponist S, Bauerova K, Karlovská J, Spickett MC, Horakova L. Oxidative impairment of plasma and skeletal muscle sarcoplasmic reticulum in rats with adjuvant arthritis - effects of pyridoindole antioxidants. Neuroendocrinol Lett 2008;29:706–711.
  • Steenken S, Sundquist AR, Jovanovic SV, Crockett R, Sies H. Antioxidant activity of the pyridoindole stobadine. Pulse radiolytic characterization of one-electron-oxidized stobadine and quenching of singlet molecular oxygen. Chem Res Toxicol 1992;5:355–360.
  • Horáková L, Giessauf A, Raber G, Esterbauer H. Effect of stobadine on Cu++ mediated oxidation of low-density lipoprotein. Biochem Pharmacol 1996;51:1277–1282.
  • Račková L, Šnirc V, Májeková M, Májek P, Štefek M. Free radical scavenging and antioxidant activities of substituted hexahydropyridoindoles. Quantitative structure-activity relationships. J Med Chem 2006;49:2543–2548.
  • Stadtman ER. Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metalcatalyzed reactions. Annu Rev Biochem 1993;62:797–821.
  • Berlett BS, Stadtman ER. Protein oxidation in aging, disease, and oxidative stress. J Biol Chem 1997;272:20313–20316.
  • Masoro EJ. Challenges of biological aging. New York: Springer Publishing Company; 1999.
  • Middleton EJ, Kandaswami C, Theoharides TC. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol Rev 2000;52:673–751.
  • Kajiya K, Kumazawa S, Naito A, Nakayama T. Solid-state NMR analysis of the orientation and dynamics of epigallocatechin gallate, a green tea polyphenol, incorporated into lipid bilayers. Magn Reson Chem 2007;46:174–177.
  • Oteiza P, Erlejman A, Verstraeten S, Keen C, Fraga C. Flavonoid-membrane interactions: a protective role of flavonoids at the membrane surface? Clin Dev Immunol 2005;12:19–25.
  • Ulrih NP, Ota A, Šentjurc M, Kure S, Abram V. Flavonoids and cell membrane fluidity. Food Chem 2010;121:78–84.
  • Erlejman AG, Verstraeten SV, Fraga CG, Oteiza PI. The interaction of flavonoids with membranes: potential determinant of flavonoid antioxidant effects. Free Radic Res 2004;38:1311–1320.
  • Saija A, Bonina F, Trombetta D, Tomaino A, Montenegro L, Smeriglio P, Castelli F. Flavonoids as antioxidant agents: importance of their interaction with biomembranes. Free Radic Biol Med 1995;19:481–486.
  • Seydel JK, Coats EA, Cordes HP, Wiese M. Drug membrane interaction and the importance for drug transport, distribution, accumulation, efficacy and resistance. Arch Pharm (Weinheim) 1994;327:601–610.
  • Movileanu L, Neagoe I, Flonta ML. Interaction of the antioxidant flavonoid quercetin with planar lipid bilayers. Int J Pharm 2000;205:135–146.
  • Rego AC, Oliveira CR. Dual effect of lipid peroxidation on the membrane order of retinal cells in culture. Arch Biochem Biophys 1995;321:127–136.
  • Pawlikowska-Pawlęga B, Gruszecki WI, Misiak L, Paduch R, Piersiak T, Zarzyka B, Pawelec J, Gawron A. Modification of membranes by quercetin, a naturally occurring flavonoid via its incorporation in the polar head group. Biochim Biophys Acta 2007;1768:2195–2204.
  • Kodelia G, Athanasiou K, Kolisis FN. Enzymatic synthesis of butyryl-rutin ester in organic solvents and its cytogenetic effects in mammalian cells in culture. Appl Biochem Biotechnol 1994;44:205–212.
  • Ishihara K, Nakajima N. Structural aspects of acylated plant pigments: stabilization of flavonoid glucosides and interpretation of their functions. J Mol Catal B 2003;23:411–417.
  • Ardhaoui M, Falcimaigne A, Engasser J-M, Moussou P, Pauly G, Ghoul M. Acylation of natural flavonoids using lipase of Candida antarctica as biocatalyst. J Mol Catal B 2004;29:63–67.
  • Katsoura MH, Polydera AC, Tsironis L, Tselepis AD, Stamatis H. Use of ionic liquids as media for the biocatalytic preparation of flavonoid derivatives with antioxidant potency. J Biotechnol 2006;123:491–503.
  • Mellou F, Lazari D, Skaltsa H, Tselepis AD, Kolisis FN, Stamatis H. Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity. J Biotechnol 2005;116:295–304.
  • Mellou F, Loutrari H, Stamatis H, Roussos C, Kolisis FN. Enzymatic esterification of flavonoids with unsaturated fatty acids: effect of novel esters on vascular endothelial growth factor release from K562 cells. Process Biochem 2006;41: 2029–2034.
  • Suda I, Oki T, Masuda M, Nishiba Y, Furuta S, Matsugano K, Sugita K, Terahara N. Direct absorption of acylated anthocyanin in purplefleshed sweet potato into rats. J Agric Food Chem 2002;50:1672–1676.
  • Viskupicova J, Ondrejovic M, Sturdik E. The potential and practical applications of acylated flavonoids. Pharmazie 2009;64:355–360.
  • Viskupicova J, Danihelova M, Ondrejovic M, Liptaj T, Sturdik E. Lipophilic rutin derivatives for antioxidant protection of oil-based foods. Food Chem 2010;In press.
  • Viskupicova J, Danihelova M, Ondrejovic M [Lipophilic rutin derivatives with antioxidant activity]. Modra: Food Research Institute; 2008.
  • Ardhaoui M, Falcimaigne A, Ognier S, Engasser J-M, Moussou P, Pauly G, Ghoul M. Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids. J Biotechnol 2004;110:265–272.
  • Kontogianni A, Skouridou V, Sereti V, Stamatis H, Kolisis FN. Regioselective acylation of flavonoids catalyzed by lipase in low toxicity media. Eur J Lipid Sci Technol 2001;103: 655–660.
  • Chebil L, Humeau C, Falcimaigne A, Engasser J-M, Ghoul M. Enzymatic acylation of flavonoids. Process Biochem 2006;41:2237–2251.
  • Middleton EJ, Kandaswami C. The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. Harborne JB. The Flavonoids - advances in research since 1986. London: Chapman & Hall; 1994. 619–652.
  • Bhendrich A. Flavonoid-membrane interactions: possible consequences for biological effects of some polyphenolic compounds. Acta Pharmacol Sin 2006;27:27–40.
  • Ogunbayo OA, Harris RM, Waring RH, Kirk CJ, Michelangeli F. Inhibition of the sarcoplasmic/endoplasmic reticulum Ca2+-ATPase by flavonoids: a quantitative structure-activity relationship study. IUBMB Life 2008;60:853–858.
  • Morales MA, Lozoya X. Calcium-antagonist effects of quercetin on aortic smooth muscle. Planta Med 1994;60:313–317.
  • Viskupicova J, Strosova M, Horakova L, Sturdik E. Modulating effect of rutin and its derivatives on activity and conformation of sarcoplasmic reticulum Ca-ATPase. Drobnicov Memorial 2009;5:14–15.
  • Pérez-Victoria JM, Pérez-Victoria FJ, Conseil G, Maitrejean M, Comte G, Barron D, Di Pietro A, Castanys S, Gamarro F. High-affinity binding of silybin derivatives to the nucleotide-binding domain of a Leishmania tropica P-glycoprotein-like transporter and chemosensitization of a multidrug-resistant parasite to daunomycin. Antimicrob Agents Chemother 2000;45:439–446.
  • Chadwick CC, Thomas EW. Inactivation of sarcoplasmic reticulum (Ca2+ + Mg2+)-ATPase by N-cyclohexyl-N’-(4-dimethylamino-a-naphthyl) carbodimide. Biochim Biophys Acta 1983;730:201–206.
  • Kukreja RG, Okabe E, Schrier GM, Hess M. Oxygen radical-mediated lipid peroxidation and inhibition of Ca2+- ATPase activity of cardiac sarcoplasmic reticulum. Arch Biochem Biophys 1988;261:447–457.
  • Morris TE, Sulakhe PV. Sarcoplasmic reticulum Ca2+-pump dysfunction in rat cardiomyocytes briefly exposed to hydroxyl radicals. Free Radic Biol Med, 1997;22:37–47.
  • Xu KY, Zweier JL, Becker LC. Hydroxyl radical inhibits sarcoplasmic reticulum Ca2+-ATPase function by direct attack on the ATP binding site. Circ Res 1997;80:76–81.
  • Viner RI, Williams TD, Schöneich C. Peroxynitrite modification of protein thiols: oxidation, nitrosylation, and S-glutathiolation of functionally important cysteine residue(s) in the sarcoplasmic reticulum Ca-ATPase. Biochemistry 1999;38: 12408–12415.
  • Viskupicova J, Strosova M, Horakova L, Sturdik E. Effect of rutin and its lipophilic derivatives on peroxynitrite-oxidized Ca-ATPase activity. Free Radic Res 2009;43:S81–S82.
  • Saija A, Bonina F, Trombetta D, Tomaino A, Montenegro L, Smeriglio P, Castelli F. Flavonoid-biomembrane interactions: a calorimetric study on dipalmitoylphosphatidylcholine vesicles. Int J Pharm 1995;124:1–8.
  • Cornwell PA, Barry BW, Bouwstra JA, Gooris GS. Modes of action of terpene penetration enhancers in human skin; differential scanning calorimetry, small-angle X-ray diffraction and enhancer uptake studies. Int J Pharm 1996;127: 9–26.
  • Suwalsky M, Vargas P, Avello M, Villenac F, Sotomayor CP. Human erythrocytes are affected in vitro by flavonoids of Aristotelia chilensis (Maqui) leaves. Int J Pharm 2008;363: 85–90.
  • Illinger D, Duportail G, Mely Y, Poirel-Morales N, Gerard D, Kuhry JG. A comparison of the fluorescence properties of TMA-DPH as a probe for plasma membrane and for endocytic membrane. Biochim Biophys Acta 1995;1239: 58–66.
  • Tsuchiya H. Structure-dependent membrane interaction of flavonoids associated with their bioactivity. Food Chem 2010;120:1089–1096.
  • Gallicchio L, Boyd K, Matanoski G, Tao XG, Chen L, Lam TK, Shiels M, Hammond E, Robinson KA, Caulfield LE, Herman JG, Guallar E, Alberg AJ. Carotenoids and the risk of developing lung cancer: a systematic review. Am J Clin Nutr 2008;88:372–383.
  • Robinson I, de Serna DG, Gutierrez A, Schade DS. Vitamin E in humans: an explanation of clinical trial failure. Endocr Pract 2006;12:576–582.
  • Dotan Y, Lichtenberg D, Pinchuk I. No evidence supports vitamin E indiscriminate supplementation. Biofactors 2009; 35:469–473.
  • Elswaifi SF, Palmieri JR, Hockey KS, Rzigalinski BA. Antioxidant nanoparticles for control of infectious disease. Infect Disord Drug Targets 2009;9:445–452.
  • Leonarduzzi G, Robbesyn F, Poli G. Signaling kinases modulated by 4-hydroxynonenal. Free Radic Biol Med 2004; 37:1694–1702.
  • Rokitskaya TI, Klishin SS, Severina II, Skulachev VP, Antonenko YN. Kinetic analysis of permeation of mitochondria-targeted antioxidants across bilayer lipid membranes. J Membr Biol 2008;224:9–19.
  • Skulachev VP, Anisimov VN, Antonenko YN, Bakeeva LE, Chernyak BV, Erichev VP, Filenko OF, Kalinina NI, Kapelko VI, Kolosova NG, Kopnin BP, Korshunova GA, Lichinitser MR, Obukhova LA, Pasyukova EG, Pisarenko OI, Roginsky VA, Ruuge EK, Senin II, Severina II, Skulachev MV, Spivak IM, Tashlitsky VN, Tkachuk VA, Vyssokikh MY, Yaguzhinsky LS, Zorov DB. An attempt to prevent senescence: a mitochondrial approach. Biochim Biophys Acta 2009;1787: 437–461.
  • Levonen MD, Vähäkangas E, Koponen JK, Ylä-Herttuala S. Antioxidant gene therapy for cardiovascular disease: current status and future perspectives. Circulation 2008;117: 2142–2150.
  • Nivsarkar M, Banerjee A, Padh H. Cyclooxygenase inhibitors: a novel direction for Alzheimer’s management. Pharmacol Rep 2008;60:692–698.
  • Sovari AA, Morita N, Karagueuzian HS. Apocynin: a potent NADPH oxidase inhibitor for the management of atrial fibrillation. Redox Rep 2008;13:242–245.
  • Granot E, Golan D, Rivkin L, Kohen R. Oxidative stress in healthy breast fed versus formula fed infants. Nutrition Res 1999;19:869–879.
  • Mendilaharsu M, De Stefani E, Deneo-Pellegrini H, Carzoglio JC, Ro A. Consumption of tea and coffee and the risk of lung cancer in cigarette smoking men: a case control study in Uruguay. Lung Cancer 1998;19:101–107.
  • Jain MG, Hislop GT, Howe GR, Burch JD, Ghadirian P. Alcohol and other beverage use and prostate cancer among Canadian men. Int J Cancer 1998;78:707–711.
  • Bianchi GD, Cehan JR, Parker AS, Putnam SD, See WA, Lynch CF, Cantor KP. Tea consumption and risk of bladder and kidney cancers in a population-based case-control study. Am J Epidemiol 2000;151:377–383.
  • Sun CL, Yuan JM, Koh WP, Lee HP, Yu MC. Green tea and black tea consumption in relation to colorectal cancer risk: the Singapore Chinese Health Study. Carcinogenesis 2007;28:2143–2148.
  • Nagano J, Kono S, Preston DL, Moriwaki H, Sharp GB, Koyama K, Mabuchi K. Bladder-cancer incidence in relation to vegetable and fruit consumption: a prospective study of atomic-bomb survivors. Int J Cancer 2000;86:132–138.
  • Huang X, Tajima K, Hamajima N, Inoue M, Takezaki T, Kuroishi T, Hirose K, Tominaga S, Xiang J, Tokudome S. Effect of life styles on the risk of subsite-specific gastric cancer in those with and without family history. J Epidemiol 1999;9:40–45.
  • Shibata K, Moriyama M, Fukushima T, Kaetsu A, Miyazaki M, Une H. Green tea consumption and chronic atrophic gastritis: a cross-sectional study in a green tea production village. J Epidemiol 2000;10:310–316.
  • Nakachi K, Matsuyama S, Miyake S, Suganuma M, Imai K. Preventive effects of drinking green tea on cancer and cardiovascular disease: epidemiological evidence for multiple targeting prevention. Biofactors 2000;13:49–54.
  • Setiawan VW, Zhang ZF, Yu GP, Lu QY, Li YL, Lu ML, Wang MR, Guo CH, Yu SZ, Kurtz RC, Hsieh CC. Protective effect of green tea on the risks of chronic gastritis and stomach cancer. Int J Cancer 2001;92:600–604.
  • Davies MJ, Judd JT, Baer DJ, Clevidence BA, Paul DR, Edwards AJ, Wiseman SA, Muesing RA, Chen SC. Black tea consumption reduces total and LDL cholesterol in mildly hypercholesterolemic adults. J Nutr 2003;133:3298–3302.
  • Hakim IA, Alsaif MA, Alduwaihy M, Al-Rubeaan K, Al-Nuaim AR, Attas OS. Tea consumption and the prevalence of coronary heart disease in Saudi adults: results from a Saudi national study. Prev Med 2003;36:64–70.
  • Maron DJ, Lu GP, Cai NS, Wu ZG, Li YH, Chen H, Zhu JQ, Jin XJ, Wouters BC, Zhao J. Cholesterol-lowering effect of a theaflavin-enriched green tea extract: a randomized controlled trial. Arch Intern Med 2003;163:1448–1453.
  • Nagaya N, Yamamoto H, Uematsu M, Itoh T, Nakagawa K, Miyazawa T, Kangawa K, Miyatake K. Green tea reverses endothelial dysfunction in healthy smokers. Heart 2004;90: 1485–1486.
  • Erba D, Riso P, Bordoni A, Foti P, Biagi PL, Testolin G. Effectiveness of moderate green tea consumption on antioxidative status and plasma lipid profile in humans. J Nutr Biochem 2005;16:144–149.
  • Van Dorsten FA, Daykin CA, Mulder TP, Van Duynhoven JP. Metabonomics approach to determine metabolic differences between green tea and black tea consumption. J Agric Food Chem 2006;54:6929–6238.
  • Nagao T, Hase T, Tokimitsu I. A green tea extract high in catechins reduces body fat and cardiovascular risks in humans. Obesity (Silver Spring) 2007;15:1473–1483.
  • Checkoway H, Powers K, Smith-Weller T, Franklin GM, Longstreth JWT, Swanson PD. Parkinson’s disease risks associated with cigarette smoking, alcohol consumption, and caffeine intake. Am J Epidemiol 2002;155:732–738.
  • Hu G, Bidel S, Jousilahti P, Antikainen R, Tuomilehto J. Coffee and tea consumption and the risk of Parkinson’s disease. Mov Disord 2007;22:2242–2248.
  • Simic MG. Peroxyl radical from oleic acid. Simic MG, Karel M. Autoxidation in food and biological systems. New York: Plenum; 1980. 17–26.
  • Nonell S, Moncayo L, Trull F, Amat-Guerri F, Lissi EA, Soltermann AT, Criado S, García NA. Solvent influence on the kinetics of the photodynamic degradation of trolox, a water-soluble model compound for vitamin E. J Photochem Photobiol B 1995;29:157–162.
  • Tepel M. N-Acetylcysteine in the prevention of ototoxicity. Kidney Int 2007;72:231–232.
  • Tepel M, van der Giet M, Schwarzfeld C, Laufer U, Liermann D, Zidek W. Prevention of radiographic-contrast-agent-induced reductions in renal function by acetylcysteine. N Engl J Med 2000;343:180–184.
  • Scholze A, Rinder C, Beige J, Riezler R, Zidek W, Tepel M. Acetylcysteine reduces plasma homocysteine concentration and improves pulse pressure and endothelial function in patients with end-stage renal failure. Circulation 2004;109: 369–374.
  • Tepel M. Acetylcysteine for the prevention of radiocontrast-induced nephropathy. Minerva Cardioangiol 2003;51: 525–530.
  • Jones AL. Mechanism of action and value of N-acetylcysteine in the treatment of early and late acetaminophen poisoning: a critical review. J Toxicol Clin Toxicol 1998;36: 277–285.
  • Suzuki K. Anti-oxidants for therapeutic use: why are only a few drugs in clinical use? Adv Drug Deliv Rev 2009;61:287–289.
  • Rahman I. Antioxidant therapeutic advances in COPD. Ther Adv Respir Dis 2008;2:351–374.
  • Conklin KA. Coenzyme Q10 for prevention of anthracycline-induced cardiotoxicity. Integr Cancer Ther 2005;4:110–130.
  • Littarru GP, Tiano L. Clinical aspects of coenzyme Q10: an update. Nutrition 2010;26:250–254.
  • Adarsh K, Kaur H, Mohan V. Coenzyme Q10 (CoQ10) in isolated diastolic heart failure in hypertrophic cardiomyopathy (HCM). Biofactors 2008;32:145–149.
  • Tiano L, Padella L, Carnevali P, Gabrielli O, Bruge F, Principi F, Littarru GP. Coenzyme Q10 and oxidative imbalance in Down syndrome: biochemical and clinical aspects. Biofactors 2008;32:161–167.
  • Sándor PS, Di Clemente L, Coppola G, Saenger U, Fumal A, Magis D. Efficacy of coenzyme Q10 in migraine prophylaxis: a randomized controlled trial. Neurology 2005;64: 713–715.
  • Vicari E, Arcoria D, Di Mauro C, Noto R, Noto Z, La Vignera S. Sperm output in patients with primary infertility and hepatitis B or C virus; negative influence of HBV infection during concomitant varicocele. Minerva Med 2006;97: 65–77.
  • Hill MF. Emerging role for antioxidant therapy in protection against diabetic cardiac complications: experimental and clinical evidence for utilization of classic and new antioxidants. Curr Cardiol Rev 2008;4:259–268.
  • Suleiman SA, Ali ME, Zaki ZM, El-Malik EM, Nasr MA. Lipid peroxidation and human sperm motility: protective role of vitamin E. J Androl 1996;17:530–537.
  • Kamat CD, Gadal S, Mhatre M, Williamson KS, Pye QN, Hensley K. Antioxidants in central nervous system diseases: preclinical promise and translational challenges. J Alzheimers Dis 2008;15:473–493.
  • Gitto E, Pellegrino S, Gitto P, Barberi I, Reiter RJ. Oxidative stress of the newborn in the pre- and postnatal period and the clinical utility of melatonin. J Pineal Res 2009;46: 128–139.
  • Aaseth J, Haugen M, Førre O. Rheumatoid arthritis and metal compounds–perspectives on the role of oxygen radical detoxification. Analyst 1998;123:3–6.
  • Soule BP, Hyodo F, Matsumoto K, Simone NL, Cook JA, Krishna MC, Mitchell JB. Therapeutic and clinical applications of nitroxide compounds. Antioxid Redox Signal 2007;9:1731–1743.
  • Yamashita S, Hbujo H, Arai H, Harada-Shiba M, Matsui S, Fukushima M, Saito Y, Kita T, Matsuzawa Y. Long-term probucol treatment prevents secondary cardiovascular events: a cohort study of patients with heterozygous familial hypercholesterolemia in Japan. J Atheroscler Thromb 2008; 15:292–303.
  • Tardif JC, Cöté G, Lespérance J, Bourassa M, Lambert J, Doucet S, Bilodeau L, Nattel S, de Guise P. Probucol and multivitamins in the prevention of restenosis after coronary angioplasty. Multivitamins and Probucol Study Group. N Engl J Med 1997;337:365–372.
  • Tardif JC, Grégoire J, Schwartz L, Title L, Laramée L, Reeves F, Lespérance J, Bourassa MG, L’Allier PL, Glass M, Lambert J, Guertin MC. Effects of AGI-1067 and probucol after percutaneous coronary interventions. Circulation 2003;107:552–558.
  • Yamaguchi T, Sano K, Takakura K, Saito I, Shinohara Y, Asano T, Yasuhara H. Ebselen in acute ischemic stroke: a placebo-controlled, double-blind clinical trial. Ebselen Study Group. Stroke 1998;29:12–17.

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