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Assessment of antioxidant capacity in vitro and in vivo. Free Radical Biol. Med. 49, 503-515 (2010).","DOI":"10.1016\/j.freeradbiomed.2010.04.016"},{"key":"2","doi-asserted-by":"crossref","unstructured":"2) Niki, E. Role of vitamin E as a lipid-soluble peroxyl radical scavenger: in vitro and in vivo evidence. Free Radical Biol. Med. 66, 3-12 (2014), and references are cited therein.","DOI":"10.1016\/j.freeradbiomed.2013.03.022"},{"key":"3","doi-asserted-by":"crossref","unstructured":"3) Traber, M.G.; Atkinson, J. Vitamin E, antioxidant and nothing more. Free Radical Biol. Med. 43, 4-15 (2007).","DOI":"10.1016\/j.freeradbiomed.2007.03.024"},{"key":"4","doi-asserted-by":"crossref","unstructured":"4) Esterbauer, H.; Dieber-Rotheneder, M.; Striegl, G.; Waeg, G. Role of vitamin E in preventing the oxidation of low-density lipoprotein. Am. J. Clin. Nutr. 53, 314S-321S (1991).","DOI":"10.1093\/ajcn\/53.1.314S"},{"key":"5","unstructured":"6) Burton, G.W.; Doba, T.; Gabe, E.J.; Hughes, L.; Lee, F.L.; Prasad, L.; Ingold, K.U. Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols. J. Am. Chem. Soc. 107, 7053-7065 (1985)."},{"key":"6","doi-asserted-by":"crossref","unstructured":"7) Terao, J.; Matsushita, S. The Peroxidizing effect of \u03b1-tocopherol on autoxidation of methyl linoleate in bulk phase. Lipids 21, 255-260 (1986).","DOI":"10.1007\/BF02536407"},{"key":"7","unstructured":"8) Bowry, V.W.; Stocker, R. Tocopherol-mediated peroxidation. The prooxidant effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein. J. Am. Chem. Soc. 115, 6029-6044 (1993)."},{"key":"8","doi-asserted-by":"crossref","unstructured":"9) Mukai, K.; Noborio, S.; Nagaoka, S. Why is the order reverses ? Peroxyl-scavenging activity and fats-and-oils protecting activity of vitamin E. Int. J. Chem. Kinet. 37, 605-610 (2005).","DOI":"10.1002\/kin.20114"},{"key":"9","doi-asserted-by":"crossref","unstructured":"10) Nagaoka, S.; Okauchi, Y.; Urano, S.; Nagashima, U.; Mukai, K. Kinetic and ab initio study of the prooxidant effect of vitamin E. Hydrogen abstraction from fatty acid esters and egg yolk lecithin. J. Am. Chem. Soc. 112, 8921-8924 (1990).","DOI":"10.1021\/ja00180a042"},{"key":"10","doi-asserted-by":"crossref","unstructured":"11) Ouchi, A.; Ishikura, M.; Konishi, K.; Nagaoka, S.; Mukai, K. Kinetic study of the prooxidant effect of \u03b1-tocopherol. Hydrogen abstraction from lipids by \u03b1-tocopheroxyl radical. Lipids 44, 935-943 (2009).","DOI":"10.1007\/s11745-009-3339-x"},{"key":"11","unstructured":"12) Ernster, L.; Dallner, G. Biochemical, Physiological and medical aspects of ubiquinone function. Biochim. Biophys. Acta 1271, 195-204 (1995)."},{"key":"12","doi-asserted-by":"crossref","unstructured":"13) Yamamoto, Y.; Komuro, E.; Niki, E. Antioxidant activity of ubiquinol in solition and phosphatidylcholine liposome. J. Nutr. Sci. Vitaminol. 36, 505-511 (1990).","DOI":"10.3177\/jnsv.36.505"},{"key":"13","doi-asserted-by":"crossref","unstructured":"14) Frei, B.; Kim, M.C.; Ames, B.N. Ubiquinol-10 is an effective lipid-soluble antioxidant at physiological concentrations. Proc. Natl. Acad. Sci. USA 87, 4879-4883 (1990).","DOI":"10.1073\/pnas.87.12.4879"},{"key":"14","doi-asserted-by":"crossref","unstructured":"15) Stocker, R.; Bowry, V.W.; Frei, B. Ubiquinol-10 protects human low density lipoprotein more efficiently against lipid peroxidation than does \u03b1-tocopherol. Proc. Natl. Acad. Sci. USA 88, 1646-1650 (1991).","DOI":"10.1073\/pnas.88.5.1646"},{"key":"15","doi-asserted-by":"crossref","unstructured":"16) Kagan, V.E.; Serbinova, E.; Packer, L. Antioxidant effects of ubiquinones in microsomes and mitochondria are mediated by tocopherol recycling. Biochem. Biophys. Res. Commun. 169, 851-857 (1990).","DOI":"10.1016\/0006-291X(90)91971-T"},{"key":"16","unstructured":"17) Naumov, V.V.; Khrapova, N.G. Study of the interaction of ubiquinone and ubiquinol with peroxide radicals by the chemiluminescent method. Biophysics (Engl. Transl. Biofizika) 28, 774-780 (1983)."},{"key":"17","doi-asserted-by":"crossref","unstructured":"18) Mukai, K.; Itoh, S.; Morimoto, H. Stopped-flow kinetic study of vitamin E regeneration reaction with biological hydroquinones (reduced forms of ubiquinone, vitamin K, and tocopherolquinone) in solution. J. Biol. Chem. 267, 22277-22281 (1992).","DOI":"10.1016\/S0021-9258(18)41666-3"},{"key":"18","unstructured":"19) Barclay, L.R.C.; Vinqvist, M.R.; Mukai, K.; Itoh, S.; Morimoto, H. Chain-breaking phenolic antioxidants: Steric and electronic effects in polyalkylchromanols, tocopherol analogs, hydroquinones, and superior antioxidants of the polyalkylbenzochromanol and naphthofuran class. J. Org. Chem. 58, 7416-7420 (1993)."},{"key":"19","unstructured":"20) Ouchi, A.; Nagaoka, S.; Mukai, K. Tunneling effect in regeneration reaction of vitamin E by ubiquinol. J. Phys. Chem. B 114, 6601-6607 (2010)."},{"key":"20","doi-asserted-by":"crossref","unstructured":"21) Packer, J.E.; Slater, T.F.; Willson, R.L. Direct observation of a free radical interaction between vitamin E and vitamin C. Nature 278, 737-738 (1979).","DOI":"10.1038\/278737a0"},{"key":"21","doi-asserted-by":"crossref","unstructured":"22) Niki, E.; Saito, T.; Kawakami, A.; Kamiya, Y. Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. J. Biol. Chem. 259, 4177-4182 (1984).","DOI":"10.1016\/S0021-9258(17)43026-2"},{"key":"22","doi-asserted-by":"crossref","unstructured":"23) Mukai, K.; Nishimura, M.; Kikuchi, S. Stopped-flow investigation of the reaction of vitamin C with tocopheroxyl radical in aqueous Triton X-100 micellar solutions. J. Biol. Chem. 266, 274-278 (1991).","DOI":"10.1016\/S0021-9258(18)52431-5"},{"key":"23","doi-asserted-by":"crossref","unstructured":"24) Bisby, R.H.; Parker, A.W. Reaction of ascorbate with the \u03b1-tocopheroxyl radical in micellar and bilayer membrane systems. Arch. Biochem. Biophys. 317, 170-178 (1995).","DOI":"10.1006\/abbi.1995.1150"},{"key":"24","doi-asserted-by":"crossref","unstructured":"25) Rice-Evans, C.A.; Miller, N.J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol. Med. 20, 933-956 (1996).","DOI":"10.1016\/0891-5849(95)02227-9"},{"key":"25","doi-asserted-by":"crossref","unstructured":"26) Vinson, J.A.; Proch, J.; Bose, P. Determination of quantity and quality of polyphenol antioxidants in foods and beverages. Methods Enzymol. 335, 103-114 (2001).","DOI":"10.1016\/S0076-6879(01)35235-7"},{"key":"26","doi-asserted-by":"crossref","unstructured":"27) Jia, Z.-S.; Zhou, B.; Yang, L.; Wu, L.-M.; Liu, Z.-L. Antioxidant synergism of tea polyphenols and \u03b1-tocopherol against free radical induced peroxidation of linoleic acid in solution, J. Chem. Soc. Perkin Trans 2. 911-915 (1998).","DOI":"10.1039\/a706691k"},{"key":"27","doi-asserted-by":"crossref","unstructured":"28) Zhou, B.; Jia, Z.-S.; Chen, Z.-H.; Yang, L.; Wu, L.-M.; Liu, Z.-L. Synergistic antioxidant effect of green tea polyphenols with \u03b1-tocopherol on free radical initiated peroxidation of linoleic acid in micelles, J. Chem. Soc., Perkin Trans. 2. 785-791 (2000).","DOI":"10.1039\/a908084h"},{"key":"28","doi-asserted-by":"crossref","unstructured":"29) Terao, J.; Piskula, M.; Yao, Q. Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Arch. Biochem. Biophys. 308, 278-284 (1994).","DOI":"10.1006\/abbi.1994.1039"},{"key":"29","doi-asserted-by":"crossref","unstructured":"30) Liu, Z.-Q.; Ma, L.-P.; Zhou, B.; Yang, L.; Liu, Z.-L. Antioxidative effects of green tea polyphenols on free radical initiated and photosensitized peroxidation of human low density lipoprotein. Chem. Phys. Lipids 106, 53-63 (2000).","DOI":"10.1016\/S0009-3084(00)00133-X"},{"key":"30","doi-asserted-by":"crossref","unstructured":"31) Mukai, K.; Mitani, S.; Ohara, K.; Nagaoka, S. Structure-activity relationship of the tocopherol-regeneration reaction by catechins. Free Radical Biol. Med. 38, 1243-1256 (2005).","DOI":"10.1016\/j.freeradbiomed.2005.01.011"},{"key":"31","doi-asserted-by":"crossref","unstructured":"32) Zhou, B.; Wu, L.-M.; Yang, L.; Liu, Z.-L. Evidence for \u03b1-tocopherol regeneration reaction of green tea polyphenols in SDS micelles. Free Radical Biol. Med. 38, 78-84 (2005).","DOI":"10.1016\/j.freeradbiomed.2004.09.023"},{"key":"32","doi-asserted-by":"crossref","unstructured":"33) Nagaoka, S.; Nitta, A.; Suemitsu, A.; Mukai, K. Tunneling effect in vitamin E recycling by green tea. 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Finding of linear correlation between the rates of quenching of singlet oxygen and scavenging of peroxyl and phenoxyl radicals in solution. J. Org. Chem. 56, 4188-4192 (1991)."},{"key":"36","unstructured":"37) Nagaoka, S.; Kuranaka, A.; Tsuboi, H.; Nagashima, U.; Mukai, K. Mechanism of antioxidant reaction of vitamin E. Charge transfer and tunneling effect in proton-transfer reaction. J. Phys. Chem. 96, 2754-2761 (1992)."},{"key":"37","unstructured":"38) Mukai, K.; Tokunaga, A.; Itoh, S.; Kanesaki, Y.; Ohara, K.; Nagaoka, S.; Abe, K. Structure-activity relationship of the free-radical-scavenging reaction by vitamin E (\u03b1-, \u03b2-, \u03b3-, \u03b4-tocopherols) and ubiquinol-10: pH dependence of the reaction rates. J. Phys. Chem. B 111, 652-662 (2007)."},{"key":"38","doi-asserted-by":"crossref","unstructured":"39) Mitani, S.; Ouchi, A.; Watanabe, E.; Kanesaki, Y.; Nagaoka, S.; Mukai, K. Stopped-flow kinetic study of the aroxyl radical-scavenging action of catechins and vitamin C in ethanol and micellar solutions. J. Agric. Food Chem. 56, 4406-4417 (2008).","DOI":"10.1021\/jf703770m"},{"key":"39","unstructured":"40) de Rijke, Y.B.; Demacker, P.N.M.; Assen, N.A.; Sloots, L.M.; Katan, M.B.; Stalenhoef, A.F.H. Red wine consumption does not affect oxidizability of low-density lipoproteins in volunteers. Am. J. Clin. Nutr. 63, 329-334 (1996)."},{"key":"40","doi-asserted-by":"crossref","unstructured":"41) Podda, M.; Weber, C.; Traber, M.G.; Packer, L. Simultaneous determination of tissue tocopherols, tocotrienols, ubiquinols, and ubiquinones. J. Lipid Res. 37, 893-901 (1996).","DOI":"10.1016\/S0022-2275(20)37587-8"},{"key":"41","unstructured":"42) Colom\u00e9, C.; Artuch, R.; Vilaseca, M.-A.; Sierra, C.; Brandi, N.; Lambruschini, N.; Cambra, F.J.; Campistol, J. Lipophilic antioxidants in patients with phenylketonuria. Am. J. Clin. Nutr. 77, 185-188 (2003)."},{"key":"42","unstructured":"43) Mukai, K.; Ouchi, A.; Nakaya, S.; Nagaoka, S. Aroxyl-radical-scavenging rate increases remarkably under the coexistence of \u03b1-tocopherol and ubiquinol-10 (or vitamin C) : Finding of synergistic effect on the reaction rate. J. Phys. Chem. B 117, 8378-8391 (2013), and references are cited therein."},{"key":"43","unstructured":"44) Moreda, W.; P\u00e9rez-Camino, M.C.; Cert, A. Gas and liquid chromatography of hydrocarbons in edible vegetable oils. J. Chromatogr. A 936, 159-171 (2001)."},{"key":"44","doi-asserted-by":"crossref","unstructured":"45) Mukai, K.; Hirata, M.; Ito, J.; Shiomi, T.; Nakagawa, K.; Nagaoka, S. Kinetic study of singlet-oxygen quenching and aroxyl-radical scavenging activities of vitamin E homologues and fatty acids present in vegetable oils. J. Oleo Sci. 69, 7-22 (2020).","DOI":"10.5650\/jos.ess19217"},{"key":"45","doi-asserted-by":"crossref","unstructured":"46) Tuberoso, C.I.G.; Kowalczyk, A.; Sarritzu, E.; Cabras, P. Determination of antioxidant compounds and antioxidant activity in commercial oilseeds for food use. Food Chem. 103, 1494-1501 (2007).","DOI":"10.1016\/j.foodchem.2006.08.014"},{"key":"46","doi-asserted-by":"crossref","unstructured":"47) Cabrini, L.; Barzanti, V.; Cipollone, M.; Fiorentini, D.; Grossi, G.; Tolomelli, B.; Zambonin, L.; Landi, L. Antioxidants and total peroxyl radical-trapping ability of olive and seed oils. J. Agric. Food Chem. 49, 6026-6031 (2001).","DOI":"10.1021\/jf010837t"},{"key":"47","unstructured":"48) Cert, A.; Moreda, W.; P\u00e9rez-Camino, M.C. Chromatographic analysis of minor constituents in vegetable oils. J. Chromatogr. A 881, 131-148 (2000)."},{"key":"48","unstructured":"49) Mukai, K.; Bandoh, Y.; Ito, J.; Kobayashi, E.; Nakagawa, K.; Nagaoka, S. Kinetic study of the scavenging reaction of the aroxyl radical by eight kinds of vegetable oils in solution. J. Am. Oil Chem. Soc. 95, 731-742 (2018), and references are cited therein."},{"key":"49","doi-asserted-by":"crossref","unstructured":"50) Rieker, A.; Scheffler, K. Die beteiligung von phenylresten an der aroxylmesomerie. Liebigs Ann. Chem. 689, 78-92 (1965).","DOI":"10.1002\/jlac.19656890107"},{"key":"50","unstructured":"51) Mukai, K.; Ouchi, A.; Mitarai, A.; Ohara, K.; Matsuoka, C. Formation and decay dynamics of vitamin E radical in the antioxidant reaction of vitamin E. Bull. Chem. Soc. Jpn. 82, 494-503 (2009)."},{"key":"51","doi-asserted-by":"crossref","unstructured":"52) Parker, A.W.; Hester, R.E.; Phillips, D.; Umapathy, S. Time-resolved resonance raman spectroscopic investigations of the photochemistry of ubiquinone. J. Chem. Soc. Faraday Trans. 88, 2649-2653 (1992).","DOI":"10.1039\/ft9928802649"},{"key":"52","doi-asserted-by":"crossref","unstructured":"53) Durand, E.; Zhao, Y.; Coupland, J.N.; Elias, R.J. Assessing interactions between lipophilic and hydrophilic antioxidants in food emulsions. J. Agric. Food Chem. 63, 10655-10661 (2015).","DOI":"10.1021\/acs.jafc.5b04152"},{"key":"53","unstructured":"54) Yin, J.; Becker, M.E.; Andersen, M.L.; Skibsted, L.H. Green tea extract as food antioxidant. Synergism and antagonism with \u03b1-tocopherol in vegetable oils and their colloidal systems. Food Chem. 135, 2195-2202 (2012)."},{"key":"54","doi-asserted-by":"crossref","unstructured":"55) Valgimigli, L.; Ingold, K.U.; Lusztyk, J. Antioxidant activities of vitamin E analogues in water and a Kamlet-Taft \u03b2-value for water. J. Am. Chem. Soc. 118, 3545-3549 (1996).","DOI":"10.1021\/ja954030r"},{"key":"55","doi-asserted-by":"crossref","unstructured":"56) Simic, M.G.; Jovanovic, S.V.; Niki, E. Mechanisms of lipid oxidative processes and their inhibition. in Lipid Oxidation in Food (St. Angelo, A.J. ed.), ACS Symposium Series 500, American Chemical Society, Washington, DC, pp. 14-32 (1992).","DOI":"10.1021\/bk-1992-0500.ch002"},{"key":"56","doi-asserted-by":"crossref","unstructured":"57) Evans, M.G.; Polanyi, M. Inertia and driving force of chemical reactions. Trans. Faraday Soc. 34, 11-24 (1938).","DOI":"10.1039\/tf9383400011"},{"key":"57","unstructured":"58) Kagiya, T.; Sumida, Y.; Inoue, T. Evaluation of the activation energies of radical substitution reactions in the gaseous phase. II. An approximate formula with two constants. Bull. Chem. Soc. 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