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Original Articles

Comprehensive Study on Vitamin C Equivalent Antioxidant Capacity (VCEAC) of Various Polyphenolics in Scavenging a Free Radical and its Structural Relationship

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Pages 253-273 | Published online: 10 Aug 2010

REFERENCES

  • Nordberg , J. and Arnér , E. S. J. 2001 . Reactive oxygen species, antioxidants, and the mammalian thioredoxin system . Free Radic. Biol. Med. , 31 : 1287 – 1312 .
  • Patel , M. N. 2002 . Oxidative stress, mitochondrial dysfunction, and epilepsy . Free Radic. Res. , 36 : 1139 – 1146 .
  • Frankel , E. N. 1993 . In search of better methods to evaluate natural antioxidants and oxidative stability in food lipids . Trends Food Sci. Technol. , 4 : 220 – 225 .
  • Dehmlow , C. , Murawski , N. and de Groot , H. 1996 . Scavenging of reactive oxygen species and inhibition of arachidonic acid metabolism by silibinin in human cells . Life Sci. , 58 : 1591 – 1600 .
  • Bogdanov , M. , Brown , R. H. Jr. , Matson , W. , Smart , R. , Hayden , D. , O′Donnell , H. , Beal , M. F. and Cudkowicz , M. 2000 . Increased oxidative damage to DNA in ALS patients . Free Radic. Biol. Med. , 29 : 652 – 658 .
  • Heo , M. Y. , Sohn , S. J. and Au , W. W. 2001 . Anti-genotoxicity of galangin as a cancer chemopreventive agent candidate . Mutat. Res. , 488 : 135 – 150 .
  • Sezto , Y.-T. and Benzie , I. F. F. 2002 . Effects of dietary antioxidants on human DNA ex vivo . Free Radic. Res. , 36 : 113 – 118 .
  • Joshipura , K. J. , Ascherio , A. , Manson , J. E. , Stampfer , M. J. , Rimm , E. B. , Speizer , F. E. , Hennekens , C. H. , Spiegelman , D. and Willett , W. C. 1999 . Fruit and vegetable intake in relation to risk of ischemic stroke . JAMA , 282 : 1233 – 1239 .
  • Truswell , A. S. 1995 . Recommended dietary allowances now in molar units . Am. J. Clin. Nutr. , 61 : 866
  • Rock , C. L. , Jacob , R. A. and Bowen , P. E. 1996 . Update on the biological characteristics of the antioxidant micronutrients: Vitamin C, vitamin E, and the carotenoids . J. Am. Diet. Assoc. , 96 : 693 – 702 .
  • Gutteridge , J. M. C. 1994 . Biological origin of free radicals, and mechanisms of antioxidant protection . Chem.-Biol. Interact. , 91 : 133 – 140 .
  • Camougrand , N. and Rigoulet , M. 2001 . Aging and oxidative stress: Studies of some genes involved both in aging and in response to oxidative stress . Respir. Physiol. , 128 : 393 – 401 .
  • Lee , K. W. , Lee , H. J. , Kang , K.-S. and Lee , C. Y. 2002 . Preventive effects of vitamin C on carcinogenesis . Lancet , 359 : 172
  • Kim , D.-O. , Lee , K. W. , Lee , H. J. and Lee , C. Y. 2002 . Vitamin C equivalent antioxidant capacity (VCEAC) of phenolic phytochemicals . J. Agric. Food Chem. , 50 : 3713 – 3717 .
  • Scott , S. L. , Chen , W.-J. , Bakac , A. and Espenson , J. H. 1993 . Spectroscopic parameters, electrode potentials, acid ionization constants, and electron exchange rates of the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) radicals and ions . J. Phys. Chem. , 97 : 6710 – 6714 .
  • van den Berg , R. , Haenen , G. R. M. M. , van den Berg , H. and Bast , A. 1999 . Applicability of an improved Trolox equivalent antioxidant capacity (TEAC) assay for evaluation of antioxidant capacity measurements of mixtures . Food Chem. , 66 : 511 – 517 .
  • Miller , N. J. , Sampson , J. , Candeias , L. P. , Bramley , P. M. and Rice-Evans , C. A. 1996 . Antioxidant activities of carotenes and xanthophylls . FEBS Lett. , 384 : 240 – 242 .
  • Rice-Evans , C. and Miller , N. J. 1994 . Total antioxidant status in plasma and body fluids . Methods Enzymol. , 234 : 279 – 293 .
  • Arena , E. , Fallico , B. and Maccarone , E. 2001 . Evaluation of antioxidant capacity of blood orange juices as influenced by constituents, concentration process and storage . Food Chem. , 74 : 423 – 427 .
  • Proteggente , A. R. , Pannala , A. S. , Paganga , G. , van Buren , L. , Wagner , E. , Wiseman , S. , van de Put , F. , Dacombe , C. and Rice-Evans , C. A. 2002 . The antioxidant activity of regularly consumed fruit and vegetables reflects their phenolic and vitamin C composition . Free Radic. Res. , 36 : 217 – 233 .
  • Sellappan , S. , Akoh , C. C. and Krewer , G. 2002 . Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries . J. Agric. Food Chem. , 50 : 2432 – 2438 .
  • Kim , D.-O. , Jeong , S. W. and Lee , C. Y. 2003 . Antioxidant capacity of phenolic phytochemicals from various cultivars of plums . Food Chem. , 81 : 321 – 326 .
  • Friedman , M. 1996 . Food browning and its prevention: An overview . J. Agric. Food Chem. , 44 : 631 – 653 .
  • Möller , B. and Herrmann , K. 1983 . Quinic acid esters of hydroxycinnamic acids in stone and pome fruit . Phytochemistry , 22 : 477 – 481 .
  • Herrmann , K. 1989 . Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods . Crit. Rev. Food Sci. Nutr. , 28 : 315 – 347 .
  • Horvat , R. J. , Chapman , G. W. Jr. , Senter , S. D. , Robertson , J. A. , Okie , W. R. and Norton , J. D. 1992 . Comparison of the volatile compounds from several commercial plum cultivars . J. Sci. Food Agric. , 60 : 21 – 23 .
  • Middleton , E. Jr. and Kandaswami , C. 1994 . “ The impact of plant flavonoids on mammalian biology: Implications for immunity, inflammation and cancer ” . In The flavonoids: Advances in research since , Edited by: Harborne , J. B. 619 – 652 . London : Champman & Hall . pp
  • Lee , C. Y. 2000 . “ Phenolic compounds ” . In Encyclopedia of food science and technology , Edited by: Francis , F. J. 1872 – 1881 . New York : Wiley . pp
  • Torel , J. , Cillard , J. and Cillard , P. 1986 . Antioxidant activity of flavonoids and reactivity with peroxy radical . Phytochemistry , 25 : 383 – 385 .
  • Muldoon , M. F. and Kritchevsky , S. B. 1996 . Flavonoids and heart disease . Brit. Med. J. , 312 : 458 – 459 .
  • Agullo , G. , Gamet-Payrastre , L. , Manenti , S. , Viala , C. , Rémésy , C. , Chap , H. and Payrastre , B. 1997 . Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: A comparison with tyrosine kinase and protein kinase C inhibition . Biochem. Pharmacol. , 53 : 1649 – 1657 .
  • Meyer , A. S. , Yi , O.-S. , Pearson , D. A. , Waterhouse , A. L. and Frankel , E. N. 1997 . Inhibition of human low-density lipoprotein oxidation in relation to composition of phenolic antioxidants in grapes (Vitis vinifera) . J. Agric. Food Chem. , 45 : 1638 – 1643 .
  • Tereschuk , M. L. , Riera , M. V. Q. , Castro , G. R. and Abdala , L. R. 1997 . Antimicrobial activity of flavonoids from leaves of Tagetes minuta . J. Ethnopharmacol. , 56 : 227 – 232 .
  • Park , J. C. , Hur , J. M. , Park , J. G. , Kim , H. J. , Kang , K. H. , Choi , M. R. and Song , S. H. 2000 . Inhibitory effects of various edible plants and flavonoids from the leaves of Cedrela sinensis on human immunodeficiency virus type 1 protease . J. Food Sci. Nutr. , 5 : 170 – 173 .
  • Lee , G.-H. , Shim , C.-J. , Chang , Y.-I. , Choi , S.-H. , Oh , H.-R. and Oh , M.-J. 2001 . Antimicrobial activities of (−)epicatechin from Ulmus davidiana var. japonica cortex . J. Food Sci. Nutr. , 6 : 230 – 234 .
  • Ryu , B. H. 2002 . Antioxidative activity of flavonoid on oxidation of human low density lipoprotein induced by macrophages and copper . Food Sci. Biotechnol. , 11 : 84 – 88 .
  • Fairfield , K. M. and Fletcher , R. H. 2002 . Vitamins for chronic disease prevention in adults . JAMA , 287 : 3116 – 3126 .
  • Yanishlieva-Maslarova , N. V. 2001 . “ Inhibiting oxidation ” . In Antioxidants in food: Practical applications , Edited by: Pokorny , J. , Yanishlieva , N. and Gordon , M. H. 22 – 70 . Cambridge, , England : Woodhead Publishing Limited . pp
  • Burton , G. W. and Ingold , K. U. 1984 . β -Carotene: An unusual type of lipid antioxidant . Science , 224 : 569 – 573 .
  • Everett , S. A. , Dennis , M. F. , Patel , K. B. , Maddix , S. , Kundu , S. C. and Willson , R. L. 1996 . Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β -carotene . J. Biol. Chem. , 271 : 3988 – 3994 .
  • Rice-Evans , C. A. , Miller , N. J. and Paganga , G. 1996 . Structure-antioxidant activity relationships of flavonoids and phenolic acids . Free Radic. Biol. Med. , 20 : 933 – 956 .
  • Cuvelier , M.-E. , Richard , H. and Berset , C. 1992 . Comparison of the antioxidative activity of some acid-phenols: Structure-activity relationship . Biosci. Biotechnol. Biochem. , 56 : 324 – 325 .
  • Heijnen , C. G. M. , Haenen , G. R. M. M. , van Acker , F. A. A. , van der Vijgh , W. J. F. and Bast , A. 2001 . Flavonoids as peroxynitrite scavengers: The role of the hydroxyl groups . Toxicol. In Vitro , 15 : 3 – 6 .
  • Heijnen , C. G. M. , Haenen , G. R. M. M. , Oostveen , R. M. , Stalpers , E. M. and Bast , A. 2002 . Protection of flavonoids against lipid peroxidation: The structure activity relationship revisited . Free Radic. Res. , 36 : 575 – 581 .
  • Natella , F. , Nardini , M. , Di Felice , M. and Scaccini , C. 1999 . Benzoic and cinnamic acid derivatives as antioxidants: Structure-activity relation . J. Agric. Food Chem. , 47 : 1453 – 1459 .
  • Fukumoto , L. R. and Mazza , G. 2000 . Assessing antioxidant and prooxidant activities of phenolic compounds . J. Agric. Food Chem. , 48 : 3597 – 3604 .
  • Wang , H. , Cao , G. and Prior , R. L. 1997 . Oxygen radical absorbing capacity of anthocyanins . J. Agric. Food Chem. , 45 : 304 – 309 .
  • Tsuda , T. , Watanabe , M. , Ohshima , K. , Norinobu , S. , Choi , S.-W. , Kawakishi , S. and Osawa , T. 1994 . Antioxidative activity of the anthocyanin pigments cyanidin 3-O-β -D-glucoside and cyanidin . J. Agric. Food Chem. , 42 : 2407 – 2410 .
  • Rezk , B. M. , Haenen , G. R. M. M. , van der Vijgh , W. J. F. and Bast , A. 2002 . The antioxidant activity of phloretin: The disclosure of a new antioxidant pharmacophore in flavonoids . Biochem. Biophys. Res. Commu. , 295 : 9 – 13 .
  • Cholbi , M. R. , Paya , M. and Alcaraz , M. J. 1991 . Inhibitory effects of phenolic compounds on CCl4-induced microsomal lipid peroxidation . Experientia , 47 : 195 – 199 .
  • Bors , W. , Heller , W. , Michel , C. and Saran , M. 1990 . Flavonoids as antioxidants: Determination of radical-scavenging efficiencies . Methods Enzymol. , 186 : 343 – 355 .
  • Chen , C.-W. and Ho , C.-T. 1995 . Antioxidant properties of polyphenols extracted from green and black teas . J. Food Lipids , 2 : 35 – 46 .
  • Dixon , R. A. and Steele , C. L. 1999 . Flavonoids and isoflavonoids-a gold mine for metabolic engineering . Trends Plant Sci. , 4 : 394 – 400 .
  • Mathiesen , L. , Malterud , K. E. and Sund , R. B. 1997 . Hydrogen bond formation as basis for radical scavenging activity: A structure-activity study of C-methylated dihydrochalcones from Myrica gale and structurally related acetophenones . Free Radic. Biol. Med. , 22 : 307 – 311 .
  • Dziedzic , S. Z. and Hudson , B. J. F. 1983 . Polyhydroxy chalcones and flavanones as antioxidants for edible oils . Food Chem. , 12 : 205 – 212 .
  • van Acker , S. A. B. E. , van den Berg , D.-J. , Tromp , M. N. J. L. , Griffioen , D. H. , van Bennekom , W. P. , van der Vijgh , W. J. F. and Bast , A. 1996 . Structural aspects of antioxidant activity of flavonoids . Free Radic. Biol. Med. , 20 : 331 – 342 .
  • Silva , M. M. , Santos , M. R. , Caroço , G. , Rocha , R. , Justino , G. and Mira , L. 2002 . Structure-antioxidant activity relationships of flavonoids: A re-examination . Free Radic. Res. , 36 : 1219 – 1227 .
  • Foti , M. , Piattelli , M. , Baratta , M. T. and Ruberto , G. 1996 . Flavonoids, coumarins, and cinnamic acids as antioxidants in a micellar system. structure-activity relationship . J. Agric. Food Chem. , 44 : 497 – 501 .
  • Hudson , B. J. F. and Lewis , J. I. 1983 . Polyhydroxy flavonoid antioxidants for edible oils: Structural criteria for activity . Food Chem. , 10 : 47 – 55 .
  • Husain , S. R. , Cillard , J. and Cillard , P. 1987 . Hydroxyl radical scavenging activity of flavonoids . Phytochemistry , 26 : 2489 – 2491 .
  • Haenen , G. R. M. M. , Paquay , J. B. G. , Korthouwer , R. E. M. and Bast , A. 1997 . Peroxynitrite scavenging by flavonoids . Biochem. Biophys. Res. Commu. , 236 : 591 – 593 .
  • van Acker , S. A. B. E. , de Groot , M. J. , van den Berg , D.-J. , Tromp , M. N. J. L. , den Kelder , G. D.-O. , van der Vijgh , W. J. F. and Bast , A. 1996 . A quantum chemical explanation of the antioxidant activity of flavonoids . Chem. Res. Toxicol. , 9 : 1305 – 1312 .
  • Cotelle , N. , Bernier , J.-L. , Catteau , J.-P. , Pommery , J. , Wallet , J.-C. and Gaydou , E. M. 1996 . Antioxidant properties of hydroxy-flavones . Free Radic. Biol. Med. , 20 : 35 – 43 .
  • Pannala , A. S. , Chan , T. S. , O′Brien , P. J. and Rice-Evans , C. A. 2001 . Flavonoid B-ring chemistry and antioxidant activity: Fast reaction kinetics . Biochem. Biophys. Res. Commu. , 282 : 1161 – 1168 .
  • Cao , G. , Sofic , E. and Prior , R. L. 1997 . Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships . Free Radic. Biol. Med. , 22 : 749 – 760 .
  • Choi , Y.-S. , Lee , B.-H. , Kim , J.-H. and Kim , N.-S. 2000 . Concentration of phytoestrogens in soybeans and soybean products in Korea . J. Sci. Food Agric. , 80 : 1709 – 1712 .
  • Barnes , S. , Boersma , B. , Patel , R. , Kirk , M. , Darley-Usmar , V. M. , Kim , H. and Xu , J. 2000 . Isoflavonoids and chronic disease: Mechanisms of action . Biofactors , 12 : 209 – 215 .
  • Dziedzic , S. Z. and Hudson , B. J. F. 1983 . Hydroxy isoflavones as antioxidants for edible oils . Food Chem. , 11 : 161 – 166 .
  • Hodgson , J. M. , Croft , K. D. , Puddey , I. B. , Mori , T. A. and Beilin , L. J. 1996 . Soybean isoflavonoids and their metabolic products inhibit in vitro lipoprotein oxidation in serum . J. Nutr. Biochem. , 7 : 664 – 669 .
  • Camire , M. E. and Dougherty , M. P. 1998 . Added phenolic compounds enhance lipid stability in extruded corn . J. Food Sci. , 63 : 516 – 518 .
  • Murcia , M. A. and Martínez-Tomé , M. 2001 . Antioxidant activity of resveratrol compared with common food additives . J. Food Prot. , 64 : 379 – 384 .
  • Chen , J. H. and Ho , C.-T. 1997 . Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds . J. Agric. Food Chem. , 45 : 2374 – 2378 .
  • Goldberg , D. M. and Soleas , G. J. 1999 . Analysis of antioxidant wine polyphenols by high-performance liquid chromatography . Methods Enzymol. , 299 : 122 – 137 .
  • Nielsen , M. , Ruch , R. J. and Vang , O. 2000 . Resveratrol reverses tumor-promoter-induced inhibition of gap-junctional intercellular communication . Biochem. Biophys. Res. Commu. , 275 : 804 – 809 .
  • Sánchez-Moreno , C. , Jiménez-Escrig , A. and Saura-Calixto , F. 2000 . Study of low-density lipoprotein oxidizability indexes to measure the antioxidant activity of dietary polyphenols . Nutr. Res. , 20 : 941 – 953 .
  • Kapadia , G. J. , Azuine , M. A. , Tokuda , H. , Takasaki , M. , Mukainaka , T. , Konoshima , T. and Nishino , H. 2002 . Chemopreventive effect of resveratrol, sesamol, sesame oil and sunflower oil in the Epstein-Barr virus early antigen activation assay and the mouse skin two-stage carcinogenesis . Pharmacol. Res. , 45 : 499 – 505 .
  • Wada , L. and Ou , B. 2002 . Antioxidant activity and phenolic content of Oregon caneberries . J. Agric. Food Chem. , 50 : 3495 – 3500 .
  • Mohamed , H. M. A. and Awatif , I. I. 1998 . The use of sesame oil unsaponifiable matter as a natural antioxidant . Food Chem. , 62 : 269 – 276 .
  • Cabrini , L. , Barzanti , V. , Cipollone , M. , Fiorentini , D. , Grossi , G. , Tolomelli , B. , Zambonin , L. and Landi , L. 2001 . Antioxidants and total peroxyl radical-trapping ability of olive and seed oils . J. Agric. Food Chem. , 49 : 6026 – 6032 .
  • Okazaki , K. , Kawazoe , K. and Takaishi , Y. 2002 . Human platelet aggregation inhibitors from thyme (Thymus vulgaris L.) . Phytother. Res. , 16 : 398 – 399 .
  • Aeschbach , R. , Löliger , J. , Scott , B. C. , Murcia , A. , Butler , J. , Halliwell , B. and Aruoma , O. I. 1994 . Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol . Food Chem. Toxic. , 32 : 31 – 36 .
  • Yanishlieva , N. , Marinova , E. M. , Gordon , M. H. and Raneva , V. G. 1999 . Antioxidant activity and mechanism of action of thymol and carvacrol in two lipid systems . Food Chem. , 64 : 59 – 66 .
  • Hudaib , M. , Speroni , E. , Di Pietra , A. M. and Cavrini , V. 2002 . GC/MS evaluation of thyme (Thymus vulgaris L.) oil composition and variations during the vegetative cycle . J. Pharm. Biomed. Anal. , 29 : 691 – 700 .
  • Lee , K.-G. and Shibamoto , T. 2001 . Antioxidant property of aroma extract isolated from clove buds [Syzygium aromaticum (L.) Merr. et Perry] . Food Chem. , 74 : 443 – 448 .

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