Superoxide radical- and peroxynitrite-scavenging activity of anthocyanins; structure-activity relationship and their synergism

References

• Matsumoto H, Hanamura S, Kawakami T, Sato Y, Hirayama M. Preparative-scale isolation of four anthocyanin components of black currant (Ribes nigrum L.) Fruits. J Agric Food Chem 2001; 49: 1541–1545
   PubMed Web of Science ®Google Scholar
• Wu X, Prior RL. Systematic identification and characterization of anthocyanins by HPLC-ESI-MS/MS in common foods in the United States: Fruits and berries. J Agric Food Chem 2005; 53: 2589–2599
   PubMed Web of Science ®Google Scholar
• Wu X, Prior RL. Identification and characterization of anthocyanins by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in common foods in the United States: Vegetables, nuts, and grains. J Agric Food Chem 2005; 53: 3101–3113
   PubMed Web of Science ®Google Scholar
• Scalbert A, Williamson G. Dietary intake and bioavailablity of polyphenols. J Nutr 2000; 130: 2073S–2085S
   PubMed Web of Science ®Google Scholar
• Clifford MN. Anthocyanins- nature, occurrence and dietary burden. J Sci Food Agric 2000; 80: 1063–1072
   Web of Science ®Google Scholar
• Zheng W, Wang SY. Oxygen radical absorbing capacity of phenolics in blueberries, cranberries, chokeberries, and lingonberries. J Agric Food Chem 2003; 51: 502–509
   PubMed Web of Science ®Google Scholar
• De Beer D, Joubert E, Gelderblom WC, Manley M. Antioxidant activity of South African red and white cultivar wines: Free radical scavenging. J Agric Food Chem 2003; 51: 902–909
   PubMed Web of Science ®Google Scholar
• Matsumoto H, Nakamura Y, Tachibanaki S, Kawamura S, Hirayama M. Stimulatory effect of cyanidin 3-glycosides on the regeneration of rhodopsin. J Agric Food Chem 2003; 51: 3560–3563
   PubMed Web of Science ®Google Scholar
• Meiers S, Kemeny M, Weyand U, Gastpar R, Von Angerer E, Marko D. The anthocyanidins cyanidin and delphinidin are potent inhibitors of the epidermal growth-factor receptor. J Agric Food Chem 2001; 49: 958–962
   PubMed Web of Science ®Google Scholar
• Kamei H, Kojima T, Hasegawa M, Koide T, Umeda T, Yukawa T, Terabe K. Suppression of tumour cell growth by anthocyanins. Cancer Invest 1995; 13: 590–594
   PubMed Web of Science ®Google Scholar
• Wang K, Nair MG, Strasburg GM, Chang YC, Booren AM, Gray I, DeWitt DL. Antioxidant and anti-inflammatory activities of anthocyanins and their aglycon, cyanindin, from tart cherries. J Nat Prod 1999; 62: 294–296
   PubMed Web of Science ®Google Scholar
• Schnackenberg CG. Physiological and pathophysiological roles of oxygen radicals in the renal microvasculature. Am J Physiol Regul Integr Comp Physiol 2002; 282: 335–342
   Google Scholar
• Caro AA, Cederbaum IA. Oxidative stress, toxicology and pharmacology of CYP2E1. Annu Rev Pharmacol Toxicol 2004; 44: 27–42
   PubMed Web of Science ®Google Scholar
• Urquiaga I, Leighton F. Plant polyphenol antioxidants and oxidative stress. Biol Res 2000; 33(2)
   PubMedGoogle Scholar
• Eiserich JP, Hristova M, Cross CE, Jones AD, Freeman BA, Halliwell B. Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 1998; 391: 393–397
   PubMed Web of Science ®Google Scholar
• Good PF, Hsu A, Werner P, Perl DP, Olanow CW. Protein nitration in Parkinson's disease. J Neuropathol Exp Neurol 1998; 57: 338–342
   PubMed Web of Science ®Google Scholar
• Smith MA, Richey Harris PL, Sayre LM, Beckman JS, Perry G. Widespread peroxynitrite-mediated damage in Alzheimer's disease. J Neurosci 1997; 17: 2653–2657
   PubMed Web of Science ®Google Scholar
• Abe K, Pan LH, Watanabe M, Konno H, Kato T, Hoyama Y. Upregulation of protein-tyrosine nitration in the anterior horn cells of amyotrophic lateral sclerosis. Neurol Lett 1997; 19: 124–128
   Google Scholar
• Pereira GK, Donate PM, Galembeck SE. Effects of substitution for hydroxyl in the B-ring of the flavylium cation. J Mol Struct 1997; 392: 169–179
   Web of Science ®Google Scholar
• Rice-Evans CA, Miller NJ, Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 1996; 20: 933–956
   PubMed Web of Science ®Google Scholar
• Wang H, Cao G, Prior RL. Oxygen radical absorbing capacity of anthocyanins. J Agric Food Chem 1997; 45: 304–309
   Web of Science ®Google Scholar
• Noda Y, Kaneyuki T, Igarashi K, Mori A, Packer L. Antioxidant activity of nasunin, an anthocyanin in eggplant peels. Toxicol 2000; 148: 119–123
   PubMed Web of Science ®Google Scholar
• Tsuda T, Kato Y, Osawa T. Mechanism for the peroxynitrite scavenging activity by anthocyanins. FEBS Lett 2000; 484: 207–210
   PubMed Web of Science ®Google Scholar
• Noda Y, Kaneyuki T, Igarashi K, Mori A, Packer L. Antioxidant activities of pomegranate fruit extract and its anthocyanidins: Delphinidin, cyanidin, and pelargonidin. J Agric Food Chem 2002; 50: 166–171
   PubMed Web of Science ®Google Scholar
• Pannala A, Chan T, Brien P, Rice-Evans C. Flavonoid B-ring chemistry and antioxidant activity: Fast reaction kinetics. Biochem Biophys Res Commun 2001; 282: 1161–1168
   PubMed Web of Science ®Google Scholar
• Ichiyanagi T, Hatano Y, Matsugo S, Konishi T. Kinetic comparisons of anthocyanin reactivities to 2,2′ -Azobis(2-amidinopropane) (AAPH) radicals, hydrogen peroxide and tert-Buthylhydroperoxide by capillary zone electrophoresis. Biol Pharm Bull 2004; 52: 434–438
   Google Scholar
• Ichiyanagi T, Hatano Y, Matsugo S, Konishi T. Simultaneous comparison of relative reactivities of twelve major anthocyanins in bilberry towards reactive nitrogen species. Biol Pharm Bull 2004; 52: 1312–1315
   Google Scholar
• Satue'-Gracia MT, Heinonen M, Frankel EN. Anthocyanins as antioxidants on human low-density lipoprotein and lecithin-liposome systems. J Agric Food Chem 1997; 45: 3362–3367
   Google Scholar
• Tsuda T, Horio F, Osawa T. Dietary cyanidin 3-O-beta-d-glucoside increases ex vivo oxidation resistance of serum in rats. Lipids 1998; 33: 583–588
   PubMed Web of Science ®Google Scholar
• Kähkönen MP, Heinonen M. Antioxidant activity of anthocyanins and their aglycons. J Agric Food Chem 2003; 51: 628–633
   PubMed Web of Science ®Google Scholar
• Matsumoto H, Nakamura Y, Hirayama M, Yoshiki Y, Okubo K. Antioxidant activity of black currant anthocyanin aglycons and their glycosides measured by chemiluminescence in a neutral pH region and in human plasma. J Agric Food Chem 2002; 50: 5034–5037
   PubMed Web of Science ®Google Scholar
• Garcia-Alonso M, Rimbach G, Sasai M, Nakahara M, Matsugo S, Uchida Y, Rivas-Gonzalo JC, De Pascual-Teresa S. Electron spin resonance spectroscopy studies on the free radical scavenging activity of wine anthocyanins and pyranoanthocyanins. Mol Nutr Food Res 2005; 49: 1112–1119
   PubMed Web of Science ®Google Scholar
• Ichiyanagi T, Kashiwada Y, Ikeshiro Y, Hatano Y, Shida Y, Horie M, Matsugo S, Konishi T. Complete assignment of bilberry (Vaccinium myrtillus L.) anthocyanins separated by capillary zone electrophoresis. Chem Pharm Bull 2004; 52: 226–229
   PubMed Web of Science ®Google Scholar
• Ichiyanagi T, Rahman MM, Kashiwada Y, Ikeshiro Y, Shida Y, Hatano Y, Hitoshi M, Hirayama M, Tsuda T, Konishi T. Absorption and metabolism of delphinindin 3-O-β-d-glucoside in rats. Free Radic Biol Med 2004; 36: 930–937
   PubMed Web of Science ®Google Scholar
• Ichikawa H, Ichiyanagi T, Xu B, Yoshi Y, Nakajima M, Konishi T. Antioxidant activity of anthocyanin extract from purple black rice. J Med Food 2001; 4: 211–218
   PubMedGoogle Scholar
• Beckman JS, Chen J, Ischiropoulos H, Crow JP. Oxidative chemistry of peroxynitrite. Methods Enzymol 1994; 233: 229–240
   PubMed Web of Science ®Google Scholar
• Kerry N, Rice-Evans C. Peroxynitrite oxidizes catechols to O-quinones. FEBS Lett 1998; 437: 167–171
   PubMed Web of Science ®Google Scholar
• Wu X, Cao G, Prior RL. Absorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. J Nutr 2002; 132: 1865–1871
   PubMed Web of Science ®Google Scholar
• Matsumoto H, Inaba H, Kishi M, Tominaga S, Hirayama M, Tsuda T. Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J Agric Food Chem 2001; 49: 1546–1551
   PubMed Web of Science ®Google Scholar
• Ichiyanagi T, Shida Y, Rahman MM, Hatano Y, Matsumoto H, Hirayama M, Konishi T. Metabolic pathway of cyanidin 3-O-beta-d-glucopyranoside in rats. J Agric Food Chem 2005; 53: 145–150
   PubMed Web of Science ®Google Scholar
• Ichiyanagi T, Shida Y, Rahman MM, Hatano Y, Konishi T. Extended glucuronidation is another major path of cyanidin 3-O-beta-d-glucopyranoside metabolism in rats. J Agric Food Chem 2005; 53: 7312–7319
   PubMed Web of Science ®Google Scholar
• Felgines C, Talavéra S, Gonthier MP, Texier O, Scalbert A, Lamaison JL, Rémésy C. Strawberry anthocyanins are recovered in urine as glucuro- and sulfoconjugates in humans. J Nutr 2003; 133: 1296–1301
   PubMed Web of Science ®Google Scholar
• Francis FJ. Food colorants: Anthocyanins. Crit Rev Food Sci Nutr 1989; 28: 273–314
   PubMed Web of Science ®Google Scholar
• Lapidot T, Harel S, Akiri B, Granit R, Kanner J. pH-Dependent forms of red wine anthocyanins as antioxidants. J Agric Food Chem 1999; 47: 67–70
   PubMed Web of Science ®Google Scholar
• Hayashi T, Sawa K, Kawasaki M, Arisawa M, Shimizu M, Morita N. Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod 1988; 51: 345–348
   PubMed Web of Science ®Google Scholar
• Pannala AS, Razaq R, Halliwell B, Singh S, Rice-Evans CA. Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: Nitration or electron donation. Free Radic Biol Med 1998; 24: 594–606
   PubMed Web of Science ®Google Scholar
• Borkowski T, Szymusiak H, Gliszczynska-S, Rietjens IMCM, Tyrakowska B. Radical scavenging capacity of wine anthocyanins is strongly pH-dependent. J Agric Food Chem 2005; 53: 5526–5534
   PubMed Web of Science ®Google Scholar
• Arteel GE, Sies H. Protection against perocynitrite by cocoa polyphenol oligomers. FEBS Lett 1999; 462: 167–170
   PubMed Web of Science ®Google Scholar
• Arteel GE, Schroeder P, Sies H. Reactions of peroxynitrite with cocoa procyanidin oligomers. J Nutr 2000; 130: 2100S–2104S
   PubMed Web of Science ®Google Scholar