339
Views
12
CrossRef citations to date
0
Altmetric
Original Article

Oxidation of flavonoids by hypochlorous acid: reaction kinetics and antioxidant activity studies

, &
Pages 898-908 | Received 08 Jan 2016, Accepted 22 May 2016, Published online: 07 Jul 2016

References

  • Pietta P-G. Flavonoids as antioxidants. J Nat Prod 2000;63:1035–1042.
  • 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.
  • Prochazkova D, Bousova I, Wilhelmova N. Antioxidant and prooxidant properties of flavonoids. Fitoterapia 2011;82:513–523.
  • Morris JC. The acid ionization constant of HOCl from 5 to 35°. J Phys Chem 1966;70:3798–3805.
  • Hawkins CL, Pattison DI, Davies MJ. Hypochlorite-induced oxidation of amino acids, peptides and proteins. Amino Acids 2003;25:259–274.
  • Panasenko OM, Gorudko IV, Sokolov AV. Hypochlorous acid as a precursor of free radicals in living systems. Biochemistry Mosc 2013;78:1466–1489.
  • Pullar JM, Vissers MCM, Winterbourn CC. Living with a killer: the effects of hypochlorous acid on mammalian cells. IUBMB Life 2000;50:259–266.
  • Rees MD, Kennet EC, Whiteloch JM, Davies MJ. Oxidative damage to extracellular matrix and its role in human pathologies. Free Radic Biol Med 2008;44:1973–2001.
  • Weiss SJ. Tissue destruction by neutrophils. N Engl J Med 1989;320:365–376.
  • Storkey C, Davies MJ, Pattison DI. Reevaluation of the rate constants for the reaction of hypochlorous acid (HOCl) with cysteine, methionine, and peptide derivatives using a new competition kinetic approach. Free Radic Biol Med 2014;73:60–66.
  • Firuzi O, Mladenka P, Petrucci R, Marrosu G, Saso L. Hypochlorite scavenging activity of flavonoids. J Pharm Pharmacol 2004;56:801–807.
  • Selloum L, Djelili H, Sebihi L, Arnhold J. Scavenger effect of flavonols on HOCl-induced luminol chemiluminescence. Luminescence 2004;19:199–204.
  • Boersma BJ, Patel RP, Kirk M, Jackson PL, Muccio D, Darley-Usmar VM, Barnes S. Chlorination and nitration of soy isoflavones. Arch Biochem Biophys 1999;368:265–275.
  • Binsack R, Boersma BJ, Patel RP, Kirk M, White CR, Darley-Usmar V, et al. Enhanced antioxidant activity after chlorination of quercetin by hypochlorous acid. Alcohol Clin Exp Res 2001;25:434–443.
  • Kawai Y, Matsui Y, Kondo H, Morinaga H, Uchida K, Miyoshi N, et al. Galloylated catechins as potent inhibitors of hypochlorous-acid-induced DNA damage. Chem Res Toxicol 2008;21:1407–1414.
  • Gebicka L, Banasiak E. Hypochlorous acid-induced heme damage of hemoglobin and its inhibition by flavonoids. Toxicol In Vitro 2012;26:924–929.
  • Krych J, Gebicki JL, Gebicka L. Flavonoid-induced conversion of catalase to its inactive form-Compound II. Free Radic Res 2014;48:1334–1341.
  • Mercader-Ros MT, Lucas-Abellan C, Gabaldon JA, Fortea MI, Martinez-Cacha A, Nunez-Delicado E. Kaempferol complexation in cyclodextrins at basic pH. J Agric Food Chem 2010;58:4675–4680.
  • Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 1999;26:1231–1237.
  • Mabry TJ, Markham KR, Thomas MB. The systematic identification of flavonoids. Berlin-Heidelberg-New York: Springer-Verlag; 1970.
  • Alvarez-Diduk R, Ramirez-Silva MT, Galano A, Merkoci A. Deprotonation mechanism and acidity constants in aqueous solution of flavonols: a combined experimental and theoretical study. J Phys Chem B 2013;117:12347–12359.
  • Dangles O, Fargeix G, Dufour C. One-electron oxidation of quercetin and quercetin derivatives in protic and non protic media. J Chem Soc Perkin Trans 2 1999;1387–1395.
  • Lide DR. CRC handbook of chemistry and physics. 86th ed. New York: Taylor & Francis Group; 2005–2006.
  • Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J Phys Chem Ref Data 1989;18:1637–1755.
  • Folkes LK, Candeias LP, Wardman P. Kinetics and mechanisms of hypochlorous acid reactions. Arch Biochem Biophys 1995;323:120–126.
  • Armesto XL, Canle M, Fernandez JMI, Garcia MV, Santoballa JA. First steps in the oxidation of sulfur-containing amino acids by hypohalogenation: very fast generation of intermediate sulfenyl halides and halosulfonium cations. Tetrahedron 2000;56:1103–1109.
  • Jovanovic SV, Steenken S, Tosic M, Marjanovic M, Simic MG. Flavonoids as antioxidants. J Am Chem Soc 1994;116:4846–4851.
  • Lemanska K, Szymusiak H, Tyrakowska B, Zielinski R, Soffers AEMF, Rietjens IMCM. The influence of pH on antioxidant properties and the mechanism of antioxidant action of hydroxyflavones. Free Radic Biol Med 2001;31:869–881.
  • Arshad N, Janjua NK, Ahmed S, Khan AY, Skibsted LH. Electrochemical investigations of antioxidant interactions with radical anion and dianion of 1,3-dinitrobenzene. Electrochem Acta 2009;54:6184–6189.
  • Dangles O, Dufour C, Bret S. Flavonol-serum albumin complexation. Two-electron oxidation of flavonols and their complexes with serum albumin. J Chem Soc Perkin Trans 2 1999;737–744.
  • Taubert D, Breitenbach T, Lazar A, Censarek P, Harlfinger S, Berkels R, et al. Reaction rate constants of superoxide scavenging by plant antioxidants. Free Radic Biol Med 2003;35:1599–1607.
  • Candeias LP, Patel KB, Stratford MRL, Wardman P. Free hydroxyl radicals are formed on reactionbetween the neutrophil-derived species superoxide anion and hypochlorous acid. FEBS Lett 1993;333:151–153.
  • Held AM, Halko DJ, Hurst JK. Mechanisms of chlorine oxidation of hydrogen peroxide. J Am Chem Soc 1978;100:5732–5740.
  • Nagai S, Ohara K, Mukai K. Kinetic study of the quenching reaction of singlet oxygen by flavonoids in ethanol solution. J Phys Chem B 2005;109:4234–4240.
  • Deborde M, von Gunten U. Reactions of chlorine with inorganic and organic compounds during water treatment – kinetics and mechanisms: a critical review. Water Res 2008;42:13–51.
  • Arnhold J, Mueller S, Arnold K, Sonntag K. Mechanisms of inhibition of chemiluminescence in the oxidation of luminal by sodium hypochlorite. J Biolumin Chemilumin 1993;6:307–313.
  • Pannala AS, Chan TS, O’Brien PJ, Rice-Evans CA. Flavonoid B-ring chemistry and antioxidant activity: fast reaction kinetics. Biochem Biophys Res Commun 2001;282:1161–1168.
  • Gulsen A, Makris DP, Kefalas P. Biomimetic oxidation of quercetin: isolation of a naturally occurring quercetin heterodimer and evaluation of its in vitro antioxidant properties. Food Res Int 2007;40:7–14.
  • Wong-Paz JE, Muniz-Marquez DB, Aguilar CN, Sotin H and Guyot S. Enzymatic synthesis, purification and in vitro antioxidant capacity of polyphenolic oxidation products from apple juice. LWT Food Sci Technol 2015;64:1091–1098.
  • Manach C, Williamson G, Morand C, Scalbert A, Remesy C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr 2005;81:230S–242S.
  • Kawai Y, Nishikawa T, Shiba Y, Saito S, Murota K, Shibata N, et al. Macrophage as a target of quercetin glucuronides in human atherosclerotic arteries: implication in the anti-atherosclerotic mechanism of dietary flavonoids . J Biol Chem 2008;283:9424–9434.
  • Ford E, Hughes MN, Wardman P. Kinetics of the reactions of nitrogen dioxide with glutathione, cysteine, and uric acid at physiological pH. Free Radic Biol Med 2002;32:1314–1323.
  • Kirchner T, Flemmig J, Fortmüller PG, Obinger C, Arnhold J. (-)-Epicatechin enhances the chlorinating activity of human myeloperoxidase. Arch Biochem Biophys 2010;495:21–27.
  • Flemmig J, Remmler J, Röhring F, Arnhold J. (-)-Epicatechin regenerates the chlorinating activity of myeloperoxidase in vitro and in neutrophils granulocytes. J Inorg Biochem 2014;130:84–91.
  • Pincemail J, Deby C, Thirion A, de Bruyn-Dister M, Goutier R. Human myeloperoxidase activity is inhibited in vitro by quercetin. Comparison with three related compounds. Experientia 1988;44:450–453.
  • Shiba Y, Kinoshita T, Chuman H, Taketani Y, Takeda E, Kato Y, et al. Flavonoids as substrates and inhibitors of myeloperoxidase: molecular actions of aglycone and metabolites. Chem Res Toxicol 2008;21:1600–1609.
  • Meotti FC, Senthilmohan R, Harwood DT, Missau FC, Pizzolatti G, Kettle AJ. Myricitrin as a substrate and inhibitor of myeloperoxidase: implications for the pharmacological effects of flavonoids. Free Radic Biol Med 2008;44:109–120.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.