Differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: A structure/redox potential relationship study.
[en] We investigated the antioxidant activities of some phenolic acid derivatives on a cell free system and on cellular and enzymatic models involved in inflammation. The stoichiometric antioxidant activities of phenolic acid derivatives were studied by measuring their capacity to scavenge the radical cation 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+) and reactive oxygen species (ROS) produced by stimulated neutrophils. The anticatalytic antioxidant capacity of the molecules was evaluated on the activity of myeloperoxidase (MPO), an oxidant enzyme present in and released by the primary granules of neutrophils. The ROS produced by PMA-stimulated neutrophils were measured by lucigenin-enhanced chemiluminescence (CL) and the potential interaction of the molecules with MPO was investigated without interferences due to medium by Specific Immuno-Extraction Followed by Enzyme Detection (SIEFED). The antioxidant activities of the phenolic compounds were correlated to their redox potentials measured by differential pulse voltammetry (DPV), and discussed in relation to their molecular structure. The ability of the phenolic molecules to scavenge ABTS radicals and ROS derived from neutrophils was inversely correlated to their increased redox potential. The number of hydroxyl groups (three) and their position (catechol) were essential for their efficacy as stoichiometric antioxidants or scavengers. On MPO activity, the inhibitory capacity of the molecules was not really correlated with their redox potential. Likewise, for the inhibition of MPO activity the number of OH groups and mainly the elongation of the carboxylic group were essential, probably by facilitating the interaction with the active site or the structure of the enzyme. The redox potential measurement, combined with ABTS and CL techniques, seems to be a good technique to select stoichiometric antioxidants but not anticatalytic ones, as seen for MPO, what rather involves a direct interaction with the enzyme.
Research center :
CORD - Centre de l'Oxygène, Recherche et Développement - ULiège
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Franck, Thierry ; Université de Liège - ULiège > Département clinique des animaux de compagnie et des équidés > Anesthésiologie gén. et pathologie chirurg. des grds animaux
Mouithys-Mickalad, Ange ; Université de Liège - ULiège > Centre de l'oxygène : Recherche et développement (C.O.R.D.)
Robert, Thierry ; Université de Liège - ULiège > Département de chimie (sciences) > Département de chimie (sciences)
Ghitti, Gianangelo
Deby-Dupont, Ginette
Neven, Philippe
Serteyn, Didier ; Université de Liège - ULiège > Département clinique des animaux de compagnie et des équidés > Anesthésiologie gén. et pathologie chirurg. des grds animaux
Language :
English
Title :
Differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: A structure/redox potential relationship study.
Publication date :
2013
Journal title :
Chemico-Biological Interactions
ISSN :
0009-2797
eISSN :
1872-7786
Publisher :
Elsevier, Amsterdam, Netherlands
Volume :
206
Issue :
2
Pages :
194-203
Peer reviewed :
Peer Reviewed verified by ORBi
Commentary :
Copyright (c) 2013 Elsevier Ireland Ltd. All rights reserved.
J.F. Arteaga, M. Ruiz-Montoya, A. Palma, G. Alonso-Garrido, S. Pintado, and J.M. Rodriguez-Mellado Comparison of the simple cyclic voltammetry (CV) and DPPH assays for the determination of antioxidant capacity of active principles Molecules 17 2012 5126 5138
B.M. Babior Phagocytes and oxidative stress Am. J. Med. 109 2000 33 44 (Pubitemid 30608735)
N. Beloborodova, I. Bairamov, A. Olenin, V. Shubina, V. Teplova, and N. Fedotcheva Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils J. Biomed. Sci. 19 2012 89
H. Benbarek, G. Deby-Dupont, C. Deby, I. Caudron, M. Mathy-Hartert, M. Lamy, and D. Serteyn Experimental model for the study by chemiluminescence of the activation of isolated equine leucocytes Res. Vet. Sci. 61 1996 59 64 (Pubitemid 126504158)
R. Boly, S. Dessy, S. Kohnen, F. Kini, M. Lompo, A. Mouithys-Mickalad, I.P. Guissou, J. Dubois, G. Deby-Dupont, D. Serteyn, and T. Franck Modulatory activities of Agelanthus dodoneifolius (Loranthaceae) extracts on stimulated equine neutrophils and myeloperoxidase activity Int. J. Mol. Med. 28 2011 261 270
M. Ciz, P. Denev, M. Kratchanova, O. Vasicek, G. Ambrozova, and A. Lojek Flavonoids inhibit the respiratory burst of neutrophils in mammals Oxid. Med. Cell. Longev. 2012 2012 181295
M.J. Davies Myeloperoxidase-derived oxidation: mechanisms of biological damage and its prevention J. Clin. Biochem. Nutr. 48 2011 8 19
C. Delporte, T. Franck, C. Noyon, D. Dufour, A. Rousseau, P. Madhoun, J.M. Desmet, D. Serteyn, M. Raes, J. Nortier, M. Vanhaeverbeek, N. Moguilevsky, J. Neve, L. Vanhamme, P. Van Antwerpen, and K. Zouaoui Boudjeltia Simultaneous measurement of protein-bound 3-chlorotyrosine and homocitrulline by LC-MS/MS after hydrolysis assisted by microwave: application to the study of myeloperoxidase activity during hemodialysis Talanta 99 2012 603 609
S. Derochette, T. Franck, A. Mouithys-Mickalad, G. Deby-Dupont, P. Neven, and D. Serteyn Intra- and extracellular antioxidant capacities of the new water-soluble form of curcumin (NDS27) on stimulated neutrophils and HL-60 cells Chem. Biol. Interact. 201 2013 49 57
N.I. Fedotcheva, R.E. Kazakov, M.N. Kondrashova, and N.V. Beloborodova Toxic effects of microbial phenolic acids on the functions of mitochondria Toxicol. Lett. 180 2008 182 188
T. Franck, S. Grulke, G. Deby-Dupont, C. Deby, H. Duvivier, E. Peters, and D. Serteyn Development of an enzyme-linked immunosorbent assay for specific equine neutrophil myeloperoxidase measurement in blood J. Vet. Diagn. Invest. 17 2005 412 419 (Pubitemid 41414957)
T. Franck, S. Kohnen, K.Z. Boudjeltia, P. Van Antwerpen, A. Bosseloir, A. Niesten, O. Gach, M. Nys, G. Deby-Dupont, and D. Serteyn A new easy method for specific measurement of active myeloperoxidase in human biological fluids and tissue extracts Talanta 80 2009 723 729
T. Franck, S. Kohnen, G. de la Rebiere, G. Deby-Dupont, C. Deby, A. Niesten, and D. Serteyn Activation of equine neutrophils by phorbol myristate acetate or N-formyl-methionyl-leucyl-phenylalanine induces a different response in reactive oxygen species production and release of active myeloperoxidase Vet. Immunol. Immunopathol. 130 2009 243 250
T. Franck, S. Kohnen, G. Deby-Dupont, S. Grulke, C. Deby, and D. Serteyn A specific method for measurement of equine active myeloperoxidase in biological samples and in in vitro tests J. Vet. Diagn. Invest. 18 2006 326 334 (Pubitemid 44181970)
T. Franck, S. Kohnen, S. Grulke, P. Neven, Y. Goutman, F. Peters, B. Pirotte, G. Deby-Dupont, and D. Serteyn Inhibitory effect of curcuminoids and tetrahydrocurcuminoids on equine activated neutrophils and myeloperoxidase activity Physiol. Res. 57 2008 577 587
P.G. Furtmuller, M. Zederbauer, W. Jantschko, J. Helm, M. Bogner, C. Jakopitsch, and C. Obinger Active site structure and catalytic mechanisms of human peroxidases Arch. Biochem. Biophys. 445 2006 199 213 (Pubitemid 43082213)
D. Galato, K. Ckless, M.F. Susin, C. Giacomelli, R.M. Ribeiro-do-Valle, and A. Spinelli Antioxidant capacity of phenolic and related compounds: correlation among electrochemical, visible spectroscopy methods and structure-antioxidant activity Redox Rep. 6 2001 243 250 (Pubitemid 32962825)
J.P. Gaut, J. Byun, H.D. Tran, W.M. Lauber, J.A. Carroll, R.S. Hotchkiss, A. Belaaouaj, and J.W. Heinecke Myeloperoxidase produces nitrating oxidants in vivo J. Clin. Invest. 109 2002 1311 1319 (Pubitemid 34546895)
R. Goldman, G.H. Claycamp, M.A. Sweetland, A.V. Sedlov, V.A. Tyurin, E.R. Kisin, Y.Y. Tyurina, V.B. Ritov, S.L. Wenger, S.G. Grant, and V.E. Kagan Myeloperoxidase-catalyzed redox-cycling of phenol promotes lipid peroxidation and thiol oxidation in HL-60 cells Free Radic. Biol. Med. 27 1999 1050 1063 (Pubitemid 29508794)
J.A. Gomez-Ruiz, D.S. Leake, and J.M. Ames In vitro antioxidant activity of coffee compounds and their metabolites J. Agric. Food Chem. 55 2007 6962 6969 (Pubitemid 47338933)
R. Gonzalez, I. Ballester, R. Lopez-Posadas, M.D. Suarez, A. Zarzuelo, O. Martinez-Augustin, and F. Sanchez de Medina Effects of flavonoids and other polyphenols on inflammation Crit. Rev. Food Sci. Nutr. 51 2011 331 362
K. Herrmann Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods Crit. Rev. Food Sci. Nutr. 28 1989 315 347
J.A. Kim, G.P. Neupane, E.S. Lee, B.S. Jeong, B.C. Park, and P. Thapa NADPH oxidase inhibitors: a patent review Expert Opin. Ther. Pat. 21 2011 1147 1158
T. Kirchner, J. Flemmig, P.G. Furtmuller, C. Obinger, and J. Arnhold (-)-Epicatechin enhances the chlorinating activity of human myeloperoxidase Arch. Biochem. Biophys. 495 2010 21 27
S.J. Klebanoff Myeloperoxidase: friend and foe J. Leukoc. Biol. 77 2005 598 625 (Pubitemid 40628741)
S. Kohnen, T. Franck, P. Van Antwerpen, K.Z. Boudjeltia, A. Mouithys-Mickalad, C. Deby, N. Moguilevsky, G. Deby-Dupont, M. Lamy, and D. Serteyn Resveratrol inhibits the activity of equine neutrophil myeloperoxidase by a direct interaction with the enzyme J. Agric. Food Chem. 55 2007 8080 8087
B.H. Kroes, A.J. van den Berg, H.C. Quarles van Ufford, H. van Dijk, and R.P. Labadie Anti-inflammatory activity of gallic acid Planta Med. 58 1992 499 504 (Pubitemid 23074535)
Y.T. Lee, M.J. Don, C.H. Liao, H.W. Chiou, C.F. Chen, and L.K. Ho Effects of phenolic acid esters and amides on stimulus-induced reactive oxygen species production in human neutrophils Clin. Chim. Acta 352 2005 135 141
Y. Li, H. Zhu, P. Kuppusamy, V. Roubaud, J.L. Zweier, and M.A. Trush Validation of lucigenin (bis-N-methylacridinium) as a chemilumigenic probe for detecting superoxide anion radical production by enzymatic and cellular systems J. Biol. Chem. 273 1998 2015 2023 (Pubitemid 28069247)
E. Malle, P.G. Furtmuller, W. Sattler, and C. Obinger Myeloperoxidase: a target for new drug development? Br. J. Pharmacol. 152 2007 838 854 (Pubitemid 350100486)
D.K. Maurya, and T.P. Devasagayam Antioxidant and prooxidant nature of hydroxycinnamic acid derivatives ferulic and caffeic acids Food Chem. Toxicol. 48 2010 3369 3373
F.C. Meotti, R. Senthilmohan, D.T. Harwood, F.C. Missau, M.G. Pizzolatti, and A.J. Kettle Myricitrin as a substrate and inhibitor of myeloperoxidase: implications for the pharmacological effects of flavonoids Free Radical Biol. Med. 44 2008 109 120 (Pubitemid 350138636)
M. Mochizuki, S. Yamazaki, K. Kano, and T. Ikeda Kinetic analysis and mechanistic aspects of autoxidation of catechins Biochim. Biophys. Acta 15 2002 1 3
M. Nardini, E. Cirillo, F. Natella, and C. Scaccini Absorption of phenolic acids in humans after coffee consumption J. Agric. Food Chem. 50 2002 5735 5741
F. Natella, M. Nardini, M. Di Felice, and C. Scaccini Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation J. Agric. Food Chem. 47 1999 1453 1459 (Pubitemid 29217138)
Y.Y. Ow, and I. Stupans Gallic acid and gallic acid derivatives: effects on drug metabolizing enzymes Curr. Drug Metab. 4 2003 241 248 (Pubitemid 36656481)
A.M. Pisoschi, and G.P. Negulescu Methods for total antioxidant activity determination: a review Biochem. Anal. Biochem. 1 2011 106
D. Prochazkova, I. Bousova, and N. Wilhelmova Antioxidant and prooxidant properties of flavonoids Fitoterapia 82 2011 513 523
J.F. Pycock, W.E. Allen, and T.H. Morris Rapid, single-step isolation of equine neutrophils on a discontinuous percoll density gradient Res. Vet. Sci. 42 1987 411 412
R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans Antioxidant activity applying an improved ABTS radical cation decolorization assay Free Radical Biol. Med. 26 1999 1231 1237 (Pubitemid 29262709)
C.A. Rice-Evans, N.J. Miller, and G. Paganga Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biol. Med. 20 1996 933 956 (Pubitemid 26157509)
R.J. Robbins Phenolic acids in foods: an overview of analytical methodology J. Agric. Food Chem. 51 2003 2866 2887
Y. Shiba, T. Kinoshita, H. Chuman, Y. Taketani, E. Takeda, Y. Kato, M. Naito, K. Kawabata, A. Ishisaka, J. Terao, and Y. Kawai Flavonoids as substrates and inhibitors of myeloperoxidase: molecular actions of aglycone and metabolites Chem. Res. Toxicol. 21 2008 1600 1609
A. Simic, D. Manojlovic, D. Segan, and M. Todorovic Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics Molecules 12 2007 2327 2340
W.R. Sousa, C. da Rocha, C.L. Cardoso, D.H.S. Silva, and M.V.B. Zanoni Determination of the relative contribution of phenolic antioxidants in orange juice by voltammetric methods J. Food Compos. Anal. 17 2004 619 633 (Pubitemid 38979527)
Y. Surh Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances Mutat. Res. 428 1999 305 327 (Pubitemid 29389702)
C.N. Tsumbu, G. Deby-Dupont, M. Tits, L. Angenot, M. Frederich, S. Kohnen, A. Mouithys-Mickalad, D. Serteyn, and T. Franck Polyphenol content and modulatory activities of some tropical dietary plant extracts on the oxidant activities of neutrophils and myeloperoxidase Int. J. Mol. Sci. 13 2012 628 650
B.S. van der Veen, M.P. de Winther, and P. Heeringa Myeloperoxidase: molecular mechanisms of action and their relevance to human health and disease Antioxid. Redox Signal. 11 2009 2899 2937
D. Villaño, M.S. Fernández-Pachón, A.M. Troncoso, and M.C. García-Parrilla Comparison of antioxidant activity of wine phenolic compounds and metabolites in vitro Anal. Chim. Acta 538 2005 391 398 (Pubitemid 40591903)
K.L. Wolfe, and R.H. Liu Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements J. Agric. Food Chem. 55 2007 8896 8907 (Pubitemid 350105534)
K.E. Yakovleva, S.A. Kurzeev, E.V. Stepanova, T.V. Fedorova, B.A. Kuznetsov, and O.V. Koroleva Characterization of plant phenolic compounds by cyclic voltammetry Appl. Biochem. Microbiol. 43 2007 661 668 (Pubitemid 350105362)
