Flavonoid electrochemistry: A review on the electroanalytical applications

Revista Brasileira de Farmacognosia

Volumn 23, Issue 3, 2013, Pages 542-558

  Gil, Eric S ^a   Couto, Renê O ^b  

^a FEDERAL UNIVERSITY OF GOIÁS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Antioxidant activity; Phytopharmaceuticals; Quality control; Redox behavior; Structure activity relationship; Voltammetry

Indexed keywords

APIGENIN; AURANTIIN; CATECHIN; CYANIDIN 3 GLUCOSIDE; DIOSMETIN; DIOSMIN; EPICATECHIN; EPICATECHIN GALLATE; EPIGALLOCATECHIN GALLATE; ERIODICTYOL; FISETIN; FLAVONOID; GALANGIN; HESPERETIN; HESPERIDIN; HYDROQUINONE; ISORHAMNETIN; LINARIN; LUTEOLIN; MALVIN; MORIN; MYRICETIN; NARINGENIN; ORIENTIN; QUERCETIN; RESORCINOL DERIVATIVE; RHAMNETIN; RUTOSIDE; TAXIFOLIN; UNINDEXED DRUG;

ANTIOXIDANT ACTIVITY; ELECTROCHEMICAL ANALYSIS; ELECTROCHEMISTRY; HUMAN; MOLECULAR ELECTRONICS; NONHUMAN; OXIDATION REDUCTION POTENTIAL; QUALITY CONTROL; REVIEW; STEREOCHEMISTRY;

EID: 84879059600     PISSN: 0102695X     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0102-695X2013005000031     Document Type: Article

References (102)

1. Aaby K, Hvattum E, Skrede G 2004. Analysis of favonoids and other phenolic compounds using High-Performance Liquid Chromatography with coulometric array detection: relationship to antioxidant activity. J Agric Food Chem 52: 4595-4603.
2. Abdel-Hamid R, Newair EF 2011. Electrochemical behaviour of antioxidants: I. Mechanistic study on electrochemical oxidation of gallic acid in aqueous solutions at glassy carbon electrode. J Electroanal Chem 657: 107-112.
3. Adam V, Mikelova R, Hubalek J, Hanustiak P, Beklova M, Hodek P, Horna A, Trnkova L, Stiborova M, Zeman L, Kizek R 2007. Utilizing of square wave voltammetry to detect favonoids in the presence of human urine. Sensors 7: 2402-2418.
4. Aguilar-Sanchez R, Ahuatl-Garcia F, Davila-Jimenez MM, Elizalde-Gonzalez MP, Guevara-Villa MRG 2005. Chromatographic and electrochemical determination of quercetin and kaempferol in phytopharmaceuticals. J Pharmaceut Biomed 38: 239-249.
5. Amic D, Davidovic-Amic D, Beslo D, Trinajstic N 2003. Structure-radical scavenging activity relationships of favonoids. Croatica Chim Acta 76: 55-61.
6. Arslan G, Yazici B, Erbil M 2005. The effect of pH, temperature and concentration on electrooxidation of phenol. J Hazard Mater B124: 37-43.
7. Bara MTF, Serrano SHP, Asquieri ER, Lúcio TC, Gil ES 2008. Medida del potencial anódico en estado sólido: Una herramienta para la determinación del potencial antioxidante de ftoterápicos. Lat Am J Pharm 27: 89-92.
8. Behzad R, Najmeh M, Ali AE, Hassan KM 2011. Molecularly imprinted-multiwall carbon nanotube paste electrode as a biosensor for voltammetric detection of rutin. Anal Method 3: 2510-2516.
9. Blasco AJ, Gonzalez MC, Escarpa A 2004. Electrochemical approach for discriminating and measuring predominant favonoids and phenolic acids using differential pulse voltammetry: towards an electrochemical index of natural antioxidants. Anal Chim Acta 511: 71-81.
10. Brondani D, Vieira IC, Piovezan C, Silva JMR, Neves A, Dupont J, Scheeren CW 2010. Sensor for fsetin based on gold nanoparticles in ionic liquid and binuclear nickel complex immobilized in silica. Analyst 135: 1015-1022.
11. Cao G, Sofc E, Prior RL 1997. Antioxidant and prooxidant behavior of favonoids: structure-activity relationships. Free Rad Bio Med. 22: 749-760.
12. Chaves DS, Frattani FS, Assafm M, de Almeida AP, de Zingali RB, Costa SS 2011. Phenolic chemical composition of Petroselinum crispum extract and its effect on haemostasis. Nat Prod Commun 6: 961-964.
13. Chen X, Wang Z, Zhang F, Zhu L, Li Y, Xia Y 2010. Determination of rutin on the poly(p-aminobenzene sulfonic acid) modified glassy carbon electrode. Chem Pharm Bull 58: 475-478.
14. Cook NC, Samman S 1996. Flavonoids-chemistry, metabolism, cardioprotective effects, and dietary sources. J Nutr Biochem 7: 66-76.
15. Diculescu V, Santana HE, Gil ES, Oliveira-Brett AM 2012. Methoxylation and glycosylation effect on the redox mechanism of citrofavones. Electroanal 24: 1019-1026.
16. Dongming Z, Xiuhua Z, Lijun F, Qi Q, Wang S 2011. Sensitive electrochemical determination of luteolin in peanut hulls using multi-walled carbon nanotubes modifed electrode. Food Chem 127: 694-698.
17. Dueñas M, González-Manzano S, González-Paramás A, Santos-Buelga C 2010. Antioxidant evaluation of O-methylated metabolites of catechin, epicatechin and quercetin. J Pharmaceut Biomed 51: 443-449.
18. El-Shahaw MS 2006. Determination of trace levels of diosmin in a pharmaceutical preparation by adsorptive stripping voltammetry at a glassy carbon electrode. Anal Sci 22: 1351-1354.
19. Enache TA, Oliveira-Brett AM 2011. Phenol and para-substituted phenols electrochemical oxidation pathways. J Electroanal Chem 655: 9-16.
20. Erlund I 2004. Review of the favonoids quercetin, hesperetin and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology. Nutr Res 24: 851-874.
21. Escarpa A, González MC, Blasco AJ, Rogerio MC, Hervás M 2007. Evaluation of accuracy of electrochemical isofavonoid index for the determination of total isofavones in soy samples. Electroanal 19: 952-957.
22. Fernandes IPG, Oliveira SCB, Ghalkhani M, Shahrokhian S, Oliveira-Brett AM 2010. Antioxidants daidzein and 7-hydroxy-4-chromone electrochemical oxidation mechanisms. Anal Chim Acta 22: 1-9.
23. Ferreira M, Varela H, Torresi RM, Tremiliosi-Filho G 2006. Electrode passivation caused by polymerization of different phenolic compounds. Electrochim Acta 52: 434-442.
24. Fogliatto DK, Barbosa AMJ, Ferreira VS 2010. Voltammetric determination of the phytoestrogen genistein in soy fours and soy based supplements using cationic surfactant cetyltrimetylammonium bromide. Colloid Surf B: Biointerfaces 78: 243-249.
25. Franzoi AC, Peralta RA, Neves A, Vieira IC 2009. Biomimetic sensor based on Mn(III)Mn(II) complex as manganese peroxidase mimetic for determination of rutin. Talanta 78(1): 221-226.
26. Freitas KHG, Medeiros RA, Fatibello-Filho O 2009. Voltammetric determination of rutin using a carbon composite electrode modifed with Copper(II)-resin. Anal Lett 42: 881-897.
27. Ghica ME, Oliveira-Brett AM 2005. Electrochemical oxidation of rutin. Electroanalysis 17: 313-318.
28. Gil ES, Enache AT, Oliveira-Brett AM 2012. Anodic behaviour of favonoids orientin, eriodictyol and robinin at a glassy carbon electrode. Electroanal 24: 1576-1583.
29. Gomez-Pineda LE, Oropeza-Guzman MT, Pina-Luis GE 2009. Identifcation of favonoid oxidation potentials as a function of pH. ECS Transactions 20: 141-149.
30. Han RM, Tian YX, Liu Y, Chen CH, Ai XC, Zhang JP, Skibsted LH 2009. Comparison of favonoids and isofavonoids as antioxidants. J Agric Food Chem 57: 3780-3785.
31. Harborne JB, Williams CA 2000. Advances in favonoid research since 1992. Phytochemistry 55: 481-504.
32. He JB, Yuan SJ, Du JQ, Hu XR, Wang Y 2009. Voltammetric and spectral characterization of two favonols for assay-dependent antioxidant capacity. Bioelectrochem 75: 110-116.
33. Hendrickson HP, Kaufman AD, Lunte CE 1994. Electrochemistry of catechol-containing favonoids. J Pharmaceut Biomed 12: 325-334.
34. Hidalgo M, Sánches-Moreno C, Pascual-Teresa S 2010. Flavonoid-favonoid interaction and its effect on their antioxidante activity. Food Chem 121: 691-696.
35. Huang T, Gao P, Hageman MJ 2004. Rapid screening of antioxidants in pharmaceutical formulation development using cyclic voltammetry - potential and limitations. Curr Drug Disc Tech 1: 173-179.
36. Janeiro P, Oliveira-Brett AM 2005. Solid state electrochemical oxidation mechanism of morin in aqueous media. Electroanal 17: 733-738.
37. Janeiro P, Corduneanu O, Oliveira-Brett AM 2005. Chrysin and (±)taxifolin electrochemical oxidation mechanisms. Electroanal 17: 1059-1064.
38. Janeiro P, Oliveira-Brett AM 2007. Redox Behavior of Anthocyanins present in Vitis vinifera L. Electroanal 19: 1779-1786.
39. Jorgensen LV, Cornett C, Justesen U, Skibsted LH, Dragsted LO 1998. Two-electron electrochemical oxidation of quercetin and kaempferol changes only the favonoid C-ring. Free Rad Res 29: 339-350.
40. Jorgensen LV, Madsen HL, Thomsen MK, Dragsted LO, Skibsted LH 1999. Regeneration of phenolic antioxidants from phenoxyl radicals: an ESR and electrochemical study of antioxidant hierarchy. Free Rad Res 30: 207-220.
41. Jovanovic SV, Steenken S, Hara Y, Simic MG 1996. Reduction potentials of favonoid and model phenoxyl radicals. Which ring in favonoids is responsible for antioxidant activity? J Chem Soc Perk T 2 11: 2497-2504.
42. Kilinc E 2009. Signifcance of chromatographic and voltammetric data for the classifcation of green teas in Türkiye: a principle component analysis approach. J Liq Chromatogr R T 32: 221-241.
43. Kilmartin PA, Zou H, Waterhouse AL 2002. Correlation of wine phenolic composition versus cyclic voltammetry response. Am J Enol Viticult 53: 294-302.
44. Korbut O, Buková M, Labuda J, Gründler P 2003. Voltammetric detection of antioxidative properties of favonoids using electrically heated DNA modifed carbon paste electrode. Sensors 3: 1-10.
45. Labuda J, Buková M, Heilerová L, Šilhár S, Štepánek I 2003. Evaluation of the redox properties and anti/pro-oxidant effects of selected favonoids by means of a DNA-based electrochemical biosensor. Anal Bioanal Chem 376: 168-173.
46. Liang J, Tian YX, Fu LM, Wang TH, Li HJ, Wang P, Han RM, Zhang JP, Skibsted LH 2008. Daidzein as an antioxidant of lipid: effects of microenvironment in relation to chemical structure. J Agric Food Chem 56: 10376-10383.
47. Lima AA, Sussuchi EM, de Giovani WF 2007. Electrochemical and antioxidant properties of anthocyanins and anthocyanidins. Croatica Chem Acta 80: 29-34.
48. Liu AL, Zhang SB, Chen W, Huang LY, Lin XH, Xia XH 2008a. Study of the electrochemical behavior of isorhamnetin on a glassy carbon electrode and its application. Talanta 77: 314-318.
49. Liu A, Zhang S, Huang L, Cao Y, Yao H, Chen W, Lin X 2008b. Electrochemical oxidation of luteolin at a glassy carbon electrode and its application in pharmaceutical analysis. Chem Pharm Bull 56: 745-747.
50. Macikova, P; Halouzka, V; Hrbac, J; Bartak, P; Skopalova J 2012. Electrochemical Behavior and Determination of Rutin on Modifed Carbon Paste Electrodes. Scientifc World Journal. 2012, Article ID 394756, 9 pages.
51. Markovic ZS, Mentus S V, Dimitric MJM 2009. Electrochemical and density functional theory study on the reactivity of fsetin and its radicals: implications on in vitro antioxidant activity. J Phy Chem A 113: 14170-14179.
52. Martinez S, Valek L, Petrovic Z, Metikos-Hukovic M, Piljac J 2005. Catechin antioxidant action at various pH studied by cyclic voltammetry and PM3 semi-empirical calculations. J Electroanal Chem 584: 92-99.
53. Masek A, Zaborski M, Chrzescijanska E 2011. Electrooxidation of favonoids at platinum electrode studied by cyclic voltammetry. Food Chem 127: 699-704.
54. Medvidovic-Kosanovic M, Šeruga M, Jakobek L, Novak I 2010. Electrochemical and antioxidant properties of (+)-catechin, quercetin and rutin. Croatica Chem Acta 83: 197-207.
55. Mishra K, Ojha H, Chaudhury NK 2012. Estimation of antiradical properties of antioxidants using DPPH Assay. A critical review and results. Food Chem 130: 1036-1043.
56. Montoro P, Braca A, Pizza C, De Tommasi N 2005. Structure-antioxidant activity relationships of favonoids isolated from different plant species. Food Chem 92: 349-355.
57. Moreno M, Arribas AS, Bermejo E, Zapardiel A, Chicharro M 2011.Analysis of polyphenols in wine by CZE with amperometric detection using carbon nanotube-modified electrodes. Electrophoresis 32: 877-883.
58. Mülazimoǧlu IE, Özkan E, Solak AO 2011. Covalently grafted on to the glassy carbon electrode in non-aqueous media of apigenin and naringenin as different favonoid derivatives. Anal Bioanal Electrochem 3: 102-118.
59. Mülazimoǧlu IE, Özkan E, Solak AO 2012. High energetic body source and strong antioxidant quercetin, morin and rutin: Their covalent grafting onto the glassy carbon electrode surfaces and investigation of surface properties. Energy Educ Sci Tech A 28: 957-968.
60. Narayana KR, Reddy MS, Chaluvadi MR, Krishna DR 2001. Biofavonoids classifcation, pharmacological, biochemical effects and therapeutic potential. Indian J Pharmacol 33: 2-16.
61. Nasr B, Abdellatif G, Cañizares P, Sáez C, Lobato J, Rodrigo MA 2005. Electrochemical oxidation of hydroquinone, resorcinol, and catechol on boron-doped diamond anodes. Environ Sci Technol 39: 7234-7239.
62. Nijveldt RJ, Van Nood E, Van Hoorn DEC, Boelens PG, Van Norren K, Van Leeuwen PAM 2001. Flavonoids: a review of probable mechanisms of action and potential applications. Am J Clin Nutr 74: 418-425.
63. Novak I, Janeiro P, Seruga M, Oliveira-Brett AM 2008. Ultrasound extracted favonoids from four varieties of Portuguese red grape skins determined by reverse-phase high-performance liquid chromatography with electrochemical detection. Anal Chim Acta 630(2): 107-115.
64. Novak I, Seruga M, Komorsky-Lovric S 2009a. Square-wave and cyclic voltammetry of epicatechin gallate on glassy carbon electrode. J Electroanal Chem 631: 71-75.
65. Novak I, Seruga M, Komorsky-Lovric S 2009b. Electrochemical characterization of epigallocatechin gallate using square-wave voltammetry. Electroanal 21: 1019-1025.
66. Oliveira AC, Mascaro LH 2011. Characterization of carbon nanotubes paste electrode and its application as rutin sensor. Curr Anal Chem 7: 101-109.
67. Oliveira-Brett AM, Ghica ME 2003. Electrochemical oxidation of quercetin. Electroanal 15: 1745-1750.
68. Pannala AS, Chan TS, ÓBrien PJ, Rice-Evans CA 2001. Flavonoid B-ring chemistry and antioxidant activity: fast reaction kinetics. Biochem Bioph Res Co 282: 1161-1168.
69. Peyrat-Maillard MN, Bonnely S, Berset C 2000. Determination of the antioxidant activity of phenolic compounds by coulometric detection. Talanta 51: 709-716.
70. Rapta P, Misik V, Stasko A, Vrabel I 1995. Redox intermediates of favonoids and caffeic acid esters from propolis: an EPR spectroscopy and cyclic voltammetry study. Free Rad Bio Med 18: 901-908.
71. Reichart E, Obendorf D 1998. Determination of naringin in grapefruit juice by cathodic stripping differential pulse voltammetry at the hanging mercury drop electrode. Anal Chim Acta 360: 179-187.
72. Reis NS, Serrano SHP, Meneghatti R, Gil ES 2009. Métodos eletroquímicos usados para avaliação da atividade antioxidante de produtos naturais. Lat Am J Pharm 28: 949-53.
73. Rene A, Abasq ML, Hauchard D, Hapiot P 2010. How do phenolic compounds react toward superoxide ion? A simple electrochemical method for evaluating antioxidant capacity. Anal Chem 82: 8703-8710.
74. Rice-Evans CA, Miller NJ, Paganga G 1996. Structure-antioxidant activity relationships of favonoids and phenolic acids. Free Rad Bio Med, 20: 933-956.
75. Romani A, Minunni M, Mulinacci N, Pinelli P, Vincieri FF, Del Carlo M, Mascini M 2000. Comparison among differential pulse voltammetry, amperometric biosensor, and HPLC/DAD analysis for polyphenol determination. J Agric Food Chem 48: 1197-1203.
76. Santos CMM, Garcia MBQ, Silva AMS, Santus R, Morlière P, Fernandes E 2013. Electrochemical characterization of bioactives hydroxyxanthones by cyclic voltammetry. Tetrahedron Lett 54: 85-90.
77. Slabbert NP 1977. Ionization of some favonols and dihydrofavonoids. Tetrahedron 33: 821-824.
78. Simic A, Manojlovi D, Šegan D, Todorovi M 2007. Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics. Molecules 12: 2327-2340.
79. Sims MJ, Li Q, Kachoosangi RT, Wildgoose GG, Compton RG 2009. Using multiwalled carbon nanotube modifed electrodes for the adsorptive striping voltammetric determination of hesperidin. Electrochim Acta 54: 5030-5034.
80. Sokolova R, Degano I, Ramesova S, Bulickova J, Hromadova M, Gal M, Fiedler J, Valášek M 2008. The oxidation mechanism of the antioxidant quercetin in nonaqueous media. Electrochim Acta 56: 7421-7427.
81. Taylor LP, Grotewold E 2005. Flavonoids as developmental regulators. Curr Opin Plant Biol 8: 317-323.
82. Temerk YM, Ibrahim MS, Kotb M 2011. Square-wave cathodic adsorptive stripping voltammetric determination of 3-hydroxyfavone, morin and hesperidin in bulk form and biological fuids in absence and presence of Cu(II). J Braz Chem Soc 22: 2056-2064.
83. Tsao R 2010. Chemistry and biochemistry of dietary polyphenols. Nutrients 2: 1231-1246.
84. Tsimogiannis DI, Oreopoulou V 2004. Free radical scavenging and antioxidant activity of 5,7,3́4́-hydroxy-substituted favonoids. Innov Food Sci Emerg 5: 523-528.
85. Tyszczuk K 2009. Sensitive voltammetric determination of rutin at an in situ plated lead flm electrode. J Pharmaceut Biomed 49: 558-561.
86. Vestergaard M, Kerman K, Tamiya E 2005. An electrochemical approach for detecting copper-chelating properties of favonoids using disposable pencil graphite electrodes: possible implications in copper-mediated illnesses. Anal Chim Acta 538: 273-281.
87. Volikakis GJ, Efstathiou CE 2000. Determination of rutin and other favonoids by fow-injection/adsorptive stripping voltammetry using nujol-graphite and diphenylether-graphite paste electrodes. Talanta 51: 775-785.
88. Volikakis GJ, Efstathiou CE 2005. Fast screening of total favonols in wines, tea-infusions and tomato juice by fow injection/adsorptive stripping voltammetry. Anal Chim Acta 551: 124-131.
89. Xiao P, Zhou Q, Xiao F, Zhao F, Zeng B 2006. Sensitive voltammetric determination of morin on a multi-walled carbon nanotubes-paraffn oil paste electrode. Int J Electrochem Sci 1: 228-237.
90. Xing TL, Wang F, Mao YY, Wang LP, Ye BX 2009. Electrochemical behavior of apigenin at a glassy carbon electrode and its analytical application. J Chin Chem Soc 56: 303-309.
91. Wang Y, Xiong H, Zhang X, Wang S 2010. Detection of rutin at DNA modified carbon paste electrode based on a mixture of ionic liquid and paraffin oil as a binder. Microchim Acta 170: 27-32.
92. Wu L, Laughlin-Jr JB, Dewald HD 1997. Voltammetry and LCEC of isofavones. Electroanal 9: 796-799.
93. Wu DM, Liu S, Gao HF, Li JL, Liu HY, Liang QC 2007. Investigation on the Electrochemical and Spectra Properties of Myricetin. J Electrochem 13: 29-34.
94. Wu SH, Sun JJ, Zhang DF, Lin ZB, Nie FH, Qiu HY, Chen GN 2008. Nanomolar detection of rutin based on adsorptive stripping analysis at single-sided heated graphite cylindrical electrodes with direct current heating. Electrochim Acta 53: 6596-6601.
95. Yakovleva KE, Kurzeev SA, Stepanova EV, Federova TV, Kuznetsov BA, Koroleva OV 2007. Characterization of plant phenolic compounds by cyclic voltammetry. Appl Biochem Micro+ 43: 661-668.
96. Yamamura S 2003. Oxidation of phenols. In: Rappoport Z, The chemistry of phenols, John Wiley & Sons Ltd, Chichester, p. 1154-1156.
97. Yang B, Kotani A, Arai K, Kusu F 2001. Estimation of the antioxidant activities of favonoids from their oxidation potentials. Anal Sci 17: 599-604.
98. Yang S, Qu L, Li G, Liu C 2010. Gold nanoparticles/ ethylenediamine/carbon nanotube modifed glassy carbon electrode as the voltammetric sensor for selective determination of rutin in the presence of ascorbic acid. J Electroanal Chem 645: 115-122.
99. Zhang D, Chu L, Liu Y, Wang A, Ji B, Wu W, Zhou F, Wei Y, Cheng Q, Cai S, Xie L, Jia G 2011. Analysis of the antioxidant activity capacities of favonoids under different spectrophotometric assays using cyclic voltammetry and density functional theory. J Agr Food Chem 59: 10277-10285.
100. Zielinska D, Zielinski H 2010. Antioxidant activity of favone C-glucosides determined by updated analytical strategies. Food Chem 124: 672-678.
101. Ziyatdinova G, Aytuganova I, Nizamova A, Morozov M, Budnikov H 2011. Cyclic voltammetry of natural favonoids on MWNT-modifed electrode and their determination in pharmaceuticals. Collect Czech Chem C 76: 1619-1631.
102. Zoulis NE, Efstathiou CE 1996. Preconcentration at a carbon-paste electrode and determination by adsorptive-stripping voltammetry of rutin and other favonoids. Anal Chim Acta 320: 255-261.