About biological affecting of flavonoids on animal organisms is known less,thus we selected flavonoids, flavanones and flavones, and their glycosides, which wereexamined as potential inducers of cytochrome(s) P450 when administrated by gavages intoexperimental male rats. The study was focused on induction of CYP1A1, the majorcytochrome P450 involved in carcinogen activation. The data obtained demonstrate thenecessity of taking into account not only ability of flavonoids to bind to Ah receptor(induction factor) but also to concentrate on their distribution and metabolism (includingcolon microflora) in the body. After that we examined certain flavonoids as potential inducers of cytochrome P450, we wanted to suggest and optimize suitable electrochemical technique for determination of selected flavonoids (quercetin, quercitrin, rutin, chrysin and diosmin) in body liquids. For these purposes, we selected square wave voltannetry using carbon paste electrode. Primarily we aimed on investigation of their basic electrochemical behaviour. After that we have optimized frequency, step potential and supporting electrolyte. Based on the results obtained, we selected the most suitable conditions for determination of the flavonoids as follows: frequency 180 Hz, step potential 1.95 mV/s and phosphate buffer of pH 7 as supporting electrolyte. Detection limits (3 S/N) of the flavonoids were from units to tens of nM except diosmin, where the limit were higher than μM. In addition, we attempted to suggest a sensor for analysis of flavonoids in urine. It clearly follows from the results obtained that flavonoids can be analysed in the presence of animal urine, because urine did not influence much the signals of flavonoids (recoveries of the signals were about 90 %).

Department of Animal Nutrition and Forage Production Faculty of Agronomy Mendel University of Agriculture and Forestry Zemedelska 1 CZ 613 00 Brno Czech Republic

Department of Biochemistry Faculty of Science Charles University Albertov 2030 CZ 128 40 Prague Czech Republic

Department of Chemistry and Biochemistry Mendel University of Agriculture and Forestry Zemedelska 1 CZ 613 00 Brno Czech Republic

Department of Chemistry Faculty of Science Masaryk University Kotlarska 37 CZ 611 37 Brno Czech Republic

Department of Food Engineering Faculty of Technology Tomas Bata University CZ 762 72 Zlin Czech Republic

Department of Microelectronics Faculty of Electrical Engineering and Communication Brno University of Technology Udolni 53 CZ 602 00 Brno Czech Republic

Department of Veterinary Ecology and Environmental Protection Faculty of Veterinary Hygiene and Ecology University of Veterinary and Pharmaceutical Sciences Palackeho 1 3 CZ 612 42 Brno Czech Republic

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Taylor L.P., Grotewold E. Flavonoids as developmental regulators. Curr. Opin. Plant Biol. 2005;8:317–323. PubMed

Woo H.H., Jeong B.R., Hawes M.C. Flavonoids: from cell cycle regulation to biotechnology. Biotechnol. Lett. 2005;27:365–374. PubMed

Williams C.A., Grayer R.J. Anthocyanins and other flavonoids. Nat. Prod. Rep. 2004;21:539–573. PubMed

Di Carlo G., Mascolo N., Izzo A.A., Capasso F. Flavonoids: Old and new aspects of a class of natural therapeutic drugs. Life Sci. 1999;65:337–353. PubMed

Klejdus B., Sterbova D., Stratil P., Kuban V. Identification and characterization of isoflavones in plant material by HPLC-DAD-MS tandem. Chem. Listy. 2003;97:530–539.

Zand R.S.R., Jenkins D.J.A., Diamandis E.P. Flavonoids and steroid hormone-dependent cancers. J. Chrom. B. 2002;777:219–232. PubMed

Yao L.H., Jiang Y.M., Shi J., Tomas-Barberan F.A., Datta N., Singanusong R., Chen S.S. Flavonoids in food and their health benefits. Plant Foods for Human Nutrition. 2004;59:113–122. PubMed

Ren W.Y., Qiao Z.H., Wang H.W., Zhu L., Zhang L. Flavonoids: Promising anticancer agents. Med. Res. Rev. 2003;23:519–534. PubMed

Sukardiman, Darwanto A., Tanjung M., Darmadi M.O. Cytotoxic mechanism of flavonoid from Temu Kunci (Kaempferia pandurata) in cell culture of human mammary carcinoma. Clin. Hemorheol. Microcirc. 2000;23:185–190. PubMed

Constantinou A., Mehta R., Runyan C., Rao K., Vaughan A., Moon R. Flavonoids as DNA Topoisomerase Antagonists and Poisons - Structure-Activity-Relationships. J. Nat. Prod. 1995;58:217–225. PubMed

Primiano T., Yu R., Kong A.N.T. Signal transduction events elicited by natural products that function as cancer chemopreventive agents. Pharm. Biol. 2001;39:83–107.

Kohn M.C., Walker N.J., Kim A.H., Portier C.J. Physiological modeling of a proposed mechanism of enzyme induction by TCDD. Toxicology. 2001;162:193–208. PubMed

Omiecinski C.J., Remmel R.P., Hosagrahara V.P. Concise review of the cytochrome P450s and their roles in toxicology. Toxicol. Sci. 1999;48:151–156. PubMed

Hodek P., Trefil P., Stiborova M. Flavonoids-potent and versatile biologically active compounds interacting with cytochromes P450. Chem.-Biol. Interact. 2002;139:1–21. PubMed

Naczk M., Shahidi F. Extraction and analysis of phenolics in food. J. Chromatogr. A. 2004;1054:95–111. PubMed

Jac P., Polasek M., Pospisilova M. Recent trends in the determination of polyphenols by electromigration methods. J. Pharm. Biomed. Anal. 2006;40:805–814. PubMed

Bedgood D.R., Bishop A.G., Prenzler P.D., Robards K. Analytical approaches to the determination of simple biophenols in forest trees such as Acer (maple), Betula (birch), Coniferus, Eucalyptus, Juniperus (cedar), Picea (spruce) and Quercus (oak) Analyst. 2005;130:809–823. PubMed

Smyth W.F., Brooks P. A critical evaluation of high performance liquid chromatography-electrospray ionisation-mass pectrometry and capillary electrophoresis-electrospray-mass spectrometry for the detection and determination of small molecules of significance in clinical and forensic science. Electrophoresis. 2004;10-11:1413–1446. PubMed

Robards K. Strategies for the determination of bioactive phenols in plants, fruit and vegetables. J. Chrom. A. 2003;1-2:657–691. PubMed

Suntornsuk L. Capillary electrophoresis of phytochemical substances. J. Pharmaceut. Biomed. 2002;5:679–698. PubMed

Franke A.A., Custer L.J., Arakaki C., Murphy S.P. Vitamin C and flavonoid levels of fruits and vegetables consumed in Hawaii. J. Food Compos. Anal. 2004;1:1–35.

Escarpa A., Gonzales M.C. An overview of analytical chemistry of phenolic compounds in foods. Crit. Rev. Anal. Chem. 2001;2:57–139.

Kizek R., Trnkova L., Palecek E. Determination of metallothionein at the femtomole level by constant current stripping chronopotentiometry. Anal. Chem. 2001;73:4801–4807. PubMed

Petrlova J., Potesil D., Mikelova R., Blastik O., Adam V., Trnkova L., Jelen F., Prusa R., Kukacka J., Kizek R. Attomole voltammetric determination of metallothionein. Electrochim. Acta. 2006;51:5112–5119.

Palecek E., Masarik M., Kizek R., Kuhlmeier D., Hassmann J., Schulein J. Sensitive electrochemical determination of unlabeled MutS protein and detection of point mutations in DNA. Anal. Chem. 2004;76:5930–5936. PubMed

Masarik M., Kizek R., Kramer K.J., Billova S., Brazdova M., Vacek J., Bailey M., Jelen F., Howard J.A. Application of avidin-biotin technology and adsorptive transfer stripping square-wave voltammetry for detection of DNA hybridization and avidin in transgenic avidin maize. Anal. Chem. 2003;75:2663–2669. PubMed

Palecek E., Kizek R., Havran L., Billova S., Fojta M. Electrochemical enzyme-linked immunoassay in a DNA hybridization sensor. Anal. Chim. Acta. 2002;469:73–83.

Labuda J., Buckova M., Heilerova L., Silhar S., Stepanek I. Evaluation of the redox properties and anti/pro-oxidant effects of selected flavonoids by means of a DNA-based electrochemical biosensor. Anal. Bioanal. Chem. 2003;376:168–173. PubMed

Labuda J., Buckova M., Heilerova L., Caniova-Ziakova A., Brandsteterova E., Mattusch J., Wennrich R. Detection of antioxidative activity of plant extracts at the DNA-modified screen-printed electrode. Sensors. 2002;2:1–10.

Korbut O., Buckova M., Labuda J., Grundler P. Voltammetric detection of antioxidative properties of flavonoids using electrically heated DNA modified carbon paste electrode. Sensors. 2003;3:1–10.

Bukova M., Labuda J., Sandula J., Krizkova L., Stepanek I., Durackova Z. Detection of damage to DNA and antioxidative activity of yeast polysaccharides at the DNA-modified screen-printed electrode. Talanta. 2002;56:939–947. PubMed

Ovadekova R., Jantova S., Letasiova S., Stepanek I., Labuda J. Nanostructured electrochemical DNA biosensors for detection of the effect of berberine on DNA from cancer cells. Anal. Bioanal. Chem. 2006;386:2055–2062. PubMed

Hodek P., Hanustiak P., Krizkova J., Mikelova R., Krizkova S., Stiborova M., Trnkova L., Horna A., Beklova M., Kizek R. Toxicological aspects of flavonoid interaction with biomacromolecules. Neuroendocrinol. Lett. 2006;27:14–17. PubMed

Mikelova R., Hodek P., Hanustiak P., Adam V., Krizkova S., Havel L., Stiborova M., Horna A., Beklova M., Trnkova L., Kizek R. Determination of isoflavones using liquid chromatography with electrochemical detection. Acta Chim. Slov. 2007;54:92–97.

Zitka O., Huska D., Krizkova S., Adam V., Chavis G.J., Trnkova L., Horna A., Hubalek J., Kizek R. An investigation of glutathione-platinum(II) interactions by means of the flow injection analysis using glassy carbon electrode. Sensors. 2007;7:1256–1270.

Vitecek J., Petrlova J., Adam V., Havel L., Kramer K.J., Babula P., Kizek R. A fluorimetric sensor for detection of one living cell. Sensors. 2007;7:222–238.

Trnkova L., Jelen F., Petrlova J., Adam V., Potesil D., Kizek R. Elimination voltammetry with linear scan as a new detection method for DNA sensors. Sensors. 2005;5:448–464.

Supalkova V., Petrek J., Havel L., Krizkova S., Petrlova J., Adam V., Potesil D., Babula P., Beklova M., Horna A., Kizek R. Electrochemical sensors for detection of acetylsalicylic acid. Sensors. 2006;11:1483–1497.

Supalkova V., Petrek J., Baloun J., Adam V., Bartusek K., Trnkova L., Beklova M., Diopan V., Havel L., Kizek R. Multi-instrumental investigation of affecting of early somatic embryos of Spruce by cadmium(II) and lead(II) ions. Sensors. 2007;7:743–759.

Supalkova V., Huska D., Diopan V., Hanustiak P., Zitka O., Stejskal K., Baloun J., Pikula J., Havel L., Zehnalek J., Adam V., Trnkova L., Beklova M., Kizek R. Electroanalysis of plant thiols. Sensors. 2007;7:932–959.

Prasek J., Adamek M., Hubalek J., Adam V., Trnkova L., Kizek R. New hydrodynamic electrochemical arrangement for cadmium ions detection using thick-film chemical sensor electrodes. Sensors. 2006;11:1498–1512.

Krizkova S., Beklova M., Pikula J., Adam V., Horna A., Kizek R. Hazards of secondary bromadiolone intoxications evaluated using high-performance liquid chromatography with electrochemical detection. Sensors. 2007;7:1271–1286.

Hubalek J., Hradecky J., Adam V., Krystofova O., Huska D., Masarik M., Trnkova L., Horna A., Klosova K., Adamek M., Zehnalek J., Kizek R. Spectrometric and voltammetric analysis of urease – Nickel nanoelectrode as an electrochemical sensor. Sensors. 2007;7:1238–1255.

Babula P., Huska D., Hanustiak P., Baloun J., Krizkova S., Adam V., Hubalek J., Havel L., Zemlicka M., Horna A., Beklova M., Kizek R. Flow injection analysis coupled with carbon electrodes as the tool for analysis of naphthoquinones with respect to their content and functions in biological samples. Sensors. 2006;11:1466–1482.

Adam V., Zehnalek J., Petrlova J., Potesil D., Sures B., Trnkova L., Jelen F., Vitecek J., Kizek R. Phytochelatin modified electrode surface as a sensitive heavy metal ions biosensor. Sensors. 2005;5:70–84.

Brett A.M.O., Ghica M.E. Electrochemical oxidation of quercetin. Electroanalysis. 2003;15:1745–1750.

Corduneanu O., Janeiro P., Brett A.M.O. On the electrochemical oxidation of resveratrol. Electroanalysis. 2006;18:757–762.

Janeiro P., Corduneanu O., Brett A.M.O. Chrysin and (+/−)-taxifolin electrochemical oxidation mechanisms. Electroanalysis. 2005;17:1059–1064.

Ghica M.E., Brett A.M.O. Electrochemical oxidation of rutin. Electroanalysis. 2005;17:313–318.

Janeiro P., Brett A.M.O. Catechin electrochemical oxidation mechanisms. Anal. Chim. Acta. 2004;518:109–115.

Malagutti A.R., Zuin V.G., Cavalheiro E.T.G., Mazo L.H. Determination of rutin in green tea infusions using square-wave voltammetry with a rigid carbon-polyurethane composite electrode. Electroanalysis. 2006;18:1028–1034.

Zeng B.Z., Wei S.H., Xiao F., Zhao F.Q. Voltammetric behavior and determination of rutin at a single-walled carbon nanotubes modified gold electrode. Sens. Actuator B: Chem. 2006;115:240–246.

Ensafi A.A., Hajian R. Determination of rutin in pharmaceutical compounds and tea using cathodic adsorptive stripping voltammetry. Electroanalysis. 2006;18:579–585.

Timbola A.K., de Souza C.D., Giacomelli C., Spinelli A. Electrochemical oxidation of quercetin in hydro-alcoholic solution. J. Braz. Chem. Soc. 2006;17:139–148.

Temerk Y.M., Ibrahim H.S.M., Schuhmann W. Cathodic adsorptive stripping voltammetric determination of the antitumor drug rutin in pharmaceuticals, human urine, and blood serum. Microchim. Acta. 2006;153:7–13.

Firuzi O., Lacanna A., Petrucci R., Marrosu G., Saso L. Evaluation of the antioxidant activity of flavonoids by “ ferric reducing antioxidant power” assay and cyclic voltammetry. Biochim. Biophys. Acta-Gen. Subj. 2005;1721:174–184. PubMed

Zoulis N.E., Efstathiou C.E. Preconcentration at a carbon-paste electrode and determination by adsorptive-stripping voltammetry of rutin and other flavonoids. Anal. Chim. Acta. 1996;320:255–261.

Janeiro P., Brett A.M.O. Solid state electrochemical oxidation mechanisms of morin in aqueous media. Electroanalysis. 2005;17:733–738.

Oliveira-Brett A.M., Diculescu V.C. Electrochemical study of quercetin-DNA interactions: Part I. Analysis in incubated solutions. Bioelectrochemistry. 2004;64:133–141. PubMed

Oliveira-Brett A.M., Diculescu V.C. Electrochemical study of quercetin-DNA interactions - Part II. In situ sensing with DNA biosensors. Bioelectrochemistry. 2004;64:143–150. PubMed

Kizek R., Masarik M., Kramer K.J., Potesil D., Bailey M., Howard J.A., Klejdus B., Mikelova R., Adam V., Trnkova L., Jelen F. An analysis of avidin, biotin and their interaction at attomole levels by voltammetric and chromatographic techniques. Anal. Bioanal. Chem. 2005;381:1167–1178. PubMed

Stiborova M., Asfaw B., Frei E., Schmeiser H.H., Wiessler M. Benzenediazonium Ion Derived from Sudan-I Forms an 8-(Phenylazo)Guanine Adduct in DNA. Chem. Res. Toxicol. 1995;8:489–498. PubMed

Wiechelman K.J., Braun R.D., Fitzpatrick J.D. Investigation of the Bicinchoninic Acid Protein Assay - Identification of the Groups Responsible for Color Formation. Anal. Biochem. 1988;175:231–237. PubMed

Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 1964;239:2370–2378. PubMed

Polson A., Vonwechmar M.B., Vanregenmortel M.H.V. Isolation of Viral Igy Antibodies from Yolks of Immunized Hens. Immunol. Commun. 1980;9:475–493. PubMed

Polson A., Vonwechmar M.B., Fazakerley G. Antibodies to Proteins from Yolk of Immunized Hens. Immunol. Commun. 1980;9:495–514. PubMed

Hodek P., Koblas T., Rydlova H., Kubickova B., Sulc M., Hudecek J., Stiborova M. Chicken egg yolk as an excellent source of highly specific antibodies against cytochromes P450. Collect. Czech. Chem. Commun. 2004;69:659–673.

Guengerich F.P., Wang P., Davidson N.K. Estimation of Isozymes of Microsomal Cytochrome-P-450 in Rats, Rabbits, and Humans Using Immunochemical Staining Coupled with Sodium Dodecyl-Sulfate Polyacrylamide-Gel Electrophoresis. Biochemistry. 1982;21:1698–1706. PubMed

Klejdus B., Vacek J., Adam V., Zehnalek J., Kizek R., Trnkova L., Kuban V. Determination of isoflavones in soybean food and human urine using liquid chromatography with electrochemical detection. J. Chrom. B. 2004;806:101–111. PubMed

Potesil D., Petrlova J., Adam V., Vacek J., Klejdus B., Zehnalek J., Trnkova L., Havel L., Kizek R. Simultaneous femtomole determination of cysteine, reduced and oxidized glutathione, and phytochelatin in maize (Zea mays L.) kernels using high-performance liquid chromatography with electrochemical detection. J. Chrom. A. 2005;1084:134–144. PubMed

Petrlova J., Mikelova R., Stejskal K., Kleckerova A., Zitka O., Petrek J., Havel L., Zehnalek J., Adam V., Trnkova L., Kizek R. Simultaneous determination of eight biologically active thiol compounds using gradient elution-Liquid Chromatography with Coul-Array detection. J. Sep. Sci. 2006;29:1166–1173. PubMed

Jovanovic S.V., Steenken S., Tosic M., Marjanovic B., Simic M.G. Flavonoids as Antioxidants. J. Am. Chem. Soc. 1994;116:4846–4851.

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