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Part of the book series: NATO ASI Series ((NSSA,volume 296))

Abstract

Flavonoids belong to the recently popular phytochemicals (Huang, Osawa, Ho, and Rosen, 1994; Ho, Osawa, Huang, and Rosen, 1994; Manach, Régérat, Texier, Agullo, Demigné, and Rémésy, 1996), plant products with potential benefit for human health. Since the compounds exist as ubiquitous secondary plant metabolites, they are an important part of human diet (Das and Ramanathan, 1992; Hertog, Feskens, Hollman, and Katan, 1993; Ktihnau, 1976; Stavric and Matula, 1992). They are also considered as the active principles in many medicinal plants (Wollenweber, 1988; Xin, Zhao, Li, and Hou, 1990). Due to the pronounced antioxidative potential of flavonoids, there is considerable interest in the structure and reactions of the flavonoid aroxyl radicals as obligatory intermediates during radical-scavenging reactions. Indeed the preferred mechanistic interpretation of the antioxidative effect of flavonoids lies in the radical-scavenging properties of these compounds, both in model systems and under in vitro conditions (see Bors, Michel, and Saran, 1994; Bors, Heller, Michel, and Stettmaier, 1996; Rice-Evans, Miller, and Paganga, 1996).

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References

  • Afanas’ev, LB., Dorozhko, A.I., Brodskii, A.V., Kostyuk, V.A., and Potapovitch, A.I., 1989, Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation, Biochem. Pharmacol. 38: 1763–1769

    Article  Google Scholar 

  • Baumann, J., Wurm, G., von Bruchhausen, F., 1980, Hemmung der Prostaglandin-Synthetase durch Flavonoide und Phenolderivate im Vergleich mit deren 02 Radikalfängereigenschaften. Arch. Pharmacol. 313: 330–337

    Article  CAS  Google Scholar 

  • Belyakov, V.A., Roginsky, V.A., and Bors, W., 1995, Rate constants for the reaction of peroxyl free radical with flavonoids and related compounds as determined by the kinetic chemiluminescence method, J. Chem. Soc., Perkin II, 1995: 2319–26

    Article  Google Scholar 

  • Bors, W., and Saran, M., 1987, Radical scavenging by flavonoid antioxidants, Free Radical Res. Comm. 2: 289–294

    Article  CAS  Google Scholar 

  • Bors, W., Saran, M., Michel, C., and Tait, D., 1984, Formation and reactivities of oxygen free radicals. in: Advances on Oxygen Radicals and Radioprotectors, ( A. Breccia, C.L. Greenstock, and M. Tamba, eds.), pp. 13–27, Ed. Scient. Lo Scarabeo, Bologna

    Chapter  Google Scholar 

  • Bors, W., Michel, C., and Saran, M., 1985, Determination of kinetic parameters of oxygen radicals by competition studies. In: CRC Handbook of Methods for Oxygen Radical Research. ( R.A. Greenwald, ed.), pp. 181–188, CRC Press, Boca Raton, FL

    Google Scholar 

  • Bors, W., Heller, W., Michel, C., and Saran, M., 1990, Flavonoids as antioxidants: determination of radical scavenging efficiencies, Meth. Enzymol. 186: 343–354

    Article  CAS  Google Scholar 

  • Bors, W., Heller, W., Michel, C., and Saran, M., I992a, Structural principles of flavonoid antioxidants. In: Free Radicals and the Liver,(G. Csomos and J. Feher, eds.), pp. 77–95, Springer, Berlin

    Google Scholar 

  • Bors, W., Michel, C., and Saran, M., 19926, Determination of rate constants for antioxidant activity and use of the crocin assay. In: Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications. (A.S.H. Ong and L. Packer, eds.), pp. 52–64, Birkhäuser, Basel

    Google Scholar 

  • Bors, W., Michel, C., and Saran, M., 1994, Flavonoid antioxidants: rate constants for reactions with oxygen radicals. Meth Enzymol 234: 420–429

    Article  CAS  Google Scholar 

  • Bors, W., Michel, C., and Schikora, S., 1995, Interaction of flavonoids with ascorbate and determination of their univalent redox potentials: a pulse radiolysis study, Free Radical Biol. Med. 19: 45–52

    Article  CAS  Google Scholar 

  • Bors, W., Heller, W., Michel, C., and Stettmaier, K., 1996, Flavonoids and Polyphenols: Chemistry and Biology, in: Handbook of Antioxidants, ( E. Cadenas and L. Packer, eds.), pp. 409–466, Marcel Dekker, New York, NY

    Google Scholar 

  • Brown, J.P., 1980, A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat. Res. 75: 243–277

    Article  CAS  Google Scholar 

  • Brown, S.B., Rajananda, V., Holroyd, J.A., and Evans, E.G.V., 1982, A study of the mechanism of quercetin oxygenation by 180 labelling. A comparison of the mechanism with that of haem degradation, Biochem. J. 205: 239–244

    CAS  Google Scholar 

  • Canada, A.T., Giannella, E., Nguyen, T.D., and Mason, R.P., 1990, The production of reactive oxygen species by dietary flavonols, Free Radical Biol. Med. 9: 441–449

    Article  CAS  Google Scholar 

  • Chen, Y., Zheng, R., Jia, Z., and Ju, Y., 1990, Flavonoids as superoxide scavengers and antioxidants, Free Radical Biol. Med. 9: 19–21

    Article  Google Scholar 

  • Cotelle, N., Bernier, J.L., Hénichart, J.P., Catteau, J.P., Gaydou, E., and Wallet, J.C., 1992, Scavenger and antioxidant properties of ten synthetic flavones, Free Radical Biol. Med. 13: 211–219

    Article  CAS  Google Scholar 

  • Cotelle, N., Bernier, J.L., Catteau, J.P., Pommery, J., Wallet, J.C., and Gaydou, E.M., 1996, Antioxidant properties of hydroxy-flavones, Free Radical Biol. Med. 20: 35–43

    Article  CAS  Google Scholar 

  • Das, N.P., and Ramanathan, L., 1992, Studies on flavonoids and related compounds as antioxidants in food. In: Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications, ( A.S.H. Ong and L. Packer, eds.), pp. 295–306, Birkhäuser, Basel

    Chapter  Google Scholar 

  • Erben-Russ, M., Bors, W., and Saran, M., 1987, Reactions of linoleic acid peroxyl radicals with phenolic antioxidants: a pulse radiolysis study. Int. J. Radiat. Biol. 52: 393–412

    Article  CAS  Google Scholar 

  • György, I., Blazovics, A., Feher, J., and Földiak, G., 1990, Reactions of inorganic free radicals with liver protecting drugs, Radiat. Phys. Chem. 36: 165–167

    Google Scholar 

  • György, I., Antus, S., and Földiak, G., 1992a, Pulse radiolysis of silybin: one-electron oxidation of the flavonoid at neutral pH, Radiat. Phys. Chem. 39: 81–84

    Google Scholar 

  • György, I., Antus, S., Blazovics, A., and Földiak, G., 1992b, Substituent effects in the free radical reactions of silybin: radiation-induced oxidation of the flavonoid at neutral pH, Int. J. Radiat. Biol. 61: 603–609

    Article  Google Scholar 

  • Hatcher, J.F., and Bryan, G.T., 1985, Factors affecting the mutagenic activity of quercetin for Salmonella typhimurium TA98: metal ions, antioxidants and pH, Mutat. Res. 148: 13–23

    Article  CAS  Google Scholar 

  • Hathway, D.E., and Seakins, J.W.T., 1957, Autoxidation of polyphenols. III. Autoxidation in neutral aqueous solution of flavans related to catechin, J. Chem. Soc., 1957: 1562–1566

    Article  Google Scholar 

  • Hertog, M.G.L., Feskens, E.J.M., Holtman, P.C.H., and Katan, M.B., 1993, Dietary antioxidant flavonoids and risk of coronary heart disease in the Zutphen Elderly Study, Lancet 342: 1007–11

    Article  CAS  Google Scholar 

  • Ho, C.T., Osawa, T., Huang, M.T., and Rosen, R.T. (eds.), 1994, Food Phytochemicals for Cancer Prevention. II. Teas, Spices, and Herbs. ACS Sympos. Ser. 547, ACS Press, Washington, DC

    Google Scholar 

  • Hodnick, W.F., Milosavljevic, E.B., Nelson, J.H., and Pardini, R.S., 1988, Electrochemistry of flavonoids. Relationships between redox potentials, inhibition of mitochondrial respiration, and production of oxygen radicals by flavonoids, Biochem. Pharmacol. 37: 2607–11

    Article  CAS  Google Scholar 

  • Hu, J.P., Calomme, M., Lasure, A., de Bruyne, T., Pieters, L., Vlietinck, A., and vanden Berghe, D.A., 1995, Structure-activity relationship of flavonoids with superoxide scavenging activity, Biol. Trace Elem. Res. 47: 327–331

    Article  CAS  Google Scholar 

  • Huang, M.T., Osawa, T., Ho, C.T., and Rosen, R.T. (eds.), 1994, Food Phytochemicals for Cancer Prevention. I. Fruits and Vegetables. ACS Sympos. Ser. 546, ACS Press, Washington, DC

    Google Scholar 

  • Huguet, A.I., Manez, S., and Alcaraz, M.J., 1990, Superoxide scavenging properties of flavonoids in a non-enzymic system, Z. Naturforsch. 45c: 19–24

    CAS  Google Scholar 

  • Husain, S.R., Cillard, J., and Cillard, P., 1987, Hydroxyl radical scavenging activity of flavonoids, Phytochemistry 26: 2489–91

    Article  CAS  Google Scholar 

  • Jensen, O.N., and Pedersen, J.A., 1983, The oxidative transformations of (+)-catechin and (-)- epicatechin as studied by ESR, Tetrahedron 39: 1609–15

    Article  CAS  Google Scholar 

  • Jovanovic, S.V., Steenken, S., Tosic, M., Marjanovic, B., and Simic, M.G., 1994, Flavonoids as antioxidants, J. Am. Chem. Soc. 116: 4846–51

    Article  CAS  Google Scholar 

  • Jovanovic, S.V., Hara, Y., Steenken, S., and Simic, M.G., 1995, Antioxidant potential of gallocatechins. A pulse radiolysis and laser photolysis study. J. Am. Chem. Soc. 117: 9881–9888

    Article  CAS  Google Scholar 

  • Jovanovic, S.V., Steenken, S., Hara, Y., and Simic, M.G., 1996, Reduction potentials of flavonoid and model phenoxyl radicals. Which ring in flavonoids is responsible for antioxidant activity? J. Chem. Soc., Perkin Trans. II, 1996: 2497–2504

    Article  Google Scholar 

  • Krol, W., Czuba, Z.P., Threadgill, M.D., Cunningham, B.D.M., and Pietsz, G., 1995, Inhibition of nitric oxide (NO) production in murine macrophages by flavones, Biochem. Pharmacol. 50: 1031–1035

    Article  CAS  Google Scholar 

  • Kühnau, J., 1976, The flavonoids. A class of semi-essential food components: their role in human nutrition, World Rev. Nutr. Diet. 24: 117–191

    Google Scholar 

  • Kuhnle, J.A., Windle, J.J., and Waiss, A.C., 1969, EPR spectra of flavonoid anion-radicals, J. Chem. Soc. B, 1969: 613–616

    Article  Google Scholar 

  • MacGregor, J.T., 1986, Mutagenic and carcinogenic effects of flavonoids, in: Plant Flavonoids in Biology and Medicine, ( V. Cody, E. Middleton, and J.B. Harborne, eds.), pp. 411–424, A.R. Liss, New York, N

    Google Scholar 

  • Manach, C., Régérat, F., Texier, O., Agullo, G., Demigné, C., and Rémésy, C., 1996, Bioavailability, metabolism and physiological impact of 4-oxo-flavonoids, Nutrit. Res. 16: 517–544

    Article  Google Scholar 

  • Minnunni, M., Wolleb, U., Müller, O., Pfeifer, A., and Äschbacher, H.U., 1992, Natural antioxidants as inhibitors of oxygen species induced mutagenicity, Mutat. Res. 269: 193–200

    Article  CAS  Google Scholar 

  • Nagao, M., Morita, N., Yahagi, T., Shimizu, M., Kuroyanagi, M., Fukuoka, M., Yoshihira, K., Natori, S., Fujino, T., and Sugimura, T., 1981, Mutagenicities of 61 flavonoids and 11 related compounds, Environ. Mutagen. 3: 401–419

    Article  CAS  Google Scholar 

  • Pardini, R.S., 1995, Toxicity of oxygen from naturally occurring redox-active pro-oxidants, Arch. Insect Biochem. Physiol. 29: 101–118

    Article  CAS  Google Scholar 

  • Pelter, A., Bradshaw, J., and Warren, R.F., 1971, Oxidation experiments with flavonoids, Phytochemistry 10: 835–850

    Article  CAS  Google Scholar 

  • Puppo, A., 1992, Effect of flavonoids on OH radical formation by Fenton-type reactions: influence of the iron chelator, Phytochemistry 31: 85–88

    Article  CAS  Google Scholar 

  • Rashid, K.A., Mullin, C.A., and Mumma, R.O., 1986, Structure-mutagenicity relationships of chalcones and their oxides in the Salmonella assay, Mutat. Res. 169: 71–79

    Article  CAS  Google Scholar 

  • Rice-Evans, C.A., Miller, N.J., and Paganga, G., 1996, Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Radical Biol. Med. 20: 933–956

    Article  CAS  Google Scholar 

  • Robak, J., and Gryglewski, R.J., 1988, Flavonoids are scavengers of superoxide anions, Biochem. Pharmacol. 37: 837–841

    Article  CAS  Google Scholar 

  • Roginsky, V.A., Barsukova, T.K., Remorova, A.A., and Bors, W., 1996, Moderate antioxidative efficiencies of flavonoids during peroxidation of methyl linoleate in homogeneous and micellar solutions, J. Am. Oil Chem. Soc., 73: 777–786

    Article  CAS  Google Scholar 

  • Rueff, J., Laires, A., Gaspar, J., Borba, H., and Rodrigues, A., 1992, Oxygen species and the genotoxicity of quercetin, Mutat. Res. 265: 75–81

    Article  CAS  Google Scholar 

  • Salah, N., Miller, N.J., Paganga, G., Tijburg, L., Bolwell, G.E, and Rice-Evans, C., 1995, Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants, Arch. Biochem. Biophys. 322: 339–346

    Article  CAS  Google Scholar 

  • Saran, M., Vetter, G., Erben-Russ, M., Winter, R., Kruse, A., Michel, C., and Bors, W., 1987, Pulse radiolysis equipment: a setup for simultaneous multiwavelength kinetic spectroscopy, Rev. Sci. Instrum. 58: 363–368

    Article  CAS  Google Scholar 

  • Sichel, G., Corsaro, C., Scalia, M., di Bilio, A.J., and Bonomo, R.P., 1991, In vitro scavenger activity of some flavonoids and melanins against 0 2 - Free Radical Biol. Med. 11: 1–8

    Article  CAS  Google Scholar 

  • Stavric, B., and Matula, T.I., 1992, Flavonoids in foods: their significance for nutrition and health, in: Lipid-Soluble Antioxidants: Biochemistry and Clinical Applications, ( A.S.H. Ong and L. Packer, eds.), pp. 274–294, Birkhäuser, Basel

    Chapter  Google Scholar 

  • Steenken, S., and Neta, P., 1982, One-electron redox potentials of phenols. Hydroxy-and aminophenols and related compounds of biological interest, J. Phys. Chem. 86: 3661–67

    Article  CAS  Google Scholar 

  • Suzuki, N., Goto, A., Oguni, I., Mashiko, S., and Nomoto, T., 1991, Reaction rate constants of tea leaf catechins with superoxide: superoxide-dismutase (SOD)-like activity measured by Cypridina luciferin analogue chemiluminescence, Chem. Express 6: 655–658

    CAS  Google Scholar 

  • Sweeny, J.G., Iacobucci, G.A., Brusick, D., and Jagannath, D.R., 1981, Structure-activity relationships in the mutagenicity of quinone methides of 7-hydroxy-flavylium salts for Salmonella typhimurium, Mutat. Res. 82: 275–283

    Article  CAS  Google Scholar 

  • Teel, R.W., and Castonguay, A., 1992, Antimutagenic effects of polyphenolic compounds, Cancer Lett. 66: 107–113

    Article  CAS  Google Scholar 

  • Torel, J., Cillard, J., and Cillard, P., 1986, Antioxidant activity of flavonoids and reactivity with peroxy radicals, Phytochemistry 25: 383–385

    Article  CAS  Google Scholar 

  • Ueno, I., Kohno, M., Haraikawa, K., and Hirono, I., 1984, Interaction between quercetin and Of radical. Reduction of the quercetin mutagenicity, J. Pharm. Dyn. 7: 798–803

    Article  CAS  Google Scholar 

  • van Acker, S.A.B.E., Tromp, M.N.J.L., Haenen, G.R.M.M., van der Vijgh, W.J.F., and Bast, A., 1995, Flavonoids as scavengers of nitric oxide radical, Biochem. Biophys. Res. Comm. 214: 755–759

    Article  Google Scholar 

  • Wollenweber, E., 1988, Occurrence of flavonoid aglycones in medicinal plants. in: Plant Flavonoids in Biology and Medicine II: Biochemical, Cellular, and Medicinal Properties, ( V. Cody, E. Middleton, J.B. Harborne, and Beretz, A., eds.), pp. 45–55, A.R. Liss, New York, NY

    Google Scholar 

  • Xin, W.J., Zhao, B.L., Li, X.J., and Hou, J.W., 1990, Scavenging effects of chinese herbs and natural health products on active oxygen radicals, Res. Chem. Intermed. 14: 171–183

    Article  CAS  Google Scholar 

  • Yoshioka, H., Sugiura, K., Kawahara, R., Fujita, T., Makino, M., Kamiya, M., and Tsuyumu, S., 1991, Formation of radicals and chemiluminescence during the autoxidation of tea catechins, Agric. Biol. Chem. 55: 2717–23

    Article  CAS  Google Scholar 

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Bors, W., Michel, C., Heller, W., Sandermann, H. (1998). Flavonoid Radicals. In: Özben, T. (eds) Free Radicals, Oxidative Stress, and Antioxidants. NATO ASI Series, vol 296. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-2907-8_8

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