123
Views
87
CrossRef citations to date
0
Altmetric
Original Article

Flavonoid Deactivation of Ferrylmyoglobin in Relation to Ease of Oxidation as Determined by Cyclic Voltammetry

&
Pages 335-351 | Received 02 Oct 1997, Published online: 07 Jul 2009

References

  • Dragsted L. O., Strube M., Larsen J. C. Cancer-protective factors in fruits and vegetables: biochemical and biological background. Pharmacology & Toxicology 1993; 72: 116–135
  • Formica J. V., Regelson W. Review of the biology of quercetin and related bioflavonoids. Food and Chemical Toxicology 1995; 33: 1061–1080
  • The Flavonoids. Advances in Research Since 1980, J. B. Harbome. Chapman & Hall, London 1988
  • Justesen U., Knuthsen P., Leth T. Determination of plant polyphenols in Danish foodstuffs by HPLC-UV and LC-MS detection. Cancer Letters 1997; 114: 165–167
  • Kühnau J. The flavonoids. A class of semi-essential food components: Their role in human nutrition. World Review of Nutrition and Dietetics 1976; 24: 117–191
  • Paganga G., Rice-Evans C. A. The identification of flavonoids as glycosides in human plasma. FEBS Letters 1997; 401: 78–82
  • Jovanovic S. V., Steenken S., Tosic M., Marjanovic B., Simic B. M. Flavonoids as antioxidants. Journal of the American Chemical Society 1994; 116: 4846–4851
  • Foti M., Piattelli M., Baratta M. T., Ruberto G. Flavonoids, coumarins and cinnamic acids as antioxidants in a micellar system. Structureactivity relationship. Journal of Agricultural and Food Chemisty 1996; 44: 497–501
  • van Acker S. A. B. E., van den Berg D. M., Tromp N. J. L., Griffioen D. H. W. P., van Bennekom W. J., van der Vijgh F., Bast A. Structural aspects of antioxidant activity of flavonoids. Free Radical Biology & Medicine 1996; 20: 331–342
  • Rice-Evans C. A., Miller N. J., Paganga G. Structure—antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology & Medicine 1996; 20: 933–956
  • Cao G., Sofic E., Prior R. L. Antioxidant and prooxidant behaviour of flavonoids: structureactivity relationships. Free Radical Biology & Medicine 1997; 22: 749–760
  • Bors W., Heller W., Michel C., Saran M. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods in Enzymology 1990; 186: 343–355
  • Eddy L., Arduini A., Okonski F., Hochstein P. The detection of hypervalent states of myoglobin by reflectance spectrophotomehy in cardiac ischemic/ reperfusion injury. FASEB Journal 1990; 4: A1219, (5535)
  • Galaris D., Sevanian A., Cadenas E., Hochstein P. FerryImyogIobin-catalyzed linoleic acid peroxida-tion. Archives of Biochemistry and Biophysics 1990; 281: 163–169
  • Østdal H., Daneshvar B., Skibsted L. H. Reduction of ferrylmyoglobin by β-lactoglobulin. Free Radical Research 1996; 24: 429–438
  • Laranjinha J., Almeida L., Madeira V. Reduction of ferrylmyoglobin by dietary phenolic acid derivatives of cinnamic acid. Free Radical Biology & Medicine 1995; 19: 329–337
  • Guilivi C., Cadenas E. Ferrylmyoglobin: Formation and chemical reactivity towards electron-donating compounds. Methods in Enzymology 1994; 233: 189–202
  • Bard A. J., Faulkner L. R. Electrochemical Methods. Wiley, New York 1980
  • Mikkelsen A., Skibsted L. H. Acid-catalysed reduction of ferrylmyoglobin: Product distribution and kinetics of autoreduction and reduction by NADH. Zeitschrift für Lebensmittel-Untersuchung und-Forschung 1995; 200: 171–177
  • Nelson D. P., Kiesow L. A. Enthalpy of decomposition of hydrogen peroxide by catalase at 25°C (with molar extinction coefficients of H2O2 solutions in the UV). Analytical Biochemistry 1972; 49: 474–478
  • Whitburn K. D., Shieh J. J., Sellers R. M., Hoffman M., 2., Taub I. A. Redox transformations in ferri-myoglobin induced by radiation-generated radicals in aqueous solution. Journal of Biological Chemistry 1982; 257: 1860–1869
  • Steenken S., Neta P. One-electron redox potentials of phenols. Hydroxy- and aminophenols and related compounds of biological interest. Journal of Physical Chemistry 1982; 86: 3661–3667
  • Hodnick W. F., Milosavljevic E. B., Nelson J. H., Pardini R. S. Electrochemistry of flavonoids. Relationships between redox potentials, inhibition of mitochon-drial respiration, and production of oxygen radicals by flavonoids. Biochemical Pharmacology 1988; 37: 2607–2611
  • Hendrickson H. P., Kaufman A. D., Lunte C. E. Electrochemistry of catechol-containing flavonoids. Journal of Pharmaceutical & Biomedical Analysis 1994; 12: 325–334
  • Hendrickson H. P., Sahafayen M., Bell M. A., Kaufman A. D., Hadwiger M. E., Lunte C. E. Relationship of flavonoid oxidation potential and effect on rat hepatic microsomal metabolism of benzene and phenol. Journal of Pharmaceutical & Biomedical Analysis 1994; 12: 335–341
  • Bors W., Michel C., Schikora S. Interaction of flavonoids with ascorbate and determination of their univalent redox potentials: A pulse radiolysis study. Free Radical Biology & Medicine 1995; 19: 4552
  • Jovanovic S. V., Steenken S., Hara Y., Simic M. G. Reduction potentials of flavonoid and model phenoxyl radicals. Which ring is responsible for antiox-idant activity?. Journal of the Chemical Society: Perkin Transactions 1996; 2: 2497–2504
  • van Acker S. A. B. E., de Groot M. J., van den Berg D., Tromp M. N. J. L., den Kelder G. D., van der Vijgh W. J. F., Bast A. A quantum chemical explanation of the antioxidant activity of flavonoids. Chemical Research in Toxicology 1996; 9: 1305–1312
  • Castelluccio C., Paganga G., Melikian N., Bolwell G. P., Pridham J., Sampson J., Rice-Evans C. Antioxidant potential of intermediates in phenylpro-panoid metabolism in higher plants. FEBS Letters 7995; 368: 188–192
  • Koppenol W. H. Reactions involving singlet oxygen and the superoxide anion. Nature 1976; 262: 420–421
  • George P., Irvine D. H. A possible structure for the higher oxidation state of metmyoglobin. Biochemical Journal 1955; 60: 596–604
  • Candeias L. P., Folkes L. K., Wardman P. Factors controlling the substrate specificity of peroxi-dases: Kinetics and thermodynamics of the reaction of horseradish peroxidase compound I with phenol and indole-3-acetic acids. Biochemistry 1997; 36: 7081–7085
  • Tournaire C., Croux S., Maurette M., Beck I., Hocquaux M., Braun A. M., Oliveros E. Antioxidant activity of flavonoids: efficiency of singlet oxygen (1 g) quenching. Journal of Photochemistry and Photobiol-ogy B: Biology 1993; 19: 205–215
  • Laranjinha J., Vieira O., Madeira V., Almeida L. Two related phenolic antioxidants with opposite effects on Vitamin E content in low density lipoproteins oxidized by ferrylmyoglobin: Consumption vs. regeneration. Archives of Biochemistry and Biophysics 1995; 323: 373–381
  • Kröger-Ohlsen M., Skibsted L. H. Kinetics and mechanism of reduction of ferrylmyoglobin by ascorbate and D-isoascorbate. Journal of Agricultural and Food Chemistry 1997; 45: 668–676
  • Bors W., Saran M. Radical scavenging by flavonoid antioxidants. Free Radical Research Communications 1987; 2: 289–294
  • Kanner J., Frankel E., Granit R., German B., Kinsella J. E. Natural antioxidants ingrapes and wines. Journal of Agricultural and Food Chemistry 1994; 42: 64–69
  • Jørgensen L. V., Andersen H. J., Skibsted L. H. Kinetics of reduction of hypervalent iron in myoglobin by crocin in aqueous solution. Free Radical Research 1997; 27: 73–87
  • Mukai K., Oka W., Watanabe K., Egawa Y., Nagaoka S. Kinetic study of free-radical-scavenging action of flavonoids in homogenous and Triton X-100 micellar solutions. Journal of Physical Chemistry A 1997; 101: 3746–3753
  • Agrawal P. K., Schneider H. J. Deprotonation induced 13C NMR shifts in phenols and flavonoids. Tetrahedron Letters 1983; 24: 177–180
  • Grindberg L. N., Rachmilewitz E. A., Newmark H. Protective effects of rutin against hemoglobin oxidation. Biochemical Pharmacology 1994; 48: 643–649

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.