Reactions of Linoleic Acid Peroxyl Radicals with Phenolic Antioxidants: A Pulse Radiolysis Study

References

• Abramovitch S., Rabani J. Pulse radiolytic investigations of peroxy radicals in aqueous solutions of acetate and glycine. Journal of Physical Chemistry 1976; 80: 1562–1565
   Web of Science ®Google Scholar
• Adams G.E., Aldrich J.E., Bisby R.H., Cundall R.B., Redpath J.L., Willson R.L. Selective free radical reactions with proteins and enzymes: reactions of inorganic radicals with amino acids. Radiation Research 1972; 49: 278–289
   PubMed Web of Science ®Google Scholar
• Adams G.E., Boag J.W., Currant J., Michael B.D. Absolute rate constants for the reaction of the hydroxyl radical with organic compounds. Pulse Radiolysis, M. Ebert, J.P. Keene, A.J. Swallow, J.H. Baxendale. Academic Press, New York 1965; 131–139
   Google Scholar
• Adams G.E., Michael B.D. Pulse radiolysis of benzoquinone and hydroquinone: semiquinone formation by water elimination from trihydroxy-cyclohexadienyl radicals. Transactions of the Faraday Society 1967; 63: 1171–1180
   Google Scholar
• Adams G.E., Wardman P. Free radicals in biology: the pulse radiolysis approach. Free Radicals in Biology, W.A. Pryor. Academic Press, New York 1977; III: 53–95
   Google Scholar
• Adams G.E., Willson R.L. Pulse radiolysis studies on the oxidation of organic radicals in aqueous solution. Transactions of the Faraday Society 1969; 65: 2981–2987
   Google Scholar
• Alfassi Z.B., Schuler R.H. Reaction of azide radicals with aromatic compounds. Azide as a selective oxidant. Journal of Physical Chemistry 1985; 89: 3359–3363
   Web of Science ®Google Scholar
• Al-Sheikhly M.I., Hissung A., Schuchmann H.-P., Schuchmann M.N., von Sonntag C. Radiolysis of dihydrouracil and dihydrothymine in aqueous solutions containing oxygen; first- and second-order reactions of the organic peroxyl radicals; the role of isopyrimidines as intermediates. Journal of the Chemical Society, Perkin II 1984; 601–608
   Google Scholar
• Baird N.C. MNDO calculations of the effects of substitution on antioxidant activity of phenols and vitamin E. Tetrahedron 1984; 40: 3383–3385
   Web of Science ®Google Scholar
• Barclay L.R.C., Ingold K.U. Autoxidation of biological molecules. 2. The autoxidation of a model membrane. A comparison of the autoxidation of egg lecithin phosphatidylcholine in water and in chlorobenzene. Journal of the American Chemical Society 1981; 103: 6478–6485
   Web of Science ®Google Scholar
• Barclay L.R.C., Locke S.J., MacNeil J.M., VanKessel J., Burton G.W., Ingold K.U. Autoxidation of micelles and model membranes. Quantitative kinetic measurements can be made by using either water-soluble or lipid-soluble initiators with water-soluble or lipid-soluble chain-breaking antioxidants. Journal of the American Chemical Society 1984; 106: 2479–2481
   Web of Science ®Google Scholar
• Baumann J., Wurm G., von Bruchhausen F. Hemmung der Prosta-glandinsynthetase durch Flavonoide und Phenolderivate im Vergleich mit deren Superoxid-Radikalfängereigenschaften. Archives of Pharmacology 1980; 313: 330–337
   Google Scholar
• Behar D. Pulse radiolysis studies on Br- in aqueous solution: the mechanism of Br-2 formation. Journal of Physical Chemistry 1972; 76: 1815–1818
   Web of Science ®Google Scholar
• Behar D., Bevan P.L.T., Scholes G. Pulse radiolysis of aqueous thiocyanate solutions. Nature of the intermediate transient species. Journal of Physical Chemistry 1972; 76: 1537–1544
   Web of Science ®Google Scholar
• Boozer C.E., Hammond G.S., Hamilton C.E., Sen J.N. Air oxidation of hydrocarbons. II. The stoichiometry and fate of inhibitors in benzene and chlorobenzene. Journal of the American Chemical Society 1955; 77: 3233–3237
   Web of Science ®Google Scholar
• Bors W. Semiquinone and phenoxyl radicals of phenolic antioxidants and model compounds: generation, spectral and kinetic properties. Life Chemistry Reports 1985; 3: 16–21
   Google Scholar
• Bors W., Erben-Russ M., Saran M. Generation and observation of fatty acid peroxyl radicals by pulse radiolysis. Superoxide and Superoxide Dismutases in Chemistry, Biology and Medicine, G. Rotilio. Elsevier, Amsterdam 1986; 38–40
   Google Scholar
• Bors W., Michel C., Saran M. Superoxide anions do not react with hydroperoxides. FEBS Letters 1979; 107: 403–406
   PubMed Web of Science ®Google Scholar
• Bors W., Michel C., Saran M. Determination of kinetic parameters of oxygen radicals by competition studies. CRC Handbook of Methods for Oxygen Radical Research, R.A. Greenwald. CRC Press, Boca Raton 1985; 181–188
   Google Scholar
• Bors W., Saran M. Radical scavenging by flavonoid antioxidants. Free Radical Research Communications 1986; 2: 289–297
   Google Scholar
• Bors W., Saran M., Michel C., Tait D. Formation and reactivities of oxygen free radicals. Advances on Oxygen Radicals and Radioprotectors, A. Breccia, C.L. Greenstock, M. Tamba. Lo Scarabeo Edit. Scient., Bologna 1984; 13–27
   Google Scholar
• Bothe E., Schuchmann M.N., Schulte-Frohlinde D., von Sonntag C. HO2 elimination from α-hydroxyalkylperoxyl radicals in aqueous solution. Photochemistry and Photobiology 1978; 28: 639–644
   Web of Science ®Google Scholar
• Burkey T.J., Griller D. Micellar systems as devices for enhancing the lifetimes and concentrations of free radicals. Journal of the American Chemical Society 1985; 107: 246–249
   Web of Science ®Google Scholar
• Burlakova E.B. Bioantioxidants and synthetic inhibitors of radical processes. Russian Chemical Reviews 1975; 44: 871–880
   Google Scholar
• Burton G.W., Ingold K.U. Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. Journal of the American Chemical Society 1981; 103: 6472–6477
   Web of Science ®Google Scholar
• Campbell T.W., Coppinger G.M. The reaction of t-butyl hydroperoxide with some phenols. Journal of the American Chemical Society 1952; 74: 1469–1471
   Web of Science ®Google Scholar
• Doba T., Burton G.W., Ingold K.U., Matsuo M. α-Tocopheroxyl decay: lack of effect of oxygen. Journal of the Chemical Society, Chemical Communications 1984; 461–462
   Google Scholar
• Dorfman L.M., Adams G.E. Reactivity of the hydroxyl radical in aqueous solution. IX. Reactions of the oxide radical ion. National Standard Reference Data Series. National Bureau of Standards, U.S. Department of Commerce, Washington, D.C. 1973, NSRDS-NBS 46
   Google Scholar
• Erben-Russ M., Bors W., Winter R., Saran M. The reaction of sulfite anion radical with polyunsaturated fatty acids. Radiation Physics and Chemistry 1986; 27: 419–427
   Web of Science ®Google Scholar
• Farhataziz, Ross A.B. Selected specific rates of reactions of transients from water in aqueous solution. III. Hydroxyl radical and perhydroxy radical and their radical ions. National Standard Reference Data Series. National Bureau of Standards, U.S. Department of Commerce, Washington, D.C. 1977, NSRDS-NBS 49
   Google Scholar
• Gebicki J.M., Allen A.O. Relationship between cmc and rate of radiolysis of aqueous sodium linoleate. Journal of Physical Chemistry 1969; 73: 2443–2445
   Web of Science ®Google Scholar
• Griva A.P., Denisov E.T. Kinetics of the reactions of 2,4,6-tri-t-butyl phenoxyl with cumene hydroperoxide, cumylperoxyl radicals, and molecular oxygen. International Journal of Chemical Kinetics 1973; 5: 869–877
   Google Scholar
• Hamberg M. Steric analysis of hydroperoxides formed by lipoxygenase oxygenation of linoleic acid. Analytical Biochemistry 1971; 43: 515–526
   PubMed Web of Science ®Google Scholar
• Hasegawa K., Patterson L.K. Pulse radiolysis studies in model lipid systems: formation and behavior of peroxy radicals in fatty acids. Photochemistry and Photobiology 1978; 28: 817–823
   Web of Science ®Google Scholar
• Hayon E., Simic M. Acid-base properties of organic peroxy radicals, ROOH, in aqueous solution. Journal of the American Chemical Society 1973; 95: 6681–6684
   Web of Science ®Google Scholar
• Heijman M.G.J., Heitzman A.J.P., Nauta H., Levine Y.K. A pulse radiolysis study of the reactions of OH/O- with linoleic acid in oxygen-free aqueous solution. Radiation Physics and Chemistry 1985; 26: 83–88
   Web of Science ®Google Scholar
• Hendry D.G., Mill T., Piszkiewicz L., Howard J.A., Eigenmann H.K. A critical review of H-atom transfer in the liquid phase: chlorine atom, alkyl, trichloromethyl, alkoxy, and alkylperoxy radicals. Journal of Physical Chemistry Reference Data Series 1974; 3: 937–938
   Google Scholar
• Howard J.A. Absolute rate constants for reactions of oxyl radicals. Advances in Free Radical Chemistry, G.H. Williams. Logos Press, London 1972; 4: 49–173
   Google Scholar
• Howard J.A., Ingold K.U. Absolute rate constants for hydrocarbon autoxidation. VI. Alkyl, aromatic and olefinic hydrocarbons. Canadian Journal of Chemistry 1967; 45: 793–892
   Web of Science ®Google Scholar
• Hug G.L. Optical spectra of nonmetallic inorganic transient species in aqueous solution. National Standard Reference Data Series. National Bureau of Standards, U.S. Department of Commerce, Washington, D.C. 1981, NSRDS-NBS 69
   Google Scholar
• Hunter E.P.L., Simic M.G. Kinetics of peroxy radical reactions with antioxidants. Oxy Radicals and their Scavenger Systems: Molecular Aspects, G. Cohen, R.A. Greenwald. Elsevier, New York 1983; 32–37
   Google Scholar
• Ilan Y., Rabani J., Henglein A. Pulse radiolytic investigations of peroxy radicals produced from 2-propanol and methanol. Journal of Physical Chemistry 1976; 80: 1558–1562
   Web of Science ®Google Scholar
• Ingold K.U. Peroxy radicals. Accounts of Chemical Research 1969; 2: 1–9
   Web of Science ®Google Scholar
• Ingold K.U. Rate constants for free radical reactions in solution. Free Radicals, J.K. Kochi. Wiley-Interscience, New York 1973; I: 37–112
   Google Scholar
• Jacob H.G. FORTRAN-Program for the evaluation of a local optimum of a bounded multivariable function without determination of its derivatives. Report PDV P6.1/22. 1975, M-IMR/3. (A modified version of this program was kindly provided by R. Trinoga, MPI für Strahlenchemie, Mülheim.)
   Google Scholar
• Johnston A.E., Zilch K.T., Selke E., Dutton H.J. Analysis of fatty acid oxidation products by countercurrent distribution methods. V. Low-temperature decomposition of methyl linoleate hydroperoxide. Journal of the American Oil Chemical Society 1961; 38: 367–371
   Web of Science ®Google Scholar
• Mahoney L.R. Inhibition of free radical reactions. III. Kinetic study of the reactions of peroxy radicals and phenoxy radicals in hydrocarbon systems. Journal of the American Chemical Society 1967; 89: 1895–1902
   Web of Science ®Google Scholar
• Mahoney L.R., DaRooge M.A. The kinetic behavior and thermochemical properties of phenoxy radicals. Journal of the American Chemical Society 1975; 97: 4722–4731
   Web of Science ®Google Scholar
• Maillard B., Ingold K.U., Scaiano J.C. Rate constants for the reactions of free radicals with oxygen in solution. Journal of the American Chemical Society 1983; 105: 5095–5099
   Web of Science ®Google Scholar
• Neta P., Fessenden R.W. Hydroxyl radical reactions with phenols and anilines as studied by ESR. Journal of Physical Chemistry 1974; 78: 523–529
   Web of Science ®Google Scholar
• Neta P., Schuler R.H. The mode of reaction of O- radical with aromatic systems. Radiation Research 1975; 64: 233–236
   PubMed Web of Science ®Google Scholar
• Niki E., Saito T., Kawakami A., Kamiya Y. Inhibition of oxidation of methyl linoleate in solution by vitamins E and C. Journal of Biological Chemistry 1984; 259: 4177–4182
   PubMed Web of Science ®Google Scholar
• Patterson L.K., Hasegawa K. Pulse radiolysis studies in model lipid systems. The influence of aggregation on kinetic behavior of OH induced radicals in aqueous sodium linoleate. Berichte der Bunsengesellschaft für Physikalische Chemie 1978; 82: 951–956
   Google Scholar
• Pohlman A., Mill T. Free radical oxidations in water: decomposition of azo initiators and oxidation of p-cresol and p-isopropylphenol. Journal of Organic Chemistry 1983; 48: 2133–2138
   Web of Science ®Google Scholar
• Porter N.A., Lehman L.S., Weber B.A., Smith K.J. Unified mechanism for polyunsaturated fatty acid (PUFA) autoxidation. Competition of peroxy radical hydrogen atom abstraction, β-scission and cyclization. Journal of the American Chemical Society 1981; 103: 6447–6455
   Web of Science ®Google Scholar
• Porter N.A., Weber B.A., Weenen H., Khan J.A. Autoxidation of polyunsaturated lipids. Factors controlling the stereochemistry of product hydroperoxides. Journal of the American Chemical Society 1980; 102: 5597–5601
   Web of Science ®Google Scholar
• Rabani J., Matheson M.S. Pulse radiolytic determination of pK for hydroxyl ionic dissociation in water. Journal of the American Chemical Society 1964; 86: 3175–3176
   Web of Science ®Google Scholar
• Rabani J., Matheson M.S. The pulse radiolysis of aqueous solutions of potassium ferro-cyanide. Journal of Physical Chemistry 1966; 70: 761–769
   Web of Science ®Google Scholar
• Raleigh J.A., Shum F.Y. Radioprotection in model lipid membranes by hydroxyl radical scavengers: supplementary role for α-tocopherol in scavenging secondary peroxy radicals. Radioprotectors and Anticarcinogens, O.F. Nygaard, M.G. Simic. Academic Press, New York 1983; 87–102
   Google Scholar
• Rao P.S., Ayres S.M., Mueller S. Identity of peroxy radicals produced from arachidonic acid in oxygenated solutions as studied by pulse radiolysis technique. Biochemical and Biophysical Research Communications 1982; 104: 1532–1536
   PubMed Web of Science ®Google Scholar
• Redpath J.L. Free radical reactions with simple biochemical systems. Journal of Chemical Education 1981; 58: 131–135
   Web of Science ®Google Scholar
• Ross A.B., Neta P. Rate constants for reactions of inorganic radicals in aqueous solution. National Standard Reference Data Series. National Bureau of Standards, U.S. Department of Commerce, Washington, D.C. 1979, NSRDS-NBS 65
   Google Scholar
• Russell G.A. Deuterium isotope effects in the autoxidation of aralkyl hydrocarbons. Mechanism of the interaction of peroxy radicals. Journal of the American Chemical Society 1957; 79: 3871–3877
   Web of Science ®Google Scholar
• Saran M., Vetter G., Erben-Russ M., Winter R., Kruse A., Michel C., Bors W. Pulse radiolysis equipment: a set-up for simultaneous multi-wavelength kinetic spectroscopy. Reviews of Scientific Instruments 1987; 58: 363–368
   Web of Science ®Google Scholar
• Schieberle P., Tsoukalas B., Grosch W. Decomposition of linoleic acid hydroperoxides by radicals. I. Structures of products of methyl 13-hydroperoxy-cis,trans-9,11-octadecadienoate. Zeitschrift für Lebensmittel Untersuchungs-Forschung 1979; 168: 448–456
   Google Scholar
• Schuchmann H.P., von Sonntag C. Methylperoxyl radicals: a study of the gamma-radiolysis of methane in oxygenated aqueous solutions. Zeitschrift für Naturforschung 1984; 39b: 217–221
   Google Scholar
• Schuchmann M.N., Zegota H., von Sonntag C. Reactions of peroxyl radicals derived from alkyl phosphates in aqueous solutions—model systems for DNA strand breakage. Oxygen Radicals in Chemistry and Biology, W. Bors, M. Saran, D. Tait. de Gruyter, Berlin 1984; 629–635
   Google Scholar
• Silbert L.S. Physical properties of organic peroxides. Organic Peroxides, D. Swern. Wiley-Interscience, New York 1971; II: 779–798
   Google Scholar
• Simic M. The chemistry of peroxy radicals and its implication to radiation biology. Fast Processes in Radiation Chemistry and Biology, G.E. Adams, E.M. Fielden, B.D. Michael. Institute of Physics/Wiley, London 1975; 162–179
   Google Scholar
• von Sonntag C. Radiation chemistry of carbohydrates and of the sugar moiety in DNA. Radiation Biology and Chemistry, Research Developments, H.E. Edwards, S. Navaratnam, B.J. Parsons, G.O. Phillips. Elsevier, Amsterdam 1979; 85–98
   Google Scholar
• Steenken S., Neta P. One electron redox potentials of phenols. Hydroxy- and amino-phenols and related compounds of biological interest. Journal of Physical Chemistry 1982; 86: 3661–3667
   Web of Science ®Google Scholar
• Takahama U. Redox reactions between kaempferol and illuminated chloroplasts. Plant Physiology 1983; 71: 598–601
   PubMed Web of Science ®Google Scholar
• Torel J., Cillard J., Cillard P. Antioxidant activity of flavonoids and reactivity with peroxy radicals. Phytochemistry 1986; 25: 383–385
   Web of Science ®Google Scholar
• Tsuchiya J., Niki E., Kamiya Y. Oxidation of lipids. IV. Formation and reaction of chromanoxyl radicals as studied by ESR. Bulletin of the Chemical Society of Japan 1983; 56: 229–232
   Web of Science ®Google Scholar
• Verhagen J., Vliegenthart J.F.G., Boldingh J. Micelle and acid-soap formation of linoleic acid and 13-l-hydroperoxylinoleic acid being substrates of lipoxygenase-1. Chemistry and Physics of Lipids 1978; 22: 255–259
   PubMed Web of Science ®Google Scholar
• Vladimirov Y.A., Olenev V.I., Suslova T.B., Cheremisina Z.P. Lipid peroxidation in mitochondrial membrane. Advances in Lipid Research 1980; 17: 174–249
   Google Scholar
• Weenen H., Porter N.A. Autoxidation of model membrane systems: cooxidation of polyunsaturated lecithins with steroids, fatty acids and α-tocopherol. Journal of the American Chemical Society 1982; 104: 5216–5221
   Google Scholar
• Winterle J., Dulin D., Mill T. Products and stoichiometry of reaction of vitamin E with alkylperoxy radicals. Journal of Organic Chemistry 1984; 49: 491–495
   Web of Science ®Google Scholar
• Yamamoto Y., Niki E., Kamiya Y. Oxidation of lipids. III. Oxidation of methyl linoleate in solution. Lipids 1982; 17: 870–877
   PubMed Web of Science ®Google Scholar
• Zegota H., Schuchmann M.N., von Sonntag C. Cyclopentylperoxyl and cyclohexylperoxyl radicals in aqueous solutions: a study by product analysis and pulse radiolysis. Journal of Physical Chemistry 1984; 88: 5589–5593
   Web of Science ®Google Scholar