Activated oxygen species and oxidation of food constituents.

Activated oxygen species which may be important in initiating oxidative changes in foods include singlet oxygen, hydroxyl radical, ozone, superoxide anion (perhydroxyl radical at low pH), and hydrogen peroxide. Chemical and enzymic reactions known to occur in biological materials can generate singlet oxygen, hydroxyl radical, superoxide anion, and hydrogen peroxide. Ozone is primarily a product of photoreactions in polluted air. Reactions involving singlet oxygen, hydroxyl radical, and ozone with food constituents can ultimately yield peroxides which decompose to initiate oxidative chain reactions. Superoxide anion and hydrogen peroxide are relatively inert toward organic molecules but can decompose to produce the more reactive singlet oxygen and hydroxyl radical. Inhibition of reactions initiated by reactive oxygen species in foods should be very important in preserving the oxidative stability of foods. The generation, detection, measurement, reaction, and inhibition of reactions of active oxygen species are surveyed in this review.

[1]  J. Bolton,et al.  Superoxide formation in spinach chloroplasts: electron spin resonance detection by spin trapping. , 1975, Biochemical and biophysical research communications.

[2]  D. Armstrong,et al.  Glutathione mediation of papain inactivation by hydrogen peroxide and hydroxyl radicals. , 1977, Radiation research.

[3]  James L. Johnson,et al.  Ozonolysis. II.1 The Effect of Pyridine on the Ozonolysis of 4,22-Stigmastadien-3-one2 , 1958 .

[4]  B. Halliwell,et al.  Ascorbic acid, metal ions and the superoxide radical. , 1976, The Biochemical journal.

[5]  W. Bors,et al.  The relevance of the superoxide anion radical in biological systems. , 1974, Current topics in radiation research quarterly.

[6]  D. Wiles,et al.  Photooxidation of unsaturated oils: Effects of singlet oxygen quenchers , 1976 .

[7]  R. Jenness,et al.  Principles of Dairy Chemistry , 1959 .

[8]  N. Krinsky Singlet oxygen in biological systems , 1977 .

[9]  I. Fridovich,et al.  Superoxide dismutase and the oxygen enhancement of radiation lethality. , 1976, Archives of biochemistry and biophysics.

[10]  R. Matthews,et al.  The production of superoxide anion radicals in the reaction of reduced flavins and flavoproteins with molecular oxygen. , 1969, Biochemical and biophysical research communications.

[11]  K. Tipton A sensitive fluorometric assay for monoamine oxidase. , 1969, Analytical biochemistry.

[12]  B. Babior,et al.  Biological defense mechanisms. The production by leukocytes of superoxide, a potential bactericidal agent. , 1973, The Journal of clinical investigation.

[13]  J. Spinks,et al.  Introduction to Radiation Chemistry , 1964 .

[14]  H. Beinert,et al.  On the formation of the superoxide anion radical during the reaction of reduced iron-sulfur proteins with oxygen. , 1969, Biochemical and biophysical research communications.

[15]  I. Fridovich,et al.  The interaction of bovine erythrocyte superoxide dismutase with hydrogen peroxide: inactivation of the enzyme. , 1975, Biochemistry.

[16]  C. Foote CHAPTER 3 – Photosensitized Oxidation and Singlet Oxygen: Consequences in Biological Systems , 1976 .

[17]  M. Nakano,et al.  Spectroscopic evidence for the generation of singlet oxygen in the reduced nicotinamide adenine dinucleotide phosphate-dependent microsomal lipid peroxidation system. , 1975, The Journal of biological chemistry.

[18]  I. Rosenthal,et al.  Electron transfer interactions between superoxide ion and organic compounds , 1973 .

[19]  G. Inglett,et al.  Dye-sensitized photooxidation of .alpha.-tocopherol , 1972 .

[20]  K. Enns,et al.  The Photochemical Oxidation of Ethylenediaminetetraacetic Acid and Methionine by Ribolflavin1 , 1965 .

[21]  H. Rawls,et al.  A possible role for singlet oxygen in the initiation of fatty acid autoxidation , 1970 .

[22]  P. McCay,et al.  Enzyme-Generated Free Radicals as Initiators of Lipid Peroxidation in Biological Membranes , 1976 .

[23]  A. Bard,et al.  Production of Singlet Oxygen in Electrogenerated Radical Ion Electron Transfer Reactions , 1973 .

[24]  J. Spikes,et al.  DYE‐SENSITIZED PHOTOOXIDATION OF PROTEINS * , 1970 .

[25]  I. Fridovich,et al.  The utility of superoxide dismutase in studying free radical reactions. I. Radicals generated by the interaction of sulfite, dimethyl sulfoxide, and oxygen. , 1969, The Journal of biological chemistry.

[26]  M. Nishikimi The generation of superoxide anion in the reaction of tetrahydropteridines with molecular oxygen. , 1975, Archives of biochemistry and biophysics.

[27]  R. Santus,et al.  N‐FORMYL‐KYNURENINE, A TRYPTOPHAN PHOTOOXIDATION PRODUCT, AS A PHOTODYNAMIC SENSITIZER , 1974, Photochemistry and photobiology.

[28]  A. Glazer,et al.  Chemical modification of proteins: Selected methods and analytical procedures , 1975 .

[29]  J. Gutteridge,et al.  The protective action of superoxide dismutase on metal-ion catalysed peroxidation of phospholipids. , 1977, Biochemical and biophysical research communications.

[30]  D. Tyler Role of superoxide radicals in the lipid peroxidation of intracellular membranes , 1975, FEBS letters.

[31]  M. Hoffman,et al.  Addition of superoxide radical anion to cobalt(II) macrocyclic complexes in aqueous solution , 1977 .

[32]  I. Fridovich Quantitative aspects of the production of superoxide anion radical by milk xanthine oxidase. , 1970, The Journal of biological chemistry.

[33]  W. Paschen,et al.  Singlet oxygen and superoxide dismutase (cuprein). , 1975, Biochemical and biophysical research communications.

[34]  K. Gollnick,et al.  Zur photosensibilisierten Autoxydation der Steroide. Darstellung von Steroid‐Hydroperoxyden Mittels Phototoxischer Photosensibilisatoren , 1957 .

[35]  P. O'Brien,et al.  The possible involvement of singlet oxygen in prostaglandin biosynthesis. , 1976, Biochemical and biophysical research communications.

[36]  G. Rotilio,et al.  The binding of copper ions to copper-free bovine superoxide dismutase. Properties of the protein recombined with increasing amounts of copper ions. , 1977, The Biochemical journal.

[37]  S. Aust,et al.  The role of superoxide and singlet oxygen in lipid peroxidation promoted by xanthine oxidase. , 1973, Biochemical and biophysical research communications.

[38]  H. Taube Mechanisms of Oxidation with Oxygen , 1965, The Journal of general physiology.

[39]  R. M. Arneson,et al.  Substrate-induced chemiluminescence of xanthine oxidase and aldehyde oxidase. , 1970, Archives of biochemistry and biophysics.

[40]  F. Bischoff Carcinogenic effects of steroids. , 1969, Advances in lipid research.

[41]  I. Fridovich,et al.  Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). , 1969, The Journal of biological chemistry.

[42]  A. Michelson Studies in bioluminescence. 10. Chemical models of enzymic oxidations. , 1973, Biochimie.

[43]  K. Asada,et al.  Reactivity of Thiols with Superoxide Radicals , 1976 .

[44]  Ahsan Khan Singlet molecular oxygen. A new kind of oxygen , 1976 .

[45]  S. H. Ong,et al.  The chemistry of free radicals , 1974 .

[46]  D. Menzel CHAPTER 6 – The Role of Free Radicals in the Toxicity of Air Pollutants (Nitrogen Oxides and Ozone) , 1976 .

[47]  I. Fridovich,et al.  The role of superoxide anion in the autoxidation of epinephrine and a simple assay for superoxide dismutase. , 1972, The Journal of biological chemistry.

[48]  L. Smith,et al.  Sterol metabolism. XXIV. On the unlikely participation of singlet molecular oxygen in several enzyme oxygenations. , 1973, Journal of the American Chemical Society.

[49]  S. Yang,et al.  Photochemical production of ethylene from methionine and its analogues in the presence of flavin mononucleotide. , 1967, The Journal of biological chemistry.

[50]  L. Flohé,et al.  Inhibition of lipid peroxidation in isolated inner membrane of rat liver mitochondria by superoxide dismutase , 1973, FEBS letters.

[51]  I. Yamazaki,et al.  One-electron transfer reactions in biochemical systems. 8. Kinetic study of superoxide dismutase. , 1973, Biochimica et biophysica acta.

[52]  Ahsan Khan Singlet Molecular Oxygen from Superoxide Anion and Sensitized Fluorescence of Organic Molecules , 1970, Science.

[53]  B. Bielski,et al.  Deuterium isotope effect on the decay kinetics of perhydroxyl radical , 1971 .

[54]  B. Bielski,et al.  A study of the superoxide radical chemistry by stopped-flow radiolysis and radiation induced oxygen consumption , 1977 .

[55]  K. Rajagopalan,et al.  The role of superoxide anion generation in phagocytic bactericidal activity. Studies with normal and chronic granulomatous disease leukocytes. , 1975, The Journal of clinical investigation.

[56]  H. Wasserman RECENT REACTIONS OF SINGLET OXYGEN WITH HETEROCYCLIC AND AROMATIC SUBSTRATES * , 1970 .

[57]  I. Fridovich,et al.  The utility of superoxide dismutase in studying free radical reactions. II. The mechanism of the mediation of cytochrome c reduction by a variety of electron carriers. , 1970, The Journal of biological chemistry.

[58]  D. Menzel,et al.  Heinz bodies formed in erythrocytes by fatty acid ozonides and ozone. , 1975, Archives of environmental health.

[59]  Y. Lion,et al.  New method of detecting singlet oxygen production , 1976, Nature.

[60]  P. Ke,et al.  Bunsen coefficient for oxygen in marine oils at various temperatures determined by an exponential dilution method with a polarographic oxygen electrode , 1973 .

[61]  S. Matsugo,et al.  Photoinduced reactions. 97. Polar peroxidic intermediates in low temperature photooxygenation of N-methylindoles , 1977 .

[62]  K. Wong,et al.  Controlled cleavage of phage R17 RNA within the virion by treatment with ascorbate and copper (II). , 1974, Canadian journal of biochemistry.

[63]  M. Cerqueira,et al.  Evidence that the superoxide-generating system of human leukocytes is associated with the cell surface. , 1977, The Journal of clinical investigation.

[64]  E. Hayon,et al.  One-electron Redox reactions of water-soluble vitamins. 4. Thiamin (vitamin B1), biotin, and pantothenic acid. , 1977, Journal of Organic Chemistry.

[65]  I. Fridovich,et al.  The mechanism of the activity-dependent luminescence of xanthine oxidase. , 1976, Archives of biochemistry and biophysics.

[66]  G. Czapski RADIATION CHEMISTRY OF OXYGENATED AQUEOUS SOLUTIONS. , 1971 .

[67]  E. W. Kellogg,et al.  Superoxide, hydrogen peroxide, and singlet oxygen in lipid peroxidation by a xanthine oxidase system. , 1975, The Journal of biological chemistry.

[68]  H. Chan Photo-sensitized oxidation of unsaturated fatty acid methyl esters. The identification of different pathways , 1977 .

[69]  J. McCord Free Radicals and Inflammation: Protection of Synovial Fluid by Superoxide Dismutase , 1974, Science.

[70]  N. Olson,et al.  Spectrophotometric Determination of Hydrogen Peroxide in Milk , 1967 .

[71]  V. Marshall,et al.  Antibacterial Activity of the Lactoperoxidase System in Milk Against Pseudomonads and Other Gram-Negative Bacteria , 1975, Applied microbiology.

[72]  H. Forman,et al.  Role of superoxide radical in mitochondrial dehydrogenase reactions. , 1974, Biochemical and biophysical research communications.

[73]  T. Kimura,et al.  Singlet molecular oxygen in biological systems: non-quenching of singlet oxygen-mediated chemiluminescence by superoxide dismutase. , 1974, Biochemical and biophysical research communications.

[74]  D. Roos Oxidative killing of microorganisms by phagocytic cells , 1977 .

[75]  P. McCay,et al.  Singlet oxygen production associated with enzyme-catalyzed lipid peroxidation in liver microsomes. , 1975, The Journal of biological chemistry.

[76]  E. Land,et al.  One-electron reactions in biochemical systems as studied by pulse radiolysis. IV. Oxidation of dihydronicotinamide-adenine dinucleotide. , 1971, Biochimica et biophysica acta.

[77]  B. Chance,et al.  The role of H 2 O 2 generation in perfused rat liver and the reaction of catalase compound I and hydrogen donors. , 1973, Archives of biochemistry and biophysics.

[78]  G. Grams,et al.  Dye-sensitized photooxidation of tocopherols. Correlation between singlet oxygen reactivity and vitamin E activity. , 1972, Biochemistry.

[79]  L. Weil ON THE MECHANISM OF THE PHOTO-OXIDATION OF AMINO ACIDS SENSITIZED BY METHYLENE BLUE. , 1965, Archives of biochemistry and biophysics.

[80]  P. McCay,et al.  Evidence that peroxidation of lysosomal membranes is initiated by hydroxyl free radicals produced during flavin enzyme activity. , 1973, The Journal of biological chemistry.

[81]  R. Goldstein,et al.  Effects of the generation of superoxide anion on permeability of liposomes. , 1977, Biochemical and biophysical research communications.

[82]  D. Meisel,et al.  The one-electron transfer redox potentials of free radicals. I. The oxygen/superoxide system. , 1976, Biochimica et biophysica acta.

[83]  Robert B. Wilson,et al.  Lipid Peroxidation and atherosclerosis , 1976 .

[84]  M. Rodgers,et al.  THE PHOTOSENSITIZED FORMATION AND REACTION OF SINGLET OXYGEN, O2*(1Δ), IN AQUEOUS MICELLAR SYSTEMS , 1976 .

[85]  D. Frost,et al.  Participation of singlet oxygen in photosensitized oxidation of 1,4-dienoic systems and photooxidation of soybean oil , 1973, Journal of the American Oil Chemists' Society.

[86]  K. Gollnick Chemical Aspects of Photodynamic Action in the Presence of Molecular Oxygen1 , 1975 .

[87]  I. Fridovich,et al.  The interaction of bovine erythrocyte superoxide dismutase with hydrogen peroxide: chemiluminescence and peroxidation. , 1975, Biochemistry.

[88]  G G Guilbault,et al.  Homovanillic acid as a fluorometric substrate for oxidative enzymes. Analytical applications of the peroxidase, glucose oxidase, and xanthine oxidase systems. , 1968, Analytical chemistry.

[89]  I. Fridovich,et al.  The univalent reduction of oxygen by reduced flavins and quinones. , 1972, The Journal of biological chemistry.

[90]  G. A. Hamilton 10 – CHEMICAL MODELS AND MECHANISMS FOR OXYGENASES , 1974 .

[91]  L. Weil,et al.  Photooxidation of amino acids in the presence of methylene blue. , 1951, Archives of biochemistry and biophysics.

[92]  W. C. Danen,et al.  The remarkable nucleophilicity of superoxide anion radical. rate constants for reaction of superoxide ion with aliphatic bromides. , 1977 .

[93]  H. Wasserman,et al.  Reaction of benzo[2.2]paracyclophane with singlet oxygen , 1972 .

[94]  A. Lehninger,et al.  Purification and enzymatic identity of mitochondrial contraction-factors I and II. , 1962, Proceedings of the National Academy of Sciences of the United States of America.

[95]  I. Fridovich,et al.  Electrolytic Univalent Reduction of Oxygen in Aqueous Solution Demonstrated with Superoxide Dismutase , 1972, Science.

[96]  William H Munday Report on Hydrogen Peroxide in Milk , 1957 .

[97]  N. A. Khan Cyclo‐Addition Mechanism in Hydroperoxidation Step of Oxygenation in Linoleate System by Singlet Molecular Oxygen , 1971 .

[98]  J. Fee,et al.  Stopped flow spectrophotometric observation of superoxide dismutation in aqueous solution , 1976, FEBS letters.

[99]  M. Nishikimi,et al.  Oxidation of ascorbic acid with superoxide anion generated by the xanthine-xanthine oxidase system. , 1975, Biochemical and biophysical research communications.

[100]  R. Miller,et al.  The oxidation of tiron by superoxide anion. Kinetics of the reaction in aqueous solution in chloroplasts. , 1975, Biochimica et biophysica acta.

[101]  L. W. Aurand,et al.  SUPEROXIDE AND SINGLET OXYGEN IN MILK LIPID PEROXIDATION , 1977 .

[102]  I. Fridovich,et al.  A direct demonstration of the catalytic action of superoxide dismutase through the use of pulse radiolysis. , 1972, The Journal of biological chemistry.

[103]  E. Keinan,et al.  DRY OZONATION OF AMINES. CONVERSION OF PRIMARY AMINES TO NITRO COMPOUNDS , 1977 .

[104]  Z. D. Roundy Treatment of Milk for Cheese with Hydrogen Peroxide , 1958 .

[105]  S. Gilliland Enzymatic Determination of Residual Hydrogen Peroxide in Milk , 1969 .

[106]  I. Fridovich,et al.  Superoxide dismutase: improved assays and an assay applicable to acrylamide gels. , 1971, Analytical biochemistry.

[107]  T. Kimura,et al.  Reactivity of singlet molecular oxygen with cholesterol in a phospholipid membrane matrix. A model for oxidative damage of membranes. , 1977, Biochemical and biophysical research communications.

[108]  F. S. Brown,et al.  Chloroperoxidase. II. Utilization of halogen anions. , 1966, The Journal of biological chemistry.

[109]  M. Tomita,et al.  Sensitized photooxidation of histidine and its derivatives. Products and mechanism of the reaction. , 1969, Biochemistry.

[110]  J. Rabani,et al.  Acid dissociation constant and decay kinetics of the perhydroxyl radical , 1970 .

[111]  B. Bielski,et al.  Study of the superoxide radical chemistry by stopped-flow radiolysis and radiation induced oxygen consumption. [Electron beams] , 1977 .

[112]  J. Koropatnick,et al.  Mutagaenic action of ascorbic acid , 1976, Nature.

[113]  W. Koppenol Reactions involving singlet oxygen and the superoxide anion , 1976, Nature.

[114]  G. Renger,et al.  Further evidence for dissipative energy migration via triplet states in photosynthesis. The protective mechanism of carotenoids in Rhodopseudomonas spheroides chromatophores. , 1977, Biochimica et biophysica acta.

[115]  G. Cilento,et al.  Singlet oxygen generation by the lipoxidase system. , 1974, Biochemical and biophysical research communications.

[116]  N. Bellanca,et al.  The properties and performance of poly AO™-79; A nonabsorbable, polymeric antioxidant intended for use in foods , 1977, Journal of the American Oil Chemists' Society.

[117]  D. Ballou,et al.  Direct demonstration of superoxide anion production during the oxidation of reduced flavin and of its catalytic decomposition by erythrocuprein. , 1969, Biochemical and biophysical research communications.

[118]  Steele Rh,et al.  Microsomal (muS) chemiluminescence (CL) induced by NADPH and its relation to aryl-hydroxylations. , 1972 .

[119]  B. Halliwell An attempt to demonstrate a reaction between superoxide and hydrogen peroxide , 1976, FEBS letters.

[120]  M. J. Black,et al.  Spectrofluorometric analysis of hydrogen peroxide. , 1974, Analytical biochemistry.

[121]  M. Nishimura,et al.  Formation of singlet molecular oxygen in illuminated chloroplasts. Effects on photoinactivation and lipid peroxidation , 1975 .

[122]  A. Bard,et al.  THE PRODUCTION OF SINGLET OXYGEN IN ELECTROGENERATED RADICAL ION ELECTRON TRANSFER REACTIONS , 1973 .

[123]  D. J. Porter,et al.  Concerning the formation of singlet O2 during the decomposition of H2O2 catalase , 1974 .

[124]  A. O. Allen,et al.  Mechanism of the disproportionation of superoxide radicals , 1977 .

[125]  K. Asada,et al.  Initiation of aerobic oxidation of sulfite by illuminated spinach chloroplasts. , 1973, European journal of biochemistry.

[126]  S. Sligar,et al.  Superoxide anion production by the autoxidation of cytochrome P450cam. , 1974, Biochemical and biophysical research communications.

[127]  M. J. Pallansch,et al.  Effect of Filtering Ozone-Polluted Dryer Air Through Activated Charcoal on the Flavor of Foam Spray-Dried Whole Milk , 1969 .

[128]  A. M. Michelson,et al.  Biological protection by superoxide dismutase. , 1973, Biochemical and biophysical research communications.

[129]  I. Fridovich,et al.  The generation of superoxide radical during the autoxidation of hemoglobin. , 1971, The Journal of biological chemistry.

[130]  H P Misra,et al.  Generation of superoxide free radical during the autoxidation of thiols. , 1974, The Journal of biological chemistry.

[131]  M. Nakano,et al.  Reactivities of diphenylfuran (a singlet oxygen trap) with singlet oxygen and hydroxyl radical in aqueous systems. , 1977, Biochemical and biophysical research communications.

[132]  M. B. Floyd,et al.  The reactions of heterocyclic systems with singlet oxygen. Photosensitized oxygenation of imidazoles , 1968 .

[133]  I. Rosenthal RECENT DEVELOPMENTS IN SINGLET MOLECULAR OXYGEN CHEMISTRY , 1976, Photochemistry and photobiology.

[134]  J. Piatt,et al.  Peroxidaze Catalyzed singlet oxygen formation from hydrogen peroxide , 1977, FEBS letters.

[135]  Fritz Haber,et al.  The catalytic decomposition of hydrogen peroxide by iron salts , 1934 .

[136]  I. Fridovich CHAPTER 6 – Oxygen Radicals, Hydrogen Peroxide, and Oxygen Toxicity , 1976 .

[137]  D. Kearns,et al.  Physical and chemical properties of singlet molecular oxygen , 1971 .

[138]  R. Allen Halide dependence of the myeloperoxidase-mediated antimicrobial system of the polymorphonuclear leukocyte in the phenomenon of electronic excitation. , 1975, Biochemical and biophysical research communications.

[139]  R. Selman,et al.  Effect of pollution of air with ozone on flavor of spray-dried milks. , 1969, Journal of dairy science.

[140]  G. Cohen,et al.  6-Hydroxydopamine: Evidence for Superoxide Radical as an Oxidative Intermediate , 1973, Science.

[141]  P. McCay,et al.  Evidence for superoxide-dependent reduction of Fe3+ and its role in enzyme-generated hydroxyl radical formation. , 1976, Chemico-biological interactions.

[142]  P. Knowles,et al.  Electron-spin-resonance evidence for enzymic reduction of oxygen to a free radical, the superoxide ion. , 1969, The Biochemical journal.

[143]  A. Agrò,et al.  Erythrocuprein and singlet oxygen , 1972, FEBS letters.

[144]  F. J. Simpson,et al.  Degradation of rutin by Aspergillus flavus. Studies with oxygen 18 on the action of a dioxygenase on quercetin. , 1970, The Journal of biological chemistry.

[145]  J. Bland Biochemical effects of excited state molecular oxygen , 1976 .

[146]  T. Kimura,et al.  Cytochrome c enhancement of singlet molecular oxygen production by the NADPH-dependent adrenodoxin reductase-adrenodoxin system: the role of singlet oxygen in damaging adrenal mitochondrial membranes. , 1973, Biochemical and biophysical research communications.

[147]  W. Caughey,et al.  The mechanisms of hemoglobin autoxidation. Evidence for proton-assisted nucleophilic displacement of superoxide by anions. , 1974, Biochemical and biophysical research communications.

[148]  B. Shakhashiri,et al.  Singlet Oxygen in Aqueous Solution: A Lecture Demonstration. , 1976 .