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The Specificity of Lipoxygenase-Catalyzed Lipid Peroxidation and the Effects of Radical- Scavenging Antioxidants

  • N. Noguchi , H. Yamashita , J. Hamahara , A. Nakamura , H. Kühn and E. Niki
Published/Copyright: June 1, 2005
Biological Chemistry
From the journal Volume 383 Issue 3-4

Abstract

The oxidation of low density lipoprotein (LDL) by lipoxygenase has been implicated in the pathogenesis of atherosclerosis. It has been known that lipoxygenasemediated lipid peroxidation proceeds in general via regio, stereo and enantiospecific mechanisms, but that it is sometimes accompanied by a share of random hydroperoxides as side reaction products. In this study we investigated the oxidation of various substrates (linoleic acid, methyl linoleate, phosphatidylcholine, isolated LDL, and human plasma) by the arachidonate 15-lipoxygenases from rabbit reticulocytes and soybeans aiming at elucidating the effects of substrate, lipoxygenase and reaction milieu on the contribution and mechanism of random oxidation and also the effect of antioxidant. The specific character of the rabbit 15-lipoxygenase reaction was confirmed under all conditions employed here. However, the specificity by soybean lipoxygenase was markedly dependent on the conditions. When phosphatidylcholine liposomes and LDL were oxygenated by soybean lipoxygenase, the product pattern was found to be exclusively regio, stereo, and enantiorandom. When free linoleic acid was incorporated into PC liposomes and oxidized by soybean lipoxygenase, the free acid was specifically oxygenated, whereas esterified linoleate gave random oxidation products exclusively. Radicalscavenging antioxidants such as αtocopherol, ascorbic acid and 2-carboxy-2,5,7,8-tetramethyl-6-chromanol selectively inhibited the random oxidation but did not influence specific product formation. It is assumed that the random reaction products originate from free radical intermediates, which have escaped the active site of the enzyme and thus may be accessible to radical scavengers. These data indicate that the specificity of lipoxygenasecatalyzed lipid oxidation and the inhibitory effects of antioxidants depend on the physicochemical state of the substrate and type of lipoxygenase and that they may change completely depending on the conditions.

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Published Online: 2005-06-01
Published in Print: 2002-04-12

Copyright © 2002 by Walter de Gruyter GmbH & Co. KG

Articles in the same Issue

  1. Highlight: Oxidative Stress
  2. Highlight: Oxidative Stress
  3. Peroxiredoxins
  4. 15-Lipoxygenase-1: A Prooxidant Enzyme
  5. Reactive Sulfur Species: An Emerging Concept in Oxidative Stress
  6. The Pathobiochemistry of Nitrogen Dioxide
  7. Nitric Oxide and Peroxynitrite Interactions with Mitochondria
  8. Nitric Oxide and Cell Signaling Pathways in Mitochondrial-Dependent Apoptosis
  9. Fatty Acid Oxidation and Signaling in Apoptosis
  10. Oxidant-Induced Signaling: Effects of Peroxynitrite and Singlet Oxygen
  11. The 80th Anniversary of Vitamin E: Beyond Its Antioxidant Properties
  12. Role of Endogenous Oxidative DNA Damage in Carcinogenesis: What Can We Learn from Repair-Deficient Mice?
  13. Mammalian Cell Injury Induced by Hypothermia the Emerging Role for Reactive Oxygen Species
  14. The Chelatable Iron Pool in Living Cells: A Methodically Defined Quantity
  15. Dietary Flavonoids as Potential Neuroprotectants
  16. Oxidative Nerve Cell Death in Alzheimers Disease and Stroke: Antioxidants as Neuroprotective Compounds
  17. A2E and Blue Light in the Retina: The Paradigm of Age-Related Macular Degeneration
  18. Interactions of Nitric Oxide and Peroxynitrite with Low-Density Lipoprotein
  19. Non-Antioxidant Properties of Carotenoids
  20. Proteolytic Response to Oxidative Stress in Mammalian Cells
  21. Neurospora crassa Catalases, Singlet Oxygen and Cell Differentiation
  22. The Cellular Hydration State: A Critical Determinant for Cell Death and Survival
  23. Redox Regulation of Stress Signals: Possible Roles of Dendritic Stellate TRX Producer Cells (DST Cell Types)
  24. Oxidative Stress, Spermatogenesis and Fertility
  25. Postprandial Oxidative Stress
  26. [18O]-Labeled Singlet Oxygen as a Tool for Mechanistic Studies of 8-Oxo-7,8-Dihydroguanine Oxidative Damage: Detection of Spiroiminodihydantoin, Imidazolone and Oxazolone Derivatives
  27. The Specificity of Lipoxygenase-Catalyzed Lipid Peroxidation and the Effects of Radical- Scavenging Antioxidants
  28. Human Neutrophils Oxidize Low-Density Lipoprotein by a Hypochlorous Acid- Dependent Mechanism: The Role of Vitamin C
  29. Perturbation of Lipid Metabolism by Linoleic Acid Hydroperoxide in CaCo-2 Cells
  30. Irreversible Thiol Oxidation in Carbonic Anhydrase III: Protection by S-Glutathiolation and Detection in Aging Rats
  31. Green Tea Extract Protects against Early Alcohol-Induced Liver Injury in Rats
  32. Comparing β-Carotene, Vitamin E and Nitric Oxide as Membrane Antioxidants
  33. Induction of Thioredoxin Reductase Gene Expression by Peroxynitrite in Human Umbilical Vein Endothelial Cells
  34. Activation of c-Jun N-Terminal Kinase and Apoptosis in Endothelial Cells Mediated by Endogenous Generation of Hydrogen Peroxide
  35. Detection of Poly(ADP-Ribose) by Immunocytochemistry: A Sensitive New Method for the Early Identification of UVB- and H2O2-Induced Apoptosis in Keratinocytes
  36. Efficacy of HOCl Scavenging by Sulfur- Containing Compounds: Antioxidant Activity of Glutathione Disulfide?
  37. Cysteine Supplementation Prevents Unweighting-Induced Ubiquitination in Association with Redox Regulation in Rat Skeletal Muscle
https://doi.org/10.1515/BC.2002.064

Articles in the same Issue

  1. Highlight: Oxidative Stress
  2. Highlight: Oxidative Stress
  3. Peroxiredoxins
  4. 15-Lipoxygenase-1: A Prooxidant Enzyme
  5. Reactive Sulfur Species: An Emerging Concept in Oxidative Stress
  6. The Pathobiochemistry of Nitrogen Dioxide
  7. Nitric Oxide and Peroxynitrite Interactions with Mitochondria
  8. Nitric Oxide and Cell Signaling Pathways in Mitochondrial-Dependent Apoptosis
  9. Fatty Acid Oxidation and Signaling in Apoptosis
  10. Oxidant-Induced Signaling: Effects of Peroxynitrite and Singlet Oxygen
  11. The 80th Anniversary of Vitamin E: Beyond Its Antioxidant Properties
  12. Role of Endogenous Oxidative DNA Damage in Carcinogenesis: What Can We Learn from Repair-Deficient Mice?
  13. Mammalian Cell Injury Induced by Hypothermia the Emerging Role for Reactive Oxygen Species
  14. The Chelatable Iron Pool in Living Cells: A Methodically Defined Quantity
  15. Dietary Flavonoids as Potential Neuroprotectants
  16. Oxidative Nerve Cell Death in Alzheimers Disease and Stroke: Antioxidants as Neuroprotective Compounds
  17. A2E and Blue Light in the Retina: The Paradigm of Age-Related Macular Degeneration
  18. Interactions of Nitric Oxide and Peroxynitrite with Low-Density Lipoprotein
  19. Non-Antioxidant Properties of Carotenoids
  20. Proteolytic Response to Oxidative Stress in Mammalian Cells
  21. Neurospora crassa Catalases, Singlet Oxygen and Cell Differentiation
  22. The Cellular Hydration State: A Critical Determinant for Cell Death and Survival
  23. Redox Regulation of Stress Signals: Possible Roles of Dendritic Stellate TRX Producer Cells (DST Cell Types)
  24. Oxidative Stress, Spermatogenesis and Fertility
  25. Postprandial Oxidative Stress
  26. [18O]-Labeled Singlet Oxygen as a Tool for Mechanistic Studies of 8-Oxo-7,8-Dihydroguanine Oxidative Damage: Detection of Spiroiminodihydantoin, Imidazolone and Oxazolone Derivatives
  27. The Specificity of Lipoxygenase-Catalyzed Lipid Peroxidation and the Effects of Radical- Scavenging Antioxidants
  28. Human Neutrophils Oxidize Low-Density Lipoprotein by a Hypochlorous Acid- Dependent Mechanism: The Role of Vitamin C
  29. Perturbation of Lipid Metabolism by Linoleic Acid Hydroperoxide in CaCo-2 Cells
  30. Irreversible Thiol Oxidation in Carbonic Anhydrase III: Protection by S-Glutathiolation and Detection in Aging Rats
  31. Green Tea Extract Protects against Early Alcohol-Induced Liver Injury in Rats
  32. Comparing β-Carotene, Vitamin E and Nitric Oxide as Membrane Antioxidants
  33. Induction of Thioredoxin Reductase Gene Expression by Peroxynitrite in Human Umbilical Vein Endothelial Cells
  34. Activation of c-Jun N-Terminal Kinase and Apoptosis in Endothelial Cells Mediated by Endogenous Generation of Hydrogen Peroxide
  35. Detection of Poly(ADP-Ribose) by Immunocytochemistry: A Sensitive New Method for the Early Identification of UVB- and H2O2-Induced Apoptosis in Keratinocytes
  36. Efficacy of HOCl Scavenging by Sulfur- Containing Compounds: Antioxidant Activity of Glutathione Disulfide?
  37. Cysteine Supplementation Prevents Unweighting-Induced Ubiquitination in Association with Redox Regulation in Rat Skeletal Muscle
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