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1991 Fiscal Year Final Research Report Summary

Synthesis of New Vitamin E Derivatives and Mechanism of the Protection of Oxygen Toxicity in Biological System.

Research Project

Project/Area Number 02640396
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionEhime Univesity

Principal Investigator

MUKAI Kazuo  Ehime University, Faculty of Science, Professor, 理学部, 教授 (70036193)

Project Period (FY) 1990 – 1991
KeywordsAntioxidant / Vitamin E / Active Oxygen / Lipid Peroxidation / Reaction Rates / Singlet Oxygen / Stopped-Flow / Ubiquinol
Research Abstract

About 30 kinds of new tocopherol derivatives have been synthesized, and the rates of scavenging of substituted phenoxyl radical (PhO^<. >), k_2 and quenching of singlet oxygen ( ^1O_2), k_Q, by these tocopherols have been measured spectrophotometrically in ethanol. Both the log of the rate constants, k_2 and k_Q, were found to correlate with their peak oxidation potential, E_p. The quenching rates, k_Q, were found to be related linearly to the rates k_1 and k_2 of scavenging of peroxyl (LOO^<. >) (reported by Burton et al.) and phenoxyl (PhO^<. >) radicals by these tocopherols, respectively. Vitamin K_1-and K_3- hydroquinone and some estrogens were found to be several times more active than -tocopherol, respectively, which has the highest antioxidant activity among natural tocopherols Further, the second-order rate constants, k_<-1>, k_3, k_4, and k_6 for the reaction of vitamin E radical with i) lipid hydroperoxides (LOOH), ii) vitamin C, iii) ubiquinol, and iv) unsaturated fatty acid esters (LH), respectively, in solution have been measured. By comparing these rate constants, the mechanism of antioxidant and prooxidant actions of tocopherols in biomembranes and edible oils has been discussed.

  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] K.Mukai: "Stopped-Flow Kinetic Study of the Regeneration Reaction of Tocopheroxyl Radical by Reduced Ubiquinone-10 in Solution." Biochim.Biophys.Acta. 1035. 77-82 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Mukai: "Stopped-Flow Investigation of Antioxidant Activity of Estrogens in Solution." Biochim.Biophys.Acta. 1035. 348-352 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Nagaoka: "Kinetic and ab Initio Study of the Prooxidant Effect of Vitamin E.Hydrogen Abstraction from Fatty Acid Esters and Egg Yolk Lecithin." J.Am.Chem.Soc.112. 8921-8924 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Mukai: "Stopped-Flow Investigation of the Reaction of Vitamin C with Tochopheroxyl Radical in Aqueous Triton X-100 Micelle Solutions." J.Biol.Chem.266. 274-278 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Mukai: "Structure-Activity Relationship in the Quenching Reaction of Singlet Oxygen by Tocopherol(Vitamin E)Derivatives and Related Phenols." J.Org.Chem.56. 4188-4192 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Fukuzawa: "Peroxide-Dependent and -Independent Lipid Peroxidations Catalyzed by Chelated Iron." Arch.Biochem.Biophys.290. 489-496 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Mukai: "Vitamin E:Biochemistry and Clinical Applications" Marcel Dekker Inc., 23 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Mukai: "Oxidative Damage and Repair" Pergamon Press Inc., 5 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K. Mukai: "Stopped-Flow Kinetic Study of the Regeneration Reaction of Tocopheroxyl Radical by Reduced Ubiquinone-10 in Solution" Biochem. Biophys. Acta. 1035. 77-82 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Mukai: "Stopped-Flow Investigation of Antioxidant Activity of Estrogens in Solution." Biochem. Biophys. Acta. 1035. 348-352 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Nagaoka: "Kinetic and ab Initio Study of the Prooxidant Effect of Vitamin E. Hydrogen Abstraction from Fatty Acid Esters and Egg Yolk Lecithin." J. Am. Chem. Soc.112. 8921-8924 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Mukai: "Stopped-Flow Investigation of the Reaction of Vitamin C with Tocopheroxyl Radical in Aqueous Triton X-100 Micelle Solutions." J. Biol. Chem.266. 274-278 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Mukai: "Strucutue-Activity Relationship in the Quenching Reaction of Singlet Oxygen by Tocopherol (Vitamin E) Derivatives and Related Phenols." J. Org. Chem.56. 4188-4192 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Fukuzawa: "Peroxide-Dependent and -Independent Lipid Peroxidations Catalyzed by Chelated Iron." Arch. Biochem. Biophys.290. 489-496 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Mukai: Marcel Dekker Inc.Vitami E : Biochemistry and Clinical Applications, 23 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Mukai: Pergamon Press Inc.Oxidative Damage and Repair, 5 (1992)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-03-16  

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