• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

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
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1991: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1990: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsAntioxidant / Vitamin E / Active Oxygen / Lipid Peroxidation / Reaction Rates / Singlet Oxygen / Stopped-Flow / Ubiquinol / ビタミンC / 抗酸化活性 / ユビキノン / エストロゲン / 活性酸素
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.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (32 results)

All Other

All Publications (32 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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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
    • Related Report
      1991 Final Research Report Summary
  • [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)

    • Related Report
      1991 Annual Research Report
  • [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)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Fukuzawa: "Peroxide‐Dependent and‐Independent Lipid peroxidations Catalyzed by Chelated Iron." Arch.Biochem.Biophys.290. 489-496 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] S.Nagaoka: "Mechanism of Antioxidant Reaction of Vitamin E.Charge Transfer and Tenneling Effect in Proton Transfer Reaction." J.Phys.Chem.(1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Y.Kaneko: "Synthesis and Antioxidant Activity of 6‐Hydroxy‐1,3‐Benzodioxine DerivativesーNew Vitamin E Analoguesー" J.Org.Chem.

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Mukai: "Kinetic Study of the Prooxidant Effect of Tocopherol.The Hydrogen Abstraction Reaction from Lipid Hydroperoxides by Tocopheroxyls in Solution." Lipids.

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Mukai: "Vitamin E:Biochemistry and Clinical Applications" Marcel Dekker Inc., 23 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Mukai: "Oxidative Damage and Repair" Pergamon Press Inc., 5 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Mukai: "StoppedーFlow kinetic Study of the Regeneration Reaction of Tocopheroxyl Radical by Reduced Ubiquinoneー10 in Solution." Biochim.Biophys.Acta. 1035. 77-82 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Mukai: "StoppedーFlow Investigation of Antioxidant Activity of Estrogens in Solution." Biochim.Biophys.Acta. 1035. 348-352 (1990)

    • Related Report
      1990 Annual Research Report
  • [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)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Mukai: "StoppedーFlow Investigation of the Reaction of Vitamin C with Tocopheroxyl Radical in Aqueous Triton Xー100 Micelle Solutions.The StructureーActivity Relationship of the Regeneration Reaction of Tocopherol by Vitamin C." J.Biol.Chem.(1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Mukai: "StructureーActivity Relationship in the Quenching Reaction of Singlet Oxygen by Tocopherol (Vitamin E) Derivatives and Related phenols.Finding of Linear Correlation between the Rates of Quenching of Singlet Oxygen and Scavenging of Peroxyl and Phenoxyl Radicals in Solution." J.Org.Chem.

    • Related Report
      1990 Annual Research Report
  • [Publications] 向井 和男: "ビタミンE誘導体の構造と活性" 磁気共鳴と医学. 1. 18-25 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Mukai (分担執筆): "Oxidative Damage and Repair" Pergamon Press Inc., 5 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] K.Mukai (分担執筆): "Vitamin E:Biochemistry and Clinical Applications." Marcel Dekker Inc., 30 (1991)

    • Related Report
      1990 Annual Research Report

URL: 

Published: 1990-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi