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Natural Antioxidants : Their Activities and Action Mechanism

Research Project

Project/Area Number 11694089
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section一般
Research Field 機能・物性・材料
Research InstitutionEhime University

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) OHARA Keish  Ehime University, Faculty of Science, Instructor, 理学部, 助手 (10284390)
NAGAOKA Shin-ichi  Institute for Molecular Science, Associate Professor, 分子科学研究所, 助教授 (30164403)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥4,300,000 (Direct Cost: ¥4,300,000)
Fiscal Year 2000: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1999: ¥2,300,000 (Direct Cost: ¥2,300,000)
KeywordsAntioxidant / Caffeic Acid / Catechin / Radical-Scavenging-Rate / Antioxidant Activity / Stopped- flow Spectrophotometer / Time Resolved ESR / Oxygen Absorption Method / 酸素吸収法 / 天然抗酸化剤 / ラジカルスカベンジャー / ストップフロー
Research Abstract

In the present work, we measured the rate constants of the reaction of peroxyl, tocopheroxyl, and aroxyl free radicals with natural antioxidants, such as catechins, caffeic acids and related compounds in homogeneous and micellar solutions, by using oxygen absorption method, stopped-flow spectrophotometer, and time-resolved ESR method. We have succeeded in obtaining the following interesting results :
l) Detailed kinetic studies have been performed for the reaction of aroxyl (ArO ・) and 5,7-diisopropyltocopheroxyl (Toc ・ ) radicals with catechin, epicatechin, and related antioxidants in homogeneous and micellar solutions. The structure-activity relationship in the scavenging reaction of free radicals by catechin and epicatechin in solution was discussed. It has been found that catechin and epicatechin have high activity in vitamin E regeneration.
2) The antioxidant activity of curcumin (1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) was determined by inhibition of controlled initiation of styrene oxidation. Synthetic nonphenolic curcumins exhibited no antioxidant activity, therefore, curcumin is a classical phenolic chain-breaking antioxidant, donating H atoms from the phenolic groups not the CH_2 group as has been suggested (Jovanovic et al. J.Am. Chem. Soc., 121, 9677 (1999)).
3) Studies of the kinetics of the proton- or hydrogen-transfer reactions concerning vitamin E in solutions and in micellar dispersions by means of stopped-flow and absorption spectroscopy indicated that proton tunneling plays an important role in the antioxidant and regeneration reactions that are advantageous in vivo but not as a part of the harmful prooxidant action.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] K.Ohara: "A CIDEP Study on the Photosensitized Reaction of Maleimide with Xanthone : Addition Effect of Hydrochloric Acid"Bull.Chem.Soc.Jpn.. 73. 37-42 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Nagaoka: "Tunneling Effect in Antioxidant, Prooxidant, and Reqeneration Reaction of Vitamin E"J.Phys.Chem.B. 104. 856-862 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Ohara: "Anomalous Spin Polarization in the Photoreduction of Chromone-2-carboxylic Acid with Alcohol Induced by ....."Chem.Phys.Letters. 317. 619-623 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Effect of Nonmagnetic Impurities on the Spin-Peierls System : p-CyDOV"Physica B. 284-288. 1647-1648 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] L.R.C.Barclay: "On the Antioxidant Mechanism of Curcumin : Classical Methods Are Needed to Determine Antioxidant Mechanism and Activity"Org.Letters. 2. 2841-2843 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Syntheses and Properties of Genuine Organic Magnetic Conductures : (1:1) and (1:2) Salts of Ethyl-pyridinium..."Polyhedron. (in press). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Free Radical Chemistry of Coenzyme Q.Chap.3"Coenzyme Q : Molecular Mechanisms in Health and Disease. Eds.V.E.Kagan and P.J.Quinn (CRC Press LLC). 19 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Free Radical-Scavenging Action of Catechin and Related Compounds in Homogeneous and Micellar Solutions. Chap.20"Phytochemicals and Phytopharmaceuticals. Eds.F.Shahidi and C-T.Ho (AOCS Press). 17 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Ohara: "A CIDEP Study on the Photosensitized Reaction of Maleimide with Xanthone : Addition Effect of Hydrochloric Acid."Bull.Chem.Soc.Jpn.. 73. 37-42 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Nagaoka: "Tunneling Effect in Antioxidant, Prooxidant, and Regeneration Reaction of Vitamin E."J.Phys.Chem.B.. 104. 856-862 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Ohara: "Anomalous Spin Polarization in the Photoreduction of Chromone-2-carboxylic Acid with Alcohol Induced by Hydrochloric Acid."Chem.Phys.Lett.. 317. 619-623 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Effect of Nonmagnetic Impurities on the Spin-Peierls System : p-CyDOV."Physica B. 284-288. 1647-1648 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] L.R.C.Barclay: "On the Antioxidant Mechanism Curcumin : Classical Methods are Needed to Determine Antioxidant Mechanism and Activity."Org.Letters. 2. 2841-2843 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Syntheses and Properties of Genuine Organic Magnetic Conductors : (1 : 1) and (1 : 2) Salts of Ethyl-Pyridinium-Substituted Verdazyl Radicals with TCNQ."Polyhedron. (in press). (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Coenzyme Q : From Molecular Mechanisms to Nutrition and Health, Chap. 3"Free Radical Chemistry of Coenzyme Q, Eds. V.E.Kagan and P.J.Quinn : (CRC PRESS LLC).. 43-61 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Mukai: "Phytochemicals and Phytopharmaceuticals, Chap. 20"Free-Radical-Scavenging Action of Catechin and Related Compounds in Homogeneous and Micellar Solutions, Ed. F.Shahidi and C-T.Ho : (AOCS Press, Champaign (Illinois)).. 221-237 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Ohara: "A CIDEP Study on the Photosensitized Reaction of Maleimide with Xanthone ; Addition Effect of Hydrochloric Acid"Bull.Chem.Soc.Jpn.. 73(1). 37-42 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] S.Nagaoka: "Tunneling Effect in Antioxidant, Prooxidant, and Regeneration Reactions of Vitamin E"J.Phys.Chem.B. 104(4). 856-862 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Ohara: "Anomalous Spin Polarization in the Photoreduction of Chromone-2-carboxylic Acid with Alcohol Induced by....."Chem.Phys.Letters. 317. 619-623 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Mukai: "Effect of Nonmagnetic Impurities on the Spin-Peierls System ; p-CyDOV"Physica B. 284-288. 1647-1648 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] L.Ross C.Barclay: "On the Antioxidant Mechanism of Curcumin ; Classical Methods are Needed to Determine Antioxidant Mechanism..."Org.Letters. 2(18). 2841-2843 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Mukai: "Syntheses and Properties of Genuine Organic Magnetic Conductors ; (1:1) and (1:2) Salts of Ethyl-pyridinium..."Polyhedron. (in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Mukai: "Free Radial Chemistry of Coenzyme Q, Chap.3"Coenzyme Q ; Molecular Mechanisms in Health and Disease Eds.V.E.Kagan and P.J.Quinn (CRC Press LLC). 19 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Mukai: "Free Radical-Scavenging Action of Catechin and Related Compounds in Homogeneous and Micellar Solutions.Chap.20"Phytochemicals and Phytopharmaceuticals.Eds.F.Shahidi and C-T.Ho (AOCS Press). 17 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] S.Nagaoka: "Nodal-Plane Model of the Excited-State Intramolecular Prot on Transfer of 2-(o-Hydroxyaryl)benzazoles."J.Photochem.Photobiol.A;Chemistry. 122. 151-159 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Ohara: "A CIDEP Study on the Photosensitized Reaction of Maleimide with Xanthone;Addition Effect of Hydrochloric・・・"Bull.Chem.Soc.Jpn.. 73. 37-42 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Ohara: "Anomalous Spin Polarization in the Photoreduction of Chromone-2-carboxylic Acid with Alcohol Induced by・・・"Chem.Phys.Letters. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] S.Nagaoka: "Tunneling Effect in Antioxidant,Prooxidant,and Regeneration Reaction of Vitamin E."J.Phys.Chem.B. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Mukai: "Phytochem.and Phytopharm.Chap.20"Ed.F.Shahidi(AOCS Press,Champaign(I11inois)). 17 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Mukai: "Coenzyme Q;From Molecular Mechanisms to Nutrition and Health.Chap.9"Eds.P.Quinn and V.Kagan(CRC PRESS LLC)(in press). (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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