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Studies of Synthetic Catechin Analogues Useful for Antioxidant Therapy

Research Project

Project/Area Number 14572105
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 医薬分子機能学
Research InstitutionNational Institute of Health Sciences

Principal Investigator

FUKUHARA Kiyoshi  National Institute of Health Sciences, Division of Organic Chemistry, Section Chief, 有機化学部, 室長 (70189968)

Co-Investigator(Kenkyū-buntansha) HAKAMATA Wataru  National Institute of Health Sciences, Division of Organic Chemistry, 研究員 (10333337)
TANNO Masayuki  National Institute of Health Sciences, Division of Organic Chemistry, 主任研究官 (60171914)
Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsAntioxidant / Reactive Oxygen Species / Catechin / Polyphenol / Flavonoid / Cancer
Research Abstract

The protective role of antioxidants against free-radical associated diseases has been widely studied and this has prompted the development of new types of antioxidants. A planar catechin analogue (1H_2), in which catechol and chroman moieties in catechin were constrained to be planar, was synthesized via oxa-Pictet Spengler reaction using catechin and aceton with BF_3.Et_2O. The radical-scavenging activities of 1H_2 were examined using galvinoxyl radical (G^・), a stable oxygen-centered radical, showing that the hydrogen transfer reaction from 1H_2 to G^・ is 5-fold faster than that of hydrogen transfer from the native catechin to G^・. The kinetics of hydrogen transfer from catechins to cumylperoxyl radical was also examined in propionitrile (EtCN) at low temperature with use of ESR, showing that the rate of hydrogen transfer from P1H_2 is significantly faster than that from catechin. Under basic conditions, the dianion (1^<2->) of 1H_2 reduced molecular oxygen to produce superoxide anion (O_2^<・->). However, the electron transfer rate was slower than that of catechin, suggesting that 1H_2 may be a promising novel antioxidant with reduced pro-oxidant activity. The 1H_2 also showed an enhanced protective effect against the oxidative DNA damage induced by Fenton reaction without the pro-oxidant effect, which is usually observed in the case of the native catechin.
Finally, the planar catechin acalogue showed the strong radical scavenging ability and reduced prooxidant effect responsible for the less-efficient generation of O_2^<・->. The completed inhibition of DNA strand scission is also expected the efficient protection toward oxidative damage of biopolymers caused by the reactive oxygen species. The lipophilic property of 1H_2 is also useful for suppressing free-radical associated event, especially in the cell membrane. Therefore, 1H_2 might be very effective for the prevention and/or treatment of free radical-associated diseases.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (38 results)

All Other

All Publications (38 results)

  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "EPR Study on Stable Magnesium Complexes of the Phenoxyl Radicals Derived from a Vitamin E Model and Its Deuterated Derivatives"Bull.Chem.Soc.Jpn.. In press. (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Matsuoka, K.Fukuhara, et al.: "Correlation of sister chromatid exchange formation through homologouos recombination with ribonucleotide reductase inhibition"Mutation Res.. 547. 101-107 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "A Planar Catechin Analogue Having a More Negative Oxidation Potential than (+)-Catechin as an Electron-Transfer Antioxidant against a Peroxyl Radical"Chem.Res.Toxicol.. 17. 26-31 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "Kinetic Study on the Electron-Transfer Oxidation of the Phenolate Anion of a Vitamin E Model by Molecular Oxygen Generating Superoxide Anion in an Aprotic Medium"Org.Biomol.Chem.. 1. 1452-1454 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Saeki, K.Fukuhara, et al.: "Activation of the Human Ah Receptor by Aza-Polycyclic Aromatic Hydrocarbons and Their Halogenated Derivatives"Biol.& Pharm.Bull.. 26. 448-452 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukuhara, et al.: "A Planar Catechin Analogue as a Promising Antioxidant with Reduced Prooxidant Activity"Chem.Res.Toxicol.. 16. 81-86 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Tokiwa, K.Fukuhara: "Structural activity relationship between Salmonella-mutagenicity and nitro-orientation of nitroazaphenanthrenes"Chem.Biochem.Interactions. 146. 19-25 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi, K.Fukuhara: "Efficient radical scavenging ability of artepillin C, a major component of Brazilian propolis, and the mechanism"Org.Biomol.Chem.. 1. 1452-1454 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Matsuoka, K.Fukuhara, et al.: "The 4' hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol"Mutation Res.. 521. 29-35 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "Effects of metal ions distinguishing between one-step hydrogen-n and electron-transfer mechanisms for the radical-scavenging reaction of (+)-catechin"J.Phys.Chem.A. 106. 11123-11126 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "Effects of magnesium ion on kinetic stability and spin distribution of phenoxyl radical derived from a vitamin E analogues"J.Chem.Soc.Perkin 2. 1520-1524 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukuhara, I.Nakanishi, et al.: "Enhanced radical scavenging activity of a planar catechin analogue"J.Am.Chem.Soc.. 124. 5952-5953 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukuhara, Y.Naito.et al.: "Generation of oxygen radicals and DNA-cleaving ability in quinone/NADH system"Magnetic Resonance in Medicine. 13. 139-142 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi: "EPR Study on Stable Magnesium Complexes of the Phenoxyl Radicals Derived from a Vitamin E Model and Its Deuterated Derivatives"Bull.Chem.Soc. Jpn. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Matsuoka: "Correlation of sister chromatid exchange formation through homologouos recombination with ribonucleotide reductase inhibition"Mutat.Res.. 547. 101-107 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi: "A Planar Catechin Analogue Having a More Negative Oxidation Potential than (+)-Catechin as an Electron-Transfer Antioxidant against a Peroxyl Radical"Chem.Res.Toxicol.. 17. 26-31 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi: "Kinetic Study on the Electron-Transfer Oxidation of the Phenolate Anion of a Vitamin E Model by Molecular Oxygen Generating Superoxide Anion in an Aprotic Medium"Org.Biomol.Chem.. 1. 1452-1454 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Saeki: "Activation of the Human Ah Receptor by Aza-Polycyclic Aromatic Hydrocarbons and Their Halogenated Derivatives"Biol. & Pharm.Bull.. 26. 448-452 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukuhara: "A Planar Catechin Analogue as a Promising Antioxidant with Reduced Prooxidant Activity"Chem.Res.Toxicol.. 16. 81-86 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Tokiwa: "Structural activity relationship between Salmonella-mutagenicity and nirtro-orientation of nitroazaphenanthrenes"Chem.Biochem. Interactions. 146. 19-25 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi: "Efficient radical scavenging ability of artepillin C, a major component of Brazilian propolis, and the mechanism"Org.Biomol.Chem.. 1. 1452-1454 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Matsuoka: "The 4' hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol"Mutation Res.. 521. 29-35 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanishi: "Effects of metal ions distinguishing between one-step hydrogen-n and electron-transfer mechanisms for the radical-scavenging reaction of (+)-catechin"J.Phys.Chem.A.. 106. 11123-11126 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Nakanish: "Effects of magnesium ion on kinetic stability and spin distribution of phenoxyl radical derived from a vitamin E analogues"J.Chem.Soc. Perkin. 2. 1520-1524 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukuhara: "Enhanced radical scavenging activity of a planar catechin analogue"J.Am.Chem.Soc.. 124. 5952-5953 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukuhara: "Generation of oxygen radicals and DNA-cleaving ability in quinone/NADH system"Magnetic Resonance in Medicine. 13. 139-142 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Matsuoka, K.Fukuhara, et al.: "Correlation of sister chromatid exchange formation through homologouos recombination with ribonucleotide reductase inhibition"Mutation Res.. 547. 101-107 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] I Nakanishi, K.Fukuhara, et al.: "A Planar Catechin Analogue Having a More Negative Oxidation Potential than(+)-Catechin as an Electron-Transfer Antioxidant against a Peroxyl Radical"Chem.Res.Toxicol.. 17. 26-31 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] I Nakanishi, K.Fukuhara, et al.: "Kinetic Study on the Electron-Transfer Oxidation of the Phenolate Anion of a Vitamin E Model by Molecular Oxygen Generating Superoxide Anion in an Aprotic Medium"Org.Biomol.Chem.. 1. 1452-1454 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Saeki, K.Fukuhara, et al.: "Activation of the Human Ah Receptor by Aza-Polycyclic Aromatic Hydrocarbons and Their Halogenated Derivatives"Biol.& Pharm.Bull. 26. 448-452 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Fukuhara, et al.: "A Planar Catechin Analogue as a Promising Antioxidant with Reduced Prooxidant Activity"Chem.Res.Toxicol.. 16. 81-86 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Tokiwa, K.Fukuhara: "Structural activity relationship between Salmonella-mutagenicity and nirtro-orientation of nitroazaphenanthrenes"Chem.Biochem.Interactions. 146. 19-25 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Saeki, K.Fukuhara, et al.: "Activation of the human Ah receptor by aza-polycyclic aromatic hydrocarbon and their halogenated derivatives"Biological & Pharmaceutical Bulletin. (In press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Fukuhara, I.Nakanishi, et al.: "A planar catechin analogue as a promising antioxidant with reduced prooxidant activity"Chem. Res. Toxicol.. 16. 81-86 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] A.Matsuoka, K.Fukuhara, et al.: "The 4' hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol"Mutation Res.. 521. 29-35 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "Effects of metal ions distinguishing between one-step hydrogen-n and electron-transfer mechanisms for the radical-scavenging reaction of (+)-catechin"J. Phys. Chem. A. 106. 11123-11126 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] I.Nakanishi, K.Fukuhara, et al.: "Effects of magnesium ion on kinetic stability and spin distribution of phenoxyl radical derived from a vitamin E analogues"J. Chem. Soc. Perkin 2. 1520-1524 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Fukuhara, I.Nakanishi, et al.: "Enhanced radical scavenging activity of a planar catechin analogue"J. Am. Chem. Soc.. 124. 5952-5953 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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