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Synthesis and antioxidant activity of vitamin C analogs and vitamin E analogs

Research Project

Project/Area Number 11672217
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 InstitutionKyoritsu College of Pharmacy

Principal Investigator

MASHINO Tadahiko  Kyoritsu College of Pharmacy, Faculty of Pharmaceutical Sciences, Associate Professor (90165697)

Co-Investigator(Kenkyū-buntansha) ISHIKAWA Satoko  Kyoritsu College of Pharmacy, Faculty of Pharmaceutical Sciences, Research Associate (70223518)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2000: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1999: ¥2,100,000 (Direct Cost: ¥2,100,000)
KeywordsVitamin C / Vitamin E / Ascorbic acid / Tocopherol / Antioxidant / reductic acid / キサンチンオキシダーゼ / 痛風治療薬
Research Abstract

Reactive oxygen species (ROS) and free radicals induce oxidative stress and play the important role in developing and/or progression of human diseases such as cancer. So, antioxidants are expected to be a good lead compounds for medicines. In this study, we developed excellent antioxidants based vitamin C and E.
1. Vitamin E analogs
We designed and synthesized benzo[h]chroman compounds (BC) which had benzene ring fused with vitamin E skelton and examined superoxide and OH radical quenching activity by ESR spin-trapping methods. Both activities were higher than that of trolox, which is vitamin E water-soluble analog.
2. Vitamin C analogs
Reductic acid (RA) which has a 2,3-enediol moiety conjugated with a carbonyl group in a five-membered carbon ring was synthesized. RA inhibited xanthine oxidase activity, while ascorbic acid did not.
RA quenched free radicals and also decreases active oxygen production. RA is thought to be a more potent inhibitor of active oxygen toxicity than ascorbic acid.
Xanthine oxidase produces uric acid, which plays a crucial role in goat. Therefore, xanthine oxidase inhibitor works as a medicine for goat. RA is thought to be a promising inhibitor for oxidative stress and remedy for goat.
Our data showed that BC and RA serves as a new starting structure for the design of pharmacologically effective compounds such as cancer.

Report

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

    (9 results)

All 2000 1999 Other

All Journal Article (2 results) (of which Peer Reviewed: 1 results) Presentation (6 results) Publications (1 results)

  • [Journal Article] Antioxidant activity and xanthine oxidase inhibition activity of reductic acid ; ascorbic acid analog.2000

    • Author(s)
      T.Mashino, et at
    • Journal Title

      Bioorg. Med.Chem.Lett. 10

      Pages: 2783-2785

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Antioxidant activity and xanthine oxidase inhibition activity of reductic acid ; ascorbic acid analog2000

    • Author(s)
      T.Mashino, Y.Takigawa, N.Saito, L.Q.Wong, M.Mochizuki
    • Journal Title

      Bioorg.Med.Chem.Lett. 10

      Pages: 2783-2785

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Presentation] Antioxidant activity and xanthine oxidase inhibition activity of reductic acid ; ascorbic acid skeleton analog.2000

    • Author(s)
      T.Mashino, et al.
    • Organizer
      10th Biennial Meeting of the Society for Free Radical Research Internationl
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2000-10-25
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Presentation] Antioxidant activity and xanthine oxidase inhibition activity of reductic acid ; ascorbic acid skeleton analog2000

    • Author(s)
      T.Mashino, et al.
    • Organizer
      10th Biennial Meeting of the Society for Free Radical Research Internationl
    • Place of Presentation
      Kyoto
    • Year and Date
      2000-10-25
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Presentation] Xanthine oxidase阻害活性を有する抗酸化剤の開発.2000

    • Author(s)
      滝川靖, 増野匡彦, 他
    • Organizer
      第4回日本フリーラジカル学会
    • Place of Presentation
      東京
    • Year and Date
      2000-06-23
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Presentation] キサンチンオキシダーゼ阻害活性を有するアスコルビン酸類縁体の開発.1999

    • Author(s)
      増野匡彦, 他
    • Organizer
      第19回メディシナルケミストリーシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      1999-11-24
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Presentation] Development of Antioxidant with xanthine oxidase inhibition activity

    • Author(s)
      Y.Takigawa, T.Mashino, et al.
    • Organizer
      4th the Society for Free Radical Research Meeting
    • Place of Presentation
      Tokyo
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Presentation] Antioxidant activity and xanthine oxidase inhibition activity of ascorbic acid analog

    • Author(s)
      T.Mashino, et al.
    • Organizer
      19th Medicinal Chemistry Symposium
    • Place of Presentation
      Tokyo
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Mashino et al.: "Antioxidant activity and xanthine oxidase inhibition activity of reductic acid : ascorbic acid analogue"Bioorg.Med.Chem.Lett.. 10. 2783-2785 (2000)

    • Related Report
      2000 Annual Research Report

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

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