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Synthesis of Alkylpolyphenols Glycosides and the Inhibitory Effects on Superoxide Anion Production by Macrophages

Research Project

Project/Area Number 04660136
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionShinshu university

Principal Investigator

HIROTA Mitsuru  Shinshu University ; Faculty of Agriculture ; Associate professor, 農学部, 助教授 (90199133)

Co-Investigator(Kenkyū-buntansha) IRIYE Ryozo  Shinshu University ; Faculty of Agriculture ; Professor, 農学部, 教授 (20024557)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1993: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1992: ¥1,700,000 (Direct Cost: ¥1,700,000)
KeywordsActive oxygen / Superoxide anion / Macrophages / Inflammation / Polyphenols / Glycoside
Research Abstract

Superoxide anion is produced by macrophages in vivo. It is a causative agent of several diseases and also promotes inflammation. We synthesized alkylpolyphenol glycosides and examined effects of the synthetic compounds on superoxide anion production by macrophages. We also investigated anti-inflammatory activity of the synthetic compounds. Alkylcatechol xylopyranosides with various carbon chains (carbon numbers from 2 to 18), octylresorcinol xylopyranoside, octylhydroquinone xylopyranoside and octylphenol xylopyranoside were synthesized. Examining the effect of the synthetic compounds on superoxide anion production by macrophages with the modified NBT method, we found that octylcatechol xylopyranoside strongly suppressed superoxide anion production in a concentration of 50 mug/ml. Octylhydroquinone xylopyranoside and octylphenol xylopyranoside also showed similar strong activity. Using mouse ear inflammation test, we also examined anti-inflammatory activity of the synthetic compounds. Octylcatechol xylopyranoside, octylhydroquinone xylopyranoside, octylphenol xylopyranoside showed strong inhibitory activity. A sugar moiety and an alkyl chain with proper length are important structural factors for the presence of both effects on superoxide anion production and inflammation. Furthermore, we examined the reactivity of decylcatechol xylopyranoside with radicals using anti-oxidation test. It markedly suppressed autooxidation of linoleic acid in a concentration of 1Oppm. These compounds may directly react with superoxide anion (radical).

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] 廣田満,米山恵子他: "マクロファージが産生する活性酸素の測定-NBT法の改良" 日本農芸化学会誌. 66. 292 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 廣田満,本田智一郎,入江鐐三: "Acylphloroglucinolの炎症抑制活性" 日本農芸化学会誌. 68. 538 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota,N.Tamura,et.al.: "Plant Constituents with Anti-inflammatory Activity" Seminar of Chemistry of Rainforest Pants and their Utilization for Development,Bukit Tinggi,Indonesia Abstracts. 117-118 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota,T.Kojima,et.al.: "Methyl Pheophorbide b as an Anti-inflammatory Compound from Clematis terniflora DC." XV International Botanical Congress,Yokohama,Abstracts. 384 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota,S.Takahashi,et.al.: "Alkylpolyphenol Xylopyranosides Suppress Superoxide Anion Production by Mouse Peritoneal Macrophages" Bioscience,Biotechnology and Biochemistry. (投稿準備中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota, , K.Yoneyama, N.Tamura, S.Takahashi, Y.Ohsugi and R.Iriye: "Determination of Macrophages-Produced Superoxide Anion with the Improved NBT Method" Nippon Nogeikagaku Kaishi. 66. 292 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota, T.Honda, and R.Iriye: "Anti-inflammatory Activity of Acylphloroglucinols" Nippon Nogeikagaku Kaishi. 68. 538 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota, N.Tamura, T.Suzuki, A.Kakehi and R.Iriye: "Plant Constituents with Anti-inflammatory Activity" Seminar of Chemistry of Rainforest Pants and their Utilization for Development, Bukit Tinggi, Indonesia. (Abstracts). 117-118 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota, T.Kojima, K.Tateishi, R.Iriye, H.Takada, I.Sakata: "Methyl Pheophorbide b as an Anti-inflammatory Compound from Clematis terniflora DC" XV International Botanical Congress, Yokohama. (Abstracts). 384 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] M.Hirota, S.Takahashi, N.Tamura, K.Yoshida, R.Iriye: "Alkylpolyphenol Xylopyranosides Suppress Superoxide Anion Production by Mouse Peritoneal Macrophages" (in preparation).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 廣田 満: "Acylphloroglucinolの炎症抑制活性" 日本農芸化学会誌. 8. 538 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Hirota,T.Kojima,et.al.: "Methyl Pheophorbide b as an Anti-inflammatory Compound from Clematis terniflora DC." XV international Botanical Congress,Yokohama,Abstracts. 384 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] 廣田 満: "マクロファージが産生する活性酸素の測定ーNBT法の改良" 日本農芸化学会誌. 66. 292-292 (1992)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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