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Isolation of the active substances toward the neuronal receptors from Basidiomycetes

Research Project

Project/Area Number 61470145
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

NOZOE Shigeo  Pharmaceutical Inst., Tohoku University; Professor, 薬学部, 教授 (50013305)

Co-Investigator(Kenkyū-buntansha) KUSANO Genjiro  Pharmaceutical Inst., Tohoku University; Assistant Professor (KAWAZOE,Yosh), 薬学部, 助教授 (90004598)
FUSHIYA Shinji  Pharmaceutical Inst., Tohoku University; Assistant, 薬学部, 助手 (80108563)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥6,000,000 (Direct Cost: ¥6,000,000)
Fiscal Year 1987: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1986: ¥4,200,000 (Direct Cost: ¥4,200,000)
KeywordsBasidiomycetes / neurotransmitter / receptor / hallucinogens / psilobybin / baikiain / glutamine synthetase / 酵素阻害 / 神経レセプター / Psilocybin
Research Abstract

We have continued for several years on the research work aiming to isolate new compounds with activities toward the neuronal receptors and to isolate new enzyme inhibitors from the fruiting bodies of the mushrooms.
The active principle of the hallucinogenic mushroom, Psilocybe argentipes was elucidated to be psilocybin which is analogous to serotonin (5-hydroxytryptamine) and binds to the serotonin receptor.
Three new amino acid derivatives, cyclopropylalanine, (2S,4Z)-2-amino-5- chloro-6-hydroxy-4-hexenoic acid, and (2S,3'S)-1-(3-amino-3-carboxypropy1)-5- oxo-2-pyrrolidinecarboxylic acid were isolated from Amanita virgenoides, A. abrupta, and Lactarius piperatus, respectively. Taking into account their structural feature, these compounds are expected to have activities toward the neuronal receptors.
The acidic amino fraction of Clitocybe acromelalga exhibited inhibitory activity toward glutamine synthetase (GS), and the active substance was elucidated to be cytidine-5'-diphosphate.
Among the synthetic amino acid derivatives, 4-N-hydroxy-L-2,4-diaminobutyric acid showed a potent inhibitory activity toward GS. The hydroxy group of the hydroxyamino compound functions as a carboxylic acid in the enzyme reaction. <beta>-Hydroxyglutamic acid, a biogenetic precursor of neurochemically important compounds such as ibotenic aicd, tricholomic acid, and muscarine was synthesized by [3+2] dipolay cycloaddition of vinylglycine and nitrile oxide.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] Shinji Fushiya: Journal of Medicinal Chemistry. 31. 480-483 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shinji Fushiya: Journal of Medicinal Chemistry, in preparation.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shinji Fushiya: Chemistry Letters. 2229-2232 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Genjiro Kusano: Chemical & Pharmaceutical Bulletin. 35. 3482-3486 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Tomihisa Ohta: Phytochemistry. 26. 565-566 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shinji,Fushiya: "4-N-Hydroxy-L-2,4-diaminobutyric Acid, a Strong Inhibitor of Glutamine Synthetase" Journal of Medicinal Chemistry. 31. 480-483 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shinji,Fushiya: "4-N-Hydroxy-L2,4-diaminobutyric Acid, a Strong Inhibitor of Glutamine Synthetase (II) - Mechanism of Inhibition -" Journal of Medicinal Chemistry, in preparation.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Shinji,Fushiya: "Synthesis of (2S,3S,5S)-3-Hydroxy-5-methy1-2-pyrrolidinecarboxylic Acid, a Component of Actinomycin Z_1" Chemistry Letters. 2229-2232 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Genjiro,Kusano: "A New Amino Acid, (2S,3R)-(-)-3-Hydroxybaikiain from Russula subnigricans HONGO" Chemical & Pharmaceutical Bulletin. 35. 3482-3486 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Tomihisa,Ohta: "A Chlorohydrin Amino Acid from Amanita abrupta" Phytochemistry. 26. 565-566 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Musha;A.Ishii;F.Tanaka;G.Kusano: Tohoku J.Exp.Med.148. 73-78 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] G.Kusano;Y.Koike;H.Inoue;S.Nozoe: Chem.Pharm.Bull.34. 3465-3470 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] G.Kusano;H.Ogawa;A.Takahashi;S.Nozoe: Chem.Pharm.Bull.

    • Related Report
      1986 Annual Research Report
  • [Publications] S.Fushiya;M.Maeda;F.Funayama;S.Nozoe: J.Med.Chem.

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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