1987 Fiscal Year Final Research Report Summary
Isolation of the active substances toward the neuronal receptors from Basidiomycetes
| Project/Area Number |
61470145
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
NOZOE Shigeo Pharmaceutical Inst., Tohoku University; Professor, 薬学部, 教授 (50013305)
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| 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)
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| Project Period (FY) |
1986 – 1987
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| Keywords | Basidiomycetes / neurotransmitter / receptor / hallucinogens / psilobybin / baikiain / glutamine synthetase / 酵素阻害 |
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| 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.
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