天然有機化合物討論会講演要旨集
Online ISSN : 2433-1856
セッションID: 15
会議情報
15 おおわらいたけの神経興奮性成分 : ジムノピリンについて(口頭発表の部)
田中 正泰針ヶ谷 弘子鎌田 樹志氏原 一哉橋本 勝橋本 貴美子松田 冬彦柳屋 光俊白濱 晴久奥野 智旦
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会議録・要旨集 フリー

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Ohwaraitake is Japanese name of a poisonous mushroom Gymnopilus spectabilis and means "a loud laugh mushroom". Accidental ingestion of it causes hallucinosis and abnormal behavior. A hallucinogenic mushroom contains usually psilocybin or its analogues but it is reported that any psilocybin or its congenor does not found in Japanese Ohwaraitake. The toxic symptoms suggest that any neuroexcitatory substance must be contained. The isolation was carried out monitoring depolarizing activity on the new born rat spinal cord. 1. Chromatographical fractionation and bisassay showed that the neuroexcitatory active compounds were gimnopilins (G) which were known as bitter principles of this fungus. Further fractionation revealed that G (1) was inactive and activities of G (2) increased from n=7 to n=5 and besides, G (2), which was newly isolated this time, was more active than G (2). 2. The structure of the new G was determined by the chemical degradation as formula 3. 3. The Chirality of hydroxymethylglutamic acid (HMGA) part was determined as S configuration by the acquisition of (R)-mevalonaloctone through LiBH4 reduction or G (1 and 2). 4. G (2) does not work as an ion carrier probably, since it does not particularly take metal ion from aqueous solution into an organic solvent. 5. Determination of the chirality of tert-alcohols in gymnoprenol (G'), that is, G without HMGA part, was attempted. Eight isomers of the model compounds corresponding to G' (m=2, n=4) were synthesized and were not discriminated by HPLC and NMR. Since two diastereoisomers of MTP-ethoxy-methoxy derivatives of G' (m=1, n=2) were distinguished by ^1H and ^<19>FNMR, these derivatives may be applicable to identification of the synthetic and the natural G'.

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© 1992 天然有機化合物討論会電子化委員会
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