9 アカヒダワカフサタケの毒性代謝産物hebevinoside類の単離と構造

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The neurotropic and lethal toxicity to mice of Hebeloma vinosophyllum (Cortinariaceae) was observed by intraperitoneal administration of its aqueous methanolic extract. Both fruit-bodies of natural and cultured H. vinosophyllum were proved to be toxic, but extracts of vegetative mycelia obtained from shaking and stationary cultures in the dark were nontoxic. This fact indicated that the toxic metabolites might be produced after the formation of fruit-bodies in this mushroom. Solvent fractionation followed by repeated column chromatography of the aqueous methanolic extract of H. Vinosophyllum afforded three toxic principles, which were new compounds named hebevinosides I, II, and III. These compounds were estimated to have the triterpene glycoside structures from their chemical and spectral data. Acid hydrolysis of hebevinoside I(1) afforded an aglycone having heteroannular diene structure(3). The spectral data on 3 indicated that this compound has the cucurbitane skeleton. Although 1(lanostane-type) and 1a(cucurbitane-type) could be proposed as the possible structures for hebevinoside I to afford 3 on the acid hydrolysis, 1 was finally considered to be more likely than la, since a number of lanostane-type triterpenes have so far been isolated from the fungal species but the cucurbitane-type triterpenes have exclusively been found in the higher plants. From the same reason, 20 and 21 were also proposed to hebevinoside II and III, respectively.
天然有機化合物討論会の論文
1983-09-15

9 アカヒダワカフサタケの毒性代謝産物hebevinoside類の単離と構造

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