69 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(その2)

概要

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Structures of hebevinosides I to XI, new metabolites from a poisonous mushroom, Hebeloma vinosophyllum Hongo, have been deduced to be 1 to 11, respectively, by their chemical and spectral evidences and on the basis of the result of the X-ray crystallographic analysis of an aglycone(22) obtained on enzymatic hydrolysis of 4. All of these glycosides are consisting of the cucurbitane-type skeleton, although the possibility that hebevinosides I, II, III, and IV might be the glycosides having the lanostane-type skeleton was previously reported. Furthermore, the hebevinosides I, IV, V, X, and XI of which common aglycone is 23 have been proved to be regarded as artifacts formed from genuine metabolites, hebevinosides III, IX, II, VI, and VII, respectively, of which common aglycone is 25, during extraction of the mushroom with aqueous methanol. Among these hebevinosides, I, II, III, V, and VI have so far been proved to be neurotropically and lethally toxic to mice. The important role of glucose at position 16 has been suggested from the investigation on the relationship between their structures and toxicities of these toxic hebevinosides.
天然有機化合物討論会の論文
1985-09-07