Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
New Toxic Metabolites from a Mushroom, Hebeloma vinosophyllum. III. Isolation and Structures of Three New Glycosides, Hebevinosides XII, XIII and XIV, and Productivity of the Hebevinosides at Three Growth Stages of the Mushroom
Haruhiro FUJIMOTOKaijiro MAEDAMikio YAMAZAKI
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1991 Volume 39 Issue 8 Pages 1958-1961

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Abstract

Three new triterpene glycosides, hebevinosides XII, XIII and XIV, were isolated besides five already known neurotoxic hebevinosides from acetone extract of the mycelium with primordia of a poisonous mushroom, Hebeloma vinosophyllum, and their structures were deduced to be 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-O-β-D-xylopy-ranoside-16-O-(4-O-acetyl)-β-D-glucopyranoside, 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-O-(3, 4-di-O-acetyl)-β-D-xylopyranoside-16-O-(4, 6-di-O-acetyl)-β-D-glucopyranoside and 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-O-(3, 4-di-O-acetyl)-β-D-xylopyranoside-16-O-(6-O-acytyl)-β-D-glucopyranoside, respectively.Productivity of the eight hebevinosides was studied at three growth stages of the organism; mycelium (stage I), mycelium with primordia (stage II) and mycelium with fruit-bodies (stage III). The ratio of production of total hebevinosides at stages I : II : III was approximately 6 : 4 : 25. Production of hebevinosides VII, XIV, XIII, VIII and XII having the acetyl groups at O-4 in the glucosyl and/or O-3 in the xylosyl moieties, which are comparatively labile, decreased, and that of hebevinosides III and II having the acetyl groups at O-6 in the glucosyl and/or O-4 in the xylosyl moieties, which are relatively stable, increased in the time course from stage I to stage III. On the other hand, production of hebevinoside VI having no acetyl group was independent of the growth stages. Production of ergostane-type sterols seemed to be activated for the first time at stage III in the organism.

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