New toxic metabolites from a mushroom, Hebeloma vinosophyllum. II. Isolation and structures of hebevinosides VI, VII, VIII, IX, X, and XI.
- 1 January 1987
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 35 (6) , 2254-2260
- https://doi.org/10.1248/cpb.35.2254
Abstract
Four new triterpene glycosides, hebevinoside VI, VII, VIII, and IX, whose common aglycone is 3.beta.,7.beta.,16.beta.-trihydroxycucurbita-5,24-diene (hydroxyhebevinogenin), have been isolated from the acetone extract of a poisonous mushroom, Hebeloma vinosophyllum, and deduced to have the structures of 3.beta.,7.beta.,16.beta.-trihydroxycucurbita-5,24,-diene-3-O-.beta.-D-xylopyranoside-16-O-.beta.-D-glucopyranoside, 3.beta.,7.beta.,16.beta.-trihydroxycucurbita-5,24-diene-3-O-.beta.-D-xylopyranoside-16-O-(4,6-di-O-acetyl)-.beta.-D-glucopyranoside, 3.beta.,7.beta.,16.beta.-trihydroxycucurbita-5,24-diene-3-O-(4-O-acetyl).beta.-D-xylopyranoside-16-O-(4,6-di-O-acetyl)-.beta.-D-glucopyranoside, and 3.beta.,7.beta.,16.beta.-trihydroxycucurbita-3-O-.beta.-D-xylopyranoside, respectively. Two new glycosides, hebevinosides X and XI, whose common aglycone is 3.beta.,16.beta.-dihydroxy-7.beta.-methoxycucurbita-5,24-diene (methoxyhebevinogenin), have also been isolated from the aqueous methanolic extract of the mushroom in addition to hebevinosides I, II, III, IV, and V previously reported, and deduced to be 3.beta.,16.beta.-hydroxy-7.beta.-methoxycucurbita-5,24-diene-3-O-.beta.-D-xylopyranoside-16-O-.beta.-D-glucopyranoside and 3.beta.,16.beta.-dihydroxy-7.beta.-methoxycucurbita-5,24-diene-3-O-.beta.-D-xylopyranoside-16-O-(4,6-di-O-acetyl)-.beta.-D-glucopyranoside, respectively. Among these eleven hebevinosides, I, IV, V, X, and XI, whose common aglycone is methoxyhebevinogenin, have been proved to be artifacts formed from the genuine metabolites III, IX, II, VI, and VII, whose common aglycone is hydroxyhebevinogenin, during extraction of the mushroom with aqueous methanol, respectively, and VIII, whose aglycone is hydroxyhebevinogenin, has also been proved to be a genuine metabolite of this mushroom. The relationship between the structure and toxicity of hebevinosides was also investigated.This publication has 0 references indexed in Scilit: