New toxic metabolites from a mushroom, Hebeloma vinosophyllum. I. Structures of Hebevinosides I, II, III, IV, and V.

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Abstract
The structures of hebevinosides I, II, III, IV, and V, new metabolites from a poisonous mushroom, Hebeloma vinosophyllum, were deduced to be 3.beta.,16.beta.-dihydroxy-7.beta.-methoxycucurbita-5,24-diene-3-O-.beta.-D-xylopyranoside-16-O-(6-O-acetyl)-.beta.-D-glucopyranoside (1), 3.beta.,7.beta.,16.beta.-trihydroxycucurbita-5,24-diene-3-O-(4-O-acetyl)-.beta.-D-xylopyranoside-16-O-(6-O-acetyl)-.beta.-D-glucopyranoside (22), 3.beta.,7.beta.,16.beta.-trihydroxycucurbita-5,24-diene-3-O-.beta.-D-xylopyranoside-16-O-(6-O-acetyl).beta.-D-glucopyranoside (24), 3.beta.,16.beta.-dihydroxy-7.beta.-methoxycucurbita-5,24-diene-3-O-.beta.-D-xylopyranoside (16), and 3.beta.,16.beta.-dihydroxy-7.beta.-methoxycucurbita-5,24-diene-3-O-(4-O-acetyl).beta.-D-xylopyranoside-16-O-(6-O-acetyl)-.beta.-D-glycopyranoside (27), respectively, on the basis of chemical and spectral evidence, as well as the structure determination by X-ray crystallographic analysis of ethoxyhebevinogenin (20), obtained by enzymatic hydrolysis of 16. Hebevinosides I, II, III, and V were proved to be toxic principles of this mushroom.