Isolation, identification and pharmacological studies on three toxic metabolites from a mushroom, Hebeloma spoliatum

Three metabolites, tentatively named HS-A, -B and -C, were isolated from a mushroom, Hebeloma spoliatum, as the fatal toxic principles to mice. HS-A was identified as 3-acetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol, which has been isolated from Hebeloma crustuliniforme and H. sinapizans as a cytotoxic principle. HS-B and -C were deduced to be 3,21-diacetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol and 3-acetyl-2-(3'-hydroxy-3'-methyl)glutarylanhydrocrustulinol, respectively, from their chemical and spectral data. Intraperitoneal administration of HS-A, -B and -C at a dose of 100 mg/kg caused death after paralysis of the limbs in mice. The compounds caused relaxation of mouse small intestine contracted by acetylcholine chloride or barium chloride treatment in vitro. They appear to exhibit a papaverine-like relaxation effect.