Metabolites of aspergilli. II. Asparvenone and O-methylasparvenone, naphthalenones from Aspergillus parvulus.

When grown on a malt extract-glucose medium, Aspergillus parvulus Smith (ATCC "169911) produced at least four metabolites detectable on thin-layer plates with ferric chloride spray. Two of these metabolities, asparvenone (7-ethyl-3,4-dihydro-4,6,8-trihydroxy-1(2H)-naphthalenone) and O-methylasparvenone (7-ethyl-3,4-dihydro-4,8-dihydroxy-6-methoxy-1(2H)-naphthalenone), were isolated and their structures determined. The structure of O-methylasparvenone was determined by chemical and spectral means and X-ray crystallographic studies of its monoacetate. The structure of asparvenone was deduced by spectral and chemical means and by methylation with diazomethane to O-methylasparvenone.