Biotransformation of dehydroparadols byAspergillus niger

To prove uniqueness of allylic alcohol formation from α,β-unsaturated ketones by mammal enzymes, a metabolic pattern of dehydroparadols, non-pungent synthetic analogs of shogaol byAspergillus niger was examined. Two biotransformation products of a dehydroparadol, 1-(4-hydroxy-3-methoxyphenyl)-non-1-en-3-one were accumulated in the culture broth ofA. niger. They were characterized as 1-(4-hydroxy-3-methoxyphenyl)-non-1-en-9-ol-3-one and 1-(4-hydroxy-3-methoxyphenyl)-nonan-9-ol-3-one by UV, NMR and mass spectroscopic analyses. Accumulation of allylic alcohol metabolites was not observed.