Biosynthesis of flaviolin and 5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone

Tracer experiments indicate a polyketide origin for the production of flaviolin (2,5,7-trihydroxy-1,4-naphthoquinone) by Aspergillus niger and 2,7-dimethoxynaphthazarin (5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone) by Streptomyces no. 12396. With the Streptomycete, a "solid state fermentation" technology was used for the incorporation studies. Radioactivity from shikimic acid was effectively incorporated into flaviolin; this conversion, however, proceeded by way of acetic acid. The latter stages of biosynthesis of 2,7-dimethoxynaphthazarin by the Streptomycete were shown to be as follows: flaviolin leads to mompain leads to 2,7-dimethoxynaphthazarin.