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.
D000085:Acetates / Q000378:metabolism; D001230:Aspergillus / Q000378:metabolism*; D001234:Aspergillus niger / Q000378:metabolism*; D001565:Benzoates / Q000378:metabolism; D005415:Flavins / Q000096:biosynthesis*; D005971:Glutamates / Q000378:metabolism; D008314:Malonates / Q000378:metabolism; D008715:Methionine / Q000378:metabolism; D009285:Naphthoquinones / Q000096:biosynthesis*; D010084:Oxidation-Reduction; D012765:Shikimic Acid / Q000378:metabolism; D013045:Species Specificity; D013302:Streptomyces / Q000378:metabolism*; D013386:Succinates / Q000378:metabolism; D013997:Time Factors
D000085:Acetates; D001565:Benzoates; D005415:Flavins; D005971:Glutamates; D008314:Malonates; D009285:Naphthoquinones; D013386:Succinates; D012765:Shikimic Acid; D008715:Methionine