Biosynthesis of Scorpinone, a 2-Azaanthraquinone from Amorosia littoralis, a Fungus from Marine Sediment

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Abstract
The biogenetic origin of the carbon atoms in the 2-azaanthraquinone scorpinone (1), produced by the rare fungus Amorosia littoralis isolated from marine sediment, was explored through isotopic enrichment studies utilizing [2-13C]-acetate and [1,2-13C]-acetate. The labeling results reveal a heptaketide precursor is involved in the biosynthesis of 1, as has been found for the structurally related naphthoquinone dihydrofusarubin. The previously identified naphthoquinone herbarin (2) was also isolated and appears to bear the same biogenetic relationship to 1 as the fusarubins do to the fungal 2-azaanthraquinone bostrycoidins.

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