On the biosynthesis of some polyketide metabolites in Alternariasolani: 13C and 2Hmr studies

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Abstract
13C nuclear magnetic resonance spectroscopy has revealed that cultures of the fungus Alternariasolani incorporate [1,2-13C2]acetate into the anthraquinone macrosporin (3) and the tetrahydroanthraquinones altersolanol A (4) and dactylariol (6) from a single octaketide chain. The carbon skeleton of 4-13Cx was incorporated intoto into 3, with 6 as a probable intermediate; there is also evidence that 4 may be a precursor of altersolanol B (5). The 2Hmr spectra show that deuterium from [1-13C1, 2-2H3]acetate is retained to a considerable extent in the C-methyl groups and the 1, 6, and 8 positions of 3 and 4 but is completely lost from the 3-position in 4. Zinniol (7), also a metabolite of the fungus, is a normal tetraketide.