Studies in the biosynthesis of fungal metabolites. 4. Alternariol monomethyl ether and its relation to other phenolic metabolites of Alternaria tenuis

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Abstract
Alternarioi monomethyl ether C15H12O5, a metabolite of Alternaria tenuis Auct., has been shown to be 3:4'' -dihydroxy-5-methoxy-6'' -methyldibenzo-[alpha]-pyrone (III). The position of the methoxyl group was established (a) by comparison of the infrared carbonyl frequencies of alternarioi and alternarioi monomethyl ether with the fully methylated product, and (b) by sequential methylation of alternarioi monomethyl ether with [14C] methyl iodide and dimethyl sulphate, followed by oxidative degradation of the resulting labelled trimethyl ether. A tentative biosynthesis in-terrelationship between alternarioi monomethyl ether and the other phenolic constiuents of A. tenuis is proposed on the basis of their known properties.