Metabolic Products of Fungi. XXI. On Ustilaginoidins. (1). The Reactions of Ustilaginoidin A.

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An orange red pigment, ustilaginoidin A, C28H18O10, m.p. >300°, [α]D -384° (dioxane), was isolated from false the smutted ball growing on rice spike. It has been shown that ustilaginoidin A possesses two hindered and four unhindered hydroxyls giving tetraacetate, tetrabenzoate, and hexamethyl ether. On alkaline degradation, ustilaginoidin A gave unstable product A and acetone. The product A afforded peracetate, C36H30O16, and permethyl ether, C28H30O Ustilaginoidin A hexamethyl ether yielded product B, C30H30O10, on alkaline degradation, which gave diacetate and dimethyl ether. The ultraviolet spectral study has suggested a close structural correlation between the product A and 1, 1'-binaphthalene or 1-phenylnaphthalene.

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