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

Abstract

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_8· 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.