Studies in the biochemistry of micro-organisms. 99. Metabolic products of Aspergillus versicolor (Vuillemin) Tiraboschi

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Abstract
Sterigmatocystin, a crystalline metabolic product obtained from the mycelium of Aspergillus versicolor by extraction with light petroleum was isolated as pale-yellow needles of mp. 247[degree], [[alpha]] 20- 398[degree]. It contains one molecular formula C18H12O6. The following derivatives were prepared; diacetate (hydrate), m.p. 228[degree], monomethyl ether, m.p. 271[degree], monoethyl ether, m.p. 261[degree]. On fusion with potassium hydroxide sterigmatocystin yields resorcinol and acetic acid, and on zinc-dust distillation small amounts of anthracene or a homologue. When heated with 25% ethanolic potassium hydroxide sterigmatocystin furnishes an optically inactive isomer, isosterigmatocystin, m.p. 234[degree], yielding a diacetate, m.p. 197[degree], and a methyl ether, m.p. 162[degree]. A second optically active crystalline product, m.p. 233[degree], was obtained in small yield from the mycelium by ether extraction. Mannitol was extracted by methanol from the mycelium as a third metabolic product.