Studies in the biochemistry of micro-organisms

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Abstract
The coloring matter present in cultures of P. clavariaejormis, grown in the dark at 24[degree], was isolated in good yield and is named penicilliopsin. Its formula is C30H24O8. It consists of orange prisms M.P. 330[degree] (decomp.), and is oxidized in air in suitable solvents to Oxypemcilliopsin, C30H20O9, purple-black crystalline aggregates, M.P. above 360[degree], solns. of which, on exposure to light, are converted into the isomeric irradiated oxypenicil-liopsin, Ca30H20O9, chocolate-brown needles M.P. above 370[degree], which gave intensely fluorescent solns. The coloring matter from naturally occurring specimens of P. clavariaejormis, which was formerly known as mycoporphyrin, was probably a mixture of penicilliopsin, oxypenicilliopsin and irradiated oxypenieilliopsin. Irradiated oxypenicilliopsin is closely related to hypericin the coloring matter of Hypericum perjoratum. Several derivatives and breakdown products of penicilliopsin are descr. Since it gives Frangula-emodm an-thranol on heating alone and tetranitroemodin on oxidation with HNO3, it may be a polyhydroxy derivative of a reduced mesodimethyldianthrone.