Studies on Trichomycin. III

Abstract

Trichomycin is an antibiotic isolated by Hosoya, et al.¹⁾ from the Streptomyces hachijoensis, which, besides being active against fungi and yeasts, is characterized by its activity against the Trichomonas group. It has been found to be an effective chemotherapeutic agent in the treatment of trichomonasis, moniliasis, etc^2),3),4).

On its structural studies, there has been scarcely any findings other than the presence of a polyene group, which had been suggested by its ultraviolet absorption spectrum⁵⁾. In the present paper, we report on several oxidation products of trichomycin, which was purified by a modified Hosoya’s method⁶⁾.

The purified sample was acetylated and then ozonized; acetaldehyde, glyoxal, and ρ-acetaminobenzoic acid have been found amongst the oxidation products. The ρ-acetamino group of ρ-acetaminobenzoic acid is presumed to be formed in the acetylation step, because purified trichomycin shows positive reactions on diazo-coupling, carbylamine and Ehrlich’s reaction. In agreement with this, p-aminoacetophenone has been obtained by KMnO₄ oxidation of a purified non-acetylated sample. The purity of the starting material, ‘purified trichomycin’, and structural units of trichomycin will be reported in the next paper⁷⁾.