Studies on Structure of Griseolutein B, a Streptomyces Antibiotic. I. Characterization and Degradation.

Abstract

Griseolutein-B and-A were purified by the counter-current distribution method and their properties were examined. Diacetylgriseolutein-B was easily purified and crystallized. It had one methoxyl group, two acetyl groups, and one carboxyl group, but no C-methyl group or N-oxide group. Its methyl ester was obtained. Alkaline hydrolysis of diacetylgriseolutein-B gave griseoluteic acid which was crystallized as its methyl ester or as monomethyl ester of monoacetylgriseoluteic acid. Distillation of griseoluteic acid with zinc dust gave phenazine, 1-methoxyphenazine, and another compound. This compound was identified as 1-methoxy-4-methylphenazine by comparison with the synthesized sample. 1-methoxy-4-methylphenazine was synthesized from aniline and 3-nitro-4-methoxytoluene and its two crystal forms were observed.