METABOLISM STUDIES OF INDOLE-DERIVATIVES USING A STAUROSPORINE PRODUCER, STREPTOMYCES-STAUROSPOREUS

From a tryptophan metabolic study, 3-(hydroxyacetyl)indole, indole-3-c arboxaldehyde, and o-aminobenzoic acid were obtained as tryptophan met abolites from a staurosporine (1) producer, Streptomyces staurosporeus . A new tryptamine metabolite, l-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b] indol-3a-ol (2), was isolated along with N-b-acetyltryptamine using S. staurosporeus fed with tryptamine. The unusual compound 2 was propose d as a further metabolite of N-b-acetyltryptamine through an enzymatic oxidative cyclization. Examination of the metabolites from the feedin g of 5- and 6-fluorotryptamines using the same microorganism afforded the two novel compounds 3 and 4 as the 5- and 6-fluoro derivatives of 2. However, 5-hydroxytryptamine failed to generate the 5-hydroxy deriv ative of 2. Indole-ring-substituted metabolites of staurosporine (1) w ere not observed.