FURTHER METABOLIC STUDIES OF INDOLE AND SUGAR-DERIVATIVES USING THE STAUROSPORINE PRODUCER STREPTOMYCES-STAUROSPOREUS

During our continuing studies of staurosporine (1) biosynthesis and th e metabolism of indole derivatives, three additional novel metabolites , beta-hydroxy-N-b-acetyltryptamine (7) and its 5- and 6-fluoro deriva tives (8 and 9, respectively), were isolated, respectively, from the f eeding of tryptamine and 5- and 6-fluorotryptamines using Streptomyces staurosporeus. In addition, two new 5-hydroxytryptamine (serotonin) m etabolites, N-b-acetyltryptamine-5-O-beta-D-quinovopyranoside (11) and N-b-acetyltryptamine-5-O-alpha-L-rhamnopyranoside (12), were isolated along with 5-hydroxy-N-b-acetyltryptamine (10). From a glucose contai ning medium, 6-O-acetylglucose and its C-13 uniformly labeled derivati ve were isolated from a culture of S. staurosporeus during biosyntheti c studies of 1. In 2-deoxyglucose metabolism studies, 6-O-acetyl-2-deo xyglucose was isolated and identified as a metabolic product of 2-deox yglucose. A copper-enzyme inhibitor, N,N-diethyldithiocarbamic acid, w as evaluated for the accumulation of staurosporine intermediates; howe ver, no modified staurosporines were observed.