Further Metabolic Studies of Indole and Sugar Derivatives Using the Staurosporine ProducerStreptomyces staurosporeus

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Abstract
During our continuing studies of staurosporine (1) biosynthesis and the metabolism of indole derivatives, three additional novel metabolites, β-hydroxy-Nb-acetyltryptamine (7) and its 5- and 6-fluoro derivatives (8 and 9, respectively), were isolated, respectively, from the feeding of tryptamine and 5- and 6-fluorotryptamines using Streptomyces staurosporeus. In addition, two new 5-hydroxytryptamine (serotonin) metabolites, Nb-acetyltryptamine-5-O-β-d-quinovopyranoside (11) and Nb-acetyltryptamine-5-O-α-l-rhamnopyranoside (12), were isolated along with 5-hydroxy-Nb-acetyltryptamine (10). From a glucose containing medium, 6-O-acetylglucose and its 13C uniformly labeled derivative were isolated from a culture of S. staurosporeus during biosynthetic studies of 1. In 2-deoxyglucose metabolism studies, 6-O-acetyl-2-deoxyglucose was isolated and identified as a metabolic product of 2-deoxyglucose. A copper-enzyme inhibitor, N,N-diethyldithiocarbamic acid, was evaluated for the accumulation of staurosporine intermediates; however, no modified staurosporines were observed.