title: Further metabolic studies of indole and sugar derivatives using the staurosporine producer Streptomyces staurosporeus.
abstract: During our continuing studies of staurosporine (1) biosynthesis and the metabolism of indole derivatives, three additional novel metabolites, beta-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-beta-D-quinovopyranoside (11) and Nb-acetyltryptamine-5-O-alpha-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.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 00612, USA.
authors.forename: S W
authors.initials: SW
authors.lastname: Yang
authors.forename: G A
authors.initials: GA
authors.lastname: Cordell
mesh_terms: D000963:Antimetabolites / Q000494:pharmacology; D050260:Carbohydrate Metabolism; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry; D002855:Chromatography, Thin Layer; D003470:Culture Media; D003847:Deoxyglucose / Q000494:pharmacology; D004050:Ditiocarb / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000494:pharmacology; D005285:Fermentation; D007211:Indoles / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019311:Staurosporine / Q000096:biosynthesis* / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*
chemical_list: D000963:Antimetabolites; D002241:Carbohydrates; D003470:Culture Media; D004791:Enzyme Inhibitors; D007211:Indoles; D004050:Ditiocarb; D003847:Deoxyglucose; D019311:Staurosporine