Metabolism Studies of Indole Derivatives Using a Staurosporine Producer, Streptomyces staurosporeus

• Published in: Journal of natural products (Washington, D.C.) Vol. 60; no. 1; pp. 44 - 48
• Main Authors: Yang, Shu-Wei, Cordell, Geoffrey A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.01.1997; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Bacteriology; Biological and medical sciences; Chemistry, Medicinal; Culture Media; Fermentation; Fundamental and applied biological sciences. Psychology; Indoles - chemistry; Indoles - metabolism; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Metabolism. Enzymes; Microbiology; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; Staurosporine - biosynthesis; Streptomyces - metabolism; Tryptophan - metabolism; POTENT INHIBITOR; PROTEIN-KINASE-C; Streptomycetaceae; Nitrogen heterocycle; Metabolite; Streptomyces; Tryptamine derivatives; Tryptophan; Tricyclic compound; Actinomycetales; Microbial origin; Bicyclic compound; Bacteria; Isolation; Actinomycetes; Aromatic compound; Indole derivatives; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960566u

From a tryptophan metabolic study, 3-(hydroxyacetyl)indole, indole-3-carboxaldehyde, and o-aminobenzoic acid were obtained as tryptophan metabolites from a staurosporine (1) producer, Streptomyces staurosporeus. A new tryptamine metabolite, (3aR,8aS)-1-acetyl-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 proposed as a further metabolite of N b-acetyltryptamine through an enzymatic oxidative cyclization. Examination of the metabolites from the feeding 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 derivative of 2. Indole-ring-substituted metabolites of staurosporine (1) were not observed.