Metabolism studies of indole derivatives using a staurosporine producer, Streptomyces staurosporeus.
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 Nb-acetyltryptamine using S. staurosporeus fed with tryptamine. The unusual compound 2 was proposed as a further metabolite of Nb-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.
Yang
S W
SW
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.
Cordell
G A
GA
D003470:Culture Media; D005285:Fermentation; D007211:Indoles / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D019311:Staurosporine / Q000096:biosynthesis*; D013302:Streptomyces / Q000378:metabolism*; D014364:Tryptophan / Q000378:metabolism
D003470:Culture Media; D007211:Indoles; D014364:Tryptophan; D019311:Staurosporine