Yang S W, Cordell G A
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.
J Nat Prod. 1997 Jan;60(1):44-8. 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 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.
通过色氨酸代谢研究，从星形孢菌素（1）产生菌星状链霉菌中获得了3-（羟基乙酰基）吲哚、吲哚-3-甲醛和邻氨基苯甲酸作为色氨酸代谢产物。使用喂食色胺的星状链霉菌，分离出一种新的色胺代谢产物（3aR，8aS）-1-乙酰基-1,2,3,3a,8,8a-六氢吡咯并[2,3-b]吲哚-3a-醇（2）以及N-乙酰色胺。不寻常的化合物2被认为是N-乙酰色胺通过酶促氧化环化产生的进一步代谢产物。使用同一微生物对5-氟色胺和6-氟色胺喂食后的代谢产物进行检测，得到了两种新型化合物3和4，它们是化合物2的5-氟和6-氟衍生物。然而，5-羟色胺未能产生化合物2的5-羟基衍生物。未观察到星形孢菌素（1）的吲哚环取代代谢产物。
