New cyanocyclines from a cyanide-treated broth of Streptomyces lusitanus.
New cyanocyclines from a cyanide-treated broth of Streptomyces lusitanus.
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DOI：
10.1021/np50098a006
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发表时间：
1993-08
影响因子：
5.1
通讯作者：
S. Gould;W. He;M. C. Cone
中科院分区：
文献类型：
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作者：
S. Gould;W. He;M. C. Cone
抗肿瘤抗生素萘啶霉素[1]的生产者葡萄牙链霉菌的有机提取物被发现含有两种在抗生素筛选中具有活性的额外化合物。与1一样，这些与在发酵结束时加入的NaCN反应。加成产物之一被命名为氰环素B [3]，衍生自N-去甲基萘啶霉素[4]，而另一种被命名为氰环素C [5]，衍生自1的氢醌6。蓝环素C是不稳定的，并且在TFA存在下用CH 2N 2转化为二甲基衍生物后进行表征。这些代谢产物的生物合成1的影响进行了讨论。第三种新的抗生素，氰环素D [8]从氰化物处理的肉汤中分离出来，并被证明是一种人工制品，其中恶唑烷环已被氰化物打开。还讨论了8的形成与1与DNA反应的潜在相关性。
Organic extracts of Streptomyces lusitanus, the producer of the anticancer antibiotic naphthyridinomycin [1], were found to contain two additional compounds active in an antibiotic screen. As with 1, these reacted with NaCN added at the end of the fermentation. One of the addition products has been named cyanocycline B [3] and is derived from N-desmethylnaphthyridinomycin [4], while the other has been named cyanocycline C [5], and is derived from the hydroquinone 6 of 1. Cyanocycline C is unstable and was characterized after conversion to the dimethyl derivative with CH2N2 in the presence of TFA. The implications of these metabolites for the biosynthesis of 1 are discussed. A third new antibiotic, cyanocycline D [8] was isolated from the cyanide-treated broth and proved to be an artifact in which the oxazolidine ring had been opened by cyanide. The potential relevance of the formation of 8 to the reaction of 1 with DNA is also discussed.