消除丁基环庚基灵菌红素作为一种已知的天然产物，这是基于环灵菌红素生物合成的进化假说。
Elimination of butylcycloheptylprodigiosin as a known natural product inspired by an evolutionary hypothesis for cyclic prodigiosin biosynthesis.
机构信息
Department of Chemistry, Northwestern University , Evanston, Illinois 60208, United States.
出版信息
J Nat Prod. 2013 Oct 25;76(10):1937-45. doi: 10.1021/np400531b. Epub 2013 Sep 20.
The cyclic prodigiosins are an important family of bioactive natural products that continue to be the subject of numerous structural, synthetic, and biosynthetic studies. In particular, the structural assignments of the isomeric cyclic prodigiosins butylcycloheptylprodigiosin (BCHP) and streptorubin B have been the cause of significant confusion. Herein, we report detailed studies regarding the electron impact (EI) mass spectra of synthetic BCHP and streptorubin B that have allowed us to distinguish the two compounds in the absence of quality historical isolation NMR data. On the basis of these fragmentation differences, the status of BCHP as a natural product is challenged. The proposed mechanism of fragmentation is supported by the EI mass spectra of synthetic pentyl-chain analogues of BCHP and streptorubin B, X-ray crystallography, and DFT calculations. Elimination of BCHP from the prodigiosin family supports a proposed evolutionary hypothesis for the surprising biosynthesis of cyclic prodigiosins.
环多杀菌素是一类重要的生物活性天然产物，它们仍然是许多结构、合成和生物合成研究的主题。特别是，同系物环多杀菌素丁基环己基多杀菌素（BCHP）和 Streptorubin B 的结构分配一直是引起重大混淆的原因。在此，我们报告了关于合成 BCHP 和 Streptorubin B 的电子冲击（EI）质谱的详细研究，这些研究使我们能够在没有质量历史分离 NMR 数据的情况下区分这两种化合物。基于这些断裂差异，BCHP 作为天然产物的地位受到了挑战。所提出的断裂机制得到了 BCHP 和 Streptorubin B 的合成戊基链类似物的 EI 质谱、X 射线晶体学和 DFT 计算的支持。BCHP 从多杀菌素家族中的消除支持了一个关于环状多杀菌素惊人生物合成的进化假说。
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