School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China; Key Laboratory of Advanced Technology of Materials, Ministry of Education, School of Material Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China.
School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China.
Fitoterapia. 2020 Oct;146:104710. doi: 10.1016/j.fitote.2020.104710. Epub 2020 Aug 31.
Three types of new Euphorbia diterpene pseudo-alkaloids possessing 5/6/7/3 (1), 5/6/6/4 (2-5), and 5/7/7/4 (6-7) fused ring skeletons were obtained through an unexpected BF·EtO/CHCN-mediated structural conversion and amination of lathyrane diterpene (Euphorbia factor L), in which the solution acetonitrile had been introduced into the Euphorbia diterpene as a nitrogen source and tandem amination/oxirane-opening (cyclopropane-opening)/oxa-Michael addition reaction was involved in the conversion. The structures of new Euphorbia diterpene pseudo-alkaloids were elucidated by a combination of spectroscopic data and single crystal X-ray diffraction analysis. The basic skeletons of Euphorbia diterpene pseudo-alkaloids 1 and 2-5 could fall into the structural types of euphoractine B and euphoractine A diterpenes, respectively, suggesting the possible biogenetic pathway relationship between lathyrane diterpene with euphoractines A and B types diterpenes. Pseudo-alkaloids 1-7 did not show any potential cytotoxicity against several tumor cell lines.
三种具有 5/6/7/3(1)、5/6/6/4(2-5) 和 5/7/7/4(6-7) 融合环骨架的新型大戟二萜伪生物碱通过出乎意料的 BF·EtO/CHCN 介导的结构转化和育亨宾二萜(Euphorbia factor L)的胺化反应获得，其中乙腈溶液被引入到 Euphorbia 二萜中作为氮源，并涉及到串联的胺化/环氧化物开环(环丙烷开环)/氧杂-Michael 加成反应。新的大戟二萜伪生物碱的结构通过光谱数据和单晶 X 射线衍射分析的组合来阐明。Euphorbia diterpene pseudo-alkaloids 1 和 2-5 的基本骨架分别属于 euphoractine B 和 euphoractine A 二萜类化合物的结构类型，表明拉坦烷二萜与 euphoractines A 和 B 型二萜之间可能存在生物合成途径关系。伪生物碱 1-7 对几种肿瘤细胞系没有显示出任何潜在的细胞毒性。
Zotero 插件