Gelsecorydines A-E, Five Gelsedine-Corynanthe-Type Bisindole Alkaloids from the Fruits of Gelsemium elegans
Gelsecorydines A-E, Five Gelsedine-Corynanthe-Type Bisindole Alkaloids from the Fruits of Gelsemium elegans
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Gelsecorydines A-E，来自秀丽隐杆线虫果实的五种 Gelsedine-Corynanthe 型双吲哚生物碱
DOI：
10.1021/acs.joc.8b00736
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发表时间：
2018-05-18
影响因子：
3.6
通讯作者：
Wang, Lei
中科院分区：
文献类型：
--
作者：
Li, Ni-Ping;Liu, Miao;Wang, Lei
从钩吻果实中分离得到5个具有新碳骨架的单萜双吲哚生物碱，即钩吻碱A-E（1-5）及其生物前体。化合物1-5代表由gelsedine型生物碱和修饰的corynanthe型生物碱组成的异二聚体框架的第一个实例。值得注意的是，化合物2具有前所未有的笼状骨架，具有6/5/7/6/5/6杂六环系统，其具有连接两个单体的吡啶环。通过光谱分析、X-射线衍射和电子圆二色谱（ECD）计算确定了它们的结构和绝对构型。提出了化合物1-5的合理生物合成途径。化合物1、3、4和5对巨噬细胞产生一氧化氮（NO）表现出显著的抑制作用。
Five monoterpenoid bisindole alkaloids with new carbon skeletons, gelsecorydines A-E (1-5), together with their biogenetic precursors were isolated from the fruits of Gelsemium elegans. Compounds 1-5 represent the first examples of heterodimeric frameworks composed of a gelsedine-type alkaloid and a modified corynanthe-type one. Notably, compound 2 featured an unprecedented caged skeleton with a 6/5/7/6/5/6 heterohexacyclic ring system, which possessed a pyridine ring that linked the two monomers. Their structures and absolute configurations were elucidated by spectroscopic analysis, X-ray diffraction, and electronic circular dichroism (ECD) calculation. A plausible biosynthetic pathway for compounds 1-5 is proposed. Compounds 1, 3, 4, and 5 exhibited a significant inhibitory effect against nitric oxide (NO) production in macrophages.