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Structurally Diverse Indole Alkaloids with Vasorelaxant Activity from Melodinus hemsleyanus.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-07-19 , DOI: 10.1021/acs.jnatprod.9b00925
Jian Zhang 1 , Zhi-Wen Liu 1 , Yong Li 1 , Cui-Jie Wei 1 , Jing Xie 1 , Meng-Fei Yuan 1 , Dong-Mei Zhang 1 , Wen-Cai Ye 1 , Xiao-Qi Zhang 1
Affiliation  

Six new structurally diverse indole alkaloids, melohemsines J–M (14), 11-hydroxy-Δ14-vincamine (5), and 11-hydroxy-16-epi14-vincamine (6), and 15 known alkaloids were isolated from the leaves and twigs of Melodinus hemsleyanus Diels. These new compounds and their absolute configurations were determined through spectroscopic data analyses, X-ray diffraction, and computational methods. Melohemsine J (1) is the first example of a melodinus-type alkaloid possessing a 6/6/5/5/6/5 hexacyclic skeleton and containing a tetrahydrofuro[2,3-b]pyridine-2(3H)-one unit. Melohemsine K (2) is an unusual aspidosperma-type alkaloid possessing a 6/5/6/5/5 pentacyclic architecture with a contracted E ring (loss of CH2). Compounds 510 and 16 exhibited vasorelaxant activities with EC50 values of 0.8–3.8 μM. In addition, compound 4 displayed moderate cytotoxicity toward the tumor cell lines HepG2 and A-549 with EC50 values of 18.7 and 28.7 μM, respectively.

中文翻译:

来自 Melodinus hemsleyanus 的具有血管舒张活性的结构多样的吲哚生物碱。

六种新的结构多样的吲哚生物碱、 melohemsines J–M ( 14 )、11-羟基-Δ 14 -长春胺 ( 5 ) 和 11-羟基-16 - epi14 -长春胺 ( 6 ) 和 15 种已知生物碱从Melodinus hemsleyanus Diels的叶子和树枝中分离出来。这些新化合物及其绝对构型是通过光谱数据分析、X 射线衍射和计算方法确定的。Melohemsine J ( 1 ) 是具有 6/6/5/5/6/5 六环骨架并含有四氢呋喃 [2,3- b ]pyridine-2(3 H)-一个单元。Melohemsine K ( 2 ) 是一种不寻常的有丝植物型生物碱,具有 6/5/6/5/5 五环结构和收缩的 E 环(失去 CH 2)。化合物5 - 1016个与EC展出血管舒张活动50 0.8-3.8μM的值。此外,化合物4对肿瘤细胞系 HepG2 和 A-549 显示出中等的细胞毒性,EC 50值分别为 18.7 和 28.7 μM。
更新日期:2020-08-28
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