(+)- and (−)-Ecarlottones, Uncommon Chalconoids from Fissistigma latifolium with Pro-Apoptotic Activity,Journal of Natural Products

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(+)- and (−)-Ecarlottones, Uncommon Chalconoids from Fissistigma latifolium with Pro-Apoptotic Activity
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-21 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00494
Charlotte Gény ₁ , Alma Abou Samra ₁ , Pascal Retailleau ₁ , Bogdan I. Iorga ₁ , Hristo Nedev ₁ , Khalijah Awang ₂ , Fanny Roussi ₁ , Marc Litaudon ₁ , Vincent Dumontet ₁

Affiliation

Four new compounds, (+)- and (−)-ecarlottone (1), (±)-fislatifolione (5), (±)-isofislatifolione (6), and (±)-fislatifolic acid (7), and the known desmethoxyyangonin (2), didymocarpin-A (3), and dehydrodidymocarpin-A (4) were isolated from the stem bark of Fissistigma latifolium, by means of bioassay-guided purification using an in vitro affinity displacement assay based on the modulation of Bcl-xL/Bak and Mcl-1/Bid interactions. The structures of the new compounds were elucidated by NMR spectroscopic data analysis, and the absolute configurations of compounds (+)-1 and (−)-1 were assigned by comparison of experimental and computed ECD spectra. (−)-Ecarlottone 1 exhibited a potent antagonistic activity on both protein–protein associations with K_i values of 4.8 μM for Bcl-xL/Bak and 2.4 μM for Mcl-1/Bid.

中文翻译：

（+） -和（ - ） - Ecarlottones，稀有Chalconoids从瓜馥宽叶与促凋亡活性

四种新化合物，（+）-和（-）-异丁酮（1），（±）-非斯拉替利酮（5），（±）-异非斯拉替利酮（6）和（±）-非斯拉替夫酸（7），并且是已知的通过体外亲和力置换实验，基于调节Bcl-2的体外亲和力置换法，从阔叶菲的茎皮中分离了Demethoxymethoxyon（2），Didymocarpin-A（3）和dehydrodidymocarpin-A（4）。 xL / Bak和Mcl-1 / Bid交互。通过NMR光谱数据分析阐明了新化合物的结构，以及化合物（+）- 1和（-）- 1的绝对构型通过比较实验和计算出的ECD光谱来分配。（-）-Ecarlottone 1对两种蛋白质-蛋白质的结合都表现出强大的拮抗作用，Bcl-xL / Bak的K _i值为4.8μM ，Mcl-1 / Bid的K _i值为2.4μM 。

更新日期：2017-11-21

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