NMR strategy for unraveling structures of bioactive sponge-derived oxy-polyhalogenated diphenyl ethers.
NMR strategy for unraveling structures of bioactive sponge-derived oxy-polyhalogenated diphenyl ethers.
复制标题
DOI：
10.1021/np800737z
复制
发表时间：
2009-03-27
影响因子：
5.1
通讯作者：
Crews, Phillip
中科院分区：
文献类型：
--
作者：
Calcul, Laurent;Chow, Raymond;Oliver, Allen G.;Tenney, Karen;White, Kimberly N.;Wood, Alexander W.;Fiorilla, Catherine;Crews, Phillip
Mcl-1蛋白在癌细胞中的过度表达导致Bak的隔离，而Bak是正常细胞凋亡调节的关键成分。我们对海洋小分子天然产物抑制蛋白质-蛋白质相互作用的能力进行了研究，分离出了几种具有生物活性的氧-多卤代二苯醚。一种半纯的提取物，以前从Dysidea （Lamellodysidea）草本植物中获得并保存在我们的储存库中，与未接触的Dysidea颗粒海绵一起提供13种不同的氧多卤二苯醚。其中有4个新化合物，分别为5、6、10和12。这些分子的结构解析由于文献中存在的过多的结构变体而变得复杂。在反复制过程中，我们建立了一个系统的方法来分析这类化合物。该策略由芳香环的1H和13C NMR位移趋势决定，并通过x射线晶体结构分析验证了该策略的成功。
The over-expression of the Mcl-1 protein in cancerous cells results in the sequestering of Bak, a key component in the regulation of normal cell apoptosis. Our investigation of the ability of marine-derived small molecule natural products to inhibit this protein-protein interaction led to the isolation of several bioactive oxy-polyhalogenated diphenyl ethers. A semi-pure extract, previously obtained from Dysidea (Lamellodysidea) herbacea and preserved in our repository, along with an untouched Dysidea granulosa marine sponge afforded 13 distinct oxy-polyhalogenated diphenyl ethers. Among these isolates were four new compounds, 5, 6, 10, and 12. The structure elucidation of these molecules was complicated by the plethora of structural variants that exist in the literature. During dereplication, we established a systematic method for analyzing this class of compounds. The strategy is governed by trends in the 1H and 13C NMR shifts of the aromatic rings and the success of the strategy was checked by X-ray crystal structure analysis.
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影响因子：
5.1
作者：
Liu, HW;Namikoshi, M;Yao, XS
通讯作者：
Yao, XS
影响因子：
3.6
作者：
ALVI, KA;DIAZ, MC;MORETTI, R
通讯作者：
MORETTI, R
影响因子：
5.1
作者：
FU, XO;SCHMITZ, EJ;CREWS, P
通讯作者：
CREWS, P
影响因子：
1.9
作者：
Hattori, T;Konno, A;Shizuri, Y
通讯作者：
Shizuri, Y
影响因子：
2.1
作者：
Sauleau, P;Retailleau, P;Bourguet-Kondracki, ML
通讯作者：
Bourguet-Kondracki, ML