Molecular networking-based discovery of anti-inflammatory chromene dimers from Melicope pteleifolia
Molecular networking-based discovery of anti-inflammatory chromene dimers from Melicope pteleifolia
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DOI：
10.1016/j.phytochem.2022.113322
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发表时间：
2022-08-03
期刊：
影响因子：
3.8
通讯作者：
Mitsunaga, Tohru
中科院分区：
文献类型：
--
作者：
Kakumu, Yuya;Nguyen, Minh Tu Thi;Mitsunaga, Tohru
借助基于特征的分子网络策略，从Melicope pteleifolia的叶子中分离出五个未描述的C-2和C-1对称色烯二聚体，即melptelchromenes A-E。发现四种不对称二聚体是外消旋体，并通过手性相 HPLC 分析进行了解析。它们的结构，包括绝对构型，通过 HRMS、NMR 光谱以及 ECD 光谱和 NMR 化学位移的量子力学计算来阐明。 Melptelchromene A-D 通过两个 2H-色烯核心具有独特的亚乙基键，而 Melptelchromene E 代表了具有 1,3-二芳基丁-1-醇部分的二聚色烯的第一个例子。在这些化合物中，6,6'-连接的二聚色烯对脂多糖诱导的RAW 264细胞显示出一氧化氮抑制活性，并且(-)-和(+)-melptelchromene E是两种最有效的化合物（IC50分别为3.0和5.1μM）。
With the aid of a feature-based molecular networking strategy, five undescribed C-2 and C-1 symmetric chromene dimers, namely, melptelchromenes A-E, were isolated from the leaves of Melicope pteleifolia. Four asymmetric dimers were found to be racemates and were resolved by chiral phase HPLC analyses. Their structures, including absolute configurations, were elucidated by HRMS, NMR spectroscopy, and quantum mechanical calculations of ECD spectra and NMR chemical shifts. Melptelchromenes A-D possess a unique ethylidene linkage via two 2H-chromene cores, while melptelchromene E represents the first example of a dimeric chromene featuring a 1,3-diarylbutan-1-ol moiety. Of these compounds, 6,6'-linked dimeric chromenes showed nitric oxide inhibitory activities on lipopolysaccharide-induced RAW 264 cells, and (-)- and (+)-melptelchromene E were the two most potent compounds (IC50, 3.0 and 5.1 mu M, respectively).