Cadinane Sesquiterpenoids and Their Glycosides from Alangium chinense That Inhibit Spontaneous Calcium Oscillations
Cadinane Sesquiterpenoids and Their Glycosides from Alangium chinense That Inhibit Spontaneous Calcium Oscillations
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八角枫中抑制自发钙振荡的卡地烷倍半萜类化合物及其糖苷
DOI：
10.1021/acs.jnatprod.1c00978
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发表时间：
2021
影响因子：
5.1
通讯作者：
Zhengyu Cao
中科院分区：
文献类型：
--
作者：
Chunlei Zhang;Ju Liu;Chuchu Xi;Yangang Cao;Jing He;Shucong Li;Fan Zhang;C. Benjamin Naman;Zhengyu Cao
从八角枫（Alangium chinense）叶中分离出九个新的杜松烷型倍半萜类化合物，alanenses A-I（1-9）以及三个先前报道的类似物（10-12）。通过光谱和光谱数据的解释阐明了这些分子的结构。绝对配置建立了比较实验和计算的ECD数据，化学降解研究糖部分，和单晶X-射线衍射分析。化合物1和2以外消旋体形式分离，并通过手性HPLC实现对映体纯化。化合物3 - 5是带有β-d-葡萄糖单元的糖基化的杜松烷，而化合物6 - 9以游离形式或另外的环融合形式掺入羟甲基。化合物11的结构最初被错误指定，后来使用额外的NMR数据进行了修订。修正后的结构在此得到了X射线单晶分析的支持。化合物1和2在低微摩尔浓度下抑制自发钙通道振荡。
Nine new cadinane sesquiterpenoids, alanenses A–I (1–9), were isolated from the leaves ofAlangium chinensetogether with three previously reported analogues (10–12). The structures of these molecules were elucidated by interpretation of spectroscopic and spectrometric data. Absolute configurations were established by the comparison of experimental and calculated ECD data, chemical degradation studies for sugar moieties, and a single-crystal X-ray diffraction analysis. Compounds1and2were isolated as racemates, and enantiopurification was achieved by chiral HPLC. Compounds3–5are glycosylated cadinanes bearing a β-d-glucose unit, while compounds6–9incorporate a hydroxymethyl group in either the free form or additional ring fusion. The structure of compound11was originally misassigned and later revised using additional NMR data. The corrected structure is here supported by X-ray single-crystal analysis. Compounds1and2inhibit spontaneous calcium channel oscillations at low micromolar concentrations.