Norsampsone E, an unprecedented decarbonyl polycyclic polyprenylated acylphloroglucinol with a homoadamantyl core from Hypericum sampsonii
Norsampsone E, an unprecedented decarbonyl polycyclic polyprenylated acylphloroglucinol with a homoadamantyl core from Hypericum sampsonii
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Norsampsone E，一种前所未有的脱羰基多环聚异戊二烯化酰基间苯三酚，具有来自金丝桃的同金刚烷基核心
DOI：
10.1039/c7ra05947g
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发表时间：
2017-01-01
期刊：
影响因子：
3.9
通讯作者：
Yao, Xin-Sheng
中科院分区：
文献类型：
--
作者：
Tian, Wen-Jing;Qiu, Yu-Qin;Yao, Xin-Sheng
从金丝桃地上部分分离得到一个未见文献报道的去羰基多环聚异戊二烯酰基间苯三酚衍生物Norsampsone E（1），以及一个新的和两个已知的类似物（2-4）。化合物1具有不寻常的同金刚烷基骨架，失去了C-4羰基，随后在C-3和C-5之间形成了新的C-C键。通过广泛的核磁共振光谱、单晶X射线实验、ECD计算和CD比较方法阐明了它们的结构和绝对构型，并使用生物遗传相关同系物3和4的单晶X射线结构进一步证实。此外，化合物1和2在SPR测定中显示与RXRa-LBD蛋白直接结合，K-D分别为10.28 μ M和31.70 μ M。此外，化合物1（5-20 mM）以剂量依赖性方式显示有效的RXR α转录抑制活性，而化合物2（5-20 μ M）略微增强RXR α反式激活。
Norsampsone E (1), an unprecedented decarbonyl polycyclic polyprenylated acylphloroglucinol, together with one new and two known analogues (2-4), was isolated from the aerial parts of Hypericum sampsonii. Compound 1 featured an unusual homoadamantyl skeleton with the loss of C-4 carbonyl and followed by the formation of a new C-C bond between C-3 and C-5. Their structures and absolute configurations were elucidated by extensive NMR spectroscopy, single-crystal X-ray experiments, ECD calculations and CD comparison methods, and further confirmed using the single-crystal X-ray structures of biogenetically related congeners 3 and 4. Besides, compounds 1 and 2 showed direct binding to the RXRa-LBD protein in the SPR assay with a K-D of 10.28 mu M and 31.70 mu M, respectively. Furthermore, compound 1 (5-20 mM) showed potent RXRa transcriptional inhibitory activity in a dose dependent manner, while compound 2 (5-20 mu M) slightly enhanced RXRa transactivation.