Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
Bioorg Chem. 2020 Nov;104:104275. doi: 10.1016/j.bioorg.2020.104275. Epub 2020 Sep 11.
Acylphloroglucinol meroterpenoids are adducts of the acylphloroglucinol unit and polyprenylated fragments (terpenoids) with attractive structures and bioactivities. During study of the medicinal molecules of the genus Hypericum, the first example of dimethylated acylphloroglucinol meroterpenoids with pyran-fused 6/6/6 tricyclic skeletons ((+)/(-)-elodeoidols A-F (1-6)), along with three biogenetical homologues (7-9) were isolated from the herbaceous plant of Hypericum elodeoides. Their structures including absolute configurations were then identified by nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), electronic circular dichroism (ECD) analysis and calculations. The monoterpene moiety of 1-6 were cyclized as two cyclohexanes and fused with a dimethylated acylphloroglucinol unit through an additional ether linkage, which led to an interesting pyran-fused linear or angle type 6/6/6 tricyclic skeleton. Compounds 5, 8 and 9 showed preferable antibacterial activities against three oral bacteria, among the MIC value of (+)-5 was 6.25 μg/ml; Compounds 3, 7 and 8 exhibited significant NO inhibitory activity against LPS induced RAW264.7 cells (IC: 10.39 ± 0.49 ~ 34.25 ± 2.32 μM).
酰基间苯三酚倍半萜是酰基间苯三酚单元与多聚异戊烯片段（萜类化合物）的加合物，具有吸引人的结构和生物活性。在研究贯叶连翘属药用分子的过程中，首次从草本贯叶连翘植物中分离得到具有吡喃并合 6/6/6 三环骨架的二甲酰基间苯三酚倍半萜类化合物（(+)/(-)-艾洛醇 A-F(1-6)），以及三个生物同源物（7-9）。通过核磁共振（NMR）、高分辨率电喷雾电离质谱（HRESIMS）、电子圆二色性（ECD）分析和计算，确定了它们的结构包括绝对构型。1-6 的单萜部分环化形成两个环己烷，并通过额外的醚键与二甲酰基间苯三酚单元融合，形成有趣的吡喃并合线性或角型 6/6/6 三环骨架。化合物 5、8 和 9 对三种口腔细菌表现出较好的抗菌活性，其中(+)-5 的 MIC 值为 6.25μg/ml；化合物 3、7 和 8 对 LPS 诱导的 RAW264.7 细胞具有显著的 NO 抑制活性（IC：10.39±0.49~34.25±2.32μM）。
