You Jin-Qiu, Jin Yun-Qi, Miao Yu-Meng, Sun Xin-Yu, Yang Jia-Yu, Huang Jin-Chang, Li Jing-Ya, Hou Ai-Jun
Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240, People's Republic of China; Department of Pharmacy, The Fourth Affiliated Hospital of Soochow University, Suzhou Dushu Lake Hospital, Medical Center of Soochow University, Suzhou, 215123, People's Republic of China.
Shanghai Frontiers Science Center of Drug Target Identification and Delivery, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240, People's Republic of China.
Phytochemistry. 2025 Jul;235:114484. doi: 10.1016/j.phytochem.2025.114484. Epub 2025 Mar 17.
Twelve undescribed meroterpenoids possessing bicyclic polyprenylated acylphloroglucinol (BPAP) scaffold, (±)-lancasternoids A-D and lancasternoids E-H, together with fourteen known analogues, were isolated from Hypericum lancasteri (Hypericaceae) and structurally characterized. (±)-Lancasternoids A-D are the first examples of bicyclo[3.2.1]octane-type BPAP meroterpenoids present as enantiomeric pairs, while (±)-lancasternoids A-C incorporate an unprecedented 5-oxatetracyclo[7.5.1.0.0]pentadecane system. Lancasternoids E-H are two pairs of epimers with [3.3.1]-type BPAP scaffold. Some of the isolates showed inhibition in hypoxia-inducible factor-1α (HIF-1α) responsive element (HRE) luciferase assay, and uraloidin A further decreased the lipopolysaccharide (LPS)-induced pro-inflammatory factor IL-1β expression level in RAW 264.7 cells.
从金丝桃属植物兰开斯特金丝桃（金丝桃科）中分离出12个具有双环多异戊二烯基酰基间苯三酚（BPAP）骨架的未描述过的半萜类化合物，即（±）-兰卡甾体A-D和兰卡甾体E-H，以及14个已知类似物，并对其进行了结构表征。（±）-兰卡甾体A-D是作为对映体对存在的双环[3.2.1]辛烷型BPAP半萜类化合物的首个实例，而（±）-兰卡甾体A-C包含一个前所未有的5-氧杂四环[7.5.1.0.0]十五烷体系。兰卡甾体E-H是两对具有[3.3.1]型BPAP骨架的差向异构体。部分分离物在缺氧诱导因子-1α（HIF-1α）反应元件（HRE）荧光素酶测定中表现出抑制作用，乌拉洛丁A还降低了脂多糖（LPS）诱导的RAW 264.7细胞中促炎因子白细胞介素-1β的表达水平。
