Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy , China Pharmaceutical University , 24 Tong Jia Xiang , Nanjing 210009 , People's Republic of China.
J Nat Prod. 2019 Jun 28;82(6):1399-1404. doi: 10.1021/acs.jnatprod.8b00003. Epub 2019 Apr 18.
A synthesis-inspired chemical investigation of the leaves of Melicope ptelefolia led to the isolation of evodialones A-D (1-4), four rearranged acetophenone stereoisomers possessing a prenylated acylcyclopentenone skeleton with three stereogenic carbons. Evodialones C and D (3 and 4) are new minor constituents. The chiral-phase HPLC resolution gave (+)-1-4 and (-)-1-4, eight enantiomers forming a complete stereoisomer library. Their absolute configurations were elucidated via extensive spectroscopic data and a modified Mosher's method. The relationship between the chiral structures and their NMR and ECD data is discussed. Compounds (±)-1, -2, and -4 have significant protective effects on high-glucose-induced oxidative stress in human vein endothelial cells.
受合成启发，对桃金娘科白千层属植物叶进行了化学研究，从中分离得到了吴茱萸内酯 A-D（1-4），这四个具有prenylated acylcyclopentenone 骨架的乙酰苯酮立体异构体，骨架上有三个手性碳原子。吴茱萸内酯 C 和 D（3 和 4）是新的次要成分。手性相高效液相色谱拆分得到了 (+)-1-4 和 (-)-1-4，八种对映异构体形成了完整的立体异构体库。通过广泛的光谱数据和改进的 Mosher 法确定了它们的绝对构型。讨论了手性结构与其 NMR 和 ECD 数据之间的关系。化合物（±）-1、-2 和 -4 对人静脉内皮细胞高葡萄糖诱导的氧化应激具有显著的保护作用。
