New norlignan enantiomers from the fruit of Crataegus pinnatifida with neuroprotective activities  

作　　者：Rui Guo Tianming Lv Fengying Han Zilin Hou Guodong Yao Bin Lin Xiaobo Wang Xiaoxiao Huang Shaojiang Song 

机构地区：[1]Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research&Development,Liaoning Province,School of Traditional Chinese Materia Medica,Shenyang Pharmaceutical University,Shenyang 110016,China [2]School of Pharmaceutical Engineering,Shenyang Pharmaceutical University,Shenyang 110016,China [3]Chinese People's Liberation Army Logistics Support Force No.967 Hospital,Dalian 116021,China

出　　处：《Chinese Chemical Letters》2020年第5期1254-1258,共5页中国化学快报（英文版）

基　　金：supported by Career Development Support Plan for Young and Middle-aged Teachers in Shenyang Pharmaceutical University(No.ZQN2018006);the Project of Innovation Team Foundation(No.LT2015027)。

摘　　要：(±)-Crataegusnorin A(la/1b) and B(2a/2b),two pairs of rare 8,9’-epoxy-type norlignan enantiomers featuring a y-butyrolactone ring,were isolated from the fruit of Crataegus pinnatifida.Their structures were determined via extensive spectroscopic analyses.Gauge-independent atomic orbital(GIAO) NMR chemical shift calculations,combined with the advanced statistical method DP4+were employed to establish the relative configurations of four compounds.Next,chiral separation was accomplished by chiral chromatographic column and the absolute configurations of the four compounds were unambiguously assigned by comparison between their experimental electronic circular dichroism curves with the quantum-mechanically calculated curves based on time-dependent density functional theory(TDDFT).All the isolates were evaluated fo r their neuroprotective activities against H2O2-induced cell injury in human neuroblastoma SH-SY5Y cells.The results showed that two pairs of enantiomers 1a/1b and 2a/2b displayed diff;erent effect on neuroprotective activity.Among them,compound 2a displayed the most potent neuroprotective effect Further flow cytometry analysis indicated that 2a could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis.

关 键 词：Crataegus pinnatifida Norlignan enantiomer Neuroprotective activity SH-SY5Y cells Apoptosis 

分 类 号：R285[医药卫生—中药学]