文献类型：期刊文献

英文题名：(-) and (+)-Merrilliaquinone, a pair of new quinone enantiomers from Illicium merrillianum and their distinctive effect on human hepatoma and hepatic cells

作者：Tian, Xinhui[1];Li, Li[2,3];Pei, Jinpeng[4];Yue, Rongcai[1];Fang, Xin[1];Zhang, Jianping[1];He, Weiwei[4];Shan, Lei[1];Shen, Yunheng[1];Zhang, Weidong[1,4,5]

机构：[1]Second Mil Med Univ, Sch Pharm, Dept Phytochem, Shanghai 200433, Peoples R China;[2]Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China;[3]Peking Union Med Coll, Beijing 100050, Peoples R China;[4]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[5]Shanghai Inst Pharmaceut Ind, Innovat Res Ctr Tradit Chinese Med, Shanghai 200040, Peoples R China

年份：2015

卷号：5

期号：93

起止页码：75857

外文期刊名：RSC ADVANCES

收录：;EI(收录号：20153801280439);WOS:【SCI-EXPANDED(收录号:WOS:000361387300003)】；

基金：The work was supported by the following programs: NSFC (81373301, 81230090, 1302658), Shanghai Leading Academic Discipline Project (B906), Shanghai Engineering Research Center for the Preparation of Bioactive Natural Products (10DZ2251300), Scientific Foundation of Shanghai, China (12401900801, 13401900101) and the National Key Technology R&D Program of China (2012BAI29B06).

语种：英文

外文关键词：Chirality - Enantiomers - Spectroscopic analysis - Cell culture - Quantum theory - Mitochondria - Cell death - Cell membranes

摘要：Merrilliaquinone (1), a new racemic quinone was isolated from the branches and leaves of Illicium merrillianum. Chiral separation of 1 gave two enantiomers (-)-merrilliaquinone (1a) and (+)-merrilliaquinone (1b). The structure of 1 was established by comprehensive spectroscopic analysis, and the absolute configurations of 1a and 1b were determined by quantum mechanical calculation of ECD spectra. It is very interesting that 1b had a selective cytotoxicity against human hepatoma cell lines SMMC7721 and HuH7 with IC50 values of 0.91 mu M and 1.29 mu M, while its IC50 values on normal human hepatic cells QSG7701 and LO2 were 47.79 mu M and 36.71 mu M, respectively. Moreover, 1a and racemate 1 only exhibited very weak cytotoxicity against SMMC7721 and HuH7 cells with IC50 values of 27.01-37.82 mu M. These results implied that the absolute configurations of 1a and 1b possess remarkable influences on their cytotoxicities. Further mechanism studies indicated that 1b dose-dependently induced SMMC7721 cell apoptosis and reduction of mitochondrial membrane potential (MMP) at 1-10 mu M. Flow cytometry analysis showed that the 1b-induced SMMC7721 cell apoptosis was associated with cell cycle arrest during the G(0)/G(1) phase.