Investigation of the alkaloids from Myrioneuron faberi, a plant unique to China, gave four pairs of enantiomers (1-4). (+/-)-beta-Myrifabral A (1) and (+/-)-alpha-myrifabral A (2) formed an inseparable mixture of anomers (duster A), as did (+/-)-beta-myrifabral B (3) and (+/-)-alpha-myrifabral B (4) (cluster B). Their structures were determined by X-ray diffraction and NMR analysis. Compounds 1-4 possessed novel cyclohexane-fused octahydroquinolizine skeletons and represent the first quinolizidine alkaloids from the genus Myrioneuron. The epimers of cluster A (1 and 2) were modified and separated. In vitro, clusters A and B and their derivatives inhibited replication of hepatitis C virus (HCV, IC50 0.9 to 4.7 mu M) with cytotoxicity lower than that of telaprevir.
1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China 3.Chinese Acad Med Sci, Inst Med Biotechnol, Beijing 10050, Peoples R China 4.Peking Union Med Coll, Beijing 10050, Peoples R China 5.Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
Cao,Ming-Ming;Zhang,Yu;Li,Xiao-Hui;Peng,Zong-Gen;Jiang,Jian-Dong;Gu,Yu-Cheng;Di,Ying-Tong;Li,Xiao-Nian;Chen,Duo-Zhi;Xia,Cheng-Feng;He,Hong-Ping;Li,Shun-Lin;Hao,Xiao-Jiang.Cyclohexane-Fused Octahydroquinolizine Alkaloids from Myrioneuron faberi with Activity against Hepatitis C Virus,JOURNAL OF ORGANIC CHEMISTRY,2014,79(17):7945-7950