title: Proaporphine and aporphine alkaloids with acetylcholinesterase inhibitory activity from Stephania epigaea.
abstract: An unusual proaporphine alkaloid bearing an isopropanenitrile group at isoquinoline nitrogen, named epiganine A (1) and a new aporphine alkaloid, epiganine B (2), together with eight known alkaloids, pronuciferine (3), dehydrodicentrine (4), romerine (5), romeline (6), N-methylcalycinine (7), phanostenine (8), dicentrine (9), and N-methyllaurotetanine (10), were isolated from the roots of Stephania epigaea. The absolute configuration of 1 was determined by calculating electronic circular dichroism (ECD) and comparing with experimental data. Compounds 2 and 4 showed strong acetylcholinesterase (AChE) inhibitory effects with the IC50 values of 4.36 and 2.98μM, respectively. Compounds 5-9 also exhibited potent AChE inhibitory activities.
authors.affiliation: Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Jian-Wei
authors.initials: JW
authors.lastname: Dong
authors.affiliation: Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Le
authors.initials: L
authors.lastname: Cai
authors.affiliation: Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Yun-Shan
authors.initials: YS
authors.lastname: Fang
authors.affiliation: Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China; School of Pharmaceutical Sciences and Chemistry, Dali University, Dali 671000, PR China.
authors.forename: Huai
authors.initials: H
authors.lastname: Xiao
authors.affiliation: Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
authors.forename: Zhen-Jie
authors.initials: ZJ
authors.lastname: Li
authors.affiliation: Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China. Electronic address: ztding@ynu.edu.cn.
authors.forename: Zhong-Tao
authors.initials: ZT
authors.lastname: Ding
mesh_terms: D001060:Aporphines / Q000737:chemistry* / Q000302:isolation & purification; D002800:Cholinesterase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry*; D031607:Stephania / Q000737:chemistry*
chemical_list: D001060:Aporphines; D002800:Cholinesterase Inhibitors; C081279:aporphine
keywords: Acetylcholinesterase inhibitory activity; Aporphine alkaloid; Dehydrodicentrine (PubChem CID: 3084326); Dicentrine (PubChem CID: 101300); Epiganine A; Epiganine B; N-methylcalycinine; N-methyllaurotetanine (PubChem CID: 16573); Phanostenine (PubChem CID: 12305138); Proaporphine alkaloid; Pronuciferine (PubChem CID: 200480); Romeline; Romerine (PubChem CID: 119204); Stephania epigaea