Proaporphine and aporphine alkaloids with acetylcholinesterase inhibitory activity from Stephania epigaea

Jian-Wei Dong; Le Cai; Yun-Shan Fang; Huai Xiao; Zhen-Jie Li; Zhong-Tao Ding

doi:10.1016/j.fitote.2015.05.019

Proaporphine and aporphine alkaloids with acetylcholinesterase inhibitory activity from Stephania epigaea

Fitoterapia. 2015 Jul:104:102-7. doi: 10.1016/j.fitote.2015.05.019. Epub 2015 May 29.

Authors

Jian-Wei Dong¹, Le Cai¹, Yun-Shan Fang¹, Huai Xiao², Zhen-Jie Li¹, Zhong-Tao Ding³

Affiliations

¹ Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, PR China.
² 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.
³ 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.

PMID: 26028544
DOI: 10.1016/j.fitote.2015.05.019

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.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aporphines / chemistry*
Aporphines / isolation & purification
Cholinesterase Inhibitors / chemistry*
Cholinesterase Inhibitors / isolation & purification
Inhibitory Concentration 50
Molecular Structure
Plant Roots / chemistry*
Stephania / chemistry*

Substances

Aporphines
Cholinesterase Inhibitors
aporphine