title: Monoterpene esters and aporphine alkaloids from Illigera aromatica with inhibitory effects against cholinesterase and NO production in LPS-stimulated RAW264.7 macrophages.
abstract: Three new monoterpene phenylpropionic acid esters, illigerates A-C (1-3), and one new aporphine alkaloid, illigeranine (4), as well as four known ones, actinodaphnine (5), nordicentrine (6), 8-hydroxy carvacrol (7), and 3-hydroxy-α,4-dimethyl styrene (8), were isolated from the tubers of Illigera aromatica. The structures of 1-4 were identified by HRESIMS, 1D and 2D NMR, and electronic circular dichroism spectra. Compound 1 potently inhibited NO production in LPS-stimulated RAW264.7 cells with an IC50value of 18.71 ± 0.85 μM; compound 1, 3, and 4 showed moderate butyrylcholinesterase inhibitory activities with the IC50values of 46.86 ± 0.65, 53.51 ± 0.71, and 31.62 ± 1.15 μM, respectively. Compound 4 showed weak AChE inhibitory activity with an IC50value of 81.69 ± 2.07 μM, and compounds 5 and 6 possessed moderate AChE inhibitory activities with the IC50values of 47.74 ± 1.66 and 40.28 ± 2.73 μM, respectively. This paper provides a chemical structure and bioactive foundation for using I. aromatica as an herbal medicine.
authors.affiliation: School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China.
authors.forename: Jian-Wei
authors.initials: JW
authors.lastname: Dong
authors.affiliation: School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China. caile@ynu.edu.cn.
authors.forename: Le
authors.initials: L
authors.lastname: Cai
authors.affiliation: School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China.
authors.forename: Xue-Jiao
authors.initials: XJ
authors.lastname: Li
authors.affiliation: School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China.
authors.forename: Jia-Peng
authors.initials: JP
authors.lastname: Wang
authors.affiliation: School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China.
authors.forename: Rui-Feng
authors.initials: RF
authors.lastname: Mei
authors.affiliation: School of Chemical Science and Technology, Yunnan University, Kunming, 650091, People's Republic of China. ztding@ynu.edu.cn.
authors.forename: Zhong-Tao
authors.initials: ZT
authors.lastname: Ding
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D000818:Animals; D001060:Aporphines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002091:Butyrylcholinesterase / Q000378:metabolism; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004952:Esters / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D049935:Hernandiaceae / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009569:Nitric Oxide / Q000096:biosynthesis / Q000378:metabolism*; D011789:Quantum Theory; D000067996:RAW 264.7 Cells; D013329:Structure-Activity Relationship
chemical_list: D001060:Aporphines; D002800:Cholinesterase Inhibitors; D004952:Esters; D008070:Lipopolysaccharides; D039821:Monoterpenes; C081279:aporphine; D009569:Nitric Oxide; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase
keywords: Anti-inflammatory activity; Aporphine alkaloid; Cholinesterase inhibitory activity; Illigera aromatica; Monoterpene ester