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Monoterpene esters and aporphine alkaloids from Illigera aromatica with inhibitory effects against cholinesterase and NO production in LPS-stimulated RAW264.7 macrophages

Dong, Jian-Wei, Cai, Le, Li, Xue-Jiao, Wang, Jia-Peng, Mei, Rui-Feng, Ding, Zhong-Tao
Archives of pharmacal research 2017 v.40 no.12 pp. 1394-1402
acetylcholinesterase, alkaloids, carvacrol, chemical structure, cholinesterase, circular dichroism spectroscopy, enzyme inhibition, esters, herbal medicines, inhibitory concentration 50, macrophages, monoterpenoids, nitric oxide, nuclear magnetic resonance spectroscopy, styrene, tubers
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 IC₅₀ value of 18.71 ± 0.85 μM; compound 1, 3, and 4 showed moderate butyrylcholinesterase inhibitory activities with the IC₅₀ values 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 IC₅₀ value of 81.69 ± 2.07 μM, and compounds 5 and 6 possessed moderate AChE inhibitory activities with the IC₅₀ values 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.