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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.