ABSTRACT
Repeated column chromatography resulted in the isolation of two new glycosides, miliusides A-B (1 and 7), along with six known metabolites (2-6, and 8) from the leaves of Miliusa sinensis Finet and Gagnep. The structures of the purified phytochemicals were elucidated by interpreting their spectroscopic data (NMR, HRMS), as well as comparison with the previous literature. The biological evaluation of acetylcholinesterase (AChE) inhibitory effects and anti-inflammatory activity by measuring nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 mouse macrophage cells, were also conducted. Among them, compounds 5 and 7 exhibited significant AChE inhibitory activities (IC50 = 53.36 ± 4.20 and 88.50 ± 8.79 µM, respectively), compared with the positive control (Galanthamine, IC50 = 1.65 ± 0.15 µM). Only the MeOH extract showed suppression effects on NO production in LPS-induced RAW264.7 cells (IC50 = 38.18 ± 3.25 µg/mL) comparable to that of the positive control, l-NMMA (IC50 = 2.21 ± 0.56 µg/mL).
Subject(s)
Annonaceae , Cardiac Glycosides , Mice , Animals , Glycosides/pharmacology , Glycosides/chemistry , Lipopolysaccharides/pharmacology , Acetylcholine , Acetylcholinesterase , Plant Extracts/pharmacology , Plant Extracts/chemistry , Annonaceae/chemistry , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Nitric Oxide , RAW 264.7 CellsABSTRACT
The n-hexane extract of Knema pachycarpa fruits (Myristicaceae family), exhibiting strong anti-acetylcholinesterase activity, was investigated by gas chromatography/mass spectrometry and then purified by column chromatography. Guided by GC/MS profiling and bioassay, chromatographic separations led to the isolation of five new compounds: two anacardic acid derivatives 1-2, two cardanol derivatives 3-4 and a cardol derivative 5, along with mixtures of known phenolic lipids 6-9. The chemical structures were determined by various spectroscopic methods. New isolated compounds 1-5 were evaluated for their cytotoxicity and anti-acetylcholinesterase activity. Cardanol 3 and cardol 5 were the most active compounds in the acetylcholinesterase inhibitory assay with IC50 values of 2.60 ± 0.24 µM and 2.46 ± 0.23 µM, respectively. Cardanol 4 and cardol 5 showed moderate cytotoxicity against Hela and MCF-7 cancer cell lines with IC50 values ranging from 31.36 ± 0.41 µM to 41.30 ± 2.49 µM.