Objective To investigate the chemical constituents of Fissistigma bracteolatum. Methods The 95% ethanol extract of F. bracteolatum was successively separated by solvent partitioning, macroporous resin, silica gel, MCI, Sephadex LH-20, ODS column chromatography, and semi-preparative HPLC to obtain individual compounds. Their structures were elucidated using modern spectroscopic techniques such as NMR and MS. An in vitro inflammatory model was established using lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages to evaluate the anti-inflammatory activity of the isolated compounds. Results A total of 22 compounds were isolated from F. bracteolatum, comprising of 12 flavonoids, 8 amides, 1 lignan, and 1 lactone. These were determined as: 5,7-dihydroxy-6,8-dimethoxyflavone (1), 5-hydroxy-7,8-dimethoxyflavone (2), quercetin (3), rutin (4), 5,7,8-trimethoxydihydroflavone (5), 5,6,8-trimethoxy-7-hydroxydihydroflavone (6), 6,7-dimethoxy-8-hydroxydihydroflavone (7), (2S)-7-hydroxy-6,8-dimethoxydihydroflavone (8), dihydroquercetin (9), aromadendrin (10), 4,2',6'-trihydroxy-3',4'-dimethoxy- dihydrochalcone (11), 2',6'-dihydroxy-4'-methoxydihydrochalcone (12), N-trans-sinapoylmethoxytyramine (13), N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-phenyl-2-propenamide (14), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-phenethyl-acrylamide (15), N-trans-feruloyltyramine (16), N-trans-p-coumaroyltyramine (17), N-cis-feruloyltyramine (18), cis-N-feruloyl-3-O-methyldopamine (19), cannabisin D (20), 3-caffeoyl-2-methyl-D-erythronic acid-1,4-lactone (21), and (-)-syringaresinol (22). Conclusion Compounds 1, 7, 9—11, 13—15, 17, 19, and 21 were isolated from the genus Fissistigma for the first time.The anti-inflammatory activity results demonstrated that compounds 5 , 9 , 13 , and 16 significantly inhibited the release of nitric oxide in LPS-induced RAW264.7 macrophages.

Annonaceae  /  Fissistigma bracteolatum Chatterjee  /  dihydroquercetin  /  aromadendrin  /  N-trans-feruloyltyramine  /  anti-inflammatory activity