[关键词]
[摘要]
目的 研究排骨灵Fissistigma bracteolatum化学成分。方法 排骨灵95%乙醇提取总浸膏经萃取、大孔树脂、硅胶、MCI、凝胶、ODS等柱色谱以及半制备液相进行分离与纯化。利用波谱技术等现代光谱技术对结构进行解析鉴定。并构建脂多糖(lipopolysaccharide,LPS)诱导的RAW264.7细胞体外炎症模型,对分离得到的化合物进行体外抗炎活性评价。结果 从排骨灵中分离得到22个化合物,其中12个黄酮类,8个酰胺类、1个木脂素类和1个内酯类。分别鉴定为5,7-二羟基-6,8-二甲氧基黄酮(1)、5-羟基-7,8-二甲氧基黄酮(2)、槲皮素(3)、芦丁(4)、5,7,8-三甲氧基二氢黄酮(5)、5,6,8-三甲氧基-7-羟基二氢黄酮(6)、6,7-二甲氧基-8-羟基二氢黄酮(7)、2S-7-羟基-6,8-二甲氧基二氢黄酮(8)、双氢槲皮素(9)、香橙素(10)、4,2',6'-三羟基-3',4'-二甲氧基二氢查耳酮(11)、2',6'-二羟基-4'-甲氧基二氢查耳酮(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-反式-阿魏酰基酪胺(16)、N-反式-对香豆酰酪胺(17)、N-cis-feruloyltyramine(18)、cis-N-feruloyl-3-O-methyldopamine(19)、cannabisin D(20)、3-咖啡酸酰基-2-甲基-D-赤藓糖酸-1,4-内酯(21)、(-)-syringaresinol(22)。结论 化合物1、7、9~11、13~15、17、19、21均为首次从瓜馥木属中分离得到。抗炎活性结果表明化合物5、9、13、16能明显抑制LPS诱导的RAW264.7巨噬细胞释放一氧化氮的释放。
[Key word]
[Abstract]
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.
[中图分类号]
R284.1
[基金项目]
河南省优秀青年基金资助项目(252300421137);河南省科学技术研究发展计划联合基金项目(242301420109);河南省高校科技创新团队支持计划(24IRTSTHN039);河南省科技攻关项目(242102310520);河南省高校重点科研项目(25A360024);大学生创新创业训练计划项目(202410471008)