[关键词]
[摘要]
目的 研究毛相思子Abrus mollis去除荚果后的干燥全草(毛鸡骨草)的化学成分及其体外抗炎活性。方法 综合运用硅胶、ODS反相柱色谱和半制备高效液相色谱等方法进行分离纯化,根据高分辨质谱,核磁共振波谱数据以及与文献对比进行结构鉴定,通过电子圆二色谱(electronic circular dichroism,ECD)数据分析确定化合物1和2的绝对构型。采用Griess法测定化合物对脂多糖(lipopolysaccharide,LPS)诱导的小鼠RAW264.7巨噬细胞产生一氧化氮(NO)的抑制活性。结果 从毛鸡骨草甲醇提取物中分离得到12个化合物,分别鉴定为 (αR)-α,4,2ʹ,4ʹ-四羟基-3-甲氧基二氢查耳酮(1)、(αR)-α,4,2ʹ,4ʹ-tetrahydroxydihydrochalcone(2)、(+)-甘草素(3)、mucunone C(4)、(+)-medicarpin(5)、abrusprecatin A(6)、7,4'-dihydroxy-8-methoxyisoflavone(7)、7,3'-dihydroxy-6,4'-dimethoxyisoflavone(8)、7,3'-dihydroxy-8,4'-dimethoxyisoflavone(9)、alopecuroides A(10)、hypaphorine(11)、7,8-二甲苯基蝶啶-2,4-(1H,3H)-二酮(12)。化合物3、4、7和10对LPS诱导的RAW264.7细胞NO生成有抑制作用,半数抑制浓度(median inhibition concentration,IC50)值为7.39~20.09 μmol/L,其中化合物7对NO生成的抑制活性相对较好,IC50值为7.39 μmol/L。结论 化合物1为1个新的二氢查耳酮,命名为毛鸡骨草素;化合物2和10为首次从相思子属植物中分离得到。化合物3、4、7和10具有潜在的抗炎活性。
[Key word]
[Abstract]
Objective To study the chemical constituents of Maojigucao (Abrus mollis Hance) and their anti-inflammatory activities. Methods The chemical constituents were isolated and purified by silica gel, ODS reversed-phase column chromatography, as well as semi-preparative RP-HPLC. Their structures were established by HR-ESI-MS, NMR data analyses and literature data comparison. The absolute configurations of compounds 1 and 2 were determined based on ECD data analyses. The inhibitory effects of all compounds against nitirc oxide (NO) production in lipopolysaccharide (LPS)-induced mouse RAW264.7 macrophage cells were evaluated by Griess assay. Results A total of 12 compounds were isolated from the methanol extract of A. mollis, their structures were identified as (αR)-α,4,2ʹ,4ʹ-tetrahydroxy-3-methoxydihydrochalcone (1), (αR)-α,4,2ʹ,4ʹ-tetrahydroxy- dihydrochalcone (2), (+)-liquiritigenin (3), mucunone C (4), (+)-medicarpin (5),abrusprecatin A (6), 7,4'-dihydroxy-8-methoxyisoflavone (7), 7,3'-dihydroxy-6,4'-dimethoxyisoflavone (8), 7,3'-dihydroxy-8,4'-dimethoxyisoflavone (9), alopecuroides A (10), hypaphorine (11), 7,8-dimethylbenzo[g]pteridine-2,4-(1H,3H)-dione (12). Compounds 3, 4, 7 and 10 exerted inhibitory effects on NO production with IC50values ranging from 7.39 to 20.09 μmol/L in LPS-stimulated RAW264.7 cells, of which compound 7 had the best inhibitory activity of 7.39 μmol/L. Conclusion Compound1 was a new dihydrochalcone, named as abrusin M, and compounds 2 and 10 were isolated from Abrus genus for the first time. Compounds 3,4, 7 and 10 exhibited potential anti-inflammatory activities.
[中图分类号]
R284.1
[基金项目]
广西中医药大学-柳药集团青年科技创新能力提升计划专项(YXY0000305);国家自然基金委区域联合基金重点项目(U23A20521)