[关键词]
[摘要]
目的 研究红芪Hedysari Radix 的化学成分及其抗炎活性。方法 采用硅胶、ODS、HPLC等色谱技术以及重结晶等方法进行分离纯化,运用MS、NMR等波谱方法并结合文献数据,对化合物结构进行鉴定,采用脂多糖诱导的RAW264.7小鼠单核巨噬细胞体外炎症模型进行抗炎活性评价。结果 从红芪醋酸乙酯部位共分离得到47个化合物,分别鉴定为大豆苷元(1)、毛蕊异黄酮(2)、芒柄花素(3)、6''-O-乙酰基芒柄花苷(4)、6,3'-二甲氧基-7,5'-二羟基异黄酮(5)、7,4'-二羟基黄酮(6)、(-)-美迪紫檀素(7)、11b-羟基-11b,1-二氢美迪紫檀素(8)、硫黄菊素(9)、对羟基肉桂酸(10)、3,4-二甲氧基肉桂酸(11)、3,4,5-三甲氧基肉桂酸(12)、3,4,5-三甲氧基肉桂酸甲酯(13)、阿魏酸(14)、阿魏酸甲酯(15)、阿魏酸十六醇酯(16)、阿魏酰氧基棕榈酸甲酯(17)、阿魏酸亚油酯(18)、阿魏酸油酯(19)、阿魏酸二十八醇酯(20)、E-p-香豆醇乙醚(21)、5-烯丙基-2,3-二甲氧基苯酚(22)、(-)-丁香脂素(23)、(-)-去氢双松柏醇(24)、(-)-蛇菰宁(25)、霉酚酸(26)、霉酚酸甲酯(27)、β-谷甾醇(28)、β-谷甾醇棕榈酸酯(29)、豆甾-4-烯-3-酮(30)、白桦脂醇(31)、白桦脂酸(32)、羽扇豆醇(33)、对羟基苯甲醛(34)、对羟基苯甲酸(35)、对羟基苯甲酸甲酯(36)、香草醛(37)、香草酸(38)、3,4,5-三甲氧基苯甲酸(39)、硬脂酸(40)、硬脂酸甲酯(41)、单棕榈酸甘油酯(42)、尿嘧啶(43)、烟酰胺(44)、(-)-2-(2-羟基丙酰胺基)苯甲酰胺(45)、对苯二甲酸二丁酯(46)、脱落酸(47)。在抗炎活性评价实验中,化合物6、7、9、14、21、24、25、46对NO生成具有抑制作用。结论 首次从红芪中分离得到31个化合物,分别是化合物1、4、5、8~12、15、17~22、24~27、29~31、34~37、39、44~47,其中,化合物17为首次从自然界分离得到,对其核磁数据进行了补充;此外,化合物7、24、25对NO具有显著抑制作用,与阳性对照槲皮素(20 µg/mL)相比,具有较好的抗炎活性。
[Key word]
[Abstract]
Objective To investigate the chemical constituents and anti-inflammatory activity of Hedysari Radix. Methods Separation and purification were carried out using chromatographic techniques such as silica gel, ODS, HPLC and recrystallization. The structure of the compounds was identified using spectroscopic methods such as MS and NMR and in combination with literature data, and anti-inflammatory activity was evaluated using the lipopolysaccharide induced in vitro inflammatory model of RAW264.7 mouse monocyte-macrophage cells. Results A total of 47 chemical constituents were isolated and identified from ethyl acetate site of Hedysari Radix, namely: daidzein (1), calycosin (2), formononetin (3), 6''-O-acetylononin (4), 6,3'-dimethoxy-7,5'-dihydroxyisoflavone (5), 4',7-dihydroxyflavone (6), (-)-medicarpin (7), 11b-hydroxy-11b,1-dihydromedicarpin (8), sulfurein (9), p-coumaric acid (10), 3,4-dimethoxycinnamic acid (11), 3,4,5-trimethoxycinnamic acid (12), methyl 3,4,5-trimethoxycinnamate (13), ferulic acid (14), methyl ferulate (15), hexadecyl ferulate (16), methyl ω-feruloyloxypalmitate (17), linoleyl ferulate (18), oleyl ferulate (19), octacosanol ferulate (20), E-p-coumaryl alcohol γ-O-methyl ether (21), 5-allyl-2,3-dimethoxyphenol (22), (-)-syringaresinol (23), (-)-dehydrodiconiferyl alcohol (24), (-)-balanophonin (25), mycophenolic acid (26), methyl mycophenolate (27), β-sitosterol (28), β-Sitosterol palmitate (29), stigmast-4-en-3-one (30), betulin (31), betulinic acid (32), lupeol (33), 4-hydroxybenzaldehyde (34), 4-hydroxybenzoic acid (35), methyl 4-hydroxybenzoate (36), vanillin (37), vanillic acid (38), 3,4,5-trimethoxybenzoic acid (39), stearic acid (40), methyl stearate (41), monopalmitolein (42), uracil (43), niacinamide (44), (-)-2-(2-hydroxy propanamido) benzamide (45), dibutyl terephthalate (46), abscisic acid (47). In the anti-inflammatory activity evaluation assay, compounds 6, 7, 9, 14, 21, 24, 25, 46 showed inhibitory effects on NO production. Conclusion Compounds 1, 4, 5, 8—12, 15, 17—22, 24—27, 29—31, 34—37, 39, 44—47, totaling 31 compounds, were isolated from Hedysari Radix for the first time. Among them, compound 17was isolated from nature for the first time and its NMR data were supplemented. In addition, compounds 7, 24, and 25 showed significant inhibition of NO and better anti-inflammatory activity compared to the positive control quercetin (20 µg/mL) at the same concentration.
[中图分类号]
R284.1
[基金项目]
甘肃省科技计划项目(22CX8NA003);甘肃省药品监督管理局科研项目(2020GSMPA-KL11,2024GSMPA-KL08)