[关键词]
[摘要]
目的 研究十字花科芸薹属植物芜菁Brassica rapa块根中的化学成分,并评估其抗炎作用。方法 利用硅胶、薄层色谱、十八烷基键合硅胶、羟丙基葡聚糖凝胶、高效液相等方法系统分离纯化,采用核磁共振、质谱、紫外等光谱、波谱技术鉴定结构,使用CCK-8法评价化合物对小鼠巨噬细胞RAW264.7的细胞毒性,同时采用Griess法测定化合物体外抗炎活性。结果 从芜菁块根70%乙醇提取物中分离到25个化合物,分别鉴定为2-C-β-D-葡萄糖-吲哚-3-乙腈(1)、芥子酸(2)、p-香豆酸(3)、阿魏酸(4)、芥子酸甲酯(5)、4-羟基肉桂酸甲酯(6)、反-4-甲氧基肉桂酸(7)、苹果酸二甲基阿魏酰酯(8)、苹果酸二甲基芥子酰酯(9)、对羟基苯甲醛(10)、苯乙酸(11)、苯基-1,2-乙二醇(12)、3-苯基丙酰胺(13)、苯乙基-β-D-葡萄糖苷(14)、4-(3-hydroxypropyl) phenyl β-D-glucopyranoside(15)、idaeusinol B(16)、丁香树脂酚-4-O-β-D-葡萄糖苷(17)、equiselignan A(18)、红花菜豆酸(19)、脱落酸(20)、玫瑰花苷(21)、佛手柑内酯(22)、methylthioadenosine(23)、5-羟甲基糠醛(24)、rabdosia acids B(25)。CCK-8毒性测试表明,化合物16、22和25有细胞毒性,Griess法体外实验表明,化合物1~25显示出不同程度的抗炎活性,化合物8、9具有明显的抗炎活性。结论 化合物1为吲哚硫代葡萄糖苷类化合物,化合物2~9、16~18为苯丙素类化合物,化合物10~12、14、15为苯环衍生物,化合物13、23为含氮类化合物,其中化合物1、6~9、13、15、16、18、19、23为首次从芜菁中分离得到。体外抗炎活性表明,化合物8、9具有明显的抗炎活性,其半数抑制浓度(median inhibition concentration,IC50)值分别为6.95、6.46 μmol/L。
[Key word]
[Abstract]
Objective To investigate the chemical constituents of the taproots of Brassica rapa (Qiamagu) and evaluate their anti-inflammatory activity. Methods The chemical constituents were systematically isolated and purified using silica gel, ODS, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were elucidated by comprehensive spectroscopic analyses, including NMR, MS, and UV. The cytotoxicity of the isolates against RAW264.7 murine macrophages was assessed using the CCK-8 assay. The in vitro anti-inflammatory activity was evaluated via the Griess method. Results Twenty-five compounds were isolated from the 70% ethanol extract of B. rapa taproots and identified as 2-C-β-D-glucosyl-indole-3-acetonitrile (1), sinapic acid (2), p-coumaric acid (3), ferulic acid (4), methyl sinapate (5), methyl 4-hydroxycinnamate (6), trans-4-methoxycinnamic acid (7), dimethyl feruloyl malate (8), sinapoyl dimethyl malate (9), p-hydroxybenzaldehyde (10), phenylacetic acid (11), phenylethane-1, 2-diol (12), 3-phenylpropanamide (13), phenylethyl-β-D-glucoside (14), 4-(3-hydroxypropyl) phenyl β-D-glucopyranoside (15), idaeusinol B (16), syringaresinol-4-O-β-D-glucoside (17), equiselignan A (18), phaseic acid (19), abscisic acid (20), roseoside (21), bergapten (22), methylthioadenosine (23), 5-hydroxymethylfurfural (24), and rabdosia acid B (25). The CCK-8 assay demonstrated the cytotoxicity of compounds 16, 22, and 25. To evaluate the anti-inflammatory activity in vitro, the Griess method was employed. The results demonstrated that all tested compounds exhibited varying degrees of inhibitory activity. Conclusion Compound 1 is an indole glucosinolate; compounds 2—9 and 16—18 are phenylpropanoids, compounds 10—12, 14 and 15 are benzene ring derivatives, and compounds 13 and 23 are nitrogen-containing compounds. Among them, compounds 1, 6—9, 13, 15, 16, 18, 19, and 23 are isolated from B. rapa for the first time. In the anti-inflammatory assay, with compounds 8 and 9 demonstrating significant effects, yielding IC50 values of 6.95 and 6.46 μmol/L.
[中图分类号]
R284.1
[基金项目]
国家重点研发计划项目(2020YFE0205600);天山人才计划项目(2022TSYCLJ0064);新疆维吾尔族自治区重点研发计划项目(2024B2023);中山市科学技术局科研项目(2020YFE0205600)