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莱菔子中2个新的含硫衍生物
Two new sulfur-containing derivatives from Raphani Semen
【摘要】 目的 研究莱菔子Raphani Semen的化学成分及其调脂活性。方法 采用硅胶、Sephadex LH-20、ODS、半制备液相等色谱方法对莱菔子70%乙醇提取物分离纯化,综合应用波谱数据和理化性质鉴定化合物结构。通过3T3-L1前脂肪细胞的胰岛素抵抗模型评价化合物的体外调脂活性。结果 从莱菔子70%乙醇提取物中分离纯化得到了14个化合物,分别鉴定为降莱菔硫代酸乙酯(1)、莱菔酸甲酯(2)、芥子碱(3)、(E)-2-(4-hydroxy-2-oxoindolin-3-ylidene)acetonitrile(4)、2-(4-hydroxy-2-oxoindolin-3-yl)acetonitrile(5)、6-methoxyindole-3-carboxylic acid O-β-D-glucopyranosyl ester(6)、cappariloside A(7)、3’,6-二芥子酰基蔗糖(8)、吐叶醇(9)、3,4-二羟基苯甲醛(10)、3,4-二羟基苯甲酸(11)、5-羟甲基糠醛(12)、2-羟甲基-5-呋喃丙烯酸乙酯(13)和β-谷甾醇(14)。结论 化合物1和2为新化合物。两者的生源前体均为甲硫氨酸。化合物1为异硫氰酸酯和乙醇的人工产物。化合物4、6、10、11、13为首次从莱菔子中分离得到。体外活性实验结果表明,化合物1和2均具有一定的调脂活性。
【Abstract】 Objective To study the chemical constituents and lipid regulating activity of Laifuzi(Raphani Semen). Methods The 70% ethanol extract of Raphani Semen was separated and purified by various chromatographic techniques such as silica gel,Sephadex LH-20, ODS and semi-preparative liquid chromatographic columns. The structures of these compounds were identified by spectral data and physicochemical properties. Subsequently, lipid-regulating activity of the compounds was evaluated in vitro by the insulin resistance model of 3T3-L1 preadipocytes. Results A total of 14 compounds were separated and purified from the 70% ethanol extract of Raphani Semen, which were identified as: ethyl norsulforaphanate(1), methyl raphanide(2), sinapine(3),(E)-2-(4-hydroxy-2-oxoindolin-3-ylidene) acetonitrile(4), 2-(4-hydroxy-2-oxoindolin-3-yl)acetonitrile(5), 6-methoxyindole-3-carboxylic acid O-β-D-glucopyranosyl ester(6), cappariloside A(7), 3’,6-disinapoyl sucrose(8), vomifoliol(9),3,4-dihydroxy-benzaldehyde(10), 3,4-dihydroxy-benzoic acid(11), 5-hydroxy-methylfurfural(12), 2-hydroxymethyl-5-furanacrylic acid ethyl ester(13) and β-sitosterol(14). Conclusion Compounds 1 and 2 are new compounds, and their biological precursors are both methionine. Furthermore, compound 1 is an artificial product of isothiocyanate reacting with ethanol. Compounds 4, 6, 10, 11 and 13 were isolated from Raphani Semen for the first time. Compounds 1 and 2 had potential anti-adipogenic effect in vitro.
【Key words】 Raphani Semen; sulfur-containing compounds; alkaloid; anti-adipogenic effect; ethyl norsulforaphanate; methyl raphanide; 3,4-dihydroxy-benzaldehyde;
- 【文献出处】 中草药 ,Chinese Traditional and Herbal Drugs , 编辑部邮箱 ,2023年11期
- 【分类号】R284.1
- 【下载频次】55