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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

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【作者】 杨佩雯张培良韩竹箴杨颖博吴弢

【Author】 YANG Pei-wen;ZHANG Pei-liang;HAN Zhu-zhen;YANG Ying-bo;WU Tao;Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine;College of Pharmacy, Anhui University of Chinese Medicine;Shanghai Tufeng Pharmaceutical Technology Co., Ltd.;

【通讯作者】 吴弢;

【机构】 上海中医药大学中药研究所安徽中医药大学药学院上海图锋医药科技有限公司

【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.

【基金】 国家重点研发计划项目(2019YFC1711006)
  • 【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
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