莱菔子中2个新的含硫衍生物  

Two new sulfur-containing derivatives from Raphani Semen

作　　者：杨佩雯 张培良 韩竹箴[1] 杨颖博[1,3] 吴弢 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,Shanghai 201203,China;College of Pharmacy,Anhui University of Chinese Medicine,Hefei 230012,China;Shanghai Tufeng Pharmaceutical Technology Co.,Ltd.,Shanghai 201203,China)

机构地区：[1]上海中医药大学中药研究所,上海201203 [2]安徽中医药大学药学院,安徽合肥230012 [3]上海图锋医药科技有限公司,上海201203

出　　处：《中草药》2023年第11期3408-3416,共9页Chinese Traditional and Herbal Drugs

基　　金：国家重点研发计划项目(2019YFC1711006)。

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。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)andβ-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.

关 键 词：莱菔子 含硫衍生物 生物碱 调脂活性 降莱菔硫代酸乙酯 莱菔酸甲酯 3 4-二羟基苯甲酸 

分 类 号：R284.1[医药卫生—中药学]