骆驼蓬子生物碱化学成分研究

Alkaloidal chemical compositions from seeds of Peganum harmala

目的研究骆驼蓬Peganum harmala子醇提液酸溶碱沉后总生物碱的化学成分。方法采用多种色谱技术进行分离纯化,通过MS、NMR及合成等方法对化合物结构进行鉴定,并以CCK-8法测定部分化合物对人结肠癌HCT116细胞的体外抗肿瘤活性。结果从骆驼蓬子总生物碱中分离得到了12个化合物,分别为1-甲基-2-甲氧甲基-7-甲氧基-9H-吡啶并[3,4-b]吲哚-2-盐酸盐(1)、对苯二甲酸二(2-乙基)己酯(2)、鸭嘴花酮碱(3)、鸭嘴花碱(4)、harmalanine(5)、去氢骆驼蓬碱(6)、哈尔满(7)、哈尔酚(8)、norharmane(9)、骆驼蓬碱(10)、四氢骆驼蓬碱(11)、骆驼蓬酚(12)。体外抗肿瘤实验表明,化合物5的24 h半数抑制浓度(median inhibition concentration,IC50)为(36.41±1.91)μmol/L。结论化合物1为新化合物,命名为氮杂缩醛去氢骆驼蓬碱A,化合物2为骆驼蓬植物中首次分离得到,而较强共轭系统的化合物5具有潜在的抗癌活性。

Objective To investigate the chemical compositions of total alkaloids from the alcoholic extract of Peganum harmala L.seeds after acid solubilization and alkaline precipitation.Methods The compounds were isolated and purified by various chromatographic techniques,and their structures were characterized by MS,NMR and synthesis,and the in vitro anticancer activities of some compounds against human colon cancer cell HCT116 were determined by CCK-8 method.Results A total of 12 compounds were isolated from the total alkaloids,namely 7-methoxy-2-(methoxymethyl)-1-methyl-9H-pyrido[3,4-b]indol-2-ium chloride(1),bis(2-ethylhexyl)terephthalate(2),vasicione(3),vasicine(4),harmalanine(5),harmine(6),harmane(7),harmol(8),norharmane(9),harmaline(10),tetrahydroharmine(11),and harmalol(12).The in vitro anticancer cell assay showed that the 24 h median inhibition concentration(IC50)of compound 5 was(36.41±1.91)μmol/L.Conclusion Compound 1 is a new compound named azaacetal harmine A,and compound 2 was isolated for the first time from P.harmala L.Compound 5 with the strong conjugation system has potential anticancer activity.