臭草二氯甲烷部位化学成分研究

Chemical constituents from the dichloromethane fraction of Ruta graveolens L.

为研究臭草(Ruta graveolens L.)地上部分的化学成分及其抗Epstein-Barr病毒(EBV)活性。本研究采用硅胶等柱色谱和制备液相色谱等手段对臭草地上部分的95%乙醇浸提物二氯甲烷萃取部位进行分离纯化,并根据理化性质和谱学数据对化合物结构进行鉴定,鉴定后化合物进行抗EBV活性测试。从臭草乙醇提取物二氯甲烷萃取部分离得到30个化合物,分别鉴定为山小柑碱(1)、2-羟基-3-异丙氧基-1,4-甲氧基-10-甲基吖啶酮(2)、芸香日酮(3)、1-羟基-3-甲氧基-N-甲基吖啶酮(4)、羟甲基吖啶酮环氧化物(5)、rutalinium(6)、(-)-日把里尼定(7)、ribalinium(8)、(+)-ribaline(9)、γ-fagarine(10)、香草木宁碱(11)、合帕洛平(12)、茵芋碱(13)、(-)-去乙酰基芸香苦素(14)、chalepensin(15)、(+)-芸香瑞亭(16)、花椒毒素(17)、补骨酯素(18)、佛手柑内酯(19)、7-preniloxicumarin(20)、异东莨菪素(21)、6-羟基香豆素(22)、东莨菪苷(23)、芸香灵(24)、芸香宁(25)、3-(3,4,5-三甲氧基苯基)-2-丙烯-1-醇(26)、moskachan D(27)、胡椒基丙酮(28)、芦丁(29)、1,3-disinapoyl-gentiobiose(30),其中化合物2、7、9、12、20、22、23、26、27、28、30为首次从该植物中获得。将30个化合物均测试其体外抗EBV活性,结果显示在30μmol/L浓度下,共有6个化合物抑制EB病毒裂解复制达到50%以上,其中化合物5、24,显示较好的抗EB病毒活性,IC 50分别为2.4μmol/L与4.8μmol/L,高于阳性对照组(右旋芸香苦素,IC 50=7.0μmol/L)。

To investigate chemical constituents from the aerial part of Ruta graveolens L.and their anti-Epstein-Barr virus(EBV)activity.The compounds from the dichloromethane fraction of Ruta graveolens L.were separated by column chromatography such as silica gel,MCI gel CHP-20,ODS,and Sephadex LH-20 and purified by preparative HPLC method,which led to the isolation of 30 compounds,including arborinine(1),2-hydroxy-3-isopropoxy-1,4-dimethoxy-10-methylacridanone(2)rutacridone(3),1-hydroxy-3-methoxy-N-methylacridone(4),20-Hydroxyrutacridon-epoxide(5),rutalinium(6),(-)-ribalinidine(7),ribalinium(8),(+)-ribaline(9),γ-fagarine(10),kokusaginine(11),haplopine(12),skimmianine(13),(-)-chalepin(14),chalepensin(15),(+)-rutaretin(16),xanthotoxin(17),psoralen(18),bergapten(19),7-preniloxicumarin(20),isoscopoletin(21),6-hydroxycoumarin(22),scopolin(23),graveoline(24),graveolinine(25),3,4,5-trimethoxycinnamyl alcohol(26),moskachan D(27),piperonyl acetone(28),rutin(29),1,3-disinapoyl-gentiobiose(30).The structures of all the isolated compounds were elucidated by spectroscopic methods(MS,1H NMR,13 C NMR)and comparison with reported literatures.Compounds 2,7,9,12,20,22,23,26,27,28,30 were obtained from this plant for the first time.The isolated compounds 1-30 were evaluated for their anti-EBV activity.The results showed that six compounds inhibited more than 50%cleavage and replication of EB virus with concentrations of 30μmol/L.Compounds 5 and 24 showed better anti-EBV activity with IC 50 of 2.4μmol/L and 4.8μmol/L,respectively,which was higher than(+)-rutamarin in positive control group(IC 50=7.0μmol/L).