裸花紫珠化学成分及细胞毒活性研究

Chemical constituents from Callicarpa nudiflora and their cytotoxic activities

综合运用HP-20大孔吸附树脂柱粗分、硅胶柱和Sephadex LH-20凝胶柱等色谱法分离纯化海南道地药材裸花紫珠Callicarpa nudiflora中的化学成分,借助波谱数据解析化合物的结构。采用MTT法测定其粗提物和单体化合物的细胞毒活性。发现裸花紫珠醇提物50%,70%乙醇洗脱物对肿瘤细胞的增殖有较强的抑制作用。从上述活性部位分离和鉴定得到12个化合物,其中6个黄酮：木犀草苷（1）,木犀草素-4’-O-β-D-吡喃葡萄糖苷（2）,6-羟基木犀草素-7-O-β-D-吡喃葡萄糖苷（3）,木犀草素-7-O-新橙皮苷（4）,野漆树苷（5）,木犀草素-7,4’-二-O-葡萄糖苷（6）;3个苯乙醇苷：连翘酯苷（7）,类叶升麻苷（8）,alyssonoside（9）;3个环烯醚萜苷：梓醇（10）,nudifloside（11）,益母草苷（12）。化合物3~6,10和12为首次从该属植物中分离得到,化合物9为首次从该种植物中分离得到。单体化合物的细胞毒活性实验显示,黄酮类化合物1~6整体均显示出对宫颈癌Hela,肺癌A549和乳腺癌MCF-7细胞不同程度的抑制作用,化合物3,5和11的细胞毒活性比较突出。综合分析表明,黄酮类化合物是裸花紫珠活性部位的主要化学成分,有抑制肿瘤细胞增殖的潜在功效;苯乙醇苷类化合物含量较高,但不表现细胞毒活性;环烯醚萜苷类成分少量存在,表现出微弱的细胞毒活性。

The chemical consitituents from cytotoxic fraction of the Callicarpa nudiflora extract were isolated and purified by a combination of HP-20 macroporous resin,silica gel and Sephadex LH-20 column chromatographies. The structures were elucidated on the basis of the spectroscopic data and comparison of their spectroscopic data with reported data. The cytotoxicity was evaluated by the MTT assay. The 50% and 70% EtOH elutions of EtOH-extract showed significant cytotoxic activities,leading to the isolation of twelve compounds,which were identified as luteoloside（ 1）,lutedin-4’-O-β-D-glucoside（ 2）,6-hydroxyluteolin-7-O-β-glucoside（ 3）,lutedin-7-O-neohesperidoside（ 4）,rhoifolin（ 5）,luteolin-7,4’-di-O-glucoside（ 6）,forsythoside B（ 7）,acteoside（ 8）,alyssonoside（ 9）,catalpol（ 10）,nudifloside（ 11）,and leonuride（ 12）. Compounds 3-6,10 and 12 were isolated from this genus for the first time,and compound 9 was isolated from this plant for the first time. The cytotoxicity assay demonstrated that flavonoids 1-6,in various concentrations,showed monolithic proliferation inhibitory activities against Hela,A549 and MCF-7 cell lines. Compounds 3,5 and iridoid glycoside 11 possessed higher cytotoxicacivities. In short,flavonoids are the main components of cytotoxic extract from C. nudiflora,while phenylethanoid glycosides are the predominant ingredient but inactive to cancer cell lines. In addition,the minor iridoid glycoside expressed weak cytotoxic activity.