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毛姜花中的细胞毒活性二萜成分
Cytotoxic Labdane-type Diterpenes and Diterpene Derivative from Hedychium villosum
【摘要】 从毛姜花(Hedychium villosum Wall.)中分离得到1个新二萜(1)和1个已知二萜(3).新二萜命名为Villosumcoronarin,该化合物在氯仿或甲醇溶液中发生异构化,部分转化为其差向异构体1’;其平面结构经质谱、红外光谱、氢谱、碳谱及无畸变极化转移增强技术(DEPT)、氢氢相关谱(1H-1H COSY)和异核多键相关谱(HMBC)等方法确证;其相对构型由氢谱、ROESY及量化计算确证.化合物3用琼斯试剂氧化后得到化合物4.生物活性筛选结果表明,化合物1对人白血病细胞株(HL-60)和肝癌细胞株(SMMC-7721)具有强的细胞毒活性,其活性超过阳性对照顺铂(DDP).化合物4对HL-60和SMMC-7721细胞具有显著的细胞毒活性.
【Abstract】 Research on active components from rhizomes of Hedychium genus has led to isolation of some diterpenes with significant cytotoxic activities against Chinese hamster V-79 cells,KB cells,K562 cells,A549 cells,etc..Hedychium villosum Wall.is a perennial rhizomatous herb distributed in China and partially in Southeast Asia,which is used in the treatment of pain and inflammation.A new labdane-type diterpene(1),together with a known one(3),were isolated from Hedychium villosum.The new diterpene was named as villosumcoronarin,which partially isomerized to its epimer 1′ in solution,e.g.,chloroform or methanol.The gross structures of compounds 1 and 1′ were elucidated on the basis of MS,IR,1H NMR,13C-DEPT NMR,1H-1H COSY and HMBC.The relative configuration was determined by 1H NMR,ROESY and computational methods.Compound 1 was identified as(11S,15R)-11-hydroxy-8(17),12(E)-labdadien-15,16-dial 11,15-hemiacetal.The known compound 3 was oxidized by Jones reagent to get diterpene derivative 4.Bioassays revealed that compound 1 had strong cytotoxic activity against HL-60 and SMMC-7721 cells with IC50values of 0.74 and 4.48 μmol/L,respectively,the activities were stronger than the positive control,cis-diaminedichloroplatinum(DDP).Compound 4 also showed significant activities against HL-60 and SMMC-7721 cells with IC50values of 3.15 and 9.57 mmol/L,respectively.
- 【文献出处】 高等学校化学学报 ,Chemical Journal of Chinese Universities , 编辑部邮箱 ,2012年06期
- 【分类号】R284
- 【被引频次】10
- 【下载频次】276