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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

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【作者】 赵庆邹澄余琴赵声定何红平郝小江

【Author】 ZHAO Qing1,ZOU Cheng2,YU Qin2,ZHAO Sheng-Ding1,HE Hong-Ping3,HAO Xiao-Jiang3 (1.School of Chinese Materia Medica,Yunnan University of Traditional Chinese Medicine,Kunming 650500,China; 2.College of Pharmaceutical Sciences,Kunming Medical University,Kunming 650500,China; 3.State Key Laboratory of Phytochemistry and Plant Resources in West China,Kunming Institute of Botany, Chinese Academy of Sciences,Kunming 650204,China)

【机构】 云南中医学院中药学院昆明医学院药学院中国科学院昆明植物研究所植物化学西部国家重点实验室

【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.

【关键词】 毛姜花二萜细胞毒活性
【Key words】 Hedychium villosumDiterpeneCytotoxic activity
【基金】 国家自然科学基金(批准号:81060262)资助
  • 【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
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