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没药倍半萜成分的分离鉴定及抗肿瘤活性

吉恺1,孔峰1,沈涛2,王小玲1,许爱辉1,苑辉卿1,张秀田2   

  1. 山东大学 1. 医学院生物化学与分子生物学教研室; 2. 药学院天然药物化学教研室, 济南 250012
  • 收稿日期:2007-12-12 修回日期:1900-01-01 出版日期:2008-04-16 发布日期:2008-04-16
  • 通讯作者: 苑辉卿

Separation and identification of myrrh sesquiterpenoids and its anti-proliferation effect on tumor cell

JI Kai1,KONG Feng1,SHEN Tao2,WANG Xiao-ling1,XU Ai-hu1,YUAN Hui-qing1,ZHANG Xiu-tian2   

  1. 1. Institute of Biochemistry and Molecular Biology, School of Medicine, Shandong University;2. Department of Natural Pharmacochemistry, School of Pharmaceutical Science, Shandong University
  • Received:2007-12-12 Revised:1900-01-01 Online:2008-04-16 Published:2008-04-16
  • Contact: YUAN Hui-qing

摘要: 目的从没药提取物中分离纯化倍半萜单体成分,并探讨其抑制肿瘤细胞增殖的生物活性。方法没药石油醚提取部分经硅胶柱层析分离得到二十多个倍半萜类化合物。其中化合物1和2的结晶分别经熔点测定、薄层层析、1H-NMR和13C-NMR数据分析以及与已知化合物比较,确定其化学结构。 利用MTT法检测化合物1和2对大肠癌细胞HT-29和激素非依赖型前列腺癌细胞PC-3、PC-3M、DU-145及正常肝的永生化细胞LO2细胞增殖的影响。结果经理化性质鉴定、波谱分析,确定化合物1的结构为[1(10)E,2R,4R]-2-甲氧基-8,12-环氧吉玛-1(10),7,11-三烯-6-酮;化合物2的结构为2-甲氧基-5-乙酰基-4-呋喃吉玛-1(10)-烯-6-酮,二者同属没药吉玛烷型倍半萜类化合物。MTT结果表明,化合物1和2对大肠癌细胞增殖的抑制作用较弱。而对三种激素非依赖型前列腺癌细胞的增殖有非常显著的抑制作用(P<0.01),且呈剂量依赖性。另外,化合物对正常肝永生化细胞的增殖无明显影响。结论经分离纯化、理化性质鉴定和波谱分析,确定了没药吉玛型倍半萜化合物1和2的结构,该化合物对前列腺癌细胞的增殖有明显的抑制作用。

Abstract: To determine the structures of two sesquiterpene compounds isolated from Commiphora opobalsamum, and to investigate its anti-proliferation effect on tumor cell growth. Methods Two sesquiterpenoids were isolated from the resinous exudates of Commiphora opobalsamum. Their structures were established on the basis of physical and chemical properties, and 1H-NMR and 13 Results Structures of two sesquiterpenoids were determined as (1(10)E,2R,4R)-2-methoxy-8, 12-epoxygermacra-1(10), 7, 11-trien-6-one and 2-methoxy-5-acetoxyfuranogermacr-1(10)-en-6-one, respectively. The results of MTT assay showed that both two compounds had an inhibitory effect on proliferation of the hormone-independent prostate cancer cell lines in a concentration-dependent manner. While no significant anti-proliferation activity was observed in colorectal cells exposed to these chemicals at low concentrations. Furthermore, less cytotoxicity of these compounds was shown by using immortalizied liver normal cell line at concentrations tested. Conclusions Two germacrane sesquiterpenoids were identified the structures, and they can significantly inhibit the proliferation of hormone-independent prostate cancer cell growth.

Key words: Myrrh, Germacrane Sesquiterpenoids, Prostate neplasms, Cell lines

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  • R931.6
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