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来自大戟属植物欧氏大戟的具有对人乳腺癌细胞系细胞毒活性的新型大环二萜类化合物。

New macrocyclic diterpenes from Euphorbia connata Boiss. with cytotoxic activities on human breast cancer cell lines.

作者信息

Shadi Somayeh, Saeidi Hojjatollah, Ghanadian Mustafa, Rahimnejad Mohammad Reza, Aghaei Mahmoud, Ayatollahi Syed Majid, Choudhary M Iqbal

机构信息

a Department of Biology, Faculty of Science , University of Isfahan , Isfahan , Islamic Republic of Iran.

出版信息

Nat Prod Res. 2015;29(7):607-14. doi: 10.1080/14786419.2014.979418. Epub 2014 Nov 26.

DOI:10.1080/14786419.2014.979418
PMID:25426544
Abstract

Acetone:chloroform (1:2) extract of the aerial parts of Euphorbia connata Boiss. (Euphorbiaceae) was investigated for its diterpenoids. This led to the isolation of one known and two new diterpenes, belonging to the pentahydroxy-13(17)-epoxy-8,10(18)-myrsinadiene and tetrahydroxy-5,6-epoxy-14-oxo-jatropha-11(E)-ene classes. The structures were elucidated based on (13)C and (1)H NMR as well as 2D NMR, IR and MS spectra and the cytotoxicity for compounds 1-3 were evaluated by using MTT assay against two human breast cancer cell lines. Myrsinane-type compounds - 3,7,14,15-tetraacetyl-5-propanoyl-13(17)-epoxy-8,10(18)-myrsinadiene (1) and 3,7,10,14,15-pentaacetyl-5-butanoyl-13,17-epoxy-8-myrsinene (2) - exhibited moderate inhibitory effects, with IC50 values of 24.53 ± 3.39 and 26.67 ± 1.41 μM against the MDA-MB cell line, and 37.73 ± 3.41 and 34.57 ± 2.12 μM against the MCF-7 cell line, respectively. Jatrophane-type diterpene - 5,6-epoxy-8,9,15-triacetyl-3-benzoyl-14-oxo-jatropha-11(E)-ene (3) - showed weak cytotoxicity, with IC50 values of 55.67 ± 7.09 μM against MDA-MB, and moderate cytotoxicity with IC50 values of 24.33 ± 3.21 μM against MCF-7 cell line.

摘要

对大戟科大戟(Euphorbia connata Boiss.)地上部分的丙酮:氯仿(1:2)提取物中的二萜类化合物进行了研究。从中分离出一种已知的二萜和两种新的二萜,它们分别属于五羟基-13(17)-环氧-8,10(18)-肉豆蔻二烯类和四羟基-5,6-环氧-14-氧代麻风树-11(E)-烯类。基于(13)C和(1)H NMR以及二维NMR、IR和MS光谱对其结构进行了阐明,并使用MTT法对化合物1-3针对两种人乳腺癌细胞系的细胞毒性进行了评估。肉豆蔻烷型化合物——3,7,14,15-四乙酰基-5-丙酰基-13(17)-环氧-8,10(18)-肉豆蔻二烯(1)和3,7,10,14,15-五乙酰基-5-丁酰基-13,17-环氧-8-肉豆蔻烯(2)——表现出中等抑制作用,对MDA-MB细胞系的IC50值分别为24.53±3.39和26.67±1.41μM,对MCF-7细胞系的IC50值分别为37.73±3.41和34.57±2.12μM。麻风树烷型二萜——5,6-环氧-8,9,15-三乙酰基-3-苯甲酰基-14-氧代麻风树-11(E)-烯(3)——显示出较弱的细胞毒性,对MDA-MB的IC50值为55.67±7.09μM,对MCF-7细胞系具有中等细胞毒性,IC50值为24.33±3.21μM。

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