目的 研究狼毒大戟(Euphorbia fischeriana Steud)根部的抗肿瘤化学成分。方法 运用硅胶柱、ODS、Sephadex LH-20柱色谱以及制备HPLC等多种方法对狼毒大戟根部的体积分数95%乙醇提取物进行分离纯化,并利用HR-ESI-MS、NMR等波谱技术对分离得到的化合物进行结构鉴定。运用CCK-8检测法测定分离得到的化合物对人肝癌细胞Hep-G2、人乳腺癌细胞MCF-7和人肺癌细胞A549的细胞毒活性。结果 从狼毒大戟中共分离得到12个化合物,分别鉴定为7-oxocallitrisic acid(1)、ent-12-hydroxy-12[R]-abieta-8(14),13(15)-dien-16,12-olide(2)、13β-hydroxy-7-oxoabiet-8(14)-en-19,6β-olide(3)、decandrol A(4)、daphneaine B(5)、二氢红花菜豆酸(6)、phenethyl-6-O-α-L-arabinofuranosyl-β-D-glucoside(7)、2-(4-hydroxyphenyl)ethyl-O-α-L-arabinofuranosyl-(1→6)-O-β-D-glucopyranoside(8)、γ-pyrone-2-O-β-D-(6-galloyl)-glucopyranoside(9)、6-hydroxy-2-methoxy-4-O-α-L-arabinofurano-syl(1→6)-β-D-glucopyranoside(10)、(2,3-trans,4E)-2,3-methano-4-decen-1-ol)(11)和3, 4′-O-dimethylellagic acid(12)。结论 化合物1,4,5,7～9和11为首次从大戟属植物中分离得到,化合物1,2,4～9,11和12为首次从狼毒大戟中分离得到。化合物2对人肝癌细胞Hep-G2表现出较好的细胞毒活性,其半数抑制浓度(half maximal inhibitory concentration,IC50)值为32.81 μmol·L-1,提示该类二萜化合物可能与狼毒大戟的抗肿瘤活性相关。
Abstract
OBJECTIVE To investigate antitumor chemical constituents from the roots of Euphorbia fischeriana Steud.METHODS The roots of Euphorbia fischeriana Steud were refluxed and extracted with 95% ethanol,then separated and purified repeatedly by silica gel column chromatography, ODS column chromatography, Sephadex LH-20 column chromatography and preparative HPLC.The structures of the isolates were mainly elucidated on the basis of spectroscopic data mainly including HR-ESI-MS and NMR. The CCK-8 assay was used to determine the inhibitory effects of the compounds on the proliferation of human liver cancer cells Hep-G2, human breast cancer cells MCF-7 and human lung cancer cells A549.RESULTS Their structures were identified as 7-oxocallitrisic acid(1), ent-12-hydroxy-12[R]-abieta-8(14),13(15)-dien-16,12-olide(2), 13β-hydroxy-7-oxoabiet-8(14)-en-19,6β-olide(3), decandrol A(4), daphneaine B(5), dihydrophaseic acid(6), phenethyl-6-O-α-L-arabinofuranosyl-β-D-glucoside(7), 2-(4-hydroxyphenyl)ethyl-O-α-L-arabinofuranosyl-(1→6)-O-β-D-glucopyranoside(8), γ-pyrone-2-O-β-D-(6-galloyl)-glucopyranoside(9), 6-hydroxy-2-methoxy-4-O-α-L-arabinofuranosyl(1→6)-β-D-glucopyranoside(10),(2,3-trans,4E)-2,3-methano-4-decen-1-ol)(11) and 3, 4′-O-dimethylellagic acid(12).CONCLUSION Compounds 1, 4,5, 7-9 and 11 are isolated from the genus Euphorbia Linn. for the first time. Compounds 1, 2,4-9, 11 and 12 are isolated from Euphorbia fischeriana Steud for the first time. Compound 2 also displays the high cytotoxicity on Hep-G2 cells with IC50 values of 32.81 μmol·L-1, which suggests that the activity of this kind of diterpenoids might be related to the anti-tumor activity of E.fischeriana.
关键词
狼毒大戟 /
7-oxocallitvisic acid /
结构鉴定 /
细胞毒活性
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Key words
Euphorbia fischeriana Steud /
7-oxocallitvisic acid /
structural identification /
cytotoxicities
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脚注
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基金
国家自然科学基金项目资助(81872761);陕西省自然科学基础研究计划重点项目资助(2022JZ-49);天然药物活性物质与功能国家重点实验室开放项目资助(GTZK202001,GTZK202206)
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