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[摘要]
目的 对簕欓花椒Zanthoxylum avicennae进行化学成分和生物活性研究.方法 采用 Diaion HP-20、MCI-Gel CHP-20、Sephadex LH-20、Toyopearl HW-40、RP18及硅胶等柱色谱法对簕欓花椒中的化学成分进行分离纯化,根据理化性质和波谱技术(1H-NMR、13C-NMR、HR-ESI-MS)鉴定化合物的结构,采用斜面试管法和海虾致死生物活性法测定部分化合物的抑菌活性和细胞毒活性.结果 从簕欓花椒醋酸乙酯部位和正丁醇部位共分离鉴定了9个化合物,分别为二氢山柰素(1)、滨蒿内酯(2)、3-吲哚甲酸(3)、6-oxo-2(4-hydroxy-3,5-dimethoxyphenyl)-3,7-dioxabicyclo-[3.3.0]-octane(4)、辛二酸(5)、4,4-二甲基-1,7-庚二酸(6)、丁香酸甲酯(7)、β-谷甾醇(8)、前茵芋碱(9).其中化合物2对玉米大斑病菌和大麦赤霉病菌具有较强的抗真菌活性,最低抑制浓度(MIC)值均为15.63 μg/mL;化合物1~3具有一定的细胞毒活性,对海虾致死的LC50值分别为9.8、2.6、4.9 μg/mL.结论 除化合物9外,其他化合物均为首次从该植物中分离得到,其中化合物2具有较强的抗真菌活性,化合物1~3具有一定的细胞毒活性.
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[Abstract]
Objective To study the chemical constituents of the ethyl acetate (EtOAc) extract from Zanthoxylum avicennae and their bioactivities. Methods The compounds were isolated by Diaion HP-20, Toyopearl HW-40, MCI-Gel CHP-20, Sephadex LH-20, RP18, and silica gel column chromatographic methods. Their structures were identified on the basis of physicochemical and spectroscopic analyses; The antibacterial activity and toxicity of compounds 1-3 were investigated by the lethal-to-prawn larva bioactivity experiment and the slanting test-tube experiment. Results Nine constituents were isolated from the EtOAc and n-BuOH fractions of Z. avicennae. Their structures were identified as dihydrokaempferide (1), scoparone (2), 1H-indole-3-carboxylic acid (3), 6-oxo-2(4-hydroxy-3,5-dimethoxyphenyl)-3,7-dioxabicyclo-[3.3.0]-octane (4), suberic acid (5), 4,4-dinethyl-1,7-heptanedioic acid (6), methyl syringate (7), β-sitosterol (8), and preskimmianine (9). Compound 2 displayed more stronger antifungal activity against Exserohilum turcicum Pass and Fusarium graminearum Schwabe, with the MIC value of 15.63 μg/mL. Compounds 1-3 had shown more stronger toxicity towards brine shrimp, with LC50 values of 9.8, 2.6, and 4.9 μg/mL, respectively. Conclusion All the compounds are isolated from Z. avicennae for the first time except preskimmianine. Compound 2 displays more stronger antifungal activity, while compounds 1-3 have shown more stronger cytotoxicity towards brine shrimp.
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[基金项目]
浙江省自然科学基金资助项目(LY13H280011)