白花除虫菊化学成分及其生物活性的研究

Chemical constituents and biological activities of Pyrethrum cinerariifolium

该研究应用柱层析法、薄层层析法和波谱法对白花除虫菊(Pyrethrum cinerariifolium)全株甲醇提取物进行分离纯化、结构鉴定,并分别采用MTT法、生物活性测定法和抑菌圈法测定所得化合物抗肿瘤、杀线虫和抑菌活性。结果表明:经波谱法鉴定化合物结构分别为tulirinol(1),sesamin(2),β-cyclopyrethrosin(3)和3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7,8-dimethoxy-4H-1-benzopyran-4-one(4)。抗肿瘤活性显示化合物3对白血病细胞株HL-60、肝癌细胞株SMMC-7721、肺癌细胞株A-549、乳腺癌细胞株MCF-7和结肠癌细胞株SW480均表现出显著的抑制活性,其IC_(50)分别为3.800、2.890、2.930、4.600和5.160μmol·L^(-1);化合物1活性比3稍弱,其IC_(50)分别为5.020、10.760、12.310、12.310和12.250μmol·L^(-1);其中化合物3对各肿瘤细胞株IC_(50)值均小于顺铂。抗菌活性表明化合物3对大肠杆菌、蜡样芽孢杆菌、枯草芽孢杆菌和金黄色葡萄球菌均表现出明显的抑菌活性,且随着浓度增加活性逐渐增强,而化合物1和化合物2仅对部分菌株表现出微弱抑菌活性;杀线虫活性显示化合物3对秀丽隐杆线虫和全齿复活线虫均表现出显著的毒杀活性,且随着时间、浓度增加活性逐渐增强;而在同一时间点对秀丽隐杆线虫的毒杀活性强于全齿复活线虫。从白花除虫菊中分离所得4个化合物均为首次从该植株中发现,且首次报道了化合物3杀线虫和抑菌活性,值得进一步开发应用。

The chemical constituents of Pyrethrum cinerariifolium and the measure of antitumor activity, antibacterial ac-tivity and nematicidal activity of the compounds which were isolated from P. cinerariifolium were investigated. The whole plant organ of P. cinerariifolium was extracted with methanol three times, and the methanol extract of P. cinerariifolium was isolated by column chromatography and thin layer chromatography （TLC）. The compounds structures were identified by spectral method. The methods of MTT, biological activity-determination and inhibition zone were performed for the ac-tivities of antitumor, nematicidal and bacteriostat respectively. Four compounds were obtained from the extract of P. cin-erariifolium, and identified as tulirinol （1）, sesamin （2）, β-cyclopyrethrosin （3） and 3, 5-dihydroxy-2-（4-hydroxy-3-methoxyphenyl）-7, 8-dimethoxy-4H-1-benzopyran-4-one （4） based on spectral data. Compound 3 showed significant ac-tivity against Leukemia cell HL-60, liver cancer cell SMMC-7721, lung cancer cell A-549, breast cancer cell MCF-7 and colon cancer cell SW480 with IC50 values of 3.800, 2.890, 2.930, 4.600 and 5.160 μmol·L-1 respectively. Com-pound 1, which IC50 values were 5.020, 10.760, 12.310, 12.310 and 12.250 μmol·L-1 respectively, showed lower ac-tivity than compound 3 against these cell lines. Compound 3 showed lower values of IC50 than cisplatin against part of the cancer cell lines. The antibacterial bioassay showed Compound 3 had prominent activity against Escherichia coli, Bacillus cereus, B. subtilis and Staphyloccocus aureus with the values of inhibition zone more than 1.1 cm with a dose-dependent manner. Compounds 1 and 2 had weak antibacterial activity. However, Compound 4 did not show any activity against four pathogenic bacteria. Compound 3 revealed nematicidal activity against Panagrellus redivivus and Caenorhabditis elegans with a time/ dose-dependent manner, and the compound had stronger activity against C. elegans than Panagrellus redivi-vus at the same time point. Compounds 1, 2 and 4 did not show any activity against two nematodes. Together, all com-pounds were isolated from the P. cinerariifolium for the first time, and Compound 3 was firstly reported to show nemati-cidal and antibacterial activities, so it deserved to be further developed and applied.