目的 设计合成两种烯丙基槲皮素类化合物,并考察其抗氧化及抗肿瘤活性。方法 以槲皮素为起始物,通过羟基保护,烯丙基化,Claisen重排,脱保护基等反应合成目标化合物1(8-烯丙基槲皮素)和2(6-烯丙基槲皮素)。分别采用DPPH法和MTT法测定目标化合物及中间产物的抗氧化活性及对肺癌细胞A549和肝癌细胞HepG2增殖的影响。结果 合成了8个以槲皮素为母核的中间产物及终产物,其中4个(1,6,8,9)为新化合物,其结构经1H-NMR、13C-NMR、LC-MS表征。活性测试结果 显示,化合物1、2、5、6、8和9具有抗氧化活性;化合物9具有显著的抑制肺癌细胞A549及肝癌细胞HepG2增殖的作用,化合物5具有抑制肺癌A549细胞增殖的作用。结论 化合物因存在给电子基团而抗氧化活性明显;以乙酰基和甲醚基为保护基时,烯丙基的引入位置对其抗肿瘤活性影响明显。
Abstract
OBJECTIVE To design and synthesize two kinds of allyl-substituted quercetin and investigate their anti-oxidation and anti-tumor activities in vitro. METHODS The target compounds 1 and 2 were first synthesized from quercetin by hydroxyl protection,allylation,Claisen rearrangement and deprotection. The anti-oxidation and anti-tumor activities of the target compounds and intermediate products were evaluated by DPPH and MTT assay. RESULTS Eight compounds were synthesized,including six intermediates and two target compounds,in which four were new compounds. All of them were confirmed by 1H-NMR,13C-NMR and LC-MS spectra. The anti-oxidation and anti-tumor tests showed that compounds 1,2,5,6,8 and 9 had anti-oxidation activities and compound 5 inhibited A549 lung cancer cell proliferation. Compound 9 could inhibit the proliferation of lung cancer A549 cells and HepG2 cells. CONCLUSION The compounds with electron-donating groups have significant anti-oxidant activity. When acetyl and methyl ether groups are used as the protecting groups,the position of introducing allyl group to quercetin has obvious impact on the anti-tumor activity.
关键词
烯丙基槲皮素 /
Claisen重排 /
抗氧化 /
肺癌细胞A549 /
肝癌细胞HepG2
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Key words
allyl-substituted quercetin /
Claisen rearrangement /
anti-oxidation /
lung cancer cells A549 /
liver cancer cells HepG2
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中图分类号：
R284
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参考文献
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