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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Hep G2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Hep G2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。
OBJECTIVE To design and synthesize two allyl quercetin compounds and investigate their antioxidant and antitumor activities. Methods The target compounds 1 (8-allyl quercetin) and 2 (6-allyl quercetin) were synthesized by the reaction of hydroxyl protection, allylation, Claisen rearrangement and deprotection with quercetin as the starting material. Quercetin). The anti-oxidative activity of target compounds and intermediates and the effects on the proliferation of lung cancer cells A549 and Hep G2 were determined by DPPH assay and MTT assay respectively. Results Eight intermediates and final products with quercetin as the core were synthesized. Four of them (1,6,8,9) were new compounds and their structures were characterized by 1H-NMR, 13C-NMR and LC-MS . The results of the activity test showed that compounds 1, 2, 5, 6, 8 and 9 have antioxidant activity. Compound 9 has a significant inhibitory effect on the proliferation of lung cancer cell A549 and Hep G2 cell. Compound 5 has the effect of inhibiting the proliferation of lung cancer A549 cell . Conclusion The compounds have obvious anti-oxidative activity due to the existence of electron-donating groups. When acetyl and methyl ether are used as the protective groups, the introduction position of allyl has obvious effect on the antitumor activity.