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以天然得到的买麻藤醇为原料,以FeCl3 6H2O为氧化剂进行氧化偶联反应和酸催化二聚反应,获得了2个新的买麻藤醇二聚体及一个新的苯基萘衍生物:4-[1-(2,6-二羟基苯基)-2-(3,5-二羟基苯基)乙基]-2-[(1E)-2-(3,5-二羟基苯基)乙烯基]-1,3-苯二醇(1),2-[1-(2,6-二羟基苯基)-2-(3,5-二羟基苯基)乙基]-5-[(1E)-2-(2,6-二羟基苯基)乙烯基]-1,3-苯二醇(2)和4-(6,8-二甲氧基-2-萘基)-1,3-苯二醇(3).应用波谱分析的方法确定了它们的结构,并分别讨论了它们可能的形成机理.其中,化合物1和2首次为人工合成的二苯乙烯链状二聚体.活性测试结果表明,化合物1,2和3显示有较强的抗氧化活性,其IC50值分别为6.29×10-9,4.19×10-6和2.96×10-5mol L-1;化合物2还显示有较强的抗炎活性.
In this paper, two new melatonin dimer and one new phenylnaphthalene derivative were obtained by the oxidative coupling reaction and acid-catalyzed dimerization reaction of naturally-derived melatonol with FeCl3 6H2O as oxidant : 4- [1- (2,6-dihydroxyphenyl) -2- (3,5-dihydroxyphenyl) ethyl] -2 - [(1E) -2- (3,5-dihydroxybenzene (1), 2- [1- (2,6-dihydroxyphenyl) -2- (3,5-dihydroxyphenyl) ethyl] -5 - (1E) -2- (2,6-dihydroxyphenyl) ethenyl] -1,3-benzenediol (2) and 4- (6,8-dimethoxy-2- naphthyl) -1,3-benzenediol (3). Their structures were confirmed by spectral analysis, and their possible formation mechanisms were discussed respectively. Among them, compounds 1 and 2 were the first synthetic stilbene bis The results of the activity test showed that compounds 1, 2 and 3 showed strong antioxidant activity with IC50 values of 6.29 × 10 -9, 4.19 × 10 -6 and 2.96 × 10 -5 mol L -1 respectively. Compound 2 also showed strong anti-inflammatory activity.