Cassels B K, Asencio M, Conget P, Speisky H, Videla L A, Lissi E A
Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago.
Pharmacol Res. 1995 Feb;31(2):103-7. doi: 10.1016/1043-6618(95)80054-9.
The antioxidative properties of the aporphines boldine, glaucine and apomorphine, and of the benzyltetrahydroisoquinolines (+/-)-coclaurine and (+/-)-norarmepavine were compared in the brain homogenate autoxidation model. The IC50 values found lay in the 16-20 microM range for the aporphines and were 131.7 microM, and 79.3 microM for coclaurine and norarmepavine, respectively. These results indicate that the antioxidative capacity (AC) of these compounds is related to the presence of the biphenyl system rather than phenol groups. The non-phenolic glaucine inhibited the 2,2'-azobis-(2-amidinopropane)(AAP)-induced inactivation of lysozyme with an IC50 value of 12 microM, while the corresponding values for the phenolic coclaurine and norarmepavine were 10 and 20 microM, respectively. N-Methylation of glaucine to its quaternary ammonium reduced its protective effect by two-thirds. This result suggests that a benzylic hydrogen neighbouring a nitrogen lone electron pair may be the key to the protective effect of non-phenolic aporphines.
在脑匀浆自氧化模型中比较了阿朴啡碱（去甲乌药碱）、青藤碱和阿扑吗啡以及苄基四氢异喹啉（±）-荷包牡丹碱和（±）-去甲臂形草碱的抗氧化特性。发现阿朴啡碱的半数抑制浓度（IC50）值在16 - 20微摩尔范围内，而荷包牡丹碱和去甲臂形草碱的IC50值分别为131.7微摩尔和79.3微摩尔。这些结果表明，这些化合物的抗氧化能力（AC）与联苯系统的存在有关，而非酚羟基。非酚性的青藤碱抑制2,2'-偶氮二（2-脒基丙烷）（AAP）诱导的溶菌酶失活，IC50值为12微摩尔，而酚性的荷包牡丹碱和去甲臂形草碱的相应值分别为10微摩尔和20微摩尔。青藤碱甲基化形成季铵盐后，其保护作用降低了三分之二。这一结果表明，与氮孤电子对相邻的苄基氢可能是非酚性阿朴啡碱发挥保护作用的关键。
