Ubeda A, Montesinos C, Payá M, Terencio C, Alcaraz M J
Free Radic Res Commun. 1993;18(3):167-75. doi: 10.3109/10715769309147490.
The antioxidant action of a series of benzylisoquinoline alkaloids has been investigated. Laudanosoline, protopapaverine, anonaine, apomorphine, glaucine, boldine, bulbocapnine, tetrahydroberberine and stepholidine produced a dose-dependent inhibition of microsomal lipid peroxidation induced by Fe2+/ascorbate, CCl4/NADPH or by Fe3+ ADP/NADPH. Apomorphine exerted the highest inhibitory effects in the three systems of induction used, with a potency higher than propyl gallate. Laudanosoline was particularly effective in the first system, while bulbocapnine and anonaine were more potent when CCl4/NADPH or Fe3(+)-ADP/NADPH were used as inducers. Laudanosoline, protopapaverine, apomorphine, tetrahydroberberine and stepholidine were also potent inhibitors of nitroblue tetrazolium (NBT) reduction. The presence of a free hydroxyl group or preferably of a catechol group is a feature relevant for inhibition of lipid peroxidation and NBT reduction, nevertheless the antioxidant activity of benzylisoquinoline alkaloids cannot be only ascribed to the formation of phenoxy radicals and other free radical species may be formed during aporphine and tetrahydroprotoberberine oxidation. The influence of this series of compounds on the time course of lipid peroxidation suggests that some of them, like apomorphine and boldine act as chain-breaking antioxidants.
对一系列苄基异喹啉生物碱的抗氧化作用进行了研究。劳丹索林、原阿片碱、去甲乌药碱、阿扑吗啡、青藤碱、波尔定碱、白屈菜碱、四氢小檗碱和千金藤啶碱对由Fe2+/抗坏血酸、CCl4/NADPH或Fe3+ ADP/NADPH诱导的微粒体脂质过氧化产生剂量依赖性抑制作用。在所用的三种诱导体系中，阿扑吗啡的抑制作用最强，其效力高于没食子酸丙酯。劳丹索林在第一个体系中特别有效，而当使用CCl4/NADPH或Fe3(+)-ADP/NADPH作为诱导剂时，白屈菜碱和去甲乌药碱的效力更强。劳丹索林、原阿片碱、阿扑吗啡、四氢小檗碱和千金藤啶碱也是硝基蓝四唑（NBT）还原的有效抑制剂。存在游离羟基或更优选儿茶酚基团是抑制脂质过氧化和NBT还原的相关特征，然而苄基异喹啉生物碱的抗氧化活性不能仅归因于苯氧基自由基的形成，在阿朴啡和四氢原小檗碱氧化过程中可能形成其他自由基物种。这一系列化合物对脂质过氧化时间进程的影响表明，其中一些化合物，如阿扑吗啡和波尔定碱，起到链断裂抗氧化剂的作用。
