Tang You-Zhi, Liu Zai-Qun
Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
Cell Biochem Funct. 2007 Mar-Apr;25(2):149-58. doi: 10.1002/cbf.1287.
The major objectives of the present work were focused on assessing the antioxidant capacities of two hydroxyl-substituent Schiff bases, 2-((o-hydroxylphenylimino)methyl)phenol (OSAP) and 2-((p-hydroxylphenylimino)methyl)phenol (PSAP) either used alone or in combination with some familiar water-soluble antioxidants i.e. 6-hydroxyl-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox) and L-ascorbic acid (VC), and lipophilic ones i.e. alpha-tocopherol (TOH) and L-ascorbyl-6-laurate (VC-12). 2,2'-Azobis(2-amidinopropane hydrochloride) (AAPH). Induced hemolysis of human erythrocytes functioned as the evaluation experimental system in this research. The present findings showed that either OSAP or PSAP not only was an antioxidant with high activity in protecting erythrocytes against AAPH-induced hemolysis concentration-dependently, but can also protect erythrocytes by acting with Trolox, TOH, VC and VC-12 synergistically. Based on chemical kinetic deduction, the number of trapping peroxyl radicals, n, of the above-mentioned antioxidants can be calculated in relation to Trolox that traps two peroxyl radicals; thus, TOH can trap 3.83 peroxyl radicals, VC-12 traps 2.87 and VC can only trap 1.08. As for OSAP and PSAP, 8.71 and 13.7 peroxyl radicals can be trapped, respectively, indicating that they were the most efficient inhibitors against AAPH-induced hemolysis. Moreover, the total number of peroxyl radicals trapped by OSAP+Trolox, OSAP+TOH, OSAP+VC and PSAP+VC were higher than the sum of the above individual antioxidant used alone, demonstrating that a mutual promotive effect existed in the above mixed antioxidants. In contrast, owing to the fact that the total number of peroxyl radicals trapped by OSAP+VC-12, PSAP+Trolox, PSAP+TOH and PSAP+VC-12 were less than the sum of the above individual antioxidant used alone, a mutual antagonistic effect was suggested in these combinative usages. This information may be helpful in the pharmaceutical application of two Schiff bases.
本研究的主要目标聚焦于评估两种含羟基取代基的席夫碱,即2-((邻羟基苯基亚氨基)甲基)苯酚(OSAP)和2-((对羟基苯基亚氨基)甲基)苯酚(PSAP)单独使用或与一些常见的水溶性抗氧化剂(即6-羟基-2,5,7,8-四甲基苯并二氢吡喃-2-羧酸(Trolox)和L-抗坏血酸(VC))以及亲脂性抗氧化剂(即α-生育酚(TOH)和L-抗坏血酸-6-月桂酸酯(VC-12))联合使用时的抗氧化能力。2,2'-偶氮二(2-脒基丙烷盐酸盐)(AAPH)诱导的人红细胞溶血用作本研究中的评价实验体系。本研究结果表明,OSAP或PSAP不仅是一种具有高活性的抗氧化剂,能浓度依赖性地保护红细胞免受AAPH诱导的溶血,而且还能与Trolox、TOH、VC和VC-12协同作用来保护红细胞。基于化学动力学推导,相对于捕获两个过氧自由基的Trolox,可以计算出上述抗氧化剂捕获过氧自由基的数量n;因此,TOH可以捕获3.83个过氧自由基,VC-12捕获2.87个,而VC只能捕获1.08个。至于OSAP和PSAP,分别可以捕获8.71个和13.7个过氧自由基,这表明它们是对抗AAPH诱导溶血的最有效抑制剂。此外,OSAP+Trolox、OSAP+TOH、OSAP+VC和PSAP+VC捕获的过氧自由基总数高于上述单独使用的单一抗氧化剂的总和,这表明上述混合抗氧化剂之间存在相互促进作用。相反,由于OSAP+VC-12、PSAP+Trolox、PSAP+TOH和PSAP+VC-12捕获的过氧自由基总数低于上述单独使用的单一抗氧化剂的总和,因此表明这些组合使用中存在相互拮抗作用。这些信息可能有助于这两种席夫碱在药物应用方面的研究。