ACTION OF PHENOLIC DERIVATIVES (ACETAMINOPHEN, SALICYLATE, AND 5-AMINOSALICYLATE) AS INHIBITORS OF MEMBRANE LIPID-PEROXIDATION AND AS PEROXYL RADICAL SCAVENGERS
ACTION OF PHENOLIC DERIVATIVES (ACETAMINOPHEN, SALICYLATE, AND 5-AMINOSALICYLATE) AS INHIBITORS OF MEMBRANE LIPID-PEROXIDATION AND AS PEROXYL RADICAL SCAVENGERS
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DOI：
10.1006/abbi.1994.1485
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发表时间：
1994-11-15
影响因子：
3.9
通讯作者：
ALMEIDA, LM
中科院分区：
文献类型：
--
作者：
DINIS, TCP;MADEIRA, VMC;ALMEIDA, LM
酚类化合物对乙酰氨基酚，水杨酸盐，和5-氨基水杨酸盐（5-阿萨）作为脂质过氧化抑制剂的作用进行了研究，在适合建立其抗氧化效力的条件下。这些酚类化合物与二苯基苦肼（DPPH）反应不同，并保护不同的肌浆网膜对脂质过氧化诱导的Fe 2 +/抗坏血酸，作为评估的硫代巴比妥酸反应物质（TBARS）的形成和损失的多不饱和脂肪酰基链。5-对氨基水杨酸迅速与DPPH反应，这表明一种有效的自由基清除剂活性，并被认为是最活跃的抑制Fe 2 +/抗坏血酸诱导的脂质过氧化。这些化合物还表现出由过氧自由基的水溶性2，2 ′-偶氮双-（2-脒基丙烷盐酸盐）偶氮引发剂产生的过氧自由基清除活性，如通过抑制顺式-帕里那酸荧光衰减或氧消耗所证明的。5-阿萨能迅速清除水相中的过氧化氢自由基，产生类似于Trolox或半胱氨酸的浓度依赖性抑制期，表明具有断链型抗氧化活性。相比之下，对乙酰氨基酚和水杨酸盐的反应性明显较弱，基本上作为氧化阻滞剂。虽然在结构上密切相关，但这三种酚类化合物的抗氧化效率有显着差异。5-阿萨较高的抗氧化活性与相对于羟基的p-胺有关，潜在地增加了苯氧基自由基的稳定性。这种稳定作用在水杨酸盐中是不可能的，在对乙酰氨基酚中由于对乙酰基的吸电子作用而降低。(C)1994年出版社出版。
The action of the phenolic compounds acetaminophen, salicylate, and 5-aminosalicylate (5-ASA) as inhibitors of lipid peroxidation was studied under conditions suitable for establishing their antioxidant potencies. These phenolic compounds react differently with diphenylpicrylhydrazyl (DPPH) and protect differently sarcoplasmic reticulum membranes against lipid peroxidation induced by Fe2+/ascorbate, as evaluated by the formation of thiobarbituric acid-reactive substances (TBARS) and by the loss of the polyunsaturated fatty acyl chains. 5-Aminosalicylate reacts promptly with DPPH, suggesting a potent radical scavenger activity and was found to be the most active in inhibiting Fe2+/ascorbate-induced lipid peroxidation. These compounds also exhibit peroxyl radical scavenging activity generated by the water-soluble 2,2'-azobis-(2-amidinopropane hydrochloride) azoinitiator of peroxyl radicals, as evidenced by the inhibition of cis-parinaric acid fluorescence decay or oxygen consumption. 5-ASA rapidly scavenges peroxyl radicals in the aqueous phase, producing a concentration-dependent inhibition period similar to Trolox or cysteine, suggesting an antioxidant activity of chain-breaking type. By comparison, the reactivities of acetaminophen and salicylate are significantly weaker, acting essentially as oxidation retardants. Although closely related in structure, the antioxidant efficiencies of the three phenolic compounds are significantly different. The higher antioxidant activity of 5-ASA is putatively related with the p-amine relative to the hydroxyl group, potentially increasing the stability of the phenoxyl radical. Such a stabilization is not possible with salicylate and is decreased in acetaminophen by an electron withdrawing effect of the p-acetyl. (C) 1994 Academic Press, Inc.