2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran: design and evaluation as a novel radical-scavenging antioxidant against lipid peroxidation.
2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran: design and evaluation as a novel radical-scavenging antioxidant against lipid peroxidation.
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2,3-二氢-5-羟基-2,2-二戊基-4,6-二叔丁基苯并呋喃：作为抗脂质过氧化的新型自由基清除抗氧化剂的设计和评估。
DOI：
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发表时间：
1997
影响因子：
3.9
通讯作者：
E. Niki
中科院分区：
文献类型：
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作者：
N. Noguchi;Y. Iwaki;M. Takahashi;E. Komuro;Y. Kato;K. Tamura;O. Cynshi;T. Kodama;E. Niki
为了开发一种新的有效的自由基清除抗氧化剂，酚类化合物的理想结构的设计考虑的因素，决定抗氧化剂的效力。合成了2，3-二氢-5-羟基-2，2-二戊基-4，6-二叔丁基苯并呋喃（BO-653）。电子自旋共振研究表明，BO-653衍生的苯氧基自由基比α-生育酚氧基自由基更稳定。BO-653可迅速还原α-生育酚氧自由基，但α-生育酚不能还原BO-653衍生的苯氧自由基。然而，BO-653对过氧自由基的化学反应性小于α-生育酚。这被解释为体积庞大的叔丁基基团在两个邻位的空间效应，阻碍了过氧自由基的酚氢的访问。然而，叔丁基取代基增加了BO-653自由基的稳定性和亲脂性，并且其对磷脂酰胆碱脂质体膜中脂质过氧化的抗氧化效力上级于α-生育酚。在均相溶液中，抗坏血酸可还原BO-653的苯氧基自由基，使BO-653在脂质氧化过程中不受影响。另一方面，抗坏血酸在脂质体膜的氧化中不放过BO-653。因此，BO-653是一种有效的新型自由基清除抗氧化剂。
To develop a novel potent radical-scavenging antioxidant, the ideal structure of a phenolic compound was designed considering the factors that determine antioxidant potency. 2,3-Dihydro-5-hydroxy-2,2-dipentyl-4, 6-di-tert-butylbenzofuran (BO-653) was thus synthesized and its antioxidant activity was evaluated against lipid peroxidations in vitro. The electron spin resonance study showed that the phenoxyl radical derived from BO-653 was more stable than alpha-tocopheroxyl radical. BO-653 reduced alpha-tocopheroxyl radical rapidly, but alpha-tocopherol did not reduce the phenoxyl radical derived from BO-653. However, the chemical reactivity of BO-653 toward peroxyl radical was smaller than that of alpha-tocopherol. This was interpreted as the steric effect of bulky tert-butyl groups at both ortho positions which hindered the access of peroxyl radical to the phenolic hydrogen. However, the tertbutyl substituents increased the stability of BO-653 radical and also lipophilicity, and its antioxidant potency against lipid peroxidation in phosphatidylcholine liposomal membranes was superior to that of alpha-tocopherol. Ascorbic acid reduced the phenoxyl radical derived from BO-653 and spared BO-653 during the oxidation of lipid in the homogeneous solution. On the other hand, ascorbic acid did not spare BO-653 in the oxidation of liposomal membranes. It was concluded that BO-653 is a potent novel radical-scavenging antioxidant.