Ito Masae, Murakami Keiko, Yoshino Masataka
Department of Biochemistry, Aichi Medical University School of Medicine, Nagakute, Aichi 480-1195, Japan.
Food Chem Toxicol. 2005 Mar;43(3):461-6. doi: 10.1016/j.fct.2004.11.019.
Antioxidant action of eugenol compounds was analyzed in relation to the role of transition metal. Iron-mediated lipid peroxidation and autooxidation of Fe2+ ion were inhibited markedly by isoeugenol, and less effectively by eugenol. Copper-dependent oxidation of low density lipoprotein (LDL) was potently inhibited by eugenol and isoeugenol to the same extent: eugenol compounds showed protective effects by prolonging lag phase and by suppressing propagation rate in the absence and presence of alpha-tocopherol. Inhibition of LDL oxidation by eugenol compounds was closely related to activities reducing copper and scavenging a stable radical, 1,1'-diphenyl-2-picrylhydrazyl (DPPH). Antioxidant properties of eugenol compounds can be explained by forming complexes with reduced metals. Potent inhibitory effect of isoeugenol on lipid peroxidation may be related to the decreased formation of perferryl ion or the iron-oxygen chelate complex as the initiating factor of lipid peroxidation by keeping iron at a reduced state. Inhibition of LDL oxidation by eugenol compounds is due to the suppression of free radical cascade of lipid peroxidation in LDL by reducing copper ion.
研究了丁香酚类化合物的抗氧化作用与过渡金属作用的关系。异丁香酚能显著抑制铁介导的脂质过氧化和Fe2+离子的自氧化，丁香酚的抑制效果稍弱。丁香酚和异丁香酚对铜依赖性低密度脂蛋白（LDL）氧化的抑制作用程度相同：在有无α-生育酚的情况下，丁香酚类化合物通过延长滞后期和抑制传播速率表现出保护作用。丁香酚类化合物对LDL氧化的抑制作用与还原铜和清除稳定自由基1,1'-二苯基-2-苦基肼（DPPH）的活性密切相关。丁香酚类化合物的抗氧化特性可以通过与还原态金属形成络合物来解释。异丁香酚对脂质过氧化的强效抑制作用可能与过氧亚铁离子或铁-氧螯合物的形成减少有关，后者是脂质过氧化的起始因子，而异丁香酚能使铁保持还原状态。丁香酚类化合物对LDL氧化的抑制作用是由于通过还原铜离子抑制了LDL脂质过氧化的自由基级联反应。
