Okada N, Satoh K, Atsumi T, Tajima M, Ishihara M, Sugita Y, Yokoe I, Sakagami H, Fujisawa S
Department of Oral Diagnosis, Meikai University School of Dentistry, Saitama, Japan.
Anticancer Res. 2000 Sep-Oct;20(5A):2955-60.
The ability of nine synthetic eugenol-related compounds to scavenge O2- (generated by the hypoxanthine-xanthine oxidase reaction) was compared with their radical generation and cytotoxic activity. ESR spectroscopy showed that eugenol (4-allyl-2-methoxyphenol), 2-allyl-4-methoxyphenol, 2-allyl-4-t-butylphenol and 2,4-dimethoxyphenol efficiently scavenged O2- and produced radicals under alkaline conditions. 2-allyl-4-t-butylphenol showed the highest cytotoxic activity and DNA-synthesis inhibitory activity, possibly due to the hydrophobic radical reactivity. 2-allyl-4-methoxyphenol and 2,4-dimethoxyphenol showed higher antioxidant activity than 3-t-butyl-4-hydroxyanisol (BHA), but all these compounds showed comparable cytotoxic activity with each other. These findings suggest a possible link between the cytotoxic activity and radical generation/scavenging activity in eugenol-related compounds.
将9种合成的丁香酚相关化合物清除超氧阴离子（由次黄嘌呤-黄嘌呤氧化酶反应产生）的能力与其自由基生成和细胞毒性活性进行了比较。电子自旋共振光谱表明，丁香酚（4-烯丙基-2-甲氧基苯酚）、2-烯丙基-4-甲氧基苯酚、2-烯丙基-4-叔丁基苯酚和2,4-二甲氧基苯酚在碱性条件下能有效清除超氧阴离子并产生自由基。2-烯丙基-4-叔丁基苯酚表现出最高的细胞毒性活性和DNA合成抑制活性，这可能归因于其疏水自由基反应性。2-烯丙基-4-甲氧基苯酚和2,4-二甲氧基苯酚的抗氧化活性高于3-叔丁基-4-羟基茴香醚（BHA），但所有这些化合物彼此之间表现出相当的细胞毒性活性。这些发现表明丁香酚相关化合物的细胞毒性活性与自由基生成/清除活性之间可能存在联系。
