Satoh K, Sakagami H, Yokoe I, Kochi M, Fujisawa S
Analysis Center, School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
Anticancer Res. 1998 Jan-Feb;18(1A):425-8.
The radical modulating activity of 2-methoxy-4-(2-propenyl)phenol (eugenol), 2-t-butyl-4-methoxy-phenol (BHA), and their dimers (bis-eugenol, bis-BHA) was investigated, using ESR spectroscopy. Eugenol produced radicals in alkaline solutions, and enhanced the radical intensity of both sodium-L-ascorbate and sodium 5,6-benzylidene-L-ascorbate. BHA has similar, but slightly lower activity, and their dimers were inactive. Their ability to scavenge the superoxide anion (O2-), generated by hypoxanthine and xanthine oxidase reaction, was in the order of eugenol > bis-eugenol > BHA > bis-BHA. The relative radical intensity among these compounds was paralleled by their cytotoxic activity. The present study demonstrates that eugenol and BHA were very reactive with radicals and their reactivity was considerably reduced by dimerization. The applicability of the dimerized eugenol in dentistry was discussed.
使用电子自旋共振光谱法研究了2-甲氧基-4-（2-丙烯基）苯酚（丁香酚）、2-叔丁基-4-甲氧基苯酚（丁基羟基茴香醚，BHA）及其二聚体（双丁香酚、双BHA）的自由基调节活性。丁香酚在碱性溶液中产生自由基，并增强了L-抗坏血酸钠和5,6-亚苄基-L-抗坏血酸钠的自由基强度。BHA具有相似但略低的活性，且它们的二聚体无活性。它们清除由次黄嘌呤和黄嘌呤氧化酶反应产生的超氧阴离子（O2-）的能力顺序为：丁香酚>双丁香酚>BHA>双BHA。这些化合物之间的相对自由基强度与其细胞毒性活性平行。本研究表明，丁香酚和BHA与自由基反应非常活跃，且其二聚化会使其反应性显著降低。讨论了二聚丁香酚在牙科中的适用性。
