Lin J K, Lee S F
Institute of Biochemistry, College of Medicine, National Taiwan University, Taipei.
Mutat Res. 1992 Oct;269(2):217-24. doi: 10.1016/0027-5107(92)90202-d.
The hydrolytic products of lignins, humic acids and industrial waste including hydroquinone, catechol, resorcinol, pyrogallol and 1,2,4-benzenetriol are widely distributed in water sources. These polyphenols can interact with chlorine or nitrite to yield new derivatives. Generally, these new products possess more mutagenic potential than their original compounds. Furthermore, the mutagenicity of these polyphenols and their derivatives can be dramatically reduced by rodent liver microsomal enzymes (S9). The mutagenicity of polyphenols is in this order: hydroquinone greater than 1,2,4-benzenetriol greater than pyrogallol, while catechol, resorcinol and phloroglucinol are non-mutagenic. The ultimate product of chlorination or nitrosation of hydroquinone has been identified to be p-benzoquinone. The formation of active oxygen species including superoxide anion and hydrogen peroxide by polyphenols has been demonstrated and this may contribute partly to the molecular mechanisms of polyphenol mutagenicity.
木质素、腐殖酸以及包括对苯二酚、邻苯二酚、间苯二酚、连苯三酚和1,2,4-苯三酚在内的工业废料的水解产物广泛分布于水源中。这些多酚类物质可与氯或亚硝酸盐发生相互作用，生成新的衍生物。一般来说，这些新产品比其原始化合物具有更强的诱变潜力。此外，这些多酚类物质及其衍生物的诱变性可被啮齿动物肝微粒体酶（S9）显著降低。多酚类物质的诱变性顺序为：对苯二酚大于1,2,4-苯三酚大于连苯三酚，而邻苯二酚、间苯二酚和间苯三酚无诱变作用。已确定对苯二酚氯化或亚硝化的最终产物为对苯醌。多酚类物质可形成包括超氧阴离子和过氧化氢在内的活性氧，这可能在一定程度上有助于解释多酚类物质诱变性的分子机制。
