Ogawa S, Hirayama T, Fujioka Y, Ozasa S, Tokuda M, Hirai K, Fukui S
Kyoto Pharmaceutical University, Japan.
Mutat Res. 1987 Sep;192(1):37-46. doi: 10.1016/0165-7992(87)90123-0.
The effect of quercetin on the mutagenicity of 32 kinds of aromatic amines and their acetamides were investigated using Salmonella typhimurium TA98 with a mammalian metabolic activation system (S9 mix). Quercetin enhanced the mutagenicity of the tricyclic aromatic amines (aminofluorene, aminoanthracene and aminophenanthrene) and their acetamides by 1.2-5.9-fold. Whereas, quercetin depressed the mutagenicity of aniline derivatives, biphenyl derivatives, and bi- and tetra-cyclic amino derivatives. The modulation of mutagenicity of Trp-P-1, Trp-P-2, Glu-P-1 and Glu-P-2 (heterocyclic amines) by quercetin were liable to be affected by the content of S9 in the S9 mix. It seems that quercetin does not have the same effect as norharman, because quercetin did not enhance the mutagenicity of aniline. It is suggested that the modulation of the mutagenicity of aromatic amines and acetamides is caused by the modulation of the balance between the mutagenic activation and inactivation in the metabolism of these amines and acetamides in the presence of quercetin. In this modulation, quercetin may participate through its effects on the promotion of N-hydroxylation and the inhibition of arylhydroxylation and transacylation. The presence of tricyclic aromatic rings of amines and acetamides is a structural requirement for the mutagenicity enhancement by quercetin.
利用鼠伤寒沙门氏菌TA98和哺乳动物代谢活化系统（S9混合液），研究了槲皮素对32种芳香胺及其酰胺类化合物致突变性的影响。槲皮素使三环芳香胺（氨基芴、氨基蒽和氨基菲）及其酰胺类化合物的致突变性增强了1.2至5.9倍。然而，槲皮素降低了苯胺衍生物、联苯衍生物以及二环和四环氨基衍生物的致突变性。槲皮素对Trp-P-1、Trp-P-2、Glu-P-1和Glu-P-2（杂环胺）致突变性的调节容易受到S9混合液中S9含量的影响。似乎槲皮素与去甲哈尔满的作用不同，因为槲皮素并未增强苯胺的致突变性。提示芳香胺及其酰胺类化合物致突变性的调节是由于在槲皮素存在下，这些胺类和酰胺类化合物代谢过程中致突变活化与失活之间平衡的调节所致。在这种调节中，槲皮素可能通过其对N-羟基化促进作用以及芳基羟基化和转酰基化抑制作用来参与。胺类和酰胺类化合物中三环芳香环的存在是槲皮素增强致突变性的结构要求。
