Rashid K A, Mullin C A, Mumma R O
Mutat Res. 1986 Mar;169(3):71-9. doi: 10.1016/0165-1218(86)90086-8.
31 p-monosubstituted chalcones (E-1, 3-diphenylpropene-1-one) and the corresponding oxides (E-1-benzoyl-2-phenyloxirane) were tested for mutagenic activity on two strains of Salmonella typhimurium (TA98 and TA100) with and without rat liver microsomal and cytosolic enzymes. Highest mutagenicity (3.0 revertants/nmole in either strain) was seen with the 4-nitrochalcone, especially after S9 activation. Epoxidation, in general, increased the mutagenic activity of the respective chalcone. Benzoyl (4') substituted chalcones and their oxides with an electron-withdrawing substituent (e.g., nitro, fluoro) usually had higher activity than their phenyl (4) substituted counterparts, whereas the converse was the case with electron-donating substituents (e.g., acetamido, methoxy). Further multiple factorial analysis revealed that increasing hydrophilicity as indicated by the Hansch pi parameter, and resonance electronic contributions were more important than other factors including steric terms in explaining the mutagenicity of these compounds. Mutagenic effects of some chalcone oxides, particularly the 4-methoxy derivative, were markedly decreased by S9 treatment. The consequence of the weak-to-moderate mutagenicity of these compounds to dietary intake of hydroxylated and methoxylated chalcones is discussed.
对31种对单取代查耳酮（E-1,3-二苯基丙烯-1-酮）及其相应的氧化物（E-1-苯甲酰基-2-苯基环氧乙烷）在有和没有大鼠肝微粒体及胞质酶的情况下，对两株鼠伤寒沙门氏菌（TA98和TA100）进行了致突变活性测试。在4-硝基查耳酮中观察到最高的致突变性（任一菌株中为3.0回复突变体/纳摩尔），尤其是在S9活化后。一般来说，环氧化增加了相应查耳酮的致突变活性。苯甲酰基（4'）取代的查耳酮及其带有吸电子取代基（如硝基、氟）的氧化物通常比其苯基（4）取代的对应物具有更高的活性，而对于供电子取代基（如乙酰胺基、甲氧基）则情况相反。进一步的多因素分析表明，如Hansch π参数所示的亲水性增加以及共振电子贡献在解释这些化合物的致突变性方面比包括空间位阻项在内的其他因素更重要。一些查耳酮氧化物，特别是4-甲氧基衍生物的致突变作用在S9处理后明显降低。讨论了这些化合物弱至中等致突变性对饮食中羟基化和甲氧基化查耳酮摄入量的影响。
