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丁基羟基茴香醚及其代谢产物与某些芳胺的反应:产物致突变性研究。

The reaction of butylated hydroxyanisole and its metabolites with some arylamines: investigations of product mutagenicity.

作者信息

Kalus W H, Münzner R, Filby W G

机构信息

Federal Institute for Nutrition Research, Engesserstrasse 20, Karlsruhe, Germany.

出版信息

Environ Health Perspect. 1994 Jan;102(1):96-9. doi: 10.1289/ehp.9410296.

DOI:10.1289/ehp.9410296
PMID:9719675
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1567239/
Abstract

We examined t-butylhydroquinone (t-BHQ) and t-butylquinone (t-BuQ), two of the major microsomal metabolites of the synthetic antioxidant butylated hydroxyanisole (BHA), for their ability to react with the xenobiotic arylamines aniline and N-methylaniline. A number of substances were isolated by thin-layer chromatography. The main products were quantitatively evaluated and their structures assigned. BHA and t-BHQ yielded reaction products with anilines only in the presence of an oxidant such as iodate (KIO3). We used the Salmonella/microsome mutagenicity assay to test the new compounds for mutagenic activity. The reaction products gave no evidence of mutagenicity in the S. typhimurium strains TA98 and TA100, with or without metabolic activation. In some instances the substituted quinone products are less toxic than t-BuQ alone.

摘要

我们研究了叔丁基对苯二酚(t-BHQ)和叔丁基醌(t-BuQ),它们是合成抗氧化剂丁基羟基茴香醚(BHA)的两种主要微粒体代谢产物,考察了它们与外源性芳胺苯胺和N-甲基苯胺发生反应的能力。通过薄层色谱法分离出了多种物质。对主要产物进行了定量评估并确定了其结构。BHA和t-BHQ仅在存在诸如碘酸盐(KIO3)等氧化剂的情况下才与苯胺生成反应产物。我们采用沙门氏菌/微粒体诱变性试验来检测这些新化合物的诱变活性。无论有无代谢活化,反应产物在鼠伤寒沙门氏菌TA98和TA100菌株中均未显示出诱变活性。在某些情况下,取代醌产物的毒性低于单独的t-BuQ。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3ae/1567239/0d1395f8506c/envhper00389-0097-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3ae/1567239/0d1395f8506c/envhper00389-0097-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3ae/1567239/0d1395f8506c/envhper00389-0097-a.jpg

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本文引用的文献

1
Revised methods for the Salmonella mutagenicity test.沙门氏菌致突变性试验的修订方法。
Mutat Res. 1983 May;113(3-4):173-215. doi: 10.1016/0165-1161(83)90010-9.
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Metabolism of 3-tert-butyl-4-hydroxyanisole to 3-tert-butyl-4,5-dihydroxyanisole by rat liver microsomes.
Cancer Res. 1985 Apr;45(4):1507-10.
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Assessment of the risk of formation of carcinogenic N-nitroso compounds from dietary precursors in the stomach.评估胃中膳食前体形成致癌性N-亚硝基化合物的风险。
Food Chem Toxicol. 1987 Jan;25(1):91-108. doi: 10.1016/0278-6915(87)90311-5.
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Food Chem Toxicol. 1986 Aug;24(8):847-9. doi: 10.1016/0278-6915(86)90075-x.
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Mutagens formed from butylated hydroxyanisole treated with nitrite under acidic conditions.
Mutat Res. 1987 Feb;176(2):179-84. doi: 10.1016/0027-5107(87)90048-0.
7
Butylated hydroxyanisole, butylated hydroxytoluene and tert.-butylhydroquinone are not mutagenic in the Salmonella/microsome assay using new tester strains.在使用新型测试菌株的沙门氏菌/微粒体试验中,丁基羟基茴香醚、丁基羟基甲苯和叔丁基对苯二酚不具有致突变性。
Mutat Res. 1988 Jul;208(3-4):207-11. doi: 10.1016/0165-7992(88)90062-0.
8
Production of reactive oxygen species due to metabolic activation of butylated hydroxyanisole.由于丁基羟基茴香醚的代谢活化而产生活性氧。
Toxicology. 1989 Dec 1;59(2):179-94. doi: 10.1016/0300-483x(89)90056-5.
9
Chemical reactions of organic compounds on clay surfaces.有机化合物在黏土表面的化学反应。
Environ Health Perspect. 1989 Nov;83:205-14. doi: 10.1289/ehp.8983205.
10
Isolation and characterization of some products of the BHA-nitrite reaction: examination of their mutagenicity.丁基羟基茴香醚-亚硝酸盐反应某些产物的分离与特性鉴定:对其致突变性的检测
Food Addit Contam. 1990 Mar-Apr;7(2):223-33. doi: 10.1080/02652039009373886.