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由2-乙酰基吡咯与亚硝酸盐反应衍生的硝基吡咯化合物的致突变性和细胞毒性。

Mutagenicity and cytotoxicity of nitropyrrole compounds derived from the reaction of 2-acetyl pyrrole with nitrite.

作者信息

Wang C J, Lin Y L, Lin J K

机构信息

Institute of Biochemistry, Chung Shan Medical and Dental College, Taichung, Taiwan, Republic of China.

出版信息

Food Chem Toxicol. 1994 Sep;32(9):839-44. doi: 10.1016/0278-6915(94)90161-9.

DOI:10.1016/0278-6915(94)90161-9
PMID:7927082
Abstract

2-Acetylpyrrole (AP) is a product of model browning systems, and has been isolated as a major flavour component of many foods. Reaction of AP with nitrite produces two N-nitropyrrole compounds, 1-nitro-2-acetyl-pyrrole (NAP) and 1,3,5-trinitro-2-acetylpyrrole (TNAP), the chemical structures of which have been confirmed by spectral studies, including UV mass, nuclear magnetic resonance, infra-red and elemental analysis (EA). NAP and TNAP are moderately mutagenic to the Salmonella strains TA98 and TA100 in the absence of a mammalian activation system and are markedly cytotoxic to mouse C3H10T1/2 cells. These results suggest that the formation of direct-acting mutagens of nitro-derivatives may take place in nitrite-containing food or in vivo by nitrosation following ingestion of AP.

摘要

2-乙酰基吡咯(AP)是模拟褐变体系的产物,并且已被分离出来作为许多食品的主要风味成分。AP与亚硝酸盐反应生成两种N-硝基吡咯化合物,1-硝基-2-乙酰基吡咯(NAP)和1,3,5-三硝基-2-乙酰基吡咯(TNAP),其化学结构已通过光谱研究得以证实,包括紫外质谱、核磁共振、红外光谱和元素分析(EA)。在不存在哺乳动物活化系统的情况下,NAP和TNAP对沙门氏菌菌株TA98和TA100具有中等程度的致突变性,并且对小鼠C3H10T1/2细胞具有明显的细胞毒性。这些结果表明,在含亚硝酸盐的食物中或体内,摄入AP后通过亚硝化作用可能会形成硝基衍生物的直接作用诱变剂。

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Mutagenicity and cytotoxicity of nitropyrrole compounds derived from the reaction of 2-acetyl pyrrole with nitrite.由2-乙酰基吡咯与亚硝酸盐反应衍生的硝基吡咯化合物的致突变性和细胞毒性。
Food Chem Toxicol. 1994 Sep;32(9):839-44. doi: 10.1016/0278-6915(94)90161-9.
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引用本文的文献

1
Scientific opinion on flavouring group evaluation 77, revision 3 (FGE.77Rev3): consideration of pyridine, pyrrole and quinoline derivatives evaluated by JECFA (63rd meeting) structurally related to pyridine, pyrrole, indole and quinoline derivatives evaluated by EFSA in FGE.24Rev2.关于调味剂组评估77修订版3(FGE.77Rev3)的科学意见:对食品添加剂联合专家委员会(第63次会议)评估的吡啶、吡咯和喹啉衍生物的考量,这些衍生物在结构上与欧洲食品安全局在FGE.24Rev2中评估的吡啶、吡咯、吲哚和喹啉衍生物相关。
EFSA J. 2018 Apr 25;16(4):e05226. doi: 10.2903/j.efsa.2018.5226. eCollection 2018 Apr.
2
N-Nitroso-N-(3-keto-1,2-butanediol)-3'-nitrotyramine. A new genotoxic agent derived from the reaction of tyrosine and glucose in the presence of sodium nitrite.N-亚硝基-N-(3-酮基-1,2-丁二醇)-3'-硝基酪氨酸。一种由酪氨酸和葡萄糖在亚硝酸钠存在下反应生成的新型遗传毒性剂。
Arch Toxicol. 1995;70(1):10-5. doi: 10.1007/s002040050242.