The Dept. of Food Science and Engineering, Jinan Univ., Guangzhou, 510632, China.
J Food Sci. 2018 Oct;83(10):2662-2668. doi: 10.1111/1750-3841.14355. Epub 2018 Sep 19.
3-Aminopropanamide (3-APA) is the direct precursor of acrylamide produced in the Maillard reaction between asparagine and reducing sugars. In this research, we found that 3-APA could reduce acrylamide by the formation of adducts between acrylamide and 3-APA via Michael addition. The effects of temperature, heating duration and 3-APA/acrylamide ratio on the reduction of acrylamide were investigated. Addition of 3-APA to acrylamide at a molar ratio of 5:3 at 160 °C for 20 min reduced acrylamide by up to 47.29%. The major adduct was identified as 3,3',3'-nitrilotris, and its cytotoxicity on Caco-2 cells was evaluated to be much lower than acrylamide. The viability of Caco-2 cells retained at 88.31% and 86.43% after incubation with 16 mM 3,3',3'-nitrilotris for 24 and 48 hr, respectively, while those incubated with the same concentration of acrylamide were 23.33% and 19.12%, respectively.
The current study reported 3-APA could reduce acrylamide through the Micheal addition reaction between 3-APA and acrylamide. The adduct showed significantly reduced cytotoxicity compared to acrylamide. The research is critical in evaluation and control of food contaminants. The results brought new insights in the area of food safety, especially in the mechanism researches on formation and mitigation of endogenous contaminants in thermal-processed foods.
3-氨基丙酰胺（3-APA）是天冬酰胺和还原糖之间美拉德反应产生丙烯酰胺的直接前体。在这项研究中，我们发现 3-APA 可以通过丙烯酰胺和 3-APA 之间的迈克尔加成反应形成加合物来减少丙烯酰胺。研究了温度、加热时间和 3-APA/丙烯酰胺比对丙烯酰胺还原的影响。在 160°C 下将 3-APA 以 5:3 的摩尔比添加到丙烯酰胺中 20 分钟，可以将丙烯酰胺减少多达 47.29%。主要加合物被鉴定为 3,3',3'-三嗪，其对 Caco-2 细胞的细胞毒性明显低于丙烯酰胺。孵育 16mM 3,3',3'-三嗪 24 和 48 小时后，Caco-2 细胞的存活率分别保持在 88.31%和 86.43%，而孵育相同浓度丙烯酰胺的细胞存活率分别为 23.33%和 19.12%。
本研究报道 3-APA 可以通过 3-APA 和丙烯酰胺之间的迈克尔加成反应减少丙烯酰胺。加合物的细胞毒性明显低于丙烯酰胺。该研究对食品污染物的评估和控制具有重要意义。研究结果为食品安全领域带来了新的见解，特别是在热加工食品中内源性污染物形成和缓解的机制研究方面。
