College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China; Laboratory of Quality and Safety Risk Assessment for Aquatic Products on Storage and Preservation (Shanghai), Ministry of Agriculture, Shanghai 201306, China.
School of Food Science and Technology, Jiangnan University, Wuxi, China.
Food Chem. 2021 Oct 1;358:129843. doi: 10.1016/j.foodchem.2021.129843. Epub 2021 Apr 20.
The inhibitory effects of seven polyphenols on 3-chloropropane-1,2-diol fatty acid esters (3-MCPDE) formation were investigated in palm oil models. Results showed that there was not a positive significant correlation between the free-radical scavenging activities of the tested compounds and their 3-MCPDE-formation inhibitory activities; puerarin, with weak antioxidant activity, showed the highest inhibitory capacity. Moreover, puerarin reduced the content of glycidol and glycidyl esters (GEs), two key intermediates of 3-MCPDE formation in the oil models; and a puerarin-adduct was discovered in the oil fortified with glycidol or GEs, with its structure elucidated by LC-MS/MS and comparison with newly synthesized ones. Based on its chemical structure, we proposed that puerarin, at least in part, reacted with glycidol and GEs to inhibit 3-MCPDE formation. In addition, the formed compound, puerarin-7-O-propanediol was identified in the potato chips frying system, further confirming reacting with glycidol/GEs as a key mechanism of puerarin to inhibit 3-MCPDE formation.
七种多酚对棕榈油模型中 3-氯-1,2-丙二醇脂肪酸酯（3-MCPDE）形成的抑制作用进行了研究。结果表明，测试化合物的自由基清除活性与其 3-MCPDE 形成抑制活性之间没有正相关关系；具有弱抗氧化活性的葛根素表现出最高的抑制能力。此外，葛根素降低了油模型中 3-MCPDE 形成的关键中间体缩水甘油和缩水甘油酯（GEs）的含量；并且在添加缩水甘油或 GEs 的油中发现了一种葛根素加合物，通过 LC-MS/MS 及其与新合成的化合物的比较来阐明其结构。基于其化学结构，我们提出葛根素至少部分与缩水甘油和 GEs 反应以抑制 3-MCPDE 的形成。此外，在薯条油炸体系中鉴定出形成的化合物葛根素-7-O-丙二醇，进一步证实了与缩水甘油/GEs 反应是葛根素抑制 3-MCPDE 形成的关键机制。
