College of Food Science and Technology, Shanghai Ocean University, Shanghai, 201306, China.
Institute for Agro-food Standards and Testing Technology, Shanghai Academy of Agricultural Sciences, Shanghai, 201106, China.
Food Res Int. 2023 Feb;164:112465. doi: 10.1016/j.foodres.2023.112465. Epub 2023 Jan 6.
Harman and norharman were the most abundant β-carboline-type heterocyclic amines (HCAs) detected in various foodstuffs. Unsaturated fatty acids in foods may undergo rapid oxidative deterioration during transportation, storage and heat treatment, forming reactive carbonyl species (RCS). This work studied the effects of acrolein, a highly reactive RCS, on the formation of harman and norharman in the tryptophan model system. Results showed that 0.005, 0.01, 0.015, 0.02, 0.05, 0.1 and 0.2 mmol of acrolein led to harman production increased by 528 %, 752 %, 981 %, 1172 %, 1375 %, 1288 % and 768 % respectively, and led to norharman formation increased by 116 %, 129 %, 152 %, 169 %, and 197 %, 185 % and 157 %, respectively. Furthermore, acrolein addition reduced the residue of tryptophan (up to 63.19 %), but increased the level of the intermediates including formaldehyde (up to 352 %), acetaldehyde (up to 491 %), (1S,3S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (MTCA, up to 1936 %), and 1,2,3,4-tetrahydro-β-carboline-3-carboxylicacid (THCA, up to 2142 %) in the tryptophan model system. Acrolein might react with tryptophan, harman and norharman to eliminate them directly. These data suggested that acrolein may contribute to harman and norharman formation through participating in the above complex chemical reactions. In addition, the content of harman and norharman produced in roast beef patties made of minced beef oxidized for 2, 4, 6, 8, and 10 days increased by 118 %, 188 %, 267 %, 137 %, and 48 %, respectively, and led to norharman formation increased by 140 %, 132 %, 90 %, 86 %, and 74 %, respectively compared with those made of fresh minced beef, which further illustrated that lipid oxidation products potentially contributed to harman and norharman formation.
哈尔曼碱和去氢哈尔曼碱是各种食品中含量最丰富的β-咔啉型杂环胺（HCAs）。食物中的不饱和脂肪酸在运输、储存和热处理过程中可能会迅速发生氧化劣变，形成反应性羰基物质（RCS）。本工作研究了丙烯醛这种高度反应性的 RCS 对色氨酸模型体系中哈尔曼碱和去氢哈尔曼碱形成的影响。结果表明，0.005、0.01、0.015、0.02、0.05、0.1 和 0.2mmol 的丙烯醛分别使哈尔曼碱的产量增加了 528%、752%、981%、1172%、1375%、1288%和 768%，使去氢哈尔曼碱的产量增加了 116%、129%、152%、169%、197%、185%和 157%。此外，丙烯醛的添加降低了色氨酸的残留量（高达 63.19%），但增加了包括甲醛（高达 352%）、乙醛（高达 491%）、（1S,3S）-1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸（MTCA，高达 1936%）和 1,2,3,4-四氢-β-咔啉-3-羧酸（THCA，高达 2142%）在内的中间体水平。丙烯醛可能与色氨酸、哈尔曼碱和去氢哈尔曼碱反应，直接消除它们。这些数据表明，丙烯醛可能通过参与上述复杂的化学反应而有助于哈尔曼碱和去氢哈尔曼碱的形成。此外，用氧化 2、4、6、8 和 10 天的碎牛肉制成的烤牛肉饼中产生的哈尔曼碱和去氢哈尔曼碱的含量分别增加了 118%、188%、267%、137%和 48%，与用新鲜碎牛肉制成的相比，去氢哈尔曼碱的形成量分别增加了 140%、132%、90%、86%和 74%，这进一步说明了脂质氧化产物可能有助于哈尔曼碱和去氢哈尔曼碱的形成。
