College of Food Science and Engineering , South China University of Technology , Guangzhou , Guangdong 510640 , People's Republic of China.
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety , Guangzhou , Guangdong 510640 , People's Republic of China.
J Agric Food Chem. 2019 Aug 14;67(32):9050-9059. doi: 10.1021/acs.jafc.9b01182. Epub 2019 Aug 2.
The control of 2,3-dihydro-3,5-dihydroxy-6-methyl-4()-pyran-4-one (DDMP) formation in the Maillard reaction is important to improve the thermally treated food quality as a result of its intense bitterness and potential toxicity. In this work, phenolic acids, such as gallic, protocatechuic, caffeic, and ferulic acids, were applied to modulate DDMP formation in a microaqueous glucose-proline model. The formation of DDMP was inhibited at low concentrations (from 0.1 to 5.0 mM) while enhanced at 10.0 mM gallic, protocatechuic, and caffeic acids. Ferulic acid always inhibited DDMP formation as a result of the absence of catechol groups on its benzene ring. The result indicated that the control of DDMP formation depended upon the concentration and chemical structures of phenolic acids, such as the number of hydroxyl groups. Further studies indicated that the hydroxyl distribution of phenolic acids regulated the peroxide formation in the model reaction system and further changed the development of the oxidation reaction, which affected the degradation of glucose via caramel or Maillard reaction, Amadori rearrangement product oxidation, and 1-deoxyglucosone degradation to form the intermediates.
2,3-二氢-3,5-二羟基-6-甲基-4（H）-吡喃-4-酮（DDMP）是美拉德反应中的苦味和潜在毒性物质，其生成的控制对于改善热处理食品的品质非常重要。在这项工作中，应用了几种酚酸，如没食子酸、原儿茶酸、咖啡酸和阿魏酸，来调节微水葡萄糖-脯氨酸模型中 DDMP 的形成。DDMP 的形成在低浓度（0.1-5.0mM）下受到抑制，而在 10.0mM 没食子酸、原儿茶酸和咖啡酸时则增强。由于阿魏酸苯环上没有邻苯二酚基团，因此其始终抑制 DDMP 的形成。结果表明，DDMP 形成的控制取决于酚酸的浓度和化学结构，如羟基的数量。进一步的研究表明，酚酸的羟基分布调节了模型反应体系中的过氧化物形成，并进一步改变了氧化反应的发展，这影响了葡萄糖通过焦糖或美拉德反应、Amadori 重排产物氧化和 1-脱氧葡萄糖降解形成中间体的降解。
