Key Laboratory in Flavor & Fragrance Basic Research, Zhengzhou Tobacco Research Institute, China National Tobacco Corporation, Zhengzhou 450001, China.
Center of Advanced Analysis and Gene Sequencing, Zhengzhou University, Zhengzhou 450001, China.
Molecules. 2022 May 4;27(9):2942. doi: 10.3390/molecules27092942.
It is well known that organic acids (OAs) could affect the flavour of fruit juices and beverages. However, the molecular mechanism of aroma release is still unclear. In this study, the effects of citric acid (CA), L-(-)-malic acid (MA) and L-lactic acid (LA) on the release of six selected esters and their sensory perception were investigated by means of HS-GC-MS analyses and odour detection threshold determination, respectively. Meanwhile, the density functional theory (DFT) calculation was employed to explore the interaction modes between esters and OAs. HS-GC-MS analyses showed that the concentration and the type of OAs regulated the release of esters. The results were basically consistent with the detection threshold change of those esters. The DFT calculation suggested that the main intermolecular interaction was hydrogen bonds, and several esters could form a ternary ring structure with OAs through hydrogen bonds. The interactions can induce the different release behaviours of esters in OAs water solution. The number of carboxyl functional groups in OAs and the spatial conformation of esters appeared to influence the magnitude of the interaction. The above results demonstrated the mechanism of OAs affecting the release of esters and indicated a possible flavour control way by using different OAs and OA concentrations.
众所周知,有机酸(OAs)会影响果汁和饮料的风味。然而,香气释放的分子机制仍不清楚。在这项研究中,通过顶空-气相色谱-质谱(HS-GC-MS)分析和气味检测阈值测定,分别研究了柠檬酸(CA)、L-(-)-苹果酸(MA)和 L-乳酸(LA)对 6 种选定酯类的释放及其感官感知的影响。同时,采用密度泛函理论(DFT)计算来探讨酯类与 OAs 之间的相互作用模式。HS-GC-MS 分析表明,OAs 的浓度和类型调节酯类的释放。结果与这些酯类的检测阈值变化基本一致。DFT 计算表明,主要的分子间相互作用是氢键,几种酯类可以通过氢键与 OAs 形成三元环结构。相互作用可以诱导酯类在 OAs 水溶液中的不同释放行为。OAs 中的羧基官能团数量和酯类的空间构象似乎影响相互作用的大小。上述结果表明了 OAs 影响酯类释放的机制,并为通过使用不同的 OAs 和 OAs 浓度来控制风味提供了一种可能的方法。