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Discovery of N-L-Lactoyl-L-Trp as a Bitterness Masker via Structure-Based Virtual Screening and a Sensory Approach

文献类型： 外文期刊

作者： Wu, Jing 1 ; Zhao, Junpeng 3 ; Zhou, Yubo 3 ; Cui, Chun 1 ; Xu, Jucai 4 ; Li, Laihao 2 ; Feng, Yunzi 1 ;

作者机构： 1.South China Univ Technol, Sch Food Sci & Technol, Guangzhou 510640, Peoples R China

2.Chinese Acad Fishery Sci, Minist Agr & Rural Affairs, Natl R&D Ctr Aquat Prod Proc, Key Lab Aquat Prod Proc,South China Sea Fisheries, Guangzhou 510300, Peoples R China

3.South China Univ Technol, Fac Mat Sci & Engn, Guangzhou 510640, Peoples R China

4.Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Peoples R China

5.Wuyi Univ, Int Healthcare Innovat Inst Jiangmen, Jiangmen 529020, Peoples R China

关键词： N-l-Lac-l-Trp; virtual screening; bitterness-masking effect; quantum mechanics

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：6.1； 五年影响因子：6.3 ）

ISSN： 0021-8561

年卷期： 2023 年

页码：

收录情况： SCI

摘要： N-Lactoyl-amino acid derivatives (N-Lac-AAs) are of increasing interest as potential taste-active compounds. The complexity and diversity of N-Lac-AAs pose a significant challenge to the effective discovery of taste-active N-Lac-AAs. Therefore, a structure-based virtual screening was used to identify taste-active N-Lac-AAs. Virtual screening results showed that N-lactoyl-hydrophobic amino acids had a higher affinity for taste receptors, specifically N-L-Lac-L-Trp. And then, N-L-Lac-L-Trp was synthesized in yields of 22.3% by enzymatic synthesis in the presence of L-lactate and L-Trp, and its chemical structure was confirmed by MS/MS and one-dimensional (1D) and two-dimensional (2D) NMR. Sensory evaluation revealed that N-L-Lac-L-Trp had a significant taste-masking effect on quinine, D-salicin, caffeine, and L-Trp, particularly L-Trp and caffeine. N-L-Lac-L-Trp had a better masking effect on the higher concentration of bitter compounds. It reduced the bitterness of caffeine (500 mg/L) and L-Trp (1000 mg/L) by approximately 20 and 26%, respectively. The result of the ligand-receptor interaction and a quantum mechanical analysis showed that N-L-Lac-L-Trp increased the binding affinity to the bitter receptor mainly through hydrogen bonding and lowering the electrostatic potential.

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