Tian Yunong, Zhou Yanhui, Li Lu, Huang Chuanqing, Lin Lin, Li Changzhu, Ye Yong
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China.
Hunan Singular Biological Technology Co. Ltd, Changsha, China.
J Sci Food Agric. 2024 Jan 30;104(2):942-955. doi: 10.1002/jsfa.12982. Epub 2023 Oct 6.
Nutritional and functional qualities and applications of structured lipids (SL) depend on the composition and molecular structure of fatty acids in the glycerol backbone of triacylglycerol (TAG). However, the relationship between the substrate composition and physicochemical qualities of SL has not been revealed. The investigation aims to disclose the effect of substrate composition on the physicochemical properties of medium-long-medium structured lipids (MLM-SLs) by enzymatic interesterification of Lipozyme TLIM/RMIM.
The medium-long-chain triacylglycerol (MLCT) yield could reach 70.32%, including 28.98% CaLCa (1,3-dioctonyl-2-linoleoyl glyceride) and 24.34% CaOCa (1,3-didecanoyl-2-oleoyl glyceride). The sn-2 unsaturated fatty acid composition mainly depended on long-chain triacylglycerol (LCT) in the substrate. The increased carbon chain length and double bond in triacylglycerol decreased its melting and crystallization temperature. The balanced substrate composition of MCT/LCT increased the size and finer crystals. Molecular docking simulation revealed that the MLCT molecule mainly interacted with the catalytic triplets of Lipozyme TLIM (Arg81-Ser83-Arg84) and the Lipozyme RMIM (Tyr183-Thr226-Arg262) by OH bond. The oxygen atom of the ester on the MLCT molecule was primarily bound to the hydrogen of hydroxyl and amino groups on the binding sites of Lipozyme TLIM/RMIM. The intermolecular interplay between MLCT and Lipozyme RMIM is more stable than Lipozyme TLIM due to the formation of lower binding affinity energy.
This research clarifies the interaction mechanism between MLCT molecules and lipases, and provides an in-depth understanding of the relationship between substrate composition, molecular structure and physicochemical property of MLM-SLs. © 2023 Society of Chemical Industry.
结构化脂质(SL)的营养和功能特性及其应用取决于三酰甘油(TAG)甘油主链中脂肪酸的组成和分子结构。然而,SL的底物组成与其物理化学性质之间的关系尚未明确。本研究旨在通过Lipozyme TLIM/RMIM的酶促酯交换反应,揭示底物组成对中-长-中结构化脂质(MLM-SLs)物理化学性质的影响。
中长链三酰甘油(MLCT)产率可达70.32%,其中包括28.98%的CaLCa(1,3-二辛酰基-2-亚油酰基甘油酯)和24.34%的CaOCa(1,3-二十二酰基-2-油酰基甘油酯)。sn-2位不饱和脂肪酸组成主要取决于底物中的长链三酰甘油(LCT)。三酰甘油中碳链长度和双键的增加会降低其熔点和结晶温度。中链甘油三酯/长链甘油三酯(MCT/LCT)的底物组成平衡会增加晶体尺寸并使其更细小。分子对接模拟表明,MLCT分子主要通过OH键与Lipozyme TLIM(Arg81-Ser83-Arg84)和Lipozyme RMIM(Tyr183-Thr226-Arg262)的催化三联体相互作用。MLCT分子上酯的氧原子主要与Lipozyme TLIM/RMIM结合位点上羟基和氨基的氢结合。由于形成了较低的结合亲和力能量,MLCT与Lipozyme RMIM之间的分子间相互作用比Lipozyme TLIM更稳定。
本研究阐明了MLCT分子与脂肪酶之间的相互作用机制,并深入了解了MLM-SLs的底物组成、分子结构和物理化学性质之间的关系。© 2023化学工业协会。