Chain-locked precursor ion scanning based HPLC–MS/MS for in-depth molecular analysis of lipase-catalyzed transesterification of structured phospholipids containing ω-3 fatty acyl chains

被引:5
作者
Zhang M. [1 ,2 ]
Wang P. [3 ]
Jin D. [2 ]
Jian S. [2 ]
Wu J. [2 ]
Huang M. [2 ]
Xie H. [2 ]
Zhao Q. [3 ]
Yang H. [5 ]
Luo P. [4 ]
Yuan H. [1 ]
Xue J. [2 ]
Shen Q. [1 ,2 ]
机构
[1] First People's Hospital of Linping District, Hangzhou
[2] Collaborative Innovation Center of Seafood Deep Processing, Zhejiang Province Joint Key Laboratory of Aquatic Products Processing, Institute of Seafood, Zhejiang Gongshang University, Hangzhou
[3] Zhoushan Institute of Food & Drug Control, Zhoushan
[4] State Key Laboratories for Quality Research in Chinese Medicines, Faculty of Pharmacy, Macau University of Science and Technology, Macau
[5] Zhejiang Marine Development Research Institute, Zhoushan
基金
中国国家自然科学基金;
关键词
Lipase-catalysis; Lipidomics; Phospholipase; Precursor ion scanning; Transesterification;
D O I
10.1016/j.foodchem.2022.133982
中图分类号
学科分类号
摘要
Lipase-catalyzed transesterification of structured phospholipids (sPLs) is a hot topic, but the structural variation of the fatty acyl chains in intact phospholipids at the molecular level remains unclear to date. The present study explored the detailed characteristics of synthesized phospholipids through high-performance liquid chromatography–tandem mass spectrometry (HPLC–MS/MS) in precursor ion scan mode. The optimal conditions were in-depth inspected and determined for the reaction system, including phospholipase A1 as catalyst, 15% lipase loading, and 1% water content. The sPLs enriched with EPA/DHA were structurally and quantitatively characterized by focusing on the fragments of m/z 301.6 (eicosapentaenoic acid, EPA) and m/z 327.6 (docosahexaenoic acid, DHA), and the results were statistically analyzed using partial least squares discriminant analysis and clustered heatmap hierarchical clustering analysis. PC 38:6 (18:1/20:5), PC 38:7 (18:2/20:5), PC o-40:6 (o-18:0/22:6), and PE 40:8 (18:2/22:6) etc. were revealed as the main variables that were active in the reaction. © 2022 Elsevier Ltd
引用
收藏
相关论文
共 37 条
[1]  
Ang X., Chen H., Xiang J.-Q., Wei F., Quek S.Y., Preparation and functionality of lipase-catalysed structured phospholipid – A review, Trends in Food Science & Technology, 88, pp. 373-383, (2019)
[2]  
Aravindan R., Anbumathi P., (2007)
[3]  
Baeza-Jimenez R., Noriega-Rodriguez J.A., Garcia H.S., Otero C.J., Structured phosphatidylcholine with elevated content of conjugated linoleic acid: Optimization by response surface methodology, European Journal of Lipid Science and Technology, 114, 11, pp. 1261-1267, (2012)
[4]  
Beppu F., Yasuda K., Okada A., Hirosaki Y., Okazaki M., Gotoh N., Comparison of the distribution of unsaturated fatty acids at the sn-2 position of phospholipids and triacylglycerols in marine fishes and mammals, Journal of Oleo Science, (2017)
[5]  
Bispo P., Batista I., Bernardino R.J., Bandarra N.M., Preparation of triacylglycerols rich in omega-3 fatty acids from sardine oil using a Rhizomucor miehei lipase: Focus in the EPA/DHA ratio, Applied Biochemistry and Biotechnology, 172, 4, pp. 1866-1881, (2014)
[6]  
Boselli E., Pacetti D., Lucci P., Frega N.G., Characterization of phospholipid molecular species in the edible parts of bony fish and shellfish, Journal of Agricultural and Food Chemistry, 60, 12, pp. 3234-3245, (2012)
[7]  
Che H., Cui J., Wen M., Xu J., Yanagita T., Wang Q., Wang Y., Long-term effects of docosahexaenoic acid-bound phospholipids and the combination of docosahexaenoic acid-bound triglyceride and egg yolk phospholipid on lipid metabolism in mice, Journal of Ocean University of China, 17, 2, pp. 392-398, (2018)
[8]  
Chen W., Guo W., Gao F., Chen L., Chen S., Li D., Phospholipase A1-Catalysed Synthesis of Docosahexaenoic Acid-Enriched Phosphatidylcholine in Reverse Micelles System, Applied Biochemistry Biotechnology, 182, 3, pp. 1037-1052, (2017)
[9]  
Smith E., pp. 242-249, (2016)
[10]  
Hansen J.B., Olsen J.O., Wilsgard L., Lyngmo V., Svensson B., Comparative effects of prolonged intake of highly purified fish oils as ethyl ester or triglyceride on lipids, haemostasis and platelet function in normolipaemic men, European Journal of Clinical Nutrition, 47, 7, pp. 497-507, (1993)