数字农科院2.0

Orthogonal functional group tagging combined with computational retention time prediction for discovering furan fatty acids in plant oils

文献类型： 外文期刊

作者： Hua Ming Xiao;Xiao Hui Peng;Shuai Zhao;Dilshad Hussain;Qin Feng Zhang;Jian Li Chen;Dan Luo;Fang Wei;Xian Wang

作者机构：

关键词： Chemical tagging;Density functional theory;Furan fatty acid;Liquid chromatography-mass spectrometry;Retention time prediction

期刊名称： Food Chemistry

ISSN： 0308-8146

年卷期： 2025 年 492 卷

页码：

收录情况： SCIE（2025版） ; ; EI（2025版）

摘要： Furan fatty acid (FuFA) exhibits antioxidant and anti-inflammatory properties, thereby reducing cardiovascular risks in humans. However, the availability of chemical standards for free FuFAs are limited. Some of them show poor tolerance toward acidic environments, elevated temperatures, and light exposure. Few accurate and efficient structural elucidation method has been developed for their non-targeted screening in complex matrices. This pilot study describes a novel approach that combines orthogonal functional group tagging with computational retention time (RT) prediction to identify potential free FuFA across different plant oil samples. The tagging of the furan ring skeleton and carboxylic group was achieved by direct condensation using two derivatization reagents, 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide (CMCT) and 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD), respectively. The liquid chromatography-mass spectrometry (LC-MS) analysis of CMCT and PTAD derivatives of furan ring-containing carboxylic acids reveals that the RTs for CMCT derivative exceeded those of PTAD derivatives; CMCT derivatives generated [M-101.0841]+ and [M-125.0841]+ product ions, while PTAD derivatives produced [PTAD]− and [M-43.9898]− product ions. In the presence of straight-chain saturated fatty acids (C8:0-C20:0) within plant oil, computational RTs of putative 151 FuFAs located among C8:0-C20:0, facilitating the establishment of a predicted RT region mapping. It further identified the potential FuFA features picked out through the screening method to minimize false positive results. Although we ultimately not find any free FuFAs from the investigated samples, the results demonstrated that the procedure of FuFA screening dramatically mitigates false positive results during structural elucidation in the case of lack of chemical standards for comparison.

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