ISOF, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy.
Chem Res Toxicol. 2012 Mar 19;25(3):687-94. doi: 10.1021/tx200467c. Epub 2012 Feb 10.
Eicosapentaenoic acid (EPA) is a polyunsaturated fatty acid present in fish oils used for omega-3 enriched diets. The natural cis double bond geometry can be transformed to the trans configuration during the deodorization process utilized in the food industry. The analytical discrimination of the possible five monotrans regioisomers represents a limiting step for the recognition and structure-activity relationship in connection with the harmful effects of trans fatty acids in health. We carried out a dual synthetic strategy, providing new access to monotrans EPA isomers and valuable information on GC and NMR characteristics for further applications in metabolomics and lipidomics. This small library was used as an analytical reference for isomer determination in deodorized fish oils and the follow-up of rats fed fish oil diets, evidencing for the first time that monotrans EPA isomers are incorporated in liver mitochondrial membranes after dietary intake.
二十碳五烯酸（EPA）是一种多不饱和脂肪酸，存在于鱼油中，用于ω-3 强化饮食。在食品工业中使用的脱臭过程中，天然顺式双键几何形状可以转化为反式构型。在与反式脂肪酸对健康的有害影响有关的识别和结构-活性关系方面，对可能的五种单反式区域异构体的分析鉴别代表了一个限制步骤。我们进行了双重合成策略，为单反式 EPA 异构体提供了新的途径，并提供了有关 GC 和 NMR 特征的有价值信息，可进一步应用于代谢组学和脂质组学。这个小文库被用作分析参考，用于确定脱臭鱼油中的异构体，并跟踪喂食鱼油饮食的大鼠，这是首次证明单反式 EPA 异构体在饮食摄入后被纳入肝线粒体膜中。
