Stanislav Grabovskiy - Trans Fatty Acids: Chemical Synthesis of Eicosapentaenoic Acid Isomers and Detection in Rats Fed a Deodorized Fish Oil Diet

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  Publication Details (including relevant citation   information):

  Chem. Res. Toxicol., 2012, 25 (3), pp 687–694
  DOI: 10.1021/tx200467c


  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.

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