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Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans

Analytical and Bioanalytical Chemistry volume 408, pages 6141–6151 (2016)Cite this article

Abstract

The endocannabinoid system is important in various physiological pathways, especially the regulation of food intake. It consists of endocannabinoids like 2-arachidonoyl-glycerol (2-AG) or the fatty acid ethanolamide archachidonoyl-ethanolamide (AEA) with binding affinity to cannabinoid receptors. Further, fatty acid ethanolamides (FAEAs) influence the endocannabinoid system without affecting cannabinoid receptors by using independent physiological pathways. Among FAEAs, oleic acid ethanolamide (OEA) gained importance because of its promising ability to reduce food intake. By ultrahigh-performance liquid chromatography–electrospray ionization–tandem mass spectrometry (UHPLC–ESI–MS/MS), we detected a chromatographically separated molecule in plasma samples from rats and humans with identical mass and fragmentation patterns as those of OEA. Via synthesis and extensive analysis of ethanolamides of different cis/trans- and position isomers of oleic acid (cis9-18:1), we could identify the unknown molecule as vaccenic acid (cis11-18:1) ethanolamide (VEA). In this study we identified VEA as the most abundant 18:1 FAEA in rat plasma and the second most abundant 18:1 FAEA in human plasma.

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Acknowledgments

This study is part of the Neurotrition Project, which was supported by the FAU Emerging Fields Initiative. We thank Susanne Achenbach from the blood donor bank in Erlangen, Germany, for providing human blood samples, Andreas Hess for providing the infrastructure for blood taking of rats, Johannes Niebler for his expertise regarding GC–MS measurements, and Christine Meissner for proofreading the manuscript.

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Authors and Affiliations

  1. Food Chemistry Unit, Department of Chemistry and Pharmacy, Emil Fischer Center, Friedrich-Alexander Universität Erlangen-Nürnberg (FAU), Schuhstr. 19, 91052, Erlangen, Germany

    Waldemar Röhrig, Christopher Perlwitz, Monika Pischetsrieder & Tobias Hoch

  2. Medicinal Chemistry Unit, Department of Chemistry and Pharmacy, Emil Fischer Center, Friedrich-Alexander Universität Erlangen-Nürnberg (FAU), Schuhstr. 19, 91052, Erlangen, Germany

    Reiner Waibel

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  1. Waldemar Röhrig
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Correspondence to Tobias Hoch.

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Röhrig, W., Waibel, R., Perlwitz, C. et al. Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans. Anal Bioanal Chem 408, 6141–6151 (2016). https://doi.org/10.1007/s00216-016-9720-8

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  • DOI: https://doi.org/10.1007/s00216-016-9720-8

Keywords

  • OEA
  • VEA
  • Fatty acid ethanolamides
  • Endocannabinoid system
  • LC–MS/MS