Dihydroxylated E,E,Z-docosatrienes. An overview of their synthesis and biological significance

Prog Lipid Res. 2016 Jan:61:1-18. doi: 10.1016/j.plipres.2015.10.002. Epub 2015 Nov 9.


Dihydroxylated E,E,Z-docosatrienes are acyclic lipoxygenase metabolites of 22-carbon atom polyunsaturated fatty acids (PUFAs) containing a conjugated E,E,Z-triene flanked by two secondary allylic alcohols. The two main metabolites, protectin D1 (PD1) and its regioisomer maresin 1 (MaR1), were shown to be actively involved in the resolution and more specifically the termination of the inflammation process. Studies directed at the synthesis of E,E,Z-docosatrienes have been undertaken to resolve stereochemical ambiguities, and provide standards for biological evaluation and reference samples for in-vivo detection and lipidomic analyses. In this review we provide a brief update of the literature on the biological significance of E,E,Z-docosatrienes and the role that synthetic organic chemists has played in the development of these lipids, providing an overview and comparison of the different strategies employed to access synthetic E,E,Z-docosatriene standards.

Keywords: Docosatriene; Inflammation; Maresin; PUFA metabolite; Protectin; Virology.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Animals
  • Biosynthetic Pathways
  • Chemistry Techniques, Synthetic
  • Docosahexaenoic Acids / chemical synthesis
  • Docosahexaenoic Acids / pharmacology
  • Docosahexaenoic Acids / physiology*
  • Humans
  • Hydroxylation
  • Lipid Metabolism
  • Nerve Regeneration
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / pharmacology


  • Neuroprotective Agents
  • Docosahexaenoic Acids