Impact of embedded endocannabinoids and their oxygenation by lipoxygenase on membrane properties

Enrico Dainese, Annalaura Sabatucci, Clotilde B. Angelucci, Daniela Barsacchi, Marco Chiarini, Mauro MacCarrone

Research output: Contribution to journalArticlepeer-review


N-Arachidonoylethanolamine (anandamide) and 2-arachidonoylglycerol are the best characterized endocannabinoids. Their biological activity is subjected to metabolic control whereby a dynamic equilibrium among biosynthetic, catabolic, and oxidative pathways drives their intracellular concentrations. In particular, lipoxygenases can generate hydroperoxy derivatives of endocannabinoids, endowed with distinct activities within cells. The in vivo interaction between lipoxygenases and endocannabinoids is likely to occur within cell membranes; thus, we sought to ascertain whether a prototypical enzyme like soybean (Glycine max) 15-lipoxygenase-1 is able to oxygenate endocannabinoids embedded in synthetic vesicles and how these substances could affect the binding ability of the enzyme to different lipid bilayers. We show that (i) embedded endocannabinoids increase membrane fluidity; (ii) 15-lipoxygenase-1 preferentially binds to endocannabinoid-containing bilayers; and that (iii) 15-lipoxygenase-1 oxidizes embedded endocannabinoids and thus reduces fluidity and local hydration of membrane lipids. Together, the present findings reveal further complexity in the regulation of endocannabinoid signaling within the central nervous system, disclosing novel control by oxidative pathways.

Original languageEnglish
Pages (from-to)386-392
Number of pages7
JournalACS Chemical Neuroscience
Issue number5
Publication statusPublished - May 16 2012


  • Endocannabinoids
  • FRET
  • FTIR
  • laurdan fluorescence
  • lipoxygenase activity
  • membrane binding

ASJC Scopus subject areas

  • Biochemistry
  • Cell Biology
  • Physiology
  • Cognitive Neuroscience


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