Endocannabinoid‐Like Lipids in Plants

Abstract

Classically, endogenous fatty acid ethanolamides and their derivatives that bind to the cannabinoid receptors and trigger a signalling pathway are referred to as endocannabinoids. Although derivatives of arachidonic acid, including arachidonylethanolamine or anandamide, are the known endogenous ligands for cannabinoid receptors, other fatty acid ethanolamides or N‐acylethanolamines (NAE) that vary in carbon chain length and saturation occur ubiquitously in eukaryotic organisms and play an important role in their physiology and development. The metabolic pathway for NAEs is highly conserved among eukaryotes and well characterised in mammalian systems. Although NAE pathway is only partly elucidated in plants, significant progress has been made in the past 20 years in understanding the implications of the metabolism of saturated and unsaturated endocannabinoid‐like molecules in plant development and growth. The latest advancements in the field of plant endocannabinoid research are reviewed.

Key Concepts

  • Endocannabinoids are endogenous ligands of cannabinoid receptors in mammalian systems.
  • Endocannabinoids belong to a class of small bioactive lipid molecules that are derivatives of fatty acids including their ethanolamides, referred to as N‐acylethanolamines.
  • N‐Acylethanolamines are ubiquitous and their metabolic pathway is highly conserved among eukaryotes.
  • In higher plants, only 12–18C N‐acylethanolamines have been identified and their metabolic pathway is partly elucidated.
  • The endocannabinoid‐like lipids play an important role in seed germination, seedling development, flowering and cellular organisation.
  • In plants, N‐acylethanolamines also participate in mediating responses to biotic and abiotic stress.

Keywords: anandamide; cannabinoid receptor; endocannabinoid; fatty acid amide hydrolase; fatty acid ethanolamide; plant lipid signalling; lipoxygenase; N‐acylethanolamine; N‐acylphosphatidylethanolamine; oxylipins

Figure 1. Structure of cannabinoids derived from Cannabis. (a) Delta‐9‐tetrahydrocannabinol, (b) cannabidiol and (c) cannabinol.
Figure 2. Arachidonylethanolamide or anandamide (NAE 20:4) is the first endogenous cannabinoid ligand that was discovered in mammals.
Figure 3. Structure of arachidonate‐derived endocannabinoids. (a) Arachidonic acid, precursor but not an endocannabinoid ligand, (b) 2‐arachidonylglycerol, (c) 2‐arachidonylglyceryl ether, (d) O‐arachidonyl ethanolamine and (e) N‐arachidonyl dopamine are endogenous ligands of cannabinoid receptors.
Figure 4. Fatty acid ethanolamides or N‐acylethanolamines that vary in acyl chain length and degree of saturation are bioactive lipid molecules that do not interact with cannabinoid receptors but play an important physiological role in eukaryotes.
Figure 5. Schematic diagram of N‐acylethanolamine (NAE) metabolic pathway. NAEs are formed by the hydrolysis of N‐acylphosphatidylethanolamine (NAPE) by a phospholipase‐D (NAPE‐PLD) and are hydrolysed by fatty acid amide hydrolase (FAAH) into ethanolamine (EA) and free fatty acid (FFA). Polyunsaturated NAEs can also be oxidised to NAE‐oxylipins via lipoxygenases (LOX). NAPE in plants is formed from phosphatidylethanolamine (PE) and FFA or acyl‐CoA by the activity of an NAPE synthase.
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Chilufya, Jedaidah Y, Devaiah, Shivakumar P, Sante, Richard R, and Kilaru, Aruna(Oct 2015) Endocannabinoid‐Like Lipids in Plants. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1002/9780470015902.a0024632]