<i>N</i>-Acylethanolamines in Signal Transduction of Elicitor Perception. Attenuation of Alkalinization Response and Activation of Defense Gene Expression

Tripathy, Swati; Venables, Barney J.; Chapman, Kent D.

doi:10.1104/pp.121.4.1299

Cited by 63 publications

(76 citation statements)

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“…As a consequence, we proposed that activation of PLD␤ or ␥, but not ␣, was responsible for the metabolic release of NAEs from tobacco cell suspensions. These NAEs were identified structurally as NAE 12:0 and NAE 14:0, and NAE formation was subsequently shown to occur in leaves of intact tobacco plants (Tripathy et al, 1999). Inhibition of PLD␣ by endogenous metabolites of PLD␤ (or ␥) may Figure 5.…”

Section: Discussionmentioning

confidence: 99%

“…The unregulated activity of PLD␣ in plant cells, then, potentially would lead to membrane damage and loss of cellular function, and cells likely have mechanisms in place to regulate PLD␣ activity. In addition, a signal transduction role for the PLD␣ isoform has been implicated from studies in several plant systems in which PLD␣ mediates, in part, the cellular responses to abscisic acid (ABA; Fan et al, 1997;Ritchie and Gilroy, 1998;Jacob et al, 1999;Frank et al, 2000;Sang et al, 2001).Recent evidence in tobacco (Nicotiana tabacum) cells indicated that a novel class of lipids, N-acylethanolamines (NAEs), was released from the membrane phospholipid, N-acylphosphatidylethanolamine (NAPE), in a signal-mediated fashion Tripathy et al, 1999). A PLD-type activity was identified that hydrolyzed NAPE to NAE in vitro , and a subsequent biochemical survey of PLD catalytic properties of recombinant isoforms (Pappan et al, 1998) suggested that the activity in tobacco microsomes likely was attributed to the ␤ or ␥ isoforms.…”

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“…Recent evidence in tobacco (Nicotiana tabacum) cells indicated that a novel class of lipids, N-acylethanolamines (NAEs), was released from the membrane phospholipid, N-acylphosphatidylethanolamine (NAPE), in a signal-mediated fashion Tripathy et al, 1999). A PLD-type activity was identified that hydrolyzed NAPE to NAE in vitro , and a subsequent biochemical survey of PLD catalytic properties of recombinant isoforms (Pappan et al, 1998) suggested that the activity in tobacco microsomes likely was attributed to the ␤ or ␥ isoforms.…”

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Inhibition of Phospholipase Dα byN-Acylethanolamines

Austin-Brown

Chapman

2002

Plant Physiology

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N-Acylethanolamines (NAEs) are endogenous lipids in plants produced from the phospholipid precursor, N-acylphosphatidylethanolamine, by phospholipase D (PLD). Here, we show that seven types of plant NAEs differing in acyl chain length and degree of unsaturation were potent inhibitors of the well-characterized, plant-specific isoform of PLD-PLD␣. It is notable that PLD␣, unlike other PLD isoforms, has been shown not to catalyze the formation of NAEs from N-acylphosphatidylethanolamine. In general, inhibition of PLD␣ activity by NAEs increased with decreasing acyl chain length and decreasing degree of unsaturation, such that N-lauroylethanolamine and N-myristoylethanolamine were most potent with IC 50 s at submicromolar concentrations for the recombinant castor bean (Ricinus communis) PLD␣ expressed in Escherichia coli and for partially purified cabbage (Brassica oleracea) PLD␣. NAEs did not inhibit PLD from Streptomyces chromofuscus, and exhibited only moderate, mixed effects for two other recombinant plant PLD isoforms. Consistent with the inhibitory biochemical effects on PLD␣ in vitro, N-lauroylethanolamine, but not lauric acid, selectively inhibited abscisic acid-induced closure of stomata in epidermal peels of tobacco (Nicotiana tabacum cv Xanthi) and Commelina communis at low micromolar concentrations. Together, these results provide a new class of biochemical inhibitors to assist in the evaluation of PLD␣ physiological function(s), and they suggest a novel, lipid mediator role for endogenously produced NAEs in plant cells.Hydrolysis of membrane phospholipids by phospholipase D 2 (PLD, EC 3.1.4.4) activity in plants has been known for decades (Hanahan and Chaikoff, 1947); however, its precise physiological roles in plants are only beginning to be understood (for review, see Chapman et al., 1998;Munnik et al., 1998;Wang, 2001b). Recent evidence at the molecular level indicates that there are at least four functional isoforms of PLD in higher plants, designated ␣, ␤, ␥, and ␦, and their biochemical properties differ substantially (Wang, 2001a). PLD␣ catalyzes the wellcharacterized transphosphatidylation activity, which requires millimolar concentrations of Ca 2ϩ for optimal activity. At least two isoforms (␤ and ␥) appear to be optimally activated by micromolar concentrations of Ca 2ϩ and binding of inositol-containing phospholipids (Pappan et al., 1997), and these exhibit phospholipid substrate selectivity that differ markedly from that of PLD␣ (Pappan et al., 1998). The recently described PLD␦ activity is membrane associated and activated by free oleic acid .Evidence for the physiological function of PLD␣ points to a role in the degradation/reorganization of subcellular membranes, as well as a role in signal transduction (for review, see Chapman et al., 1998). This membrane degradation is manifested at the cellular level by loss of compartmentation leading to cell death, such as in phytohormone-initiated, PLDmediated senescence (Thompson, 1988;Fan et al., 1997). The unregulated activity of PLD␣ in plant cel...

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Inhibition of Phospholipase Dα byN-Acylethanolamines

Austin-Brown

Chapman

2002

Plant Physiology

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“…For example, a phospholipase D-mediated accumulation of extracellular NAE 14:0 was triggered in tobacco (Nicotiana tabacum) cell suspensions (Chapman et al, 1998) and leaves (Tripathy et al, 1999) within minutes after elicitor perception. Nanomolar concentrations of NAE 14:0 activated Phe ammonia-lyase (PAL) gene expression in both cell suspensions and leaves of intact plants in a manner similar to, but independent of, pathogen elicitor treatment.…”

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“…NAEs are released from NAPE by phospholipase d-type hydrolases in response to a variety of stimuli (Di Marzo et al, 1994;Schmid et al, 1996;Chapman et al, 1998;Hansen et al, 1998). During the past decade, transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission (Schmid et al, 1996;Di Marzo, 1998a, 1998b, membrane protection (Hansen et al, 2000), immunomodulation in animals (Klein et al, 1998), and defense signaling in plants (Tripathy et al, 1999;Chapman, 2000).…”

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N-Acylethanolamine Signaling in Tobacco Is Mediated by a Membrane-Associated, High-Affinity Binding Protein

et al. 2003

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N-Acylethanolamines (NAEs) are fatty acid derivatives found as minor constituents of animal and plant tissues, and their levels increase 10- to 50-fold in tobacco (Nicotiana tabacum) leaves treated with fungal elicitors. Infiltration of tobacco leaves with submicromolar to micromolar concentrations ofN-myristoylethanolamine (NAE 14:0) resulted in an increase in relative phenylalanine ammonia-lyase (PAL) transcript abundance within 8 h after infiltration, and this PAL activation was reduced after co-infiltration with cannabinoid receptor antagonists (AM 281 and SR 144528). A saturable, high-affinity specific binding activity for [3H]NAE 14:0 was identified in suspension-cultured tobacco cells and in microsomes from tobacco leaves (apparent K d of 74 and 35 nm,respectively); cannabinoid receptor antagonists reduced or eliminated specific [3H]NAE 14:0 binding, consistent with the physiological response. N-Oleoylethanolamine activatedPAL2 expression in leaves and diminished [3H]NAE 14:0 binding in microsomes, whereasN-linoleoylethanolamine did not activatePAL2 expression in leaves, and did not affect [3H]NAE 14:0 binding in microsomes. The nonionic detergent dodecylmaltoside solubilized functional [3H]NAE 14:0-binding activity from tobacco microsomal membranes. The dodecylmaltoside-solubilized NAE-binding activity retained similar, but not identical, binding properties to the NAE-binding protein(s) in intact tobacco microsomes. Additionally, high-affinity saturable NAE-binding proteins were identified in microsomes isolated from Arabidopsis and Medicago truncatula tissues, indicating the general prevalence of these binding proteins in plant membranes. We propose that plants possess an NAE-signaling pathway with functional similarities to the “endocannabinoid” pathway of animal systems and that this pathway, in part, participates in xylanase elicitor perception in tobacco.

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Endocannabinoid‐Like Lipids in Plants

Chilufya

Devaiah

Sante

et al. 2015

Encyclopedia of Life Sciences

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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.

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N-Acylethanolamines in Signal Transduction of Elicitor Perception. Attenuation of Alkalinization Response and Activation of Defense Gene Expression

Cited by 63 publications

References 79 publications

Inhibition of Phospholipase Dα byN-Acylethanolamines

Inhibition of Phospholipase Dα byN-Acylethanolamines

N-Acylethanolamine Signaling in Tobacco Is Mediated by a Membrane-Associated, High-Affinity Binding Protein

Endocannabinoid‐Like Lipids in Plants

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