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Ethanolamide Oxylipins of Linolenic Acid Can Negatively Regulate Arabidopsis Seedling Development

Overview
Journal Plant Cell
Specialties Biology
Cell Biology
Date 2013 Oct 24
PMID 24151297
Citations 16
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Abstract

N-Acylethanolamines (NAEs) are fatty-acid derivatives with potent biological activities in a wide range of eukaryotic organisms. Polyunsaturated NAEs are among the most abundant NAE types in seeds of Arabidopsis thaliana, and they can be metabolized by either fatty acid amide hydrolase (FAAH) or by lipoxygenase (LOX) to low levels during seedling establishment. Here, we identify and quantify endogenous oxylipin metabolites of N-linolenoylethanolamine (NAE 18:3) in Arabidopsis seedlings and show that their levels were higher in faah knockout seedlings. Quantification of oxylipin metabolites in lox mutants demonstrated altered partitioning of NAE 18:3 into 9- or 13-LOX pathways, and this was especially exaggerated when exogenous NAE was added to seedlings. When maintained at micromolar concentrations, NAE 18:3 specifically induced cotyledon bleaching of light-grown seedlings within a restricted stage of development. Comprehensive oxylipin profiling together with genetic and pharmacological interference with LOX activity suggested that both 9-hydroxy and 13-hydroxy linolenoylethanolamides, but not corresponding free fatty-acid metabolites, contributed to the reversible disruption of thylakoid membranes in chloroplasts of seedling cotyledons. We suggest that NAE oxylipins of linolenic acid represent a newly identified, endogenous set of bioactive compounds that may act in opposition to progression of normal seedling development and must be depleted for successful establishment.

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References
1.
van der Stelt M, Noordermeer M, Kiss T, van Zadelhoff G, Merghart B, Veldink G . Formation of a new class of oxylipins from N-acyl(ethanol)amines by the lipoxygenase pathway. Eur J Biochem. 2000; 267(7):2000-7. DOI: 10.1046/j.1432-1327.2000.01203.x. View

2.
Keereetaweep J, Kilaru A, Feussner I, Venables B, Chapman K . Lauroylethanolamide is a potent competitive inhibitor of lipoxygenase activity. FEBS Lett. 2010; 584(14):3215-22. DOI: 10.1016/j.febslet.2010.06.008. View

3.
Lopez-Molina L, Mongrand S, Chua N . A postgermination developmental arrest checkpoint is mediated by abscisic acid and requires the ABI5 transcription factor in Arabidopsis. Proc Natl Acad Sci U S A. 2001; 98(8):4782-7. PMC: 31911. DOI: 10.1073/pnas.081594298. View

4.
Glauser G, Dubugnon L, Mousavi S, Rudaz S, Wolfender J, Farmer E . Velocity estimates for signal propagation leading to systemic jasmonic acid accumulation in wounded Arabidopsis. J Biol Chem. 2009; 284(50):34506-13. PMC: 2787311. DOI: 10.1074/jbc.M109.061432. View

5.
Sang N, Chen C . Lipid signaling and synaptic plasticity. Neuroscientist. 2006; 12(5):425-34. DOI: 10.1177/1073858406290794. View