Fatty Acid Amide Hydrolase and the Metabolism of N-Acylethanolamine Lipid Mediators in Plants

  • Kent D. ChapmanEmail author
  • Elison B. Blancaflor
Part of the Plant Cell Monographs book series (CELLMONO, volume 16)


N-Acylethanolamines (NAEs) are a group of fatty acid derivatives that have been identified in a wide range of multicellular eukaryotes, some unicellular eukaryotes, and in a limited number of prokaryotes. The precise acyl composition of the NAE pool in organisms is variable and the overall levels of NAEs fluctuate with changes in development or in response to cellular stresses, especially where it has been studied in animal and plant systems. In animals, these lipids belong to the endocannabinoid pathway where they regulate diverse behavioral and physiological processes. In plant systems, these NAEs have potent growth-regulating activities, which are terminated by their hydrolysis. The inactivation of NAEs, in part, is accomplished by an enzyme identified as a functional homolog of the fatty acid amide hydrolase (FAAH) that regulates endocannabinoid metabolism in vertebrates. Here, the molecular and biochemical characteristics of this enzyme and its role in NAE metabolism in plants are reviewed.


Fatty Acid Amide Hydrolase Fatty Acid Derivative At5g07360 Gene Fatty Acid Amide Hydrolase Activity Fatty Acid Amide Hydrolase Enzyme 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



Work in the authors’ laboratories on N-acylethanolamine metabolism has been supported by grants from the USDA-NRI competitive grants program and the U.S. Department of Energy, Energy Biosciences Program. We thank Dr. Charlene Case-Richardson for assistance with manuscript preparation.


  1. Blancaflor EB, Chapman KD (2006) Similarities between endocannabinoid signaling in animal systems and N-acylethanolamine metabolism in plants. In: Communication in plants: neuronal aspects of plant life. Springer, Berlin, pp 205–219Google Scholar
  2. Blancaflor EB, Hou G, Chapman KD (2003) Elevated levels of N-lauroylethanolamine, an endogenous constituent of desiccated seeds, disrupt normal root development in Arabidopsis thaliana seedlings. Planta 217:206–217PubMedGoogle Scholar
  3. Bracey MH, Hanson MA, Masuda KR, Stevens RC, Cravatt BF (2002) Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling. Science 298:1793–1796CrossRefPubMedGoogle Scholar
  4. Campos-Cuevas JC, Pelagio-Flores R, Raya-González J, Méndez-Bravo A, Ortiz-Castro R, López-Bucio J (2008) Tissue culture of Arabidopsis thaliana explants reveals a stimulatory effect of alkamides on adventitious root formation and nitric oxide accumulation. Plant Sci 174:165CrossRefGoogle Scholar
  5. Chapman KD (2004) Occurrence, metabolism, and prospective functions of N-acylethanolamines in plants. Prog Lipid Res 43:302–327CrossRefPubMedGoogle Scholar
  6. Chapman KD, Venables B, Markovic R, Blair RW Jr, Bettinger C (1999) N-Acylethanolamines in seeds. Quantification of molecular species and their degradation upon imbibition. Plant Physiol 120:1157–1164CrossRefPubMedGoogle Scholar
  7. Cravatt BF, Lichtman AH (2003) Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system. Curr Opin Chem Biol 7:469–475CrossRefPubMedGoogle Scholar
  8. Cravatt BF, Giang DK, Mayfield SP, Boger DL, Lerner RA, Gilula NB (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 384:83–87CrossRefPubMedGoogle Scholar
  9. Dunkley TP, Hester S, Shadforth IP, Runions J, Weimar T, Hanton SL, Griffin JL, Bessant C, Brandizzi F, Hawes C, Watson RB, Dupree P, Lilley KS (2006) Mapping the Arabidopsis organelle proteome. Proc Natl Acad Sci U S A 103:6518–6523CrossRefPubMedGoogle Scholar
  10. Han L, Gao JR, Li ZM, Zhang Y, Guo WM (2007) Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine. Bioorg Med Chem Lett 17:3231–3234CrossRefPubMedGoogle Scholar
  11. Kang L, Wang Y-S, Uppalapati SR, Wang K, Tang Y, Vadapalli V, Venables BJ, Chapman KD, Blancaflor EB, Mysore KS (2008) Overexpression of a fatty acid amide hydrolase compromises innate immunity in Arabidopsis. Plant J 56:336–349CrossRefPubMedGoogle Scholar
  12. Kathuria S, Gaetani S, Fegley D, Valino F, Duranti A, Tontini A, Mor M, Tarzia G, La Rana G, Calignano A, Giustino A, Tattoli M, Palmery M, Cuomo V, Piomelli D (2003) Modulation of anxiety through blockade of anandamide hydrolysis. Nat Med 9:76–81CrossRefPubMedGoogle Scholar
  13. Kilaru A, Blancaflor EB, Venables B, Tripathy S, Mysore K, Chapman KD (2007) The N-Acylethanolamine-mediated regulatory pathway in plants. Chem Biodivers 4(8):1933–1955Google Scholar
  14. Kurahashi Y, Ueda N, Suzuki H, Suzuki M, Yamamoto S (1997) Reversible hydrolysis and synthesis of anandamide demonstrated by recombinant rat fatty-acid amide hydrolase. Biochem Biophys Res Commun 237:512–515CrossRefPubMedGoogle Scholar
  15. Labar G, Michaux C (2007) Fatty acid amide hydrolase: from characterization to therapeutics. Chem Biodivers 4:1882–1902CrossRefPubMedGoogle Scholar
  16. Lopez-Bucio J, Acevedo-Hernandez G, Ramirez-Chavez E, Molina-Torres J, Herrera-Estrella L (2006) Novel signals for plant development. Curr Opin Plant Biol 9:523–529CrossRefPubMedGoogle Scholar
  17. Lopez-Bucio J, Millan-Godinez M, Mendez-Bravo A, Morquecho-Contreras A, Ramirez-Chavez E, Molina-Torres J, Perez-Torres A, Higuchi M, Kakimoto T, Herrera-Estrella L (2007) Cytokinin receptors are involved in alkamide regulation of root and shoot development in Arabidopsis. Plant Physiol 145:1703–1713CrossRefPubMedGoogle Scholar
  18. Lopez-Molina L, Mongrand S, Chua NH (2001) 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 98:4782–4787CrossRefPubMedGoogle Scholar
  19. Lopez-Molina L, Mongrand S, McLachlin DT, Chait BT, Chua N-H (2002) ABI5 acts downstream of ABI3 to execute an ABA-dependent growth arrest during germination. Plant J 32:317–328CrossRefPubMedGoogle Scholar
  20. McKinney MK, Cravatt BF (2005) Structure and function of fatty acid amide hydrolase. Annu Rev Biochem 74:411–432CrossRefPubMedGoogle Scholar
  21. Merkel O, Schmid PC, Paltauf F, Schmid HH (2005) Presence and potential signaling function of N-acylethanolamines and their phospholipid precursors in the yeast Saccharomyces cerevisiae. Biochim Biophys Acta 1734:215–219PubMedGoogle Scholar
  22. Motes CM, Pechter P, Yoo CM, Wang YS, Chapman KD, Blancaflor EB (2005) Differential effects of two phospholipase D inhibitors, 1-butanol and N-acylethanolamine, on in vivo cytoskeletal organization and Arabidopsis seedling growth. Protoplasma 226:109–123CrossRefPubMedGoogle Scholar
  23. Neu D, Lehmann T, Elleuche S, Pollmann S (2007) Arabidopsis amidase 1, a member of the amidase signature family. FEBS J 274:3440–3451CrossRefPubMedGoogle Scholar
  24. Nishimura N, Yoshida T, Kitahata N, Asami T, Shinozaki K, Hirayama T (2007) ABA-Hypersensitive Germination1 encodes a protein phosphatase 2C, an essential component of abscisic acid signaling in Arabidopsis seed. Plant J 50:935–949CrossRefPubMedGoogle Scholar
  25. Oddi S, Bari M, Battista N, Barsacchi D, Cozzani I, Maccarrone M (2005) Confocal microscopy and biochemical analysis reveal spatial and functional separation between anandamide uptake and hydrolysis in human keratinocytes. Cell Mol Life Sci 62:386–395CrossRefPubMedGoogle Scholar
  26. O'Malley RC, Alonso JM, Kim CJ, Leisse TJ, Ecker JR (2007) An adapter ligation-mediated PCR method for high-throughput mapping of T-DNA inserts in the Arabidopsis genome. Nat Protoc 2:2910–2917CrossRefPubMedGoogle Scholar
  27. Pollmann S, Neu D, Lehmann T, Berkowitz O, Schafer T, Weiler EW (2006) Subcellular localization and tissue specific expression of amidase 1 from Arabidopsis thaliana. Planta 224:1241–1253CrossRefPubMedGoogle Scholar
  28. Schmid HH, Schmid PC, Natarajan V (1996) The N-acylation-phosphodiesterase pathway and cell signalling. Chem Phys Lipids 80:133–142CrossRefPubMedGoogle Scholar
  29. Shrestha R, Noordermeer MA, van der Stelt M, Veldink GA, Chapman KD (2002) N-acylethanolamines are metabolized by lipoxygenase and amidohydrolase in competing pathways during cottonseed imbibition. Plant Physiol 130:391–401CrossRefPubMedGoogle Scholar
  30. Shrestha R, Dixon RA, Chapman KD (2003) Molecular identification of a functional homologue of the mammalian fatty acid amide hydrolase in Arabidopsis thaliana. J Biol Chem 278:34990–34997CrossRefPubMedGoogle Scholar
  31. Shrestha R, Kim SC, Dyer JM, Dixon RA, Chapman KD (2006) Plant fatty acid (ethanol) amide hydrolases. Biochim Biophys Acta 1761:324–334PubMedGoogle Scholar
  32. Sun YX, Tsuboi K, Zhao LY, Okamoto Y, Lambert DM, Ueda N (2005) Involvement of N-acylethanolamine-hydrolyzing acid amidase in the degradation of anandamide and other N-acylethanolamines in macrophages. Biochim Biophys Acta 1736:211–220PubMedGoogle Scholar
  33. Teaster ND, Motes CM, Tang Y, Wiant WC, Cotter MQ, Wang YS, Kilaru A, Venables BJ, Hasenstein KH, Gonzalez G, Blancaflor EB, Chapman KD (2007) N-Acylethanolamine metabolism interacts with abscisic acid signaling in Arabidopsis thaliana seedlings. Plant Cell 19:2454–2469CrossRefPubMedGoogle Scholar
  34. Tsuboi K, Sun YX, Okamoto Y, Araki N, Tonai T, Ueda N (2005) Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase. J Biol Chem 280:11082–11092CrossRefPubMedGoogle Scholar
  35. Tsuboi K, Zhao LY, Okamoto Y, Araki N, Ueno M, Sakamoto H, Ueda N (2007) Predominant expression of lysosomal N-acylethanolamine-hydrolyzing acid amidase in macrophages revealed by immunochemical studies. Biochim Biophys Acta 1771:623–632PubMedGoogle Scholar
  36. Venables BJ, Waggoner CA, Chapman KD (2005) N-acylethanolamines in seeds of selected legumes. Phytochemistry 66:1913–1918CrossRefPubMedGoogle Scholar
  37. Wang YS, Shrestha R, Kilaru A, Wiant W, Venables BJ, Chapman KD, Blancaflor EB (2006) Manipulation of Arabidopsis fatty acid amide hydrolase expression modifies plant growth and sensitivity to N-acylethanolamines. Proc Natl Acad Sci U S A 103:12197–12202CrossRefPubMedGoogle Scholar
  38. Wei BQ, Mikkelsen TS, McKinney MK, Lander ES, Cravatt BF (2006) A second fatty acid amide hydrolase with variable distribution among placental mammals. J Biol Chem 281:36569–36578CrossRefPubMedGoogle Scholar
  39. Wilson RI, Nicoll RA (2002) Endocannabinoid signaling in the brain. Science 296:678–682CrossRefPubMedGoogle Scholar
  40. Zhang Y, Guo WM, Chen SM, Han L, Li ZM (2007) The role of N-lauroylethanolamine in the regulation of senescence of cut carnations (Dianthus caryophyllus). J Plant Physiol 164:993–1001CrossRefPubMedGoogle Scholar
  41. Zimmermann P, Hirsch-Hoffmann M, Hennig L, Gruissem W (2004) GENEVESTIGATOR. Arabidopsis microarray database and analysis toolbox. Plant Physiol 136:2621–2632CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of Biological SciencesUniversity of North Texas, Center for Plant Lipid ResearchDentonUSA

Personalised recommendations