Fatty acid amide lipid mediators in plants

Plant Science

Volumn 178, Issue 5, 2010, Pages 411-419

  Kim, Sang Chul ^a   Chapman, Kent D ^a   Blancaflor, Elison B ^a,b  

^a UNIVERSITY OF NORTH TEXAS   (United States)

^b PLANT BIOLOGY DIVISION   (United States)

Author keywords

Endocannabinoid signaling; Fatty acid amide hydrolase; N Acylethanolamines; Plant development; Plant lipids

Indexed keywords

ANIMALIA; FUNGI; MAMMALIA;

EID: 77950323423     PISSN: 01689452     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.plantsci.2010.02.017     Document Type: Review

References (84)

1. Di Marzo V., Bisogno T., and De Petrocellis L. Endocannabinoids and related compounds: walking back and forth between plant natural products and animal physiology. Chem. Biol. 14 (2007) 741-756
2. Devane W.A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 (1992) 1946-1949
3. Mouslech Z., and Valla V. Endocannabinoid system: an overview of its potential in current medical practice. Neuro Endocrinol. Lett. 30 (2009) 153-179
4. Di Marzo V. The endocannabinoid system: its general strategy of action, tools for its pharmacological manipulation and potential therapeutic exploitation. Pharmacol. Res. 60 (2009) 77-84
5. Wang J., and Ueda N. Biology of endocannabinoid synthesis system. Prostaglandins Other Lipid Mediat. 89 (2009) 112-119
6. Goodfellow C.E., and Glass M. Anandamide receptor signal transduction. Vitam. Horm. 81 (2009) 79-110
7. Hanus L., et al. 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 3662-3665
8. Bisogno T., et al. N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem. J. 351 Pt. 3 (2000) 817-824
9. Porter A.C., et al. Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J. Pharmacol. Exp. Ther. 301 (2002) 1020-1024
10. Kano M., Ohno-Shosaku T., Hashimotodani Y., Uchigashima M., and Watanabe M. Endocannabinoid-mediated control of synaptic transmission. Physiol. Rev. 89 (2009) 309-380
11. Wade M.R., Tzavara E.T., and Nomikos G.G. Cannabinoids reduce cAMP levels in the striatum of freely moving rats: an in vivo microdialysis study. Brain Res. 1005 (2004) 117-123
12. Busch L., Sterin-Borda L., and Borda E. Expression and biological effects of CB1 cannabinoid receptor in rat parotid gland. Biochem. Pharmacol. 68 (2004) 1767-1774
13. Derkinderen P., et al. Regulation of extracellular signal-regulated kinase by cannabinoids in hippocampus. J. Neurosci. 23 (2003) 2371-2382
14. Galve-Roperh I., Rueda D., Gomez del Pulgar T., Velasco G., and Guzman M. Mechanism of extracellular signal-regulated kinase activation by the CB(1) cannabinoid receptor. Mol. Pharmacol. 62 (2002) 1385-1392
15. Demuth D.G., and Molleman A. Cannabinoid signalling. Life Sci. 78 (2006) 549-563
16. Chapman K.D. Occurrence, metabolism, and prospective functions of N-acylethanolamines in plants. Prog. Lipid Res. 43 (2004) 302-327
17. Kilaru A., Blancaflor E.B., Venables B.J., Tripathy S., Mysore K.S., and Chapman K.D. The N-acylethanolamine-mediated regulatory pathway in plants. Chem. Biodivers. 4 (2007) 1933-1955
18. Merkel O., Schmid P.C., Paltauf F., and Schmid H.H. Presence and potential signaling function of N-acylethanolamines and their phospholipid precursors in the yeast Saccharomyces cerevisiae. Biochim. Biophys. Acta 1734 (2005) 215-219
19. Chapman K.D., Venables B., Markovic R., Blair Jr. R.W., and Bettinger C. N-acylethanolamines in seeds. Quantification of molecular species and their degradation upon imbibition. Plant Physiol. 120 (1999) 1157-1164
20. Chapman K.D., Venables B.J., Dian E.E., and Grossa G.W. Identification and quantification of neuroactive N-acylethanolamines in cottonseed processing fractions. J. Am. Oil Chem. Soc. 80 (2003) 223-229
21. Venables B.J., Waggoner C.A., and Chapman K.D. N-acylethanolamines in seeds of selected legumes. Phytochemistry 66 (2005) 1913-1918
22. Chapman K.D., Tripathy S., Venables B., and Desouza A.D. N-Acylethanolamines: formation and molecular composition of a new class of plant lipids. Plant Physiol. 116 (1998) 1163-1168
23. Tripathy S., Venables B.J., and Chapman K.D. N-acylethanolamines in signal transduction of elicitor perception. Attenuation of alkalinization response and activation of defense gene expression. Plant Physiol. 121 (1999) 1299-1308
24. Dixon R.A., Achnine L., Kota P., Liu C.J., Reddy M.S., and Wang L. The phenylpropanoid pathway and plant defense-a genomics perspective. Plant Mol. Pathol. 3 (2002) 371-390
25. Kang L., et al. Overexpression of a fatty acid amide hydrolase compromises innate immunity in Arabidopsis. Plant J. 56 (2008) 336-349
26. Kirik A., and Mudgett M.B. SOBER1 phospholipase activity suppresses phosphatidic acid accumulation and plant immunity in response to bacterial effector AvrBsT. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 20532-20537
27. Felix G., Regenass M., and Boller T. Specific perception of subnanomolar concentrations of chitin fragments by tomato cells: induction of extracellular alkalinization, changes in protein phosphorylation, and establishment of refractory state. Plant J. 4 (1993) 307-316
28. Raffaele S., et al. A MYB transcription factor regulates very-long-chain fatty acid biosynthesis for activation of the hypersensitive cell death response in Arabidopsis. Plant Cell 20 (2008) 752-767
29. Shi L., et al. Involvement of sphingoid bases in mediating reactive oxygen intermediate production and programmed cell death in Arabidopsis. Cell Res. 17 (2007) 1030-1040
30. Austin-Brown S.L., and Chapman K.D. Inhibition of phospholipase D alpha by N-acylethanolamines. Plant Physiol. 129 (2002) 1892-1898
31. 2+, cAMP, and transduction of non-self perception during plant immune responses. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 20995-21000
32. Kim S.C., Kang L., Nagaraj S., Blancaflor E.B., Mysore K.S., and Chapman K.D. Mutations in Arabidopsis fatty acid amide hydrolase reveal that catalytic activity influences growth but not sensitivity to abscisic acid or pathogens. J. Biol. Chem. 284 (2009) 34065-34074
33. Buttner D., and Bonas U. Regulation and secretion of Xanthomonas virulence factors. FEMS Microbiol. Rev. (2009)
34. Blancaflor E.B., Hou G., and Chapman K.D. Elevated levels of N-lauroylethanolamine, an endogenous constituent of desiccated seeds, disrupt normal root development in Arabidopsis thaliana seedlings. Planta 217 (2003) 206-217
35. Ortiz-Castro R., Martinez-Trujillo M., and Lopez-Bucio J. N-acyl-l-homoserine lactones: a class of bacterial quorum-sensing signals alter post-embryonic root development in Arabidopsis thaliana. Plant Cell Environ. 31 (2008) 1497-1509
36. Motes C.M., Pechter P., Yoo C.M., Wang Y.S., Chapman K.D., and Blancaflor E.B. Differential effects of two phospholipase D inhibitors, 1-butanol and N-acylethanolamine, on in vivo cytoskeletal organization and Arabidopsis seedling growth. Protoplasma 226 (2005) 109-123
37. Gardiner J., Andreeva Z., Barton D., Ritchie A., Overall R., and Marc J. The phospholipase A inhibitor, aristolochic acid, disrupts cortical microtubule arrays and root growth in Arabidopsis. Plant Biol. (Stuttg.) 10 (2008) 725-731
38. Langhans M., and Robinson D.G. 1-Butanol targets the Golgi apparatus in tobacco BY-2 cells, but in a different way to Brefeldin A. J. Exp. Bot. 58 (2007) 3439-3447
39. Olinevich O.V., and Khokhlova L.P. Effects of abscisic acid, low temperature, and plant age on cytoskeleton and phosphorylated proteins. Biochemistry (Mosc.) 68 (2003) 678-687
40. Teaster N.D., et al. N-acylethanolamine metabolism interacts with abscisic acid signaling in Arabidopsis thaliana seedlings. Plant Cell 19 (2007) 2454-2469
41. Zhang W., Qin C., Zhao J., and Wang X. Phospholipase D alpha 1-derived phosphatidic acid interacts with ABI1 phosphatase 2C and regulates abscisic acid signaling. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 9508-9513
42. Katagiri T., Ishiyama K., Kato T., Tabata S., Kobayashi M., and Shinozaki K. An important role of phosphatidic acid in ABA signaling during germination in Arabidopsis thaliana. Plant J. 43 (2005) 107-117
43. Lopez-Bucio J., et al. Cytokinin receptors are involved in alkamide regulation of root and shoot development in Arabidopsis. Plant Physiol. 145 (2007) 1703-1713
44. Morquecho-Contreras A., et al. Characterization of drr1, an alkamide resistant mutant of Arabidopsis reveals an important role for small lipid amides in lateral root development and plant senescence. Plant Physiol. 152 (2010) 1659-1673
45. Tripathy S., Kleppinger-Sparace K., Dixon R.A., and Chapman K.D. N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 131 (2003) 1781-1791
46. Chicca A., et al. Synergistic immunomopharmacological effects of N-alkylamides in Echinacea purpurea herbal extracts. Int. Immunopharmacol. 9 (2009) 850-858
47. Raduner S., et al. Alkylamides from Echinacea are a new class of cannabinomimetics. Cannabinoid type 2 receptor-dependent and -independent immunomodulatory effects. J. Biol. Chem. 281 (2006) 14192-14206
48. Gertsch J., Schoop R., Kuenzle U., and Suter A. Echinacea alkylamides modulate TNF-alpha gene expression via cannabinoid receptor CB2 and multiple signal transduction pathways. FEBS Lett. 577 (2004) 563-569
49. Forde B.G., and Walch-Liu P. Nitrate and glutamate as environmental cues for behavioural responses in plant roots. Plant Cell Environ. 32 (2009) 682-693
50. Cravatt B.F., et al. Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 9371-9376
51. Shrestha R., Kim S.C., Dyer J.M., Dixon R.A., and Chapman K.D. Plant fatty acid (ethanol) amide hydrolases. Biochim. Biophys. Acta 1761 (2006) 324-334
52. Shrestha R., Dixon R.A., and Chapman K.D. Molecular identification of a functional homologue of the mammalian fatty acid amide hydrolase in Arabidopsis thaliana. J. Biol. Chem. 278 (2003) 34990-34997
53. Wang Y.S., et al. Manipulation of Arabidopsis fatty acid amide hydrolase expression modifies plant growth and sensitivity to N-acylethanolamines. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 12197-12202
54. Pollmann S., Neu D., Lehmann T., Berkowitz O., Schafer T., and Weiler E.W. Subcellular localization and tissue specific expression of amidase 1 from Arabidopsis thaliana. Planta 224 (2006) 1241-1253
55. Nishimura N., Yoshida T., Kitahata N., Asami T., Shinozaki K., and Hirayama T. ABA-hypersensitive germination1 encodes a protein phosphatase 2C, an essential component of abscisic acid signaling in Arabidopsis seed. Plant J. 50 (2007) 935-949
56. Patricelli M.P., and Cravatt B.F. Clarifying the catalytic roles of conserved residues in the amidase signature family. J. Biol. Chem. 275 (2000) 19177-19184
57. Tsuboi K., Takezaki N., and Ueda N. The N-acylethanolamine-hydrolyzing acid amidase (NAAA). Chem. Biodivers. 4 (2007) 1914-1925
58. Wei B.Q., Mikkelsen T.S., McKinney M.K., Lander E.S., and Cravatt B.F. A second fatty acid amide hydrolase with variable distribution among placental mammals. J. Biol. Chem. 281 (2006) 36569-36578
59. Solorzano C., et al. Selective N-acylethanolamine-hydrolyzing acid amidase inhibition reveals a key role for endogenous palmitoylethanolamide in inflammation. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 20966-20971
60. Okamoto Y., Morishita J., Tsuboi K., Tonai T., and Ueda N. Molecular characterization of a phospholipase D generating anandamide and its congeners. J. Biol. Chem. 279 (2004) 5298-5305
61. Okamoto Y., et al. Mammalian cells stably overexpressing N-acylphosphatidylethanolamine-hydrolysing phospholipase D exhibit significantly decreased levels of N-acylphosphatidylethanolamines. Biochem. J. 389 (2005) 241-247
62. Chapman K.D. Emerging physiological roles for N-acylphosphatidylethanolamine metabolism in plants: signal transduction and membrane protection. Chem. Phys. Lipids 108 (2000) 221-229
63. Pappan K., Austin-Brown S., Chapman K.D., and Wang X. Substrate selectivities and lipid modulation of plant phospholipase D-alpha, -beta, and -gamma. Arch. Biochem. Biophys. 353 (1998) 131-140
64. Wang X. Lipid signaling. Curr. Opin. Plant Biol. 7 (2004) 329-336
65. Sun Y.X., et al. Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A 2 and lysophospholipase D. Biochem. J. 380 Pt. (2004) 749-756
66. Simon G.M., and Cravatt B.F. Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain. J. Biol. Chem. 283 (2008) 9341-9349
67. Simon G.M., and Cravatt B.F. Endocannabinoid biosynthesis proceeding through glycerophospho-N-acyl ethanolamine and a role for alpha/beta-hydrolase 4 in this pathway. J. Biol. Chem. 281 (2006) 26465-26472
68. Liu J., et al. Multiple pathways involved in the biosynthesis of anandamide. Neuropharmacology 54 (2008) 1-7
69. Okamoto Y., Tsuboi K., and Ueda N. Enzymatic formation of anandamide. Vitam. Horm. 81 (2009) 1-24
70. Schmid H.H., Schmid P.C., and Natarajan V. The N-acylation-phosphodiesterase pathway and cell signalling. Chem. Phys. Lipids 80 (1996) 133-142
71. McAndrew R.S., and Chapman K.D. Enzymology of cottonseed microsomal N-acylphosphatidylethanolamine synthase: kinetic properties and mechanism-based inactivation. Biochim. Biophys. Acta 1390 (1998) 21-36
72. Chapman K.D., and Moore Jr. T.S. N-acylphosphatidylethanolamine synthesis in plants: occurrence, molecular composition, and phospholipid origin. Arch. Biochem. Biophys. 301 (1993) 21-33
73. Faure L., et al. Discovery and characterization of an Arabidopsis thaliana N-acylphosphatidylethanolamine synthase. J. Biol. Chem. 284 (2009) 18734-18741
74. Yates M.L., and Barker E.L. A role for the FAAH-interacting protein ERp57 in endogenous cannabinoid signaling. FASEB 21 (2007) A1177-A11177
75. Gasperi V., Fezza F., Spagnuolo P., Pasquariello N., and Maccarrone M. Further insights into the regulation of human FAAH by progesterone and leptin-implications for endogenous levels of anandamide and apoptosis of immune and neuronal cells. Neurotoxicology 26 (2005) 811-817
76. Maccarrone M., Gasperi V., Fezza F., Finazzi-Agro A., and Rossi A. Differential regulation of fatty acid amide hydrolase promoter in human immune cells and neuronal cells by leptin and progesterone. Eur. J. Biochem. 271 (2004) 4666-4676
77. Rossi G., Gasperi V., Paro R., Barsacchi D., Cecconi S., and Maccarrone M. Follicle-stimulating hormone activates fatty acid amide hydrolase by protein kinase A and aromatase-dependent pathways in mouse primary sertoli cells. Endocrinology 148 (2007) 1431-1439
78. De Petrocellis L., and Di Marzo V. An introduction to the endocannabinoid system: from the early to the latest concepts. Best Pract. Res. Clin. Endocrinol. Metab. 23 (2009) 1-15
79. Kaczocha M., Glaser S.T., and Deutsch D.G. Identification of intracellular carriers for the endocannabinoid anandamide. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 6375-6380
80. McKinney M.K., and Cravatt B.F. Structure and function of fatty acid amide hydrolase. Annu. Rev. Biochem. 74 (2005) 411-432
81. Zhang Y., Guo W.M., Chen S.M., Han L., and Li Z.M. The role of N-lauroylethanolamine in the regulation of senescence of cut carnations (Dianthus caryophyllus). J. Plant. Physiol. 164 (2007) 993-1001
82. Han L., Gao J.R., Li Z.M., Zhang Y., and Guo W.M. Synthesis of new plant growth regulator: N-(fatty acid) O-aryloxyacetyl ethanolamine. Bioorg. Med. Chem. Lett. 17 (2007) 3231-3234
83. Ramirez-Chavez E., Lopez-Bucio J., Herrera-Estrella L., and Molina-Torres J. Alkamides isolated from plants promote growth and alter root development in Arabidopsis. Plant Physiol. 134 (2004) 1058-1068
84. Campos-Cuevas J.C., et al. Tissue culture of Arabidopsis thaliana explants reveals a stimulatory effect of alkamides on adventitious root formation and nitric oxide accumulation. Plant Sci. 174 (2008) 165-173