Enzymological studies on the biosynthesis of N-acylethanolamines

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1801, Issue 12, 2010, Pages 1274-1285

  Ueda, Natsuo ^a   Tsuboi, Kazuhito ^a   Uyama, Toru ^a  

^a KAGAWA UNIVERSITY   (Japan)

Author keywords

Anandamide; Endocannabinoid; HRASLS family; Lipid mediator; N acylphosphatidylethanolamine; Phospholipase

Indexed keywords

ACYLTRANSFERASE; ENZYME INHIBITOR; ETHANOLAMINE DERIVATIVE; GLYCEROPHOSPHODIESTER PHOSPHODIESTERASE; GLYCEROPHOSPHOLIPID; N ACYLETHANOLAMINE DERIVATIVE; N ACYLPHOSPHATIDYLETHANOLAMINE; PHOSPHATASE; PHOSPHATIDYLETHANOLAMINE; PHOSPHODIESTERASE; PHOSPHOLIPASE A2; PHOSPHOLIPASE C; PHOSPHOLIPASE D; UNCLASSIFIED DRUG;

ACYLATION; CATALYSIS; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME STRUCTURE; LIPOGENESIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVIEW;

ACYLATION; ANIMALS; CATALYSIS; ETHANOLAMINES; HUMANS;

ANIMALIA; MAMMALIA;

EID: 77957944897     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbalip.2010.08.010     Document Type: Review

References (155)

1. Schmid H.H.O., Schmid P.C., Natarajan V. N-acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 1990, 29:1-43.
2. Hansen H.H., Schmid P.C., Bittigau P., Lastres-Becker I., Berrendero F., Manzanares J., Ikonomidou C., Schmid H.H.O., Fernández-Ruiz J.J., Hansen H.S. Anandamide, but not 2-arachidonoylglycerol, accumulates during in vivo neurodegeneration. J. Neurochem. 2001, 78:1415-1427.
3. Hansen H.S., Diep T.A. N-acylethanolamines, anandamide and food intake. Biochem. Pharmacol. 2009, 78:553-560.
4. Di Marzo V. 'Endocannabinoids' and other fatty acid derivatives with cannabimimetic properties: biochemistry and possible physiopathological relevance. Biochim. Biophys. Acta 1998, 1392:153-175.
5. Pacher P., Bátkai S., Kunos G. The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol. Rev. 2006, 58:389-462.
6. Kuehl F.A., Jacob T.A., Ganley O.H., Ormond R.E., Meisinger M.A.P. The identification of N-(2-hydroxyethyl)-palmitamide as a naturally occurring anti-inflammatory agent. J. Am. Chem. Soc. 1957, 79:5577-5578.
7. Bachur N.R., Masek K., Melmon K.L., Udenfriend S. Fatty acid amides of ethanolamine in mammalian tissues. J. Biol. Chem. 1965, 240:1019-1024.
8. LoVerme J., La Rana G., Russo R., Calignano A., Piomelli D. The search for the palmitoylethanolamide receptor. Life Sci. 2005, 77:1685-1698.
9. Schmid P.C., Zuzarte-Augustin M.L., Schmid H.H.O. Properties of rat liver N-acylethanolamine amidohydrolase. J. Biol. Chem. 1985, 260:14145-14149.
10. Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., Gilula N.B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 1996, 384:83-87.
11. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mechoulam R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992, 258:1946-1949.
12. Deutsch D.G., Chin S.A. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem. Pharmacol. 1993, 46:791-796.
13. Di Marzo V., Fontana A., Cadas H., Schinelli S., Cimino G., Schwartz J.C., Piomelli D. Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature 1994, 372:686-691.
14. Sugiura T., Kondo S., Sukagawa A., Tonegawa T., Nakane S., Yamashita A., Ishima Y., Waku K. Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonoylethanolamine, an endogenous cannabinoid-receptor ligand, in rat brain microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine. Eur. J. Biochem. 1996, 240:53-62.
15. Hanus L., Gopher A., Almog S., Mechoulam R. Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J. Med. Chem. 1993, 36:3032-3034.
16. Priller J., Briley E.M., Mansouri J., Devane W.A., Mackie K., Felder C.C. Mead ethanolamide, a novel eicosanoid, is an agonist for the central (CB1) and peripheral (CB2) cannabinoid receptors. Mol. Pharmacol. 1995, 48:288-292.
17. Felder C.C., Briley E.M., Axelrod J., Simpson J.T., Mackie K., Devane W.A. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA 1993, 90:7656-7660.
18. Lambert D.M., Vandevoorde S., Jonsson K.O., Fowler C.J. The palmitoylethanolamide family: a new class of anti-inflammatory agents?. Curr. Med. Chem. 2002, 9:663-674.
19. Lo Verme J., Fu J., Astarita G., La Rana G., Russo R., Calignano A., Piomelli D. The nuclear receptor peroxisome proliferator-activated receptor-α mediates the anti-inflammatory actions of palmitoylethanolamide. Mol. Pharmacol. 2005, 67:15-19.
20. Rodríguez de Fonseca F., Navarro M., Gómez R., Escuredo L., Nava F., Fu J., Murillo-Rodríguez E., Giuffrida A., LoVerme J., Gaetani S., Kathuria S., Gall C., Piomelli D. An anorexic lipid mediator regulated by feeding. Nature 2001, 414:209-212.
21. Nielsen M.J., Petersen G., Astrup A., Hansen H.S. Food intake is inhibited by oral oleoylethanolamide. J. Lipid Res. 2004, 45:1027-1029.
22. Fu J., Gaetani S., Oveisi F., Lo Verme J., Serrano A., Rodríguez De Fonseca F., Rosengarth A., Luecke H., Di Giacomo B., Tarzia G., Piomelli D. Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α. Nature 2003, 425:90-93.
23. Overton H.A., Babbs A.J., Doel S.M., Fyfe M.C.T., Gardner L.S., Griffin G., Jackson H.C., Procter M.J., Rasamison C.M., Tang-Christensen M., Widdowson P.S., Williams G.M., Reynet C. Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents. Cell Metab. 2006, 3:167-175.
24. Lauffer L.M., Iakoubov R., Brubaker P.L. GPR119 is essential for oleoylethanolamide-induced glucagon-like peptide-1 secretion from the intestinal enteroendocrine L-cell. Diabetes 2009, 58:1058-1066.
25. Sandoval J.A., Huang Z.H., Garrett D.C., Gage D.A., Chapman K.D. N-acylphosphatidylethanolamine in dry and imbibing cottonseeds. Amounts, molecular species, and enzymatic synthesis. Plant Physiol. 1995, 109:269-275.
26. Gillum M.P., Zhang D., Zhang X.-M., Erion D.M., Jamison R.A., Choi C., Dong J., Shanabrough M., Duenas H.R., Frederick D.W., Hsiao J.J., Horvath T.L., Lo C.M., Tso P., Cline G.W., Shulman G.I. N-acylphosphatidylethanolamine, a gut-derived circulating factor induced by fat ingestion, inhibits food intake. Cell 2008, 135:813-824.
27. Shiratsuchi A., Ichiki M., Okamoto Y., Ueda N., Sugimoto N., Takuwa Y., Nakanishi Y. Inhibitory effect of N-palmitoylphosphatidylethanolamine on macrophage phagocytosis through inhibition of Rac1 and Cdc42. J. Biochem. 2009, 145:43-50.
28. Di Marzo V. Targeting the endocannabinoid system: to enhance or reduce?. Nat. Rev. Drug Discov. 2008, 7:438-455.
29. Di Marzo V. Endocannabinoids: synthesis and degradation. Rev. Physiol. Biochem. Pharmacol. 2008, 160:1-24.
30. Ahn K., McKinney M.K., Cravatt B.F. Enzymatic pathways that regulate endocannabinoid signaling in the nervous system. Chem. Rev. 2008, 108:1687-1707.
31. Farrell E.K., Merkler D.J. Biosynthesis, degradation and pharmacological importance of the fatty acid amides. Drug Discov. Today 2008, 13:558-568.
32. Wang J., Ueda N. Biology of endocannabinoid synthesis system. Prostaglandins Other Lipid Mediat. 2009, 89:112-119.
33. Okamoto Y., Tsuboi K., Ueda N. Enzymatic formation of anandamide. Vitam. Horm. 2009, 81:1-24.
34. Ueda N., Tsuboi K., Uyama T. N-acylethanolamine metabolism with special reference to N-acylethanolamine-hydrolyzing acid amidase (NAAA). Prog. Lipid Res. 2010, 10.1016/j.plipres.2010.02.003.
35. Hansen H.S., Moesgaard B., Hansen H.H., Petersen G. N-Acylethanolamines and precursor phospholipids - relation to cell injury. Chem. Phys. Lipids 2000, 108:135-150.
36. Schmid H.H.O. Pathways and mechanisms of N-acylethanolamine biosynthesis: can anandamide be generated selectively?. Chem. Phys. Lipids 2000, 108:71-87.
37. Okamoto Y., Morishita J., Tsuboi K., Tonai T., Ueda N. Molecular characterization of a phospholipase D generating anandamide and its congeners. J. Biol. Chem. 2004, 279:5298-5305.
38. 2+-independent phosphatidylethanolamine N-acyltransferase generating the anandamide precursor and its congeners. J. Biol. Chem. 2007, 282:3614-3623.
39. Uyama T., Jin X.-H., Tsuboi K., Tonai T., Ueda N. Characterization of the human tumor suppressors TIG3 and HRASLS2 as phospholipid-metabolizing enzymes. Biochim. Biophys. Acta 2009, 1791:1114-1124.
40. Leung D., Saghatelian A., Simon G.M., Cravatt B.F. Inactivation of N-acyl phosphatidylethanolamine phospholipase D reveals multiple mechanisms for the biosynthesis of endocannabinoids. Biochemistry 2006, 45:4720-4726.
41. Simon G.M., Cravatt B.F. Endocannabinoid biosynthesis proceeding through glycerophospho-N-acyl ethanolamine and a role for α/β-hydrolase 4 in this pathway. J. Biol. Chem. 2006, 281:26465-26472.
42. Liu J., Wang L., Harvey-White J., Osei-Hyiaman D., Razdan R., Gong Q., Chan A.C., Zhou Z., Huang B.X., Kim H.Y., Kunos G. A biosynthetic pathway for anandamide. Proc. Natl. Acad. Sci. USA 2006, 103:13345-13350.
43. Simon G.M., Cravatt B.F. Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain. J. Biol. Chem. 2008, 283:9341-9349.
44. Liu J., Wang L., Harvey-White J., Huang B.X., Kim H.-Y., Luquet S., Palmiter R.D., Krystal G., Rai R., Mahadevan A., Razdan R.K., Kunos G. Multiple pathways involved in the biosynthesis of anandamide. Neuropharmacology 2008, 54:1-7.
45. Katayama K., Ueda N., Katoh I., Yamamoto S. Equilibrium in the hydrolysis and synthesis of cannabimimetic anandamide demonstrated by a purified enzyme. Biochim. Biophys. Acta 1999, 1440:205-214.
46. Tsuboi K., Sun Y.-X., Okamoto Y., Araki N., Tonai T., Ueda N. 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. 2005, 280:11082-11092.
47. Wei B.Q., Mikkelsen T.S., McKinney M.K., Lander E.S., Cravatt B.F. A second fatty acid amide hydrolase with variable distribution among placental mammals. J. Biol. Chem. 2006, 281:36569-36578.
48. McKinney M.K., Cravatt B.F. Structure and function of fatty acid amide hydrolase. Annu. Rev. Biochem. 2005, 74:411-432.
49. Cravatt B.F., Demarest K., Patricelli M., Bracey M.H., Giang D.K., Martin B.R., Lichtman A.H. Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase. Proc. Natl. Acad. Sci. USA 2001, 98:9371-9376.
50. Bracey M.H., Hanson M.A., Masuda K.R., Stevens R.C., Cravatt B.F. Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling. Science 2002, 298:1793-1796.
51. Ahn K., Johnson D.S., Mileni M., Beidler D., Long J.Z., McKinney M.K., Weerapana E., Sadagopan N., Liimatta M., Smith S.E., Lazerwith S., Stiff C., Kamtekar S., Bhattacharya K., Zhang Y., Swaney S., Van Becelaere K., Stevens R.C., Cravatt B.F. Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain. Chem. Biol. 2009, 16:411-420.
52. Kaczocha M., Glaser S.T., Chae J., Brown D.A., Deutsch D.G. Lipid droplets are novel sites of N-acylethanolamine inactivation by fatty acid amide hydrolase-2. J. Biol. Chem. 2010, 285:2796-2806.
53. Tsuboi K., Takezaki N., Ueda N. The N-acylethanolamine-hydrolyzing acid amidase (NAAA). Chem. Biodivers. 2007, 4:1914-1925.
54. Solorzano C., Zhu C., Battista N., Astarita G., Lodola A., Rivara S., Mor M., Russo R., Maccarrone M., Antonietti F., Duranti A., Tontini A., Cuzzocrea S., Tarzia G., Piomelli D. Selective N-acylethanolamine-hydrolyzing acid amidase inhibition reveals a key role for endogenous palmitoylethanolamide in inflammation. Proc. Natl. Acad. Sci. USA 2009, 106:20966-20971.
55. Vandevoorde S., Lambert D.M. The multiple pathways of endocannabinoid metabolism: a zoom out. Chem. Biodivers. 2007, 4:1858-1881.
56. Fowler C.J. The contribution of cyclooxygenase-2 to endocannabinoid metabolism and action. Br. J. Pharmacol. 2007, 152:594-601.
57. Rouzer C.A., Marnett L.J. Non-redundant functions of cyclooxygenases: oxygenation of endocannabinoids. J. Biol. Chem. 2008, 283:8065-8069.
58. Stark K., Dostalek M., Guengerich F.P. Expression and purification of orphan cytochrome P450 4X1 and oxidation of anandamide. FEBS J. 2008, 275:3706-3717.
59. Snider N.T., Sikora M.J., Sridar C., Feuerstein T.J., Rae J.M., Hollenberg P.F. The endocannabinoid anandamide is a substrate for the human polymorphic cytochrome P450 2D6. J. Pharmacol. Exp. Ther. 2008, 327:538-545.
60. Natarajan V., Reddy P.V., Schmid P.C., Schmid H.H.O. N-Acylation of ethanolamine phospholipids in canine myocardium. Biochim. Biophys. Acta 1982, 712:342-355.
61. Cadas H., di Tomaso E., Piomelli D. Occurrence and biosynthesis of endogenous cannabinoid precursor, N-arachidonoyl phosphatidylethanolamine, in rat brain. J. Neurosci. 1997, 17:1226-1242.
62. 2+-dependent transacylase and phosphodiesterase activities. Biochem. Biophys. Res. Commun. 1996, 218:113-117.
63. Astarita G., Ahmed F., Piomelli D. Identification of biosynthetic precursors for the endocannabinoid anandamide in the rat brain. J. Lipid Res. 2008, 49:48-57.
64. Fu J., Astarita G., Gaetani S., Kim J., Cravatt B.F., Mackie K., Piomelli D. Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine. J. Biol. Chem. 2007, 282:1518-1528.
65. Epps D.E., Schmid P.C., Natarajan V., Schmid H.H.O. N-Acylethanolamine accumulation in infarcted myocardium. Biochem. Biophys. Res. Commun. 1979, 90:628-633.
66. Epps D.E., Natarajan V., Schmid P.C., Schmid H.H.O. Accumulation of N-acylethanolamine glycerophospholipids in infarcted myocardium. Biochim. Biophys. Acta 1980, 618:420-430.
67. Hansen H.S., Lauritzen L., Strand A.M., Moesgaard B., Frandsen A. Glutamate stimulates the formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cortical neurons in culture. Biochim. Biophys. Acta 1995, 1258:303-308.
68. Schmid P.C., Krebsbach R.J., Perry S.R., Dettmer T.M., Maasson J.L., Schmid H.H.O. Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain. FEBS Lett. 1995, 375:117-120.
69. Kondo S., Sugiura T., Kodaka T., Kudo N., Waku K., Tokumura A. Accumulation of various N-acylethanolamines including N-arachidonoylethanolamine (anandamide) in cadmium chloride-administered rat testis. Arch. Biochem. Biophys. 1998, 354:303-310.
70. + cells. Biochem. J. 2000, 346:369-374.
71. 31P NMR and enzyme activity study. J. Lipid Res. 2000, 41:985-990.
72. Cadas H., Gaillet S., Beltramo M., Venance L., Piomelli D. Biosynthesis of an endogenous cannabinoid precursor in neurons and its control by calcium and cAMP. J. Neurosci. 1996, 16:3934-3942.
73. Reddy P.V., Schmid P.C., Natarajan V., Muramatsu T., Schmid H.H.O. Properties of canine myocardial phosphatidylethanolamine N-acyltransferase. Biochim. Biophys. Acta 1984, 795:130-136.
74. Natarajan V., Schmid P.C., Schmid H.H.O. N-Acylethanolamine phospholipid metabolism in normal and ischemic rat brain. Biochim. Biophys. Acta 1986, 878:32-41.
75. Moesgaard B., Hansen H.H., Hansen S.L., Hansen S.H., Petersen G., Hansen H.S. Brain levels of N-acylethanolamine phospholipids in mice during pentylenetetrazol-induced seizure. Lipids 2003, 38:387-390.
76. Morishita J., Okamoto Y., Tsuboi K., Ueno M., Sakamoto H., Maekawa N., Ueda N. Regional distribution and age-dependent expression of N-acylphosphatidylethanolamine-hydrolyzing phospholipase D in rat brain. J. Neurochem. 2005, 94:753-762.
77. Moesgaard B., Petersen G., Mortensen S.A., Hansen H.S. Substantial species differences in relation to formation and degradation of N-acyl-ethanolamine phospholipids in heart tissue: an enzyme activity study. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 2002, 131:475-482.
78. Thabuis C., Tissot-Favre D., Bezelgues J.B., Martin J.C., Cruz-Hernandez C., Dionisi F., Destaillats F. Biological functions and metabolism of oleoylethanolamide. Lipids 2008, 43:887-894.
79. Petersen G., Sørensen C., Schmid P.C., Artmann A., Tang-Christensen M., Hansen S.H., Larsen P.J., Schmid H.H.O., Hansen H.S. Intestinal levels of anandamide and oleoylethanolamide in food-deprived rats are regulated through their precursors. Biochim. Biophys. Acta 2006, 1761:143-150.
80. Schwartz G.J., Fu J., Astarita G., Li X., Gaetani S., Campolongo P., Cuomo V., Piomelli D. The lipid messenger OEA links dietary fat intake to satiety. Cell Metab. 2008, 8:281-288.
81. Guijarro A., Fu J., Astarita G., Piomelli D. CD36 gene deletion decreases oleoylethanolamide levels in small intestine of free-feeding mice. Pharmacol. Res. 2010, 61:27-33.
82. Faure L., Coulon D., Laroche-Traineau J., Le Guedard M., Schmitter J.M., Testet E., Lessire R., Bessoule J.J. Discovery and characterization of an Arabidopsis thaliana N-acylphosphatidylethanolamine synthase. J. Biol. Chem. 2009, 284:18734-18741.
83. Rando R.R. Membrane-bound lecithin-retinol acyltransferase. Biochem. Biophys. Res. Commun. 2002, 292:1243-1250.
84. Ruiz A., Winston A., Lim Y.-H., Gilbert B.A., Rando R.R., Bok D. Molecular and biochemical characterization of lecithin retinol acyltransferase. J. Biol. Chem. 1999, 274:3834-3841.
85. Zolfaghari R., Ross A.C. Lecithin:retinol acyltransferase from mouse and rat liver: cDNA cloning and liver-specific regulation by dietary vitamin A and retinoic acid. J. Lipid Res. 2000, 41:2024-2034.
86. Golczak M., Imanishi Y., Kuksa V., Maeda T., Kubota R., Palczewski K. Lecithin:retinol acyltransferase is responsible for amidation of retinylamine, a potent inhibitor of the retinoid cycle. J. Biol. Chem. 2005, 280:42263-42273.
87. Anantharaman V., Aravind L. Evolutionary history, structural features and biochemical diversity of the NlpC/P60 superfamily of enzymes. Genome Biol. 2003, 4:R11.
88. Jahng W.J., Xue L., Rando R.R. Lecithin retinol acyltransferase is a founder member of a novel family of enzymes. Biochemistry 2003, 42:12805-12812.
89. Shyu R.Y., Hsieh Y.C., Tsai F.M., Wu C.C., Jiang S.Y. Cloning and functional characterization of the HRASLS2 gene. Amino Acids 2008, 35:129-137.
90. 2+-independent phosphatidylethanolamine N-acyltransferases. Biochim. Biophys. Acta 2009, 1791:32-38.
91. Yamano Y., Asano A., Ohyama K., Ohta M., Nishio R., Morishima I. Expression of the Ha-ras suppressor family member 5 gene in the maturing rat testis. Biosci. Biotechnol. Biochem. 2008, 72:1360-1363.
92. Shi Y.Q., Hubacek I., Rando R.R. Kinetic mechanism of lecithin retinol acyl transferase. Biochemistry 1993, 32:1257-1263.
93. 1/2 of the thiol hydrolase-type. J. Lipid Res. 2009, 50:685-693.
94. Hajnal A., Klemenz R., Schäfer R. Subtraction cloning of H-rev107, a gene specifically expressed in H-ras resistant fibroblasts. Oncogene 1994, 9:479-490.
95. Sers C., Emmenegger U., Husmann K., Bucher K., Andres A.C., Schäfer R. Growth-inhibitory activity and downregulation of the class II tumor-suppressor gene H-rev107 in tumor cell lines and experimental tumors. J. Cell Biol. 1997, 136:935-944.
96. Nazarenko I., Schäfer R., Sers C. Mechanisms of the HRSL3 tumor suppressor function in ovarian carcinoma cells. J. Cell Sci. 2007, 120:1393-1404.
97. DiSepio D., Ghosn C., Eckert R.L., Deucher A., Robinson N., Duvic M., Chandraratna R.A., Nagpal S. Identification and characterization of a retinoid-induced class II tumor suppressor/growth regulatory gene. Proc. Natl. Acad. Sci. USA 1998, 95:14811-14815.
98. Huang S.L., Shyu R.Y., Yeh M.Y., Jiang S.Y. Cloning and characterization of a novel retinoid-inducible gene 1 (RIG1) deriving from human gastric cancer cells. Mol. Cell. Endocrinol. 2000, 159:15-24.
99. Tsai F.M., Shyu R.Y., Jiang S.Y. RIG1 inhibits the Ras/mitogen-activated protein kinase pathway by suppressing the activation of Ras. Cell. Signal. 2006, 18:349-358. Erratum 18 (2006) 1097-1098.
100. Eckert R.L., Sturniolo M.T., Jans R., Kraft C.A., Jiang H., Rorke E.A. TIG3: a regulator of type I transglutaminase activity in epidermis. Amino Acids 2009, 36:739-746.
101. 2 (AdPLA). J. Biol. Chem. 2008, 283:25428-25436.
102. Jaworski K., Ahmadian M., Duncan R.E., Sarkadi-Nagy E., Varady K.A., Hellerstein M.K., Lee H.Y., Samuel V.T., Shulman G.I., Kim K.H., de Val S., Kang C., Sul H.S. AdPLA ablation increases lipolysis and prevents obesity induced by high-fat feeding or leptin deficiency. Nat. Med. 2009, 15:159-168.
103. Kilaru A., Blancaflor E.B., Venables B.J., Tripathy S., Mysore K.S., Chapman K.D. The N-acylethanolamine-mediated regulatory pathway in plants. Chem. Biodivers. 2007, 4:1933-1955.
104. 2+-dependent phospholipase D. Protein Sci. 2002, 11:2958-2968.
105. 2 and D: a method of identification and analysis. Chem. Phys. Lipids 1986, 41:195-207.
106. Natarajan V., Reddy P.V., Schmid P.C., Schmid H.H.O. On the biosynthesis and metabolism of N-acylethanolamine phospholipids in infarcted dog heart. Biochim. Biophys. Acta 1981, 664:445-448.
107. Schmid P.C., Reddy P.V., Natarajan V., Schmid H.H.O. Metabolism of N-acylethanolamine phospholipids by a mammalian phosphodiesterase of the phospholipase D type. J. Biol. Chem. 1983, 258:9302-9306.
108. Natarajan V., Schmid P.C., Reddy P.V., Schmid H.H.O. Catabolism of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 1984, 42:1613-1619.
109. Petersen G., Hansen H.S. N-acylphosphatidylethanolamine-hydrolysing phospholipase D lacks the ability to transphosphatidylate. FEBS Lett. 1999, 455:41-44.
110. Ueda N., Liu Q., Yamanaka K. Marked activation of the N-acylphosphatidylethanolamine-hydrolyzing phosphodiesterase by divalent cations. Biochim. Biophys. Acta 2001, 1532:121-127.
111. Liu Q., Tonai T., Ueda N. Activation of N-acylethanolamine-releasing phospholipase D by polyamines. Chem. Phys. Lipids 2002, 115:77-84.
112. Curtiss N.P., Bonifas J.M., Lauchle J.O., Balkman J.D., Kratz C.P., Emerling B.M., Green E.D., Le Beau M.M., Shannon K.M. Isolation and analysis of candidate myeloid tumor suppressor genes from a commonly deleted segment of 7q22. Genomics 2005, 85:600-607.
113. Ueda N., Okamoto Y., Morishita J. N-acylphosphatidylethanolamine-hydrolyzing phospholipase D: a novel enzyme of the β-lactamase fold family releasing anandamide and other N-acylethanolamines. Life Sci. 2005, 77:1750-1758.
114. McPartland J.M., Matias I., Di Marzo V., Glass M. Evolutionary origins of the endocannabinoid system. Gene 2006, 370:64-74.
115. Merkel O., Schmid P.C., Paltauf F., Schmid H.H.O. Presence and potential signaling function of N-acylethanolamines and their phospholipid precursors in the yeast Saccharomyces cerevisiae. Biochim. Biophys. Acta 2005, 1734:215-219.
116. Muccioli G.G., Sia A., Muchowski P.J., Stella N. Genetic manipulation of palmitoylethanolamide production and inactivation in Saccharomyces cerevisiae. PLoS ONE 2009, 4:e5942.
117. Aravind L. An evolutionary classification of the metallo-beta-lactamase fold proteins. In Silico Biol. 1999, 1:69-91.
118. Daiyasu H., Osaka K., Ishino Y., Toh H. Expansion of the zinc metallo-hydrolase family of the β-lactamase fold. FEBS Lett. 2001, 503:1-6.
119. Liscovitch M., Czarny M., Fiucci G., Tang X. Phospholipase D: molecular and cell biology of a novel gene family. Biochem. J. 2000, 345:401-415.
120. Hammond S.M., Altshuller Y.M., Sung T.-C., Rudge S.A., Rose K., Engebrecht J., Morris A.J., Frohman M.A. Human ADP-ribosylation factor-activated phosphatidylcholine-specific phospholipase D defines a new and highly conserved gene family. J. Biol. Chem. 1995, 270:29640-29643.
121. Colley W.C., Sung T.-C., Roll R., Jenco J., Hammond S.M., Altshuller Y., Bar-Sagi D., Morris A.J., Frohman M.A. Phospholipase D2, a distinct phospholipase D isoform with novel regulatory properties that provokes cytoskeletal reorganization. Curr. Biol. 1997, 7:191-201.
122. Wang J., Okamoto Y., Morishita J., Tsuboi K., Miyatake A., Ueda N. Functional analysis of the purified anandamide-generating phospholipase D as a member of the metallo-β-lactamase family. J. Biol. Chem. 2006, 281:12325-12335.
123. Wang Z., Fast W., Valentine A.M., Benkovic S.J. Metallo-β-lactamase: structure and mechanism. Curr. Opin. Chem. Biol. 1999, 3:614-622.
124. Sasaki T., Chang M.C. N-arachidonylethanolamine (anandamide) formation from N-arachidonylphosphatidylethanolamine in rat brain membranes. Life Sci. 1997, 61:1803-1810.
125. Petersen G., Pedersen A.H., Pickering D.S., Begtrup M., Hansen H.S. Effect of synthetic and natural phospholipids on N-acylphosphatidylethanolamine-hydrolyzing phospholipase D activity. Chem. Phys. Lipids 2009, 162:53-61.
126. Okamoto Y., Morishita J., Wang J., Schmid P.C., Krebsbach R.J., Schmid H.H.O., Ueda N. Mammalian cells stably overexpressing N-acylphosphatidylethanolamine-hydrolysing phospholipase D exhibit significantly decreased levels of N-acylphosphatidylethanolamines. Biochem. J. 2005, 389:241-247.
127. Wang J., Okamoto Y., Tsuboi K., Ueda N. The stimulatory effect of phosphatidylethanolamine on N-acylphosphatidylethanolamine-hydrolyzing phospholipase D. Neuropharmacology 2008, 54:8-15.
128. Petersen G., Chapman K.D., Hansen H.S. A rapid phospholipase D assay using zirconium precipitation of anionic substrate phospholipids: application to N-acylethanolamine formation in vitro. J. Lipid Res. 2000, 41:1532-1538.
129. Egertová M., Simon G.M., Cravatt B.F., Elphick M.R. Localization of N-acyl phosphatidylethanolamine phospholipase D (NAPE-PLD) expression in mouse brain: a new perspective on N-acylethanolamines as neural signaling molecules. J. Comp. Neurol. 2008, 506:604-615.
130. Nyilas R., Dudok B., Urban G.M., Mackie K., Watanabe M., Cravatt B.F., Freund T.F., Katona I. Enzymatic machinery for endocannabinoid biosynthesis associated with calcium stores in glutamatergic axon terminals. J. Neurosci. 2008, 28:1058-1063.
131. Cristino L., Starowicz K., De Petrocellis L., Morishita J., Ueda N., Guglielmotti V., Di Marzo V. Immunohistochemical localization of anabolic and catabolic enzymes for anandamide and other putative endovanilloids in the hippocampus and cerebellar cortex of the mouse brain. Neuroscience 2008, 151:955-968.
132. Nagy B., Fedonidis C., Photiou A., Wahba J., Paule C.C., Ma D., Buluwela L., Nagy I. Capsaicin-sensitive primary sensory neurons in the mouse express N-acyl phosphatidylethanolamine phospholipase D. Neuroscience 2009, 161:572-577.
133. Fu J., Kim J., Oveisi F., Astarita G., Piomelli D. Targeted enhancement of oleoylethanolamide production in proximal small intestine induces across-meal satiety in rats. Am. J. Physiol. Regul. Integr. Comp. Physiol. 2008, 295:R45-R50.
134. Marquéz L., Suárez J., Iglesias M., Bermudez-Silva F.J., Rodríguez de Fonseca F., Andreu M. Ulcerative colitis induces changes on the expression of the endocannabinoid system in the human colonic tissue. PLoS ONE 2009, 4:e6893.
135. Guo Y., Wang H., Okamoto Y., Ueda N., Kingsley P.J., Marnett L.J., Schmid H.H.O., Das S.K., Dey S.K. N-acylphosphatidylethanolamine-hydrolyzing phospholipase D is an important determinant of uterine anandamide levels during implantation. J. Biol. Chem. 2005, 280:23429-23432.
136. Wang H., Xie H., Guo Y., Zhang H., Takahashi T., Kingsley P.J., Marnett L.J., Das S.K., Cravatt B.F., Dey S.K. Fatty acid amide hydrolase deficiency limits early pregnancy events. J. Clin. Invest. 2006, 116:2122-2131.
137. Wang J., Zhao L.-Y., Uyama T., Tsuboi K., Wu X.-X., Kakehi Y., Ueda N. Expression and secretion of N-acylethanolamine-hydrolysing acid amidase in human prostate cancer cells. J. Biochem. 2008, 144:685-690.
138. Clement A.B., Hawkins E.G., Lichtman A.H., Cravatt B.F. Increased seizure susceptibility and proconvulsant activity of anandamide in mice lacking fatty acid amide hydrolase. J. Neurosci. 2003, 23:3916-3923.
139. 2 and lysophospholipase D. Biochem. J. 2004, 380:749-756.
140. Renault L., Nègre V., Hotelier T., Cousin X., Marchot P., Chatonnet A. New friendly tools for users of ESTHER, the database of the alpha/beta-hydrolase fold superfamily of proteins. Chem. Biol. Interact. 2005, 157-158:339-343.
141. Blankman J.L., Simon G.M., Cravatt B.F. A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. Chem. Biol. 2007, 14:1347-1356.
142. Zheng B., Chen D., Farquhar M.G. MIR16, a putative membrane glycerophosphodiester phosphodiesterase, interacts with RGS16. Proc. Natl. Acad. Sci. USA 2000, 97:3999-4004.
143. Bachmann A.S., Duennebier F.F., Mocz G. Genomic organization, characterization, and molecular 3D model of GDE1, a novel mammalian glycerophosphoinositol phosphodiesterase. Gene 2006, 371:144-153.
144. Zheng B., Berrie C.P., Corda D., Farquhar M.G. GDE1/MIR16 is a glycerophosphoinositol phosphodiesterase regulated by stimulation of G protein-coupled receptors. Proc. Natl. Acad. Sci. USA 2003, 100:1745-1750.
145. Simon G.M., Cravatt B.F. Characterization of mice lacking candidate N-acyl ethanolamine biosynthetic enzymes provides evidence for multiple pathways that contribute to endocannabinoid production in vivo. Mol. Biosyst. 2010, 6:1411-1418.
146. Liu J., Batkai S., Pacher P., Harvey-White J., Wagner J.A., Cravatt B.F., Gao B., Kunos G. Lipopolysaccharide induces anandamide synthesis in macrophages via CD14/MAPK/phosphoinositide 3-kinase/NF-kappaB independently of platelet-activating factor. J. Biol. Chem. 2003, 278:45034-45039.
147. Cohen S., Dadi H., Shaoul E., Sharfe N., Roifman C.M. Cloning and characterization of a lymphoid-specific, inducible human protein tyrosine phosphatase. Lyp. Blood 1999, 93:2013-2024.
148. An H., Xu H., Zhang M., Zhou J., Feng T., Qian C., Qi R., Cao X. Src homology 2 domain-containing inositol-5-phosphatase 1 (SHIP1) negatively regulates TLR4-mediated LPS response primarily through a phosphatase activity- and PI-3K-independent mechanism. Blood 2005, 105:4685-4692.
149. Bachur N.R., Udenfriend S. Microsomal synthesis of fatty acid amides. J. Biol. Chem. 1966, 241:1308-1313.
150. Kruszka K.K., Gross R.W. The ATP- and CoA-independent synthesis of arachidonoylethanolamide. A novel mechanism underlying the synthesis of the endogenous ligand of the cannabinoid receptor. J. Biol. Chem. 1994, 269:14345-14348.
151. Devane W.A., Axelrod J. Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain membranes. Proc. Natl. Acad. Sci. USA 1994, 91:6698-6701.
152. Ueda N., Kurahashi Y., Yamamoto S., Tokunaga T. Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J. Biol. Chem. 1995, 270:23823-23827.
153. Kempe K., Hsu F.F., Bohrer A., Turk J. Isotope dilution mass spectrometric measurements indicate that arachidonylethanolamide, the proposed endogenous ligand of the cannabinoid receptor, accumulates in rat brain tissue post mortem but is contained at low levels in or is absent from fresh tissue. J. Biol. Chem. 1996, 271:17287-17295.
154. Patel S., Carrier E.J., Ho W.S., Rademacher D.J., Cunningham S., Reddy D.S., Falck J.R., Cravatt B.F., Hillard C.J. The postmortal accumulation of brain N-arachidonylethanolamine (anandamide) is dependent upon fatty acid amide hydrolase activity. J. Lipid Res. 2005, 46:342-349.
155. McCue J.M., Driscoll W.J., Mueller G.P. In vitro synthesis of arachidonoyl amino acids by cytochrome c. Prostaglandins Other Lipid Mediat. 2009, 90:42-48.