N-acylethanolamines, anandamide and food intake

Biochemical Pharmacology

Volumn 78, Issue 6, 2009, Pages 553-560

  Hansen, Harald S ^a   Diep, Thi Ai ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Dietary fat; Food intake; Oleoylethanolamide; Palmitoylethanolamide; Satiety

Indexed keywords

ACYLSPHINGOSINE DEACYLASE; ANANDAMIDE; CANNABINOID RECEPTOR; G PROTEIN COUPLED RECEPTOR; G PROTEIN COUPLED RECEPTOR 119; LINOLEOYLETHANOLAMIDE; N OLEOYLETHANOLAMINE; PALMIDROL; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; STEAROYLETHANOLAMIDE; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1;

ALCOHOL CONSUMPTION; ARTICLE; CALORIC INTAKE; EPILEPSY; FAT INTAKE; FATTY ACID SYNTHESIS; FEEDBACK SYSTEM; FOOD INTAKE; GASTROINTESTINAL TRACT; HUMAN; NONHUMAN; OBESITY; PRIORITY JOURNAL; SATIETY; SIGNAL TRANSDUCTION; VAGUS NERVE; WEIGHT CONTROL;

EID: 67651146366     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2009.04.024     Document Type: Note

References (122)

1. McPartland J.M. Phylogenomic and chemotaxonomic analysis of the endocannabinoid system. Brain Res Rev 45 (2004) 18-29
2. Merkel O., Schmid P.C., Paltauf F., and Schmid H.H.O. Presence and potential signaling function of N-acylethanolamines and their phospholipid precursors in the yeast Saccharomyces cerevisiae. Biochim Biophys Acta 1734 (2005) 215-219
3. Venables B.J., Waggoner C.A., and Chapman K.D. N-acylethanolamines in seeds of selected legumes. Phytochemistry 66 (2005) 1913-1918
4. Fezza F., Dillwith J.W., Bisogno T., Tucker J.S., Di Marzo V., and Sauer J.R. Endocannabinoids and related fatty acid amides, and their regulation, in the salivary glands of the lone star tick. Biochim Biophys Acta Mol Cell Biol Lipids 1633 (2003) 61-67
5. Rademacher D.J., Weber D.N., and Hillard C.J. Waterborne lead exposure affects brain endocannabinoid content in male but not female fathead minnows (Pimephales promelas). Neurotoxicology 26 (2005) 9-15
6. Maag H. Fatty acid derivatives: important surfactants for household, cosmetic and industrial purposes. J Am Oil Chem Soc 61 (1984) 259-267
7. Cravatt B.F., Prospero-Garcia O., Sizudak G., Gilula N.B., Henriksen S.J., Boger D.L., et al. Chemical characterization of a family of brain lipids that induce sleep. Science 268 (1995) 1506-1509
8. McDonald G.R., Hudson A.L., Dunn S.M., You H., Baker G.B., Whittal R.M., et al. Bioactive contaminants leach from disposable laboratory plasticware. Science 322 (2008) 917
9. Williams C.M., and Kirkham T.C. Anandamide induces overeating: mediation by central cannabinoid (CB1) receptors. Psychopharmacology (Berl) 143 (1999) 315-317
10. Oz M. Receptor-independent actions of cannabinoids on cell membranes: Focus on endocannabinoids. Pharmacol Ther 111 (2006) 114-144
11. Rodriguez de Fonseca F., Navarro M., Gómez R., Escuredo L., Nava F., Fu J., et al. An anorexic lipid mediator regulated by feeding. Nature 414 (2001) 209-212
12. Nielsen M.J., Petersen G., Astrup A., and Hansen H.S. Food intake is inhibited by oral oleoylethanolamide. J Lipid Res 45 (2004) 1027-1029
13. Wang X., Miyares R.L., and Ahern G.P. Oleoylethanolamide excites vagal sensory neurons, induces viceral pain and reduces food intake via TRPV1. J Physiol (Lond) 564 (2005) 541-547
14. Overton H.A., Babbs A.J., Doel S.M., Fyfe M.C., Gardner L.S., Griffin G., et al. Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents. Cell Metab 3 (2006) 167-175
15. Fu J., Gaetani S., Oveisi F., LoVerme J., Serrano A., Rodriguez de Fonseca F., et al. Oleoylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPARα. Nature 425 (2003) 90-93
16. O'Sullivan S.E. Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors. Br J Pharmacol 152 (2007) 576-582
17. Artmann A., Petersen G., Hellgren L.I., Boberg J., Skonberg C., Hansen S.H., et al. Influence of dietary fatty acids on endocannbinoid and n-acylethanolamine levels in rat brain, liver and small intestine. Biochim Biophys Acta Mol Cell Biol Lipids 1781 (2008) 200-212
18. Ahn K., McKinney M.K., and Cravatt B.F. Enzymatic pathways that regulate endocannabinoid signaling in the nervous system. Chem Rev 108 (2008) 1687-1707
19. Kurahashi Y., Ueda N., Suzuki H., Suzuki M., and Yamamoto S. Reversible hydrolysis and synthesis of anandamide demonstrated by recombinant rat fatty-acid amide hydrolase. Biochem Biophys Res Commun 237 (1997) 512-515
20. Kopka J., Ohlrogge J.B., and Jaworski J.G. Analysis of in vivo levels of acyl-thioesters with gas chromatography/mass spectrometry of the butylamide derivative. Anal Biochem 224 (1995) 51-60
21. Deutsch J., Rapoport S.I., and Purdon A.D. Relation between free fatty acid and acyl-CoA concentrations in rat brain following decapitation. Neurochem Res 22 (1997) 759-765
22. Bazinet R.P., Lee H.J., Felder C.C., Porter A.C., Rapoport S.I., and Rosenberger T.A. Rapid high-energy microwave fixation is required to determine the anandamide (N-arachidonoylethanolamine) concentration of rat brain. Neurochem Res 30 (2006) 597-601
23. Hansen H.S., Moesgaard B., Hansen H.H., and Petersen G. N-Acylethanolamines and precursor phospholipids-relation to cell injury. Chem Phys Lipids 108 (2000) 135-150
24. Cadas H., di Tomaso E., and Piomelli D. Occurrence and biosynthesis of endogenous cannabinoid precursor, N-arachidonoyl phosphatidylethanolamine, in rat brain. J Neurosci 17 (1997) 1226-1242
25. 31P NMR and enzyme activity study. J Lipid Res 41 (2000) 985-990
26. Schmid H.H.O., and Berdyshev E.V. Cannabinoid receptor-inactive N-acylethanolamines and other fatty acid amides: metabolism and function. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 363-376
27. Sugiura T., Kobayashi Y., Oka S., and Waku K. Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological significance. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 173-192
28. 2+-independent phosphatidylethanolamine N-acyltransferase generating the anandamide precursor and its congeners. J Biol Chem 282 (2007) 3614-3623
29. 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
30. Wang J., Okamoto Y., Tsuboi K., and Ueda N. The stimulatory effect of phosphatidylethanolamine on N-acylphosphatidylethanolamine-hydrolyzing phospholipase D (NAPE-PLD). Neuropharmacology 54 (2008) 8-15
31. Wang J., Okamoto Y., Morishita J., Tsuboi K., Miyatake A., and Ueda N. Functional analysis of the purified anandamide-generating phospholipase D as a member of the metallo-β-lactamase family. J Biol Chem 281 (2006) 12325-12335
32. Petersen G., and Hansen H.S. N-Acylphosphatidylethanolamine-hydrolysing phospholipase D lacks the ability to transphosphatidylate. FEBS Lett 455 (1999) 41-44
33. Fu J., Astarita G., Gaetani S., Kim J., Cravatt B.F., Mackie K., et al. Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine. J Biol Chem 282 (2007) 1518-1528
34. Morishita J., Okamoto Y., Tsuboi K., Ueno M., Sakamoto H., Maekawa N., et al. Regional distribution and age-dependent expression of N-acylphosphatidylethanolamine-hydrolyzing phospholipase D in rat brain. J Neurochem 94 (2005) 753-762
35. Moesgaard B., Petersen G., Mortensen S.A., and 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 131 (2002) 475-482
36. Egertova M., Simon G.M., Cravatt B.F., and 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 506 (2008) 604-615
37. Suarez J., Bermudez-Silva F.J., Mackie K., Ledent C., Zimmer A., Cravatt B.F., et al. Immunohistochemical description of the endogenous cannabinoid system in the rat cerebellum and functionally related nuclei. J Comp Neurol 509 (2008) 400-421
38. Leung D., Saghatelian A., Simon G.M., and Cravatt B.F. Inactivation of N-acyl phosphatidylethanolamine phospholipase D reveals multiple mechanisms for the biosynthesis of endocannabinoids. Biochemistry 45 (2006) 4720-4726
39. Fu J., Kim J., Oveisi F., Astarita G., and Piomelli D. Targeted enhancement of oleoylethanolamide production in proximal small intestine induces across-meal satiety in rats. Am J Physiol Regul Integr Comp Physiol 295 (2008) R45-R50
40. 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
41. 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
42. Nagan N., and Zoeller R.A. Plasmalogens: biosynthesis and functions. Prog Lipid Res 40 (2001) 199-229
43. Astarita G., Ahmed F., and Piomelli D. Identification of biosynthetic precursors for the endocannabinoid anandamide in the rat brain. J Lipid Res 49 (2008) 48-57
44. 2 and lysophospholipase D. Biochem J 380 (2004) 749-756
45. Liu J., Wang L., Harvey-White J., Osei-Hyiaman D., Razdan R., Gong Q., et al. A biosynthetic pathway for anandamide. Proc Natl Acad Sci U S A 103 (2006) 13345-13350
46. Liu J., Wang L., Harvey-White J., Huang B.X., Kim H.Y., Luquet S., et al. Multiple pathways involved in the biosynthesis of anandamide. Neuropharmacology 54 (2008) 1-7
47. Van Overloop H., Gijsbers S., and van Veldhoven P.P. Further characterization of mammalian ceramide kinase: substrate delivery and (stereo)specificity, tissue distribution, and subcellular localization studies. J Lipid Res 47 (2006) 268-283
48. Hansen H.S., Lauritzen L., Strand A.M., Vinggaard A.M., Frandsen A., and Schousboe A. Characterization of glutamate-induced formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cultured neocortical neurons. J Neurochem 69 (1997) 753-761
49. 31P NMR study. J Lipid Res 40 (1999) 515-521
50. Natarajan V., Schmid P.C., and Schmid H.H.O. N-acylethanolamine phospholipid metabolism in normal and ischemic rat brain. Biochim Biophys Acta 878 (1986) 32-41
51. Hansen H.S., Moesgaard B., Petersen G., and Hansen H.H. Putative neuroprotective actions of N-acyl-ethanolamines. Pharmacol Ther 95 (2002) 119-126
52. Hansen H.H., Schmid P.C., Bittigau P., Lastres-Becker I., Berrendero F., Manzanares J., et al. Anandamide, but not 2-arachidonoylglycerol, accumulates during in vivo neurodegeneration. J Neurochem 78 (2001) 1415-1427
53. Patel S., Carrier E.J., Ho W.S.V., Rademacher D.J., Cunningham S., Reddy D.S., et al. The postmortal accumulation of brain N-arachidonylethanolamine (anandamide) is dependent upon fatty acid amide hydrolase activity. J Lipid Res 46 (2005) 342-349
54. Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., and Gilula N.B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 384 (1996) 83-87
55. 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
56. Tsuboi K., Takezaki N., and Ueda N. The N-acylethanolamine-hydrolyzing acid amidase (NAAA). Chem Biodivers 4 (2007) 1914-1925
57. Cravatt B.F., Demarest K., Patricelli M.P., Bracey M.H., Giang D.K., Martin B.R., 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
58. Vandevoorde S. Overview of the chemical families of fatty acid amide hydrolase and monoacylglycerol lipase inhibitors. Curr Top Med Chem 8 (2008) 247-267
59. Tsuboi K., Zhao L.Y., Okamoto Y., Araki N., Ueno M., Sakamoto H., et al. Predominant expression of lysosomal N-acylethanolamine-hydrolyzing acid amidase in macrophages revealed by immunochemical studies. Biochim Biophys Acta 1771 (2007) 623-632
60. Sun Y.X., Tsuboi K., Zhao L.Y., Okamoto Y., Lambert D.M., and Ueda N. Involvement of N-acylethanolamine-hydrolyzing acid amidase in the degradation of anandamide and other N-acylethanolamines in macrophages. Biochim Biophys Acta Mol Cell Biol Lipids 1736 (2005) 211-220
61. Tsuboi K., Hilligsmann C., Vandevoorde S., Lambert D.M., and Ueda N. N-cyclohexanecarbonylpentadecylamine: a selective inhibitor of the acid amidase hydrolysing N-acylethanolamines, as a tool to distinguish acid amidase from fatty acid amide hydrolase. Biochem J 379 (2004) 99-106
62. Fegley D., Gaetani S., Duranti A., Tonini A., Mor M., Tarzia G., et al. Characterization of the fatty acid amide hydrolase inhibitor cyclohexyl carbamic acid 3′-carbamoyl-biphenyl-3-yl ester (URB597): effects on anandamide and oleoylethanolamide deactivation. J Pharmacol Exp Ther 313 (2005) 352-358
63. Rouzer C.A., and Marnett L.J. Non-redundant functions of cyclooxygenases: oxygenation of endocannabinoids. J Biol Chem 283 (2008) 8065-8069
64. Stark K., Dostalek M., and Guengerich F.P. Expression and purification of orphan cytochrome P450 4X1 and oxidation of anandamide. FEBS J 275 (2008) 3706-3717
65. Weber A., Ni J.S., Ling K.H.J., Acheampong A., Tang-Liu D.D.S., Burk R., et al. Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry. J Lipid Res 45 (2004) 757-763
66. Degn M., Lambertsen K.L., Petersen G., Meldgaard M., Artmann A., Clausen B.H., et al. Changes in brain levels of N-acylethanolamines and 2-arachidonoylglycerol in focal cerebral ischemia in mice. J Neurochem 103 (2007) 1907-1916
67. Di Marzo V., and Petrosino S. Endocannabinoids and the regulation of their levels in health and disease. Curr Opin Lipidol 18 (2007) 129-140
68. Hansen H.S., Petersen G., Artmann A., and Madsen A.N. Endocannabinoids. Eur J Lipid Sci Technol 108 (2006) 877-889
69. Matias I., Carta G., Murru E., Petrosino S., Banni S., and Di Marzo V. Effect of polyunsaturated fatty acids on endocannabinoid and N-acyl-ethanolamine levels in mouse adipocytes. Biochim Biophys Acta 1781 (2008) 52-60
70. Perez-Palacios T., Antequera T., Muriel E., Martin D., and Ruiz J. Stereospecific analysis of phospholipid classes in skeletal muscle from rats fed different fat sources. J Agric Food Chem 55 (2007) 6191-6197
71. Di Marzo V., Goparaju S.K., Wang L., Liu J., Bátkai S., Járai Z., et al. Leptin-regulated endocannabinoids are involved in maintaining food intake. Nature 410 (2001) 822-825
72. Petersen G., Sorensen C., Schmid P.C., Artmann A., Tang-Christensen M., Hansen S.H., et al. Intestinal levels of anandamide and oleoylethanolamide in food-deprived rats are regulated through their precursors. Biochim Biophys Acta Mol Cell Biol Lipids 1761 (2006) 143-150
73. Gómez R., Navarro M., Ferrer B., Trigo J.M., Bilbao A., Del Arco I., et al. A peripheral mechanism for CB1 cannabinoid receptor-dependent modulation of feeding. J Neurosci 22 (2002) 9612-9617
74. Thorens B., and Larsen P.J. Gut-derived signaling molecules and vagal afferents in the control of glucose and energy homestasis. Curr. Opin. Clin. Nutr. Metab. Care 7 (2004) 471-478
75. Gaetani S., Oveisi F., and Piomelli D. Modulation of meal pattern in the rat by anorexic lipid mediator oleoylethanolamide. Neuropsychopharmacology 28 (2003) 1311-1316
76. Capasso R., and Izzo A.A. Gastrointestinal regulation of food intake: general aspects and focus on anandamide and oleoylethanolamide. J Neuroendocrinol 20 Suppl. 1 (2008) 39-46
77. Colombo G., Agabio R., Diaz G., Lobina C., Reali R., and Gessa G.L. Appetite suppression and weight loss after the cannabinoid antagonist SR141716. Life Sci 63 (1998) L113-L117
78. Cota D., Marsicano G., Tschöp M., Grübler Y., Flachskamm C., Schubert M., et al. The endogenous cannabinoid system affects energy balance via central orexigenic drive and peripheral lipogenesis. J Clin Invest 112 (2003) 423-431
79. Van Gaal L.F., Rissanen A.M., Scheen A.J., Ziegler O., Rössner S., and RIO-Europe S.G. Effects of the cannabinoid-1 receptor blocker rimonabant on weight reduction and cardiovascular risk factors in overweight patients: 1-year experience from the RIO-Europe study. Lancet 365 (2005) 1389-1397
80. Howlett A.C., Barth F., Bonner T.I., Cabral G., Casellas P., Devane W.A., et al. International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol. Rev. 54 (2002) 161-202
81. Lichtman A.H., Leung D., Shelton C.C., Saghatelian A., Hardouin C., Boger D.L., et al. Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity. J Pharmacol Exp Ther 311 (2004) 441-448
82. Long J.Z., Li W., Booker L., Burston J.J., Kinsey S.G., Schlosburg J.E., et al. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol 5 (2009) 37-44
83. Berger A., Crozier G., Bisogno T., Cavaliere P., Innis S., and Di Marzo V. Anandamide and diet: inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N-acylethanolamines in piglets. Proc Natl Acad Sci U S A 98 (2001) 6402-6406
84. Burdyga G., Lal S., Varro A., Dimaline R., Thompson D.G., and Dockray G.J. Expression of cannabinoid CB1 receptors by vagal afferent neurons is inhibited by cholecystokinin. J Neurosci 24 (2004) 2708-2715
85. Pavon F.J., Serrano A., Perez-Valero V., Jagerovic N., Hernandez-Folgado L., Bermudez-Silva F.J., et al. Central versus peripheral antagonism of cannabinoid CB1 receptor in obesity: effects of LH-21, a peripherally acting neutral cannabinoid receptor antagonist, in Zucker rats. J Neuroendocrinol 20 Suppl. 1 (2008) 116-123
86. Chen R.Z., Frassetto A., Lao J.Z., Huang R.R., Xiao J.C., Clements M.J., et al. Pharmacological evaluation of LH-21, a newly discovered molecule that binds to cannabinoid CB1 receptor. Eur J Pharmacol 584 (2008) 338-342
87. Madsen A.N., Jelsing J., van de Wall E.H., Vrang N., Larsen P.J., and Schwartz G.J. Rimonabant induced anorexia in rodents is not mediated by vagal or sympathetic gut afferents. Neurosci Lett 449 (2009) 20-23
88. Zygmunt P.M., Petersson J., Andersson D.A., Chuang H.H., Sorgård M., Di Marzo V., et al. Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 400 (1999) 452-457
89. Movahed P., Jönsson B.A.G., Birnir B., Wingstrand J.A., Jorgensen T.D., Ermund A., et al. Endogenous unsaturated C18N-acylethanolamines are vanilloid receptor (TRPV1) agonists. J Biol Chem 280 (2005) 38496-38504
90. Ahern G.P. Activation of TRPV1 by the satiety factor oleoylethanolamide. J Biol Chem 278 (2003) 30429-30434
91. Motter A.L., and Ahern G.P. TRPV1-null mice are protected from diet-induced obesity. FEBS Lett 582 (2008) 2257-2262
92. Lo Verme J., Gaetani S., Fu J., Oveisi F., Burton K., and Piomelli D. Regulation of food intake by oleoylethanolamide. Cell Mol Life Sci 62 (2005) 708-716
93. Fredriksson R., Hoglund P.J., Gloriam D.E., Lagerstrom M.C., and Schioth H.B. Seven evolutionarily conserved human rhodopsin G protein-coupled receptors lacking close relatives. FEBS Lett 554 (2003) 381-388
94. Soga T., Ohishi T., Matsui T., Saito T., Matsumoto M., Takasaki J., et al. Lysophosphatidylcholine enhances glucose-dependent insulin secretion via an orphan G-protein-coupled receptor. Biochem Biophys Res Commun 326 (2005) 744-751
95. Chu Z.L., Jones R.M., He H., Carroll C., Gutierrez V., Lucman A., et al. A role for beta-cell-expressed G protein-coupled receptor 119 in glycemic control by enhancing glucose-dependent insulin release. Endocrinology 148 (2007) 2601-2609
96. Bonini JA. Methods of identifying compounds that binds to SNORF25 receptors. US Patent 6,468,756; 2002.
97. Chu Z.L., Carroll C., Alfonso J., Gutierrez V., He H., Lucman A., et al. A role for intestinal endocrine cell-expressed g protein-coupled receptor 119 in glycemic control by enhancing glucagon-like Peptide-1 and glucose-dependent insulinotropic Peptide release. Endocrinology 149 (2008) 2038-2047
98. Sakamoto Y., Inoue H., Kawakami S., Miyawaki K., Miyamoto T., Mizuta K., et al. Expression and distribution of Gpr119 in the pancreatic islets of mice and rats: predominant localization in pancreatic polypeptide-secreting PP-cells. Biochem Biophys Res Commun 351 (2006) 474-480
99. Kojima S., Ueno N., Asakawa A., Sagiyama K., Naruo T., Mizuno S., et al. A role for pancreatic polypeptide in feeding and body weight regulation. Peptides 28 (2007) 459-463
100. Semple G., Fioravanti B., Pereira G., Calderon I., Uy J., Choi K., et al. Discovery of the first potent and orally efficacious agonist of the orphan G-protein coupled receptor 119. J Med Chem 51 (2008) 5172-5175
101. Williams D.L., Baskin D.G., and Schwartz M.W. Evidence that intestinal GLP-1 plays a physiological role in satiety. Endocrinology 150 (2009) 1680-1687
102. Proulx K., Cota D., Castañeda T.R., Tshöp M.H., D'Alessio D.A., Tso P., et al. Mechanisms of oleoylethanolamide-induced changes in feeding behaviour and motor activity. Am J Physiol Regul Integr Comp Physiol 289 (2005) 729-737
103. Fu J., Oveisi F., Gaetani S., Lin E., and Piomelli D. Oleoylethanolamide, an endogenous PPAR-α agonist, lowers body weight and hyperlipidemia in obese rats. Neuropharmacology 48 (2005) 1147-1153
104. Sun Y., Alexander S.P., Garle M.J., Gibson C.L., Hewitt K., Murphy S.P., et al. Cannabinoid activation of PPARalpha; a novel neuroprotective mechanism. Br J Pharmacol 152 (2007) 734-743
105. Nagasawa M., Ide T., Suzuki M., Tsunoda M., Akasaka Y., Okazaki T., et al. Pharmacological characterization of a human-specific peroxisome proliferater-activated receptor α (PPARα) agonist in dogs. Biochem Pharmacol 67 (2004) 2057-2069
106. Stricker-Krongrad A., Beck B., and Burlet C. Nitric oxide mediates hyperphagia of obese Zucker rats: relation to specific changes in the microstructure of feeding behavior. Life Sci 58 (1996) L9-L15
107. Thabuis C., Tissot-Favre D., Bezelgues J.B., Martin J.C., Cruz-Hernandez C., Dionisi F., et al. Biological functions and metabolism of oleoylethanolamide. Lipids 43 (2008) 887-888
108. Guzmán M., Lo Verme J., Fu J., Oveisi F., Blázquez C., and Piomelli D. Oleoylethanolamide stimulates lipolysis by activating the nuclear receptor peroxisome proliferator-activated receptor α (PPAR-α). J Biol Chem 279 (2004) 27849-27854
109. Melis M., Pillolla G., Luchicchi A., Muntoni A.L., Yasar S., Goldberg S.R., et al. Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic dopamine neurons through nuclear receptors. J Neurosci 28 (2008) 13985-13994
110. Furlong S.J., Ridgway N.D., and Hoskin D.W. Modulation of ceramide metabolism in T-leukemia cell lines potentiates apoptosis induced by the cationic antimicrobial peptide bovine lactoferricin. Int J Oncol 32 (2008) 537-544
111. Chavez J.A., Knotts T.A., Wang L.P., Li G.B., Dobrowsky R.T., Florant G.L., et al. A role for ceramide, but not diacylglycerol, in the antagonism of insulin signal transduction by saturated fatty acids. J Biol Chem 278 (2003) 10297-10303
112. Chmura S.J., Nodzenski E., Kharbanda S., Pandey P., Quintáns J., Kufe D.W., et al. Down-regulation of ceramide production abrogates ionizing radiation-induced cytochrome c release and apoptosis. Mol Pharmacol 57 (2000) 792-796
113. Hansen H.S., and Artmann A. Endocannabinoids and nutrition. J Neuroendocrinol 20 Suppl. 1 (2008) 94-99
114. Osei-Hyiaman D., DePetrillo M., Pacher P., Liu J., Radaeva S., Bátkai S., et al. Endocannabinoid activation at hepatic CB1 receptors stimulates fatty acid synthesis and contributes to diet-induced obesity. J Clin Invest 115 (2005) 1298-1305
115. Kim D.Y., and Rho J.M. The ketogenic diet and epilepsy. Curr Opin Clin Nutr Metab Care 11 (2008) 113-120
116. Hansen S.L., Nielsen A.H., Knudsen K.E., Artmann A., Petersen G., Kristiansen U., et al. Ketogenic diet is antiepileptogenic in pentylenetetrazole kindled mice and decrease levels of N-acylethanolamines in hippocampus. Neurochem Int 54 (2009) 199-204
117. González S., Valenti M., De Miguel R., Fezza F., Fernández-Ruiz J., Di Marzo V., et al. Changes in endocannabinoid contents in reward-related brain regions of alcohol-exposed rats, and their possible relevance to alcohol relapse. Br J Pharmacol 143 (2004) 455-464
118. Ferrer B., Bermudez-Silva F.J., Bilbao A., Alvarez-Jaimes L., Sanchez-Vera I., Giuffrida A., et al. Regulation of brain anandamide by acute administration of ethanol. Biochem J 404 (2007) 97-104
119. Rodriguez de Fonseca F., Gorriti M.A., Bilbao A., Escuredo L., García-Segura L.M., Piomelli D., et al. Role of the endogenous cannabinoid system as a modulator of dopamine transmission: Implications for Parkinsońs disease and schizophrenia. Neurotoxicity Res 3 (2001) 25-35
120. Diep T.A., Hansen S.H., Kristiansen M.M., and Hansen H.S. Effect of high fat diet on intestinal formation of acylethanolamides. Keystone Symp: Obesity: Novel Aspects Regul Body Weight (2009) p. 186 [abstract]
121. Schwartz G.J., Fu J., Astarita G., Li X., Gaetani S., Campolongo P., et al. The lipid messenger OEA links dietary fat intake to satiety. Cell Metab 8 (2008) 281-288
122. Woltman T., and Reidelberger R. Effects of duodenal and distal ileal infusions of glucose and oleic acid on meal patterns in rats. Am J Physiol 269 (1995) R7-R14