PUFA-derived endocannabinoids: An overview

Proceedings of the Nutrition Society

Volumn 72, Issue 4, 2013, Pages 451-459

  Cascio, Maria Grazia ^a  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

Author keywords

2 arachidonoyl glycerol; Anandamide; Cannabinoid receptors; Food intake; Obesity

Indexed keywords

CANNABINOID; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; ENDOCANNABINOID; FATTY ACID AMIDASE; POLYUNSATURATED FATTY ACID; 2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; ARACHIDONATE 15 LIPOXYGENASE; CANNABINOID RECEPTOR; CYCLOOXYGENASE 2; CYTOCHROME P450; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; CYTOCHROME P450 ISOENZYME; DIACYLGLYCEROL; DOCOSAHEXAENOIC ACID; HIGH DENSITY LIPOPROTEIN CHOLESTEROL; HYDROLASE; ICOSAPENTAENOIC ACID; NON RECEPTOR PROTEIN TYROSINE PHOSPHATASE 22; OMEGA 3 FATTY ACID; OMEGA 6 FATTY ACID; PHOSPHATIDYLETHANOLAMINE; PHOSPHOLIPASE A2; PHOSPHOLIPASE C; PHOSPHOLIPASE D; PROTEIN TYROSINE PHOSPHATASE;

BIOSYNTHESIS; CONFERENCE PAPER; DEGRADATION; ENERGY EXPENDITURE; FOOD INTAKE; GABAERGIC TRANSMISSION; HUMAN; HYDROLYSIS; INTRACELLULAR SPACE; METABOLISM; NERVE CELL PLASTICITY; NONHUMAN; OBESITY; OXIDATION; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; CALORIC INTAKE; ENZYMATIC DEGRADATION; EXTRACELLULAR SPACE; FATTY ACID OXIDATION; FATTY ACID SYNTHESIS; FATTY ACID TRANSPORT; LIPID DEGRADATION; LIPID HYDROLYSIS; LONG TERM DEPRESSION; LONG TERM POTENTIATION; NERVE CELL; NERVOUS SYSTEM DEVELOPMENT; PHYSIOLOGICAL PROCESS; SYNAPTIC TRANSMISSION; THERAPY EFFECT; UPREGULATION; WILD TYPE;

ENDOCANNABINOIDS; FATTY ACIDS, UNSATURATED; HUMANS; NEURONS; RECEPTORS, CANNABINOID;

EID: 84893042135     PISSN: 00296651     EISSN: 14752719     Source Type: Journal    
DOI: 10.1017/S0029665113003418     Document Type: Conference Paper

References (107)

1. Di Marzo V, Bifulco M & De Petrocellis L (2004) The endocannabinoid system and its therapeutic exploitation. Nat Rev Drug Discov 3, 771-784.
2. Devane WA, Hanus L, Breuer A, et al. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949.
3. Hanus LO (2007) Discovery and isolation of anandamide and other endocannabinoids. Chem Biodivers 4, 1828-1841.
4. Di Marzo V, Bisogno T & De Petrocellis L (2001) Anandamide: Some like it hot. Trends Pharmacol Sci 22, 346-349.
5. Smart D, Gunthorpe MJ, Jerman JC, et al. (2000) The endogenous lipid anandamide is a full agonist at the human vanilloid receptor (hVR1). Br J Pharmacol 129, 227-230.
6. Al-Hayani A, Wease KN, Ross RA, et al. (2001) The endogenous cannabinoid anandamide activates vanilloid receptors in the rat hippocampal slice. Neuropharmacology 41, 1000-1005.
7. Mechoulam R, Ben-Shabat S, Hanus L, et al. (1995) Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol 50, 83-90.
8. Sugiura T, Kondo S, Sukagawa A, et al. (1995 -Arachidonoylglycerol: A possible endogenous cannabinoid receptor ligand in brain. Biochem Biophys Res Commun 215, 89-97.
9. Sigel E, Baur R, Rácz I, et al. (2011) The major central endocannabinoid directly acts at GABA(A) receptors. Proc Natl Acad Sci USA 108, 18150-18155.
10. Hanus L, Abu-LafiS, Fride E, et al. (2001) 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc Natl Acad Sci USA 98, 3662-3665.
11. Porter AC, Sauer J-M, Knierman MD, et al. (2002) Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J Pharmacol Exp Ther 301, 1020-1024.
12. De Petrocellis L, Cascio MG & Di Marzo V (2004) The endocannabinoid system: A general view and latest additions. Br J Pharmacol 141, 765-774.
13. De Petrocellis L, Starowicz K, Moriello AS, et al. (2007) Regulation of transient receptor potential channels of melastatin type 8 (TRPM8): Effect of cAMP, cannabinoid CB1 receptors and endovanilloids. Exp Cell Res 313, 1911-1920.
14. Pertwee RG (2005) The therapeutic potential of drugs that target cannabinoid receptors or modulate the tissue levels or actions of endocannabinoids. AAPS J 7, E625-E654.
15. Brown I, Cascio MG, Wahle KWJ, et al. (2010) Cannabinoid receptor-dependent and -independent antiproliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis 31, 1584-1591.
16. Bisogno T, Delton Vandenbroucke I, Milone A, et al. (1999) Biosynthesis and inactivation of N-Arachidonoylethanolamine (anandamide) and N-docosahexaenoylethanolamine in bovine retina. Arch Biochem Biophys 370, 300-307.
17. Sugiura T, Kondo S, Sukagawa A, et al. (1996) N-Arachidonoylethanolamine (anandamide), an endogenous cannabinoid receptor ligand, and related lipid molecules in the nervous tissues. J Lipid Mediat Cell Signal 14, 51-56.
18. Berger A, Crozier G, Bisogno T, et al. (2001) Anandamide and diet: Inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N-Acylethanolamines in piglets (vol 98, pg 6402, 2001). Proc Natl Acad Sci USA 98, 7647-7647.
19. Maccarrone M, Gasperi V, Catani MV, et al. (2010b) The endocannabinoid system and its relevance for nutrition. Annu Rev Nutr 30, 423-440.
20. Brown I, Wahle KWJ, Cascio MG, et al. (2011) Omega-3 N-Acylethanolamines are endogenously synthesised from omega-3 fatty acids in different human prostate and breast cancer cell lines. Prostaglandins Leukot Essent Fatty Acids 85, 305-310.
21. Brown I, Cascio MG, Rotondo D, et al. (2013) Cannabinoids and omega-3/6 endocannabinoids as cell death and anticancer modulators. Progr Lipid Res 52, 80-109.
22. Mechoulam R, Fride E & Di Marzo V (1998) Endocannabinoids. Eur J Pharmacol 359, 1-18.
23. Ben-Shabat S, Fride E, Sheskin T, et al. (1998) An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-Arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 353, 23-31.
24. Devane WA, Dysarz FA, Johnson MR, et al. (1988) Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol 34, 605-613.
25. Matsuda LA, Lolait SJ, Brownstein MJ, et al. (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346, 561-564.
26. Munro S, Thomas KL & Abu-Shaar M (1993) Molecular characterization of a peripheral receptor for cannabinoids. Nature 365, 61-65.
27. Pertwee RG (2006b) The pharmacology of cannabinoid receptors and their ligands: An overview. Int J Obes 30, S13-S18.
28. Derkinderen P, Ledent C, Parmentier M, et al. (2001) Cannabinoids activate p38 mitogen-Activated protein kinases through CB1 receptors in hippocampus. J Neurochem 77, 957-960.
29. Gertsch J, Schoop R, Kuenzle U, et al. (2004) Echinacea alkylamides modulate TNF-Alpha gene expression via cannabinoid receptor CB2 and multiple signal transduction pathways. FEBS Lett 577, 563-569.
30. Howlett AC, Barth F, Bonner TI, et al. (2002) International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol Rev 54, 161-202.
31. Pertwee RG & Ross RA (2002) Cannabinoid receptors and their ligands. Prostaglandins Leukot Essent Fatty Acids 66, 101-121.
32. Pertwee R (2008) The therapeutic potential of drugs that target the endogenous cannabinoid system. Eur Neuropsychopharmacol 18, S170-S171.
33. Battista N, Di Tommaso M, Bari M, et al. (2012) The endocannabinoid system: An overview. Front Behav Neurosci. 6, 1-7.
34. Price MR, Baillie GL, Thomas A, et al. (2005) Allosteric modulation of the cannabinoid CB1 receptor. Mol Pharmacol 68, 1484-1495.
35. Onaivi ES, Ishiguro H, Gong JP, et al. (2006) Discovery of the presence and functional expression of cannabinoid CB2 receptors in brain. Ann N Y Acad Sci 1074, 514-536.
36. Viscomi MT, Oddi S, Latini L, et al. (2009) Selective CB2 receptor agonism protects central neurons from remote axotomy-induced apoptosis through the PI3K/Akt pathway. J Neurosci 29, 4564-4570.
37. Gasperi V, Dainese E, Oddi S, et al. (2013) GPR55 and its interaction with membrane lipids: Comparison with other endocannabinoid-binding receptors. Curr Med Chem 20, 64-78.
38. Schmid HHO, Schmid PC & Natarajan V (1996) The N-Acylation- phosphodiesterase pathway and cell signalling. Chem Phys Lipids 80, 133-142.
39. Schmid HHO & Berdyshev EV (2002) Cannabinoid receptor-inactive N-Acylethanolamines and other fatty acid amides: Metabolism and function. Prostaglandins Leukot Essent Fatty Acids 66, 363-376.
40. Hansen HS, Lauritzen L, Moesgaard B, et al. (1998) Formation of N-Acyl-phosphatidylethanolamines and N-Acylethanolamines-proposed role in neurotoxicity. Biochem Pharmacol 55, 719-725.
41. Sun YX, Tsuboi K, Okamoto Y, et al. (2004) Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A2 and lysophospholipase D. Biochem J 380, 749-756.
42. Simon GM & Cravatt BF (2006) Endocannabinoid biosynthesis proceeding through glycerophospho-N-Acyl ethanolamine and a role for alpha/beta-hydrolase 4 in this pathway. J Biol Chem 281, 26465-26472.
43. Liu J, Wang L, Harvey-White J, et al. (2006) A biosynthetic pathway for anandamide. Proc Natl Acad Sci USA 103, 13345-13350.
44. Deutsch DG & Chin SA (1993) Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem Pharmacol 46, 791-796.
45. Devane WA & Axelrod J (1994) Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain membranes. Proc Natl Acad Sci USA 91, 6698-6701.
46. Ueda N, Kurahashi Y, Yamamoto S, et al. (1995) Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J Biol Chem 270, 23823-23827.
47. Katayama K, Ueda N, Katoh I, et al. (1999) Equilibrium in the hydrolysis and synthesis of cannabimimetic anandamide demonstrated by a purified enzyme. Biochim Biophys Acta 1440, 205-214.
48. Ueda N, Tsuboi K & Uyama T (2010) Enzymological studies on the biosynthesis of N-Acylethanolamines. Biochim Biophys Acta 1801, 1274-1285.
49. Bisogno T, Howell F, Williams G, et al. (2003) Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain. J Cell Biol 163, 463-468.
50. Williams EJ, Walsh FS & Doherty P (2003) The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response. J Cell Biol 160, 481-486.
51. Tanimura A, Yamazaki M & Hashimotodani Y, et al. (2010) The endocannabinoid 2-Arachidonoylglycerol produced by diacylglycerol lipase alpha mediates retrograde suppression of synaptic transmission. Neuron 65, 320-327.
52. Gao Y, Vasilyev DV, Goncalves MB, et al. (2010) Loss of retrograde endocannabinoid signaling and reduced adult neurogenesis in diacylglycerol lipase knock-out mice. J Neurosci 30, 2017-2024.
53. Savinainen JR, Saario SM & Laitinen JT (2012) The serine hydrolases MAGL, ABHD6 and ABHD12 as guardians of 2-Arachidonoylglycerol signalling through cannabinoid receptors. Acta Physiol 204, 267-276.
54. Wilson RI & Nicoll RA (2002) Neuroscience-endocannabinoid signaling in the brain. Science 296, 678-682.
55. Diana MA & Marty A (2004) Endocannabinoid-mediated short-Term synaptic plasticity: Depolarization-induced suppression of inhibition (DSI) and depolarizationinduced suppression of excitation (DSE). Br J Pharmacol 142, 9-19.
56. Wilson RI & Nicoll RA (2001) Endogenous cannabinoids mediate retrograde signalling at hippocampal synapses. Nature 410, 588-592.
57. Wilson RI, Kunos G & Nicoll RA (2001) Presynaptic specificity of endocannabinoid signaling in the hippocampus. Neuron 31, 453-462.
58. Diana MA, Levenes C, Mackie K, et al. (2002) Short-Term retrograde inhibition of GABAergic synaptic currents in rat Purkinje cells is mediated by endogenous cannabinoids. J Neurosci 22, 200-208.
59. Rodríguez de Fonseca F, Del Arco I, Bermudez-Silva FJ, et al. (2005) The endocannabinoid system: Physiology and pharmacology. Alcohol Alcohol 40, 2-14.
60. Fowler CJ (2012) Anandamide uptake explained? Trends Pharmacol Sci 33, 181-185.
61. Giang DK & Cravatt BF (1997) Molecular characterization of human and mouse fatty acid amide hydrolases. Proc Natl Acad Sci USA 94, 2238-2242.
62. Maurelli S, Bisogno T, De Petrocellis L, et al. (1995) Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase'. FEBS Lett 377, 82-86.
63. Saghatelian A, Trauger SA, Want EJ, et al. (2004) Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochem 43, 14332-14339.
64. Cravatt BF, Giang DK, Mayfield SP, et al. (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty-Acid amides. Nature 384, 83-87.
65. McKinney MK & Cravatt BF (2003) Evidence for distinct roles in catalysis for residues of the serine-serine-lysine catalytic triad of fatty acid amide hydrolase. J Biol Chem 278, 37393-37399.
66. Desarnaud F, Cadas H & Piomelli D (1995) Anandamide amidohydrolase activity in rat brain microsomes-identification and partial characterization. J Biol Chem 270, 6030-6035.
67. Katayama K, Ueda N, Kurahashi Y, et al. (1997) Distribution of anandamide amidohydrolase in rat tissues with special reference to small intestine. Biochim Biophys Acta 1347, 212-218.
68. Sun YX, Tsuboi KU, Zhao LY, et al. (2005) Involvement of N-Acylethanolamine-hydrolyzing acid amidase in the degradation of anandamide and other N-Acylethanolamines in macrophages. Biochim Biophys Acta 1736, 211-220.
69. Reilly SJ, O'Shea EM, Andersson U, et al. (2007) A peroxisomal acyltransferase in mouse identifies a novel pathway for taurine conjugation of fatty acids. FASEB J 21, 99-107.
70. Wei BQQ, Mikkelsen TS, McKinney MK, et al. (2006) A second fatty acid amide hydrolase with variable distribution among placental mammals. J Biol Chem 281, 36569-36578.
71. Ueda N, Yamanaka K, Terasawa Y, et al. (1999) An acid amidase hydrolyzing anandamide as an endogenous ligand for cannabinoid receptors. FEBS Lett 454, 267-270.
72. Ueda N, Yamanaka K & Yamamoto S (2001) Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance. J Biol Chem 276, 35552-35557.
73. Tsuboi K, Sun YX, Okamoto Y, et al. (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, 11082-11092.
74. Wang J, Zhao LY, Uyama T, et al. (2008) Amino acid residues crucial in pH regulation and proteolytic activation of N-Acylethanolamine-hydrolyzing acid amidase. Biochim Biophys Acta 1781, 710-717.
75. Blankman JL, Simon GM & Cravatt BF (2007) A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-Arachidonoylglycerol. Chem Biol 14, 1347-1356.
76. Goparaju SK, Ueda N, Taniguchi K, et al. (1999) Enzymes of porcine brain hydrolyzing 2-Arachidonoylglycerol, an endogenous ligand of cannabinoid receptors. Biochem Pharmacol 57, 417-423.
77. Labar G, Wouters J & Lambert DM (2010b) A review on the monoacylglycerol lipase: At the interface between fat and endocannabinoid signalling. Curr Med Chem 17, 2588-2607.
78. Bertrand T, Auge F, Houtmann J, et al. (2010) Structural basis for human monoglyceride lipase inhibition. J Mol Biol 396, 663-673.
79. Karlsson M, Contreras JA, Hellman U, et al. (1997) cDNA cloning, tissue distribution, and identification of the catalytic triad of monoglyceride lipase. Evolutionary relationship to esterases, lysophospholipases, and haloperoxidases. J Biol Chem 272, 27218-27223.
80. Labar G, Bauvois C, Borel F, et al. (2010a) Crystal structure of the human monoacylglycerol lipase, a key actor in endocannabinoid signaling. Chembiochem 11, 218-227.
81. Kano M, Ohno-Shosaku T, Hashimotodani Y, et al. (2009) Endocannabinoid-mediated control of synaptic transmission. Physiol Rev 89, 309-380.
82. Navia-Paldanius D, Savinainen JR & Laitinen JT (2012) Biochemical and pharmacological characterization of human alpha/beta-hydrolase domain containing 6 (ABHD6) and 12 (ABHD12). J Lipid Res 53, 2413-2424.
83. Marrs WR, Blankman JL, Horne EA, et al. (2010) The serine hydrolase ABHD6 controls the accumulation and efficacy of 2-AG at cannabinoid receptors. Nature Neurosci 13, 951-U67.
84. Fiskerstrand T, Brahim DHB, Johanssond S, et al. (2010) Mutations in ABHD12 cause the neurodegenerative disease PHARC: An inborn error of endocannabinoid metabolism. Am J Hum Genet 87, 410-417.
85. Yates ML & Barker EL (2009) Inactivation and biotransformation of the endogenous cannabinoids anandamide and 2-Arachidonoylglycerol. Mol Pharmacol 76, 11-17.
86. Piscitelli F & Di Marzo V (2012) 'Redundancy' of endocannabinoid inactivation: New challenges and opportunities for pain control. ACS Chem Neurosci 3, 356-363.
87. Yu M, Ives D & Ramesha CS (1997) Synthesis of prostaglandin E-2 ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 272, 21181-21186.
88. Di Marzo V (1998) 'Endocannabinoids' and other fatty acid derivatives with cannabimimetic properties: Biochemistry and possible physiopathological relevance. Biochim Biophys Acta 1392, 153-175.
89. Williams CM, Rogers PJ & Kirkham TC (1998) Hyperphagia in pre-fed rats following oral D9-THC. Physiol Behav 65, 343-346.
90. Williams CM & Kirkham TC (2002) Observational analysis of feeding induced by delta(9)-THC and anandamide. Physiol Behav 76, 241-250.
91. Gamage TF & Lichtman AH (2012) The endocannabinoid system: Role in energy regulation. Pediatr Blood Cancer 58, 144-148.
92. Matias I & Di Marzo V (2007) Endocannabinoids and the control of energy balance. Trends Endocrinol Metab 18, 27-37. Epub 2006 Dec 1. Review.
93. Li C, Jones PM & Persaud SJ (2011) Role of the endocannabinoid system in food intake, energy homeostasis and regulation of the endocrine pancreas. Pharmacol Ther 129, 307-320.
94. Salamone JD, McLaughlin PJ, Sink K, et al. (2007) Cannabinoid CB1 receptor inverse agonists and neutral antagonists: Effects on food intake, food-reinforced behavior and food aversions. Physiol Behav 91, 383-388.
95. Di Marzo V, Goparaju SK, Wang L, et al. (2001) Leptin-regulated endocannabinoids are involved in maintaining food intake. Nature 410, 822-825.
96. Wiley JL, Burston JJ, Leggett DC, et al. (2005) CB1 cannabinoid receptor-mediated modulation of food intake in mice. Br J Pharmacol 145, 293-300.
97. Cota D (2007) CB1 receptors: Emerging evidence for central and peripheral mechanisms that regulate energy balance, metabolism, and cardiovascular health. Diabetes Metab Res Rev 23, 507-517.
98. Ravinet Trillou C, Arnone M, Delgorge C, et al. (2003) Anti-obesity effect of SR141716, a CB1 receptor antagonist, in diet-induced obese mice. Am J Physiol Regul Integr Comp Physiol 284, R345-R353.
99. Vickers SP, Webster LJ, Wyatt A, et al. (2003) Preferential effects of the cannabinoid CB, receptor antagonist, SR 141716, on food intake and body weight gain of obese (fa/fa) compared to lean Zucker rats. Psychopharmacology 167, 103-111.
100. Ravinet Trillou C, Delgorge C, Menet C, et al. (2004) CB1 cannabinoid receptor knockout in mice leads to leanness, resistance to diet-induced obesity and enhanced leptin sensitivity. Int J Obes Relat Metab Disord 28, 640-648.
101. Osei-Hyiaman D, Harvey-White J, Batkai S, et al. (2006) The role of the endocannabinoid system in the control of energy homeostasis. Int J Obes 30, S33-S38.
102. Bensaid M, Gary-Bobo M, Esclangon A, et al. (2003) The cannabinoid CB1 receptor antagonist SR141716 increases Acrp30 mRNA expression in adipose tissue of obese fa/fa rats and in cultured adipocyte cells. Molecul Pharmacol 63, 908-914.
103. Matias I, Gonthier MP, Orlando P, et al. (2006) Regulation, function, and dysregulation of endocannabinoids in models of adipose and beta-pancreatic cells and in obesity and hyperglycemia. J Clin Endocrinol Metab 91, 3171-3180.
104. Fernandez JR & Allison DB (2004) Rimonabant Sanofi-Synthélabo. Curr Opin Investig Drugs 5, 430-435.
105. Silvestri C & Di Marzo V (2013) The endocannabinoid system in energy homeostasis and the etiopathology of metabolic disorders. Cell Metab 17, 475-490.
106. Bisogno T, Burston JJ, Rai R, et al. (2009) Synthesis and pharmacological activity of a potent inhibitor of the biosynthesis of the endocannabinoid 2-Arachidonoylglycerol. ChemMedChem 4, 946-950.
107. Naughton SS, Mathai ML, Hryciw DH, et al. (2013) Fatty acid modulation of the endocannabinoid system and the effect on food intake and metabolism. Int J Endocrinol 2013, 361895.