Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand

Progress in Lipid Research

Volumn 45, Issue 5, 2006, Pages 405-446

  Sugiura, Takayuki ^a   Kishimoto, Seishi ^a   Oka, Saori ^a   Gokoh, Maiko ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

2 Arachidonoylglycerol; Anandamide; Arachidonic acid; Cannabinoids; Lipid mediator; Monoacylglycerol

Indexed keywords

1 (2,4 DICHLOROPHENYL) 5 (4 IODOPHENYL) 4 METHYL N (1 PIPERIDYL) 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2,4 DICHLOROPHENYL) 5 (4 IODOPHENYL) 4 METHYL N MORPHOLINO 1H PYRAZOLE 3 CARBOXAMIDE; 1 DEOXY 3 (1,1 DIMETHYLBUTYL) DELTA8 TETRAHYDROCANNABINOL; 2 ARACHIDONOYLGLYCEROL; 2 ARACHIDONOYLGLYCEROL DERIVATIVE; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 3 (2 IODO 5 NITROBENZOYL) 1 (1 METHYL 2 PIPERIDINYLMETHYL)INDOLE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 4 [4 (1,1 DIMETHYLHEPTYL) 2,6 DIMETHOXYPHENYL] 6,6 DIMETHYLBICYCLO[3.1.1]HEPT 2 EN 2 YLMETHANOL; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; 6 IODO 3 (4 METHOXYBENZOYL) 2 METHYL 1 (2 MORPHOLINOETHYL)INDOLE; 7 NITROINDAZOLE; ANANDAMIDE; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR AGONIST; CANNABINOID RECEPTOR ANTAGONIST; CAPSAZEPINE; DEXANABINOL; DRONABINOL; GLYCEROL DERIVATIVE; JTE 907; N(G) METHYLARGININE; RIMONABANT; UNCLASSIFIED DRUG; VIRODHAMINE;

ALCOHOL METABOLISM; ANTICONVULSANT ACTIVITY; ANTIINFLAMMATORY ACTIVITY; BIOSYNTHESIS; BRAIN INJURY; BRAIN ISCHEMIA; BRAIN TISSUE; CANCER INVASION; CARCINOGENESIS; CARDIOVASCULAR SYSTEM; CELL TRANSFORMATION; CLINICAL TRIAL; DRUG DEPENDENCE; DRUG EFFECT; EATING DISORDER; EDEMA; ENZYME DEGRADATION; FOOD INTAKE; GASTROINTESTINAL TRACT; GENE CONTROL; HEAD INJURY; HUMAN; IMMUNE RESPONSE; IMMUNE SYSTEM; IMMUNOCOMPETENCE; INFLAMMATION; INFLAMMATORY CELL; LEUKOCYTE; LIPID METABOLISM; LONG TERM POTENTIATION; MEMBRANE TRANSPORT; NERVOUS SYSTEM; NEUROPROTECTION; NONHUMAN; OBESITY; OXYGENATION; PAIN; PRIORITY JOURNAL; RECEPTOR BINDING; RETROGRADE NERVE FIBER TRANSPORT; REVIEW; SEIZURE; SIGNAL TRANSDUCTION; STRESS; STRUCTURE ACTIVITY RELATION; SYNAPTIC TRANSMISSION; VASODILATATION; VOMITING;

ANIMALS; ARACHIDONIC ACIDS; BIOLOGICAL TRANSPORT; GLYCERIDES; HUMANS; IMMUNE SYSTEM; LIGANDS; MICE; NERVOUS SYSTEM PHYSIOLOGICAL PHENOMENA; NERVOUS SYSTEM PHYSIOLOGY; NEUROTRANSMITTER AGENTS; OXIDATION-REDUCTION; RATS; RECEPTORS, CANNABINOID; STRUCTURE-ACTIVITY RELATIONSHIP; SYNAPTIC TRANSMISSION;

EID: 33745195042     PISSN: 01637827     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.plipres.2006.03.003     Document Type: Review

References (354)

1. Gaoni Y., and Mechoulam R. Isolation, structure and partial synthesis of an active constituent of hashish. J Am Chem Soc 86 (1964) 1646-1647
2. Dewey W.L. Cannabinoid pharmacology. Pharmacol Rev 38 (1986) 151-178
3. Devane W.A., Dysarz III F.A., Johnson M.R., Melvin L.S., and Howlett A.C. Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol 34 (1988) 605-613
4. Matsuda L.A., Lolait S.J., Brownstein M.J., Young A.C., and Bonner T.I. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346 (1990) 561-564
5. Munro S., Thomas K.L., and Abu-Shaar M. Molecular characterization of a peripheral receptor for cannabinoids. Nature 365 (1993) 61-65
6. Herkenham M. Localization of cannabinoid receptors in brain and periphery. In: Pertwee R.G. (Ed). Cannabinoid receptors (1995), Academic Press, London 145-166
7. van Sickle M.D., Duncan M., Kingsley P.J., Mouihate A., Urbani P., Mackie K., et al. Identification and functional characterization of brainstem cannabinoid CB2 receptors. Science 310 (2005) 329-332
8. Di Marzo V., De Petrocellis L., Fezza F., Ligresti A., and Bisogno T. Anandamide receptors. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 377-391
9. Di Marzo V., and De Petrocellis L. Non-CB1 non-CB2 receptors for endocannabinoids. In: Onaivi E.S., Sugiura T., and Di Marzo V. (Eds). Endocannabinoids: The brain and body's marijuana and beyond (2006), Taylor & Francis, Boca Raton 151-174
10. Pertwee R.G. Pharmacological actions of cannabinoids. In: Pertwee R.G. (Ed). Cannabinoids (2004), Springer, Berlin 1-51
11. Brown AJ, Ueno S, Suen K, Dowell SJ, Wise A. Molecular identification of GPR55 as a third G protein-coupled receptor responsive to cannabinoid ligands. In: 2005 Symposium on the cannabinoids abstract; 2005. p. 16.
12. Sjo{combining double acute accent}gren A, Ryberg E, Lindblom A, Larsson N, Astrand A, Hjorth S, et al. A new receptor for cannabinoid ligands. In: 2005 Symposium on the cannabinoids abstract; 2005. p. 106.
13. 2+-dependent release from rat brain of cannabinoid receptor binding activity. J Neurochem 58 (1992) 780-782
14. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 (1992) 1946-1949
15. Mechoulam R., Fride E., and Di Marzo V. Endocannabinoids. Eur J Pharmacol 359 (1998) 1-18
16. Di Marzo V., De Petrocellis L., Bisogno T., Berger A., and Mechoulam R. Biology of endocannabinoids. In: Onaivi E.S. (Ed). Biology of marijuana (2002), Tayler & Francis, London 125-173
17. Pertwee R.G., and Ross R.A. Cannabinoid receptors and their ligands. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 101-121
18. Freund T.F., Katona I., and Piomelli D. Role of endogenous cannabinoids in synaptic signaling. Physiol Rev 83 (2003) 1017-1066
19. 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
20. Ueda N., Kurahashi Y., Yamamoto S., and Tokunaga T. Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J Biol Chem 270 (1995) 23823-23827
21. Di Marzo V., Fontana A., Cadas H., Schinelli S., Cimino G., Schwartz J.C., et al. Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature 372 (1994) 686-691
22. Sugiura T., Kondo S., Sukagawa A., Tonegawa T., Nakane S., Yamashita A., et al. 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 240 (1996) 53-62
23. Sugiura T., and Waku K. Cannabinoid receptors and their endogenous ligands. J Biochem 132 (2002) 7-12
24. Sugiura T., Oka S., Ikeda S., and Waku K. Occurrence, biosynthesis, and metabolism of endocannabinoid. In: Onaivi E.S., Sugiura T., and Di Marzo V. (Eds). Endocannabinoids: The brain and body's marijuana and beyond (2006), Taylor & Francis, Boca Raton 177-214
25. Sugiura T., Tokumura A., Gregory L., Nouchi T., Weintraub S.T., and Hanahan D.J. Biochemical characterization of the interaction of lipid phosphoric acids with human platelets: comparison with platelet activating factor. Arch Biochem Biophys 311 (1994) 358-368
26. Sugiura T., Itoh K., Waku K., and Hanahan D.J. Biological activities of N-acylethanolamine and N-acylethanolamine phosphate analogues. Proc Jpn Conf Biochem Lipids 36 (1994) 71-74 [in Japanese]
27. Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., et al. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem Biophys Res Commun 215 (1995) 89-97
28. Mechoulam R., Ben-Shabat S., Hanus L., Ligumsky M., Kaminski N.E., Schatz A.R., et al. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol 50 (1995) 83-90
29. Stella N., Schweitzer P., and Piomelli D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 (1997) 773-778
30. Gonsiorek W., Lunn C., Fan X., Narula S., Lundell D., and Hipkin R.W. Endocannabinoid 2-arachidonyl glycerol is a full agonist through human type 2 cannabinoid receptor: antagonism by anandamide. Mol Pharmacol 57 (2000) 1045-1050
31. Shoemaker J.L., Ruckle M.B., Mayeux P.R., and Prather P.L. Agonist-directed trafficking of response by endocannabinoids acting at CB2 receptors. J Pharmacol Exp Ther 315 (2005) 828-838
32. Franklin A., Parmentier-Batteur S., Walter L., Greenberg D.A., and Stella N. Palmitoylethanolamide increases after focal cerebral ischemia and potentiates microglial cell motility. J Neurosci 23 (2003) 7767-7775
33. Mukherjee S., Adams M., Whiteaker K., Daza A., Kage K., Cassar S., et al. Species comparison and pharmacological characterization of rat and human CB2 cannabinoid receptors. Eur J Pharmacol 505 (2004) 1-9
34. 2+ in neuroblastoma × glioma hybrid NG108-15 cells. Biochem Biophys Res Commun 229 (1996) 58-64
35. 2+ transient in NG108-15 cells. J Biochem 122 (1997) 890-895
36. Sugiura T., Kodaka T., Nakane S., Miyashita T., Kondo S., Suhara Y., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 (1999) 2794-2801
37. Sugiura T., Kondo S., Kishimoto S., Miyashita T., Nakane S., Kodaka T., et al. Evidence that 2-arachidonoylglycerol but not N-palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor. Comparison of the agonistic activities of various cannabinoid receptor ligands in HL-60 cells. J Biol Chem 275 (2000) 605-612
38. Sugiura T., Kodaka T., Kondo S., Tonegawa T., Nakane S., Kishimoto S., et al. Inhibition by 2-arachidonoylglycerol, a novel type of possible neuromodulator, of the depolarization-induced increase in intracellular free calcium in neuroblastoma × glioma hybrid NG108-15 cells. Biochem Biophys Res Commun 233 (1997) 207-210
39. Oz M., Tchugunova Y., and Dinc M. Differential effects of endogenous and synthetic cannabinoids on voltage-dependent calcium fluxes in rabbit T-tubule membranes: comparison with fatty acids. Eur J Pharmacol 502 (2004) 47-58
40. Guo J., and Ikeda S.R. Endocannabinoids modulate N-type calcium channels and G-protein-coupled inwardly rectifying potassium channels via CB1 cannabinoid receptors heterologously expressed in mammalian neurons. Mol Pharmacol 65 (2004) 665-674
41. 7-nicotinic acetylcholine receptor-mediated responses in Xenopus Oocytes. J Pharmacol Exp Ther 310 (2004) 1152-1160
42. Watanabe H., Vriens J., Prenen J., Droogmans G., Voets T., and Nilius B. Anandamide and arachidonic acid use epoxyeicosatrienoic acids to activate TRPV4 channels. Nature 424 (2003) 434-438
43. Hillard C.J. Biochemistry and pharmacology of the endocannabinoids arachidonylethanolamide and 2-arachidonylglycerol. Prostaglandins Other Lipid Mediat 61 (2000) 3-18
44. Savinainen J.R., Jarvinen T., Laine K., and Laitinen J.T. Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB1 receptor-dependent G-protein activation in rat cerebellar membranes. Br J Pharmacol 134 (2001) 664-672
45. Shoemaker J.L., Joseph B.K., Ruckle M.B., Mayeux P.R., and Prather P.L. The endocannabinoid noladin ether acts as a full agonist at human CB2 cannabinoid receptors. J Pharmacol Exp Ther 314 (2005) 868-875
46. 3H]GABA from synaptosomes isolated from the rat hippocampus. Neurochem Res 29 (2004) 1553-1561
47. Di S., Malcher-Lopes R., Marcheselli V.L., Bazan N.G., and Tasker J.G. Rapid glucocorticoid-mediated endocannabinoid release and opposing regulation of glutamate and gamma-aminobutyric acid inputs to hypothalamic magnocellular neurons. Endocrinology 146 (2005) 4292-4301
48. Di S., Boudaba C., Popescu I.R., Weng F.J., Harris C., Marcheselli V.L., et al. Activity-dependent release and actions of endocannabinoids in the rat hypothalamic supraoptic nucleus. J Physiol 569 (2005) 751-760
49. Kobayashi Y., Arai S., Waku K., and Sugiura T. Activation by 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, of p42/44 mitogen-activated protein kinase in HL-60 cells. J Biochem 129 (2001) 665-669
50. Derkinderen P., Valjent E., Toutant M., Corvol J.C., Enslen H., Ledent C., et al. Regulation of extracellular signal-regulated kinase by cannabinoids in hippocampus. J Neurosci 23 (2003) 2371-2382
51. + cells. J Biol Chem 280 (2005) 26735-26742
52. Carrier E.J., Kearn C.S., Barkmeier A.J., Breese N.M., Yang W., Nithipatikom K., et al. Cultured rat microglial cells synthesize the endocannabinoid 2-arachidonylglycerol, which increases proliferation via a CB2 receptor-dependent mechanism. Mol Pharmacol 65 (2004) 999-1007
53. Walter L., Franklin A., Witting A., Wade C., Xie Y., Kunos G., et al. Nonpsychotropic cannabinoid receptors regulate microglial cell migration. J Neurosci 23 (2003) 1398-1405
54. Sugiura T., Kishimoto S., Oka S., Gokoh M., and Waku K. Metabolism and physiological significance of anandamide and 2-arachidonoylglycerol, endogenous cannabinoid receptor ligands. In: Fonteh A.N., and Wykle R.L. (Eds). Arachidonate remodeling and inflammation (2004), Birkhäuser, Basel 211-237
55. Derkinderen P., Ledent C., Parmentier M., and Girault J.A. Cannabinoids activate p38 mitogen-activated protein kinases through CB1 receptors in hippocampus. J Neurochem 77 (2001) 957-960
56. Rueda D., Galve-Roperh I., Haro A., and Guzman M. The CB1 cannabinoid receptor is coupled to the activation of c-Jun N-terminal kinase. Mol Pharmacol 58 (2000) 814-820
57. +6,7 by cannabinoids in hippocampus. J Biol Chem 276 (2001) 38289-38296
58. Ameri A., and Simmet T. Effects of 2-arachidonylglycerol, an endogenous cannabinoid, on neuronal activity in rat hippocampal slices. Naunyn Schmiedebergs Arch Pharmacol 361 (2000) 265-272
59. 9-tetrahydrocannabinol antagonizes endocannabinoid modulation of synaptic transmission between hippocampal neurons in culture. Neuropharmacology 46 (2004) 709-715
60. Stefano G.B., Bilfinger T.V., Rialas C.M., and Deutsch D.G. 2-Arachidonyl-glycerol stimulates nitric oxide release from human immune and vascular tissues and invertebrate immunocytes by cannabinoid receptor 1. Pharmacol Res 42 (2000) 317-322
61. Maccarrone M., Pauselli R., Di Rienzo M., and Finazzi-Agro A. Binding, degradation and apoptotic activity of stearoylethanolamide in rat C6 glioma cells. Biochem J 366 (2002) 137-144
62. Vannacci A., Giannini L., Passani M.B., Di Felice A., Pierpaoli S., Zagli G., et al. The endocannabinoid 2-arachidonylglycerol decreases the immunological activation of guinea pig mast cells: involvement of nitric oxide and eicosanoids. J Pharmacol Exp Ther 311 (2004) 256-264
63. Lee M., Yang K.H., and Kaminski N.E. Effects of putative cannabinoid receptor ligands, anandamide and 2-arachidonyl-glycerol, on immune function in B6C3F1 mouse splenocytes. J Pharmacol Exp Ther 275 (1995) 529-536
64. Sipe J.C., Arbour N., Gerber A., and Beutler E. Reduced endocannabinoid immune modulation by a common cannabinoid 2 (CB2) receptor gene polymorphism: possible risk for autoimmune disorders. J Leukoc Biol 78 (2005) 231-238
65. Ouyang Y., Hwang S.G., Han S.H., and Kaminski N.E. Suppression of interleukin-2 by the putative endogenous cannabinoid 2-arachidonyl-glycerol is mediated through down-regulation of the nuclear factor of activated T cells. Mol Pharmacol 53 (1998) 676-683
66. Jorda M.A., Verbakel S.E., Valk P.J., Vankan-Berkhoudt Y.V., Maccarrone M., Finazzi-Agro A., et al. Hematopoietic cells expressing the peripheral cannabinoid receptor migrate in response to the endocannabinoid 2-arachidonoylglycerol. Blood 99 (2002) 2786-2793
67. Kishimoto S., Gokoh M., Oka S., Muramatsu M., Kajiwara T., Waku K., et al. 2-Arachidonoylglycerol induces the migration of HL-60 cells differentiated into macrophage-like cells and human peripheral blood monocytes through the cannabinoid CB2 receptor-dependent mechanism. J Biol Chem 278 (2003) 24469-24475
68. Oka S., Ikeda S., Kishimoto S., Gokoh M., Yanagimoto S., Waku K., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces the migration of EoL-1 human eosinophilic leukemia cells and human peripheral blood eosinophils. J Leukoc Biol 76 (2004) 1002-1009
69. Kishimoto S., Muramatsu M., Gokoh M., Oka S., Waku K., and Sugiura T. Endogenous cannabinoid receptor ligand induces the migration of human natural killer cells. J Biochem 137 (2005) 217-223
70. Maestroni G.J. The endogenous cannabinoid 2-arachidonoyl glycerol as in vivo chemoattractant for dendritic cells and adjuvant for Th1 response to a soluble protein. FASEB J 18 (2004) 1914-1916
71. Lunn C.A., Fine J.S., Rojas-Triana A., Jackson J.V., Fan X., Kung T.T., et al. A novel cannabinoid peripheral cannabinoid receptor-selective inverse agonist blocks leukocyte recruitment in vivo. J Pharmacol Exp Ther 316 (2006) 780-788
72. Gokoh M., Kishimoto S., Oka S., Mori M., Waku K., Ishima Y., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces rapid actin polymerization in HL-60 cells differentiated into macrophage-like cells. Biochem J 386 (2005) 583-589
73. Gokoh M., Kishimoto S., Oka S., Metani Y., and Sugiura T. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, enhances the adhesion of HL-60 cells differentiated into macrophage-like cells and human peripheral blood monocytes. FEBS Lett 579 (2005) 6473-6478
74. Rueda D., Navarro B., Martinez-Serrano A., Guzman M., and Galve-Roperh I. The endocannabinoid anandamide inhibits neuronal progenitor cell differentiation through attenuation of the Rap1/B-Raf/ERK pathway. J Biol Chem 277 (2002) 46645-46650
75. De Petrocellis L., Melck D., Palmisano A., Bisogno T., Laezza C., Bifulco M., et al. The endogenous cannabinoid anandamide inhibits human breast cancer cell proliferation. Proc Natl Acad Sci USA 95 (1998) 8375-8380
76. Melck D., De Petrocellis L., Orlando P., Bisogno T., Laezza C., Bifulco M., et al. Suppression of nerve growth factor Trk receptors and prolactin receptors by endocannabinoids leads to inhibition of human breast and prostate cancer cell proliferation. Endocrinology 141 (2000) 118-126
77. Jacobsson S.O., Wallin T., and Fowler C.J. Inhibition of rat C6 glioma cell proliferation by endogenous and synthetic cannabinoids. Relative involvement of cannabinoid and vanilloid receptors. J Pharmacol Exp Ther 299 (2001) 951-959
78. Ligresti A., Bisogno T., Matias I., De Petrocellis L., Cascio M.G., Cosenza V., et al. Possible endocannabinoid control of colorectal cancer growth. Gastroenterology 125 (2003) 677-687
79. Julien B., Grenard P., Teixeira-Clerc F., Van Nhieu J.T., Li L., Karsak M., et al. Antifibrogenic role of the cannabinoid receptor CB2 in the liver. Gastroenterology 128 (2005) 742-755
80. Nithipatikom K., Endsley M.P., Isbell M.A., Falck J.R., Iwamoto Y., Hillard C.J., et al. 2-Arachidonoylglycerol: a novel inhibitor of androgen-independent prostate cancer cell invasion. Cancer Res 64 (2004) 8826-8830
81. Nithipatikom K., Endsley M.P., Isbell M.A., Wheelock C.E., Hammock B.D., and Campbell W.B. A new class of inhibitors of 2-arachidonoylglycerol hydrolysis and invasion of prostate cancer cells. Biochem Biophys Res Commun 332 (2005) 1028-1033
82. Granberg M., Fowler C.J., and Jacobsson S.O. Effects of the cannabimimetic fatty acid derivatives 2-arachidonoylglycerol, anandamide, palmitoylethanolamide and methanandamide upon IgE-dependent antigen-induced β-hexosaminidase, serotonin and TNF-α release from rat RBL-2H3 basophilic leukaemic cells. Naunyn Schmiedebergs Arch Pharmacol 364 (2001) 66-73
83. Maccarrone M., Bari M., Menichelli A., Giuliani E., Del Principe D., and Finazzi-Agro A. Human platelets bind and degrade 2-arachidonoylglycerol, which activates these cells through a cannabinoid receptor. Eur J Biochem 268 (2001) 819-825
84. Kojima S., Sugiura T., Waku K., and Kamikawa Y. Contractile response to a cannabimimetic eicosanoid, 2-arachidonoylglycerol, of longitudinal smooth muscle from the guinea-pig distal colon in vitro. Eur J Pharmacol 444 (2002) 203-207
85. Stanke-Labesque F., Mallaret M., Lefebvre B., Hardy G., Caron F., and Bessard G. 2-Arachidonoyl glycerol induces contraction of isolated rat aorta: role of cyclooxygenase-derived products. Cardiovasc Res 63 (2004) 155-160
86. Gallily R., Breuer A., and Mechoulam R. 2-Arachidonylglycerol, an endogenous cannabinoid, inhibits tumor necrosis factor-α production in murine macrophages, and in mice. Eur J Pharmacol 406 (2000) R5-R7
87. Chang Y.H., Lee S.T., and Lin W.W. Effects of cannabinoids on LPS-stimulated inflammatory mediator release from macrophages: involvement of eicosanoids. J Cell Biochem 81 (2001) 715-723
88. Kaplan B.L., Ouyang Y., Rockwell C.E., Rao G.K., and Kaminski N.E. 2-Arachidonoyl-glycerol suppresses interferon-γ production in phorbol ester/ionomycin-activated mouse splenocytes independent of CB1 or CB2. J Leukoc Biol 77 (2005) 966-974
89. Kishimoto S., Kobayashi Y., Oka S., Gokoh M., Waku K., and Sugiura T. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells. J Biochem 135 (2004) 517-524
90. Oka S., Yanagimoto S., Ikeda S., Gokoh M., Kishimoto S., Waku K., et al. Evidence for the involvement of the cannabinoid CB2 receptor and its endogenous ligand 2-arachidonoylglycerol in 12-O-tetradecanoylphorbol-13-acetate-induced acute inflammation in mouse ear. J Biol Chem 280 (2005) 18488-18497
91. Kirkham T.C., Williams C.M., Fezza F., and Di Marzo V. Endocannabinoid levels in rat limbic forebrain and hypothalamus in relation to fasting, feeding and satiation: stimulation of eating by 2-arachidonoyl glycerol. Br J Pharmacol 136 (2002) 550-557
92. Kagota S., Yamaguchi Y., Nakamura K., Sugiura T., Waku K., and Kunitomo M. 2-Arachidonoylglycerol, a candidate of endothelium-derived hyperpolarizing factor. Eur J Pharmacol 415 (2001) 233-238
93. Mechoulam R., Fride E., Ben-Shabat S., Meiri U., and Horowitz M. Carbachol, an acetylcholine receptor agonist, enhances production in rat aorta of 2-arachidonoyl glycerol, a hypotensive endocannabinoid. Eur J Pharmacol 362 (1998) R1-R3
94. Jarai Z., Wagner J.A., Goparaju S.K., Wang L., Razdan R.K., Sugiura T., et al. Cardiovascular effects of 2-arachidonoyl glycerol in anesthetized mice. Hypertension 35 (2000) 679-684
95. 9-tetrahydrocannabinol and other cannnabinoids. J Pharmacol Exp Ther 300 (2002) 34-42
96. Panikashvili D., Simeonidou C., Ben-Shabat S., Hanus L., Breuer A., Mechoulam R., et al. An endogenous cannabinoid (2-AG) is neuroprotective after brain injury. Nature 413 (2001) 527-531
97. Panikashvili D., Mechoulam R., Beni S.M., Alexandrovich A., and Shohami E. CB1 cannabinoid receptors are involved in neuroprotection via NF-κB inhibition. J Cereb Blood Flow Metab 25 (2005) 477-484
98. Baker D., Pryce G., Croxford J.L., Brown P., Pertwee R.G., Makriyannis A., et al. Endocannabinoids control spasticity in a multiple sclerosis model. FASEB J 15 (2001) 300-302
99. Paria B.C., Ma W., Andrenyak D.M., Schmid P.C., Schmid H.H., Moody D.E., et al. Effects of cannabinoids on preimplantation mouse embryo development and implantation are mediated by brain-type cannabinoid receptors. Biol Reprod 58 (1998) 1490-1495
100. Sugiura T., and Waku K. 2-Arachidonoylglycerol and the cannabinoid receptors. Chem Phys Lipids 108 (2000) 89-106
101. McAllister S.D., and Abood M.E. Endocannabinoids and intracellular signaling. In: Onaivi E.S., Sugiura T., and Di Marzo V. (Eds). Endocannabinoids: The brain and body's marijuana and beyond (2006), Taylor & Francis, Boca Raton 119-131
102. Porter A.C., Sauer J.M., Knierman M.D., Becker G.W., Berna M.J., Bao J., et al. Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J Pharmacol Exp Ther 301 (2002) 1020-1024
103. Huang S.M., Bisogno T., Trevisani M., Al-Hayani A., De Petrocellis L., Fezza F., et al. An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors. Proc Natl Acad Sci USA 99 (2002) 8400-8405
104. Hanus L., Abu-Lafi S., Fride E., Breuer A., Vogel Z., Shalev D.E., et al. 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc Natl Acad Sci USA 98 (2001) 3662-3665
105. Fezza F., Bisogno T., Minassi A., Appendino G., Mechoulam R., and Di Marzo V. Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues. FEBS Lett 513 (2002) 294-298
106. Oka S., Tsuchie A., Tokumura A., Muramatsu M., Suhara Y., Takayama H., et al. Ether-linked analogue of 2-arachidonoylglycerol (noladin ether) was not detected in the brains of various mammalian species. J Neurochem 85 (2003) 1374-1381
107. Sugiura T., and Waku K. Composition of alkyl ether-linked phospholipids in mammalian tissues. In: Snyder F. (Ed). Platelet-activating factor and related lipid mediators (1987), Plenum Press, New York 55-85
108. 2+-dependent and -independent mechanisms. FEBS Lett 429 (1998) 152-156
109. Bisogno T., Berrendero F., Ambrosino G., Cebeira M., Ramos J.A., Fernandez-Ruiz J.J., et al. Brain regional distribution of endocannabinoids: implications for their biosynthesis and biological function. Biochem Biophys Res Commun 256 (1999) 377-380
110. Gonzalez S., Manzanares J., Berrendero F., Wenger T., Corchero J., Bisogno T., et al. Identification of endocannabinoids and cannabinoid CB1 receptor mRNA in the pituitary gland. Neuroendocrinology 70 (1999) 137-145
111. Pagotto U., Marsicano G., Fezza F., Theodoropoulou M., Grubler Y., Stalla J., et al. Normal human pituitary gland and pituitary adenomas express cannabinoid receptor type 1 and synthesize endogenous cannabinoids: first evidence for a direct role of cannabinoids on hormone modulation at the human pituitary level. J Clin Endocrinol Metab 86 (2001) 2687-2696
112. Giuffrida A., Parsons L.H., Kerr T.M., Rodriguez de Fonseca F., Navarro M., and Piomelli D. Dopamine activation of endogenous cannabinoid signaling in dorsal striatum. Nat Neurosci 2 (1999) 358-363
113. Berrendero F., Sepe N., Ramos J.A., Di Marzo V., and Fernandez-Ruiz J.J. Analysis of cannabinoid receptor binding and mRNA expression and endogenous cannabinoid contents in the developing rat brain during late gestation and early postnatal period. Synapse 33 (1999) 181-191
114. Valenti M., Vigano D., Casico M.G., Rubino T., Steardo L., Parolaro D., et al. Differential diurnal variations of anandamide and 2-arachidonoyl-glycerol levels in rat brain. Cell Mol Life Sci 61 (2004) 945-950
115. Di Marzo V., Hill M.P., Bisogno T., Crossman A.R., and Brotchie J.M. Enhanced levels of endogenous cannabinoids in the globus pallidus are associated with a reduction in movement in an animal model of Parkinson's disease. FASEB J 14 (2000) 1432-1438
116. Lastres-Becker I., Fezza F., Cebeira M., Bisogno T., Ramos J.A., Milone A., et al. Changes in endocannabinoid transmission in the basal ganglia in a rat model of Huntington's disease. Neuroreport 12 (2001) 2125-2129
117. Patel S., Rademacher D.J., and Hillard C.J. Differential regulation of the endocannabinoids anandamide and 2-arachidonylglycerol within the limbic forebrain by dopamine receptor activity. J Pharmacol Exp Ther 306 (2003) 880-888
118. Witting A., Weydt P., Hong S., Kliot M., Moller T., and Stella N. Endocannabinoids accumulate in spinal cord of SOD1 G93A transgenic mice. J Neurochem 89 (2004) 1555-1557
119. Cabranes A., Venderova K., de Lago E., Fezza F., Sanchez A., Mestre L., et al. Decreased endocannabinoid levels in the brain and beneficial effects of agents activating cannabinoid and/or vanilloid receptors in a rat model of multiple sclerosis. Neurobiol Dis 20 (2005) 207-217
120. Maresz K., Carrier E.J., Ponomarev E.D., Hillard C.J., and Dittel B.N. Modulation of the cannabinoid CB2 receptor in microglial cells in response to inflammatory stimuli. J Neurochem 95 (2005) 437-445
121. Gonzalez S., Cascio M.G., Fernandez-Ruiz J., Fezza F., Di Marzo V., and Ramos J.A. Changes in endocannabinoid contents in the brain of rats chronically exposed to nicotine, ethanol or cocaine. Brain Res 954 (2002) 73-81
122. 9-tetrahydrocannabinol-tolerant rats. J Neurochem 74 (2000) 1627-1635
123. Vigano D., Grazia Cascio M., Rubino T., Fezza F., Vaccani A., Di Marzo V., et al. Chronic morphine modulates the contents of the endocannabinoid, 2-arachidonoyl glycerol, in rat brain. Neuropsychopharmacology 28 (2003) 1160-1167
124. Gonzalez S., Valenti M., de Miguel R., Fezza F., Fernandez-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
125. 9-tetrahydrocannabinol-tolerant rats: an experimental model of cannabinoid abstinence. Drug Alcohol Depend 74 (2004) 159-170
126. Vigano D., Valenti M., Cascio M.G., Di Marzo V., Parolaro D., and Rubino T. Changes in endocannabinoid levels in a rat model of behavioural sensitization to morphine. Eur J Neurosci 20 (2004) 1849-1857
127. Rodriguez de Fonseca F., Del Arco I., Bermudez-Silva F.J., Bilbao A., Cippitelli A., and Navarro M. The endocannabinoid system: physiology and pharmacology. Alcohol Alcohol 40 (2005) 2-14
128. Arnold J.C. The role of endocannabinoid transmission in cocaine addiction. Pharmacol Biochem Behav 81 (2005) 396-406
129. Watanabe S., Doshi M., and Hamazaki T. n-3 Polyunsaturated fatty acid (PUFA) deficiency elevates and n-3 PUFA enrichment reduces brain 2-arachidonoylglycerol level in mice. Prostaglandins Leukot Essent Fatty Acids 69 (2003) 51-59
130. Hanus L., Avraham Y., Ben-Shushan D., Zolotarev O., Berry E.M., and Mechoulam R. Short-term fasting and prolonged semistarvation have opposite effects on 2-AG levels in mouse brain. Brain Res 983 (2003) 144-151
131. Huang S.M., Strangman N.M., and Walker J.M. Liquid chromatographic-mass spectrometric measurement of the endogenous cannabinoid 2-arachidonylglycerol in the spinal cord and peripheral nervous system. Zhongguo Yao Li Xue Bao 20 (1999) 1098-1102
132. Di Marzo V., Breivogel C.S., Tao Q., Bridgen D.T., Razdan R.K., Zimmer A.M., et al. Levels, metabolism, and pharmacological activity of anandamide in CB1 cannabinoid receptor knockout mice: evidence for non-CB1, non-CB2 receptor-mediated actions of anandamide in mouse brain. J Neurochem 75 (2000) 2434-2444
133. Bisogno T., Delton-Vandenbroucke I., Milone A., Lagarde M., and Di Marzo V. Biosynthesis and inactivation of N-arachidonoylethanolamine (anandamide) and N-docosahexaenoylethanolamine in bovine retina. Arch Biochem Biophys 370 (1999) 300-307
134. Straiker A., Stella N., Piomelli D., Mackie K., Karten H.J., and Maguire G. Cannabinoid CB1 receptors and ligands in vertebrate retina: localization and function of an endogenous signaling system. Proc Natl Acad Sci USA 96 (1999) 14565-14570
135. Schmid P.C., Schwartz K.D., Smith C.N., Krebsbach R.J., Berdyshev E.V., and Schmid H.H.O. A sensitive endocannabinoid assay. The simultaneous analysis of N-acylethanolamines and 2-monoacylglycerols. Chem Phys Lipids 104 (2000) 185-191
136. Pinto L., Izzo A.A., Cascio M.G., Bisogno T., Hospodar-Scott K., Brown D.R., et al. Endocannabinoids as physiological regulators of colonic propulsion in mice. Gastroenterology 123 (2002) 227-234
137. Izzo A.A., Fezza F., Capasso R., Bisogno T., Pinto L., and Iuvone T. Cannabinoid CB1-receptor mediated regulation of gastrointestinal motility in mice in a model of intestinal inflammation. Br J Pharmacol 134 (2001) 563-570
138. Di Marzo V., Sepe N., De Petrocellis L., Berger A., Crozier G., Fride E., et al. Trick or treat from food endocannabinoids?. Nature 396 (1998) 636-637
139. Beaulieu P., Bisogno T., Punwar S., Farquhar-Smith W.P., Ambrosino G., Di Marzo V., et al. Role of the endogenous cannabinoid system in the formalin test of persistent pain in the rat. Eur J Pharmacol 396 (2000) 85-92
140. Wang Y., Liu Y., Ito Y., Hashiguchi T., Kitajima I., Yamakuchi M., et al. Simultaneous measurement of anandamide and 2-arachidonoylglycerol by polymyxin b-selective adsorption and subsequent high-performance liquid chromatography analysis: increase in endogenous cannabinoids in the sera of patients with endotoxic shock. Anal Biochem 294 (2001) 73-82
141. Rouzer C.A., Ghebreselasie K., and Marnett L.J. Chemical stability of 2-arachidonylglycerol under biological conditions. Chem Phys Lipids 119 (2002) 69-82
142. van der Stelt M., van Kuik J.A., Bari M., van Zadelhoff G., Leeflang B.R., Veldink G.A., et al. Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase. J Med Chem 45 (2002) 3709-3720
143. Valenti M., Cottone E., Martinez R., De Pedro N., Rubio M., Viveros M.P., et al. The endocannabinoid system in the brain of Carassius auratus and its possible role in the control of food intake. J Neurochem 95 (2005) 662-672
144. 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
145. De Petrocellis L., Melck D., Bisogno T., Milone A., and Di Marzo V. Finding of the endocannabinoid signalling system in Hydra, a very primitive organism: possible role in the feeding response. Neuroscience 92 (1999) 377-387
146. Matias I., Bisogno T., Melck D., Vandenbulcke F., Verger-Bocquet M., De Petrocellis L., et al. Evidence for an endocannabinoid system in the central nervous system of the leech Hirudo medicinalis. Brain Res Mol Brain Res 87 (2001) 145-159
147. 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 1633 (2003) 61-67
148. Matias I., McPartland J.M., and Di Marzo V. Occurrence and possible biological role of the endocannabinoid system in the sea squirt Ciona intestinalis. J Neurochem 93 (2005) 1141-1156
149. McPartland J., Di Marzo V., De Petrocellis L., Mercer A., and Glass M. Cannabinoid receptors are absent in insects. J Comp Neurol 436 (2001) 423-429
150. Sugiura T., Yoshinaga N., Kondo S., Waku K., and Ishima Y. Generation of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, in picrotoxinin-administered rat brain. Biochem Biophys Res Commun 271 (2000) 654-658
151. Sugiura T., Yoshinaga N., and Waku K. Rapid generation of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, in rat brain after decapitation. Neurosci Lett 297 (2001) 175-178
152. Maccarrone M., Attina M., Cartoni A., Bari M., and Finazzi-Agro A. Gas chromatography-mass spectrometry analysis of endogenous cannabinoids in healthy and tumoral human brain and human cells in culture. J Neurochem 76 (2001) 594-601
153. Gubellini P., Picconi B., Bari M., Battista N., Calabresi P., Centonze D., et al. Experimental parkinsonism alters endocannabinoid degradation: implications for striatal glutamatergic transmission. J Neurosci 22 (2002) 6900-6907
154. Mascolo N., Izzo A.A., Ligresti A., Costagliola A., Pinto L., Cascio M.G., et al. The endocannabinoid system and the molecular basis of paralytic ileus in mice. FASEB J 16 (2002) 1973-1975
155. Pacher P., Batkai S., Osei-Hyiaman D., Offertaler L., Liu J., Harvey-White J., et al. Hemodynamic profile, responsiveness to anandamide, and baroreflex sensitivity of mice lacking fatty acid amide hydrolase. Am J Physiol Heart Circ Physiol 289 (2005) H533-H541
156. Petersen G., Moesgaard B., Schmid P.C., Schmid H.H.O., Broholm H., Kosteljanetz M., et al. Endocannabinoid metabolism in human glioblastomas and meningiomas compared to human non-tumour brain tissue. J Neurochem 93 (2005) 299-309
157. Matias I., Leonhardt M., Lesage J., De Petrocellis L., Dupouy J.P., Vieau D., et al. Effect of maternal under-nutrition on pup body weight and hypothalamic endocannabinoid levels. Cell Mol Life Sci 60 (2003) 382-389
158. + coordination tandem mass spectrometry. Anal Biochem 314 (2003) 8-15
159. Prescott S.M., and Majerus P.W. Characterization of 1,2-diacylglycerol hydrolysis in human platelets. Demonstration of an arachidonoyl-monoacylglycerol intermediate. J Biol Chem 258 (1983) 764-769
160. Hasegawa-Sasaki H. Early changes in inositol lipids and their metabolites induced by platelet-derived growth factor in quiescent Swiss mouse 3T3 cells. Biochem J 232 (1985) 99-109
161. Gammon C.M., Allen A.C., and Morell P. Bradykinin stimulates phosphoinositide hydrolysis and mobilization of arachidonic acid in dorsal root ganglion neurons. J Neurochem 53 (1989) 95-101
162. Bisogno T., Sepe N., Melck D., Maurelli S., De Petrocellis L., and Di Marzo V. Biosynthesis, release and degradation of the novel endogenous cannabimimetic metabolite 2-arachidonoylglycerol in mouse neuroblastoma cells. Biochem J 322 (1997) 671-677
163. Sugiura T., Kodaka T., Nakane S., Kishimoto S., Kondo S., and Waku K. Detection of an endogenous cannabimimetic molecule, 2-arachidonoylglycerol, and cannabinoid CB1 receptor mRNA in human vascular cells: is 2-arachidonoylglycerol a possible vasomodulator?. Biochem Biophys Res Commun 243 (1998) 838-843
164. Gauthier K.M., Baewer D.V., Hittner S., Hillard C.J., Nithipatikom K., Reddy D.S., et al. Endothelium-derived 2-arachidonylglycerol: an intermediate in vasodilatory eicosanoid release in bovine coronary arteries. Am J Physiol Heart Circ Physiol 288 (2005) H1344-H1351
165. Basavarajappa B.S., Saito M., Cooper T.B., and Hungund B.L. Stimulation of cannabinoid receptor agonist 2-arachidonylglycerol by chronic ethanol and its modulation by specific neuromodulators in cerebellar granule neurons. Biochim Biophys Acta 1535 (2000) 78-86
166. Stella N., and Piomelli D. Receptor-dependent formation of endogenous cannabinoids in cortical neurons. Eur J Pharmacol 425 (2001) 189-196
167. Marsicano G., Wotjak C.T., Azad S.C., Bisogno T., Rammes G., Cascio M.G., et al. The endogenous cannabinoid system controls extinction of aversive memories. Nature 418 (2002) 530-534
168. Hohmann A.G., Suplita R.L., Bolton N.M., Neely M.H., Fegley D., Mangieri R., et al. An endocannabinoid mechanism for stress-induced analgesia. Nature 435 (2005) 1108-1112
169. McVey D.C., Schmid P.C., Schmid H.H.O., and Vigna S.R. Endocannabinoids induce ileitis in rats via the capsaicin receptor (VR1). J Pharmacol Exp Ther 304 (2003) 713-722
170. Izzo A.A., Capasso F., Costagliola A., Bisogno T., Marsicano G., Ligresti A., et al. An endogenous cannabinoid tone attenuates cholera toxin-induced fluid accumulation in mice. Gastroenterology 125 (2003) 765-774
171. Witting A., Walter L., Wacker J., Moller T., and Stella N. P2X7 receptors control 2-arachidonoylglycerol production by microglial cells. Proc Natl Acad Sci USA 101 (2004) 3214-3219
172. Carrier E.J., Kearn C.S., Barkmeier A.J., Breese N.M., Yang W., Nithipatikom K., et al. Cultured rat microglial cells synthesize the endocannabinoid 2-arachidonylglycerol, which increases proliferation via a CB2 receptor-dependent mechanism. Mol Pharmacol 65 (2004) 999-1007
173. Walter L., and Stella N. Endothelin-1 increases 2-arachidonoyl glycerol (2-AG) production in astrocytes. Glia 44 (2003) 85-90
174. Walter L., Dinh T., and Stella N. ATP induces a rapid and pronounced increase in 2-arachidonoylglycerol production by astrocytes, a response limited by monoacylglycerol lipase. J Neurosci 24 (2004) 8068-8074
175. Wallace M.J., Blair R.E., Falenski K.W., Martin B.R., and DeLorenzo R.J. The endogenous cannabinoid system regulates seizure frequency and duration in a model of temporal lobe epilepsy. J Pharmacol Exp Ther 307 (2003) 129-137
176. Rademacher D.J., Patel S., Ho W.S., Savoie A.M., Rusch N.J., Gauthier K.M., et al. U-46619 but not serotonin increases endocannabinoid content in middle cerebral artery: evidence for functional relevance. Am J Physiol Heart Circ Physiol 288 (2005) H2694-H2701
177. Motobe T., Hashiguchi T., Uchimura T., Yamakuchi M., Taniguchi N., Komiya S., et al. Endogenous cannabinoids are candidates for lipid mediators of bone cement implantation syndrome. Shock 21 (2004) 8-12
178. Varga K., Wagner J.A., Bridgen D.T., and Kunos G. Platelet- and macrophage-derived endogenous cannabinoids are involved in endotoxin-induced hypotension. FASEB J 12 (1998) 1035-1044
179. Di Marzo V., Bisogno T., De Petrocellis L., Melck D., Orlando P., Wagner J.A., et al. Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages. Eur J Biochem 264 (1999) 258-267
180. Berdyshev E.V., Schmid P.C., Krebsbach R.J., and Schmid H.H.O. Activation of PAF receptors results in enhanced synthesis of 2-arachidonoylglycerol (2-AG) in immune cells. FASEB J 15 (2001) 2171-2178
181. Liu J., Batkai S., Pacher P., Harvey-White J., Wagner J.A., Cravatt B.F., et al. Lipopolysaccharide induces anandamide synthesis in macrophages via CD14/MAPK/phosphoinositide 3-kinase/NF-κB independently of platelet-activating factor. J Biol Chem 278 (2003) 45034-45039
182. Nakane S., Oka S., Arai S., Waku K., Ishima Y., Tokumura A., et al. 2-Arachidonoyl-sn-glycero-3-phosphate, an arachidonic acid-containing lysophosphatidic acid: occurrence and rapid enzymatic conversion to 2-arachidonoyl-sn-glycerol, a cannabinoid receptor ligand, in rat brain. Arch Biochem Biophys 402 (2002) 51-58
183. Moriyama T., Urade R., and Kito M. Purification and characterization of diacylglycerol lipase from human platelets. J Biochem 125 (1999) 1077-1085
184. Bisogno T., Howell F., Williams G., Minassi A., Cascio M.G., Ligresti A., et al. Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain. J Cell Biol 163 (2003) 463-468
185. 1 followed by lysophosphoinositide-specific phospholipase C in rat brain. J Neurochem 61 (1993) 1874-1881
186. Tsutsumi T., Kobayashi T., Ueda H., Yamauchi E., Watanabe S., and Okuyama H. Lysophosphoinositide-specific phospholipase C in rat brain synaptic plasma membranes. Neurochem Res 19 (1994) 399-406
187. Bisogno T., Melck D., De Petrocellis L., and Di Marzo V. Phosphatidic acid as the biosynthetic precursor of the endocannabinoid 2-arachidonoylglycerol in intact mouse neuroblastoma cells stimulated with ionomycin. J Neurochem 72 (1999) 2113-2119
188. Konrad R.J., Major C.D., and Wolf B.A. Diacylglycerol hydrolysis to arachidonic acid is necessary for insulin secretion from isolated pancreatic islets: sequential actions of diacylglycerol and monoacylglycerol lipases. Biochemistry 33 (1994) 13284-13294
189. Goparaju S.K., Ueda N., Taniguchi K., and Yamamoto S. Enzymes of porcine brain hydrolyzing 2-arachidonoylglycerol, an endogenous ligand of cannabinoid receptors. Biochem Pharmacol 57 (1999) 417-423
190. Farooqui A.A., Anderson D.K., Flynn C., Bradel E., Means E.D., and Horrocks L.A. Stimulation of mono- and diacylglycerol lipase activities by bradykinin in neural cultures. Biochem Biophys Res Commun 166 (1990) 1001-1009
191. Karlsson M., Contreras J.A., Hellman U., Tornqvist H., and Holm C. cDNA cloning, tissue distribution, and identification of the catalytic triad of monoglyceride lipase. Evolutionary relationship to esterases, lysophospholipases, and haloperoxidases. J Biol Chem 272 (1997) 27218-27223
192. Dinh T.P., Carpenter D., Leslie F.M., Freund T.F., Katona I., Sensi S.L., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99 (2002) 10819-10824 Erratum: Proc Natl Acad Sci USA 2002;99:13961
193. Gulyas A.I., Cravatt B.F., Bracey M.H., Dinh T.P., Piomelli D., Boscia F., et al. Segregation of two endocannabinoid-hydrolyzing enzymes into pre- and postsynaptic compartments in the rat hippocampus, cerebellum and amygdala. Eur J Neurosci 20 (2004) 441-458
194. Dinh T.P., Kathuria S., and Piomelli D. RNA interference suggests a primary role for monoacylglycerol lipase in the degradation of the endocannabinoid 2-arachidonoylglycerol. Mol Pharmacol 66 (2004) 1260-1264
195. Makara J.K., Mor M., Fegley D., Szabo S.I., Kathuria S., Astarita G., et al. Selective inhibition of 2-AG hydrolysis enhances endocannabinoid signaling in hippocampus. Nat Neurosci 8 (2005) 1139-1141
196. Saario S.M., Savinainen J.R., Laitinen J.T., Jarvinen T., and Niemi R. Monoglyceride lipase-like enzymatic activity is responsible for hydrolysis of 2-arachidonoylglycerol in rat cerebellar membranes. Biochem Pharmacol 67 (2004) 1381-1387
197. Saario S.M., Salo O.M., Nevalainen T., Poso A., Laitinen J.T., Jarvinen T., et al. Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chem Biol 12 (2005) 649-656
198. Di Marzo V., Bisogno T., Sugiura T., Melck D., and De Petrocellis L. The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal- and basophil-like cells: connections with anandamide. Biochem J 331 (1998) 15-19
199. Goparaju S.K., Ueda N., Yamaguchi H., and Yamamoto S. Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. FEBS Lett 422 (1998) 69-73
200. de Lago E., Petrosino S., Valenti M., Morera E., Ortega-Gutierrez S., Fernandez-Ruiz J., et al. Effect of repeated systemic administration of selective inhibitors of endocannabinoid inactivation on rat brain endocannabinoid levels. Biochem Pharmacol 70 (2005) 446-452
201. Lichtman A.H., Hawkins E.G., Griffin G., and Cravatt B.F. Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo. J Pharmacol Exp Ther 302 (2002) 73-79
202. Kanoh H., Iwata T., Ono T., and Suzuki T. Immunological characterization of sn-1,2-diacylglycerol and sn-2-monoacylglycerol kinase from pig brain. J Biol Chem 261 (1986) 5597-5602
203. Shim Y.H., Lin C.H., and Strickland K.P. The purification and properties of monoacylglycerol kinase from bovine brain. Biochem Cell Biol 67 (1989) 233-241
204. Simpson C.M., Itabe H., Reynolds C.N., King W.C., and Glomset J.A. Swiss 3T3 cells preferentially incorporate sn-2-arachidonoyl monoacylglycerol into sn-1-stearoyl-2-arachidonoyl phosphatidylinositol. J Biol Chem 266 (1991) 15902-15909
205. Kozak K.R., Rowlinson S.W., and Marnett L.J. Oxygenation of the endocannabinoid, 2-arachidonylglycerol, to glyceryl prostaglandins by cyclooxygenase-2. J Biol Chem 275 (2000) 33744-33749
206. Kozak K.R., Prusakiewicz J.J., Rowlinson S.W., Schneider C., and Marnett L.J. Amino acid determinants in cyclooxygenase-2 oxygenation of the endocannabinoid 2-arachidonylglycerol. J Biol Chem 276 (2001) 30072-30077
207. Kozak K.R., Crews B.C., Morrow J.D., Wang L.H., Ma Y.H., Weinander R., et al. Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 277 (2002) 44877-44885
208. Rouzer C.A., and Marnett L.J. Glycerylprostaglandin synthesis by resident peritoneal macrophages in response to a zymosan stimulus. J Biol Chem 280 (2005) 26690-26700
209. Kozak K.R., Gupta R.A., Moody J.S., Ji C., Boeglin W.E., DuBois R.N., et al. 15-Lipoxygenase metabolism of 2-arachidonylglycerol. Generation of a peroxisome proliferator-activated receptor alpha agonist. J Biol Chem 277 (2002) 23278-23286
210. Moody J.S., Kozak K.R., Ji C., and Marnett L.J. Selective oxygenation of the endocannabinoid 2-arachidonylglycerol by leukocyte-type 12-lipoxygenase. Biochemistry 40 (2001) 861-866
211. 2 mobilizes calcium and activates signal transduction in RAW264.7 cells. Proc Natl Acad Sci USA 101 (2004) 1840-1845
212. Kozak K.R., Crews B.C., Ray J.L., Tai H.H., Morrow J.D., and Marnett L.J. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. J Biol Chem 276 (2001) 36993-36998
213. Kozak K.R., and Marnett L.J. Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 211-220
214. Fowler C.J., and Jacobsson S.O. Cellular transport of anandamide, 2-arachidonoylglycerol and palmitoylethanolamide - targets for drug development?. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 193-200
215. Ho W.S.V., and Hillard C.J. Modulators of endocannabinoid enzymic hydrolysis and membrane transport. In: Pertwee R.G. (Ed). Cannabinoids (2004), Springer, Berlin 187-207
216. Glaser S.T., Abumrad N.A., Fatade F., Kaczocha M., Studholme K.M., and Deutsch D.G. Evidence against the presence of an anandamide transporter. Proc Natl Acad Sci USA 100 (2003) 4269-4274
217. Ortega-Gutierrez S., Hawkins E.G., Viso A., Lopez-Rodriguez M.L., and Cravatt B.F. Comparison of anandamide transport in FAAH wild-type and knockout neurons: evidence for contributions by both FAAH and the CB1 receptor to anandamide uptake. Biochemistry 43 (2004) 8184-8190
218. Moore S.A., Nomikos G.G., Dickason-Chesterfield A.K., Schober D.A., Schaus J.M., Ying B.P., et al. Identification of a high-affinity binding site involved in the transport of endocannabinoids. Proc Natl Acad Sci USA 102 (2005) 17852-17857
219. Beltramo M., and Piomelli D. Carrier-mediated transport and enzymatic hydrolysis of the endogenous cannabinoid 2-arachidonylglycerol. Neuroreport 11 (2000) 1231-1235
220. Bisogno T., MacCarrone M., De Petrocellis L., Jarrahian A., Finazzi-Agro A., Hillard C., et al. The uptake by cells of 2-arachidonoylglycerol, an endogenous agonist of cannabinoid receptors. Eur J Biochem 268 (2001) 1982-1989
221. Hajos N., Kathuria S., Dinh T., Piomelli D., and Freund T.F. Endocannabinoid transport tightly controls 2-arachidonoyl glycerol actions in the hippocampus: effects of low temperature and the transport inhibitor AM404. Eur J Neurosci 19 (2004) 2991-2996
222. Sugiura T., Kondo S., Kodaka T., Nakane S., Yamashita A., Kishimoto S., et al. Biosynthesis and actions of anandamide and 2-arachidonoylglycerol: two endogenous cannabimimetic molecules. In: Riemesma R.A., Armstrong R., Kelly W., and Wilson R. (Eds). Essential fatty acids and eicosanoids (1998), AOCS Press, Champaign 380-384
223. Di Marzo V., Melck D., Bisogno T., and De Petrocellis L. Endocannabinoids: endogenous cannabinoid receptor ligands with neuromodulatory action. Trends Neurosci 21 (1998) 521-528 Erratum: Trends Neurosci 1999;22:80
224. Schlicker E., and Kathmann M. Modulation of transmitter release via presynaptic cannabinoid receptors. Trends Pharmacol Sci 22 (2001) 565-572
225. Nakanishi S., Maeda N., and Mikoshiba K. Immunohistochemical localization of an inositol 1,4,5-trisphosphate receptor, P400, in neural tissue: studies in developing and adult mouse brain. J Neurosci 11 (1991) 2075-2086
226. Collins D.R., Pertwee R.G., and Davies S.N. The action of synthetic cannabinoids on the induction of long-term potentiation in the rat hippocampal slice. Eur J Pharmacol 259 (1994) R7-R8
227. Terranova J.P., Michaud J.C., Le Fur G., and Soubrie P. Inhibition of long-term potentiation in rat hippocampal slices by anandamide and WIN55212-2: reversal by SR141716 A, a selective antagonist of CB1 cannabinoid receptors. Naunyn Schmiedebergs Arch Pharmacol 352 (1995) 576-579
228. A responses in hippocampal pyramidal cells. J Neurosci 12 (1992) 4122-4132
229. Vincent P., Armstrong C.M., and Marty A. Inhibitory synaptic currents in rat cerebellar Purkinje cells: modulation by postsynaptic depolarization. J Physiol 456 (1992) 453-471
230. Pitler T.A., and Alger B.E. Depolarization-induced suppression of GABAergic inhibition in rat hippocampal pyramidal cells: G protein involvement in a presynaptic mechanism. Neuron 13 (1994) 1447-1455
231. Ohno-Shosaku T., Sawada S., and Yamamoto C. Properties of depolarization-induced suppression of inhibitory transmission in cultured rat hippocampal neurons. Pflugers Arch 435 (1998) 273-279
232. Ohno-Shosaku T., Maejima T., and Kano M. Endogenous cannabinoids mediate retrograde signals from depolarized postsynaptic neurons to presynaptic terminals. Neuron 29 (2001) 729-738
233. Wilson R.I., and Nicoll R.A. Endogenous cannabinoids mediate retrograde signalling at hippocampal synapses. Nature 410 (2001) 588-592
234. Kreitzer A.C., and Regehr W.G. Retrograde inhibition of presynaptic calcium influx by endogenous cannabinoids at excitatory synapses onto Purkinje cells. Neuron 29 (2001) 717-727
235. Wilson R.I., Kunos G., and Nicoll R.A. Presynaptic specificity of endocannabinoid signaling in the hippocampus. Neuron 31 (2001) 453-462
236. Varma N., Carlson G.C., Ledent C., and Alger B.E. Metabotropic glutamate receptors drive the endocannabinoid system in hippocampus. J Neurosci 21 (2001) RC188
237. Yoshida T., Hashimoto K., Zimmer A., Maejima T., Araishi K., and Kano M. The cannabinoid CB1 receptor mediates retrograde signals for depolarization-induced suppression of inhibition in cerebellar Purkinje cells. J Neurosci 22 (2002) 1690-1697
238. Lenz R.A., Wagner J.J., and Alger B.E. N- and L-type calcium channel involvement in depolarization-induced suppression of inhibition in rat hippocampal CA1 cells. J Physiol 512 (1998) 61-73
239. Maejima T., Hashimoto K., Yoshida T., Aiba A., and Kano M. Presynaptic inhibition caused by retrograde signal from metabotropic glutamate to cannabinoid receptors. Neuron 31 (2001) 463-475
240. Kreitzer A.C., and Regehr W.G. Cerebeller depolarization-induced suppression of inhibition is mediated by endogenous cannabinoids. J Neurosci 21 (2001) RC174
241. Diana M.A., Levenes C., Mackie K., and Marty A. Short-term retrograde inhibition of GABAergic synaptic currents in rat Purkinje cells is mediated by endogenous cannabinoids. J Neurosci 22 (2002) 200-208
242. Yanovsky Y., Mades S., and Misgeld U. Retrograde signaling changes the venue of postsynaptic inhibition in rat substantia nigra. Neuroscience 122 (2003) 317-328
243. Kim J., and Alger B.E. Inhibition of cyclooxygenase-2 potentiates retrograde endocannabinoid effects in hippocampus. Nat Neurosci 7 (2004) 697-698
244. Fortin D.A., Trettel J., and Levine E.S. Brief trains of action potentials enhance pyramidal neuron excitability via endocannabinoid-mediated suppression of inhibition. J Neurophysiol 92 (2004) 2105-2112
245. Trettel J., Fortin D.A., and Levine E.S. Endocannabinoid signalling selectively targets perisomatic inhibitory inputs to pyramidal neurones in juvenile mouse neocortex. J Physiol 556 (2004) 95-107
246. Diana M.A., and Marty A. Endocannabinoid-mediated short-term synaptic plasticity: depolarization-induced suppression of inhibition (DSI) and depolarization-induced suppression of excitation (DSE). Br J Pharmacol 142 (2004) 9-19
247. Melis M., Perra S., Muntoni A.L., Pillolla G., Lutz B., Marsicano G., et al. Prefrontal cortex stimulation induces 2-arachidonoyl-glycerol-mediated suppression of excitation in dopamine neurons. J Neurosci 24 (2004) 10707-10715
248. Zhuang S., Hampson R.E., and Deadwyler S.A. Behaviorally relevant endocannabinoid action in hippocampus: dependence on temporal summation of multiple inputs. Behav Pharmacol 16 (2005) 463-471
249. Isokawa M., and Alger B.E. Retrograde endocannabinoid regulation of GABAergic inhibition in the rat dentate gyrus granule cell. J Physiol 567 (2005) 1001-1010
250. Zhu P.J., and Lovinger D.M. Retrograde endocannabinoid signaling in a postsynaptic neuron/synaptic bouton preparation from basolateral amygdala. J Neurosci 25 (2005) 6199-6207
251. Jo Y.H., Chen Y.J., Chua Jr. S.C., Talmage D.A., and Role L.W. Integration of endocannabinoid and leptin signaling in an appetite-related neural circuit. Neuron 48 (2005) 1055-1066
252. Carlson G., Wang Y., and Alger B.E. Endocannabinoids facilitate the induction of LTP in the hippocampus. Nat Neurosci 5 (2002) 723-724
253. Robbe D., Kopf M., Remaury A., Bockaert J., and Manzoni O.J. Endogenous cannabinoids mediate long-term synaptic depression in the nucleus accumbens. Proc Natl Acad Sci USA 99 (2002) 8384-8388
254. Gerdeman G.L., Ronesi J., and Lovinger D.M. Postsynaptic endocannabinoid release is critical to long-term depression in the striatum. Nature Neurosci 5 (2002) 446-451
255. Chevaleyre V., and Castillo P.E. Heterosynaptic LTD of hippocampal GABAergic synapses: a novel role of endocannabinoids in regulating excitability. Neuron 38 (2003) 461-472
256. Chevaleyre V., and Castillo P.E. Endocannabinoid-mediated metaplasticity in the hippocampus. Neuron 43 (2004) 871-881
257. Chen K., Ratzliff A., Hilgenberg L., Gulyas A., Freund T.F., Smith M., et al. Long-term plasticity of endocannabinoid signaling induced by developmental febrile seizures. Neuron 39 (2003) 599-611
258. Galante M., and Diana M.A. Group I metabotropic glutamate receptors inhibit GABA release at interneuron-Purkinje cell synapses through endocannabinoid production. J Neurosci 24 (2004) 4865-4874
259. 2+-assisted metabotropic glutamate receptor subtype 1 to phospholipase Cβ4 signaling cascade in the cerebellum. J Neurosci 25 (2005) 6826-6835
260. Jung K.M., Mangieri R., Stapleton C., Kim J., Fegley D., Wallace M., et al. Stimulation of endocannabinoid formation in brain slice cultures through activation of group I metabotropic glutamate receptors. Mol Pharmacol 68 (2005) 1196-1202
261. Straiker A., and Mackie K. Depolarization-induced suppression of excitation in murine autaptic hippocampal neurones. J Physiol 569 (2005) 501-517
262. 2+ dependency for triggering retrograde endocannabinoid signal. Neuron 45 (2005) 257-268
263. Edwards D.A., Kim J., and Alger B.E. Multiple mechanisms of endocannabinoid response initiation in hippocampus. J Neurophysiol 95 (2006) 67-75
264. Safo P.K., and Regehr W.G. Endocannabinoids control the induction of cerebellar LTD. Neuron 48 (2005) 647-659
265. Mechoulam R., Panikashvili D., and Shohami E. Cannabinoids and brain injury: therapeutic implications. Trends Mol Med 8 (2002) 58-61
266. van der Stelt M., Veldhuis W.B., Maccarrone M., Bar P.R., Nicolay K., Veldink G.A., et al. Acute neuronal injury, excitotoxicity, and the endocannabinoid system. Mol Neurobiol 26 (2002) 317-346
267. Veldhuis W.B., van der Stelt M., Wadman M.W., van Zadelhoff G., Maccarrone M., Fezza F., et al. Neuroprotection by the endogenous cannabinoid anandamide and arvanil against in vivo excitotoxicity in the rat: role of vanilloid receptors and lipoxygenases. J Neurosci 23 (2003) 4127-4133
268. Kim S.H., Won S.J., Mao X.O., Jin K., and Greenberg D.A. Molecular mechanisms of cannabinoid protection from neuronal excitotoxicity. Mol Pharmacol 69 (2006) 691-696
269. Marsicano G., Goodenough S., Monory K., Hermann H., Eder M., Cannich A., et al. CB1 cannabinoid receptors and on-demand defense against excitotoxicity. Science 302 (2003) 84-88
270. Sinor A.D., Irvin S.M., and Greenberg D.A. Endocannabinoids protect cerebral cortical neurons from in vitro ischemia in rats. Neurosci Lett 278 (2000) 157-160
271. McCarron R.M., Shohami E., Panikashvili D., Chen Y., Golech S., Strasser A., et al. Antioxidant properties of the vasoactive endocannabinoid, 2-arachidonoyl glycerol (2-AG). Acta Neurochir Suppl 86 (2003) 271-275
272. Baker D., Pryce G., Croxford J.L., Brown P., Pertwee R.G., Huffman J.W., et al. Cannabinoids control spasticity and tremor in a multiple sclerosis model. Nature 404 (2000) 84-87
273. 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
274. Muthian S., Rademacher D.J., Roelke C.T., Gross G.J., and Hillard C.J. Anandamide content is increased and CB1 cannabinoid receptor blockade is protective during transient, focal cerebral ischemia. Neuroscience 129 (2004) 743-750
275. Walker J.M., and Huang S.M. Endocannabinoids in pain modulation. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 235-242
276. Rice A.S., Farquhar-Smith W.P., and Nagy I. Endocannabinoids and pain: spinal and peripheral analgesia in inflammation and neuropathy. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 243-256
277. Connell K., Bolton N., Olsen D., Piomelli D., and Hohmann A.G. Role of the basolateral nucleus of the amygdala in endocannabinoid-mediated stress-induced analgesia. Neurosci Lett 397 (2006) 180-184
278. Maione S., Bisogno T., de Novellis V., Palazzo E., Cristino L., Valenti M., et al. Elevation of endocannabinoid levels in the ventrolateral periaqueductal grey through inhibition of fatty acid amide hydrolase affects descending nociceptive pathways via both CB1 and TRPV1 receptors. J Pharmacol Exp Ther 316 (2006) 969-982
279. Di Marzo V., and Matias I. Endocannabinoid control of food intake and energy balance. Nat Neurosci 8 (2005) 585-589
280. Williams C.M., and Kirkham T.C. Anandamide induces overeating: mediation by central cannabinoid (CB1) receptors. Psychopharmacology (Berl) 143 (1999) 315-317
281. Hao S., Avraham Y., Mechoulam R., and Berry E.M. Low dose anandamide affects food intake, cognitive function, neurotransmitter and corticosterone levels in diet-restricted mice. Eur J Pharmacol 392 (2000) 147-156
282. Jamshidi N., and Taylor D.A. Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats. Br J Pharmacol 134 (2001) 1151-1154
283. Di Marzo V., Goparaju S.K., Wang L., Liu J., Batkai S., Jarai Z., et al. Leptin-regulated endocannabinoids are involved in maintaining food intake. Nature 410 (2001) 822-825
284. Maccarrone M., Fride E., Bisogno T., Bari M., Cascio M.G., Battista N., et al. Up-regulation of the endocannabinoid system in the uterus of leptin knockout (ob/ob) mice and implications for fertility. Mol Hum Reprod 11 (2005) 21-28
285. Gomez 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
286. 9-tetrahydrocannabinol, anandamide, 2-arachidonoyl glycerol and SR141716. Psychopharmacology (Berl) 165 (2003) 370-377
287. Soderstrom K., Tian Q., Valenti M., and Di Marzo V. Endocannabinoids link feeding state and auditory perception-related gene expression. J Neurosci 24 (2004) 10013-10021
288. Monteleone P., Matias I., Martiadis V., De Petrocellis L., Maj M., and Di Marzo V. Blood levels of the endocannabinoid anandamide are increased in anorexia nervosa and in binge-eating disorder, but not in bulimia nervosa. Neuropsychopharmacology 30 (2005) 1216-1221
289. Fride E., Ginzburg Y., Breuer A., Bisogno T., Di Marzo V., and Mechoulam R. Critical role of the endogenous cannabinoid system in mouse pup suckling and growth. Eur J Pharmacol 419 (2001) 207-214
290. Fride E., Foox A., Rosenberg E., Faigenboim M., Cohen V., Barda L., et al. Milk intake and survival in newborn cannabinoid CB1 receptor knockout mice: evidence for a "CB3" receptor. Eur J Pharmacol 461 (2003) 27-34
291. Ben-Shabat S., Fride E., Sheskin T., Tamiri T., Rhee M.H., Vogel Z., et al. An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 353 (1998) 23-31
292. Cota D., Marsicano G., Tschop M., Grubler 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
293. Kirkham T.C. Endocannabinoids in the regulation of appetite and body weight. Behav Pharmacol 16 (2005) 297-313
294. Ravinet Trillou C., Arnone M., Delgorge C., Gonalons N., Keane P., Maffrand J.P., et al. Anti-obesity effect of SR141716, a CB1 receptor antagonist, in diet-induced obese mice. Am J Physiol Regul Integr Comp Physiol 284 (2003) R345-R353
295. Cooper S.J. Endocannabinoids and food consumption: comparisons with benzodiazepine and opioid palatability-dependent appetite. Eur J Pharmacol 500 (2004) 37-49
296. Darmani N.A. Endocannabinoids and gastrointestinal function. In: Onaivi E.S., Sugiura T., and Di Marzo V. (Eds). Endocannabinoids: The brain and body's marijuana and beyond (2006), Taylor & Francis, Boca Raton 395-419
297. Darmani N.A., McClanahan B.A., Trinh C., Petrosino S., Valenti M., and Di Marzo V. Cisplatin increases brain 2-arachidonoylglycerol (2-AG) and concomitantly reduces intestinal 2-AG and anandamide levels in the least shrew. Neuropharmacology 49 (2005) 502-513
298. Navarro M., Hernandez E., Munoz R.M., del Arco I., Villanua M.A., Carrera M.R., et al. Acute administration of the CB1 cannabinoid receptor antagonist SR 141716A induces anxiety-like responses in the rat. Neuroreport 8 (1997) 491-496
299. Patel S., Roelke C.T., Rademacher D.J., Cullinan W.E., and Hillard C.J. Endocannabinoid signaling negatively modulates stress-induced activation of the hypothalamic-pituitary-adrenal axis. Endocrinology 145 (2004) 5431-5438
300. Hill M.N., Patel S., Carrier E.J., Rademacher D.J., Ormerod B.K., Hillard C.J., et al. Downregulation of endocannabinoid signaling in the hippocampus following chronic unpredictable stress. Neuropsychopharmacology 30 (2005) 508-515
301. Patel S., Roelke C.T., Rademacher D.J., and Hillard C.J. Inhibition of restraint stress-induced neural and behavioural activation by endogenous cannabinoid signalling. Eur J Neurosci 21 (2005) 1057-1069
302. Wang L., Liu J., Harvey-White J., Zimmer A., and Kunos G. Endocannabinoid signaling via cannabinoid receptor 1 is involved in ethanol preference and its age-dependent decline in mice. Proc Natl Acad Sci USA 100 (2003) 1393-1398
303. Piomelli D. The endogenous cannabinoid system and the treatment of marijuana dependence. Neuropharmacology 47 (2004) 359-367
304. Basavarajappa B.S., and Hungund B.L. Neuromodulatory role of the endocannabinoid signaling system in alcoholism: an overview. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 287-299
305. Hungund B.L., Szakall I., Adam A., Basavarajappa B.S., and Vadasz C. Cannabinoid CB1 receptor knockout mice exhibit markedly reduced voluntary alcohol consumption and lack alcohol-induced dopamine release in the nucleus accumbens. J Neurochem 84 (2003) 698-704
306. Yamaguchi T., Hagiwara Y., Tanaka H., Sugiura T., Waku K., Shoyama Y., et al. Endogenous cannabinoid, 2-arachidonoylglycerol, attenuates naloxone-precipitated withdrawal signs in morphine-dependent mice. Brain Res 909 (2001) 121-126
307. Galiegue S., Mary S., Marchand J., Dussossoy D., Carriere D., Carayon P., et al. Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem 232 (1995) 54-61
308. Skaper S.D., Buriani A., Dal Toso R., Petrelli L., Romanello S., Facci L., et al. The ALIAmide palmitoylethanolamide and cannabinoids, but not anandamide, are protective in a delayed postglutamate paradigm of excitotoxic death in cerebellar granule neurons. Proc Natl Acad Sci USA 93 (1996) 3984-3989
309. Sinha D., Bonner T.I., Bhat N.R., and Matsuda L.A. Expression of the CB1 cannabinoid receptor in macrophage-like cells from brain tissue: immunochemical characterization by fusion protein antibodies. J Neuroimmunol 82 (1998) 13-21
310. Matias I., Pochard P., Orlando P., Salzet M., Pestel J., and Di Marzo V. Presence and regulation of the endocannabinoid system in human dendritic cells. Eur J Biochem 269 (2002) 3771-3778
311. Cabral G.A. Marijuana and cannabinoid effects in immunity and AIDS. In: Onaivi E.S. (Ed). Biology of marijuana (2002), Tayler & Francis, London 82-307
312. Klein T.W., Newton C., Larsen K., Lu L., Perkins I., Nong L., et al. The cannabinoid system and immune modulation. J Leukoc Biol 74 (2003) 486-496
313. Parolaro D., Massi P., Rubino T., and Monti E. Endocannabinoids in the immune system and cancer. Prostaglandins Leukot Essent Fatty Acids 66 (2002) 319-332
314. Berdyshev E.V. Endocannabinoids in inflammation and immune response. In: Onaivi E.S., Sugiura T., and Di Marzo V. (Eds). Endocannabinoids: The brain and body's marijuana and beyond (2006), Taylor & Francis, Boca Raton 431-450
315. Facchinetti F., Del Giudice E., Furegato S., Passarotto M., and Leon A. Cannabinoids ablate release of TNFα in rat microglial cells stimulated with lypopolysaccharide. Glia 41 (2003) 161-168
316. Jbilo O., Derocq J.M., Segui M., Le Fur G., and Casellas P. Stimulation of peripheral cannabinoid receptor CB2 induces MCP-1 and IL-8 gene expression in human promyelocytic cell line HL60. FEBS Lett 448 (1999) 273-277
317. Rayman N., Lam K.H., Laman J.D., Simons P.J., Lowenberg B., Sonneveld P., et al. Distinct expression profiles of the peripheral cannabinoid receptor in lymphoid tissues depending on receptor activation status. J Immunol 172 (2004) 2111-2117
318. Iwamura H., Suzuki H., Ueda Y., Kaya T., and Inaba T. In vitro and in vivo pharmacological characterization of JTE-907, a novel selective ligand for cannabinoid CB2 receptor. J Pharmacol Exp Ther 296 (2001) 420-425
319. Ueda Y., Miyagawa N., Matsui T., Kaya T., and Iwamura H. Involvement of cannabinoid CB2 receptor-mediated response and efficacy of cannabinoid CB2 receptor inverse agonist, JTE-907, in cutaneous inflammation in mice. Eur J Pharmacol 520 (2005) 164-171
320. Jan T.R., Farraj A.K., Harkema J.R., and Kaminski N.E. Attenuation of the ovalbumin-induced allergic airway response by cannabinoid treatment in A/J mice. Toxicol Appl Pharmacol 188 (2003) 24-35
321. Buckley N.E., McCoy K.L., Mezey E., Bonner T., Zimmer A., Felder C.C., et al. Immunomodulation by cannabinoids is absent in mice deficient for the cannabinoid CB2 receptor. Eur J Pharmacol 396 (2000) 141-149
322. 9-tetrahydrocannabinol (THC). J Pharmacol Exp Ther 186 (1973) 646-655
323. 9-tetrahydrocannabinol antagonizes the peripheral cannabinoid receptor-mediated inhibition of adenylyl cyclase. J Biol Chem 271 (1996) 9902-9905
324. Smith S.R., Denhardt G., and Terminelli C. The anti-inflammatory activities of cannabinoid receptor ligands in mouse peritonitis models. Eur J Pharmacol 432 (2001) 107-119
325. Hanus L., Breuer A., Tchilibon S., Shiloah S., Goldenberg D., Horowitz M., et al. HU-308: a specific agonist for CB2, a peripheral cannabinoid receptor. Proc Natl Acad Sci USA 96 (1999) 14228-14233
326. Clayton N., Marshall F.H., Bountra C., and O'Shaughnessy C.T. CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain. Pain 96 (2002) 253-260
327. Conti S., Costa B., Colleoni M., Parolaro D., and Giagnoni G. Antiinflammatory action of endocannabinoid palmitoylethanolamide and the synthetic cannabinoid nabilone in a model of acute inflammation in the rat. Br J Pharmacol 135 (2002) 181-187
328. Oka S, Wakui J, Gokoh M, Kishimoto S, Sugiura T. Suppression by WIN55212-2, a cannabinoid receptor agonist, of inflammatory reactions in mouse ear: interference with the actions of an endogenous ligand, 2-arachidonoylglycerol. Eur J Pharmacol [in press].
329. Randall M.D., Harris D., and Kendall D.A. The vascular pharmacology of endocannabinoids. In: Onaivi E.S. (Ed). Biology of marijuana (2002), Tayler & Francis, London 542-543
330. Pacher P., Batkai S., and Kunos G. Cardiovascular pharmacology of cannabinoids. In: Pertwee R.G. (Ed). Cannabinoids (2004), Springer, Berlin 599-625
331. Deutsch D.G., Goligorsky M.S., Schmid P.C., Krebsbach R.J., Schmid H.H.O., Das S.K., et al. Production and physiological actions of anandamide in the vasculature of the rat kidney. J Clin Invest 100 (1997) 1538-1546
332. Chen Y., McCarron R.M., Ohara Y., Bembry J., Azzam N., Lenz F.A., et al. Human brain capillary endothelium: 2-arachidonoglycerol (endocannabinoid) interacts with endothelin-1. Circ Res 87 (2000) 323-327
333. Kurihara J., Nishigaki M., Suzuki S., Okubo Y., Takata Y., Nakane S., et al. 2-Arachidonoylglycerol and anandamide oppositely modulate norepinephrine release from the rat heart sympathetic nerves. Jpn J Pharmacol 87 (2001) 93-96
334. Randall M.D., Alexander S.P., Bennett T., Boyd E.A., Fry J.R., Gardiner S.M., et al. An endogenous cannabinoid as an endothelium-derived vasorelaxant. Biochem Biophys Res Commun 229 (1996) 114-120
335. White R., and Hiley C.R. A comparison of EDHF-mediated and anandamide-induced relaxations in the rat isolated mesenteric artery. Br J Pharmacol 122 (1997) 1573-1584
336. Fulton D., and Quilley J. Evidence against anandamide as the hyperpolarizing factor mediating the nitric oxide-independent coronary vasodilator effect of bradykinin in the rat. J Pharmacol Exp Ther 286 (1998) 1146-1151
337. Chataigneau T., Feletou M., Thollon C., Villeneuve N., Vilaine J.P., Duhault J., et al. Cannabinoid CB1 receptor and endothelium-dependent hyperpolarization in guinea-pig carotid, rat mesenteric and porcine coronary arteries. Br J Pharmacol 123 (1998) 968-974
338. Jarai Z., Wagner J.A., Varga K., Lake K.D., Compton D.R., Martin B.R., et al. Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors. Proc Natl Acad Sci USA 96 (1999) 14136-14141
339. Wagner J.A., Varga K., Jarai Z., and Kunos G. Mesenteric vasodilation mediated by endothelial anandamide receptors. Hypertension 33 (1999) 429-434
340. Duncan M., Millns P., Smart D., Wright J.E., Kendall D.A., and Ralevic V. Noladin ether, a putative endocannabinoid, attenuates sensory neurotransmission in the rat isolated mesenteric arterial bed via a non-CB1/CB2 Gi/o linked receptor. Br J Pharmacol 142 (2004) 509-518
341. Wagner J.A., Hu K., Bauersachs J., Karcher J., Wiesler M., Goparaju S.K., et al. Endogenous cannabinoids mediate hypotension after experimental myocardial infarction. J Am Coll Cardiol 38 (2001) 2048-2054
342. Bouchard J.F., Lepicier P., and Lamontagne D. Contribution of endocannabinoids in the endothelial protection afforded by ischemic preconditioning in the isolated rat heart. Life Sci 72 (2003) 1859-1870
343. Lepicier P., Bouchard J.F., Lagneux C., and Lamontagne D. Endocannabinoids protect the rat isolated heart against ischaemia. Br J Pharmacol 139 (2003) 805-815
344. Kurabayashi M., Takeyoshi I., Yoshinari D., Matsumoto K., Maruyama I., and Morishita Y. 2-Arachidonoylglycerol increases in ischemia-reperfusion injury of the rat liver. J Invest Surg 18 (2005) 25-31
345. Pate D.W., Jarvinen K., Urtti A., Jarho P., and Jarvinen T. Ophthalmic arachidonylethanolamide decreases intraocular pressure in normotensive rabbits. Curr Eye Res 14 (1995) 791-797
346. Mikawa Y., Matsuda S., Kanagawa T., Tajika T., Ueda N., and Mimura Y. Ocular activity of topically administered anandamide in the rabbit. Jpn J Ophthalmol 41 (1997) 217-220
347. Laine K., Jarvinen K., Mechoulam R., Breuer A., and Jarvinen T. Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid. Invest Ophthalmol Vis Sci 43 (2002) 3216-3222
348. Chen J., Matias I., Dinh T., Lu T., Venezia S., Nieves A., et al. Finding of endocannabinoids in human eye tissues: implications for glaucoma. Biochem Biophys Res Commun 330 (2005) 1062-1067
349. Harada N., Nemoto K., Okamura T., Ninomiya N., Suzuki H., and Yamamoto Y. Effects of cannabinoids on colonic muscle contractility and tension in guinea pigs. J Nippon Med Sch (2005) 43-51
350. Fowler C.J., Jonsson K.O., Andersson A., Juntunen J., Jarvinen T., Vandevoorde S., et al. Inhibition of C6 glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: variability in response and involvement of arachidonic acid. Biochem Pharmacol 66 (2003) 757-767
351. Fowler C.J., Jonsson K.O., Andersson A., Juntunen J., Jarvinen T., Vandevoorde S., et al. Inhibition of C6 glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: variability in response and involvement of arachidonic acid. Biochem Pharmacol 66 (2003) 757-767
352. Valk P.J., Hol S., Vankan Y., Ihle J.N., Askew D., Jenkins N.A., et al. The genes encoding the peripheral cannabinoid receptor and alpha-l-fucosidase are located near a newly identified common virus integration site, Evi11. J Virol 71 (1997) 6796-6804
353. Jorda M.A., Lowenberg B., and Delwel R. The peripheral cannabinoid receptor Cb2, a novel oncoprotein, induces a reversible block in neutrophilic differentiation. Blood 101 (2003) 1336-1343
354. Alberich Jorda M., Rayman N., Tas M., Verbakel S.E., Battista N., van Lom K., et al. The peripheral cannabinoid receptor Cb2, frequently expressed on AML blasts, either induces a neutrophilic differentiation block or confers abnormal migration properties in a ligand-dependent manner. Blood 104 (2004) 526-534