New perspectives in the studies on endocannabinoid and cannabis: 2-Arachidonoylglycerol as a possible novel mediator of inflammation

Journal of Pharmacological Sciences

Volumn 96, Issue 4, 2004, Pages 367-375

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

^a Teikyo University   (Japan)

Author keywords

2 Arachidonoylglycerol; Anandamide; Cannabinoid; Inflammation; 9 tetrahydrocannabinol

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; ANANDAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABIS; DRONABINOL; ENDOCANNABINOID; LIGAND; MITOGEN ACTIVATED PROTEIN KINASE; PHORBOL 13 ACETATE 12 MYRISTATE; RIMONABANT; STRESS ACTIVATED PROTEIN KINASE;

CELL DIFFERENTIATION; CELL MIGRATION; DRUG ABUSE; DRUG RECEPTOR BINDING; GENE REARRANGEMENT; IMMUNE SYSTEM; IMMUNOCOMPETENT CELL; INFLAMMATION; INFLAMMATORY CELL; MEDIATOR RELEASE; NATURAL KILLER CELL; NONHUMAN; SHORT SURVEY; SHORT TERM MEMORY; SYNAPTIC TRANSMISSION;

EID: 12444270066     PISSN: 13478613     EISSN: None     Source Type: Journal    
DOI: 10.1254/jphs.FMJ04003X3     Document Type: Short Survey

References (56)

1. Dewey WL. Cannabinoid pharmacology. Pharmacol Rev. 1986;38:151-178.
2. Devane WA, Dysarz FA III, Johnson MR, Melvin LS, Hewlett AC. Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol. 1988;34:605-613.
3. Matsuda LA, Lolait SJ, Brownstein MJ, Young AC, Bonner TI. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature. 1990;346:561-564.
4. Munro S, Thomas KL, Abu-Shaar M. Molecular characterization of a peripheral receptor for cannabinoids. Nature. 1993;365:61-65.
5. Schlicker E, Kathmann M. Modulation of transmitter release via presynaptic cannabinoid receptors. Trends Pharmacol Sci. 2001;22:565-572.
6. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 1992;258:1946-1949.
7. Di Marzo V, De Petrocellis L, Bisogno T, Berger A, Mechoulam R. Biology of endocannabinoids. In: Onaivi ES, editor. Biology of Marijuana. London: Taylor & Francis; 2002. p. 125-173.
8. Hansen HS, Moesgaard B, Hansen HH, Petersen G. N-Acylethanolamines and precursor phospholipids-relation to cell injury. Chem Phys Lipids. 2000;108:135-150.
9. Sugiura T, Kobayashi Y, Oka S, Waku K. Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological significance. Prostaglandins Leukot Essent Fatty Acids. 2002;66:173-192.
10. Schmid HHO, Schmid PC, Berdyshev EV. Cell signaling by endocannabinoids and their congeners: questions of selectivity and other challenges. Chem Phys Lipids. 2002;121:111-134.
11. 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. 1995;215:89-97.
12. Mechoulam R, Ben-Shabat S, Hanus L, Ligumsky M, Kaminski NE, Schatz AR, et al. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol. 1995;50:83-90.
13. Sugiura T, Waku K. 2-Arachidonoylglycerol and the cannabinoid receptors. Chem Phys Lipids. 2000;108:89-106.
14. Prescott SM, Majerus PW. Characterization of 1,2-diacylglycerol hydrolysis in human platelets. Demonstration of an arachidonoyl-monoacylglycerol intermediate. J Biol Chem. 1983;258:764-769.
15. Stella N, Schweitzer P, Piomelli D. A second endogenous cannabinoid that modulates long-term potentiation. Nature. 1997;388:773-778.
16. 2+ in neuroblastoma × glioma hybrid NG108-15 cells. Biochem Biophys Res Commun. 1996;229:58-64.
17. 1 receptor is a 2- arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem. 1999;274:2794-2801.
18. 2 receptor. Comparison of the agonistic activities of various cannabinoid receptor ligands in HL-60 cells. J Biol Chem. 2000;275:605-612.
19. Hillard CJ. Biochemistry and pharmacology of the endocannabinoids arachidonylethanolamide and 2-arachidonylglycerol. Prostaglandins Other Lipid Mediat. 2000;61:3-18.
20. Gonsiorek W, Lunn C, Fan X, Narula S, Lundell D, Hipkin RW. Endocannabinoid 2-arachidonyl glycerol is a full agonist through human type 2 cannabinoid receptor: antagonism by anandamide. Mol Pharmacol. 2000;57:1045-1050.
21. Savinainen JR, Jarvinen T, Laine K, Laitinen JT. Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB(1) receptor-dependent G-protein activation in rat cerebellar membranes. Br J Pharmacol. 2001;134:664-672.
22. Porter AC, Sauer JM, Knierman MD, Becker GW, Berna MJ, Bao J, et al. Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J Pharmacol Exp Ther. 2002;301:1020-1024.
23. Huang SM, 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. 2002;99:8400-8405.
24. Hanus S, Abu-Lafi S, Fride E, Breuer A, Vogel Z, Shalev DE, et al. 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc Natl Acad Sci USA. 2001;98:3662-3665.
25. Fezza F, Bisogno T, Minassi A, Appendino G, Mechoulam R, Di Marzo V. Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues. FEBS Lett. 2002;513:294-298.
26. 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. 2003;85:1374-1381.
27. Lynn AB, Herkenham M. Localization of cannabinoid receptors and nonsaturable high-density cannabinoid binding sites in peripheral tissues of the rat: implications for receptor-mediated immune modulation by cannabinoids. J Pharmacol Exp Ther. 1994;268:1612-1623.
28. 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. 1995;232:54-61.
29. Facci L, Dal Toso R, Romanello S, Buriani A, Skaper SD, Leon A. Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide. Proc Natl Acad Sci USA. 1995;92:3376-3380.
30. Carlisle SJ, Marciano-Cabral F, Staab A, Ludwick C, Cabral GA. Differential expression of the CB2 cannabinoid receptor by rodent macrophages and macrophage-like cells in relation to cell activation. Int Immunopharmacol. 2002;2:69-82.
31. Matias I, Pochard P, Orlando P, Salzet M, Pestel J, Di Marzo V. Presence and regulation of the endocannabinoid system in human dendritic cells. Eur J Biochem. 2002;269:3771-3778.
32. 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. 2004;76:1002-1009.
33. Kobayashi Y, Arai S, Waku K, Sugiura T. Activation by 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand, of p42/44 mitogen-activated protein kinase in HL-60 cells. J Biochem. 2001;129:665-669.
34. Sugiura T, Kishimoto S, Oka S, Gokoh M, Waku K. Metabolism and physiological significance of anandamide and 2-arachidonoylglycerol, endogenous cannabinoid receptor ligands. In: Fonteh AN and Wykle RL, editors. Arachidonate remodeling and inflammation. Basel: Birkhauser Verlag; 2004. p. 211-237.
35. Derkinderen P, Ledent C, Parmentier M, Girault JA. Cannabinoids activate p38 mitogen-activated protein kinases through CB1 receptors in hippocampus. J Neurochem. 2001;77:957-960.
36. 1 cannabinoid receptor is coupled to the activation of c-Jun N-terminal kinase. Mol Pharmacol. 2000;58:814-820.
37. Dong C, Davis RJ, Flavell RA. MAP kinases in the immune response. Annu Rev Immunol. 2002;20:55-72.
38. Kishimoto S, Kobayashi Y, Oka S, Gokoh M, Waku K, Sugiura T. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells. J Biochem. 2004;135,517-524.
39. Jbilo O, Derocq JM, Segui M, Le Fur G, Casellas P. Stimulation of peripheral cannabinoid receptor CB2 induces MCP-1 and IL-8 gene expression in human promyelocytic cell line HL60. FEBS Lett. 1999;448:273-277.
40. Chang YH, Lee ST, Lin WW. Effects of cannabinoids on LPS-stimulated inflammatory mediator release from macrophages: involvement of eicosanoids. J Cell Biochem. 2001;81:715-723.
41. Gallily R, Breuer A, Mechoulam R. 2-Arachidonylglycerol, an endogenous cannabinoid, inhibits tumor necrosis factor-α production in murine macrophages, and in mice. Eur J Pharmacol. 2000;406:R5-R7.
42. 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. In press 2005.
43. 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. 2003;278:24469-24475.
44. Jorda MA, Verbakel SE, Valk PJ, Vankan-Berkhoudt YV, Maccarrone M, Finazzi-Agro A, et al. Hematopoietic cells expressing the peripheral cannabinoid receptor migrate in response to the endocannabinoid 2-arachidonoylglycerol. Blood. 2002;99:2786-2793.
45. Walter L, Franklin A, Witting A, Wade C, Xie Y, Kunos G, et al. Nonpsychotropic cannabinoid receptors regulate microglial cell migration. J Neurosci. 2003;23:1398-1405.
46. Iwamura H, Suzuki H, Ueda Y, Kaya T, Inaba T. In vitro and in vivo pharmacological characterization of JTE-907, a novel selective ligand for cannabinoid CB2 receptor. J Pharmacol Exp Ther. 2001;296:420-425.
47. Sofia RD, Nalepa SD, Vassar HB, Knobloch LC. Comparative anti-phlogistic activity of delta 9-tetrahydrocannabinol, hydrocortisone and aspirin in various rat paw edema models. Life Sci. 1974;15:251-260.
48. Bayewitch M, Rhee MH, Avidor-Reiss T, Breuer A, Mechoulam R. (-)-Δ9-Tetrahydrocannabinol antagonizes the peripheral cannabinoid receptor-mediated inhibition of adenylyl cyclase. J Biol Chem. 1996;271:9902-9905.
49. Berdyshev E, Boichot E, Corbel M, Germain N, Lagente V. Effects of cannabinoid receptor ligands on LPS-induced pulmonary inflammation in mice. Life Sci. 1998;63:PL125-PL129.
50. Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, et al. HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor. Proc Natl Acad Sci USA. 1999;96:14228-14233.
51. Smith SR, Denhardt G, Terminelli C. The anti-inflammatory activities of cannabinoid receptor ligands in mouse peritonitis models. Eur J Pharmacol. 2001;432:107-119.
52. Massa F, Marsicano G, Hermann H, Cannich A, Monory K, Cravatt BF, et al. The endogenous cannabinoid system protects against colonic inflammation. J Clin Invest. 2004;113:1202-1209.
53. Bisogno T, Sepe N, Melck D, Maurelli S, De Petrocellis L, Di Marzo V. Biosynthesis, release and degradation of the novel endogenous cannabimimetic metabolite 2-arachidonoylglycerol in mouse neuroblastoma cells. Biochem J. 1997;322:671-677.
54. Varga K, Wagner JA, Bridgen DT, Kunos G. Platelet- and macrophage-derived endogenous cannabinoids are involved in endotoxin-induced hypotension. FASEB J. 1998;12:1035-1044.
55. Di Marzo V, Bisogno T, De Petrocellis L, Melck D, Orlando P, Wagner JA, et al. Biosynthesis and inactivation of the endocannabinoid 2- arachidonoylglycerol in circulating and tumoral macrophages. Eur J Biochem. 1999;264:258-267.
56. Berdyshev EV, Schmid PC, Krebsbach RJ, Schmid HHO. Activation of PAF receptors results in enhanced synthesis of 2-arachidonoylglycerol (2-AG) in immune cells. FASEB J. 2001;15:2171-2178.