Brain Molecules and Appetite: The Case of Oleoylethanolamide

Central Nervous System Agents in Medicinal Chemistry

Volumn 13, Issue 1, 2013, Pages 88-91

  Sarro Ramírez, Andrea ^a   Sánchez López, Daniel ^a   Tejeda Padrón, Alma ^a   Frías, Carmen ^a   Zaldívar Rae, Jaime ^a   Murillo Rodríguez, Eric ^a  

^a Universidad del Mayab   (Mexico)

Author keywords

Anorexia; Central nervous system; Endocannabinoids; Feeding; Hypothalamus

Indexed keywords

ANANDAMIDE; CHOLECYSTOKININ; FATTY ACID AMIDASE; G PROTEIN COUPLED RECEPTOR; GHRELIN; LEPTIN; MELANIN CONCENTRATING HORMONE; MESSENGER RNA; N OLEOYLETHANOLAMINE; NEUROPEPTIDE Y; OREXIN; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PHOSPHATIDYLETHANOLAMINE; PROTEIN C FOS; VANILLOID RECEPTOR 1; VASOACTIVE INTESTINAL POLYPEPTIDE;

ANOREXIA; APPETITE; BIOCHEMISTRY; BIOSYNTHESIS; FAT INTAKE; HUMAN; LIPID METABOLISM; LIPOLYSIS; NONHUMAN; PROTEIN EXPRESSION; REVIEW; VAGUS NERVE;

ANIMALS; APPETITE; BRAIN; EATING; ENDOCANNABINOIDS; FEEDING BEHAVIOR; HUMANS; HYPOTHALAMUS; OLEIC ACIDS; SATIETY RESPONSE;

EID: 84875285085     PISSN: 18715249     EISSN: 18756166     Source Type: Journal    
DOI: 10.2174/1871524911313010010     Document Type: Review

References (46)

1. Devane, W.A.; Hanus, L.; Breuer, A.; Pertwee, R.G.; Stevenson, L.A.; Griffin, G.; Gibson, D.; Mandelbaum, A.; Etinger, A.; Mechoulam, R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science, 1992, 258(5090), 1946-1949.
2. Katona, I.; Freund, T.F. Multiple functions of endocannabinoid signaling in the brain. Annu. Rev. Neurosci., 2012, 35, 527-558.
3. Hansen, H.S. Palmitoylethanolamide and other anandamide congeners. Proposed role in the diseased brain. Exp. Neurol., 2010, 224(1), 48-55.
4. Vaughn, L.K.; Denning, G.; Stuhr, K.L.; de Wit, H.; Hill, M.N.; Hillard, C.J. Endocannabinoid signalling: has it got rhythm? Br. J. Pharmacol., 2010, 160(3), 530-543.
5. Wang, X.; Wang, X.; Wang, T. Synthesis of oleoylethanolamide using lipase. J. Agric. Food Chem., 2012, 60(1), 451-457.
6. Rodríguez de Fonseca, F.; Navarro, M.; Gómez, R.; Escuredo, L.; Nava, F.; Fu, J.; Murillo-Rodríguez, E.; Giuffrida, A.; Lo Verme, J.; Gaetani, S.; Kathuria, S.; Gall, C.; Piomelli, D. An anorexic lipid mediator regulated by feeding. Nature, 2001, 414(6860), 209-212.
7. Fu, J.; Astarita, G.; Gaetani, S.; Kim, J.; Cravatt, B.F.; Mackie, K.; Piomelli, D. Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine. J. Biol. Chem., 2007, 282(2), 1518-1528.
8. Lo Verme, J.; Gaetani, S.; Fu, J.; Oveisi, F.; Burton, K.; Piomelli, D. Regulation of food intake by oleoylethanolamide. Cell Mol. Life Sci., 2005, 62(6), 708-716.
9. Matias, I.; Gonthier, M.P.; Petrosino, S.; Docimo, L.; Capasso, R.; Hoareau, L.; Monteleone, P.; Roche, R.; Izzo, A.A.; Di Marzo, V. Role and regulation of acylethanolamides in energy balance: focus on adipocytes and beta-cells. Br. J. Pharmacol., 2007, 152(5), 676-690.
10. Thabuis, C.; Tissot-Favre, D.; Bezelgues, J.B.; Martin, J.C.; Cruz-Hernández, C.; Dionisi, F.; Destaillats, F. Biological functions and metabolism of oleoylethanolamide. Lipids, 2008, 43(10), 887-894.
11. Khanna, I.K.; Alexander, C.W. Fatty acid amide hydrolase inhibitors--progress and potential. CNS Neurol. Disord. Drug Targets, 2011, 10(5), 545-558.
12. Caprioli, A.; Coccurello, R.; Rapino, C.; Di Serio, S.; Di Tommaso, M.; Vertechy, M.; Vacca, V.; Battista, N.; Pavone, F.; Maccarrone, M.; Borsini, F. The novel reversible fatty acid amide hydrolase inhibitor ST4070 increases endocannabinoid brain levels and counteracts neuropathic pain in different animal models. J. Pharmacol. Exp. Ther., 2012, 342(1), 188-195.
13. Feledziak, M.; Lambert, D.M.; Marchand-Brynaert, J.; Muccioli, G.G. Inhibitors of the endocannabinoid-degrading enzymes, or how to increase endocannabinoid's activity by preventing their hydrolysis. Recent Pat. CNS Drug Discov., 2012, 7(1), 49-70.
14. Gaetani, S.; Oveisi, F.; Piomelli, D. Modulation of meal pattern in the rat by the anorexic lipid mediator oleoylethanolamide. Neuropsychopharmacol, 2003, 28(7), 1311-1316.
15. Mor, M.; Rivara, S.; Lodola, A.; Plazzi, P.V.; Tarzia, G.; Duranti, A.; Tontini, A.; Piersanti, G.; Kathuria, S.; Piomelli, D. Cyclohexylcarbamic acid 3'- or 4'- substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies. J. Med. Chem., 2004, 47(21), 4998-5008.
16. Tarzia, G.; Duranti, A.; Tontini, A.; Piersanti, G.; Mor, M.; Rivara, S.; Plazzi, P.V.; Park, C.; Kathuria, S.; Piomelli, D. Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors. J. Med. Chem., 2003, 46(12), 2352-2360.
17. Cippitelli, A.; Astarita, G.; Duranti, A.; Caprioli, G.; Ubaldi, M.; Stopponi, S.; Kallupi, M.; Sagratini, G.; Rodríguez de Fonseca, F.; Piomelli, D.; Ciccocioppo, R. Endocannabinoid regulation of acute and protracted nicotine withdrawal: effect of FAAH inhibition. PLoS One, 2011, 6, e2814.
18. Murillo-Rodríguez, E.; Palomero-Rivero, M.; Millán-Aldaco, D.; Arias-Carrión, O.; Drucker-Colín, R. Administration of URB597, Oleoylethanolamide or Palmitoylethanolamide increases waking and dopamine in rats. PLoS One, 2011, 6, e20766.
19. Murillo-Rodríguez, E.; Desarnaud, F.; Prospéro-García, O. Diurnal variation of arachidonoylethanolamine, palmitoylethanolamide and oleoylethanolamide in the brain of the rat. Life Sci., 2006, 79(1), 30-37.
20. Campolongo, P.; Roozendaal, B.; Trezza, V.; Cuomo, V.; Astarita, G.; Fu, J.; McGaugh, J.L.; Piomelli, D. Fat-induced satiety factor oleoylethanolamide enhances memory consolidation. Proc. Natl. Acad. Sci. U.S.A., 2009, 106(19), 8027-8031.
21. Hill, M.N.; Miller, G.E.; Carrier, E.J.; Gorzalka, B.B.; Hillard, C.J. Circulating endocannabinoids and N-acyl ethanolamines are differentially regulated in major depression and following exposure to social stress. Psychoneuroendocrinol, 2009, 34 (8), 1257-1262.
22. Murillo-Rodríguez, E.; Vázquez, E.; Millán-Aldaco, D.; Palomero-Rivero, M.; Drucker-Colín, R. Effects of the fatty acid amide hydrolase inhibitor URB597 on the sleep-wake cycle, c-Fos expression and dopamine levels of the rat. Eur. J. Pharmacol., 2007, 562(1-2), 82-91.
23. Lueneberg, K.; Domínguez, G.; Arias-Carrión, O.; Palomero-Rivero, M.; Millán-Aldaco, D.; Morán, J.; Drucker-Colín, R.; Murillo-Rodríguez, E. Cellular viability effects of fatty acid amide hydrolase inhibition on cerebellar neurons. Int. Arch. Med., 2011, 4(1), 28.
24. Koethe, D.; Schreiber, D.; Giuffrida, A.; Mauss, C.; Faulhaber, J.; Heydenreich, B.; Hellmich, M.; Graf, R.; Klosterkötter, J.; Piomelli, D.; Leweke, F.M. Sleep deprivation increases oleoylethanolamide in human cerebrospinal fluid. J. Neural. Transm., 2009, 116(3), 301-305.
25. Kaczocha, M.; Vivieca, S.; Sun, J.; Glaser, S.T.; Deutsch, D.G. Fatty acid-binding proteins transport N-acylethanolamines to nuclear receptors and are targets of endocannabinoid transport inhibitors. J. Biol. Chem., 2012, 287(5), 3415-3424.
26. Izzo, A.A.; Piscitelli, F.; Capasso, R.; Marini, P.; Cristino, L.; Petrosino, S.; Di Marzo, V. Basal and fasting/refeeding-regulated tissue levels of endogenous PPAR-alpha ligands in Zucker rats. Obesity, 2010, 18(1), 55-62.
27. Fu, J.; Dipatrizio, N.V.; Guijarro, A.; Schwartz, G.J.; Li, X.; Gaetani, S.; Astarita, G.; Piomelli, D. Sympathetic activity controls fat-induced oleoylethanolamide signaling in small intestine. J. Neurosci., 2011, 31(15), 5730-5736.
28. Schupp, M.; Lazar, M.A. Endogenous ligands for nuclear receptors: digging deeper. J. Biol. Chem., 2010, 285(52), 40409-40415.
29. Varga T, Czimmerer Z, Nagy L. PPARs are a unique set of fatty acid regulated transcription factors controlling both lipid metabolism and inflammation. Biochim. Biophys Acta., 2011, 1812(8), 1007-1022.
30. Fu, J.; Gaetani, S.; Oveisi, F.; Lo Verme, J.; Serrano, A.; Rodríguez de Fonseca, F.; Rosengarth, A.; Luecke, H.; Di Giacomo, B.; Tarzia, G.; Piomelli, D. Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-alpha. Nature, 2003, 425(6953), 90-93.
31. Aviello, G.; Matias, I.; Capasso, R.; Petrosino, S.; Borrelli, F.; Orlando, P.; Romano, B.; Capasso, F.; Di Marzo, V.; Izzo, A.A. Inhibitory effect of the anorexic compound oleoylethanolamide on gastric emptying in control and overweight mice. J. Mol. Med., 2008, 86(4), 413-422.
32. Gaetani, S.; Fu, J.; Cassano, T.; Dipasquale, P.; Romano, A.; Righetti, L.; Cianci, S.; Laconca, L.; Giannini, E.; Scaccianoce, S.; Mairesse, J.; Cuomo, V.; Piomelli, D. The fat-induced satiety factor oleoylethanolamide suppresses feeding through central release of oxytocin. J. Neurosci., 2010, 30(24), 8096-8101.
33. Serrano, A.; Pavón, F.J.; Tovar, S.; Casanueva, F.; Señarís, R.; Diéguez, C.; de Fonseca, F.R. Oleoylethanolamide: effects on hypothalamic transmitters and gut peptides regulating food intake. Neuropharmacology, 2011, 60(4), 593-601.
34. Yang, Y.; Chen, M.; Georgeson, K.E.; Harmon, C.M. Mechanism of oleoylethanolamide on fatty acid uptake in small intestine after food intake and body weight reduction. Am. J. Physiol. Reg. Int. Comp. Physiol., 2007, 292, R235-R341.
35. Matias, I.; Gatta-Cherifi, B.; Tabarin, A.; Clark, S.; Leste-Lasserre, T.; Marsicano, G.; Piazza, P.V.; Cota, D. Endocannabinoids measurement in human saliva as potential biomarker of obesity. PLoS One, 2012, 7, e42399.
36. Appendino, G.; Ligresti, A.; Minassi, A.; Cascio, M.G.; Allarà, M.; Taglialatela-Scafati, O.; Pertwee, R.G.; De Petrocellis, L.; Di Marzo, V. Conformationally constrained fatty acid ethanolamides as cannabinoid and vanilloid receptor probes. J. Med. Chem., 2009, 52(9), 3001-3009.
37. Godlewski, G.; Offertáler, L.; Wagner, J.A.; Kunos, G. Receptors for acylethanolamides-GPR55 and GPR119. Prostaglandins Other Lipid Mediat, 2009, 89(3-4), 105-111.
38. Hansen, H.S.; Rosenkilde, M.M.; Holst, J.J.; Schwartz, T.W. GPR119 as a fat sensor. Trends Pharmacol. Sci., 2012, 33(7), 374-381.
39. Benoit, S.C.; Tracy, A.L.; Davis, J.F.; Choi, D.; Clegg, D.J. Novel functions of orexigenic hypothalamic peptides: from genes to behavior. Nutrition, 2008, 24(9), 843-847.
40. Figlewicz, D.P.; Sipols, A.J. Energy regulatory signals and food reward. Pharmacol. Biochem. Behav., 2010, 97(1), 15-24.
41. Diéguez, C.; Vázquez, M.J.; Romero, A.; López, M.; Nogueiras, R. Hypothalamic control of lipid metabolism: focus on leptin, ghrelin and melanocortins. Neuroendocrinology, 2011, 94(1), 1-11.
42. Ghourab, S.; Beale, K.E.; Semjonous, N.M.; Simpson, K.A.; Martin, N.M.; Ghatei, M.A.; Bloom, S.R.; Smith, K.L. Intracerebroventricular administration of vasoactive intestinal peptide inhibits food intake. Regul. Pept., 2011, 172(1-3), 8-15.
43. Lateef, D.M.; Washington, M.C.; Sayegh, A.I. The short term satiety peptide cholecystokinin reduces meal size and prolongs intermeal interval. Peptides, 2011, 32(6), 1289-1295.
44. Tsuneki, H.; Wada, T.; Sasaoka, T. Role of orexin in the central regulation of glucose and energy homeostasis. Endocr. J., 2012, 59(5), 365-374.
45. Parker, J.A.; Bloom, S.R. Hypothalamic neuropeptides and the regulation of appetite. Neuropharmacol., 2012, 63(1), 18-30.
46. Matias, I.; Bisogno, T.; Di Marzo, V. Endogenous cannabinoids in the brain and peripheral tissues: regulation of their levels and control of food intake. Int. J. Obes. (Lond), 2006, SUPPL. 1:S7-S12.