Alternative pathways of anandamide biosynthesis in rat testes

Chemistry and Physics of Lipids

Volumn 92, Issue 1, 1998, Pages 27-35

  Schmid, Patricia C ^a   Schwindenhammer, Dana ^a   Krebsbach, Randy J ^a   Schmid, Harald H O ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Anandamide; Biosynthesis; N Acyl PE; N acylethanolamine; Rat testes

Indexed keywords

ANANDAMIDE; ARACHIDONIC ACID; CALCIUM ION; EGTAZIC ACID; ETHANOLAMINE; PHOSPHATIDYLETHANOLAMINE;

ANIMAL TISSUE; ARTICLE; BIOSYNTHESIS; MALE; MEMBRANE; NONHUMAN; PRIORITY JOURNAL; RAT; TESTIS;

ANIMALIA;

EID: 0031806881     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(97)00109-6     Document Type: Article

References (40)

1. Bartlett G.R. Phosphorus assay in column chromatography. J. Biol. Chem. 234:1959;466-468.
2. Bisogno T., Maurelli S., Melck D., De Petrocellis L., Di Marzo V. Biosynthesis, uptake and degradation of anandamide and palmitoylethanolamide in leukocytes. J. Biol. Chem. 272:1997;3315-3323.
3. Cadas H., di Tomaso E., Piomelli D. Occurrence and biosynthesis of endogenous cannabinoid precursor, N-arachidonyl phosphatidylethanolamine, in rat brain. J. Neurosci. 17:1997;1226-1242.
4. Cadas H., Gaillet S., Beltramo M., Venance L., Piomelli D. Biosynthesis of an endogenous cannabinoid precursor in neurons and its control by calcium and cAMP. J. Neurosci. 16:1996;3934-3942.
5. Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., Gilula N.B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature. 384:1996;83-87.
6. Das S.K., Paria B.C., Chakraborty I., Dey S.K. Cannabinoid ligand-receptor signaling in the mouse uterus. Proc. Natl. Acad. Sci. USA. 92:1995;4332-4336.
7. De Petrocellis L., Melck D., Ueda N., Maurelli S., Kurahashi Y., Yamamoto S., Marino G., Di Marzo V. Novel inhibitors of brain, neuronal and basophilic anandamide amidohydrolase. Biochem. Biophys. Res. Commun. 231:1997;82-88.
8. Desarnaud F., Cadas H., Piomelli D. Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization. J. Biol. Chem. 270:1995;6030-6035.
9. Deutsch D.G., Omeir R., Arreaza G., Salehani D., Prestwich G.D., Huang Z., Howlett A. Methyl arachidonyl fluorophosphonate: A potent irreversible inhibitor of anandamide amidase. Biochem. Pharmacol. 53:1997;255-260.
10. Devane W.A., Axelrod J. Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain membranes. Proc. Natl. Acad. Sci. USA. 91:1994;6698-6701.
11. 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. 258:1992;1946-1949.
12. 18 neuroblastoma cells. Biochem. J. 316:1996;977-984.
13. Di Marzo V., Fontana A., Cadas H., Schinelli S., Cimino G., Schwartz J-C., Piomelli D. Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature. 372:1994;686-691.
14. 2+ release from mitochondria by N-acylethanolamines, a class of lipids synthesized in ischemic heart tissue. J. Biol. Chem. 257:1982;1383-1391.
15. Felder C.C., Briley E.M., Axelrod J., Simpson J.T., Mackie K., Devane W.A. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA. 90:1993;7656-7660.
16. Folch J., Lees M., Sloane Stanley G.M. A simple method for the isolation and purification of lipids from animal tissue. J. Biol. Chem. 226:1957;497-507.
17. Gerard C.M., Mollereau C., Vassart G., Parmentier M. Molecular cloning of a human cannabinoid receptor which is also expressed in testis. Biochem. J. 279:1991;129-134.
18. Hansen H.S., Lauritzen L., Strand A.M., Moesgaard B., Frandsen A. Glutamate stimulates the formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cortical neurons in culture. Biochim. Biophys. Acta. 1258:1995;303-308.
19. Hansen H.S., Lauritzen L., Strand A.M., Vinggaard A.M., Frandsen A., Schousboe A. Characterization of glutamate-induced formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cultured neocortical neurons. J. Neurochem. 69:1997;753-761.
20. Katayama K., Ueda N., Kurahashi Y., Suzuki H., Yamamoto S., Kato I. Distribution of anandamide amidohydrolase in rat tissues with special reference to small intestine. Biochim. Biophys. Acta. 1347:1997;212-218.
21. Kruszka K.K., Gross R.W. The ATP- and CoA-independent synthesis of arachidonylethanolamide. A novel mechanism underlying the synthesis of the endogenous ligand of the cannabinoid receptor. J. Biol. Chem. 269:1994;14345-14348.
22. Kuwae T., Schmid P.C., Johnson S.B., Schmid H.H.O. Differential turnover of phospholipid acyl groups in mouse peritoneal macrophages. J. Biol. Chem. 265:1990;5002-5007.
23. 18O exchange catalyzed by pancreatic carboxylester lipase. 1. Mechanism and kinetic properties. Biochemistry. 31:1992;141-148.
24. Natarajan V., Reddy P.V., Schmid P.C., Schmid H.H.O. N-Acylation of ethanolamine phospholipids in canine myocardium. Biochim. Biophys. Acta. 712:1982;342-355.
25. Natarajan V., Schmid P.C., Reddy P.V., Schmid H.H.O. Catabolism of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 42:1984;1613-1619.
26. Paria B.C., Das S.K., Dey S.K. The pre-implantation mouse embryo is a target for cannabinoid ligand-receptor signaling. Proc. Natl. Acad. Sci. USA. 92:1995;9460-9464.
27. Schmid, P.C., Krebsbach, R.J., Perry, S.R., Dettmer, T.M., Maassen, J.L., Schmid, H.H.O., 1995. Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain, FEBS Lett. 375, 117-120;
28. Schmid, P.C., Krebsbach, R.J., Perry, S.R., Dettmer, T.M., Maassen, J.L., Schmid, H.H.O., 1995. Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain, FEBS Lett. 375, 117-120; Corrigendum 385 (1996) 125-126.
29. Schmid P.C., Kuwae T., Krebsbach R.J., Schmid H.H.O. Anandamide and other N-acylethanolamines in mouse peritoneal macrophages. Chem. Phys. Lipids. 87:1997a;103-110.
30. Schmid P.C., Paria B.C., Krebsbach R.J., Schmid H.H.O., Dey S.K. Changes in anandamide levels in mouse uterus are associated with uterine receptivity for embryo implantation. Proc. Natl. Acad. Sci. USA. 94:1997b;4188-4192.
31. Schmid P.C., Reddy P.V., Natarajan V., Schmid H.H.O. Metabolism of N-acylethanolamine phospholipids by a mammalian phosphodiesterase of the phospholipase D type. J. Biol. Chem. 258:1983;9302-9306.
32. Schmid P.C., Schmid H.H.O. N-acylation of ethanolamine phospholipids does not involve hydrolysis. Biochim. Biophys. Acta. 922:1987;398-400.
33. Schmid P.C., Schmid H.H.O. Reactions of diazomethane with glycerolipids in the presence of serum or inorganic salts. Lipids. 29:1994;883-887.
34. Schmid H.H.O., Schmid P.C., Natarajan V. N-acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29:1990;1-43.
35. Schmid H.H.O., Schmid P.C., Natarajan V. The N-acylation-phosphodiesterase pathway and cell signalling. Chem. Phys. Lipids. 80:1996;133-142.
36. Schmid P.C., Zuzarte-Augustin M.L, Schmid H.H.O. Properties of rat liver N-acylethanolamine amidohydrolase. J. Biol. Chem. 260:1985;14145-14149.
37. Skaper S.D., Buriani A., Dal Toso R., Petrelli L., Romanello S., Facci L., Leon A. 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.
38. Sugiura T., Kondo S., Sukagawa A., Tonegawa T., Nakane S., Yamashita A., Ishima Y., Waku K. 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. 240:1996a;53-62.
39. 2+-dependent transacylase and phosphodiesterase activities. Biochem. Biophys. Res. Commun. 218:1996b;113-117.
40. Ueda N., Kurahashi Y., Yamamoto S., Tokunaga T. Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J. Biol. Chem. 270:1995;23823-23827.