The N-acylation-phosphodiesterase pathway and cell signalling

Chemistry and Physics of Lipids

Volumn 80, Issue 1-2, 1996, Pages 133-142

  Schmid, Harald H O ^a   Schmid, Patricia C ^a   Natarajan, Viswanathan ^b  

^a UNIVERSITY OF MINNESOTA   (United States)

^b INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Anandamide; Cannabinoid receptor; N acyl PE; N acylethanolamine; Phospholipase D; Signal transduction

Indexed keywords

AMIDASE; ANANDAMIDE; CANNABINOID RECEPTOR; ETHANOLAMINE; FATTY ACID; PHOSPHODIESTERASE; PHOSPHOLIPASE D;

ACYLATION; ANIMAL TISSUE; HYDROLYSIS; LIPID METABOLISM; NONHUMAN; PRIORITY JOURNAL; RECEPTOR BINDING; REVIEW; SIGNAL TRANSDUCTION;

EID: 0029931475     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-3084(96)02554-6     Document Type: Article

References (64)

1. M. Heller (1978) Phospholipase D. Adv. Lipid Res. 16, 267-326.
2. M. Waite (1987) The phospholipases, in: Handbook of Lipid Research, Plenum Press, New York.
3. M.M. Billah and J.C. Anthes (1990) The regulation and cellular functions of phosphatidylcholine hydrolysis. Biochem. J. 269, 281-291.
4. J. D. Lambeth (1994) Receptor-regulated phospholipases and their generation of lipid mediators which activate protein kinase C, in: J.F. Kuo (Ed.), Protein Kinase C, Oxford University Press, New York, pp. 121-170.
5. Z. Kiss and W.B. Anderson (1989) Phorbol ester stimulates the hydrolysis of phosphatidylethanolamine in leukemic HL-60, NIH-3T3, and baby hamster kidney cells. J. Biol. Chem. 264, 1483-1487.
6. H.H.O. Schmid, P.C. Schmid and V. Natarajan (1990) N-Acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29, 1-43.
7. F.A. Kuehl, Jr., T.A. Jacob, O.H. Ganley, R.E. Ormond and M.A.P. Meisinger (1957) The identification of N-(2-hydroxyethyl)-palmitamide as a naturally occurring anti-inflammatory agent. J. Am. Chem. Soc. 79, 5577-5578.
8. D.A. Long and A.J.P. Martin (1956) Factor in arachis oil depressing sensitivity to tuberculin in B.C.G-infected guinea pigs. Lancet I, 464-466.
9. O.H. Ganley, O.E. Graessle and H.J. Robinson (1957) Anti-inflammatory activity of compounds obtained from egg yolk, peanut oil, and soybean lecithin. J. Lab Clin. Med. 51, 709-714.
10. N.R. Bachur, K. Masek, K.L. Melmon and S. Udenfriend (1965) Fatty acid amides of ethanolamine in mammalian tissues. J. Biol. Chem. 240, 1019-1024.
11. D.E. Epps, P.C. Schmid, V. Natarajan and H.H.O. Schmid (1979) N-Acylethanolamine accumulation in infarcted myocardium. Biochem. Biophys. Res. Commun. 90, 628-633.
12. D.E. Epps, V. Natarajan, P.C. Schmid and H.H.O. Schmid (1980) Accumulation of N-acylethanolamine glycerophospholipids in infarcted myocardium. Biochim. Biophys. Acta 618, 420-430.
13. 2+ release from mitochondria by N-acylethanolamines, a class of lipids synthesized in ischemic heart tissue. J. Biol. Chem. 257, 1383-1391.
14. N.L. Parinandi and H.H.O. Schmid (1988) Effects of long-chain N-acylethanolamines on lipid peroxidation in cardiac mitochondria. FEBS Lett. 237, 49-52.
15. D.E. Epps and A.D. Cardin (1987) The interaction of N-oleylethanolamine with phospholipid bilayers. Biochim. Biophys. Acta 903, 533-541.
16. A. Ambrosini, E. Bertoli, P. Mariani, F. Tanfani, M. Wozniak and G. Zolese (1993) N-Acylethanolamines as membrane topological stress compromising agents. Biochim. Biophys. Acta 1148, 351-355.
17. A. Ambrosini, F. Tanfani, E. Bertoli, M. Wozniak, Z. Wypych and G. Zolese (1993) Effect of N-acylethanolamines with different acyl chains on DPPC multilamellar liposomes. Chem. Phys. Lipids 65, 165-169.
18. D.E. Epps, F. Mandel and A. Schwartz (1982) The alteration of rabbit skeletal sarcoplasmic reticulum function by N-acylethanolamine, a lipid associated with myocardial infarction. Cell Calcium 3, 531-543.
19. N.M. Gulaya, A.A. Melnik, D.I. Balkov, G.L. Volkov, M.V. Vysotskiy and V.E. Vaskovsky (1993) The effect of long-chain N-acylethanolamines on some membrane-associated functions of neuroblastoma C1300 N18 cells. Biochim. Biophys. Acta 1152, 280-288.
20. G.M. Gray (1976) Phosphatidyl-(N-acyl)-ethanolamine. A lipid component of mammalian epidermis. Biochim. Biophys. Acta 431, 1-8.
21. N.M. Gulaya, G.L. Volkov, V.M. Klimashevskii, N.N. Govseeva and A.A. Melnik (1989) Changes in lipid composition of neuroblastoma C1300 N18 cell during differentiation. Neuroscience 30, 153-164.
22. W.A. Devane, L. Hanus, A. Breuer, R.G. Pertwee, L.A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger and R. Mechoulam (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949.
23. L. Hanus, A. Gopher, S. Almog and R. Mechoulam (1993) Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J. Med. Chem. 36, 3032-3034.
24. Z. Vogel, J. Barg, R. Levy, D. Saya, E. Heldman and R. Mechoulam (1993) Anandamide, a brain endogenous compound, interacts specifically with cannabinoid receptors and inhibits adenylate cyclase. J. Neurochem. 61, 352-355.
25. K. Mackie, W.A. Devane and B. Hille (1993) Anandamide, an endogenous cannabinoid, inhibits calcium currents as a partial agonist in N18 neuroblastoma cells. Mol. Pharmacol. 44, 498-503.
26. L. Venance, D. Piomelli, J. Glowinski and C. Giaume (1995) Inhibition of anandamide of gap junctions and intercellular calcium signalling in striatal astrocytes. Nature 376, 590-594.
27. H. Schuel, E. Goldstein, R. Mechoulam, A.M. Zimmerman and S. Zimmerman (1994) Anandamide (arachidonoylethanolamide), a brain cannabinoid receptor agonist, reduces sperm fertilizing capacity in sea urchins by inhibiting the acrosome reaction. Proc. Natl. Acad. Sci. USA 91, 7678-7682.
28. S.K. Das, B.C. Paria, I. Chakraborty and S.K. Dey (1995) Cannabinoid ligand-receptor signaling in the mouse uterus. Proc. Natl. Acad. Sci. USA 92, 4332-4336.
29. B.C. Paria, S.K. Das and S.K. Dey (1995) The preimplantation mouse embryo is a target for cannabinoid ligand-receptor signaling. Proc. Natl. Acad. Sci. USA 92, 9460-9464.
30. V. Di Marzo, L. De Petrocellis, T. Bisogno and S. Maurelli (1995) Pharmacology and physiology of the endogenous cannabimimetic mediator anandamide (Review). J. Drug Dev. Clin. Pract. 7, 199-219.
31. V. Natarajan, P.V. Reddy, P.C. Schmid and H.H.O. Schmid (1981) On the biosynthesis and metabolism of N-acylethanolamine phospholipids in infarcted dog heart. Biochim. Biophys. Acta 664, 445-448.
32. V. Natarajan, P.V. Reddy, P.C. Schmid and H.H.O. Schmid (1982) N-Acylation of ethanolamine phospholipids in canine myocardium. Biochim. Biophys. Acta 712, 342-355.
33. P.V. Reddy, V. Natarajan, P.C. Schmid and H.H.O. Schmid (1983) N-Acylation of dog heart ethanolamine phospholipids by transacylase activity. Biochim. Biophys. Acta 750, 472-480.
34. P.V. Reddy, P.C. Schmid, V. Natarajan and H.H.O. Schmid (1983) The role of cardiolipin as an acyl donor in dog heart N-acylethanolamine phospholipid biosynthesis. Biochim. Biophys. Acta 751, 241-246.
35. P.V. Reddy, P.C. Schmid, V. Natarajan, T. Muramatsu and H.H.O. Schmid (1984) Properties of canine myocardial phosphatidylethanolamine N-acyltransferase. Biochim. Biophys. Acta 795, 130-136.
36. P.C. Schmid and H.H.O. Schmid (1987) N-Acylation of ethanolamine phospholipids by acyl transfer does not involve hydrolysis. Biochim. Biophys. Acta 922, 398-400.
37. V. Natarajan, P.C. Schmid, P.V. Reddy, M.L. Zuzarte-Augustin and H.H.O. Schmid (1983) Biosynthesis of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 41, 1303-1312.
38. V. Natarajan, P.C. Schmid and H.H.O. Schmid (1986) N-acylethanolamine phospholipid metabolism in normal and ischemic rat brain. Biochim. Biophys. Acta 878, 32-41.
39. V. Natarajan, P.C. Schmid, P.V. Reddy, M.L. Zuzarte-Augustin and H.H.O. Schmid (1985) Occurrence of N-acylethanolamine phospholipids in fish brain and spinal cord. Biochim. Biophys. Acta 835, 426-433.
40. V. Di Marzo, A. Fontana, H. Cadas, S. Schinelli, G. Cimino, J-C. Schwartz and D. Piomelli (1994) Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature 372, 686-691.
41. 2+ -dependent transacylase and phosphodiesterase activities. Biochem. Biophys. Res. Commun. 218, 113-117.
42. H.S. Hansen, L. Lauritzen, A.M. Strand, B. Moesgaard and A. Frandsen (1995) Glutamate stimulates the formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cortical neurons in culture. Biochim. Biophys. Acta 1258, 303-308.
43. P.C. Schmid, R.J. Krebsbach, S.R. Perry, T.M. Dettmer, J.L. Maassen and H.H.O. Schmid (1995) Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain. FEBS Lett. 375, 117-120.
44. M.E. Blank, E.A. Cress, M. Robinson and F. Snyder (1985) Metabolism of unique diarachidonoyl and linoleoylarachidonoyl species of ethanolamine and choline phosphoglycerides in rat testes. Biochim. Biophys. Acta 833, 366-371.
45. P.C. Schmid, I. Spimrova and H.H.O. Schmid (1995) Incorporation of exogenous fatty acids into molecular species of rat hepatocyte phosphatidylcholine. Arch. Biochem. Biophys. 322, 306-312.
46. P.C. Schmid, I. Spimrova, T. Kuwae and H.H.O. Schmid (1996) Generation and remodeling of 1,2-diarachidonoyl glycerophospholipids in resting and stimulated cells. FASEB J. 10, A1115.
47. R.A. Bomstein (1965) A new class of phosphatides isolated from soft wheat flour. Biochem. Biophys. Res. Commun. 21, 49-54.
48. K.D. Chapman and T.S. Moore, Jr. (1993) N-Acylphosphatidylethanolamine synthesis in plants: occurrence, molecular composition, and phospholipid origin. Arch. Biochem. Biophys. 301, 21-33.
49. K. D. Chapman and T.S. Moore, Jr. (1993) Catalytic properties of a newly discovered acyltransferase that synthesizes N-acylphosphatidylethanolamine in cottonseed (Gossypium hirsutum L.) microsomes. Plant Physiol. 102, 761-769.
50. K.D. Chapman, I. Lin and A.D. DeSouza (1995) Metabolism of cottonseed microsomal N-acylphosphatidylethanolamine. Arch. Biochem. Biophys. 318, 401-407.
51. P.C. Schmid, P.V. Reddy, V. Natarajan and H.H.O. Schmid (1983) Metabolism of N-acylethanolamine phospholipids by a mammalian phosphodiesterase of the phospholipase D type. J. Biol. Chem. 258, 9302-9306.
52. V. Natarajan, P.C. Schmid, P.V. Reddy and H.H.O. Schmid (1984) Catabolism of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 42, 1613-1619.
53. P.C. Schmid, M.L. Zuzarte-Augustin and H.H.O. Schmid (1985) Properties of rat liver N-acylethanolamine amidohydrolase. J. Biol. Chem. 260, 14145-14149.
54. D.G. Deutsch and S.A. Chin (1993) Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem. Pharmacol. 46, 791-796.
55. B. Koutek, G.D. Prestwich, A.C. Howlett, S.A. Chin, D. Salehani, N. Akhavan and D.G. Deutsch (1994) Inhibitors of arachidonyl ethanolamide hydrolysis. J. Biol. Chem. 269, 22937-22940.
56. F. Desarnaud, H. Cadas and D. Piomelli (1995) Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization. J. Biol. Chem. 270, 6030-6035.
57. C.J. Hillard, D.M. Wilkison, W.S. Edgemond and W.B. Campbell (1995) Characterization of the kinetics and distribution of N-arachidonylethanolamine (anandamide) hydrolysis by rat brain. Biochim. Biophys. Acta 1257, 249-256.
58. N. Ueda, Y. Kurahashi, S. Yamamoto and T. Tokunaga (1995) Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J. Biol. Chem. 270, 23823-23827.
59. S. Maurelli, T. Bisogno, L. De Petrocellis, A. Di Lucciá, G. Marino and V. Di Marzo (1995) Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma anandamide amidohydrolase. FEBS Lett. 377, 82-86.
60. B.F. Cravatt, O. Prospero-Garcia, G. Siuzdak, N.B. Gilula, S.J. Henriksen, D.L. Boger and R.A. Lerner (1995) Chemical characterization of a family of brain lipids that induce sleep. Science 268, 1506-1509.
61. M. Colodzin, N.R. Bachur, H. Weissbach and S. Udenfriend (1963) Enzymatic formation of fatty acid amides of ethanolamine by rat liver microsomes. Biochem. Biophys. Res. Commun. 10, 165-170.
62. N. Bachur and S. Udenfriend (1966) Microsomal synthesis of fatty acid amides. J. Biol. Chem. 241, 1308-1313.
63. K.K. Kruszka and R.W. Gross (1994) 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, 14345-14348.
64. W.A. Devane and J. Axelrod (1994) Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain membranes. Proc. Natl. Acad. Sci. USA 91, 6698-6701.