Generation of N-acylphosphatidylethanolamine by members of the phospholipase A/acyltransferase (PLA/AT) family

Journal of Biological Chemistry

Volumn 287, Issue 38, 2012, Pages 31905-31919

  Uyama, Toru ^a   Ikematsu, Natsuki ^b   Inoue, Manami ^b   Shinohara, Naoki ^a   Jin, Xing Hua ^b,c   Tsuboi, Kazuhito ^a   Tonai, Takeharu ^d   Tokumura, Akira ^b   Ueda, Natsuo ^a  

^a KAGAWA UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c QIQIHAR MEDICAL UNIVERSITY   (China)

^d National Hospital Organization   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMAL TISSUE; ENDOGENOUS LEVEL; ETHANOLAMINES; GLYCEROPHOSPHOLIPIDS; HEK293 CELLS; HELA CELL; IN-VIVO; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; LIVING CELL; N-ACYLETHANOLAMINES; PHOSPHATIDYLETHANOLAMINE; PHOSPHOLIPASE A; PHOSPHOLIPASE D; STABLE EXPRESSION;

CYTOLOGY; ENZYMES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHOSPHOLIPIDS; TISSUE;

PLANTS (BOTANY);

CARBON 14; ENZYME; ETHANOLAMINE; ETHANOLAMINE DERIVATIVE; N ACYL PHOSPHATIDYLETHANOLAMINE; N ACYL TRANSFERASE; N ACYLETHANOLAMINE; N ACYLPHOSPATIDYLETHANOLAMINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHOLIPASE A ACYLTRANSFERASE; PHOSPHOLIPASE A ACYLTRANSFERASE 1; PHOSPHOLIPASE A ACYLTRANSFERASE 2; PHOSPHOLIPASE A ACYLTRANSFERASE 3; PHOSPHOLIPASE A ACYLTRANSFERASE 4; PHOSPHOLIPASE A ACYLTRANSFERASE 5; PHOSPHOLIPASE D; PHOSPHOLIPID METABOLIZING ENZYME; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

ACYLATION; ANIMAL CELL; ARTICLE; CELL LABELING; CELL STRAIN COS7; CELL STRAIN HEK293; CONTROLLED STUDY; ENZYME ACTIVITY; HELA CELL; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FAMILY; TANDEM MASS SPECTROMETRY;

ACYLTRANSFERASES; ANIMALS; BASE SEQUENCE; CERCOPITHECUS AETHIOPS; COS CELLS; GENE EXPRESSION REGULATION; HEK293 CELLS; HELA CELLS; HUMANS; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; PEROXISOMES; PHOSPHATIDYLETHANOLAMINES; PHOSPHOLIPASE D; PHOSPHOLIPASES A; PHOSPHOLIPIDS; RNA INTERFERENCE; TANDEM MASS SPECTROMETRY;

ANIMALIA;

EID: 84866355195     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M112.368712     Document Type: Article

References (43)

1. Schmid, H. H. O., Schmid, P. C., and Natarajan, V. (1990) N-Acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29, 1-43 (Pubitemid 120036504)
2. Hansen, H. S., Moesgaard, B., Hansen, H. H., and Petersen, G. (2000) N-Acylethanolamines and precursor phospholipids. Relation to cell injury. Chem. Phys. Lipids 108, 135-150
3. Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949 (Pubitemid 23026736)
4. Zygmunt, P. M., Petersson, J., Andersson, D. A., Chuang, H., Sørgård, M., Di Marzo, V., Julius, D., and Högestätt, E. D. (1999) Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 400, 452-457 (Pubitemid 29361798)
5. Calignano, A., La Rana, G., Giuffrida, A., and Piomelli, D. (1998) Control of pain initiation by endogenous cannabinoids. Nature 394, 277-281 (Pubitemid 28335039)
6. Solorzano, C., Zhu, C., Battista, N., Astarita, G., Lodola, A., Rivara, S., Mor, M., Russo R, Maccarrone, M., Antonietti, F., Duranti, A., Tontini, A., Cuzzocrea, S., Tarzia, G., and Piomelli, D. (2009) Selective N-acylethanol-amine-hydrolyzing acid amidase inhibition reveals a key role for endogenous palmitoylethanolamide in inflammation. Proc. Natl. Acad. Sci. U.S.A. 106, 20966-20971
7. Rodríguez de Fonseca, F., Navarro, M., Gómez, R., Escuredo, L., Nava, F., Fu, J., Murillo-Rodríguez, E., Giuffrida, A., LoVerme, J., Gaetani, S., Kathuria, S., Gall, C., and Piomelli, D. (2001) An anorexic lipid mediator regulated by feeding. Nature 414, 209-212 (Pubitemid 33051235)
8. Fu, J., Gaetani, S., Oveisi, F., Lo Verme, J., Serrano, A., Rodríguez De Fonseca, F., Rosengarth, A., Luecke, H., Di Giacomo, B., Tarzia, G., and Piomelli, D. (2003) Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α. Nature 425, 90-93 (Pubitemid 37101723)
9. LoVerme, J., Russo, R., La Rana, G., Fu, J., Farthing, J., Mattace-Raso, G., Meli, R., Hohmann, A., Calignano, A., and Piomelli, D. (2006) Rapid broad spectrum analgesia through activation of peroxisome proliferator-activated receptor-α. J. Pharmacol. Exp. Ther. 319, 1051-1061
10. Ahern, G. P. (2003) Activation of TRPV1 by the satiety factor oleoylethanolamide. J. Biol. Chem. 278, 30429-30434
11. Overton, H. A., Babbs, A. J., Doel, S. M., Fyfe, M. C., Gardner, L. S., Griffin, G., Jackson, H. C., Procter, M. J., Rasamison, C. M., Tang-Christensen, M., Widdowson, P. S., Williams, G. M., and Reynet, C. (2006) Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small molecule hypophagic agents. Cell Metab. 3, 167-175
12. Ueda, N., Tsuboi, K., and Uyama, T. (2010) N-Acylethanolamine metabolism with special reference to N-acylethanolamine-hydrolyzing acid amidase (NAAA). Prog. Lipid Res. 49, 299-315
13. Ueda, N., Tsuboi, K., and Uyama, T. (2010) Enzymological studies on the biosynthesis of N-acylethanolamines. Biochim. Biophys. Acta 1801, 1274-1285
14. Cadas, H., Gaillet, S., Beltramo, M., Venance, L., and Piomelli, D. (1996) Biosynthesis of an endogenous cannabinoid precursor in neurons and its control by calcium and cAMP. J. Neurosci. 16, 3934-3942 (Pubitemid 26176057)
15. Cadas, H., di Tomaso, E., and Piomelli, D. (1997) Occurrence and biosynthesis of endogenous cannabinoid precursor, N- arachidonoylphosphatidylethanolamine, in rat brain. J. Neurosci. 17, 1226-1242 (Pubitemid 27073726)
16. 2+-independent phosphatidylethanolamine N-acyltransferase generating the anandamide precursor and its congeners. J. Biol. Chem. 282, 3614-3623
17. Okamoto, Y., Morishita, J., Tsuboi, K., Tonai, T., and Ueda, N. (2004) Molecular characterization of a phospholipase D generating anandamide and its congeners. J. Biol. Chem. 279, 5298-5305 (Pubitemid 38220550)
18. Sun, Y. X., Tsuboi, K., Okamoto, Y., Tonai, T., Murakami, M., Kudo, I., and Ueda, N. (2004) Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A2 and lysophospholipase D. Biochem. J. 380, 749-756 (Pubitemid 38850516)
19. Simon, G. M., and Cravatt, B. F. (2006) Endocannabinoid biosynthesis proceeding through glycerophospho-N-acylethanolamine and a role for α/β-hydrolase 4 in this pathway. J. Biol. Chem. 281, 26465-26472 (Pubitemid 44401855)
20. Tsuboi, K., Okamoto, Y., Ikematsu, N., Inoue, M., Shimizu, Y., Uyama, T., Wang, J., Deutsch, D. G., Burns, M. P., Ulloa, N. M., Tokumura, A., and Ueda, N. (2011) Enzymatic formation of N-acylethanolamines from N-acylethanolamine plasmalogen through N-acylphosphatidylethanolaminehydrolyzing phospholipase D-dependent and -independent pathways. Biochim. Biophys. Acta 1811, 565-577
21. Cravatt, B. F., Giang, D. K., Mayfield, S. P., Boger, D. L., Lerner, R. A., and Gilula, N. B. (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty acid amides. Nature 384, 83-87 (Pubitemid 26374593)
22. Tsuboi, K., Sun, Y. X., Okamoto, Y., Araki, N., Tonai, T., and Ueda, N. (2005) Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase. J. Biol. Chem. 280, 11082-11092 (Pubitemid 40418412)
23. McKinney, M. K., and Cravatt, B. F. (2005) Structure and function of fatty acid amide hydrolase. Annu. Rev. Biochem. 74, 411-432 (Pubitemid 40995513)
24. Hajnal, A., Klemenz, R., and Schäfer, R. (1994) Subtraction cloning of H-rev107, a gene specifically expressed in H-ras-resistant fibroblasts. Oncogene 9, 479-490 (Pubitemid 24041527)
25. DiSepio, D., Ghosn, C., Eckert, R. L., Deucher, A., Robinson, N., Duvic, M., Chandraratna, R. A., and Nagpal, S. (1998) Identification and characterization of a retinoid-induced class II tumor suppressor/growth regulatory gene. Proc. Natl. Acad. Sci. U.S.A. 95, 14811-14815 (Pubitemid 29003712)
26. Akiyama, H., Hiraki, Y., Noda, M., Shigeno, C., Ito, H., and Nakamura, T. (1999) Molecular cloning and biological activity of a novel Ha-Ras suppressor gene predominantly expressed in skeletal muscle, heart, brain, and bone marrow by differential display using clonal mouse EC cells, ATDC5. J. Biol. Chem. 274, 32192-32197
27. Shyu, R. Y., Hsieh, Y. C., Tsai, F. M., Wu, C. C., and Jiang, S. Y. (2008) Cloning and functional characterization of the HRASLS2 gene. Amino Acids 35, 129-137
28. 2+- independent phosphatidylethanolamine N-acyltransferases. Biochim. Biophys. Acta 1791, 32-38
29. 2+- independent cytosolic phospholipase A1/2 of the thiol hydrolase-type. J. Lipid Res. 50, 685-693
30. Uyama, T., Jin, X. H., Tsuboi, K., Tonai, T., and Ueda, N. (2009) Characterization of the human tumor suppressors TIG3 and HRASLS2 as phos-pholipid-metabolizing enzymes. Biochim. Biophys. Acta 1791, 1114-1124
31. Shinohara, N., Uyama, T., Jin, X. H., Tsuboi, K., Tonai, T., Houchi, H., and Ueda, N. (2011) Enzymological analysis of the tumor suppressor A-C1 reveals a novel group of phospholipid-metabolizing enzymes. J. Lipid Res. 52, 1927-1935
32. Schmid, P. C., Reddy, P. V., Natarajan, V., and Schmid, H. H. O. (1983) Metabolism of N-acylethanolamine phospholipids by a mammalian phosphodiesterase of the phospholipase D type. J. Biol. Chem. 258, 9302-9306
33. Ueda, N., Yamamoto, K., Yamamoto, S., Tokunaga, T., Shirakawa, E., Shinkai, H., Ogawa, M., Sato, T., Kudo, I., Inoue, K., Takizawa, H., Nagano, T., Hirobe, M., Matsuki, N., and Saito, H. (1995) Lipoxygenase-catalyzed oxygenation of arachidonylethanolamide, a cannabinoid receptor agonist. Biochim. Biophys. Acta 1254, 127-134
34. Bligh, E. G., and Dyer, W. J. (1959) A rapid method of total lipid extraction and purification. Can. J. Med. Sci. 37, 911-917
35. Okamoto, Y., Morishita, J., Wang, J., Schmid, P. C., Krebsbach, R. J., Schmid, H. H. O., and Ueda, N. (2005) Mammalian cells stably overexpressing N-acylphosphatidylethanolamine-hydrolyzing phospholipase D exhibit significantly decreased levels of N-acylphosphatidylethanolamines. Biochem. J. 389, 241-247 (Pubitemid 40978028)
36. Uyama, T., Ichi, I., Kono, N., Inoue, A., Tsuboi, K., Jin, X. H., Araki, N., Aoki, J., Arai, H., and Ueda, N. (2012) Regulation of peroxisomal lipid metabolism by catalytic activity of tumor suppressor H-rev107. J. Biol. Chem. 287, 2706-2718
37. Luetterforst, R., Stang, E., Zorzi, N., Carozzi, A., Way, M., and Parton, R. G. (1999) Molecular characterization of caveolin association with the Golgi complex. Identification of a cis-Golgi targeting domain in the caveolin molecule. J. Cell Biol. 145, 1443-1459 (Pubitemid 29310002)
38. Honsho, M., Asaoku, S., and Fujiki, Y. (2010) Post-translational regulation of fatty acyl-CoA reductase 1, Far1, controls ether glycerophospholipid synthesis. J. Biol. Chem. 285, 8537-8542
39. Tokumura, A., Carbone, L. D., Yoshioka, Y., Morishige, J., Kikuchi, M., Postlethwaite, A., and Watsky, M. A. (2009) Elevated serum levels of arachidonoyl-lysophosphatidic acid and sphingosine 1-phosphate in systemic sclerosis. Int. J. Med. Sci. 6, 168-176
40. Chalvardjian, A., and Rudnicki, E. (1970) Determination of lipid phosphorus in the nanomolar range. Anal. Biochem. 36, 225-226
41. Simon, G. M., and Cravatt, B. F. (2008) Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho- N-acylethanolamine precursors in mouse brain. J. Biol. Chem. 283, 9341-9349
42. Fegley, D., Gaetani, S., Duranti, A., Tontini, A., Mor, M., Tarzia, G., and Piomelli, D. (2005) Characterization of the fatty acid amide hydrolase inhibitor cyclohexyl carbamic acid 3′-carbamoyl-biphenyl-3-yl ester (URB597). Effects on anandamide and oleoylethanolamide deactivation. J. Pharmacol. Exp. Ther. 313, 352-358 (Pubitemid 40411361)
43. Hansen, H. S., Lauritzen, L., Strand, A. M., Moesgaard, B., and Frandsen, A. (1995) Glutamate stimulates the formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cortical neurons in culture. Biochim. Biophys. Acta 1258, 303-308