Acyltransferases and transacylases involved in fatty acid remodeling of phospholipids and metabolism of bioactive lipids in mammalian cells

Journal of Biochemistry

Volumn 122, Issue 1, 1997, Pages 1-16

  Yamashita, Atsushi ^a   Sugiura, Takayuki ^a   Waku, Keizo ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

acyl CoA; Acyltransferase; Arachidonic acid; Fatty acid remodeling; Lysophospholipid

Indexed keywords

ACYL COENZYME A; ACYLTRANSFERASE; FATTY ACID; LYSOPHOSPHOLIPID; PHOSPHOLIPID; POLYUNSATURATED FATTY ACID; SATURATED FATTY ACID;

ACYLATION; ANIMAL TISSUE; ESTERIFICATION; LIPID METABOLISM; MAMMAL CELL; NONHUMAN; RAT; REVIEW;

ANIMALIA; MAMMALIA;

EID: 0030844660     PISSN: 0021924X     EISSN: None     Source Type: Journal    
DOI: 10.1093/oxfordjournals.jbchem.a021715     Document Type: Review

References (149)

1. Lands, W.E.M. and Crawford, C.G. (1976) Enzymes of membrane phospholipid metabolism in animals in The Enzymes of Biological Membranes (Martonosi, A., ed.) Vol. 2, pp. 3-85, Plenum Press, New York
2. Holub, B.J. and Kuksis, A. (1978) Metabolism of molecular species of diacylglycerophospholipids. Adv. Lipid Res. 16, 1-125
3. Snyder, F., ed. (1972) Ether Lipids. Chemistry and Biology. Academic Press, New York
4. Sugiura, T. and Waku, K. (1987) Composition of alkyl ether-linked phospholipids in mammalian tissues in Platelet-Activating Factor and Related Lipid Mediators (Snyder, F., ed.) pp. 55-85, Plenum Press, New York
5. Nakagawa, Y. and Waku, K. (1989) The metabolism of glycerophospholipid and its regulation in monocytes and macrophages. Prog. Lipid Res. 28, 205-243
6. MacDonald, J.I.S. and Sprecher, H. (1991) Phospholipid fatty acid remodeling in mammalian cells. Biochim. Biophys. Acta 1084, 105-121
7. Snyder, F., Lee, T.-C., and Blank, M.L. (1992) The role of transacylases in the metabolism of arachidonate and platelet activating factor. Prog. Lipid Res. 31, 65-86
8. Sugiura, T. and Waku, K. (1992) Coenzyme A-independent acyltransferase. Methods Enzymol. 209, 72-80
9. Waku, K. and Inoue, K., eds. (1996) Lipid messengers in the nervous system. J. Lipid Mediators Cell Signal. 14, 1-374 (Special issue)
10. Tokumura, A. (1995) A family of phospholipid autacoids: occurrence, metabolism and bioactions. Prog. Lipid Res. 34, 151-184
11. Patton, G.M., Fasulo, J.M., and Robins, S.J. (1982) Separation of phospholipids and individual molecular species of phospholipids by high-performance liquid chromatography. J. Lipid Res. 23, 190-196
12. Nakagawa, Y. and Horrocks, L.A. (1983) Separation of alkenylacyl, alkylacyl and diacyl analogues and their molecular species by high performance liquid chromatography. J. Lipid Res. 24, 1268-1275
13. Blank, M.L., Robinson, M., Fitzgerald, V., and Snyder, F. (1984) Novel quantitative method for determination of molecular species of phospholipids and diglycerides. J. Chromatogr. 298, 473-482
14. Takamura, H., Narita, H., Urade, R., and Kito, M. (1986) Quantitative analysis of polyenoic phospholipid molecular species by high performance liquid chromatography. Lipids 21, 356-361
15. Nakagawa, Y., Sugiura, T., and Waku, K. (1985) The molecular species composition of diacyl-, alkylacyl-, alkenylacylglycerophospholipids in rabbit alveolar macrophages. High amounts of 1-O-hexadecyl-2-arachidonyl molecular species in alkylacylglycerophosphocholine. Biochim. Biophys. Acta 833, 323-329
16. Nakagawa, Y., Waku, K., Hirose, A., Kawashima, Y., and Kozuka, H. (1986) Effect of clofibric acid on molecular species composition of diacyl glycerophosphocholine of rat liver microsomes. Lipids 21, 634-638
17. Horrocks, L.A. and Sharma, M. (1982) Plasmalogen and O-alkyl glycerophospholipids in Phospholipids (Hawthone, J.N. and Ansell, G.B., eds.) pp. 51-93, Elsevier, Amsterdam
18. Roberts, W.L., Myher, J.J., Kukusis, A., and Rosenberry, T.L. (1988) Alkylacylglycerol molecular species in the glycosylinositol phospholipid membrane anchor of bovine erythrocyte acetyltransferase. Biochem. Biophys. Res. Commun. 150, 271-277
19. 3H]glycerol. Biochim. Biophys. Acta 210, 15-27
20. 14C-glycerol into different species of phosphatidic acid, phosphatidylethanolamine, and phosphatidylcholine. J. Biol. Chem. 243, 4440-4451
21. Arvidson, G.A.E. (1968) Biosynthesis of phosphatidylcholines in rat liver. Eur. J. Biochem. 5, 415-421
22. Kanoh, H. (1969) Biosynthesis of molecular species of phosphatidyl choline and phosphatidylethanolamine from radioactive precursors in rat liver slices. Biochim. Biophys. Acta 176, 756-763
23. Okuyama, H. and Lands, W.E.M. (1972) Variable selectivities of acyl coenzyme A:monoacylglycerophosphate acyltransferases in rat liver. J. Biol. Chem. 247, 1414-1423
24. Fleming, P.J. and Hajra, A. (1977) 1-Alkyl-sn-glycero-3-phosphate:acyl-CoA acyltransferase in rat brain microsomes. J. Biol. Chem. 252, 1663-1672
25. Nakagawa, Y., Rüstow, B., Rabe, H., Kunze, D., and Waku, K. (1989) The de novo synthesis of molecular species of phosphatidylinositol from endogenously labeled CDP diacylglycerol in alveolar macrophage microsomes. Arch. Biochem. Biophys. 268, 559-566
26. Kanoh, H. and Ohno, K. (1975) Substrate-selectivity of rat liver microsomal 1,2-diacylglycerol:CDP-choline(ethanolamine) choline(ethanolamine)phosphotransferase in utilizing endogenous substrates. Biochim. Biophys. Acta 380, 199-207
27. Holub, B.J. (1978) Differential utilization of 1-palmitoyl and 1-stearoyl homologues of various unsaturated 1,2-diacyl-sn-glycerols for phosphatidylcholine and phosphatidylethanolamine synthesis in rat liver microsomes. J. Biol. Chem. 253, 691-696
28. Masuzawa, Y., Xakagawa, Y., Waku, K., and Lands, W.E.M. (1982) Distinct selectivity for docosahexaenoic acid incorporation by Ehrlich ascites tumor cells. Biochim. Biophys. Acta 713, 185-192
29. Masuzawa, Y., Okano, S., Waku, K., Sprecher, H., and Lands, W.E.M. (1986) Selective incorporation of various C-22 polyun-saturated fatty acids in Ehrlich ascites tumor cells. J. Lipid Res. 27, 1145-1152
30. Nakagawa, Y. and Waku, K. (1985) Selective synthesis of the hexaenoic molecular species of ether-linked glycerophosphoethanolamine of Ehrlich ascites tumor cells. Eur. J. Biochem. 152, 569-572
31. Onuma, Y., Masuzawa, Y., Ishima, Y., and Waku, K. (1984) Selective incorporation of docosahexaenoic acid in rat brain. Biochim. Biophys. Acta 793, 80-85
32. Lands, W.E.M. (1958) Metabolism of glycerolipids: A comparison of lecithin and triglyceride synthesis. J. Biol. Chem. 231, 883-888
33. Lands, W.E.M. (1960) Metabolism of glycerolipids. II. The enzymatic acylation of lysolecithin. J. Biol. Chem. 235, 2233-2237
34. Lands, W.E.M. and Hart, P. (1965) Metabolism of glycerolipids. VI. Specificities of acyl coenzyme A:phospholipid acyltransferases. J. Biol. Chem. 240, 1905-1911
35. Kanoh, H. and Ohno, K. (1973) Utilization of endogenous phospholipid by the back-reaction of CDP-choline(-ethanolamine):1,2-diglyceride choline(ethanolamine)-phosphotransferase in rat liver microsomes. Biochim. Biophys. Acta 306, 203-217
36. Okuyama, H., Yamada, K., and Ikezawa, H. (1975) Acceptor concentration effect in the selectivity of acyl-CoA:1-acylglycerylphosphorylcholine acyltransferase system in rat liver. J. Biol. Chem. 250, 1710-1713
37. Lands, W.E.M., Inoue, M., Sugiura, Y., and Okuyama, H. (1982) Selective incorporation of polyunsaturated fatty acids into phosphatidylcholine by rat liver microsomes. J. Biol. Chem. 257, 14968-14972
38. Baker, R.R. and Thompson, W. (1973) Selective acylation of 1-acylglycerophosphorylinositol by rat brain microsomes. Comparison with 1-acylglycerophosphorylcholine. J. Biol. Chem. 248, 7060-7065
39. Inoue, M., Murase, S., and Okuyama, H. (1984) Acyl coenzyme A:phospholipid acyltransferases in porcine platelets discriminate between ω-3 and ω-6 unsaturated fatty acids. Arch. Biochem. Biophys. 231, 29-37
40. Holub, B.J. (1980) The biosynthesis of phosphatidylserines by acylation of 1-acyl-sn-glycero-3-phosphoserine in rat liver. Biochim. Biophys. Acta 618, 255-262
41. Thompson, W. and Belina, H. (1986) Rapid accumulation of diacyl lipid in rat liver microsomes by selective acylation of 2-acyl-sn-glycero-3-phosphorylserine. Biochim. Biophys. Acta 876, 379-386
42. Batenburg, J.J., Longmore, W.J., Klazinga, W., and van Golde, L.M.G. (1979) Lysolecithin acyltransferase and lysolecithin: lysolecithin acyltransferase in adult rat lung alveolar type II epithelial cells. Biochim. Biophys. Acta 573, 136-144
43. Lands, W.E.M. and Hart, P. (1965) Metabolism of plasmalogen. III. Relative reactivities of acyl and alkenyl derivatives of glycero-3-phosphorylcholine. Biochim. Biophys. Acta 98, 532-538
44. Waku, K. and Lands, W.E.M. (1968) Acyl coenzyme A:1-alkenyl-glycero-3-phosphorylcholine acyltransferase action in plasmalogen biosynthesis. J. Biol. Chem. 243, 2654-2659
45. Waku, K. and Nakazawa, Y. (1970) Acyltransferase activity to 1-O-alkyl-glycero-3-phosphorylcholine in sarcoplasmic reticulum. J. Biochem. 68, 459-466
46. Waku, K. and Nakazawa, Y. (1977) Regulation of the fatty acid composition of alkyl ether phospholipid in Ehrlich ascites tumor cells. The substrate specificities of 1-O-alkylglycerol 3-phosphate and 1-O-alkylglycero-3-phosphorylcholine acyltransferases. J. Biochem. 82, 1779-1784
47. Fuse, I., Iwanaga, T., and Tai, H.-H. (1989) Phorbol ester, 1.2-diacylglycerol, and collagen induce inhibition of arachidonic acid incorporation into phospholipids in human platelets. J. Biol. Chem. 264, 3890-3895
48. Goppelt-Strube, M., Pfannkuche, H.J., Gemsa, D., and Resch, K. (1987) The diacylglycerols dioctanoylglycerol and oleoylacetylglycerol enhance prostaglandin synthesis by inhibition of the lysophosphatide acyltransferase. Biochem. J. 247, 773-777
49. Kawashima, Y. and Kozuka, H. (1984) Selective increase in acylation of 1-acylglycerophosphorylcholine in livers of rats and mice by peroxisome proliferators. Biochim. Biophys. Acta 793, 232-237
50. Issemann, I. and Green, S. (1990) Activation of member of the steroid hormone receptor superfamily by peroxisome proliferators. Nature 347, 645-650
51. Yashiro, K., Kameyama, Y., Mizuno, M., Hayashi, S., Sakashita, Y., and Yokota, Y. (1989) Phospholipid metabolism in rat submandibular gland. Positional distribution of fatty acids in phosphatidylcholine and microsomal lysophospholipid acyltransferase systems concerning proliferation. Biochim. Biophys. Acta 1005, 56-64
52. Deka, N., Sun, G.Y., and MacQuarrie, R.A. (1986) Purification and properties of acyl-CoA:1-acyl-sn-glycero-3-phosphocholine-O-acyltransferase from bovine brain microsomes. Arch. Biochem. Biophys. 246, 554-563
53. Sanjanwala, M., Sun, G.Y., Cutrera, M.A., and MacQuarrie, R.A. (1988) Acylation of lysophosphatidylcholine in bovine heart muscle microsomes: Purification and kinetic properties of acyl-CoA:1-acyl-sn-glycero-3-phosphocholine-O-acyltransferase. Arch. Biochem. Biophys. 265, 476-483
54. Sanjanwala, M., Sun, G.Y., and MacQuarrie, R.A. (1989) Purification and kinetic properties of lysophosphatidylinositol acyltransferase from bovine heart muscle microsomes and comparison with lysophosphatidylcholine acyltransferase. Arch. Biochem. Biophys. 271, 407-413
55. Irvine, R.F. and Dawson, R.M.C. (1979) Transfer of arachidonic acid between phospholipids in rat liver microsomes. Biochem. Biophys. Res. Commun. 91, 1399-1405
56. Sugiura, T., Masuzawa, Y., Nakagawa, Y., and Waku, K. (1988) Coenzyme A-dependent transacylation system in rabbit liver microsomes. J. Biol. Chem. 263, 17490-17498
57. Sugiura, T., Masuzawa, Y., Nakagawa, Y., and Waku, K. (1987) Transacylation of lyso platelet-activating factor and other lysophospholipids by macrophage microsomes. Distinct donor and acceptor selectivities. J. Biol. Chem. 262, 1199-1205
58. Robinson, M., Blank, M.L., and Snyder, F. (1985) Acylation of lysophospholipids by rabbit alveolar macrophages. Specificities of CoA-dependent and CoA-independent reactions. J. Biol. Chem. 260, 7889-7895
59. Flesch, I., Ecker, B., and Ferber, E. (1984) Acyltransferase-catalyzed cleavage of arachidonic acid from phospholipids and transfer to lysophosphatides in macrophages derived from bone marrow. Comparison of different donor- and acceptor substrate combinations. Eur. J. Biochem. 139, 431-437
60. Kramer, R.M., Prizker, C.R. and Deykin, D. (1984) Coenzyme A-mediated arachidonic acid transacylation system in human platelets. J. Biol. Chem. 259, 2403-2406
61. Colard, O., Breton, M., and Bereziat, G. (1984) Induction by lysophospholipids of CoA-dependent arachidonoyl transfer between phospholipids in rat platelet homogenates. Biochim. Biophys. Acta 793, 42-48
62. Ojima, A., Nakagawa, Y., Sugiura, T., Masuzawa, Y., and Waku, K. (1987) Selective transacylation of 1-O-alkylglycerophosphoethanolamine by docosahexaenoate and arachidonate in rat brain microsomes. J. Neurochem. 48, 1403-1410
63. Masuzawa, Y., Sugiura, T., Sprecher, H., and Waku, K. (1989) Selective acyl transfer in reacylation of brain glycerophospholipids. Comparison of three acylation systems for 1-alk-1′-enylglycero-3-phosphoethanolamine, 1-acylglycero-3-phosphoethanolamine and 1-acylglycero-3-phosphocholine in rat brain microsomes. Biochim. Biophys. Acta 1005, 1-12
64. Nijssen, J.G. and van den Bosch, H. (1986) Coenzyme A-mediated transacylation of sn-2 fatty acids from phosphatidylcholine in rat lung microsomes. Biochim. Biophys. Acta 875, 458-464
65. Itabe, H., King, W.C., Reynolds, C.N., and Glomset, J.A. (1992) Substrate specificity of a CoA-dependent stearoyl transacylase from bovine testis membranes. J. Biol. Chem. 267, 15319-15325
66. Darnell, J.C. and Saltiel, A.R. (1991) Coenzyme A-dependent, ATP-independent acylation of 2-acyl lysophosphatidylinositol in rat liver microsomes. Biochim. Biophys. Acta 1084, 292-299
67. Sugiura, T., Kudo, N., Ojima, T., Mabuchi-Itoh, K., Yamashita, A., and Waku, K. (1995) Coenzyme A-dependent cleavage of membrane phospholipids in several rat tissues: ATP-independent acyl-CoA synthesis and the generation of lysophospholipids. Biochim. Biophys. Acta 1255, 167-176
68. Sugiura, T., Kudo, N., Ojima, T., Kondo, S., Yamashita, A., and Waku, K. (1995) Coenzyme A-dependent modification of fatty acyl chains of rat liver membrane phospholipids: possible involvement of ATP-independent acyl-CoA synthesis. J. Lipid Res. 36, 440-450
69. Trotter, J., Flesch, I., Schmidt, B., and Ferber, E. (1982) Acyltransferase-catalyzed cleavage of arachidonic acid from phospholipids and transfer to lysophospholipids. J. Biol. Chem. 257, 1816-1823
70. Yamashita, A., Sato, K., Watanabe, M., Tokudome, Y., Sugiura, T., and Waku, K. (1994) Induction of coenzyme A-dependent transacylation activity in rat liver microsomes by administration of clofibrate. Biochim. Biophys. Acta 1211, 263-269
71. Brumley, G. and van den Bosch, H. (1977) Lysophospholipase-transacylase from rat lung: isolation and partial purification. J. Lipid Res. 18, 523-532
72. Vianen, G.M. and van den Bosch, H. (1978) Lysophospholipase and lysophosphatidylcholine:lysophosphatidylcholine transacylase from rat lung: Evidence for single enzyme and some aspects of its specificity. Arch. Biochem. Biophys. 190, 373-378
73. van Heusden, G.P.H., Reutelingsperger, C.P.M., and van den Bosch, H. (1981) Substrate specificity of lysophospholipase-transacylase from rat lung and its action on various physical forms of lysophosphatidylcholine. Biochim. Biophys. Acta 663, 22-33
74. Gross, R.W., Drisdel, R.C., and Sobel, B.E. (1983) Rabbit myocardial lysophospholipase-transacylase. J. Biol. Chem. 258, 15165-15172
75. Sugimoto, H. and Yamashita, S. (1994) Purification, characterization, and inhibition by phosphatidic acid of lysophospholipase transacylase from rat liver. J. Biol. Chem. 269, 6252-6258
76. Zupan, L.A., Steffens, D.L., Berry, C.A., Landt, M., and Gross, R.W. (1992) Cloning and expression of a human 14-3-3 protein mediating phospholipolysis. Identification of an arachidonoyl-enzyme intermediate during catalysis. J. Biol. Chem. 267, 8707-8710
77. Pernas, P., Oliver, J.L., Legoy, M.D., and Bereziat, G. (1990) Phospholipid synthesis by extracellular phospholipase A2 in organic solvents. Biochem. Biophys. Res. Commun. 168, 644-650
78. Reynolds, L.J., Hughes, L.L., Louis, A.I., Kramer, R.M., and Dennis, E.A. (1993) Metal ion and salt effects on the phospholipase A2, lysophospholipase, and transacylase activities of human cytosolic phospholipase A2. Biochim. Biophys. Acta 1167, 272-280
79. Balsinde, J., Bianco, I.D., Ackermann, E.J., Conde-Frieboes, K., and Dennis, E.A. (1995) Inhibition of calcium-independent phospholipase A2 prevents arachidonic acid incorporation and phospholipid remodeling in P388D1 macrophages. Proc. Natl. Acad. Sci. USA 92, 8527-8531
80. Kramer, R.M. and Deykin, D. (1983) Arachidonoyl transacylase in human platelets. Coenzyme A-independent transfer of arachidonate from phosphatidylcholine to lysophoplasmenylethanolamine. J. Biol. Chem. 258, 13806-13811
81. Kramer, R.M., Patton, G.M., Prizker, C.R., and Deykin, D. (1984) Metabolism of platelet-activating factor in human platelets. Transacylase-mediated synthesis of 1-O-alkyl-arachidonoyl-sn-glycero-3-phosphocholine. J. Biol. Chem. 259, 13316-13320
82. Sugiura, T. and Waku, K. (1985) CoA-independent transfer of arachidonic acid from 1,2-diacyl-sn-glycero-3-phosphocholine to 1-O-alkyl-sn-glycero-3-phosphocholine (lyso platelet-activating factor) by macrophage microsomes. Biochem. Biophys. Res. Commun. 127, 384-390
83. Sugiura, T., Masuzawa, Y., and Waku, K. (1985) Transacylation of 1-O-alkyl-sn-glycero-3-phosphocholine (lyso platelet-activating factor) and 1-O-alkenyl-sn-glycero-3-phosphoethanolamine with docosahexaenoic acid (22:6ω3). Biochem. Biophys. Res. Commun. 133, 574-580
84. Chilton, F.H. and Murphy, R.C. (1986) Remodeling of arachidonate-containing phosphoglycerides within the human neutrophil. J. Biol. Chem. 261, 7771-7777
85. Chilton, F.H., Hadley, J.S., and Murphy, R.C. (1987) Incorporation of arachidonic acid into 1-acyl-2-lyso-sn-glycero-3-phosphocholine of the human neutrophil. Biochim. Biophys. Acta 917, 48-56
86. Colard, O., Breton, M., and Bereziat, G. (1984) Arachidonyl transfer from diacyl phosphatidylcholine to ether phospholipids in rat platelets. Biochem. J. 222, 657-662
87. Reddy, P.V. and Schmit, H.H.O. (1985) Selectivity of acyl transfer between phospholipids: Arachidonoyl transacylase in dog heart membranes. Biochem. Biophys. Res. Commun. 129, 381-388
88. Blank, M.L., Wykle, R.L., and Snyder, F. (1973) The retention of arachidonic acid in ethanolamine plasmalogens of rat testes during essential fatty acid deficiency. Biochim. Biophys. Acta 316, 28-34
89. Masuzawa, Y., Okano, S., Nakagawa, Y., Ojima, A., and Waku, K. (1986) Selective acylation of alkyllysophospholipids by docosahexaenoic acid in Ehrlich ascites cells. Biochim. Biophys. Acta 876, 80-90
90. Breton, M. and Colard, O. (1991) Protein kinase C promotes arachidonate mobilization through enhancement of CoA-independent transacylase activity in platelets. Biochem. J. 280, 93-98
91. Winkler, J.D., Sung, C.M., Huang, L., and Chilton, F.H. (1994) CoA-independent transacylase activity is increased in human neutrophils after treatment with tumor necrosis factor-α. Biochim. Biophys. Acta 1215, 133-140
92. Winkler, J.D., Mccarte-Roshak, A., Huang, L., Sung, C.-M., Bolognese, B., and Marshall, L.A. (1994) Biochemical and pharmacological comparison of cytosolic phospholipase A2, human synovial fluid phospholipase A2 and CoA-independent transacylase. J. Lipid Mediators Cell Signal. 10, 315-330
93. Sugiura, T., Katayama, O., Fukui, J., Nakagawa, Y., and Waku, K. (1984) Mobilization of arachidonic acid between diacyl and ether phospholipids in rabbit alveolar macrophages. FEBS Lett. 165, 273-276
94. Nakagawa, Y., Kurihara, K., Sugiura, T., and Waku, K. (1985) Heterogeneity in the metabolism of the arachidonoyl molecular species of glycerophospholipids of rabbit alveolar macrophages. The interrelationship between metabolic activities and chemical structures of arachidonoyl molecular species. Eur. J. Biochem. 153, 267-268
95. Nakagawa, Y., Kurihara, K., Sugiura, T., and Waku, K. (1986) Relative degradation of different arachidonoyl molecular species of choline glycerophospholipids in opsonized zymosan-stimulated rabbit alveolar macrophages. Biochim. Biophys. Acta 876, 601-610
96. 2+ ionophore A23187. Biochem. J. 233, 691-695
97. Suga, K., Kawasaki, T., Blank, M.L., and Snyder, F. (1990) An arachidonoyl (polyenoic)-specific phospholipase A2 activity regulates the synthesis of platelet-activating factor in granulocytic HL-60 cells. J. Biol. Chem. 265, 12363-12371
98. Takayama, H., Kroll, M.H., Gimbrone, J.A., and Schafer, A.I. (1989) Turnover of eicosanoid precursor fatty acids among phospholipid classes and subclasses of cultured human umbilical vein endothelial cells. Biochem. J. 258, 427-434
99. Wey, H.E., Jakubowski, J.A., and Deykin, D. (1986) Incorporation and redistribution of arachidonic acid in diacyl and ether phospholipids of bovine aortic endothelial cells. Biochim. Biophys. Acta 878, 380-386
100. Shikano, M., Masuzawa, Y., and Yazawa, K. (1993) Effect of docosahexaenoic acid on the generation of platelet-activating factor by eosinophilic leukemia cells, EoI-1. J. Immunol. 150, 3525-3533
101. Benveniste, J., Henson, P.M., and Cochrane, C.G. (1972) Leukocyte-dependent histamine release from rabbit platelets. The role of IgE, basophil, and a platelet-activating factor. J. Exp. Med. 136, 1356-1377
102. Demopoulos, C.A., Pinckard, R.N., and Hanahan, D.J. (1979) Platelet-activating factor. Evidence for 1-O-alkyl-2-acetyl-sn-glyceryl-3-phosphorylcholine as the active component (a new class of lipid chemical mediators). J. Biol. Chem. 254, 9355-9358
103. Benveniste, J., Tence, M., Varenne, P., Bidault, J., Boullet, C., and Polonsky, J. (1979) Semi-synthese et structure purposee du facteur activant les plaquettes (P.A.F.); PAF-acether, un alkyl ether analogue de la lysophosphatidylcholine. C.R. Acad. Sci. [D], (Paris) 289, 1037-1040
104. Blank, M.L., Snyder, F., Byers, L.W., Brooks, B., and Muirhead, E.E. (1979) Antihypertensive activity of an alkyl ether analog of phosphatidylcholine. Biochem. Biophys. Res. Commun. 90, 1194-1200
105. Honda, Z., Nakamura, M., Miki, I., Minami, M., Watanabe, T., Seyama, Y., Okado, H., Toh, H., Ito, K., Miyamoto, T., and Shimizu, T. (1991) Cloning by functional expression of platelet-activating factor receptor from guinea-pig lung. Nature 349, 342-346
106. Izumi, T. and Shimizu, T. (1995) Platelet-activating factor-gene regulation and signal transduction. Biochim. Biophys. Acta 1259, 317-333
107. Snyder, F. (1995) Platelet-activating factor: the biosynthetic and catabolic enzymes. Biochem. J. 305, 689-705
108. Wykle, R.L., Malone, B., and Snyder, F. (1980) Enzymatic synthesis of 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine, a hypertensive and platelet-aggregating lipid. J. Biol. Chem. 255, 10256-10260
109. Sugiura, T., Fukuda, T., Masuzawa, Y., and Waku, K. (1990) Ether lysophospholipid-induced production of platelet-activating factor in human polymorphonuclear leukocytes. Biochim. Biophys. Acta 1047, 223-232
110. Uemura, Y., Lee, T.C., and Snyder, F. (1991) A coenzyme A-independent transacylase is linked to the formation of platelet-activating factor (PAF) by generating the lyso-PAF intermediate in the remodeling pathway. J. Biol. Chem. 266, 8268-8272
111. Nieto, M.L., Venable, M.E., Bauldry, S.A., Greene, D.G., Kennedy, M., Bass, D.A., and Wykle, R.J. (1991) Evidence that hydrolysis of ethanolamine plasmalogens triggers synthesis of platelet-activating factor via a transacylation reaction. J. Biol. Chem. 266, 18699-18706
112. Alonso, F., Gil, M.G., Sanchez-Crespo, M., and Mato, J.M. (1982) Activation of 1-alkyl-2-lysoglycero-3-phosphocholine. Acetyl-CoA transferase during phagocytosis in human polymorphonuclear leukocytes. J. Biol. Chem. 257, 3376-3378
113. Lee, T.C., Malone, B., Wasserman, S.I., Fitzgerald, V., and Snyder, F. (1982) Activities of enzymes that metabolize platelet-activating factor (1-alkyl-2-acetyl-sn-glycero-3-phosphocholine) in neutrophils and eosinophils from humans and the effect of a calcium ionophore. Biochem. Biophys. Res. Commun. 105, 1303-1308
114. Gomez-Cambronero, J., Mato, J.M., Vivanco, F., and Sanchez-Crespo, M. (1987) Phosphorylation of partially purified 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine:acetyl-CoA acetyltransferase from rat spleen. Biochem. J. 245, 893-897
115. Winkler, J.D., Fonteh, A.N., Sung, C.M., Heravi, J.D., Nixon, A.B., Chabot-Fletcher, M., Griswold, D., Marshall, L.A., and Chilton, F.H. (1995) Effects of CoA-independent transacylase inhibitors on the production of lipid inflammatory mediators. J. Pharmacol. Exp. Ther. 274, 1338-1347
116. Winkler, J.D., Eris, T., Sung, C.M., Chabot-Fletcher, M., Mayer, R.J., Surette, M.E., and Chilton, F.H. (1996) Inhibitors of coenzyme A-independent transacylase induce apoptosis in human HL-60 cells. J. Pharmacol. Exp. Ther. 279, 956-966
117. Lee, T.C., Uemura, Y., and Snyder, F. (1992) A novel CoA-independent transacetylase produces the ethanolamine plasmalogen and acyl analogs of platelet-activating factor (PAF) with PAF as the acetate donor in HL-60 cells. J. Biol. Chem. 267, 19992-20001
118. Lee, T.C., Ou, M.C., Shinozaki, K., Malone, B., and Snyder, F. (1996) Biosynthesis of N-acetylsphingosine by platelet-activating factor: sphingosine CoA-independent transacetylase in HL-60 cells. J. Biol. Chem. 271, 209-217
119. Schmid, H.H.O., Schmid, P.C., and Natarajan, V. (1990) N-Acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29, 1-43
120. Epps, D.E., Natarajan, V., Schmid, P.C., and Schmid, H.H.O. (1980) Accumulation of N-acylethanolamine glycerophospholipids in infarcted myocardium. Biochim. Biophys. Acta 618, 420-430
121. Natarajan, V., Reddy, P.V., Schmid, P.C., and Schmid, H.H.O. (1981) On the biosynthesis and metabolism of N-acylethanolamine glycerophospholipids in infarcted dog heart. Biochim. Biophys. Acta 664, 445-448
122. Natarajan, V., Reddy, P.V., Schmid, P.C., and Schmid, H.H.O. (1982) N-Acylation of ethanolamine phospholipids in canine myocardium. Biochim. Biophys. Acta 712, 342-355
123. 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
124. 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
125. Kruszuka, K.K. and Gross, R.W. (1994) The ATP- and CoA-independent synthesis of arachidonoylethanolamide. A novel mechanism underlying the synthesis of the endogenous ligand of the cannabinoid receptor. J. Biol. Chem. 269, 14345-14348
126. Devane, W.A. and Axelrod, J. (1994) Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain microsomes. Proc. Natl. Acad. Sci. USA 91, 6698-6701
127. Ueda, N., Kurahashi, Y., Yamamoto, S., and Tokunaga, T. (1995) Partial purification and characterization of porcine brain enzyme hydrolyzing and synthesizing anandamide. J. Biol. Chem. 270, 23823-23827
128. Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., Ishima, Y., and Waku, K. (1996) 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, 53-62
129. Di Marzo, V., Fontana, A., Cadas, H., Schinelli, S., Cimino, G., Schwartz, J.-C., and Piomelli, D. (1994) Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature 372, 686-691
130. 2+-dependent transacylase and phosphodiesterase activities. Biochem. Biophys. Res. Commun. 218, 113-117
131. Waku, K. (1992) Origins and fates of fatty acyl-CoA esters. Biochim. Biophys. Acta 1124, 101-111
132. +)-ATPase by long chain acyl coenzyme A. J. Biol. Chem. 264, 2605-2608
133. 2+ handling by permeabilized clonal pancreatic β-cells. J. Biol. Chem. 267, 19840-19845
134. Bronfman, M., Morales, M.N., and Orellana, A. (1988) Diacylglycerol activation of protein kinase C is modulated by long-chain acyl-CoA. Biochem. Biophys. Res. Commun. 152, 987-992
135. Li, Q., Yamamoto, N., Inoue, A., and Morisawa, S. (1990) Fatty acyl-CoAs are potent inhibitors of the nuclear thyroid hormone receptor in vitro. J. Biochem. 107, 699-702
136. Pfanner, N., Orci, L., Glick, B.S., Amherdt, M., Arden, S.R., Malhotra, V., and Rothman, J.E. (1989) Fatty acyl-coenzyme A is required for budding of transport vesicles from golgi cisternae. Cell 59, 95-102
137. Casy, P. (1995) Protein lipidation in cell signaling. Science 268, 221-225
138. Yamashita, A., Watanabe, M., Tonegawa, T., Sugiura, T., and Waku, K. (1995) Acyl-CoA binding and acylation of UDP-glucuronosyltransferase isoforms of rat liver: Their effect on enzyme activity. Biochem. J. 312, 301-308
139. Yamashita, A., Nagatsuka, T., Watanabe, M., Kondo, H., Sugiura, T., and Waku, K. (1997) Inhibition of UDP-glucuronosyltransferase activity by fatty acyl-CoA: kinetic studies and structure-activity relationship. Biochem. Pharmacol. 53, 561-570
140. Baisted, D.J., Robinson, B.S., and Vance, D.E. (1988) Albumin stimulated the release of lysophosphatidylcholine from cultured rat hepatocytes. Biochem. J. 253, 693-701
141. Khairallah, P.A. and Page, I.H. (1960) A vasopressor lipid in incubated plasma. Am. J. Physiol. 199, 341-345
142. Asaoka, Y., Oka, M., Yoshida, K., and Nishizuka, Y. (1991) Lysophosphatidylcholine as a possible second messenger synergistic to diacylglycerol and calcium ion for T-lymphocyte activation. Biochem. Biophys. Res. Commun. 178, 1378-1385
143. Asaoka, Y., Yoshida, K., Sasaki, Y., and Nishizuka, Y. (1993) Potential role of phospholipase A2 in HL-60 cell differentiation to macrophages induced by protein kinase C activation. Proc. Natl. Acad. Sci. USA 90, 4917-4921
144. Kume, N. and Gimbrone, M.A., Jr. (1994) Lysophosphatidylcholine transcriptionally induces growth factor gene expression in cultured human endothelial cells. J. Clin. Invest. 93, 907-911
145. Jalink, K., Hordijk, P.L., and Moolenaar, W.H. (1994) Growth factor-like effects of lysophosphatidic acid, a novel lipid mediator. Biochim. Biophys. Acta 1198, 185-196
146. Mets, S.A. (1986) Lysophosphatidylinositol, but not lysophosphatidic acid, stimulates insulin release. A possible role for phospholipase A2 but not de novo synthesis of lysophospholipid in pancreatic islet function. Biochem. Biophys. Res. Commun. 138, 720-727
147. Falasca, M. and Corda, D. (1994) Elevated levels and mitogenic activity of lysophosphatidylinositol in k-ras-transformed epithelial cells. Eur. J. Biochem. 221, 383-389
148. Horigome, K., Tamori-Natori, Y., Inoue, K., and Nojima, S. (1986) Effect of serine phospholipid structure on the enhancement of concanavalin A-induced degranulation in rat mast cells. J. Biochem. 100, 571-579
149. Bellini, F., Viola, G., Menegus, A.M., Toffano, G., and Bruni, A. (1990) Signalling mechanism in lysophosphatidylserine-induced activation of mouse mast cells. Biochim. Biophys. Acta 1052, 216-220