1,2-sn-Diacylglycerol in plant cells: Product, substrate and regulator

Plant Physiology and Biochemistry

Volumn 37, Issue 11, 1999, Pages 795-808

  Miège, Christine ^a   Maréchal, Éric ^a  

^a CEA GRENOBLE   (France)

Author keywords

Diacylglycerol; Diacylglycerol kinase; MGDG synthase; Monogalactosyldiacylglycerol; Phosphatidate phosphatase; Phosphatidic acid; Protein kinase C

Indexed keywords

EID: 0343986412     PISSN: 09819428     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0981-9428(99)00118-7     Document Type: Review

References (80)

1. Ahmed S., Kozma R., Lee J., Monfries C., Harden N., Lim L. The cysteine-rich domain of human proteins, neuronal chimaerin, protein kinase C and diacylglycerol kinase binds zinc. Evidence for the involvement of a zinc-dependent structure in phorbol ester binding. Biochem. J. 280:1991;233-241.
2. Ahmed S., Kozma R., Monfries C., Hall C., Lim H.H., Smith P., Lim L. Human n-chimaerin cDNA encodes a novel phorbol ester receptor. Biochem. J. 272:1990;767-773.
3. Ahmed S., Lee J., Kozma R., Best A., Monfries C., Lim L. A novel functional target for tumor promoting phorbol-esters and lysophosphatidic acid. The p21rac-GTPase activating protein n-chimaerin. J. Biol. Chem. 268:1993;10709-10712.
4. Bafor M., Smith M.A., Johnson L., Stobart K., Stymne S. Ricinoleic acid biosynthesis and triacylglycerol assembly in microsomal preparations from developing castor-bean (Ricinus communis) endosperm. Biochem. J. 280:1991;507-514.
5. Bhat B.G., Wang P., Coleman R.A. Hepatic monoacylglycerol acyltransferase is regulated by sn-1,2-diacylglycerol and by specific lipids in Triton X-100/phospholipid mixed micelles. J. Biol. Chem. 269:1994;13172-13178.
6. Block M.A., Dorne A.J., Joyard J., Douce R. Preparation and characterization of membrane fractions enriched in outer and inner envelope membranes from spinach chloroplasts. II-Biochemical characterization. J. Biol. Chem. 258:1983;13281-13286.
7. Bunting M., Tang W., Zimmerman G.A., McIntyre T.M., Prescott S.M. Molecular cloning and characterization of a novel human diacylglycerol kinase zeta. J. Biol. Chem. 271:1996;10230-10236.
8. Burns D.J., Bell R.M. Protein kinase C contains two phorbol ester binding domains. J. Biol. Chem. 266:1991;18330-18338.
9. Brindley D.B., Waggoner D.W. Phosphatidate phosphohydrolase and signal transduction. Chem. Physics Lipids. 80:1996;45-57.
10. Coleman R.A., Wang P., Bhat G. Fatty acids anionic phospholipids alter the palmitoyl coenzyme A kinetics of hepatic monoacylglycerol acyltransferase in Triton X-100 mixed micelles. Biochemistry. 35:1996;9576-9583.
11. Cornell R.B. Regulation of CTP:phosphocholine cytidylyltransferase by lipids. 1. Negative surface charge dependence for activation. Biochemistry. 30:1991;5873-5880.
12. Covès J., Block M.A., Joyard J., Douce R. Lipid requirement and kinetic studies of solubilized UDP-galactose:diacylglycerol galactosyltransferase activity from spinach envelope chloroplast membranes. Proc. Natl. Acad. Sci. USA. 85:1988;4966-4970.
13. 2 activity towards mixed micelles and its implication for the study of lipolytic enzymes. J. Biol. Chem. 250:1975;9013-9020.
14. Dorne A.J., Block M.A., Joyard J., Douce R. The galactolipid:galactolipid galactosyltransferase is located on the outer membrane of the chloroplast envelope. FEBS Lett. 145:1982;30-34.
15. Essen L.O., Perisic O., Cheung R., Katan M., Williams R.L. Crystal structure of a mammalian phosphoinositide-specific phospholipase Cδ Nature. 380:1996;595-602.
16. Essigmann B., Güler S., Narang R.A., Linke D., Benning C. Phosphate availability affects the thylakoid lipid composition and the expression of SQD1, a gene required for sulfolipid biosynthesis in Arabidopsis thaliana. Proc. Natl. Acad. Sci. USA. 95:1998;1950-1955.
17. Fleming I.N., Yeaman S.J. Purification and characterization of N-ethylmaleimide-insensitive phosphatidic acid phosphohydrolase (PAP2) from rat liver. Biochem. J. 308:1995;983-989.
18. Frentzen M. Acyltransferases and triacylglycerols. Moore Jr S.T. Lipid Metabolism in Plants. 1993;195-230 CRC Press, Boca Raton, Florida.
19. Ganong B.R., Loomis C.R., Hannun A.H., Bell R.M. Specificity and mechanism of protein kinase C activation by sn-1,2-diacylglycerols. Proc. Natl. Acad. Sci. USA. 83:1986;1184-1188.
20. Ghosh S., Strum J.C., Bell R.M. Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 11:1997;45-50.
21. Goldberg E.M., Zidovetzki R. Synergistic effects of diacylglycerols and fatty acids on membrane structure and protein kinase C activity. Biochemistry. 37:1998;5623-5632.
22. Hakomori S., Yamamura S., Handa A.K. Signal transduction through glyco (sphingo) lipids. Introduction and recent studies on glyco (sphingo) lipid-enriched microdomains. Ann. N. Y. Acad. Sci. 845:1998;1-10.
23. Hannun Y.A., Bell R.M. Phorbol ester binding and activation of protein kinase C on Triton X-100 mixed micelles containing phosphatidylserine. J. Biol. Chem. 261:1986;9341-9347.
24. Hansen S., Hansen L.K., Hough E. The cristal structure of Tris-inhibited phospholipase C from Bacillus cereus at 1.9 Å resolution. The nature of the metal ion in site 2. J. Mol. Biol. 231:1993;870-876.
25. Heemskerk J.H.W., Wintermans J.F.G.M. The role of the chloroplast in the leaf acyl-lipid synthesis. Physiol. Plant. 70:1987;558-568.
26. Heemskerk J.H.W., Wintermans J.F.G.M., Joyard J., Block M.A., Dorne A.J., Douce R. Localization of galactolipid:galactolipid galactosyltransferase and acyltransferase in outer envelope membrane of spinach chloroplasts. Biochim. Biophys. Acta. 877:1986;281-289.
27. Heinz E. Enzymatic reactions in galactolipid biosynthesis. Tevini M, Lichtenthaler H.K. Lipids and Lipid Polymers. 1977;102-120 Springer verlag, Berlin.
28. Heinz D.W., Essen L.O., Williams R.L. Structural and mechanistic comparison of prokaryotic and eukaryotic phosphoinositide-specific phospholipases C. J. Mol. Biol. 275:1998;635-650.
29. Hjelmstad R.H., Bell R.M. sn-1,2-Diacylglycerol choline- and ethanolamine-phosphotransferases in Saccharomyces cerevisiae, mixed micellar analysis of the CPT1 and EPT1 gene products. J. Biol. Chem. 269:1991;4357-4365.
30. Hodgkin M.N., Pettitt T.R., Martin A., Michell R.H., Pemberton A.J., Wakelam M.J. Diacylglycerols and phosphatidates: which molecular species are intracellular messengers? Trends Biochem. Sci. 23:1998;200-204.
31. James S.R., Downes C.P. Structural and mechanistic features of phospholipases C: Effects of inositol phospholipid-mediated signal transduction. Cell. Signal. 9:1997;329-336.
32. James S.R., Smith S., Paterson A., Harden T.K., McLaughlin S. Time-dependent inhibition of phospholipase C beta-catalyzed phosphoinositide hydrolysis: a comparison of different assays. Biochem. J. 314:1996;917-921.
33. Johnson J.E., Kalmar G.B., Sohal P.S., Walkey C.J., Yamashita S., Cornell R.B. Comparison of the lipid regulation of yeast and rat CTP:phosphocholine cytidylyltransferase expressed in COS cells. Biochem. J. 285:1992;815-820.
34. Joyard J., Douce R. Galactolipid biosynthesis. Stumpf P.K. The Biochemistry of Plants: Lipids, Structure and Function, vol. 9. 1987;215-274 Academic Press, New York.
35. 2+-independent phosphatidic acid phosphatase. J. Biol. Chem. 272:1997;24572-24578.
36. Kalmar G.B., Kay R.J., Lachance A., Aebersold R., Cornell R.B. Cloning and expression of rat liver CTP:phosphocholine cytidylyltransferase: an amphipatic protein that controls phosphatidylcholine synthesis. Proc. Natl. Acad. Sci. USA. 87:1990;6029-6033.
37. Kanoh H., Kai M., Wada I. Molecular properties of enzymes involved in diacylglycerol and phosphatidate metabolism. J. Lipid Mediat. Cell. Signal. 14:1996;245-250.
38. Kocsis M.G., Weselake R.J. Phosphatidate phosphatases of mammals, yeast, and higher plants. Lipids. 31:1996;785-802.
39. Lee M.Y., Bell R.M. The lipid binding regulatory domain of protein kinase C. J. Biol. Chem. 261:1986;14797-14805.
40. Lin Y.P., Carman G.M. Kinetic analysis of yeast phosphatidate phosphatase toward Triton X-100/phosphatidate mixed micelles. J. Biol. Chem. 265:1990;166-170.
41. Loomis C.R., Walsh J.P., Bell R.M. sn-1,2-Diacylglycerol kinase of Escherichia coli, purification, reconstitution, and partial amino- and carbonyl-terminal analysis. J. Biol. Chem. 260:1985;4091-4097.
42. MacDonald M.L., Mack K.F., Richardson C.N., Glomset J.A. Regulation of diacylglycerol kinase in Swiss 3T3 cells: increased phosphorylation of endogenous diacylglycerol and decreased phosphorylation of diacylglycerol in response to platelet-derived growth factor. J. Biol. Chem. 263:1988;1575-1583.
43. MacDonald M.L., Mack K.F., Williams B.W., King W.C., Glomset J.A. A membrane bound diacylglycerol kinase that selectively phosphorylates arachidonyl-diacylglycerol: distinction from cytosolic diacylglycerol kinase and comparison with the membrane-bound enzyme from Escherichia coli. J. Biol. Chem. 263:1988;1584-1592.
44. Malherbe A., Block M.A., Douce R., Joyard J. Solubilization and biochemical properties of phosphatidate phosphatase from spinach chloroplast envelope membranes. Plant Physiol. Biochem. 33:1995;149-161.
45. Maréchal E., Block M.A., Dorne A.J., Douce R., Joyard J. Lipid synthesis and metabolism in the plastid envelope. Physiol. Plant. 100:1997;65-77.
46. Maréchal E., Block M.A., Joyard J., Douce R. Kinetic properties of MGDG synthase from spinach chloroplast envelope membranes. J. Biol. Chem. 269:1994;5788-5798.
47. Maréchal E., Miège C., Block M.A., Douce R., Joyard J. The catalytic site of MGDG synthase from spinach chloroplast envelope: A biochemical study of the structure and metal content. J. Biol. Chem. 270:1995;5714-5722.
48. Maroney A.C., Macara J.C. Translocation of diacylglycerol kinase from the cytosol to the membrane in phorbol ester-treated Swiss 3T3 fibroblasts. J. Cell. Biochem. 40:1989;165-172.
49. McMaster C.R., Morash S.C., Bell R.M. Phospholipid and cation activation of chimaeric choline/ethanolamine phosphotransferases. Biochem. J. 313:1996;729-735.
50. Mott H.R., Carpenter J.W., Zhong S., Ghosh S., Bell R.M., Campbell S. The solution structure of the Raf-1 cysteine-rich domain: a novel Ras and phospholipid binding site. Proc. Natl. Acad. Sci. USA. 93:1996;8312-8317.
51. Newton A.C. Regulation of protein kinase C. Curr. Opin. Cell Biol. 9:1997;161-167.
52. Nishizuka Y. Protein kinase C and lipid signaling for sustained cellular response. FASEB J. 9:1995;484-496.
53. Pettitt T.R., Wakelam M.J. Distinct phospholipases C-regulated signalling pathways in Swiss 3T3 fibroblasts induce the rapid generation of the same polyunsaturated diacylglycerols. FEBS Lett. 427:1998;371-376.
54. Quest A.F.G., Bardes E.S.G., Bell R.M. A phorbol ester binding domain of protein kinase Cγ: Deletion analysis of the Cys2 domain defines a minimal 43 amino acid peptide. J. Biol. Chem. 269:1994;2961-2970.
55. Rhee S.G., Bae Y.S. Regulation of phosphoinositide-specific phospholipase C isoenzymes. J. Biol. Chem. 272:1997;15045-15048.
56. Roberts R., Sciorra V.A., Morris A.J. Human type 2 phosphatidic acid phosphohydrolases. Substrate specificity of the type 2a, 2b and 2c enzymes and cell surface activity of the 2a isoform. J. Biol. Chem. 273:1998;22059-22067.
57. Sakaki T., Kondo N., Yamada M. Pathway for the synthesis of triacylglycerol from monogalactosyldiacylglycerols in ozone-fumigated spinach leaves. Plant Physiol. 94:1990;773-780.
58. Sakane F., Kai M., Wada I., Imai S., Kanoh H. The C-terminal part of diacylglycerol kinase α lacking zinc fingers serves as a catalytic domain. Biochem. J. 318:1996;583-590.
59. Sakane F., Yamada K., Imai S.I., Kanoh I. Porcine 80-kDa diacylglycerol kinase is a calcium-binding and calcium/phospholipid-dependent enzyme and undergoes calcium-dependent translocation. J. Biol. Chem. 266:1991;7096-7100.
60. Sakane F., Yamada K., Kanoh H., Yokoyama C., Tanabe T. Porcine diacylglycerol sequence has a zinc finger and a E-F hand motifs. Nature. 344:1990;345-348.
61. 2+ oscillations induced in single hepatocytes. FEBS Lett. 312:1992;57-60.
62. Sanders C.R., Czerski L., Vinogradova O., Badola P., Song D., Smith S.O. Escherichia coli diacylglycerol kinase is a α-helical polytopic membrane protein and can spontaneously insert into preformed lipid vesicles. Biochemistry. 35:1996;8610-8618.
63. Schneider E.G., Kennedy R.S. Partial purification and properties of diglyceride kinase from Escherichia coli. Biochim. Biophys. Acta. 441:1976;201-212.
64. Seifert U., Heinz E. Enzymatic characteristics of UDP-sulfoquinovose:diacylglycerol sulfoquinovosyltransferase from chloroplast envelope. Bot. Acta. 105:1992;197-205.
65. Shimojima M., Ohta H., Iwamatsu A., Masuda T., Shioi Y., Takamiya K.I. Cloning of the gene of monogalactosyldiacylglycerol synthase and its evolutionary origin. Proc. Natl. Acad. Sci. USA. 94:1997;333-337.
66. Tang W., Bunting M., Zimmerman G.A., McIntyre T.M., Prescott S.M. Molecular cloning of a novel human diacylglycerol kinase highly selective for arachidonate-containing substrates. J. Biol. Chem. 271:1996;10237-10241.
67. Tolias K.F., Couvillon A.D., Cantley L.C., Carpenter C.L. Characterization of Rac1- and RhoGDI-associated lipid kinase signaling complex. Mol. Cell. Biol. 18:1998;762-770.
68. Tronchère H., Record M., Tercé F., Chap H. Phosphatidylcholine cycle and regulation of phosphatidylcholine biosynthesis by enzyme translocation. Biochim. Biophys. Acta. 1212:1994;137-151.
69. Van der Bend R.L., de Widt J., Hilfmann H., van Blitterswijk W. Diacylglycerol kinase in receptor-stimulated cells converts its substrate in a topologically restricted manner. J. Biol. Chem. 269:1994;4098-4102.
70. Vogel G., Browse J. Choline phosphotransferase and diacylglycerol acyltransferase. Substrate specificities at a key branch point in seed lipid metabolism. Plant Physiol. 110:1996;923-931.
71. Waggoner D.W., Gomes-Munõz A., Dewald J., Brindley D.N. Phosphatidate phosphohydrolase catalyses the hydrolysis of ceramide 1-phosphate, lysophosphatidate, and sphingosine 1-phosphate. J. Biol. Chem. 271:1996;16506-16509.
72. Wakelam M.J.O. Diacylglycerol - when is it an intracellular messenger? Biochim. Biophys. Acta. 1438:1998;117-126.
73. Walsh J.P., Bell R.M. sn-1,2-Diacylglycerol kinase of Escherichia coli. Mixed micellar analysis of the phospholipid cofactor requirement and divalent cation dependence. J. Biol. Chem. 261:1986;6239-6247.
74. Walsh J.P., Bell R.M. sn-1,2-Diacylglycerol kinase of Escherichia coli. Structural and kinetic analysis of the lipids cofactor dependence. J. Biol. Chem. 261:1986;15062-15069.
75. Walsh J.P., Fahrner L., Bell R.M. sn-1,2-Diacylglycerol kinase of Escherichia coli. Diacylglycerol analogues define specificity and mechanism. J. Biol. Chem. 265:1990;4374-4381.
76. Walsh J.P., Suen R., Lamaitre R.N., Glomset J.A. Arachidonoyl-diacylglycerol kinase from bovine testis. Purification and properties. J. Biol. Chem. 269:1994;21155-21164.
77. Wang S., Kazanietz M.G., Blumberg P.M., Marquez V.E., Milne G.W. Molecular modeling and site-directed mutagenesis studies of a phorbol ester-binding site in protein kinase C. J. Med. Chem. 39:1996;2541-2553.
78. Wu W.I., Carman G.M. Regulation of phosphatidate phosphatase activity from the yeast Saccharomyces cerevisiae by phospholipids. Biochemistry. 35:1996;3790-3796.
79. Zhang G., Kazanietz M.G., Blumberg P., Hurley J.H. Crystal structure of the Cys2 activator binding domain of protein kinase C delta in complex with phorbol ester. Cell. 81:1995;917-924.
80. Zhou C., Roberts M.F. Diacylglycerol partitioning and mixing in detergent micelles: relevance to enzyme kinetics. Biochim. Biophys. Acta. 1348:1997;273-286.