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Chemical Compound Review

phosphatidic acids     2,3- dimethanoyloxypropoxyphosphoni c acid

Synonyms: AC1NUST0, CHEBI:16337, (2-formyloxy-3-phosphonooxypropyl) formate
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Disease relevance of phosphatidic acids

  • Secretion under these conditions is not accompanied by PA formation and is resistant both to depletion of Ca2+ from internal stores and to pertussis toxin (PtX) treatment [1].
  • Pharmacological inhibition of synthesis of selected PA species may therefore provide a therapeutic approach to suppression of HIV replication [2].
  • We have investigated whether the activity of the N-ethylmaleimide-sensitive ("metabolic") form of phosphatidate phosphohydrolase is increased in patients with alcoholic liver disease and whether any increased activity correlates with the severity of steatosis [3].
  • The activity of the metabolic form of hepatic phosphatidate phosphohydrolase correlates with the severity of alcoholic fatty liver in human beings [3].
  • DGPP phosphatases (DGPP phosphohydrolase) from Saccharomyces cerevisiae and Escherichia coli catalyze the dephosphorylation of DGPP to yield phosphatidate (PA) and then catalyze the dephosphorylation of PA to yield diacylglycerol [4].

Psychiatry related information on phosphatidic acids


High impact information on phosphatidic acids


Chemical compound and disease context of phosphatidic acids

  • CT-2576 suppressed both PA generation induced by Tat and HIV long terminal repeat-directed gene expression in response to Tat or TNF-alpha at a posttranscriptional step [2].
  • We have previously demonstrated that if C62B glioma cells are prelabeled with [1-14C]arachidonate, cholinergic stimulation results in liberation of radioactive arachidonate and accumulation of radioactive phosphatidate [10].
  • Surprisingly, phosphatidic acid (PA), which did not induce increases in [Ca2+]i, p125FAK activation or activation of MAP kinases, did induce proliferation of ovarian cancer cells, albeit at higher concentrations that LPA [11].
  • These data indicate that the development of fatty liver as an effect of 3-tetradecylpropionic acid is probably due to accelerated triglyceride biosynthesis, which is mediated by an increase in the availability of fatty acid along with stimulation of phosphatidate phosphohydrolase [12].
  • Additional findings included elevated levels of PC for glioblastoma multiforme relative to neurofibroma, and neurilemmoma was differentiated from neurofibroma with elevated levels of PA and depressed levels of PI [13].

Biological context of phosphatidic acids

  • Phagocytosis of either Erdman or H37Ra M. tuberculosis in the presence of autologous non-immune serum was associated with a 2.5-3-fold increase in phosphatidic acid (PA) [14].
  • Phosphatidate (PA) is a central metabolite of lipid metabolism and a signaling molecule in many eukaryotes, including plants [15].
  • Cellular activation in lymphoid cells is associated with augmented accumulation of certain phosphatidic acid (PA) species derived from the hydrolysis of glycan phosphatidylinositol (GPI) [2].
  • Phosphatidate-dependent phosphorylation of a 30-kDa protein in the soluble fraction from heart was also observed [16].
  • To test this hypothesis, we examined the effect of tat gene expression on the production of cellular PA species, as the Tat protein is essential for HIV expression and has been implicated in activating the expression of multiple host cellular genes [2].

Anatomical context of phosphatidic acids


Associations of phosphatidic acids with other chemical compounds


Gene context of phosphatidic acids


Analytical, diagnostic and therapeutic context of phosphatidic acids


  1. Exocytosis in mast cells by basic secretagogues: evidence for direct activation of GTP-binding proteins. Aridor, M., Traub, L.M., Sagi-Eisenberg, R. J. Cell Biol. (1990) [Pubmed]
  2. CT-2576, an inhibitor of phospholipid signaling, suppresses constitutive and induced expression of human immunodeficiency virus. Leung, D.W., Peterson, P.K., Weeks, R., Gekker, G., Chao, C.C., Kaplan, A.H., Balantac, N., Tompkins, C., Underiner, G.E., Bursten, S. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  3. The activity of the metabolic form of hepatic phosphatidate phosphohydrolase correlates with the severity of alcoholic fatty liver in human beings. Day, C.P., James, O.F., Brown, A.S., Bennett, M.K., Fleming, I.N., Yeaman, S.J. Hepatology (1993) [Pubmed]
  4. Mammalian Mg2+-independent phosphatidate phosphatase (PAP2) displays diacylglycerol pyrophosphate phosphatase activity. Dillon, D.A., Chen, X., Zeimetz, G.M., Wu, W.I., Waggoner, D.W., Dewald, J., Brindley, D.N., Carman, G.M. J. Biol. Chem. (1997) [Pubmed]
  5. The activities of lipoprotein lipase and of enzymes involved in triacylglycerol synthesis in rat adipose tissue. Effects of starvation, dietary modification and of corticotropin injection. Lawson, N., Pollard, A.D., Jennings, R.J., Gurr, M.I., Brindley, D.N. Biochem. J. (1981) [Pubmed]
  6. Phosphatidate, phosphatidylinositol, diacylglycerols, and free fatty acids in the brain following electroshock, anoxia, or ischemia. de Turco, E.B., Cascone, G.D., Pediconi, M.F., Bazán, N.G. Adv. Exp. Med. Biol. (1977) [Pubmed]
  7. Porcine diacylglycerol kinase sequence has zinc finger and E-F hand motifs. Sakane, F., Yamada, K., Kanoh, H., Yokoyama, C., Tanabe, T. Nature (1990) [Pubmed]
  8. Proposed mechanism of cholinergic action in smooth muscle. Salmon, D.M., Honeyman, T.W. Nature (1980) [Pubmed]
  9. Mechanism of GnRH receptor signaling: combinatorial cross-talk of Ca2+ and protein kinase C. Naor, Z., Harris, D., Shacham, S. Frontiers in neuroendocrinology. (1998) [Pubmed]
  10. Glucocorticoids inhibit the liberation of arachidonate but not the rapid production of phospholipase C-dependent metabolites in acetylcholine-stimulated C62B glioma cells. DeGeorge, J.J., Ousley, A.H., McCarthy, K.D., Morell, P., Lapetina, E.G. J. Biol. Chem. (1987) [Pubmed]
  11. Lysophospholipids activate ovarian and breast cancer cells. Xu, Y., Fang, X.J., Casey, G., Mills, G.B. Biochem. J. (1995) [Pubmed]
  12. Regulation of fatty acid oxidation and triglyceride and phospholipid metabolism by hypolipidemic sulfur-substituted fatty acid analogues. Skorve, J., Asiedu, D., Rustan, A.C., Drevon, C.A., al-Shurbaji, A., Berge, R.K. J. Lipid Res. (1990) [Pubmed]
  13. 31P NMR phospholipid characterization of intracranial tumors. Merchant, T.E., van der Ven, L.T., Minsky, B.D., Diamantis, P.M., Delapaz, R., Galicich, J., Glonek, T. Brain Res. (1994) [Pubmed]
  14. Activation of phospholipase D is tightly coupled to the phagocytosis of Mycobacterium tuberculosis or opsonized zymosan by human macrophages. Kusner, D.J., Hall, C.F., Schlesinger, L.S. J. Exp. Med. (1996) [Pubmed]
  15. Mutation of the TGD1 chloroplast envelope protein affects phosphatidate metabolism in Arabidopsis. Xu, C., Fan, J., Froehlich, J.E., Awai, K., Benning, C. Plant Cell (2005) [Pubmed]
  16. Phosphatidate-dependent protein phosphorylation. Bocckino, S.B., Wilson, P.B., Exton, J.H. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  17. Roles of phosphatidate phosphatase enzymes in lipid metabolism. Carman, G.M., Han, G.S. Trends Biochem. Sci. (2006) [Pubmed]
  18. Evidence that phospholipase D mediates ADP ribosylation factor-dependent formation of Golgi coated vesicles. Ktistakis, N.T., Brown, H.A., Waters, M.G., Sternweis, P.C., Roth, M.G. J. Cell Biol. (1996) [Pubmed]
  19. Ubiquitous and endoplasmic reticulum-located lysophosphatidyl acyltransferase, LPAT2, is essential for female but not male gametophyte development in Arabidopsis. Kim, H.U., Li, Y., Huang, A.H. Plant Cell (2005) [Pubmed]
  20. Electrospray ionization mass spectrometry analysis of changes in phospholipids in RBL-2H3 mastocytoma cells during degranulation. Ivanova, P.T., Cerda, B.A., Horn, D.M., Cohen, J.S., McLafferty, F.W., Brown, H.A. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  21. Activation of phospholipase D by interleukin-8 in human neutrophils. Sozzani, S., Agwu, D.E., Ellenburg, M.D., Locati, M., Rieppi, M., Rojas, A., Mantovani, A., McPhail, L.C. Blood (1994) [Pubmed]
  22. Phospholipase D-mediated diradylglycerol formation coincides with H2O2 and lactoferrin release in adherent human neutrophils. Suchard, S.J., Nakamura, T., Abe, A., Shayman, J.A., Boxer, L.A. J. Biol. Chem. (1994) [Pubmed]
  23. Involvement of phospholipase D2 in lysophosphatidate-induced transactivation of platelet-derived growth factor receptor-beta in human bronchial epithelial cells. Wang, L., Cummings, R., Zhao, Y., Kazlauskas, A., Sham, J.K., Morris, A., Georas, S., Brindley, D.N., Natarajan, V. J. Biol. Chem. (2003) [Pubmed]
  24. Isolation and characterization of the Saccharomyces cerevisiae LPP1 gene encoding a Mg2+-independent phosphatidate phosphatase. Toke, D.A., Bennett, W.L., Oshiro, J., Wu, W.I., Voelker, D.R., Carman, G.M. J. Biol. Chem. (1998) [Pubmed]
  25. ARF and PITP restore GTP gamma S-stimulated protein secretion from cytosol-depleted HL60 cells by promoting PIP2 synthesis. Fensome, A., Cunningham, E., Prosser, S., Tan, S.K., Swigart, P., Thomas, G., Hsuan, J., Cockcroft, S. Curr. Biol. (1996) [Pubmed]
  26. Phospholipase D2 functions as a downstream signaling molecule of MAP kinase pathway in L1-stimulated neurite outgrowth of cerebellar granule neurons. Watanabe, H., Yamazaki, M., Miyazaki, H., Arikawa, C., Itoh, K., Sasaki, T., Maehama, T., Frohman, M.A., Kanaho, Y. J. Neurochem. (2004) [Pubmed]
  27. Molecular species analysis of a product of phospholipase D activation. Phosphatidylethanol is formed from phosphatidylcholine in phorbol ester- and bradykinin-stimulated PC12 cells. Holbrook, P.G., Pannell, L.K., Murata, Y., Daly, J.W. J. Biol. Chem. (1992) [Pubmed]
  28. Kinetics and thermodynamics of calcium-induced lateral phase separations in phosphatidic acid containing bilayers. Graham, I., Gagné, J., Silvius, J.R. Biochemistry (1985) [Pubmed]
  29. Mechanisms for the effects of ethanol on hepatic phosphatidate phosphohydrolase. Savolainen, M.J., Hassinen, I.E. Biochem. J. (1978) [Pubmed]
  30. Membrane trapping of carbon-11-labeled 1,2-diacylglycerols as a basic concept for assessing phosphatidylinositol turnover in neurotransmission process. Imahori, Y., Fujii, R., Ueda, S., Matsumoto, K., Wakita, K., Ido, T., Nariai, T., Nakahashi, H. J. Nucl. Med. (1992) [Pubmed]
  31. Sympathetic denervation impairs agonist-stimulated phosphatidylinositol metabolism in rat parotid glands. Downes, C.P., Dibner, M.D., Hanley, M.R. Biochem. J. (1983) [Pubmed]
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