The glycerophospho metabolome and its influence on amino acid homeostasis revealed by brain metabolomics of GDE1(-/-) mice

Chemistry and Biology

Volumn 17, Issue 8, 2010, Pages 831-840

  Kopp, Florian ^a   Komatsu, Toru ^a   Nomura, Daniel K ^a   Trauger, Sunia A ^a   Thomas, Jason R ^a   Siuzdak, Gary ^a   Simon, Gabriel M ^a,b   Cravatt, Benjamin F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

CHEMBIO; SYSBIO; SYSNEURO

Indexed keywords

AMINO ACID; GLYCEROPHOSPHODIESTER PHOSPHODIESTERASE; GLYCERYLPHOSPHOINOSITOL; INOSITOL PHOSPHATE; PHOSPHODIESTERASE; SERINE; WATER;

ANIMAL; ARTICLE; BRAIN; CHEMISTRY; CYTOLOGY; HOMEOSTASIS; MALE; MASS SPECTROMETRY; METABOLISM; METABOLOME; METABOLOMICS; METHODOLOGY; MOUSE; SOLUBILITY;

AMINO ACIDS; ANIMALS; BRAIN; HOMEOSTASIS; INOSITOL PHOSPHATES; MALE; MASS SPECTROMETRY; METABOLOME; METABOLOMICS; MICE; PHOSPHORIC DIESTER HYDROLASES; SERINE; SOLUBILITY; WATER;

EUKARYOTA; MAMMALIA; MUS;

EID: 77956043214     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2010.06.009     Document Type: Article

References (53)

1. S.U. Bajad, W. Lu, E.H. Kimball, J. Yuan, C. Peterson, and J.D. Rabinowitz Separation and quantitation of water soluble cellular metabolites by hydrophilic interaction chromatography-tandem mass spectrometry J. Chromatogr. A 1125 2006 76 88
2. A.C. Basu, G.E. Tsai, C.L. Ma, J.T. Ehmsen, A.K. Mustafa, L. Han, Z.I. Jiang, M.A. Benneyworth, M.P. Froimowitz, and N. Lange Targeted disruption of serine racemase affects glutamatergic neurotransmission and behavior Mol. Psychiatry 14 2009 719 727
3. H.P. Benton, D.M. Wong, S.A. Trauger, and G. Siuzdak XCMS2: processing tandem mass spectrometry data for metabolite identification and structural characterization Anal. Chem. 80 2008 6382 6389
4. K.P. Chiang, S. Niessen, A. Saghatelian, and B.F. Cravatt An enzyme that regulates ether lipid signaling pathways in cancer annotated by multidimensional profiling Chem. Biol. 13 2006 1041 1050
5. D. Corda, T. Kudo, P. Zizza, C. Iurisci, E. Kawai, N. Kato, N. Yanaka, and S. Mariggio The developmentally regulated osteoblast phosphodiesterase GDE3 is glycerophosphoinositol-specific and modulates cell growth J. Biol. Chem. 284 2009 24848 24856
6. D. Corda, P. Zizza, A. Varone, B.M. Filippi, and S. Mariggio The glycerophosphoinositols: cellular metabolism and biological functions Cell. Mol. Life Sci. 66 2009 3449 3467
7. L. Dang, D.W. White, S. Gross, B.D. Bennett, M.A. Bittinger, E.M. Driggers, V.R. Fantin, H.G. Jang, S. Jin, and M.C. Keenan Cancer-associated IDH1 mutations produce 2-hydroxyglutarate Nature 462 2009 739 744
8. T.J. de Koning, and L.W. Klomp Serine-deficiency syndromes Curr. Opin. Neurol. 17 2004 197 204
9. S.R. Dowd, M.E. Bier, and J.L. Patton-Vogt Turnover of phosphatidylcholine in Saccharomyces cerevisiae. The role of the CDP-choline pathway J. Biol. Chem. 276 2001 3756 3763
10. A. Emilsson, and R. Sundler Differential activation of phosphatidylinositol deacylation and a pathway via diphosphoinositide in macrophages responding to zymosan and ionophore A23187 J. Biol. Chem. 259 1984 3111 3116
11. M. Falasca, M. Marino, A. Carvelli, C. Iurisci, S. Leoni, and D. Corda Changes in the levels of glycerophosphoinositols during differentiation of hepatic and neuronal cells Eur. J. Biochem. 241 1996 386 392
12. M. Falasca, A. Carvelli, C. Iurisci, R.G. Qiu, M.H. Symons, and D. Corda Fast receptor-induced formation of glycerophosphoinositol-4-phosphate, a putative novel intracellular messenger in the Ras pathway Mol. Biol. Cell 8 1997 443 453
13. E. Fisher, C. Almaguer, R. Holic, P. Griac, and J. Patton-Vogt Glycerophosphocholine-dependent growth requires Gde1p (YPL110c) and Git1p in Saccharomyces cerevisiae J. Biol. Chem. 280 2005 36110 36117
14. S. Furuya, T. Tabata, J. Mitoma, K. Yamada, M. Yamasaki, A. Makino, T. Yamamoto, M. Watanabe, M. Kano, and Y. Hirabayashi L-serine and glycine serve as major astroglia-derived trophic factors for cerebellar Purkinje neurons Proc. Natl. Acad. Sci. USA 97 2000 11528 11533
15. M. Gallazzini, J.D. Ferraris, and M.B. Burg GDPD5 is a glycerophosphocholine phosphodiesterase that osmotically regulates the osmoprotective organic osmolyte GPC Proc. Natl. Acad. Sci. USA 105 2008 11026 11031
16. T.A. Garrett, C.R. Raetz, T. Richardson, R. Kordestani, J.D. Son, and R.L. Rose Identification of phosphatidylserylglutamate: a novel minor lipid in Escherichia coli J. Lipid Res. 50 2009 1589 1599
17. Z. Guan, S. Li, D.C. Smith, W.A. Shaw, and C.R. Raetz Identification of N-acylphosphatidylserine molecules in eukaryotic cells Biochemistry 46 2007 14500 14513
18. C. Henneberger, T. Papouin, S.H. Oliet, and D.A. Rusakov Long-term potentiation depends on release of D-serine from astrocytes Nature 463 2010 232 236
19. R. Inoue, K. Hashimoto, T. Harai, and H. Mori NMDA- and beta-amyloid1-42-induced neurotoxicity is attenuated in serine racemase knock-out mice J. Neurosci. 28 2008 14486 14491
20. P.T. Ivanova, S.B. Milne, D.S. Myers, and H.A. Brown Lipidomics: a mass spectrometry based systems level analysis of cellular lipids Curr. Opin. Chem. Biol. 13 2009 526 531
21. A.U. Jackson, S.R. Werner, N. Talaty, Y. Song, K. Campbell, R.G. Cooks, and J.A. Morgan Targeted metabolomic analysis of Escherichia coli by desorption electrospray ionization and extractive electrospray ionization mass spectrometry Anal. Biochem. 375 2008 272 281
22. P. Klivenyi, K.A. Kekesi, Z. Hartai, G. Juhasz, and L. Vecsei Effects of mitochondrial toxins on the brain amino acid concentrations Neurochem. Res. 30 2005 1421 1427
23. T.J. Larson, M. Ehrmann, and W. Boos Periplasmic glycerophosphodiester phosphodiesterase of Escherichia coli, a new enzyme of the glp regulon J. Biol. Chem. 258 1983 5428 5432
24. C.L. Lencina, A. Dassonville-Klimpt, and P. Sonnet New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines Tetrahedron Asymmetry 19 2008 1689 1697
25. S. Mariggio, C. Iurisci, J. Sebastia, J. Patton-Vogt, and D. Corda Molecular characterization of a glycerophosphoinositol transporter in mammalian cells FEBS Lett. 580 2006 6789 6796
26. S.J. Martin, C.P. Reutelingsperger, A.J. McGahon, J.A. Rader, R.C. van Schie, D.M. LaFace, and D.R. Green Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl J. Exp. Med. 182 1995 1545 1556
27. D.J. McNally, J.P. Hui, A.J. Aubry, K.K. Mui, P. Guerry, J.R. Brisson, S.M. Logan, and E.C. Soo Functional characterization of the flagellar glycosylation locus in Campylobacter jejuni 81-176 using a focused metabolomics approach J. Biol. Chem. 281 2006 18489 18498
28. D.J. McNally, A.J. Aubry, J.P. Hui, N.H. Khieu, D. Whitfield, C.P. Ewing, P. Guerry, J.R. Brisson, S.M. Logan, and E.C. Soo Targeted metabolomics analysis of Campylobacter coli VC167 reveals legionaminic acid derivatives as novel flagellar glycans J. Biol. Chem. 282 2007 14463 14475
29. J.P. Mothet, A.T. Parent, H. Wolosker, R.O. Brady Jr., D.J. Linden, C.D. Ferris, M.A. Rogawski, and S.H. Snyder D-serine is an endogenous ligand for the glycine site of the N-methyl-D-aspartate receptor Proc. Natl. Acad. Sci. USA 97 2000 4926 4931
30. J.P. Murray, and C.R. McMaster Nte1p-mediated deacylation of phosphatidylcholine functionally interacts with Sec14p J. Biol. Chem. 280 2005 8544 8552
31. Y. Nagata, K. Horiike, and T. Maeda Distribution of free D-serine in vertebrate brains Brain Res. 634 1994 291 295
32. J. Patton-Vogt Transport and metabolism of glycerophosphodiesters produced through phospholipid deacylation Biochim. Biophys. Acta 1771 2007 337 342
33. J.L. Patton-Vogt, and S.A. Henry GIT1, a gene encoding a novel transporter for glycerophosphoinositol in Saccharomyces cerevisiae Genetics 149 1998 1707 1715
34. J.D. Rabinowitz, and E. Kimball Acidic acetonitrile for cellular metabolome extraction from Escherichia coli Anal. Chem. 79 2007 6167 6173
35. M. Rao, and S. Sockanathan Transmembrane protein GDE2 induces motor neuron differentiation in vivo Science 309 2005 2212 2215
36. A. Saghatelian, S.A. Trauger, E.J. Want, E.G. Hawkins, G. Siuzdak, and B.F. Cravatt Assignment of endogenous substrates to enzymes by global metabolite profiling Biochemistry 43 2004 14332 14339
37. G.M. Simon, and B.F. Cravatt Endocannabinoid biosynthesis proceeding through glycerophospho-N-acyl ethanolamine and a role for alpha/beta-hydrolase 4 in this pathway J. Biol. Chem. 281 2006 26465 26472
38. G.M. Simon, and B.F. Cravatt Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain J. Biol. Chem. 283 2008 9341 9349
39. G.M. Simon, and B.F. Cravatt Characterization of mice lacking candidate N-acyl ethanolamine biosynthetic enzymes provides evidence for multiple pathways that contribute to endocannabinoid production in vivo Mol. Biosyst. 6 2010 1411 1418
40. C.A. Smith, E.J. Want, G. O'Maille, R. Abagyan, and G. Siuzdak XCMS: processing mass spectrometry data for metabolite profiling using nonlinear peak alignment, matching, and identification Anal. Chem. 78 2006 779 787
41. S.H. Snyder, and P.M. Kim D-amino acids as putative neurotransmitters: focus on D-serine Neurochem. Res. 25 2000 553 560
42. D.M. Tagore, W.M. Nolte, J.M. Neveu, R. Rangel, L. Guzman-Rojas, R. Pasqualini, W. Arap, W.S. Lane, and A. Saghatelian Peptidase substrates via global peptide profiling Nat. Chem. Biol. 5 2009 23 25
43. Z. Tang, M.V. Martin, and F.P. Guengerich Elucidation of functions of human cytochrome P450 enzymes: identification of endogenous substrates in tissue extracts using metabolomic and isotopic labeling approaches Anal. Chem. 81 2009 3071 3078
44. J. Tommassen, K. Eiglmeier, S.T. Cole, P. Overduin, T.J. Larson, and W. Boos Characterization of two genes, glpQ and ugpQ, encoding glycerophosphoryl diester phosphodiesterases of Escherichia coli Mol. Gen. Genet. 226 1991 321 327
45. N. Vinayavekhin, and A. Saghatelian Regulation of alkyl-dihydrothiazole- carboxylates (ATCs) by iron and the pyochelin gene cluster in Pseudomonas aeruginosa ACS Chem. Biol. 4 2009 617 623
46. H. Wolosker, S. Blackshaw, and S.H. Snyder Serine racemase: a glial enzyme synthesizing D-serine to regulate glutamate-N-methyl-D-aspartate neurotransmission Proc. Natl. Acad. Sci. USA 96 1999 13409 13414
47. T. Yamamoto, I. Nishizaki, S. Furuya, Y. Hirabayashi, K. Takahashi, S. Okuyama, and H. Yamamoto Characterization of rapid and high-affinity uptake of L-serine in neurons and astrocytes in primary culture FEBS Lett. 548 2003 69 73
48. M. Yamasaki, K. Yamada, S. Furuya, J. Mitoma, Y. Hirabayashi, and M. Watanabe 3-Phosphoglycerate dehydrogenase, a key enzyme for l-serine biosynthesis, is preferentially expressed in the radial glia/astrocyte lineage and olfactory ensheathing glia in the mouse brain J. Neurosci. 21 2001 7691 7704
49. Y. Yan, P. Sabharwal, M. Rao, and S. Sockanathan The antioxidant enzyme Prdx1 controls neuronal differentiation by thiol-redox-dependent activation of GDE2 Cell 138 2009 1209 1221
50. N. Yanaka Mammalian glycerophosphodiester phosphodiesterases Biosci. Biotechnol. Biochem. 71 2007 1811 1818
51. N. Yanaka, Y. Imai, E. Kawai, H. Akatsuka, K. Wakimoto, Y. Nogusa, N. Kato, H. Chiba, E. Kotani, and K. Omori Novel membrane protein containing glycerophosphodiester phosphodiesterase motif is transiently expressed during osteoblast differentiation J. Biol. Chem. 278 2003 43595 43602
52. B. Zheng, D. Chen, and M.G. Farquhar MIR16, a putative membrane glycerophosphodiester phosphodiesterase, interacts with RGS16 Proc. Natl. Acad. Sci. USA 97 2000 3999 4004
53. B. Zheng, C.P. Berrie, D. Corda, and M.G. Farquhar GDE1/MIR16 is a glycerophosphoinositol phosphodiesterase regulated by stimulation of G protein-coupled receptors Proc. Natl. Acad. Sci. USA 100 2003 1745 1750