Identification of plant sphingolipid desaturases using chromatography and mass spectrometry

Journal of Chromatographic Science

Volumn 47, Issue 10, 2009, Pages 895-901

  Sun, Dayong ^a   Froman, Byron E ^a   Orth, Robert G ^a   MacIsaac, Susan A ^a   Larosa, Thomas ^a   Dong, Fenggao ^a   Valentin, Henry E ^a  

^a MONSANTO COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70450191455     PISSN: 00219665     EISSN: None     Source Type: Journal    
DOI: 10.1093/chromsci/47.10.895     Document Type: Article

References (45)

1. Y.A. Hannun and L.M. Obeid. Principles of Bioactive Lipid Signaling: Lessons from Sphingolipids. Nature Rev. Molecular Cell Bio. 9: 139-150 (2008).
2. R.C. Dickson. Thematic Review Series: Sphingolipids. New Insights into Sphingolipid Metabolism and Function in Budding Yeast. J. Lipid Res. 49: 909-921 (2008).
3. S.T. Pruett, A. Bushnev, K. Hagedorn, M. Adiga, C.A. Haynes, M.C. Sullards, D.C. Liotta, and A.H. Jr. Merrill. Thematic Review Series: Sphingolipids. Biodiversity of Sphingoid Bases ("Sphingosines") and Related Amino Alcohols. J. Lipid Res. 49: 1621-1639 (2008).
4. H. Jr. Merrill, M.D. Wang, M. Park, and M.C. Sullards. (Glyco)sphingolipidology: An Amazing Challenge and Opportunity for Systems Biology. Trends in Biochem. Sci. 10: 457-468 (2007).
5. M. Chen, G. Han, C.R. Dietrich, T.M. Dunn, and E.B. Cahoon. The Essential Nature of Sphingolipids in Plants as Revealed by the Functional Identification and Characterization of the Arabidopsis LCB1 Subunit of Serine Palmitoyltransferase. Plant Cell. 18: 3576-3593 (2006).
6. M. Chen, J.E. Markham, C.R. Dietrich, J.G. Jaworski, and E.B. Cahoon. Sphingolipid Long-Chain Base Hydroxylation Is (important for Growth and Regulation of Sphingolipid Content and Composition in Arabidopsis. Plant Cell 20: 1862-1878 (2008).
7. V. Ramamoorthy, E.B. Cahoon, M. Thokala, J. Kaur, J. Li, and D.M. Shah. Sphingolipid C9-Methyltransferases Are Important for Growth and Virulence but not for Sensitivity to Antifungal Plant Defensins in Fusarium graminearum. Eukaryotic Cell 8: 217-229 (2009).
8. G.D'. Angelo, E. Polishchuk, G. Di Tullio, M. Santoro, A. Di Campli, A. Godi, G. West, J. Bielawski, C.C. Chuang, A.C. van der Spoel, F.M. Platt, Y.A. Hannun, R. Polishchuk, P. Mattjus, and M.A. De Matteis. Glycosphingolipid Synthesis Requires FAPP2 Transfer of Glucosylceramide. Nature 449: 62-67 (2007).
9. K. Sims, S. Spassieva, E. Voit, and L. Obeid, Yeast Sphingolipid Metabolism: Clues and Connections. Biochem. Cell Biol. 82: 45-61 (2004).
10. R.P. Rao, C. Yuan, J.C. Allegood, S.S. Rawat, M.B. Edwards, X. Wang, A.H. Jr. Merrill, U. Acharya, and J.K. Acharya. Ceramide Transfer Protein Function is Essential for Normal Oxidative Stress Response and Lifespan. Proc. Nat. Acad. Sci. USA 104: 11364-11369 (2007).
11. W.L. Holland and S.A. Summers. Sphingolipids, Insulin Resistance, and Metabolic Disease: New Insights from in vivo Manipulation of Sphingolipid Metabolism. Endocrine Rev. 29: 381-402 (2008).
12. E. Alewijnse and S.L. Peters. Sphingolipid Signaling in the Cardiovascular System: Good, Bad or Both? Eur. J. Pharm. 585: 292-302 (2008).
13. L.D. Williams, A.E. Glenn, A.M. Zimeri, C. W. Bacon, M.A. Smith, and R.T. Riley. Fumonisin Disruption of Ceramide Biosynthesis in Maize Roots and the Effects on Plant Development and Fusarium Verticillioides-induced Seedling Disease. J. Agr. Food Chem. 55: 2937-2946 (2007).
14. P. Sperling, S. Franke, S. Lüthje, and E. Heinz. Are Glucocerebrosides the Predominant Sphingolipids in Plant Plasma Membranes? Plant Phys. Biochem. 42(12): 1-7 (2005).
15. G. Jenkins, A. Richards, T. Wahl, G. Mao, L. Obeid, and Y. Hannun. Involvement of Yeast Sphinogolipids in the Heat Stress Response of Saccharomyces cervisiae. J. Bio. Chem. 272: 32,566-32,572 (1997).
16. P.R. Ryan, Q. Liu, P. Sperling, B. Dong, S. Franke, and E. Delhaize. A Higher Plant Delta-8 Sphingolipid Desaturase with a Preference for (Z)-isomer Formation Confers Aluminum Tolerance to Yeast and Plants. Plant Physiol. 144: 1968-1977 (2007).
17. H. Jr. Merrill, M.C. Sullards, J.C. Allegood, S. Kelly, and E. Wang. Sphingolipidomics: High-throughput, Structure-specific, and Quantitative Analysis of Sphingolipids by LC-MS-MS. Methods 36: 207-224 (2005).
18. M.C. Sullards, J.C. Allegood, S. Kelly, E. Wang, C.A. Haynes, H. Park, Y. Chen, Y, and A.H. Jr Merrill. Structure-specific, Quantitative Methods for Analysis of Sphingolipids by Liquid Chromatography-Tandem Mass Spectrometry: "Inside- out" Sphingolipidomics. Methods Enzym. 432: 83-115 (2007).
19. L.A. Cowart and Y.A. Hannun. Using Genomic and Lipiomic Strategies to Investigate Sphingolipid Function in the Yeast Heat-Stress Response. Biochem. Soc. Transactions 33: 1166-1169 (2005).
20. Y. Chen, J. Allegood, Y. Liu, E. Wang, B. Cachón-Gonzalez, T.M. Cox, A.H. Jr Merrill, and M.C. Sullards. Imaging MALDI Mass Spectrometry Using an Oscillating Capillary Nebulizer Matrix Coating System and its Application to Analysis of Lipids in Brain from a Mouse Model of Tay-Sachs/Sandhoff Disease. Anal. Chem. 80: 2780-2788 (2008).
21. P. Sperling, and E. Heinz. Plant Sphingolipids: Structural Diversity, Biosynthesis, First Genes and Functions. Biochimica et Biophysica Acta 1632: 1-15 (2003).
22. J.E. Markham, J. Li, E.B. Cahoon, and J.G. Jaworski. Plant Sphingolipids: Separation and Identification of Major sphingolipid classes from leaves. J. Biol. Chem. 281: 22,684-22,694 (2006).
23. R.L. Lester and R.C. Dickson. High-Performance Liquid Chromatography Analysis of Molecular Species of Sphingolipid-Related Long Chain Bases and Long Chain Base Phosphates in Saccharomyces cerevisiae after Derivatization with 6-Aminoquinolyl-N-hydroxysuccinimidyl Carbamate. Anal. Biochem. 298: 283-292 (2001).
24. P. Sperling, A. Blume, U. Zähringer, and E. Heinz. Further Characterization of Δ8- Sphingolipid Desaturases from Higher Plants. Biochem. Soc. Transactions 28: 638-641 (2000).
25. C. Beckmann, J. Rattke, N.J. Oldhan, P. Sperling, E. Heinz, and W. Boland. Characterization of a Δ8-Sphingolipid Desaturase From Higher Plants: A Stereochemical and Mechanistic Study on the Origin of E,Z Isomers. Angew. Chem. Int. Ed. 41: 2298-2300 (2002).
26. P. Sperling, B. Libisch, U. Zähringer, J.A. Napier, and E. Heinz. Functional Identification of a Δ8-sphingolipid Desaturase from Borago officinalis. Arch. Biochem. Biophys. 388: 293-298 (2001).
27. P. Ternes, S. Franke, U. Zähringer, P. Sperling, and E. Heinz. Identification and Characterization of a Sphingolipid Δ4-Desaturase Family. J. Bio. Chem. 277: 25,512-25,518 (2002).
28. P. Sperling, U. Zähringer, and E. Heinz. A Sphingolipid Desaturase from Higher Plants. J. Bio. Chem. 273: 28,590-28,596 (1998).
29. V. Sayanova, F. Beaudoin, L.V. Michaelson, P.R. Shewry, and J. Napier. Identification of Primula Fatty Acid Delta 6-desaturases with n-3 Substrate Preferences. FEBS Lett. 542: 100-104 (2003).
30. F. García-Maroto, J.A. Garrido-Cárdenas, J. Rodríguez-Ruiz, M. Vilches-Ferrón, A.C. Adam, J. Polaina, and D.L. Alonso. Cloning and Molecular Characterization of the Δ6-desaturase from two Echium plant species: production of GLA by heterologous expression in yeast and tobacco. Lipids 37: 417-426 (2002).
31. H. Ochman, M.M. Medhora, D. Garza, and D.L. Hartl. Amplification of Flanking Sequences by Inverse PCR. In M.A. Innis, D.H. Geldfand, J. J. Sninsky, T.J. White, PCR Protocols: A Guide to Methods and Applications, Academic Press, San Diego, 1990, pp. 219-227.
32. J. Sambrook, and D. Russell. Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York, 2001.
33. O. Sayanova, M.A. Smith, P. Lapinskas, A. K. Stobart, G. Dobson, W.W. Christie, P.R. Shewry, and J. A. Napier. Expression of a Borage Desaturase Cdna Containing an N-terminal Cytochrome b5 Domain Results in the Accumulation of High Levels of Δ6-desaturated Fatty Acids in Transgenic Tobacco. Proc. Natl. Acad. Sci. USA 94: 4211-4216 (1997).
34. J. Shanklin, E. Whittle, and B.G. Fox. Eight Histidine Residues Are Catalytically Essential in a Membrane-associated Iron Enzyme, Stearoyl-CoA Desaturase, and Are Conserved in Alkane Hydroxylase and Xylene Monooxygenase. Biochem. 33: 12787-12794 (1994).
35. W. Griffiths, A. Jonsson, S. Liu, D. Rai, and Y. Wang. Electrospray and Tandem Mass Spectrometry in Biochemistry. Biochem. Soc. 355: 545-561 (2001).
36. B. Lieser, G. Liebisch, W. Drobnik, and G. Schmitz. Quantification of phingosine and Sphingasine from Crude Lipid Extracts by HPLC Electrospray onization Tandem Mass Spectrometry. J. Lipid Res. 44: 2209-2216 (2003).
37. J.E. Markham and J.G. Jaworski. Rapid Measurement of Sphingolipids from Arabidopsis thaliana by Reversed-phase High-performance Liquid Chromatography Coupled to Electrospray Ionization Tandem Mass Spectrometry. Rapid Comm. Mass Spec. 21: 1304-1314 (2006).
38. F. Hsu, J. Turk, M. Stewart, and D. Downing. Structural Studies on Ceramides as Lithiated Adducts by Low Energy Collisional-Activated Dissociation Tandem Mass Spectrometry with Electrospray Ionization. Am. Soc. Mass Spec. 13: 680-695 (2002).
39. M. Gu, J. Kerwin, J. Watts, and R. Aebersold. Ceramide Profiling of Complex Lipid Mixtures by Electrospray Ionization Mass Spectrometry. Anal. Biochem. 244: 347-356 (1997).
40. N. Mano, Y. Oda, K. Yamad, N. Asakawa, and K. Katayama. Simultaneous Quantitative Determination Method for Sphingolipid Metabolites by Liquid Chromatography/Ionspray Ionization Tandem Mass Spectrometry. Anal. Biochem. 244: 291-300 (1997).
41. E. Berdyshev, I. Gorshkova, J. Garcia, V. Natarajan, and W. Hubbard. Quantitative Analysis of Sphingoid Base-1-Phosphates as Bisacetylated Derivatives by Liquid Chromatography-Tandem Mass Spectrometry. Anal. Biochem. 339: 129-136 (2005).
42. W. Seefelder, G. Schwerdt, R. Freudinger, M. Gekle, and H.-U. Humpf. Liquid Chromatography/Electrospray Ionization-Mass Spectrometry Method for the Quantification of Sphingosine and Sphinganine in cell cultures exposed to Fumonisins. J. Chromatogr. B 780: 137-144 (2002).
43. P. Ferraboschi, R. Canevotti, P. Grisenti, and E. Santaniello. A New Flexible Synthesis of (R,S)-Mevalonolactone. J. Chem. Soc. Perkin Trans. 2301-2303 (1987).
44. F. Destaillats and P. Angers. One-Step Methodology for the Synthesis of FA Picolinyl Esters from Intact Lipids. J. Am. Oil Chem. Soc. 79: 253-256 (2002).
45. W.W. Christie, E.Y. Brechany, and R.T. Holman. Mass Spectra of the Picolinyl Esters of Isomeric Mono- and Dienoic Fatty Acids. Lipids 22: 224-228 (1987).