Structural determination of glucosylceramides isolated from marine sponge by fast atom bombardment collision-induced dissociation linked scan at constant B/E

Journal of Mass Spectrometry

Volumn 44, Issue 12, 2009, Pages 1698-1708

  Ahn, Young Min ^a   Lee, Won Woong ^a   Jung, Jee H ^b   Lee, Sang Gi ^c   Honga, Jongki ^a  

^a Kyung Hee University   (South Korea)

^b Pusan National University   (South Korea)

^c Ewha Womans University   (South Korea)

Author keywords

Collision induced dissociation; Fast atom bombardment; Glucosylceramides; Haliclona (Reniera) sp.; Marine sponge

Indexed keywords

ACCURATE MASS; ACYL CHAIN; CHARGE-REMOTE FRAGMENTATION; COLLISION-INDUCED DISSOCIATION; ELEMENTAL COMPOSITIONS; FAB-MASS; FAST ATOM BOMBARDMENT; FATTY ACID METHYL ESTER; MARINE SPONGE; METHANOLYSIS; PRECURSOR IONS; PROTONATED MOLECULES; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURAL DETERMINATION; SUGAR RINGS;

ATOMS; CHROMATOGRAPHIC ANALYSIS; DISSOCIATION; ESTERS; FATTY ACIDS; HIGH PRESSURE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONVOLATILE STORAGE; SUGAR (SUCROSE); SUGARS;

IONS;

BETA DEXTRO GLUCOSYLSPHINGANINE; FATTY ACID ESTER; GLUCOSYLCERAMIDE; HYDROGEN; ION; METHANOL DERIVATIVE; SODIUM; SPHINGANINE; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; DISSOCIATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; FRAGMENTATION REACTION; HALICLONA; KOREA; LIPID ANALYSIS; METHANOLYSIS; MOLECULE; NONHUMAN; PRECURSOR; PRIORITY JOURNAL; PROTON TRANSPORT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEASHORE;

ACETYLATION; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSYLCERAMIDES; HALICLONA; METHANOL; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

HALICLONA SP.; SPHINGOIDEA;

EID: 72449153818     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1678     Document Type: Article

References (38)

1. D. V. Lynch, T. M. Dunn. An introduction to plant sphingolipids and a review of recent advances in understanding theirmetabolism and function. New Phytologist 2004, 161, 677.
2. A. H. Futerman, Y. A. Hannun. The complex life of simple sphingolipids. European Molecular Biology Organization Reports 2004, 5, 777.
3. A. H. Futerman. Intracellular trafficking of sphingolipids: relationship to biosynthesis. Biochimica et Biophysica Acta 2006, 1758, 1885.
4. D. A. Brown, E. London. Structure and function of sphingolipid- and cholesterol-rich membrane rafts. The Journal of Biological Chemistry 2000, 275, 17221.
5. A. H. Merrill Jr, M. C. Sullards, E. Wang, K. A. Voss, R. T. Riley. Sphingolipid metabolism: roles in signal transduction and disruption by fumonisins. Environmental Health Perspectives 2001, 109, 283.
6. D. Warnecke, E. Heinz. Recently discovered functions of glucosylceramides in plants and fungi. Cellular and Molecular Life Sciences 2003, 60, 919.
7. S. Spiegel, S. Milstien. Sphingosine-1-phosphate: an enigmatic signalling lipid. Nature Reviews Molecular Cell Biology 2003, 4, 397.
8. W. J. van Blitterswijk, A. H. van der Luit, R. J. Veldman, M. Verheij, J. Borst. Ceramide: second messenger or modulator of membrane structure and dynamics. Biochemical Journal 2003, 369, 199.
9. D. K. Perry, Y. A. Hannun. The role of ceramide in cell signaling. Biochimica et Biophysica Acta 1998, 1436, 233.
10. M. R. Pinto, M. L. Rodrigues, L. R. Travassos, R. M. T. Haido, R. Wait, E. Barreto-Bergter. Characterization of glucosylceramides in Pseudallescheria boydii and their involvement in fungal differentiation. Glycobiology 2002, 12, 251.
11. K. Yamada, K. Sasaki, Y. Harada, R. Isobe, R. Higuchi. Constituents of Holothuroidea, Isolation and structure of glucocerebrosides from the sea cucumber Holothuria pervicax. Chemical and Pharmaceutical Bulletin 2002, 50, 1467.
12. J. Holgersson, W. Pimlott, B. E. Samuelsson. Electronionization mass spectrometry for sequence analysis of glycosphingolipid mixtures by fractional evaporation in the ion source. Rapid Communications in Mass Spectrometry 1989, 3, 400.
13. J. Holgersson, J. M. Curtis, M. R. Morris, L. W. Tetler, P. J. Derrick, B. E. Samuelsson. Electron ionization-tandem mass spectrometry of glycosphingolipids. Part II. The identification of a carbohydrate sequence corresponding to a novel repetitive blood group A heptaglycosylceramide. Rapid Communications in Mass Spectrometry 1993, 7, 421.
14. T. Ariga, T. Murata, M. Oshima, M. Maezawa, T. Miyatake. Characterization of glycosphingolipids by direct inlet chemical ionization mass spectrometry. Journal of Lipid Research 1980, 21, 879.
15. X. Han, R. W. Gross. Shotgun lipidomics: electrospray ionization mass spectrometric analysis and quantitation of cellular lipidomes directly from crude extracts of biological samples. Mass Spectrometry Reviews 2005, 24, 367.
16. N. Bartke, A. Fischbeck, H. U. Humpf. Analysis of sphingolipids in potatoes (Solanum tuberosum L.) and sweet potatoes (Ipomoea batatas (L.) Lam.) by reversed phase high-performance liquid chromatography electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS). Molecular Nutrition and Food Research 2006, 50, 1201.
17. B. J. Pettus, A. Bielawska, B. J. Kroesen, P. D. R. Moeller, Z. M. Szulc, Y. A. Hannun, M. Busman. Observation of different ceramide species from crude cellular extracts by normal-phase high-performance liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry. Rapid Communications in Mass Spectrometry 2003, 17, 1203.
18. F. M. Rubino, L. Zecca, S. Sonnino. Characterization of a complex mixture of ceramides by fast atom bombardment and precursor and fragment analysis tandem mass spectrometry. Biological Mass Spectrometry 1994, 23, 82.
19. Q. Ann, J. Adams. Structure-specific collision-induced fragmentations of ceramides cationized with alkali-metal ions. Analytical Chemistry 1993, 65, 7.
20. M. C. Sullards, D. V. Lynch, A. H. Merrill Jr, J. Adams. Structure determination of soybean and wheat glucosylceramides by tandem mass spectrometry. Journal ofMass Spectrometry 2000, 35, 347.
21. P. B. O'Connor, C. E. Costello. A high pressure matrix-assisted laser desorption/ionization Fourier transform mass spectrometry ion source for thermal stabilization of labile biomolecules. Rapid Communications in Mass Spectrometry 2001, 15, 1862.
22. D. J. Harvey. Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates. Mass Spectrometry Reviews 1999, 18, 349.
23. F. F. Hsu, J. Turk. Structural determination of glycosphingolipids as lithiated adducts by electrospray ionization mass spectrometry using low-energy collisional-activated dissociation on a triple stage quadrupole instrument. Journal of the American Society for Mass Spectrometry 2001, 12, 61.
24. K. Mills, S. Eaton, V. Ledger, E. Young, B. Winchester. The synthesis of internal standards for the quantitative determination of sphingolipids by tandem mass spectrometry. Rapid Communications inMass Spectrometry 2005, 19, 1739.
25. X. Han. Characterization and direct quantitation of ceramide molecular species from lipid extracts of biological samples by electrospray ionization tandem mass spectrometry. Analytical Biochemistry 2002, 302, 199.
26. E. Pittenauer, G. Allmaier. The renaissance of high-energy CID for structural elucidation of complex lipids: MALDI-TOF/RTOF-MS of alkali cationized triacylglycerols. Journal of the American Society for Mass Spectrometry 2009, 20, 1037.
27. M. M. Cordero, C. Wesdemiotis. Characterization of the neutral products formed upon charge-remote fragmentation of fatty acid ions. Analytical Chemistry 1994, 66, 861.
28. N. J. Jensen, K. B. Tomer, M. L. Gross. Gas-phase in decompositions occurring remote to a charge site. Journal of the American Chemical Society 1985, 107, 1863.
29. C. Cheng, E. Pittenauer, M. L. Gross. Charge-remote fragmentations are energy-dependent processes. Journal of the American Society for Mass Spectrometry 1998, 9, 840.
30. J. Hong, K. Cho, Y. H. Kim, C. Cheong, K. S. Lee, J. H. Jung. Structural determination of lysophosphatidylcholines extracted from marine sponges by fast atom bombardment tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2001, 15, 1120.
31. T. Park, T. A. Mansoor, P. B. Shinde, B. Bao, J. Hong, J. H. Jung. New cerebrosides from amarine sponge Haliclona (Reniera) sp. Chemical and Pharmaceutical Bulletin 2009, 57, 106.
32. C. Cheng, M. L. Gross. Applications and mechanisms of chargeremote fragmentation. Mass Spectrometry Reviews 2000, 19, 398.
33. V. H. Wysocki, M. M. Ross, S. R. Horning, R. G. Cooks. Remote-site (charge-remote) fragmentation. Rapid Communications in Mass Spectrometry 1988, 2, 214.
34. D. J. Harvey. A new charge-associated mechanism to account for the production of fragment ions in the high-energy CID spectra of fatty acids. Journal of the American Society for Mass Spectrometry 2005, 16, 280.
35. J. Hong, Y. H. Kim, J. H. Gil, K. Cho, J. H. Jung, S. Y. Han. Structural determination of hexadecanoic lysophosphatidylcholine regioisomers by fast atom bombardment tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2002, 16, 2089.
36. J. H. Gil, J. J. Seo, K. J. Kim, J. H. Jung, O. S. Jung, M. S. Kim, J. Hong. Structural determination of cyclitol derivatives by fast-atom bombardment tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2006, 20, 1253.
37. J. H. Gil, J. Y. Hong, J. H. Jung, K. J. Kim, J. Hong. Structural determination ofmonoacylglycerols extracted frommarine sponge by fast atom bombardment tandem mass spectrometry. Rapid Communications inMass Spectrometry 2007, 21, 1264.
38. N. J. Jensen, M. L. Gross. Fast atom bombardment and tandem mass spectrometry for determining iso- and anteiso-fatty acids. Lipids 1986, 21, 362.