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

Volumn 20, Issue 6, 2009, Pages 1037-1047

  Pittenauer, Ernst ^a   Allmaier, Günter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ADDUCT IONS; ALKYL CHAINS; CASTOR BEANS; CATIONIZED; CHARGE-REMOTE FRAGMENTATIONS; COCOA BUTTERS; DOUBLE BONDS; END PRODUCTS; FATTY ACID COMPOSITIONS; GATING WINDOWS; HIGH ENERGIES; HYDROXY GROUPS; ION SPECTRUM; MASS ACCURACIES; OLIVE OIL; PLANT OIL; PRECURSOR IONS; PRODUCT IONS; SODIUM CARBOXYLATES; STRUCTURAL ELUCIDATIONS; TRIACYLGLYCEROL; TRIACYLGLYCEROLS;

ACIDS; BEVERAGES; CARBOXYLATION; FATTY ACIDS; GLYCEROL; MASS SPECTROMETRY; VEGETABLE OILS;

IONS;

ALKALI; CARBOXYLIC ACID; FATTY ACID; HYDROXYL GROUP; ION; LITHIUM; POTASSIUM; SODIUM; TRIACYLGLYCEROL; VEGETABLE OIL;

ACCURACY; ARTICLE; CACAO; COLLISIONALLY ACTIVATED DISSOCIATION; FATTY ACID ANALYSIS; FRAGMENTATION REACTION; LIPID ANALYSIS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; STRUCTURE ANALYSIS; TIME OF FLIGHT MASS SPECTROMETRY;

RICINUS COMMUNIS; THEOBROMA CACAO;

EID: 65549128165     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2009.01.009     Document Type: Article

References (46)

1. Byrdwell W.C., and Emken E.A. Analysis of triglycerides using atmospheric pressure chemical ionization mass spectrometry. Lipids 30 (1995) 173-175
2. Neff W.E., and Byrdwell W.C. Soybean oil triacylglycerol analysis by reversed-phase high-performance liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry. J. Am. Oil Chem. Soc. 72 (1995) 1185-1191
3. Neff W.E., and Byrdwell W.C. Triacylglycerol analysis by high performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry: Crepis alpina and Vernonia galamensis seed oils. J. Liquid Chromatogr. 18 (1995) 4165-4181
4. Byrdwell W.C., and Neff W.E. Analysis of genetically modified canola varieties by atmospheric pressure chemical ionization mass spectrometry and flame ionization detection. J. Liquid Chromatogr. Rel. Technol. 19 (1996) 2203-2225
5. Laakso P., and Voutilainen P. Analysis of triacylglycerols by silver-ion high-performance liquid chromatography-atmospheric pressure chemical ionization. Lipids 31 (1996) 1311-1322
6. Mottram H.R., and Evershed R.P. Structure analysis of triacylglycerol positional isomers using atmospheric pressure chemical ionization mass spectrometry. Tetrahedron Lett. 37 (1996) 8593-8596
7. Byrdwell W.C., Emken E.A., Neff W.E., and Adlof R.O. Quantitative analysis of triglycerides using atmospheric pressure chemical ionization-mass spectrometry. Lipids 31 (1996) 919-935
8. Byrdwell W.C. Atmospheric pressure chemical ionization mass spectrometry for the analysis of lipids. Lipids 36 (2001) 327-346
9. Byrdwell W.C., and Neff W.E. Dual parallel electrospray ionization and atmospheric pressure chemical ionization mass spectrometry (MS), MS/MS and MS/MS/MS for the analysis of triacylglycerols and triacylglycerol oxidation products. Rapid Commun. Mass Spectrom. 16 (2002) 300-319
10. Xu Y., and Brenna J.T. Atmospheric pressure covalent adduct chemical ionization tandem mass spectrometry for double bond location in monoene- and diene-containing triacylglycerols. Anal. Chem. 79 (2007) 2525-2536
11. Duffin K.L., Henion J.D., and Shieh J.J. Electrospray and tandem mass spectrometric characterization of acylglycerol mixtures that are dissolved in nonpolar solvents. Anal. Chem. 63 (1991) 1781-1788
12. Cheng C., Pittenauer E., and Gross M.L. Charge-remote fragmentations are energy-dependent processes. J. Am. Soc. Mass Spectrom. 9 (1998) 840
13. Cheng C., Gross M.L., and Pittenauer E. Complete structural elucidation of triacylglycerols by tandem sector mass spectrometry. Anal. Chem. 70 (1998) 4417-4426
14. Hsu F.-F., and Turk J. Structural characterization of triacylglycerols as lithiated adducts by electrospray ionization mass spectrometry using low-energy collisionally activated dissociation on a triple quadrupole instrument. J. Am. Soc. Mass Spectrom. 10 (1999) 587-599
15. n ion-trap MS. J. Am. Oil Chem. Soc. 80 (2003) 195-202
16. Wu Z., Rodgers R.P., and Marshall A.G. Characterization of vegetable oils: Compositional fingerprints derived from electrospray ionization Fourier-transform ion cyclotron resonance mass spectrometry. J. Agric. Food Chem. 52 (2004) 5322-5328
17. Pittenauer E., and Welz W. Free Fatty Acids and Triacylglycerols. In: Gross M.L., and Caprioli R.M. (Eds). The Encyclopedia of Mass Spectrometry, Vol. III, Biological Applications Part A: Carbohydrates, Nucleic Acids, and other Biological Compounds (2005), Elsevier, Oxford, UK 397-415
18. Lin J.-T., and Arcinas A. Regiospecific analysis of diricinoleoylglycerols in castor (Ricinus communis L.) oil by electrospray ionization-mass spectrometry. J. Agric. Food Chem. 55 (2007) 2209-2216
19. McAnoy A.M., Wu C.C., and Murphy R.C. Direct qualitative analysis of triacylglycerols by electrospray mass spectrometry using a linear ion trap. J. Am. Soc. Mass Spectrom. 16 (2005) 1498-1509
20. Murphy R.C., James P.F., McAnoy A.M., Krank J., Duchoslav E., and Barkley R.M. Detection of the abundance of diacylglycerol and triacylglycerol molecular species in cells using neutral loss mass spectrometry. Anal. Biochem. 366 (2007) 59-70
21. Barber M., Tetler L.W., Bell D., Ashcroft A.E., Brown R.S., and Moore C. Applications of a continuous flow probe in FAB mass spectrometry. Org. Mass Spectrom. 22 (1987) 647-650
22. Evans C., Traldi, Bambagiotti-Alberti M., Gianellini V., Coran S.A., and Vincieri F.F. Positive and negative fast atom bombardment mass spectrometry and collision spectroscopy in structural characterization of mono-, di-, and triglycerides. Biol. Mass Spectrom. 20 (1991) 351-356
23. Hori M., Sahashi Y., Koike S., Yamaoka R., and Sato M. Molecular species analysis of polyunsaturated fish triacylglycerol by high performance liquid chromatography/fast atom bombardment mass spectrometry. Anal. Sci. 10 (1994) 719-724
24. Lamberto M., and Saitta M. Principal component analysis in fast atom bombardment-mass spectrometry in edible oils. J. Am. Oil. Chem. Soc. 72 (1995) 867-871
25. Kim Y.H., Han S.-Y., Cho S.-H., Yoo J.S., and Jhon G.-J. Structural determination of synthetic monoacetyldiglycerides by tandem mass spectrometry of sodium-adducted molecules. Rapid Commun. Mass Spectrom. 13 (1999) 481-487
26. Kim H.K., So K.-Y., Limb J.-K., Jhon G.-J., and Han S.-Y. Identification of short-chain fatty acids at sn-2 and sn-3-positions from bovine udder by fast atom bombardment mass spectrometry. Rapid Commun. Mass Spectrom. 14 (2000) 2230-2237
27. Pittenauer E., Allmaier G., and Schmid E.R. Rapid molecular mass determination of mon-, di-, and triglycerides by californium-252 plasma desorption mass spectrometry using 3-(3-pyridyl)acrylic acid as matrix. Org. Mass Spectrom. 29 (1994) 108-111
28. Zöllner P., Stübiger G., Schmid E., Pittenauer R., and Allmaier G. MALDI mass spectrometry of biomolecules and synthetic polymers using alkali hexacyanoferrate (II) complexes and glycerol as matrix. Int. J. Mass Spectrom. Ion Processes 169/170 (1997) 99-107
29. Asbury G.R., Al-Saad K., Siems W.F., Hannan R.M., and Hill Jr. H.H. Analysis of triacylglycerols and whole oils by matrix-assisted laser desorption/time of flight mass spectrometry. J. Am. Soc. Mass Spectrom. 10 (1999) 983-991
30. Ayorinde F.O., Elhilo E., and Hlongwane C. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of canola, castor, and olive oil. Rapid Commun. Mass Spectrom. 13 (1999) 737-739
31. Ayorinde F.O., Eribo B.E., Balan K.V., Johnson Jr. J.H., and Wan L.W. Determination of major triacylglycerol components of polyunsaturated specialty oils using matrix-assisted laser desorption time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 13 (1999) 937-942
32. Ayorinde F.O., Keith Jr. Q.L., and Wan L.W. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of cod liver oil and the effect analyte/matrix concentration on signal intensities. Rapid Commun. Mass Spectrom. 13 (1999) 1762-1769
33. Ayorinde F.O., Elhilo E., Hlongwane C., and Saeed K. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of Vernonia galamensis oil. J. Am. Oil. Chem. Soc. 76 (1999) 1217-1221
34. Stübiger G., Pittenauer E., and Allmaier G. Characterization of castor oil by on-line and off-line non-aqueous high-performance liquid chromatography-mass spectrometry (APCI and UV/MALDI). Phytochem. Anal. 14 (2003) 337-346
35. Al-Saad K.A., Zabrouskov V., Siems W.F., Knowles N.R., Hannan R.M., and Hill Jr. H.H. Matrix-assisted laser desorption time-of-flight mass spectrometry of lipids: Ionization and prompt fragmentation. Rapid Commun. Mass Spectrom. 17 (2003) 87-96
36. Lay Jr. J.O., Liyanage R., Durham B., and Brooks J. Rapid characterization of edible oils by direct matrix-assisted laser desorption time-of-flight mass spectrometry analysis of triacylglycerols. Rapid Commun. Mass Spectrom. 20 (2006) 952-958
37. Stübiger G., and Belgacem O. Analysis of Lipids using 2,4,6-trihydroxyacetophenone as a matrix for MALDI mass spectrometry. Anal. Chem. 79 (2007) 3206-3213
38. Kaufmann M., and Wiesman Z. Pomegranate oil analysis with emphasis on MALDI-TOF/MS triacylglycerol fingerprinting. J. Agric. Food Chem. 55 (2007) 10405-10413
39. Pittenauer E., and Allmaier G. High-energy collision-induced dissociation of biomolecules by means of MALDI-TOF/RTOF mass spectrometry in comparison to tandem sector mass spectrometry. Comb. Chem. High Throughput Screen. 12 (2009) 137-155
40. Belgacem O., Bowdler A., Brookhouse I., Brancia F.L., and Raptakis E. Dissociation of biomolecules using a ultraviolet matrix-assisted laser desorption/ionization time-of-flight/curved field reflectron tandem mass spectrometer equipped with a differential-pumped collision cell. Rapid Commun. Mass Spectrom. 20 (2006) 1653-1660
41. Tomer K.B., Crow F.W., and Gross M.L. Location of double-bond position in unsaturated fatty acids by negative ion MS/MS. J. Am. Chem. Soc. 105 (1983) 5487-5488
42. Claeys M., Nizigiyimana L., Van den Heuvel H., and Derrick P.J. Mechanistic aspects of charge-remote fragmentation in saturated and mono-unsaturated fatty acid derivatives. Rapid Commun. Mass Spectrom. 10 (1996) 770-774
43. Huysmans L., Nizigiyimana L., Van den Heuvel H., and Claeys M. Charge-remote molecular hydrogen removal in protonated and alkali-cationized long-chain fatty acid esters upon cesium ion bombardment. Int. J. Mass Spectrom. 188 (1999) 39-52
44. Trimpin S., Clemmer D.E., and McEwen C.N. Charge-remote fragmentation of lithiated fatty acids on a TOF-TOF using matrix-ionization. J. Am. Soc. Mass Spectrom. 18 (2007) 1967-1972
45. Cheng C., and Gross M.L. Applications and mechanisms of charge-remote fragmentation. Mass Spectrom. Rev. 19 (2000) 398-420
46. Gross M.L. Charge-remote fragmentation: An account of research on mechanisms and applications. Int. J. Mass Spectrom. 200 (2000) 611-624