Shotgun lipidomics: Electrospray ionization mass spectrometric analysis and quantitation of cellular lipidomes directly from crude extracts of biological samples

Mass Spectrometry Reviews

Volumn 24, Issue 3, 2005, Pages 367-412

  Han, Xianlin ^a   Gross, Richard W ^a,b  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

Alzheimers disease; Diabetes; Electrospray ionization mass spectrometry; Lipidome; Lipidomics

Indexed keywords

ALZHEIMERS DISEASE; DIABETES; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; LIPIDOME; LIPIDOMICS;

BIOLOGICAL MEMBRANES; CATALYSIS; CELLS; DISEASES; FATTY ACIDS; IONIZATION; LIPIDS; PHYSIOLOGY; PROTEINS;

MASS SPECTROMETRY;

CELL EXTRACT; LIPID;

ANIMAL; BIOLOGY; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; INSTRUMENTATION; METHODOLOGY; REVIEW;

ANIMALS; BIOLOGY; CELL EXTRACTS; HUMANS; LIPIDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 18344393519     PISSN: 02777037     EISSN: None     Source Type: Journal    
DOI: 10.1002/mas.20023     Document Type: Article

References (199)

1. Acharya U, Patel S, Koundakjian E, Nagashima K, Man X, Acharya JK. 2003. Modulating sphingolipid biosynthetic pathway rescues photoreceptor degeneration. Science 299:1740-1743.
2. Alessenko AV, Burlakova EB. 2002. Functional role of phospholipids in the nuclear events. Bioelectrochemistry 58:13-21.
3. 2gamma). Roles in the membrane remodeling and activation induced by oxidative stress. J Biol Chem 278:8809-8814.
4. Ashcroft SJH. 1997. Intracellular second messengers. Adv Exp Med Biol 426:73-80.
5. Athenstaedt K, Daum G. 1999. Phosphatidic acid, a key intermediate in lipid metabolism. Eu J Biochem 266:1-16.
6. Baker DL, Umstot ES, Desiderio DM, Tigyi GJ. 2000. Quantitative analysis of lysophosphatidic acid in human blood fractions. Ann NY Acad Sci 905:267-269.
7. Baker DL, Desiderio DM, Miller DD, Tolley B, Tigyi GJ. 2001. Direct quantitative analysis of lysophosphatidic acid molecular species by stable isotope dilution electrospray ionization liquid chromatography-mass spectrometry. Anal Biochem 292:287-295.
8. Beckedorf AI, Schaffer C, Messner P, Peter-Katalinic J. 2002. Mapping and sequencing of cardiolipins from Geobacillus stearothermophilus NRS 2004/3a by positive and negative ion nanoESI-QTOF-MS and MS/MS. J Mass Spectrom 37:1086-1094.
9. Berry KAZ, Borgeat P, Gosselin J, Flamand L, Murphy RC. 2003. Urinary metabolites of leukotriene B4 in the human subject. J Biol Chem 278: 24449-24460.
10. Bligh EG, Dyer WJ. 1959. A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37:911-917.
11. Blom TS, Koivusalo M, Kuismanen E, Kostiainen R, Somerharju P, Ikonen E. 2001. Mass spectrometric analysis reveals an increase in plasma membrane polyunsaturated phospholipid species upon cellular cholesterol loading. Biochemistry 40:14635-14644.
12. Bocckino SB, Exton JH. 1996. Phosphatidic acid. Handbook Lipid Res 8:75-123.
13. Borrett VT, Duncan A, Mathews RJ, Traeger JC. 1998. Electrospray mass spectrometry of phospholipids extracted from inactivated bacteria. Adv Mass Spectrom 14:C056070/1-C056070/13.
14. Brachwitz H, Thomas Y, Bergmann J, Langen P, Berdel WE. 1997. New nucleoside-5′-alkylphosphonophosphates and related compounds containing 2′-deoxycytidine, thymidine and adenosine as nucleoside component. Syntheses and their effects on tumor cell growth in vitro. Chem Phys Lipids 87:31-39.
15. Brügger B, Erben G, Sandhoff R, Wieland FT, Lehmann WD. 1997. Quantitative analysis of biological membrane lipids at the low picomole level by nano-electrospray ionization tandem mass spectrometry. Proc Natl Acad Sci USA 94:2339-2344.
16. Brügger B, Sandhoff R, Wegehingel S, Gorgas K, Malsam J, Helms JB, Lehmann W-D, Nickel W, Wieland FT. 2000. Evidence for segregation of sphingomyelin and cholesterol during formation of COPI-coated vesicles. J Cell Biol 151:507-517.
17. Byrdwell WC. 1998. Dual parallel mass spectrometers for analysis of sphingolipid, glycerophospholipid and plasmalogen molecular species. Rapid Commun Mass Spectrom 12:256-272.
18. Byrdwell WC. 2003. Dual parallel liquid chromatography/dual mass spectrometry (LC2/MS2) of bovine brain total lipid extract. J Liq Chromatogr R T 26:3147-3181.
19. Byrdwell WC, Borchman D. 1997. Liquid chromatography/mass-spectrometric characterization of sphingomyelin and dihydrosphingomyelin of human lens membranes. Ophthalmic Res 29:191-206.
20. Byrdwell WC, Neff WE. 2002. 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: 300-319.
21. Chen S. 1997. Tandem mass spectrometric approach for determining structure of molecular species of aminophospholipids. Lipids 32:85-100.
22. Cheng C, Gross ML, Pittenauer E. 1998. Complete structural elucidation of triacylglycerols by tandem sector mass spectrometry. Anal Chem 70:4417-4426.
23. Cheng H, Xu J, Mckeel DW Jr, Han X. 2003. Specificity and potential mechanism of sulfatide deficiency in Alzheimers disease: An electrospray ionization mass spectrometric study. Cell Mol Biol 49:809-818.
24. Cohen JS, Brown HA. 2001. Phospholipases stimulate secretion in RBL mast cells. Biochemistry 40:6589-6597.
25. Cole RB. 1997. Electrospray ionization mass spectrometry. New York: Wiley.
26. Cole MJ, Enke CG. 1991. Direct determination of phospholipid structures in microorganisms by fast atom bombardment triple quadrupole mass spectrometry. Anal Chem 63:1032-1038.
27. Creer MH, Gross RW. 1985. Reversed-phase high-performance liquid chromatographic separation of molecular species of alky] ether, vinyl ether, and monoacyl lysophospholipids. J Chromatogr 338:61-69.
28. Cullis PR, Fenske DB, Hope MJ. 1996. Physical properties and functional roles of lipids in membranes. In: Vance DE, Vance J, editors. Biochemistry of lipids, lipoproteins and membranes. Amsterdam, The Netherlands: Elsevier. pp 1-33.
29. Cutler RG, Pedersen WA, Camandola S, Rothstein JD, Mattson MP. 2002. Evidence that accumulation of ceramides and cholesterol esters mediates oxidative stress-induced death of motor neurons in amyotrophic lateral sclerosis. Ann Neurol 52:448-457.
30. de la Mora JF, van Berkel GJ, Enke CG, Cole RB, Martinez-Sanchez M, Fenn JB. 2000. Electrochemical processes in electrospray ionization mass spectrometry. J Mass Spectrom 35:939-952.
31. DeLong CJ, Baker PRS, Samuel M, Cui Z, Thomas MJ. 2001. Molecular species composition of rat liver phospholipids by ESI-MS/MS: The effect of chromatography. J Lipid Res 42:1959-1968.
32. Desai K, Sullards MC, Allegood J, Wang E, Schmelz EM, Hartl M, Humpf H-U, Liotta DC, Peng Q, Merrill AH Jr. 2002. Fumonisins and fumonisin analogs as inhibitors of ceramide synthase and inducers of apoptosis. Biochim Biophys Acta 1585:188-192.
33. Marzo V. 1995. Review: Arachidonic acid and eicosanoids as targets and effectors in second messenger interactions. Prostag Leukotr Ess 53: 239-254.
34. Dombrowsky H, Clark GT, Rau GA, Bernhard W, Postle AD. 2003. Molecular species compositions of lung and pancreas phospholipids in the cftr(tm1HGU/tm1HGU) cystic fibrosis mouse. Pediatr Res 53:447-454.
35. Drobnik W, Liebisch G, Audebert F-X, Frohlich D, Gluck T, Vogel P, Rothe G, Schmitz G. 2003. Plasma ceramide and lysophosphatidylcholine inversely correlate with mortality in sepsis patients. J Lipid Res 44: 754-761.
36. Duffin KL, Henion JD, Shieh JJ. 1991. Electrospray and tandem mass spectrometric characterization of acylglycerol mixtures that are dissolved in nonpolar solvents. Anal Chem 63:1781-1788.
37. Duffin KL, Obukowicz MG, Raz A, Shieh JJ. 2000. Electrospray/tandem mass spectrometry for quantitative analysis of lipid remodeling in essential fatty acid deficient mice. Anal Biochem 279:179-188.
38. Duffin KL, Obukowicz MG, Salsgiver WJ, Welsch DJ, Shieh C, Raz A, Needleman P. 2001. Lipid remodeling in mouse liver and plasma resulting from delta6 fatty acid desaturase inhibition. Lipids 36:1203-1208.
39. Ekroos K, Shevchenko A. 2002. Simple two-point calibration of hybrid quadrupole time-of-flight instruments using a synthetic lipid standard. Rapid Commun Mass Spectrom 16:1254-1255.
40. Ekroos K, Chernushevich IV, Simons K, Shevchenko A. 2002. Quantitative profiling of phospholipids by multiple precursor ion scanning on a hybrid quadrupole time-of-flight mass spectrometer. Anal Chem 74:941-949.
41. Ekroos K, Ejsing CS, Bahr U, Karas M, Simons K, Shevchenko A. 2003. Charting molecular composition of phosphatidylcholines by fatty acid scanning and ion trap MS3 fragmentation. J Lipid Res 44:2181-2192.
42. English D. 1996. Phosphatidic acid: A lipid messenger involved in intracellular and extracellular signalling. Cell Signal 8:341-347.
43. Esch SW, Williams TD, Biswas S, Chakrabarty A, Levine SM. 2003. Sphingolipid profile in the CNS of the twitcher (globoid cell leukodystrophy) mouse: A lipidomics approach. Cell Mol Biol 49:779-787.
44. Fang J, Barcelona MJ, Semrau JD. 2000. Characterization of methanotrophic bacteria on the basis of intact phospholipid profiles. FEMS Microbiol Lett 189:67-72.
45. Fenn JB, Mann M, Meng CK, Wong SF, Whitehouse CM. 1989. Electrospray ionization for mass spectrometry of large biomolecules. Science 246: 64-71.
46. Fenn JB, Mann M, Meng CK, Wong SF, Whitehouse CM. 1990. Electrospray ionization-principles and practice. Mass Spectrom Rev 9:37-70.
47. Finck BN, Lehman JJ, Leone TC, Welch MJ, Bennett MJ, Kovacs A, Han X, Gross RW, Kozak R, Lopaschuk GD, Kelly DP. 2002. The cardiac phenotype induced by PPARα overexpression mimics that caused by diabetes mellitus. J Clin Invest 109:121-130.
48. Finck BN, Han X, Courtois M, Aimond F, Nerbonne JM, Kovacs A, Gross RW, Kelly DP. 2003. A critical role for PPARα-mediated lipotoxicity in the pathogenesis of diabetic cardiomyopathy: Modulation of phenotype by dietary fat content. Proc Natl Acad Sci USA 100:1226-1231.
49. Folch J, Lees M, Stanley GHS. 1957. A simple method for the isolation an purification of total lipids from animal tissues. J Biol Chem 226:497-509.
50. Ford DA, Rosenbloom KB, Gross RW. 1992. The primary determinant of rabbit myocardial ethanolamine phosphotransferase substrate selectivity is the covalent nature of the sn-1 aliphatic group of diradyl glycerol acceptors. J Biol Chem 267:11222-11228.
51. Ford DA, Han X, Horner CC, Gross RW. 1996. Accumulation of unsaturated acylcarnitine molecular species during acute myocardial ischemia: Metabolic compartmentalization of products of fatty acyl chain elongation in the acylcarnitine pool. Biochemistry 35:7903-7909.
52. Fridriksson EK, Shipkova PA, Sheets ED, Holowka D, Baird B, McLafferty FW. 1999. Quantitative analysis of phospholipids in functionally important membrane domains from RBL-2H3 mast cells using tandem high-resolution mass spectrometry. Biochemistry 38:8056-8063.
53. Ghosh S, Strum JC, Bell RM. 1997. Lipid biochemistry: Functions of glycerolipids and sphingolipids in cellular signaling. FASEB J 11:45-50.
54. Glaser PE, Gross RW. 1994. Plasmenylethanolamine facilitates rapid membrane fusion: A stopped-flow kinetic investigation correlating the propensity of a major plasma membrane constituent to adopt an HII phase with its ability to promote membrane fusion. Biochemistry 33: 5805-5812.
55. Glaser PE, Gross RW. 1995. Rapid plasmenylethanolamine-selective fusion of membrane bilayers catalyzed by an isoform of glyceraldehyde-3-phosphate dehydrogenase: Discrimination between glycolytic and fusogenic roles of individual isoforms. Biochemistry 34:12193-12203.
56. Goni FM, Alonso A. 1999. Structure and functional properties of diacylglycerols in membranes. Prog Lipid Res 38:1-48.
57. Goodacre R, Heald JK, Kell DB. 1999. Characterization of intact microorganisms using electrospray ionization mass spectrometry. FEMS Microbiol Lett 176:17-24.
58. Griffiths WJ. 2003. Tandem mass spectrometry in the study of fatty acids, bile acids, and steroids. Mass Spectrom Rev 22:81-152.
59. Griffiths WJ, Brown A, Reimendal R, Yang Y, Zhang J, Sjoevall J. 1996. A comparison of fast-atom bombardment and electrospray as methods of ionization in the study of sulfated- and sulfonated lipids by tandem mass spectrometry. Rapid Commun Mass Spectrom 10:1169-1174.
60. Gross RW. 1984. High plasmalogen and arachidonic acid content of canine myocardial sarcolemma: A fast atom bombardment mass spectroscopic and gas chromatography-mass spectroscopic characterization. Biochemistry 23:158-165.
61. Gross RW. 1985. Identification of plasmalogen as the major phospholipid constituent of cardiac sarcoplasmic reticulum. Biochemistry 24:1662-1668.
62. 2 and their membrane substrates. Trends Cardiovas Med 2:115-121.
63. Gross RW, Sobel BE. 1980. Isocratic high-performance liquid chromatography separation of phosphoglycerides and lysophosphoglycerides, J Chromatogr 197:79-85.
64. Grullich C, Sullards MC, Fuks Z, Merrill AH Jr, Kolesnick R. 2000. CD95(Fas/APO-1) signals ceramide generation independent of the effector stage of apoptosis. J Biol Chem 275:8650-8656.
65. Gu M, Kerwin JL, Watts JD, Aebersold R. 1997. Ceramide profiling of complex lipid mixtures by electrospray ionization mass spectrometry. Anal Biochem 244:347-356.
66. Gunnarsson T, Karlsson A, Hansson P, Johnson G, Alling C, Odham G. 1998. Determination of phosphatidylethanol in blood from alcoholic males using high-performance liquid chromatography and evaporative light scattering or electrospray mass spectrometric detection. J Chromatogr B 705:243-249.
67. Hamilton J, Greiner R, Salem N Jr, Kim H-Y. 2000. n-3 Fatty acid deficiency decreases phosphatidylserine accumulation selectively in neuronal tissues. Lipids 35:863-869.
68. Han X. 2002. Characterization and direct quantitation of ceramide molecular species from lipid extracts of biological samples by electrospray ionization tandem mass spectrometry. Anal Biochem 302:199-212.
69. Han X, Holtzman DM, McKeel DW Jr. 2001. Plasmalogen deficiency in early Alzheimers disease subjects and in animal models: Molecular characterization using electrospray ionization mass spectrometry. J Neurochem 77:1168-1180.
70. Han X, Gross RW. 1990. Plasmenylcholine and phosphatidylcholine membrane bilayers possess distinct conformational motifs. Biochemistry 29:4992-4996.
71. Han X, Gross RW. 1991a. Modulation of cardiac membrane fluidity by amphiphilic compounds and their role in the pathophysiology of myocardial infarction. In: Aloia RC, Curtain CC, Gordon LM, editors. Drug and anesthetic effects on membrane structure and function. New York: Wiley-Liss, Inc. pp 225-243.
72. Han X, Gross RW. 1991b. Proton nuclear magnetic resonance studies on the molecular dynamics of plasmenylcholine/cholesterol and phosphatidylcholine/ cholesterol bilayers. Biochim Biophys Acta 1063:129-136.
73. Han X, Gross RW. 1994. Electrospray ionization mass spectroscopic analysis of human erythrocyte plasma membrane phospholipids. Proc Natl Acad Sci USA 91:10635-10639.
74. Han X, Gross RW. 1995. Structural determination of picomole amounts of phospholipids via electrospray ionization tandem mass spectrometry. J Am Soc Mass Spectrom 6:1202-1210.
75. Han X, Gross RW. 1996. Structural determination of lysophospholipid regioisomers by electrospray ionization tandem mass spectrometry. J Am Chem Soc 118:451-457.
76. Han X, Gross RW. 2001. Quantitative analysis and molecular species fingerprinting of triacylglyceride molecular species directly from lipid extracts of biological samples by electrospray ionization tandem mass spectrometry. Anal Biochem 295:88-100.
77. Han X, Gross RW. 2003. Global analysis of cellular lipidomes directly from crude extracts of biological samples by ESI mass spectrometry: A bridge to lipidomics. J Lipid Res 44:1071-1079.
78. Han X, Gubitosi-Klug RA, Collins B, Gross RW. 1996. Alternations in individual molecular species of human platelet phospholipids during thrombin stimulation: Electrospray ionization mass spectrometry-facilitated identification of the boundary conditions for the magnitude and selectivity of thrombin-induced platelet phospholipid hydrolysis. Biochemistry 35:5822-5832.
79. Han X, Abendschein AR, Kelley JG, Gross RW. 2000. Diabetes-induced changes in specific lipid molecular species in rat myocardium. Biochem J 352:79-89.
80. Han X, Holtzman DM, McKeel DW Jr, Kelley J, Morris JC. 2002. Substantial sulfatide deficiency and ceramide elevation in very early Alzheimers disease: Potential role in disease pathogenesis. J Neurochem 82:809-818.
81. Han X, Cheng H, Fryer DJ, Fagan AM, Holtzman DM. 2003a. Novel role for apolipoprotein E in the central nervous system: Modulation of sulfatide content. J Biol Chem 278:8043-8051.
82. Han X, Fagan AM, Cheng H, Morris JC, Xiong C, Holtzman DM. 2003b. Cerebrospinal fluid sulfatide is decreased in subjects with incipient dementia. Ann Neurol 54:115-119.
83. Hannun YA. 1996. Function of ceramide in coordinating cellular responses to stress. Science 274:1855-1859.
84. Hannun YA, Luberto C. 2000. Ceramide in the eukaryotic stress response. Trends Cell Biol 10:73-80.
85. Hansen HH, Hansen SH, Schousboe A, Hansen HS. 2000. Determination of the phospholipid precursor of anandamide and other N-acylethanolamine phospholipids before and after sodium azide-induced toxicity in cultured neocortical neurons. J Neurochem 75:861-871.
86. Harrison KA, Clay KL, Murphy RC. 1999. Negative ion electrospray and tandem mass spectrometric analysis of platelet activating factor (PAF) (1-hexadecyl-2-acetyl-glycerophosphocholine). J Mass Spectrom 34: 330-335.
87. Harrison KA, Davies SS, Marathe OK, McIntyre T, Prescott S, Reddy KM, Falck JR, Murphy RC. 2000. Analysis of oxidized glycerophosphocholine lipids using electrospray ionization mass spectrometry and microderivatization techniques. J Mass Spectrom 35:224-236.
88. Hartvigsen K, Ravandi A, Bukhave K, Holmer O, Kuksis A. 2001. Regiospecific analysis of neutral ether lipids by liquid chromatography/ electrospray ionization/single quadrupole mass spectrometry: Validation with synthetic compounds. J Mass Spectrom 36: 1116-1124.
89. 2 isoform. Fast atom bombardment mass spectroscopic and reverse-phase high pressure liquid chromatography identification of choline and ethanolamine glycerophospholipid substrates. J Clin Invest 91:2513-2522.
90. Hoff HF, O'Neil J, Wu Z, Hoppe G, Salomon RL. 2003. Phospholipid hydroxyalkenals: Biological and chemical properties of specific oxidized lipids present in atherosclerotic lesions. Arteriocler Thromb Vasc Biol 23:275-282.
91. Hoischen C, Ihn W, Gura K, Gumpert J. 1997. Structural characterization of molecular phospholipid species in cytoplasmic membranes of the cell wall-less Streptomyces hygroscopicus L form by use of electrospray ionization coupled with collision-induced dissociation mass spectrometry. J Bacteriol 179:3437-3442.
92. Horrocks LA, Sharma M. 1982. Plasmalogens and O-alkyl glycerophospholipids. In: Hawthorne JN, Ansell GB, editors. Phospholipids. Amsterdam, The Netherlands: Elsevier Biomedical Press, pp 51-93.
93. Hsu F-F, Bohrer A, Turk J. 1998a. Electrospray ionization tandem mass spectrometric analysis of sulfatide. Determination of fragmentation patterns and characterization of molecular species expressed in brain and in pancreatic islets. Biochim Biophys Acta 1392:202-216.
94. Hsu F-F, Bohrer A, Turk J. 1998b. Formation of lithiated adducts of glycerophosphocholine lipids facilitates their identification by electrospray ionization tandem mass spectrometry. J Am Soc Mass Spectrom 9:516-526.
95. Hsu F-F, Turk J. 1999. Structural characterization of triacylglycerols as lithiated adducts by electrospray ionization mass spectrometry using low-energy collisionally activated dissociation on a triple stage quadrupole instrument. J Am Soc Mass Spectrom 10:587-599.
96. Hsu F-F, Turk J. 2000. Characterization of phosphatidylinositol, phosphatidylinositol-4-phosphate, and phosphatidylinositol-4,5-bisphosphate by electrospray ionization tandem mass spectrometry: A mechanistic study. J Am Soc Mass Spectrom 11:986-999.
97. Hsu F-F, Turk J. 2001. Structural determination of glycosphingolipids as lithiated adducts by electrospray ionization mass spectrometry using low-energy collisional-activated dissociation on a triple stage quadrupole instrument. J Am Soc Mass Spectrom 12:61-79.
98. Hsu F-F, Turk J. 2002. Characterization of ceramides by low energy collisional-activated dissociation tandem mass spectrometry with negative-ion electrospray ionization. J Am Soc Mass Spectrom 13: 558-570.
99. Hsu F-F, Bohrer A, Wohltmann M, Ramanadham S, Ma Z, Yarasheski K, Turk J. 2000a. Electrospray ionization mass spectrometric analyses of changes in tissue phospholipid molecular species during the evolution of hyperlipidemia and hyperglycemia in Zucker diabetic fatty rats. Lipids 35:839-854.
100. 2 activation. J Biol Chem 275:16579-16589.
101. Hsu F-F, Turk J, Thukkani AK, Messner MC, Wildsmith KR, Ford DA. 2003. Characterization of alkylacyl, alk-1-enylacyl and lyso subclasses of glycerophosphocholine by tandem quadrupole mass spectrometry with electrospray ionization. J Mass Spectrom 38:752-763.
102. Hvattum E, Larsen A, Uran S, Michelsen PM, Skotland T. 1998. Specific detection and quantification of palmitoyl-stearoyl-phosphatidylserine in human blood using normal-phase liquid chromatography coupled with electrospray mass spectrometry. J Chromatogr B 716:47-56.
103. Igbavboa U, Hamilton J, Kim H-Y, Sun GY, Wood WG. 2002. A new role for apolipoprotein E: Modulating transport of polyunsaturated phospholipid molecular species in synaptic plasma membranes. J Neurochem 80:255-261.
104. Ishida M, Hayakawa J, Imagawa M, Taguchi R. 2001. Microanalysis of phospholipids of mammalian cells by liquid chromatography/electrospray ionization-mass spectrometry. J Mass Spectrom Soc Jpn 49:150-160.
105. Ishizuka I, Yamakawa T. 1985. Glycoglycerolipids. In: Wiegandt H, editor. Glycolipids. Amsterdam, The Netherlands: Elsevier. pp 101-197.
106. Ivanova PT, Cerda BA, Horn DM, Cohen JS, McLafferty FW, Brown HA. 2001. Electrospray ionization mass spectrometry analysis of changes in phospholipids in RBL-2H3 mastocytoma cells during degranulation. Proc Natl Acad Sci USA 98:7152-7157.
107. Johnson AW, Mills K, Clayton PT. 1996. The use of automated electrospray ionization tandem MS for the diagnosis of inborn errors of metabolism from dried blood spots. Biochem Soc Trans 24:932-938.
108. Kakela R, Somerharju P, Tyynela J. 2003. Analysis of phospholipid molecular species in brains from patients with infantile and juvenile neuronalceroid lipofuscinosis using liquid chromatography-electrospray ionization mass spectrometry. J Neurochem 84:1051-1065.
109. Kalderon B, Sheena V, Shachrur S, Hertz R, Bar-Tana J. 2002. Modulation by nutrients and drugs of liver acyl-CoAs analyzed by mass spectrometry, J Lipid Res 43:1125-1132.
110. Kayganich KA, Murphy RC. 1992. Fast atom bombardment tandem mass spectrometric identification of diacyl, alkylacyl, and alk-1-enylacyl molecular species of glycerophosphoethanolamine in human polymorphonuclear leukocytes. Anal Chem 64:2965-2971.
111. Kerwin JL, Tuininga AR, Ericsson LH. 1994. Identification of molecular species of glycerophospholipids and sphingomyelin using electrospray mass spectrometry. J Lipid Res 35:1102-1114.
112. Kevala JH, Kim H-Y. 2001. Determination of substrate preference in phosphatidylserine decarboxylation by liquid chromatography-electrospray ionization mass spectrometry. Anal Biochem 292:130-138.
113. Khan WA, Blobe GC, Hannun YA. 1995. Arachidonic acid and free fatty acids as second messengers and the role of protein kinase C. Cell Signal 7: 171-184.
114. Khaselev N, Murphy RC. 2000. Electrospray ionization mass spectrometry of lysoglycerophosphocholine lipid subclasses. J Am Soc Mass Spectrom 11:283-291.
115. Kim H-Y, Akbar M, Kim K-Y. 2001. Inhibition of neuronal apoptosis by polyunsaturated fatty acids. J Mol Neurosci 16:223-227.
116. Kim H-Y, Wang TCL, Ma Y-C. 1994. Liquid chromatography/mass spectrometry of phospholipids using electrospray ionization. Anal Chem 66:3977-3982.
117. Kimelberg HK. 1985. Membrane fluidity and lipid composition. NATO ASI Series, Series A: Life Sci 71:261-276.
118. Koivusalo M, Haimi P, Heikinheimo L, Kostiainen R, Somerharju P. 2001. Quantitative determination of phospholipid compositions by ESI-MS: Effects of acyl chain length, unsaturation, and lipid concentration on instrument response. J Lipid Res 42:663-672.
119. Kolesnick RN, Goni FM, Alonso A. 2000. Compartmentalization of ceramide signaling: Physical foundations and biological effects. J Cell Physiol 184:285-300.
120. Kolesnick RN, Krönke M. 1998. Regulation of ceramide production and apoptosis. Annu Rev Physiol 60:643-665.
121. Kostiainen R, Tuominen J, Kokkonen J, Heikinheimo L, Somerharju P. 1998. Determination of phospholipid composition of cultured cells by electrospray-tandem mass spectrometry. Adv Mass Spectrom 14: C052140/1-C052140/7.
122. Lee SH, Williams MV, DuBois RN, Blair IA. 2003. Targeted lipidomics using electron capture atmospheric pressure chemical ionization mass spectrometry. Rapid Commun Mass Spectrom 17:2168-2176.
123. Lehmann WD, Koester M, Erben O, Keppler D. 1997. Characterization and quantification of rat bile phosphatidylcholine by electrospray-tandem mass spectrometry. Anal Biochem 246:102-110.
124. Lennartz MR. 1999. Phospholipases and phagocytosis: The role of phospholipid-derived second messengers in phagocytosis. Int J Biochem Cell Biol 31:415-430.
125. Liebisch G, Drobnik W, Reil M, Trumbach B, Arnecke R, Olgemoller B, Roscher A, Schmilz G. 1999. Quantitative measurement of different ceramide species from crude cellular extracts by electrospray ionization tandem mass spectrometry (ESI-MS/MS). J Lipid Res 40:1539-1546.
126. Liebisch G, Drobnik W, Lieser B, Schmilz G. 2002. High-throughput quantification of lysophosphatidylcholine by electrospray ionization tandem mass spectrometry. Clic Chem 48:2217-2224.
127. Lieser B, Liebisch G, Drobnik W, Schmitz G. 2003. Quantification of sphingosine and sphinganine from crude lipid extracts by HPLC electrospray ionization tandem mass spectrometry. J Lipid Res 44: 2209-2216.
128. Listenberger L, Han X, Lewis SE, Cases S, Farese RV Jr, Ory DS, Schaffer JE. 2003. Unsaturated fatty acids prevent lipotoxicity through induction of triglyceride accumulation. Proc Natl Acad Sci USA 100:3077-3082.
129. 2β, precipitating ventricular tachyarrhythmias in transgenic mice: Rescue of the lethal electrophysiologic phenotype by mechanism-based inhibition. J Biol Chem 278:22231-22236.
130. Mano N, Oda Y, Yamada K, Asakawa N, Katayama K. 1997, Simultaneous quantitative determination method for sphingolipid metabolites by liquid chromatography/ionspray ionization tandem mass spectrometry. Anal Biochem 244:291-300.
131. Markesbery WR. 1997. Oxidative stress hypothesis in Alzheimers disease. Free Radie Biol Med 23:134-147.
132. McClellan JE, Quarmby ST, Yost RA. 2002. Parent and neutral loss monitoring on a quadrupole ion trap mass spectrometer: Screening of acylcarnitines in complex mixtures. Anal Chem 74:5799-5806.
133. McCluer RH, Ullman MD, Jungalwala FB. 1986. HPLC of glycosphingolipids and phospholipids. Adv Chromatogr 25:309-353.
134. McLafferty FW, Turecek F. 1993. Interpretation of mass spectra. Sausalito, California: University Science Books.
135. McLafferty FW, Senko MW, Little DP, Wood TD, O'Connor PB, Speir JP, Chorush RA, Kelleher NL. 1995. Electrospray ionization and fourier transform mass spectrometry in biomedical research. Adv Mass Spectrom 13:115-128.
136. Meade EA, Jones DA, Zimmerman GA, McIntyre TM, Prescott SM. 1996. Prostaglandins and related compounds. Lipid messengers with many actions. Handbook Lipid Res 8:285-305.
137. Meisen I, Peter-Katalinic J, Muething J. 2003. Discrimination of neolactoseries gangliosides with α2-3- and α2-6-linked N-acetylneuraminic acid by nanoelectrospray ionization low-energy collision-induced dissociation tandem quadrupole TOP MS. Anal Chem 75:5719-5725.
138. Merrill AH Jr. 2002. De novo sphingolipid biosynthesis: A necessary, but dangerous, pathway. J Biol Chem 277:25843-25846.
139. Merrill AH Jr, Sweeley CC. 1996. Sphingolipids: Metabolism and cell signalling. In: Vance DE, Vance J, editors. Biochemistry of lipids, lipoproteins and membranes. Amsterdam, The Netherlands: Elsevier. pp 309-339.
140. Moeder M, Kiessling A, Loester H, Brueggemann L. 2003. The pattern of urinary acylcarnitines determined by electrospray mass spectrometry: A new tool in the diagnosis of diabetes mellitus. Anal Bioanal Chem 375:200-210.
141. Moolenaar WH. 1995. Lysophosphatidic acid signalling. Curr Op Cell Biol 7:203-210.
142. Murphy RC. 2001. Free-radical-induced oxidation of arachidonoyl plasmalogen phospholipids: Antioxidant mechanism and precursor pathway for bioactive eicosanoids. Chem Res Toxicol 14:463-472.
143. Murphy RC, Fiedler J, Hevko J. 2001. Analysis of nonvolatile lipids by mass spectrometry. Chem Rev 101:479-526.
144. Murthy M, Hamilton J, Greiner RS, Moriguchi T, Salem N Jr, Kim H-Y. 2002. Differential effects of n-3 fatty acid deficiency on phospholipid molecular species composition in the rat hippocampus. J Lipid Res 43:611-617.
145. Newberry NP, Xie Y, Kennedy S, Han X, Buhman KK, Luo J, Gross RW, Davidson NO. 2003. Decreased hepatic triglyceride accumulation and altered fatty acid uptake in mice with deletion of the liver fatty acid binding protein gene. J Biol Chem 278:51664-51672.
146. Pak JH, Han X, Gross RW. 1992. Differential molecular dynamics and transmembrane fluidity gradients in canine myocardial sarcolemma and sarcoplasmic reticulum. Chem Phys Lipids 61:111-119.
147. Paola MD, Cocco T, Lorusso M. 2000, Ceramide interaction with the respiratory chain of heart mitochondria. Biochemistry 39:6660-6668.
148. Pike LJ. 2003. Lipid rafts: Bringing order to chaos. J Lipid Res 44:655-667.
149. Pike LJ, Han X, Chung K-N, Gross RW. 2002. Lipid rafts are enriched in arachidonic acid and plasmenylethanolamine and their composition is independent of caveolin-1 expression: A quantitative electrospray ionization/mass spectrometric analysis. Biochemistry 41:2075-2088.
150. Podrez EA, Poliakov E, Shen Z, Zhang R, Deng Y, Sun M, Finton PJ, Shan L, Febbraio M, Hajjar DP, Silverstein RL, Hoff HF, Salomon RG, Hazen SL. 2002. A novel family of atherogenic oxidized phospholipids promotes macrophage foam cell formation via the scavenger receptor CD36 and is enriched in atherosclerotic lesions. J Biol Chem 277: 38517-38523.
151. Postle AD, Mander A, Reid KBM, Wang J-Y, Wright SM, Moustaki M, Warner JO, 1999. Deficient hydrophilic lung surfactant proteins A and D with normal surfactant phospholipid molecular species in cystic fibrosis. Am J Respir Cell Mol Biol 20:90-98.
152. Presti FT. 1985. Role of cholesterol in regulating membrane fluidity. Membr Fluid Biol 4:97-146.
153. Pulfer M, Murphy RC. 2003. Electrospray mass spectrometry of phospholipids. Mass Spec Rev 22:332-364.
154. Qiu D-F, Games MPL, Xiao X-Y, Games DE, Walton TJ. 2000. Characterization of membrane phospholipids and glycolipids from a halophilic archaebacterium by high-performance liquid chromatography/electrospray mass spectrometry. Rapid Commun Mass Spectrom 14:1586-1591.
155. Raith K, Neubert RHH. 1998. Structural studies on ceramides by electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 12:935-938.
156. Raith K, Neubert RHH. 2000. Liquid chromatography-electrospray mass spectrometry and tandem mass spectrometry of ceramides. Anal Chim Acta 403:295-303.
157. Ramanadham S, Hsu F-F, Bohrer A, Nowatzke W, Ma Z, Turk J. 1998. Electrospray ionization mass spectrometric analyses of phospholipids from rat and human pancreatic islets and subcellular membranes: Comparison to other tissues and implications for membrane fusion in insulin exocytosis. Biochemistry 37:4553-4567.
158. Rashed MS, Ozand PT, Harrison ME, Watkins PJF, Evans S. 1994. Electrospray tandem mass spectrometry in the diagnosis of organic acidemias. Rapid Commun Mass Spectrom 8:129-133.
159. Ravandi A, Kuksis A, Marai L, Myher JJ, Steiner G, Lewisa G, Kamido H. 1996. Isolation and identification of glycated aminophospholipids from red cells and plasma of diabetic blood. FEBS Lett 381:77-81.
160. Rietveld A, Neutz S, Simons K, Eaton S. 1999. Association of sterol- and glycosylphosphatidylinositol-linked proteins with Drosophila raft lipid microdomains. J Biol Chem 274:12049-12054.
161. Roberts LJ II. 2002. Lipids as regulators of cell function. Cell Mol Life Sci 59:727-728.
162. Rock CO, Jackowski S, Cronan JE Jr. 1996. Lipid metabolism in prokaryotes. In: Vance DE, Vance J, editors. Biochemistry of lipids, lipoproteins and membranes. Amsterdam, The Netherlands: Elsevier. pp 35-74.
163. Rodgers RP, Blumer EN, Emmett MR, Marshall AG. 2000. Efficacy of bacterial bioremediation: Demonstration of complete incorporation of hydrocarbons into membrane phospholipids from rhodococcus hydrocarbon degrading bacteria by electrospray ionization fourier transform ion cyclotron resonance mass spectrometry. Environ Sci Technol 34: 535-540.
164. Sandhoff R, Brügger B, Jeckel D, Lehmann WD, Wieland FT. 1999. Determination of cholesterol at the low picomole level by nano-electrospray ionization tandem mass spectrometry. J Lipid Res 40:126-132.
165. Scherrer LA, Gross RW. 1989. Subcellular distribution, molecular dynamics and catabolism of plasmalogens in myocardium. Mol Cell Biochem 88:97-105.
166. Schneller R, Brügger B, Sandhoff R, Zellnig G, Leber A, Lampl M, Athenstaedt K, Hrastnik C, Eder S, Daum G, Paltauf F, Wieland FT, Kohlwein SD. 1999. Electrospray ionization tandem mass spectrometry (ESI-MS/MS) analysis of the lipid molecular species composition of yeast subcellular membranes reveals acyl chain-based sorting/remodeling of distinct molecular species en route to the plasma membrane. J Cell Biol 146:741-754.
167. Schuck S, Honsho M, Ekroos K, Shevchenko A, Simons K. 2003. Resistance of cell membranes to different detergents. Proc Natl Acad Sci USA 100:5795-5800.
168. +/lipid complex. J Am Soc Mass Spectrom 14:872-880.
169. Smith PBW, Snyder AP, Harden CS. 1995. Characterization of bacterial phospholipids by electrospray ionization tandem mass spectrometry, Anal Chem 67:1824-1830.
170. Smith RD, Loo JA, Edmonds CG, Barinaga CJ, Udseth HR. 1990. New developments in biochemical mass spectrometry: Electrospray ionization. Anal Chem 62:882-899.
171. Spector AA, Yorek MA. 1985. Membrane lipid composition and cellular function. J Lipid Res 26:1015-1035.
172. Spickett CM. 2003. Analysis of phospholipid oxidation by electrospray mass spectrometry. Crit Rev Oxidative Stress Aging 1:393-409.
173. Stanley J. 2001. Lipoproteins. 3. Why do lipoproteins promote atherosclerosis? Lipid Technol 13:89-90.
174. Strittmatter WJ, Roses AD. 1996. Apolipoprotein E and Alzheimer disease. Annu Rev Neurosci 19:53-77.
175. Sugita M, Itonori S, Inagaki F, Hori T. 1989. Characterization of two glucuronic acid-containing glycosphingolipids in larvae of the green-bottle fly, Lucilia caesar. J Biol Chem 264:15028-15033.
176. Sullards MC. 2000. Analysis of sphingomyelin, glucosylceramide, ceramide, sphingosine, and sphingosine 1-phosphate by tandem mass spectrometry. Methods Enzymol 312:32-45.
177. Sullards MC, Wang E, Peng Q, Merrill AH Jr. 2003. Metabolomic profiling of sphingolipids in human glioma cell lines by liquid chromatography tandem mass spectrometry. Cell Mol Biol 49:789-797.
178. Sweetman G, Trinei M, Modha J, Kusel J, Freestone P, Fishov I, Joseleau-Petit D, Redman C, Farmer P, Noms V. 1996. Electrospray ionization mass spectrometric analysis of phospholipids of Escherichia coli. Mol Microbiol 20:233-234.
179. Taguchi R, Hayakawa J, Takeuchl Y, Ishida M. 2000. Two-dimensional analysis of phospholipids by capillary liquid chromatography/electrospray ionization mass spectrometry. J Mass Spectrom 35: 953-966.
180. Thomas RL Jr, Matsko CM, Lotze MT, Amoscato AA. 1999. Mass spectrometric identification of increased C16 ceramide levels during apoptosis. J Biol Chem 274:30580-30588.
181. Thukkani AK, Albert CJ, Wildsmith KR, Messner MC, Martinson BD, Hsu F-F, Ford DA. 2003. Myeloperoxidase-derived reactive chlorinating species from human monocytes target plasmalogens in low density lipoprotein. J Biol Chem 278:36365-36372.
182. Unger RH. 2002. Lipotoxic diseases. Ann Rev Med 53:319-336.
183. Unger RH, Orci L. 2001. Diseases of liporegulation: New perspective on obesity and related disorders. FASEB J 15:312-321.
184. Vreken P, van Lint AEM, Bootsma AH, Overmars H, Wanders RJA, van Gennip AH. 1999. Quantitative plasma acylcarnitine analysis using electrospray tandem mass spectrometry for the diagnosis of organic acidaemias and fatty acid oxidation defects. J Inherit Metab Dis 22: 302-306.
185. Watson AD, Subbanagounder G, Welsbie DS, Faull KF, Navab M, Jung ME, Fogelman AM, Berliner JA. 1999. Structural identification of a novel pro-inflammatory epoxyisoprostane phospholipid in mildly oxidized low density lipoprotein. J Biol Chem 274:24787-24798.
186. Weintraub ST, Pinckard RN, Hail M. 1991. Electrospray ionization for analysis of platelet-activating factor. Rapid Commun Mass Spectrom 5:309-911.
187. Weisgraber KH, Mahley RW. 1996. Human apolipoprotein E: The Alzheimers disease connection. FASEB J 10:1485-1494.
188. Welti R, Wang X, Williams TD. 2003. Electrospray ionization tandem mass spectrometry scan modes for plant chloroplast lipids. Anal Biochem 314:149-152.
189. Welti R, Wang X. 2004. Lipid species profiling: A high throughput approach to identify lipid compositional changes and determine the function of genes involved in lipid metabolism and signaling. Curr Op Plant Biol. 7:doi:10.1016/j.pbi.2004.03.011.
190. Welti R, Li W, Li M, Sang Y, Biesiada H, Zhou H-E, Rajashekar CB, Williams TD, Wang X. 2002. Profiling membrane lipids in plant stress responses. Role of phospholipase Dα in freezing-induced lipid changes in Arabidopsis. J Biol Chem 277:31994-32002.
191. Wenk MR, Lucast L, Di Paolo G, Romanelli AJ, Suchy SF, Nussbaum RL, Cline GW, Shulman GI, McMurray W, De Camilli P. 2003. Phosphoinositide profiling in complex lipid mixtures using electrospray ionization mass spectrometry. Nat Biotechol 21:813-817.
192. Williams SD, Hsu F-F, Ford DA. 2000. Electrospray ionization mass spectrometry analyses of nuclear membrane phospholipid loss after reperfusion of ischemic myocardium. J Lipid Res 41:1585-1595.
193. Xiao Y, Chen Y, Kennedy AW, Belinson J, Xu Y. 2000. Evaluation of plasma lysophospholipids for diagnostic significance using electrospray ionization mass spectrometry (ESI-MS) analyses. Ann NY Acad Sci 905: 242-259.
194. Xiao Y, Schwartz B, Washington M, Kennedy A, Webster K, Belinson J, Xu Y. 2001. Electrospray ionization mass spectrometry analysis of lysophospholipids in human ascitic fluids: Comparison of the lysophospholipid contents in malignant vs. nonmalignant ascitic fluids. Anal Biochem 290:302-313.
195. Xie Y, Gibbs TC, Mukhin YV, Meier KE. 2002. Role for 18:1 lysophosphatidic acid as an autocrine mediator in prostate cancer cells. J Biol Chem 277:32516-32526.
196. Yang J, Han X, Gross RW. 2003. Identification of hepatic peroxisomal phospholipase A2 and characterization of arachidonic acid-containing choline glycerophospholipids in hepatic peroxisomes. FEBS Lett 546: 247-250.
197. Yoon H-R, Kim H, Cho S-H. 2003. Quantitative analysis of acyl-lysophosphatidic acid in plasma using negative ionization tandem mass spectrometry. J Chromatog B 788:85-92.
198. Zacarias A, Bolanowski D, Bhatnagar A. 2002. Comparative measurements of multicomponent phospholipid mixtures by electrospray mass spectroscopy: Relating ion intensity to concentration. Anal Biochem 308:152-159.
199. Zoeller RA, Morand OH, Raetz CRH. 1988. A possible role for plasmalogens in protecting animal cells against photosensitized killing. J Biol Chem 263:11590-11596.