Literature Survey

Fast-Atom-Bombardment Mass Spectrometry of Lipids

Fast-atom-bombardment (FAB) mass spectrometry has been applied to the analysis of a wide range of non-volatile lipids, including triacylglycerols, phospholipids and glycolipids. It can give a great deal of invaluable information, including the nature of any polar head group, molecular species composition and regiospecific distributions of fatty acids on the glycerol backbone. With tandem mass spectrometry and charge-remote fragmentations, it is even possible to locate double bond positions. Also included here are references to the use of liquid secondary-ion (LSI) mass spectrometry, a technique that is similar to FAB MS and gives spectra that differ in minor ways only.

The following references were collected as part of our regular literature reviews for our own research purposes. We cannot claim to have covered the subject exhaustively, but we have done our best. References are listed alphabetically by the first author of a paper, but not necessarily chronologically by that author. New references may be added at irregular intervals - check the bottom of the page for when it was last updated.

As this is one of the oldest of the techniques for mass spectrometry of intact lipids, references are listed according to years of publication with those from 2000 onwards listed first, then those for the years 1990 to 1999, and finally for the years up to and including 1989.

References - 2000 to the present

  • Abe,E., Hayashi,Y., Hama,Y., Hayashi,M., Inagaki,M. and Ito,M. A novel phosphatidylcholine which contains pentadecanoic acid at sn-1 and docosahexaenoic acid at sn-2 in Schizochytrium sp F26-b. J. Biochem. (Tokyo), 140, 247-253 (2006).
  • Aiello,A., Fattorusso,E., Mangoni,A. and Menna,M. Sulcaceramide, a novel triglycosylceramide from the marine ascidian Microcosmus sulcatus. Eur. J. Org. Chem., 1047-1050 (2002).
  • Aiello,A., Fattorusso,E., Mangoni,A. and Menna,M. Three new 2,3-dihydroxy fatty acid glycosphingolipids from the Mediterranean tunicate Microcosmus sulcatus. Eur. J. Org. Chem., 734-739 (2003).
  • Allard,B., Rager,M.N. and Templier,J. Occurrence of high molecular weight lipids (C80+) in the trilaminar outer cell walls of some freshwater microalgae. A reappraisal of algaenan structure. Org. Geochem., 33, 789-801 (2002).
  • Aoki,K., Uchiyama,R., Itonori,S., Sugita,M., Che,F.S., Isogai,A., Hada,N., Hada,J., Takeda,T., Kumagai,H. and Yamamoto,K. Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells. Biochem. J., 378, 461-472 (2004).
  • Asker,D., Awad,T. and Ohta,Y. Lipids of Haloferax alexandrinus strain TMT: an extremely halophilic canthaxanthin-producing archaeon. J. Biosci. Bioeng., 93, 37-43 (2002).
  • Ben-Menachem,G., Kubler-Kielb,J., Coxon,B. Yergey,A. and Schneerson,R. A newly discovered cholesteryl galactoside from Borrelia burgdorferi. Proc. Natl. Acad. Sci. USA, 100, 7913-7918 (2003).
  • Cheng,C.F. and Gross,M.L. Applications and mechanisms of charge-remote fragmentation. Mass Spectrom. Rev., 19, 398-420 (2000).
  • Costello,C.E., Beach,D.H. and Singh,B.N. Acidic glycerol lipids of Trichomonas vaginalis and Tritrichomonas foetus. Biol. Chem., 382, 275-282 (2001).
  • Denekamp,C., Claeys,M. and Pocsfalvi,G. Mechanism of cross-ring cleavage reactions in dirhamnosyl lipids: effect of the alkali ion. Rapid Commun. Mass Spectrom., 14, 794-799 (2000).
  • Domingues,P., Domingues,M.R.M., Amado,F.M.L. and Ferrer-Correia,A.J. Characterization of sodiated glycerol phosphatidylcholine phospholipids by mass spectrometry. Rapid Commun. Mass Spectrom., 15, 799-804 (2001).
  • Fagerquist,C.K., Hellerstein,M.K., Faubert,D. and Bertrand,M.J. Elimination of the concentration dependence in mass isotopomer abundance mass spectrometry of methyl palmitate using metastable atom bombardment. J. Am. Soc. Mass Spectrom., 12, 754-761 (2001).
  • Gao,J.M., Zhang,A.L, Chen,H. and Liu,J.K. Molecular species of ceramides from the ascomycete truffle Tuber indicum. Chem. Phys. Lipids, 131, 205-213 (2004).
  • Garrido,J.L., Otero,J., Maestro,M.A. and Zapata,M. The main nonpolar chlorophyll c from Emiliania huxleyi (Prymnesiophyceae) is a chlorophyll c(2)-monogalactosyldiacylglyceride ester: a mass spectrometry study. J. Phycol., 36, 497-505 (2000).
  • Gil,J.H., Hong,J.-Y., Jung,J.H., Kim,K.-J. and Hong,J. Structural determination of monoacylglycerols extracted from marine sponge by fast atom bombardment tandem mass spectrometry. Rapid Commun. Mass Spectrom., 21, 1264-1270 (2007).
  • Griffiths,W.J. Tandem mass spectrometry in the study of fatty acids, bile acids, and steroids. Mass Spectrom. Rev., 22, 81-152 (2003).
  • Gross,M.L. . Charge-remote fragmentation: an account of research on mechanisms and applications. Int. J. Mass Spectrom., 200, 611-624 (2000).
  • Gutberlet,T., Dietrich,U., Bradaczek,H., Pohlentz,G., Leopold,K. and Fischer,W. Cardiolipin, alpha-D-glucopyranosyl, and L-lysylcardiolipin from Gram-positive bacteria: FAB MS, monofilm and X-ray powder diffraction studies. Biochim. Biophys. Acta, 1463, 307-322 (2000).
  • Hamanaka,S., Hara,M., Nishio,H., Otsuka,F., Suzuki,A. and Uchida,Y. Human epidermal glucosylceramides are major precursors of stratum corneum ceramides. J. Invest. Dermatol., 119, 416-423 (2002).
  • Herrera-Salgado,Y., Garduno-Ramirez,M.L., Vazquez,L., Rios,M.Y. and Alvarez,L. Myo-inositol-derived glycolipids with anti-inflammatory activity from Solanum lanceolatum. J. Nat. Prod., 68, 1031-1036 (2005).
  • Hikita,T., Tadano-Aritomi,K., Iida-Tanaka,N., Anand,J.K., Ishizuka,I. and Hakomori,S. A novel plasmal conjugate to glycerol and psychosine ('glyceroplasmalopsychosine') - Isolation and characterization from bovine brain white matter. J. Biol. Chem., 276, 23084-23091 (2001).
  • Hong,J., Kim,Y.H., Gil,J.H., Cho,K., Jung,J.H. and Han,S.Y. Structural determination of hexadecanoic lysophosphatidylcholine regioisomers by fast atom bombardment tandem mass spectrometry. Rapid Commun. Mass Spectrom., 16, 2089-2093 (2002).
  • Hong,J.K., Cho,K., Kim,Y.H., Cheong,C., Lee,K.S. and Jung,J.H. Structural determination of lysophosphatidylcholines extracted from marine sponges by fast atom bombardment tandem mass spectrometry. Rapid Commun. Mass Spectrom., 15, 1120-1126 (2001).
  • Hue,N., Serani,L. and Laprevote,O. Structural investigation of cyclic peptidolipids from Bacillus subtilis by high-energy tandem mass spectrometry. Rapid Commun. Mass Spectrom., 15, 203-209 (2001).
  • Inagaki,M., Shibai,M., Isobe,R. and Higuchi,R. Constituents of ophiuroidea. 1. Isolation and structure of three ganglioside molecular species from the brittle star Ophiocoma scolopendrina. Chem. Pharm. Bull., 49, 1521-1525 (2001).
  • Inagaki,M., Shiizaki,M., Hiwatashi,T., Miyamoto,T. and Higuchi,R. Constituents of crinoidea. 5. Isolation and structure of a new glycosyl inositolphosphoceramide-type ganglioside from the feather star Comanthina schlegeli. Chem. Pharm. Bull., 55, 1649-1651 (2007).
  • Iriko,H., Nakamura,K., Kojima,H., Iida-Tanaka,N., Kasama,T., Kawakami,Y., Ishizuka,I., Uchida,A., Murata,Y. and Tamai,Y. Chemical structures and immunolocalization of glycosphingolipids isolated from Diphyllobothrium hottai adult worms and plerocercoids. Eur. J. Biochem., 269, 3549-3559 (2002).
  • Itabe,H., Suzuki,K., Hosoya,R., Mori,M., Higashi,Y., Fujimoto,Y. and Takano,T. Preparation of radioactive aldehyde-containing phosphatidylcholine. Anal. Biochem., 285, 151-155 (2000).
  • Iwamori, M., Nakasa, M., Yamazaki, K., Iwamori, Y., Tanaka, K., Aoki, D., Adachi, S. and Nomura, T. Bacterial species-characteristic profiles of molecular species, and the antigenicity of phospholipids and glycolipids in symbiotic Lactobacillus, Staphylococcus and Streptococcus species. Glycoconjugate J., 29, 199-209 (2012).
  • Ji,H., Voinov,V.G., Deinzer,M.L. and Barofsky,D.F. Distinguishing between cis/trans isomers of monounsaturated fatty acids by FAB MS. Anal. Chem., 79, 1519-1522 (2007).
  • Kasai,H.F., Tsubuki,M., Takahashi,K., Honda,T. and Ueda,H. Analyses of anandamide and endocannabinoid-like compounds using collision-induced dissociation in fast atom bombardment ionization-mass spectrometry and gas chromatography/chemical ionization-mass spectrometry. Anal. Sci., 19, 1593-1598 (2003).
  • Kasai,H.F., Tsubuki,M. and Honda,T. Studies on high-energy collision-induced dissociation of endogenous cannabinoids: 2-arachidonoylglycerol and N-arachidonoylethanolamide in FAB-mass spectrometry. Anal. Sci., 22, 921-930 (2006).
  • Kawatake,S., Inagaki,M., Isobe,R., Miyamoto,T. and Higuchi,R. Isolation and structure of monomethylated GM(3)-Type ganglioside molecular species from the starfish Luidia maculata. Chem. Pharm. Bull., 50, 1386-1389 (2002).
  • Kaya,K., Morrison,L.F., Codd,G.A., Metcalf,J.S., Sano,T., Takagi,H. and Kubo,T. A novel biosurfactant, 2-acyloxyethylphosphonate, isolated from waterblooms of Aphanizomenon flos-aquae. Molecules, 11, 539-548 (2006).
  • Kim,Y.A., Park,M.S., Kim,Y.H. and Han,S.Y. Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry. Tetrahedron, 59, 2921-2928 (2003).
  • Kim,Y.H., Gil,J.H., Hong,J. and Yoo,J.S. Tandem mass spectrometric analysis of fatty acyl groups of galactolipid molecular species from wheat flour. Microchem. J., 68,143-155 (2001).
  • Kim,Y.H., Kim,E.-H., Lee,C., Kim,M.-H. and Rho,J.-R. Two new monogalactosyl diacylglycerols from brown alga Sargassum thunbergii. Lipids, 42, 395-397 (2007).
  • Kim,Y.H., So,K.Y., Limb,J.K., Jhon,G.J. and Han,S.Y. Identification of triacylglycerols containing two short-chain fatty acids at sn-2 and sn-3 positions from bovine udder by fast atom bombardment tandem mass spectrometry. Rapid Commun. Mass Spectrom., 14, 2230-2237 (2000).
  • Korachi,M., Blinkhorn,A.S. and Drucker,D.B. Analysis of phospholipid molecular species distributions by fast atom bombardment mass spectrometry (FAB-MS). Eur. J. Lipid Sci. Technol., 104, 50-56 (2002).
  • Kurvinen,J.P., Sjovall,O. and Kallio,H. Molecular weight distribution and regioisomeric structure of triacylglycerols in some common human milk substitutes. J. Am. Oil Chem. Soc., 79, 13-22 (2002).
  • Lee,S., Kang,S.Y., Kim,N. and Jung,S.H. Structural analyses of the novel phosphoglycolipids containing the unusual very long bifunctional acyl chain, alpha,omega-13,16-dimethyloctacosanedioate in Thermoanaerobacter ethanolicus. Bull. Korean Chem. Soc., 23, 1778-1784 (2002).
  • Mahmoudabadi,A.Z. and Drucker,D.B. Comparison of polar lipids from yeast and mycelial forms of Candida albicans and Candida dubliniensis. Mycoses, 49, 18-22 (2006).
  • Mahmoudabadi,A.Z., Boote,V. and Drucker,D.B. Characterization of polar lipids of oral isolates of Candida, Pichia and Saccharomyces by Fast Atom Bombardment Mass Spectrometry (FAB MS). J. Appl. Microbiol., 90, 668-675 (2001).
  • Mederos,L., Valdivia,J.A. and Valero-Guillen,P.L. Analysis of the structure of mycolic acids of Mycobacterium simiae reveals a particular composition of alpha-mycolates in strain 'habana' TMC 5135, considered as immunogenic in tuberculosis and leprosy. Microbiology, 153, 4159-4165 (2007).
  • Moreau,R.A. An overview of modern mass spectrometry methods in the toolbox of lipid chemists and biochemists. In: Lipid Analysis and Lipidomics: New Techniques and Applications. pp. 29-49 (ed: M.M. Mossoba, J.K.G. Kramer, J.T. Brenna and R.E. McDonald, AOCS Press, Champaign, USA) (2006).
  • Murphy,R.C., Fiedler,J. and Hevko,J. Analysis of nonvolatile lipids by mass spectrometry. Chem. Rev. 101, 479-526 (2001).
  • Naka,T., Fujiwara,N., Yabuuchi,E., Doe,M., Kobayashi,K., Kato,Y. and Yano,I. A novel sphingoglycolipid containing galacturonic acid and 2-hydroxy fatty acid in cellular lipids of Sphingomonas yanoikuyae. J. Bact., 182, 2660-2663 (2000).
  • Naka,T., Fujiwara,N., Yano,I., Maeda,S., Doe,M., Minamino,M., Ikeda,N., Kato,Y., Watabe,K., Kumazawa,Y., Ikuko Tomiyasu,I. and Kobayashi,K. Structural analysis of sphingophospholipids derived from Sphingobacterium spiritivorum, the type species of genus Sphingobacterium. Biochim. Biophys. Acta, 1635, 83-92 (2003).
  • Nemoto,N., Shida,Y., Shimada,H., Oshima,T. and Yamagishi,A. Characterization of the precursor of tetraether lipid biosynthesis in the thermoacidophilic archaeon Thermoplasma acidophilum. Extremophiles, 7, 235-243 (2003).
  • Nichols,D.S. and McMeekin,T.A. Biomarker techniques to screen for bacteria that produce polyunsaturated fatty acids. J. Microb. Methods, 48, 161-170 (2002).
  • Nishihara,M., Morii,H., Matsuno,K., Ohga,M., Stetter,K.O., and Koga,Y. Structure analysis by reductive cleavage with LiAlH4 of an allyl ether choline-phospholipid, archaetidylcholine, from the hyperthermophilic Methanoarchaeon Methanopyrus kandleri. Archaea, 1, 123-131 (2002).
  • Noda,N., Umebayashi,K., Nakatani,T., Miyahara,K. and Ishiyama,K. Isolation and characterization of some hydroxy fatty and phosphoric acid esters of 10-hydroxy-2-decenoic acid from the royal jelly of honeybees (Apis mellifera). Lipids, 40, 833-838 (2005).
  • Ohashi,Y., Tanaka,T., Akashi,S., Morimoto,S., Kishimoto,Y. and Nagai,Y. Squid nerve sphingomyelin containing an unusual sphingoid base. J. Lipid Res., 41, 1118-1124 (2000).
  • Pinto,M.R., Rodrigues,M.L., Travassos,L.R., Haido,R.M.T., Wait,R. and Barreto-Bergter,E. Characterization of glucosylceramides in Pseudallescheria boydii and their involvement in fungal differentiation. Glycobiology, 12, 251-260 (2002).
  • Pocsfalvi,G., Malorni,A., Mancini,I., Guella,G. and Pietra,F. Molecular characterization of a highly heterogeneous mixture of glucosylceramides from a deep-water Mediterranean scleractinian coral Dendrophyllia cornigera. Rapid Commun. Mass Spectrom., 14, 2247-2259 (2000).
  • Sang,S.M., Lao,A., Wang,Y.S., Chin,C.K., Rosen,R.T. and Ho,C.T. Antifungal constituents from the seeds of Allium fistulosum L. J. Agric. Food Chem., 50, 6318-6321 (2002).
  • Saitoh,M., Itoh,M., Takashima,S., Mizuguchi,M. and Iwamori,M. Phosphatidyl ethanolamine with increased polyunsaturated fatty acids in compensation for plasmalogen defect in the Zellweger syndrome brain. Neurosci. Letts, 449, 164-167 (2009).
  • Sata,N.U., Kaneniwa,M., Masuda,Y., Yasuhiro Ando,Y. and Iida,H. Fatty acid composition of two species of Japanese freshwater sponges Heterorotula multidentata and Spongilla alba. Fisheries Sci., 68, 236-238 (2002).
  • Sim,K.G., Hammond,J. and Wilcken,B. Strategies for the diagnosis of mitochondrial fatty acid beta-oxidation disorders. Clin. Chim. Acta, 323, 37-58 (2002).
  • Siristova,L., Melzoch,K. and Rezanka,T. Fatty acids, unusual glycophospholipids and DNA analyses of thermophilic bacteria isolated from hot springs. Extremophiles, 13, 101-109 (2009).
  • Son,B.W., Kim,J.C. and Choi,H.D. A new diacylgalactolipid containing 4Z-16:1 from the marine cyanobacterium Oscillatoria sp. Lipids, 36, 427-429 (2001).
  • Sprott,G.D., Larocque,S., Cadotte,N., Dicaire,C.J., McGee,M. and Brisson,J.R. Novel polar lipids of halophilic eubacterium Planococcus H8 and archaeon Haloferax volcanii. Biochim. Biophys. Acta, 1633, 179-188 (2003).
  • Sprott,G.D., Bakouche,L. and Rajagopal,K. Identification of sulfoquinovosyl diacylglycerol as a major polar lipid in Marinococcus halophilus and Salinicoccus hispanicus and substitution with phosphatidylglycerol. Can. J. Microbiol., 52, 209-219 (2006).
  • Sullards,M.C. Analysis of sphingomyelin, glucosylceramide, ceramide, sphingosine, and sphingosine 1-phosphate by tandem mass spectrometry. Methods Enzymol. Sphingolipid Metabolism and Cell Signaling, Part B, 312, 32-45 (2000).
  • Tadano-Aritomi,K., Hikita,T., Fujimoto,H., Suzuki,K., Motegi,K. and Ishizuka,I. Kidney lipids in galactosylceramide synthase-deficient mice: absence of galactosylsulfatide and compensatory increase in more polar sulfoglycolipids. J. Lipid Res., 41, 1237-1243 (2000).
  • Tadano-Aritomi,K., Hikita,T., Kubota,M., Kasama,T., Toma,K., Hakomori,S. and Ishizuka,I. Internal residue loss produced by rearrangement of a novel cationic glycosphingolipid, glyceroplasmalopsychosine, in collision-induced dissociation. J. Mass Spectrom., 38, 715-722 (2003).
  • Takaichi,S., Matsui,K., Nakamura,M., Muramatsu,M. and Hanada,S. Fatty acids of astaxanthin esters in krill determined by mild mass spectrometry. Comp. Biochem. Physiol. B, 136, 317-322 (2003).
  • Uchida,Y., Hara,M., Nishio,H., Sidransky,E., Inoue,S., Otsuka,F., Suzuki,A.., Elias,P.M., Holleran,W.M. and Hamanaka,S. Epidermal sphingomyelins are precursors for selected stratum corneum ceramides. J. Lipid Res., 41, 2071-2082 (2000).
  • Uda,I., Sugai,A., Itoh,Y.H. and Itoh,T. Characterization of caldarchaetidylglycerol analogs, dialkyl-type and trialkyl-type, from Thermoplasma acidophilum. Lipids, 35, 1155-1157 (2000).
  • Uda,I., Sugai,A., Shimizu,A., Itoh,Y.H. and Itoh,T. Glucosylcaldarchaetidylglycerol, a minor phosphoglycolipid from Thermoplasma acidophilum Biochim. Biophys. Acta, 1484, 83-86 (2000).
  • Vorob'eva,E.V., Dmitrenok,A.S., Dmitrenok,P.S., Isakov,V.V., Krasikova,I.N. and Solov'eva,T.F. The structure of uncommon lipid A from the marine bacterium Marinomonas communis ATCC 27118(T). Russ. J. Bioorg. Chem., 31, 362-371 (2005).
  • Xu,X., Horibata,Y., Inagaki,M., Hama,Y., Sakaguchi,K., Goda,H.M., Okino,N. and Ito,M. A novel fucosyl glycosphingolipid of brine shrimp that is highly sensitive to endoglycoceramidase. Glycobiology, 19, 1446-1451 (2009).
  • Xu,X., Monjusho,H., Inagaki,M., Hama,Y., Yamaguchi,K., Sakaguchi,K., Iwamori,M., Okino,N. and Ito,M. Fucosyl-GM1a, an endoglycoceramidase-resistant ganglioside of porcine brain. J. Biochem., 141, 1-7 (2007).
  • Yague,G., Segovia,M. and Valero-Guillen,P.L. Detection of mycoloylglycerol by thin-layer chromatography as a tool for the rapid inclusion of corynebacteria of clinical origin in the genus Corynebacterium. J. Chromatogr. B, 738, 181-185 (2000).
  • Yague,G., Segovia,M. and Valero-Guillen,P.L. Phospholipid composition of several clinically relevant Corynebacterium species as determined by mass spectrometry: an unusual fatty acyl moiety is present in inositol-containing phospholipids of Corynebacterium urealyticum. Microbiology, 149,1675-1685 (2003).
  • Yamada,K., Hamada,A., Kisa,F., Niyamoto,T. and Higuchi,R. Constituents of holothuroidea, 13. Structure of neuritogenic active ganglioside molecular species from the sea cucumber Stichopus chloronotus. Chem. Pharm. Bull., 51, 46-52 (2003).
  • Yamada,K., Matsubara,R., Kaneko,M., Miyamoto,T. and Higuchi,R. Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota. Chem. Pharm. Bull., 49, 447-452 (2001).
  • Yamada,K., Sasaki,K., Harada,Y., Isobe,R. and Higuchi,R. Constituents of holothuroidea, 12. Isolation and structure of glucocerebrosides from the sea cucumber Holothuria pervicax. Chem. Pharm. Bull., 50, 1467-1470 (2002).
  • Yli-Jokipii,K.M., Schwab,U.S., Tahvonen,R.L., Kurvinen,J.P., Mykkanen,H.M. and Kallio,H.P.T. Triacylglycerol molecular weight and to a lesser extent, fatty acid positional distribution, affect chylomicron triacylglycerol composition in women. J. Nutr., 132, 924-929 (2002).
  • Yoshino,J., Sugiyama,Y., Sakuda,S., Kodama,T., Nagasawa,H., Ishii,M. and Igarashi,Y. Chemical structure of a novel aminophospholipid from Hydrogenobacter thermophilus strain TK-6. J. Bact., 183, 6302-6304 (2001).
  • Zapata,M., Edvardsen,B., Rodriguez,F., Maestro,M.A. and Garrido,J.L. Chlorophyll c(2) monogalactosyldiacylglyceride ester (chl c(2)-MGDG). A novel marker pigment for Chrysochromulina species (Haptophyta). Marine Ecology-Progress Series, 219, 85-98 (2001).

 

References - 1990 to 1999

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Updated February 27, 2013