Literature Survey

Gas Chromatography of Diacylglycerol Derivatives (derived from Phospholipids)

Gas chromatography is a powerful technique for separation of diacylglycerol derivatives, including those derived from phospholipids, although it may not be the easiest from a technical standpoint.

The following references were collected as part of our regular literature reviews for our own research purposes, and cover the years 1985 to the present. 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.

I can especially recommend the papers by Arnis Kuksis and colleagues cited below.

  • Aveldano,M.I., A novel group of very long chain polyenoic fatty acids in dipoly-unsaturated phosphatidylcholines from vertebrate retina. J. Biol. Chem., 262, 1172-1179 (1987).
  • Balazy,M., Cluzel,J. and Bazan,N.G. A novel method for the analysis of PAF and alkyl ether phospholipids by mass spectrometry. Adv. Prostaglandins, Thromboxanes & Leukotrienes, 21, 323-326 (1990).
  • Bossant,M.J., Farinotti,R., De Maack,F., Mahuzier,G., Benveniste,J. and Ninio,E., Capillary GC and Tandem MS of Paf-acether and analogs: absence of 1-O-alkyl-2-propionyl-sn-glycero-3-phosphocholine in human polymorphonuclear neutrophils. Lipids, 24, 121-124 (1989).
  • Bossant,M.J., Farinotti,R., Mencia-Huerta,J.M., Benveniste,J. and Mahuzier,G., Characterisation and quantification of paf-acether (platelet-activating factor) as a heptafluorobutyrate derivative by capillary column GC with electron-capture detection. J. Chromatogr., 423, 23-32 (1987).
  • Bradley, A.S., Fredricks,H., Hinrichs,K.-U. and Summons,R.E. Structural diversity of diether lipids in carbonate chimneys at the Lost City Hydrothermal Field. Org. Geochem., 40, 1169-1178 (2009).
  • Bruschweiler, H. and Dieffenbacher,A. Determination of mono- and diglycerides by capillary GC. Pure Appl. Chem., 63, 1153-62 (1991).
  • Chapman, D.J. and Barber,J., Polar lipids of chloroplast membranes. Methods Enzymol., 148, 294-319 (1987).
  • Chen, S. and Claeys,M. Characterization of omega-3-docosahexaenoic acid-containing molecular species of phospholipids in rainbow trout liver. J. Sci. Food Agric., 44, 3120-3125 (1996).
  • Christie, W.W. and Han, X. Lipid Analysis - Isolation, Separation, Identification and Lipidomic Analysis (4th edition), 446 pages (Oily Press, Bridgwater, U.K. and Woodhead Publishing Ltd, Cambridge, U.K.) (2010) - Woodhead Publishing Ltd.
  • Christman, B.W. and Blair,I.A., Analysis of platelet activating factor in human saliva by GC-MS. Biomed. Environ. Mass Spectrom., 18, 258-264 (1989).
  • Coene, J., Van den Eeckhout,E. and Herdewijn,P. GC determination of alkyl lysophospholipids after solid-phase extraction from culture media. J. Chromatogr., 612, 21-26 (1993).
  • Dasgupta, A. and Banerjee,P. Microwave induced rapid preparation of acetyl, trifluoroacetyl and tert-butyl dimethylsilyl derivatives of fatty alcohols and diacylglycerols for GC-MS analysis. Chem. Phys. Lipids, 65, 217-224 (1993).
  • Evershed, R.P. Application of modern mass spectrometric techniques to the analysis of lipids. in 'Developments in the Analysis of Lipids', pp. 123-160 (edited by J.H.P. Tyman and M.H. Gordon, Royal Soc. Chem., Cambridge). (1994).
  • Hanahan,D.J. and Kumar,R., Platelet activating factor: chemical and biochemical characteristics. Prog. Lipid Res., 26, 1-28 (1987).
  • Haroldsen,P.E., Clay,K.L. and Murphy,R.C., Quantitation of lyso-platelet activating factor molecular species from human neutrophils by mass spectrometry. J. Lipid Res., 28, 42-49 (1987).
  • Hazel,J.R. and Zerba,E., Adaptation of biological membranes to temperature: molecular species composition of PC and PE in mitochondrial and microsomal membranes of liver from thermally-acclimated trout. J. Comp. Physiol. B. 156, 665-674 (1986).
  • Holub,B.C. and Skeaff,C.M., Nutritional regulation of cellular phosphatidylinositol. Methods Enzymol., 141, 234-244 (1987).
  • Jeong,B.Y., Ohshima,T. and Koizumi,C. Molecular species of 1-O-alk-1-enyl-2-acyl-, 1-O-alkyl-2-acyl- and 1,2-diacyl glycerophospholipids in Japanese oyster, Crassostrea gigas (Thunberg). Lipids, 25, 624-632 (1990).
  • Jeong,Y., Ohshima,T. and Koizumi,C. Changes in molecular species compositions of glycerophospholipids in Japanese oyster Crassostrea gigas (Thunberg) during frozen storage. Comp. Biochem. Physiol., 100B, 99-105 (1991).
  • Kuksis,A. Inositol Phospholipid Metabolism and Phosphatidyl Inositol Kinases (Laboratory Techniques in Biochemistry and Molecular Biology Vol. 30) (Elsevier, Amsterdam) (2003).
  • Kuksis,A. and Myher,J.J., General strategies for practical chromatographic analysis of lipids. in 'Chromatography of Lipids in Biomedical Research and Clinical Diagnosis', (ed. A. Kuksis, Elsevier, Amsterdam) pp. 1-47 (1987).
  • Kuksis,A., Marai,L., Myher,J.J. and Pind,S., LC/MS of natural glycerolipids, sterols and steryl esters. in 'Chromatography of Lipids in Biomedical Research and Clinical Diagnosis', (ed. A.Kuksis, Elsevier, Amsterdam), pp. 403-440 (1987).
  • Kuksis,A. Lipids. in J. Chromatogr. Library. Vol. 51. Part B., pp. B171-B227 (edited by E. Heftmann, Elsevier, Amsterdam) (1992).
  • Kuksis,A. and Myher,J.J. Mass analysis of molecular species of diradylglycerols. in 'Methods in Inositide Research', pp. 187-216 (edited by R.F. Irvine, Raven Press, New York) (1990).
  • Kuksis,A., Marai,L., Myher,J.J., Itabashi,Y. and Pind,S. Applications of GC/MS, LC/MS and FAB/MS to determination of molecular species of glycerolipids. in Analyses of Fats, Oils and Lipoproteins, pp. 464-495 (ed. E.G. Perkins, American Oil Chemists' Society, Champaign, U.S.A.) (1991).
  • Liepkalns,V.A., Myher,J.J., Kuksis,A., Leli,U., Freysz,N. and Hauser,G. Molecular species of glycerophospholipids and diacylglycerols of cultured SH-SY-5Y human neuroblastoma cells. Biochem. Cell Biol., 71, 141-149 (1993).
  • Legrand,A.B., Wang,J.M., Sobo,G., Blair,I.A., Brash,A.R. and Oates,J.A. Incorporation of 12(S)-hydroxyeicosatetraenoic acid into the phosphatidylcholine signaling pathway. Biochim. Biophys. Acta, 1301, 150-160 (1996).
  • Lynch,D.V. and Steponkus,P.L., Plasma membrane lipid alterations associated with cold acclimation of winter rye seedlings (Secale cereale L. cv. Puma). Plant Physiol., 83, 761-767 (1987).
  • Lynch,D.V. and Thompson,G.A., Analysis of phospholipid molecular species by gas chromatography and coupled gas chromatography-mass spectrometry. in 'Modern Methods of Plant Analysis. 3. Gas Chromatography/Mass spectrometry', pp. 100-120 (edited by H.S. Liskens and J.F. Jackson, Springer-Verlag, Berlin) (1986).
  • Mahadevappa,V.G. and Holub,B.J., Chromatographic analysis of phosphoinositides and their breakdown products in activated blood platelets/neutrophils. in 'Chromatography of Lipids in Biomedical Research and Clinical Diagnosis', (ed. A.Kuksis, Elsevier, Amsterdam), pp. 225-265 (1987).
  • Mares,P., High temperature capillary GLC of triacylglycerols and other intact lipids. Prog. Lipid Res., 27, 107-133 (1988).
  • Menguy,L., Christon,R., van Dorsselaer,A. and Leger,C.L. Apparent relative retention of the phosphatidylethanolamine molecular species 18:0-20:5(n-3), 16:0-22:6(n-3) and the sum 16:0-20:4(n-6) + 16:0-20:3(n-9) in the liver microsomes of pig on an EFA deficient diet. Biochim. Biophys. Acta, 1123, 41-50 (1992).
  • Murphy,R.C. Mass Spectrometry of Lipids (Handbook of Lipid Research, Vol. 7) (Plenum Press, N.Y.) (1993).
  • Myher,J.J., Kuksis,A., Pind,S. and Kay,E.R.M., Molecular species of glycerolipids of Ehrlich Ascites cells and of their fat granules. Lipids, 23, 398-404 (1988).
  • Nakagawa,Y. and Waku,K., Phospholipids. in 'Neuromethods 7. Lipids and Related Compounds', (ed. A.A. Boulton,G.B. Baker & L.A. Horrocks, Humana Press, Clifton) pp. 149-178 (1988).
  • Nichols,P.D., Shaw,P.M., Mancuso,C.A. and Franzmann,P.D. Analysis of archaeal phospholipid-derived di- and tetraether lipids by high temperature capillary GC. J. Microbial Meth., 18, 1-9 (1993).
  • Ohshima,T. and Koizumi,C. Selected ion monitoring GC/MS of 1,2-diacylglycerol tert-butyldimethylsilyl ethers derived from glycerophospholipids. Lipids, 26, 940-947 (1991).
  • Olsson,N.U. and Kaufmann,P. Optimized method for the determination of 1,2-diacyl-sn-glycero-3-phosphocholine and 1,2-diacyl-sn-glycero-3-phosphoethanolamine molecular species by enzymatic hydrolysis and GC. J. Chromatogr., 600, 257-266 (1992).
  • Phillips,N.J., Adin,D.M., Stabb,E.V., McFall-Ngai,M.J., Apicella,M.A. and Gibson,B.W. The Lipid A from Vibrio fischeri lipopolysaccharide: a unique structure bearing a phosphoglycerol moiety. J. Biol. Chem., 286, 21203-21219 (2011).
  • Pruzanski,W., Stefanski,E., de Beer,F.C., de Beer,M.C., Ravandi,A. and Kuksis,A. Comparative analysis of lipid composition of normal and acute-phase high density lipoproteins. J. Lipid Res., 41, 1035-1047 (2000).
  • Ratnayake,W.M.N. and Ackman,R.G., Lipid analyses: Part II in 'The Role of Fats in Human Nutrition' (eds. A.J. Vergroesen & M. Crawford) pp. 515-565 (Academic Press Ltd, London) (1989).
  • Rezanka,T. and Mares,P. Preparative separation of sphingolipids and of individual molecular species by HPLC and their identification by GC-MS. J. Chromatogr., 509, 333-346 (1990).
  • Roberts,W.L., Myher,J.J., Kuksis,A. and Rosenberry,T.L., Alkylacylglycerol molecular species in the glycosylinositol phospholipid membrane anchor of bovine erythrocyte acetylcholinesterase. Biochem. Biophys. Res. Commun., 150, 271-277 (1988).
  • Roberts,W.L., Myher,J.J., Kuksis,A., Low,M.G. and Rosenberry,T.L., Lipid analysis of the glycoinositol phospholipid membrane anchor of human erythrocyte acetylcholinesterase. J. Biol. Chem., 163, 18766-18775 (1988).
  • Robinson,B.S., Johnson,D.W. and Poulos,A. Unique molecular species of phosphatidylcholine containing very-long-chain (C24-C38) polyenoic fatty acids in rat brain. Biochem. J., 265, 763-767 (1990).
  • Robinson,B.S., Johnson,D.W. and Poulos,A. Novel molecular species of sphingomyelin containing 2-hydroxylated polyenoic very-long-chain fatty acids in mammalian testes and spermatozoa. J. Biol. Chem., 267, 1746-1751 (1992).
  • Saito,K., Satouchi,K., Kino,M., Ogino,H. and Oda,M., GC/MS of molecular species of phospholipids. in 'Chromatography of Lipids in Biomedical Research and Clinical Diagnosis', (ed. A.Kuksis, Elsevier, Amsterdam), pp. 378-402 (1987).
  • Salas,J.J., Martinez-Force,E. and Garces,R. Phospholipid molecular profiles in the seed kernel from different sunflower (Helianthus annuus) mutants. Lipids, 41, 805-811 (2006).
  • Smith,G.M. and Djerassi,C., Phospholipid studies of marine organisms. 14. Ether lipids of the sponge Tethya aurantica. Lipids, 22, 236-240 (1987).
  • Sugatani,J., Fujimura,K., Miwa,M., Satouchi,K. and Saito,K. Molecular heterogeneity of platelet-activating factor (PAF) in rat glandular stomach determined by GC/MS. PAF molecular species changes upon water-immersion stress. Lipids, 26, 1347-1353 (1991).
  • Tokumura,A., Takauchi,K., Tsuyoshi,A., Kamiyasu,K., Tadashi,O. and Tsukatani,H., Novel molecular analogues of phosphatidylcholines in a lipid extract from bovine brain; 1-long-chain acyl-2-short-chain acyl-sn-glycero-3-phosphocholines. J. Lipid Res., 30, 219-224 (1989).
  • Tokumura,A., Yoshioka,Y., Tsukatani,H. and Handa,Y., GC-MS analyses of ether linked lysophosphatidic acid and its analogues. Biomed. Envir. Mass Spectrom., 13, 175-180 (1986).
  • Tserng,K.Y. and Griffin,R. Studies of lipid turnover in cells with stable isotope and gas chromatograph-mass spectrometry. Anal. Biochem., 325, 344-353 (2004).
  • Tserng,K.Y. and Griffin,R. Quantitation and molecular species determination of diacylglycerols, phosphatidylcholines, ceramides, and sphingomyelins with gas chromatography. Anal. Biochem., 323, 84-93 (2003).
  • Turk,J., Bohrer,A., Stump,W.T., Ramanadham,S. and Mangino,M.J. Quantification of distinct molecular species of 2-lyso metabolites of platelet-activating factor by GC-negative ion chemical ionization MS. J. Chromatogr., 575, 183-196 (1992).
  • 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. Variation in molecular species of polar lipids from Thermoplasma acidophilum depends on growth temperature. Lipids, 36, 103-105 (2001).
  • Uemura,M. and Steponkus,P.L., A contrast of the plasma membrane lipid composition of oats and rye leaves in relation to freezing tolerance. Plant Physiol., 104, 479-496 (1994).
  • Virtue,P., Nichols,P.D. and Boon,P.I. Simultaneous estimation of microbial phospholipid fatty acids and diether lipids by capillary gas chromatography. J. Microb. Methods, 25, 177-185 (1996).
  • Weintraub,S.T., Lear,C. and Pinckard,R.N. Differential electron capture mass spectral response of pentafluorobenzoyl derivatives of platelet activating factor alkyl chain homologues. Biol. Mass Spectrom., 22, 559-564 (1993).
  • Weintraub,S.T., Pinckard,R.N., Heath,T.G. and Gage,D.A. Novel mass spectral fragmentation of heptafluorobutyryl derivatives of acyl analogs of platelet-activating factor. J. Am. Soc. Mass Spectrom., 2, 476-482 (1991).
  • Yamada,K., Asano,O., Yoshimura,T. and Katayama,K., Highly sensitive GC-MS method for the determination of platelet-activating factor in human blood. J. Chromatogr., 433, 243-247 (1988).
  • Yasuda,K., Satouchi,K., Nakayama,R. and Saito,K., Acyl type platelet-activating factor in normal rat uterus determined by GC-MS. Biomed. Environ. Mass Spectrom., 16, 207-210 (1987).
  • Yon,C. and Han,J.S. Analysis of trimethylsilyl derivatization products of phosphatidylethanol by gas chromatography-mass spectrometry. Exp. Mol. Med., 32, 243-245 (2000).
  • Yu,B.Y. and Cronholm,T. Coupling of ethanol metabolism to lipid biosynthesis: Labelling of the glycerol moieties of sn-glycerol-3-phosphate, a phosphatidic acid and a phosphatidylcholine in liver of rats given [1,1-H-2(2)]ethanol. Biochim. Biophys. Acta, 1344, 165-170 (1997).

 

Updated: February 27, 2013