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Silver-Ion Chromatography of Glycerolipids

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Encyclopedia of Lipidomics

Synonyms

Ag-LC of glycerolipids

Introduction

The ability of silver ion and some other metal ions to interact with double bonds (DBs) is well known for a long time (Dewar 1951). Silver ion chromatography, sometimes called argentation chromatography, is a separation technique based on the formation of weak reversible charge-transfer complexes between silver ion and DB of unsaturated organic molecules. Silver ion chromatography can be performed either in a planar arrangement (silver ion thin layer chromatography) or in column, which is often used for preparative purposes or silver ion high-performance liquid chromatography (Ag-HPLC) used for high-resolution separations.

The retention in the Ag-HPLC is governed by the DB number. More DB means stronger interactions and therefore higher retention times. In practice, the situation is not as simple because other factors have to be taken into account, such as the DB geometry (cis vs. trans), distances among individual DB (from the conjugation...

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References

  • Adlof R. Analysis of triacylglycerol and fatty acid isomers by low-temperature silver-ion high performance liquid chromatography with acetonitrile in hexane as solvent: Limitations of the methodology. J Chromatogr A. 2007;1148:256–9.

    Article  CAS  PubMed  Google Scholar 

  • Adlof RO. Separation of cis and trans unsaturated fatty acid methyl-esters by silver ion high-performance liquid chromatography. J Chromatogr A. 1994;659:95–9.

    Article  CAS  Google Scholar 

  • Adlof R, List G. Analysis of triglyceride isomers by silver-ion high-performance liquid chromatography – Effect of column temperature on retention times. J Chromatogr A. 2004;1046:109–13.

    Article  CAS  PubMed  Google Scholar 

  • Adlof RO, Menzel A, Dorovska-Taran V. Analysis of conjugated linoleic acid-enriched triacylglycerol mixtures by isocratic silver-ion high-performance liquid chromatography. J Chromatogr A. 2002;953:293–7.

    Article  CAS  PubMed  Google Scholar 

  • Bressan G, Broggi R, Lachi MP, Segre AL. Complexes of silver perchlorate with alpha omega-diolefins. J Organomet Chem. 1967;9:355–60.

    Article  CAS  Google Scholar 

  • Byrdwell WC. Atmospheric pressure chemical ionization mass spectrometry for analysis of lipids. Lipids. 2001;36:327–46.

    Article  CAS  PubMed  Google Scholar 

  • Chatt J, Duncanson LA. Olefin co-ordination compounds. 3. Infra-red spectra and structure – attempted preparation of acetylene complexes. J Chem Soc. 1953;2939–2947.

    Google Scholar 

  • Christie WW. A Stable silver-loaded column for the separation of lipids by high-performance liquid-chromatography. J High Res Chromatog. 1987;10:148–50.

    Article  CAS  Google Scholar 

  • Christie WW. Separation of molecular-species of triacylglycerols by high-performance liquid- with a silver ion column. J Chromatography. 1988;454:273–84.

    Article  CAS  Google Scholar 

  • Conacher HBS. Chromatographic determination of cis-trans monoethylenic unsaturation in fats and oils – review. J Chromatogr Sci. 1976;14:405–11.

    Article  CAS  PubMed  Google Scholar 

  • Correa RA, Ferraz V, Medvedovici A, Sandra P, Cerne K, David F. Positional and configurational separation of fatty acid isomers by micro reversed-phase liquid chromatography with an Ag+-containing mobile phase. J Chromatogr A. 1999;848:83–93.

    Article  CAS  Google Scholar 

  • Cvetanović RJ, Duncan FJ, Falconer WE, Irwin RS. Secondary deuterium isotope effects on stability of silver ion-olefin complexes. J Am Chem Soc. 1965;87:1827–32.

    Article  Google Scholar 

  • Delmonte P, Kataoka A, Corl BA, Bauman DE, Yurawecz MP. Relative retention order of all isomers of cis/trans conjugated linoleic acid FAME from the 6,8- to 13,15-positions using silver ion HPLC with two elution systems. Lipids. 2005;40:509–14.

    Article  CAS  PubMed  Google Scholar 

  • Dewar JS. A review of the pi-complex theory. Bull Soc Chim Fr. 1951;18:C71–9.

    Google Scholar 

  • Dugo, P., Kumm, T., Crupi, M.L., Cotroneo, A., Mondello, L., 2006. Comprehensive two-dimensional liquid chromatography combined with mass spectrometric detection in the analyses of triacylglycerols in natural lipidic matrixes. J Chromatogr A 1112, 269-275.

    Google Scholar 

  • Dugo P, Kumm T, Lo Presti M, Chiofalo B, Salimei E, Fazio A, Cotroneo A, Mondello L. Determination of triacylglycerols in donkey milk by using high performance liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry. J Sep Sci. 2005;28:1023–30.

    Article  CAS  PubMed  Google Scholar 

  • Herrera LC, Potvin MA, Melanson JE. Quantitative analysis of positional isomers of triacylglycerols via electrospray ionization tandem mass spectrometry of sodiated adducts. Rapid Commun Mass Spectrom. 2010;24:2745–52.

    Article  CAS  PubMed  Google Scholar 

  • Holčapek M, Dvořáková H, Lísa M, Girón AJ, Sandra P, Cvačka J. Regioisomeric analysis of triacylglycerols using silver-ion liquid chromatography-atmospheric pressure chemical ionization mass spectrometry: Comparison of five different mass analyzers. J Chromatogr A. 2010;1217:8186–94.

    Article  PubMed  Google Scholar 

  • Holčapek M, Velínská H, Lísa M, Česla P. Orthogonality of silver-ion and non-aqueous reversed-phase HPLC/MS in the analysis of complex natural mixtures of triacylglycerols. J Sep Sci. 2009;32:3672–80.

    Article  PubMed  Google Scholar 

  • Holčapek M, Jandera P, Zderadička P, Hrubá L. Characterization of triacylglycerol and diacylglycerol composition of plant oils using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. J Chromatogr A. 2003;1010:195–215.

    Article  PubMed  Google Scholar 

  • Janssen HG, Hrncirik K, Szoradi A, Leijten M. An improved method for sn-2 position analysis of triacylglycerols in edible oils and fats based on immobilised lipase D (Rhizopus delemar). J Chromatogr A. 2006;1112:141–7.

    Article  CAS  PubMed  Google Scholar 

  • Juaneda P, Sebedio JL, Christie WW. Complete separation of the geometrical-isomers of linolenic acid by high-performance liquid – Chromatography with a silver ion column. HRC – J High Res Chromatog. 1994;17:321–4.

    Article  CAS  Google Scholar 

  • Kasai PH, Mcleod D, Watanabe T. Acetylene and ethylene complexes of copper and silver atoms-matrix-isolation electron-spin-resonance study. J Am Chem Soc. 1980;102:179–90.

    Article  CAS  Google Scholar 

  • Leskinen HM. Quantification of triacylglycerol regioisomers by ultra-high-performance liquid chromatography and ammonia negative ion atmospheric pressure chemical ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2010;24:1–5.

    Article  CAS  PubMed  Google Scholar 

  • Leskinen H, Suomela JP, Kallio H. Quantification of triacylglycerol regioisomers in oils and fat using different mass spectrometric and liquid chromatographic methods. Rapid Commun Mass Spectrom. 2007;21:2361–73.

    Article  CAS  PubMed  Google Scholar 

  • Leskinen H, Suomela JP, Pinta J, Kallio H. Regioisomeric structure determination of alpha- and beta-linolenoyldilinoleoylglycerol in blackcurrant seed oil by silver ion high-performance liquid chromatography and mass spectrometry. Anal Chem. 2008;80:5788–93.

    Article  CAS  PubMed  Google Scholar 

  • Lísa M, Denev R, Holčapek M. Retention Behavior of Isomeric Triacylglycerols in Silver-ion HPLC: Effects of Mobile Phase Composition and Separation Temperature. J Sep Sci. 2013;36:2888–900.

    Article  PubMed  Google Scholar 

  • Lísa M, Velínská H, Holčapek M. Regioisomeric characterization of triacylglycerols using silver-ion HPLC/MS and randomization synthesis of standards. Anal Chem. 2009;81:3903–10.

    Article  PubMed  Google Scholar 

  • Momchilova S, Nikolova-Damyanova B. Stationary phases for silver ion chromatography of lipids: Preparation and properties. J Sep Sci. 2003;26:261–70.

    Article  CAS  Google Scholar 

  • Momchilova S, Itabashi Y, Nikolova-Damyanova B, Kuksis A. Regioselective separation of isomeric triacylglycerols by reversed-phase high-performance liquid chromatography: Stationary phase and mobile phase effects. J Sep Sci. 2006;29:2578–83.

    Article  CAS  PubMed  Google Scholar 

  • Mottram HR, Woodbury SE, Evershed RP. Identification of triacylglycerol positional isomers present in vegetable oils by high performance liquid chromatography atmospheric pressure chemical ionization mass spectrometry. Rapid Commun Mass Spectrom. 1997;11:1240–52.

    Article  CAS  Google Scholar 

  • Neff WE, Adlof RO, Elagaimy M. Silver ion high-performance liquid chromatography of the triacylglycerols of crepis-alpina seed oil. J Am Oil Chem Soc. 1994;71:853–5.

    Article  CAS  Google Scholar 

  • Nikolova-Damyanova B. Retention of lipids in silver ion high-performance liquid chromatography: Facts and assumptions. J Chromatogr A. 2009;1216:1815–24.

    Article  CAS  PubMed  Google Scholar 

  • Nikolova-Damyanova B, Herslof BG, Christie WW. Silver ion high-performance liquid chromatography of derivatives of isomeric fatty acids. J Chromatogr. 1992;609:133–40.

    Article  CAS  Google Scholar 

  • Nikolova-Damyanova B, Christie WW, Herslof B. Silver ion high-performance liquid-chromatography of esters of isomeric octadecenoic fatty acids with short-chain monounsaturated alcohols. J Chromatogr A. 1995;693:235–9.

    Article  CAS  Google Scholar 

  • Schuyl PJW, De Joode T, Vasconcellos MA, Duchateau G. Silver-phase high-performance liquid chromatography electrospray mass spectrometry of triacylglycerols. J Chromatogr A. 1998;810:53–61.

    Article  CAS  Google Scholar 

  • Standal IB, Axelson DE, Aursand M. Differentiation of fish oils according to species by C-13-NMR regiospecific analyses of triacylglycerols. J Am Oil Chem Soc. 2009;86:401–7.

    Article  CAS  Google Scholar 

  • Van Der Klift EJC, Vivó-Truyols G, Claassen FW, Van Holthoon FL, Van Beek TA. Comprehensive two-dimensional liquid chromatography with ultraviolet, evaporative light scattering and mass spectrometric detection of triacylglycerols in corn oil. J Chromatogr A. 2008;1178:43–55.

    Article  CAS  PubMed  Google Scholar 

  • Vrkoslav V, Urbanová K, Háková M, Cvačka J. Analysis of wax esters by silver-ion high-performance liquid chromatography–tandem mass spectrometry. J Chromatogr A. 2013;1302:105–10.

    Article  CAS  PubMed  Google Scholar 

  • Winstein S, Lucas HJ. The coordination of silver ion with unsaturated compounds. J Am Chem Soc. 1938;60:836–47.

    Article  CAS  Google Scholar 

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Correspondence to Michal Holčapek .

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Holčapek, M., Lísa, M. (2016). Silver-Ion Chromatography of Glycerolipids. In: Wenk, M. (eds) Encyclopedia of Lipidomics. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7864-1_74-1

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  • DOI: https://doi.org/10.1007/978-94-007-7864-1_74-1

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