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Regioisomers of octanoic acid-containing structured triacylglycerols analyzed by tandem mass spectrometry using ammonia negative ion chemical ionization

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Lipids

Abstract

Tandem mass spectrometry based on ammonia negative ion chemical ionization and sample introduction via direct exposure probe was applied to analysis of regioisomeric structures of octanoic acid containing structured triacylglycerols (TAG) of type MML, MLM, MLL, and LML (M, medium-chain fatty acid; L, long-chain fatty acid). Collision-induced dissociation of deprotonated parent TAG with argon was used to produce daughter ion spectra with appropriate fragmentation patterns for structure determination. Fatty acids constituting the TAG molecule were identified according to [RCO2]− ions in the daughter ion spectra. With the standard curve for ratios of [M-H-RCO2H-100]− ions corresponding to each [RCO2]− ion, determined with known mixtures of sn-1/3 and sn-2 regioisomers of structured TAG, it was possible to determine the proportions of different regioisomers in unknown samples. The method enabled quantification of MML- and MLM-type structured TAG. In the case of MLL- and LML-type TAG, it was possible to determine the most abundant regioisomer in the unknown mixture and estimate the proportions of regioisomers when there were more than 50% MLL-type isomers in the mixture.

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Abbreviations

ACN:

acyl carbon number

ESI:

electrospray ionization

FAB:

fast atom bombardment

GC:

gas chromatography

HPLC:

high-performance liquid chromatography

M:

medium-chain fatty acid

L:

long-chain fatty acid

TAG:

triacylglycerol

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Authors and Affiliations

  1. Department of Biochemistry and Food Chemistry, University of Turku, FIN-20014, Turku, Finland

    J. -P. Kurvinen & H. Kallio

  2. Department of Biochemistry and Nutrition, Technical University of Denmark, DK-2800, Lyngby, Denmark

    H. Mu & C. E. Høy

  3. Department of Biotechnology, Technical University of Denmark, DK-2800, Lyngby, Denmark

    X. Xu

Authors
  1. J. -P. Kurvinen
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  2. H. Mu
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  3. H. Kallio
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  4. X. Xu
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  5. C. E. Høy
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Correspondence to H. Kallio.

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Kurvinen, J.P., Mu, H., Kallio, H. et al. Regioisomers of octanoic acid-containing structured triacylglycerols analyzed by tandem mass spectrometry using ammonia negative ion chemical ionization. Lipids 36, 1377–1382 (2001). https://doi.org/10.1007/s11745-001-0855-9

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  • DOI: https://doi.org/10.1007/s11745-001-0855-9

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