Skip to main content
SpringerLink
Log in

Identification of natural diacylglycerols as the 3,5-dinitrophenylurethanes by chiral phase liquid chromatography with mass spectrometry

  • Method
  • Published:
Lipids

Abstract

This study reports a facile identification of the molecular species of enantiomeric diacylglycerols by combining chiral phase high-performance liquid chromatography with positive chemical ionization mass spectrometry. For this purpose the 3,5-dinitrophenylurethane (DNPU) derivatives ofsn-1,2(2,3)-diacylglycerols are separated on an (R+)-naphthylethylamine polymer column (25 cm × 0.46 cm ID) using an isocratic solvent system made up of hexane/dichloroethane/acetonitrile (85∶10∶5, by vol) or isooctane/tert-butyl methyl ether/acetonitrile/isopropanol (80∶10∶5∶5, by vol). About 1% of the column effluent (1 mL/min) was admitted to a quadrupole mass spectrometer (Hewlett-Packard, Palo Alto, CA)via direct liquid inlet interface, and positive chemical ionization spectra were recorded over the range of 200–900 mass units. The DNPU derivatives of diacylglycerols yield characteristic [M-DNPU]+ and [RCO+74]+ ions for each diacylglycerol species from which the molecular weight and exact pairing of fatty acids can be unequivocally obtained. The characteristic ions appear to be generated in nearly correct mass proportions as indicated by preliminary quantitative comparisons.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

CIMS:

chemical ionization mass spectrometry

DNPU:

dinitrophenylurethanes

GLC:

gas-liquid chromatography

HPLC:

high-performance liquid chromatography

LC/MS:

liquid chromatography/mass spectrometry

TLC:

thin-layer chromatography

References

  1. Takagi, T., and Itabashi, Y. (1987)Lipids 22, 596–600.

    Article  PubMed  CAS  Google Scholar 

  2. Itabashi, Y., Kuksis, A., and Myher, J.J. (1990)J. Lipid Res. 31, 2119–2126.

    PubMed  CAS  Google Scholar 

  3. Kuksis, A., Marai, L., Myher, J.J., and Itabashi, Y. (1989) inProceedings, 15th Scandinavian Symposium on Lipids (Shukla, V.K.S. and Hølmer, G., eds.), pp. 336–370, Rebild Bakker, Skorping, Denmark.

    Google Scholar 

  4. Itabashi, Y., Marai, L., and Kuksis, A. (1989)J. Am. Oil Chem. Soc. 66, 491.

    Google Scholar 

  5. Kuksis, A., Marai, L., Myher, J.J. (1973)J. Am. Oil Chem. Soc. 50, 193–201.

    PubMed  CAS  Google Scholar 

  6. Myher, J.J., Kuksis, A., Marai, L., and Sandra, P. (1988)J. Chromatogr. 452, 93–118.

    Article  PubMed  CAS  Google Scholar 

  7. Myher, J.J., and Kuksis, A. (1982)Can. J. Biochem. Cell Biol. 60, 638–650.

    CAS  Google Scholar 

  8. Itabashi, Y., Kuksis, A., Marai, L., and Takagi, T. (1990)J. Lipid Res. 31, 1711–1717.

    PubMed  CAS  Google Scholar 

  9. Kuksis, A., Marai, L., and Myher, J.J. (1983)J. Chromatogr. 273, 43–66.

    PubMed  CAS  Google Scholar 

  10. Pind, S., Kuksis, A., Myher, J.J., and Marai, L. (1984)Can. J. Biochem. Cell Biol. 62, 301–309.

    Article  CAS  Google Scholar 

  11. Brockerhoff, H., and Yurkowski, M. (1966)J. Lipid Res. 7, 62–64.

    PubMed  CAS  Google Scholar 

  12. Breckenridge, W.C., and Kuksis, A. (1968)J. Lipid Res. 9, 388–393.

    PubMed  CAS  Google Scholar 

Download references

Author information

Author notes

  1. Y. Itabashi

    Present address: Department of Chemistry, Faculty of Fisheries, Hokkaido University, Hakodate, Japan

Authors and Affiliations

  1. Banting and Best Department of Medical Research, University of Toronto, C.H. Best Institute, 112 College Street, M5G 1L6, Toronto, Canada

    Y. Itabashi, L. Marai & A. Kuksis

Authors
  1. Y. Itabashi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. Marai
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Kuksis
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

The abbreviations 14∶0, 16∶1, 18∶2, etc. represent normal chain fatty acids of 14, 16, 18, etc. acyl carbons and 0, 1, 2, etc. double bonds, respectively; 16∶0–18∶1, etc. represent diacylglycerols containing 16∶0 and 18∶1 fatty acids of unspecified positional distribution;sn indicates stereospecific numbering of glycerol carbons;sn-1,2-diacylglycerols andsn-2,3-diacylglycerols are enantiomeric diacylglycerols of unspecified fatty acid composition;rac-1,2-diacylglycerols are racemic diacylglycerols representing equal amounts ofsn-1,2-andsn-2,3-enantiomers;sn-1,2(2,3)-diacylglycerols are a mixture ofsn-1,2-andsn-2,3-diacylglycerols of unspecified proportion of enantiomers and unspecified fatty acid compisition and positional distribution; X-1,3-diacylglycerols are diacylglycerols of unspecified fatty acid composition and reverse isomer content.

About this article

Cite this article

Itabashi, Y., Marai, L. & Kuksis, A. Identification of natural diacylglycerols as the 3,5-dinitrophenylurethanes by chiral phase liquid chromatography with mass spectrometry. Lipids 26, 951–956 (1991). https://doi.org/10.1007/BF02535983

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02535983

Keywords

Search

Navigation