Skip to main content
SpringerLink
Log in

Analysis of Intact Cholesteryl Esters of Furan Fatty Acids in Cod Liver

  • Methods
  • Published:
Lipids

Abstract

Furan fatty acids (F-acids) are a class of natural antioxidants with a furan moiety in the acyl chain. These minor fatty acids have been reported to occur with high proportions in the cholesteryl ester fraction of fish livers. Here we present a method for the direct analysis of intact cholesteryl esters with F-acids and other fatty acids in cod liver lipids. For this purpose, the cholesteryl ester fraction was isolated by solid phase extraction (SPE) and subsequently analyzed by gas chromatography with mass spectrometry (GC/MS) using a cool-on-column inlet. Pentadecanoic acid esterified with cholesterol was used as an internal standard. GC/MS spectra of F-acid cholesteryl esters featured the molecular ion along with characteristic fragment ions for both the cholesterol and the F-acid moiety. All investigated cod liver samples (n = 8) showed cholesteryl esters of F-acids and, to a lower degree, of conventional fatty acids. By means of GC/MS-SIM up to ten F-acid cholesteryl esters could be determined in the samples. The concentrations of cholesteryl esters with conventional fatty acids amounted to 78–140 mg/100 g lipids (mean 97 mg/100 g lipids), while F-acid cholesteryl esters were present at 47–270 mg/100 g lipids (mean 130 mg/100 g lipids).

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Abbreviations

7D5:

7-(3,4-Dimethyl-5-pentylfuran-2-yl)-heptanoic acid

9D3:

9-(3,4-Dimethyl-5-propylfuran-2-yl)-nonanoic acid

9D5:

9-(3,4-Dimethyl-5-pentylfuran-2-yl)-nonanoic acid

9M5:

9-(3-Methyl-5-pentylfuran-2-yl)-nonanoic acid

11D3:

11-(3,4-Dimethyl-5-propylfuran-2-yl)-undecanoic acid

11D5:

11-(3,4-Dimethyl-5-pentylfuran-2-yl)-undecanoic acid

11M3:

11-(3-Methyl-5-propylfuran-2-yl)-undecanoic acid

11M5:

11-(3-Methyl-5-pentylfuran-2-yl)-undecanoic acid

13D3:

13-(3,4-Dimethyl-5-propylfuran-2-yl)-tridecanoic acid

13D5:

13-(3,4-Dimethyl-5-pentylfuran-2-yl)-tridecanoic acid

CE:

Cholesteryl ester

DHA:

Docosahexaenoic acid (22:6n-3)

EPA:

Eicosapentaenoic acid (20:5n-3)

F-acid:

Furan fatty acid

F-CE:

Furan fatty acid cholesteryl ester

FAME:

Fatty acid methyl ester

GC/MS:

Gas chromatography with mass spectrometry

HPLC:

High performance liquid chromatography

NMR:

Nuclear magnetic resonance

PUFA:

Polyunsaturated fatty acid

SIM:

Selected ion monitoring

SPE:

Solid phase extraction

TIC:

Total ion current

References

  1. Spiteller G (2005) Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet? Lipids 40(8):755–771

    Article  CAS  PubMed  Google Scholar 

  2. Vetter W, Laure S, Wendlinger C, Mattes A, Smith AWT, Knight DW (2012) Determination of furan fatty acids in food samples. J Am Oil Chem Soc 89(8):1501–1508

    CAS  Google Scholar 

  3. Pacetti D, Mozzon M, Lucci P, Frega NG (2013) Bioactive fish fatty acids: Health effects and their use as functional food ingredients. Curr Nutr Food Sci 9(4):283–297

    Article  CAS  Google Scholar 

  4. Vetter W, Wendlinger C (2013) Furan fatty acids—valuable minor fatty acids in food. Lipid Technol 25(1):7–10

    Article  CAS  Google Scholar 

  5. Glass RL, Krick TP, Eckhardt AE (1974) New series of fatty acids in northern pike (Esox lucius). Lipids 9(12):1004–1008

    Article  CAS  PubMed  Google Scholar 

  6. Gunstone FD, Wijesundera RC (1978) The component acids of the lipids in four commercial fish meals. J Sci Food Agric 29(1):28–32

    Article  CAS  PubMed  Google Scholar 

  7. Hannemann K, Puchta V, Simon E, Ziegler H, Ziegler G, Spiteller G (1989) The common occurrence of furan fatty acids in plants. Lipids 24(4):296–298

    Article  CAS  PubMed  Google Scholar 

  8. Guth H, Grosch W (1992) Furan fatty acids in butter and butter oil. Z Lebensm Unters Forsch 194(4):360–362

    Article  CAS  Google Scholar 

  9. Pacetti D, Alberti F, Boselli E, Frega NG (2010) Characterisation of furan fatty acids in Adriatic fish. Food Chem 122(1):209–215

    Article  CAS  Google Scholar 

  10. Boselli E, Grob K, Lercker G (2000) Determination of furan fatty acids in extra virgin olive oil. J Agric Food Chem 48(7):2868–2873

    Article  CAS  PubMed  Google Scholar 

  11. Glass RL, Krick TP, Olson DL, Thorson RL (1977) The occurrence and distribution of furan fatty acids in spawning male freshwater fish. Lipids 12(10):828–836

    Article  CAS  PubMed  Google Scholar 

  12. Schoedel R, Spiteller G (1987) On the occurrence of F-acids in cattle liver and their enzymic degradation during tissue damage. Liebigs Ann Chem 5:459–462

    Article  Google Scholar 

  13. Kamm W, Dionisi F, Fay L, Hischenhuber C, Schmarr H-G, Engel K-H (2001) Analysis of steryl esters in cocoa butter by on-line liquid chromatography–gas chromatography. J Chromatogr A 918(2):341–349

    Article  CAS  PubMed  Google Scholar 

  14. Evershed RP, Male VL, Goad LJ (1987) Strategy for the analysis of steryl esters from plant and animal tissues. J Chromatogr 400:187–205

    Article  CAS  PubMed  Google Scholar 

  15. Esche R, Barnsteiner A, Scholz B, Engel K-H (2012) Simultaneous analysis of free phytosterols/phytostanols and intact phytosteryl/phytostanyl fatty acid and phenolic acid esters in cereals. J Agric Food Chem 60(21):5330–5339

    Article  CAS  PubMed  Google Scholar 

  16. Verleyen T, Forcades M, Verhe R, Dewettinck K, Huyghebaert A, De Greyt W (2002) Analysis of free and esterified sterols in vegetable oils. J Am Oil Chem Soc 79(2):117–122

    Article  CAS  Google Scholar 

  17. Esche R, Carcelli A, Barnsteiner A, Sforza S, Engel K-H (2013) Analysis of phytosteryl and phytostanyl fatty acid esters in enriched dairy foods: a combination of acid digestion, lipid extraction, and on-line LC-GC. Eur Food Res Technol 236(6):999–1007

    Article  CAS  Google Scholar 

  18. Glass RL, Krick TP, Sand DM, Rahn CH, Schlenk H (1975) Furanoid fatty acids from fish lipids. Lipids 10(11):695–702

    Article  CAS  PubMed  Google Scholar 

  19. Rahn CH, Sand DM, Krick TP, Glass RL, Schlenk H (1981) Syntheses of radioactive furan fatty acids. Lipids 16(5):360–364

    Article  CAS  Google Scholar 

  20. Lusby WR, Thompson MJ, Kochansky J (1984) Analysis of sterol esters by capillary gas chromatography-electron impact and chemical ionization-mass spectrometry. Lipids 19(11):888–901

    Article  CAS  Google Scholar 

  21. Bauer ST (1946) The preparation of fatty acid chlorides. Oil Soap 23(1):1–5

    Article  CAS  Google Scholar 

  22. Gunstone FD, Wijesundera RC, Scrimgeour CM (1978) The component acids of lipids from marine and freshwater species with special reference to furan-containing acids. J Sci Food Agric 29(6):539–550

    Article  CAS  Google Scholar 

  23. Evershed RP, Prescott MC, Spooner N, Goad LJ (1989) Negative ion ammonia chemical ionization and electron impact ionization mass spectrometric analysis of steryl fatty acyl esters. Steroids 53(3–5):285–309

    Article  CAS  PubMed  Google Scholar 

  24. Brown AJ, Jessup W (1999) Oxysterols and atherosclerosis. Atherosclerosis 142(1):1–28

    Article  CAS  PubMed  Google Scholar 

  25. Brown AJ, Dean RT, Jessup W (1996) Free and esterified oxysterol: formation during copper-oxidation of low density lipoprotein and uptake by macrophages. J Lipid Res 37(2):320–335

    CAS  PubMed  Google Scholar 

  26. Brown AJ, Leong SL, Dean RT, Jessup W (1997) 7-Hydroperoxycholesterol and its products in oxidized low density lipoprotein and human atherosclerotic plaque. J Lipid Res 38(9):1730–1745

    CAS  PubMed  Google Scholar 

  27. Rezanka T (1992) Analysis of sterol esters from alga and yeast by high-performance liquid chromatography and capillary gas chromatography-mass spectrometry with chemical ionization. J Chromatogr 598(2):219–226

    Article  CAS  PubMed  Google Scholar 

  28. Kuksis A, Myher JJ, Marai L, Little JA, McArthur RG, Roncari DAK (1986) Fatty acid composition of individual plasma steryl esters in phytosterolemia and xanthomatosis. Lipids 21(6):371–377

    Article  CAS  PubMed  Google Scholar 

  29. Smith NB (1982) Hydrogenation of cholesteryl esters during gas chromatography on a polar fused-silica capillary column. J Chromatogr 249(1):57–63

    Article  CAS  Google Scholar 

  30. The AOCS Lipid Library. http://lipidlibrary.aocs.org/

Download references

Acknowledgments

We gratefully acknowledge the financial support of the Fonds der Chemischen Industrie in the form of a stipend grant to S.H.

Author information

Authors and Affiliations

  1. Institute of Food Chemistry (170b), University of Hohenheim, Garbenstraße 28, 70599, Stuttgart, Germany

    Simon Hammann, Christine Wendlinger & Walter Vetter

Authors
  1. Simon Hammann
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Christine Wendlinger
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Walter Vetter
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Walter Vetter.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 173 kb)

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hammann, S., Wendlinger, C. & Vetter, W. Analysis of Intact Cholesteryl Esters of Furan Fatty Acids in Cod Liver. Lipids 50, 611–620 (2015). https://doi.org/10.1007/s11745-015-4019-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-015-4019-7

Keywords

Search

Navigation