Food Analytical Methods

, Volume 9, Issue 2, pp 459–468 | Cite as

Detailed Study of Furan Fatty Acids in Total Lipids and the Cholesteryl Ester Fraction of Fish Liver

  • Christine Wendlinger
  • Simon Hammann
  • Walter VetterEmail author


Furan fatty acids (F-acids) are valuable, bioactive minor components in lipids which are characterized by a furan moiety in the acyl chain. Here, we present a gas chromatography/mass spectrometry method operated in the selected ion monitoring mode (GC/MS-SIM) for the thorough determination of F-acid as methyl esters in fish. The method takes advantage of the molecular ion and two characteristic fragment ions and enables the unequivocal detection of >350 saturated, mono- and dienoic F-acids in four GC/MS-SIM runs. This method was applied to the analysis of the methyl esters obtained from the triacylglyceride (TG) and the cholesteryl ester (CE) fraction of ten individual fish liver samples. Up to 23 F-acids, including several new or scarcely detected homologues, were detected in the samples. The concentrations of total F-acids ranged from 25 to 280 mg/100 g lipids in the TG fractions and <0.11 to 115 mg/100 g lipids in the CE fractions.


Furan fatty acids Fish liver Gas chromatography Mass spectrometry Selected ion monitoring 


Conflict of Interest

Simon Hammann has received a stipend grant from the Fonds der Chemischen Industry. Christine Wendlinger, Simon Hammann, and Walter Vetter declare that they have no conflict of interest. This article does not contain any studies with human or animal subjects.

Supplementary material

12161_2015_211_MOESM1_ESM.docx (91 kb)
ESM 1 (DOCX 91 kb)


  1. Boselli E, Grob K, Lercker G (2000) Determination of furan fatty acids in extra virgin olive oil. J Agric Food Chem 48:2868–2873CrossRefGoogle Scholar
  2. Glass RL, Krick TP, Eckhardt AE (1974) New series of fatty acids in Northern Pike (Esox lucius). Lipids 9:1004–1008CrossRefGoogle Scholar
  3. Glass RL, Krick TP, Sand DM, Rahn CH, Schlenk H (1975) Furanoid fatty acids from fish lipids. Lipids 10:695–702CrossRefGoogle Scholar
  4. Glass RL, Krick TP, Olson DL, Thorson RL (1977) The occurrence and distribution of furan fatty acids in spawning male freshwater fish. Lipids 12:828–836CrossRefGoogle Scholar
  5. Gunstone FD, Wijesundera RC, Love RM, Ross D (1976) Relative enrichment of furan-containing fatty acids in the liver of starving cod. J Chem Soc Chem Commun 630–631Google Scholar
  6. 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 29:539–550CrossRefGoogle Scholar
  7. Guth H, Grosch W (1991) Detection of furanoid fatty acids in soya-bean oil—cause for light-induced off-flavor. Fett Wiss Technol 93:249–255Google Scholar
  8. Guth H, Grosch W (1992) Furan fatty acids in butter and butter oil. Z Lebensm Unters Forsch 194:360–362CrossRefGoogle Scholar
  9. Hammann S, Wendlinger C, Vetter W (2015) Analysis of intact cholesteryl esters of furan fatty acids in cod liver. Lipids 50:611–620Google Scholar
  10. Hannemann K, Puchta V, Simon E, Ziegler H, Ziegler G, Spiteller G (1989) The common occurrence of furan fatty acids in plants. Lipids 24:296–298CrossRefGoogle Scholar
  11. Ishii K, Okajima H, Koyamatsu T, Okada Y, Watanabe H (1988a) The composition of furan fatty acids in the crayfish. Lipids 23:694–700CrossRefGoogle Scholar
  12. Ishii K, Okajima H, Okada Y, Watanabe H (1988b) Studies on furan fatty acids of salmon roe phospholipids. J Biochem 103:836–839Google Scholar
  13. Lemke RAS, Peterson AC, Ziegelhoffer EC, Westphall MS, Tjellström H, Coon JJ, Donohue TJ (2014) Synthesis and scavenging role of furan fatty acids. Proc Natl Acad Sci U S A 111:E3450–E3457CrossRefGoogle Scholar
  14. Okada Y, Okajima H, Konishi H, Terauchi M, Ishii K, Liu I, Watanabe H (1990) Antioxidant effect of naturally occurring furan fatty acids on oxidation of linoleic acid in aqueous dispersion. J Am Oil Chem Soc 67:858–862CrossRefGoogle Scholar
  15. Okada Y, Kaneko M, Okajima H (1996) Hydroxyl radical scavenging activity of naturally occurring furan fatty acids. Biol Pharm Bull 19:1607–1610CrossRefGoogle Scholar
  16. Ota T, Takagi T (1983) Furan fatty acids in the lipids of kokanee, Oncorhynchus nerka f. adonis. Bull Fac Fish Hokkaido Univ 34:88–92Google Scholar
  17. Pacetti D, Alberti F, Boselli E, Frega NG (2010) Characterisation of furan fatty acids in Adriatic fish. Food Chem 122:209–215CrossRefGoogle Scholar
  18. Pacetti D, Balzano M, Colella S, Santojanni A, Frega NG (2013a) Effect of spawning on furan fatty acid profile of edible muscle and organ tissues from sardine (Sardina pilchardus) and anchovy (Engraulis encrasicolus). J Agric Food Chem 61:3969–3977CrossRefGoogle Scholar
  19. Pacetti D, Mozzon M, Lucci P, Frega NG (2013b) Bioactive fish fatty acids: health effects and their use as functional food ingredients. Curr Nutr Food Sci 9:283–297CrossRefGoogle Scholar
  20. Schoedel R, Spiteller G (1987) On the occurrence of F-acids in cattle liver and their enzymic degradation during tissue damage. Liebigs Ann Chem 459–462Google Scholar
  21. Scrimgeour CM (1977) Quantitative analysis of furanoid fatty acids in crude and refined cod liver oil. J Am Oil Chem Soc 54:210–211CrossRefGoogle Scholar
  22. Spiteller G (2005) Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet? Lipids 40:755–771CrossRefGoogle Scholar
  23. Vetter W, Wendlinger C (2013) Furan fatty acids—valuable minor fatty acids in food. Lipid Technol 25:7–10CrossRefGoogle Scholar
  24. 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 89:1501–1508Google Scholar
  25. Wahl HG, Liebich HM, Hoffmann A (1994) Identification of fatty acid methyl esters as minor components of fish oil by multidimensional GC-MSD: new furan fatty acids. J High Resolut Chromatogr 17:308–311CrossRefGoogle Scholar
  26. Wakimoto T, Kondo H, Nii H, Kimura K, Egami Y, Oka Y, Yoshida M, Kida E, Ye Y, Akahoshi S, Asakawa T, Matsumura K, Ishida H, Nukaya H, Tsuji K, Kan T, Abe I (2011) Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus. Proc Natl Acad Sci USA, Early Ed 1–5:5Google Scholar
  27. Wendlinger C, Vetter W (2014) High concentrations of furan fatty acids in organic butter samples from the German market. J Agric Food Chem 62:8740–8744CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Christine Wendlinger
    • 1
  • Simon Hammann
    • 1
  • Walter Vetter
    • 1
    Email author
  1. 1.Institute of Food Chemistry (170b)University of HohenheimStuttgartGermany

Personalised recommendations