Skip to main content
SpringerLink
Log in

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

  • Published:
Food Analytical Methods Aims and scope Submit manuscript

Abstract

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.

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
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  • Glass RL, Krick TP, Eckhardt AE (1974) New series of fatty acids in Northern Pike (Esox lucius). Lipids 9:1004–1008

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • 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 630–631

  • 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 29:539–550

    Article  CAS  Google Scholar 

  • Guth H, Grosch W (1991) Detection of furanoid fatty acids in soya-bean oil—cause for light-induced off-flavor. Fett Wiss Technol 93:249–255

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Hammann S, Wendlinger C, Vetter W (2015) Analysis of intact cholesteryl esters of furan fatty acids in cod liver. Lipids 50:611–620

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

    Article  CAS  Google Scholar 

  • Ishii K, Okajima H, Koyamatsu T, Okada Y, Watanabe H (1988a) The composition of furan fatty acids in the crayfish. Lipids 23:694–700

    Article  CAS  Google Scholar 

  • Ishii K, Okajima H, Okada Y, Watanabe H (1988b) Studies on furan fatty acids of salmon roe phospholipids. J Biochem 103:836–839

    CAS  Google Scholar 

  • 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–E3457

    Article  CAS  Google Scholar 

  • 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 67:858–862

    Article  CAS  Google Scholar 

  • Okada Y, Kaneko M, Okajima H (1996) Hydroxyl radical scavenging activity of naturally occurring furan fatty acids. Biol Pharm Bull 19:1607–1610

    Article  CAS  Google Scholar 

  • Ota T, Takagi T (1983) Furan fatty acids in the lipids of kokanee, Oncorhynchus nerka f. adonis. Bull Fac Fish Hokkaido Univ 34:88–92

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • 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 61:3969–3977

    Article  CAS  Google Scholar 

  • 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 9:283–297

    Article  CAS  Google Scholar 

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

  • Scrimgeour CM (1977) Quantitative analysis of furanoid fatty acids in crude and refined cod liver oil. J Am Oil Chem Soc 54:210–211

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • 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 89:1501–1508

    CAS  Google Scholar 

  • 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 17:308–311

    Article  CAS  Google Scholar 

  • 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 1–5:5

    Google Scholar 

  • Wendlinger C, Vetter W (2014) High concentrations of furan fatty acids in organic butter samples from the German market. J Agric Food Chem 62:8740–8744

    Article  CAS  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

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

    Christine Wendlinger, Simon Hammann & Walter Vetter

Authors
  1. Christine Wendlinger
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Simon Hammann
    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.

ESM 1

(DOCX 91 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wendlinger, C., Hammann, S. & Vetter, W. Detailed Study of Furan Fatty Acids in Total Lipids and the Cholesteryl Ester Fraction of Fish Liver. Food Anal. Methods 9, 459–468 (2016). https://doi.org/10.1007/s12161-015-0211-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12161-015-0211-x

Keywords

Search

Navigation