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

Hammann, Simon; Wendlinger, Christine; Vetter, Walter

doi:10.1007/s11745-015-4019-7

Cited by 25 publications

(31 citation statements)

References 30 publications

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“…We analyzed livers of sea bass (Dicentrarchus labrax) wild caught in France as well as from aquaculture in Greece and France, goatfish (Mullus barbatus) from France, meagre (Argyrosomus regius) from Corsica, and gilthead (Dentex maroccanus) from New Zealand. Additionally, individual cod livers (Gadus morhua) from four cans (marketed for human consumption) from different brands were purchased from supermarkets in Stuttgart, Germany, in April 2014 (Hammann et al 2015). According to the label, the cod samples were all caught in the North-East Atlantic Ocean near Iceland.…”

Section: Samplesmentioning

confidence: 99%

“…Helium (purity 5.0) was from WestfalenGas (Münster, Germany). Pentadecanoic acid cholesteryl ester (15:0-CE) which was used as recovery standard for the solid-phase extraction was prepared according to Hammann et al (2015). The preparation of the internal standard 10,13-epoxy-11-methyloctadeca-10, 12-dienoic acid ethyl ester (9M5-EE) was according to Vetter et al (2012).…”

Section: Chemicals and Standardsmentioning

confidence: 99%

“…column fitted with a frit) was performed according to Hammann et al (2015) with modifications. In brief, the column was conditioned with 50 mL n-hexane, and the liver extracts (∼120 mg crude extract in 0.5 mL of n-hexane), supplemented with 39 μg of the internal standard 15:0-CE, were eluted into three fractions.…”

Section: Solid-phase Column Chromatography For the Separation Of Lipidsmentioning

confidence: 99%

“…F-acids have frequently been reported in the lipids of fish (Glass et al 1974;Gunstone et al 1978;Wahl et al 1994;Pacetti et al 2010), plants (Hannemann et al 1989), in oils (Boselli et al 2000;Guth and Grosch 1991), and butter (Guth and Grosch 1992), with fish being the richest nutritional source (Wendlinger and Vetter 2014). Unlike the usually low contribution to food lipids, F-acids were reported to be major fatty acids in the cholesteryl ester fraction of fish liver (Glass et al 1974(Glass et al , 1977Hammann et al 2015).…”

Section: Introductionmentioning

confidence: 99%

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

2015

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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 Facids, including several new or scarcely detected homologues, were detected in the samples. The concentrations of total Facids 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.

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Section: Samplesmentioning

confidence: 99%

Section: Chemicals and Standardsmentioning

confidence: 99%

Section: Solid-phase Column Chromatography For the Separation Of Lipidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

2015

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“…Several furan fatty acids have been isolated as secondary metabolites from various organisms, including plants (Kimura et al, 2010), fungi (Ma et al, 2016) and fish (Hammann et al, 2015). They have displayed various biological activities, such as antioxidative (Teixeira et al, 2013) and anti-inflammatory (Wakimoto et al, 2011) prop-erties.…”

Section: Discussionmentioning

confidence: 99%

Mumiamicin: Structure and bioactivity of a new furan fatty acid from <i>Mumia</i> sp. YSP-2-79

Kimura

Tajima

Inahashi

et al. 2018

J. Gen. Appl. Microbiol.

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Heart‐Cut Two‐Dimensional Countercurrent Chromatography for the Isolation of a Furan Fatty Acid Triacylglycerol from Latex Gloves and Identification of Further Lipid Compounds

Wiedmaier‐Czerny

Müller

Vetter

2020

J Americ Oil Chem Soc

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Hevea brasiliensis latex from specific genotypes such as RRIM501 or PB235 is one of the richest natural sources of furan fatty acid 9-(3-methyl-5-pentylfuran-2-yl)nonanoic acid (9M5), which is mainly present in the form of triacylglycerols. In this study, we successfully isolated a triacylglycerol esterified with three 9M5 molecules (tri-9M5) with a purity of 97% from the lipid extract of latex gloves by means of countercurrent chromatography (CCC). The gas chromatography with a mass spectrometry (GC/MS) spectrum of tri-9M5 not only featured the diagnostic fragment ion [M-RCOO] + of triacylglycerols but also a fragment ion shifted by 16 Da to higher mass which corresponded with [M-RCO] + . [M-RCO] + was only detected in triacylglycerols substituted with at least one furan fatty acid. Additionally, five γ-tocotrienyl fatty acid esters (γ-T 3 -FA esters), namely, γ-T 3 -16:0, γ-T 3 -18:0, γ-T 3 -18:1n-9, γ-T 3 -18:2n-6 and γ-T 3 -20:0, were detected in the sample. Contributions of γ-T 3 -FA esters with 18:1n-9 and 18:2n-6 which co-eluted in GC/MS could be calculated after mathematical correction for contributions of the 13 C 2 isotope peak of γ-T 3 -18:2n-6 to γ-T 3 -18:1n-9. This was necessary for quantitation of these two γ-T 3 -FA esters. Improved separation of the γ-T 3 -FA esters could be achieved by the novel heart-cut recycling CCC mode (four cycles). Sterols detected in disposable latex gloves were β-sitosterol, Δ 5avenasterol, and stigmasterol along with small quantities of 24-methylene-cycloartenol and Δ 5 -citrostadienol.Keywords Triacylglycerol Á Countercurrent chromatography Á Hevea brasiliensis latex Á 9M5 Á Furan fatty acid Á Tocotrienyl fatty acid ester J Am Oil Chem Soc (2020) 97: 463-474. Fig. 1 (a) General structure of a triacylglycerol with R 1 , R 2 , and R 3 being acyl moieties and structure of (b) the characteristic GC/MS fragment ion [M-RCOO] + of triacylglycerols, (c) the [M-RCO] + fragment ion additionally found only in the presence of at least one furan fatty acid, and (d) the furan fatty acid 9M5. R 1,2,3 = fatty acid residue (one or more furan fatty acids). The structure with R 1, R 2, R 3 = 9M5 corresponds with tri-9M5 464J Am Oil Chem Soc J Am Oil Chem Soc (2020) 97: 463-474

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

Cited by 25 publications

References 30 publications

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

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

Mumiamicin: Structure and bioactivity of a new furan fatty acid from <i>Mumia</i> sp. YSP-2-79

Heart‐Cut Two‐Dimensional Countercurrent Chromatography for the Isolation of a Furan Fatty Acid Triacylglycerol from Latex Gloves and Identification of Further Lipid Compounds

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