Chlorinated fatty acids in membrane lipids of fish

Björn, Helena; Sundin, Peter; Wesén, Clas; Mu, Huiling; Martinsen, Kari; Kvernheim, Arne Lund; Skramstad, Jan; Odham, Göran

doi:10.1007/s001140050488

Cited by 14 publications

(12 citation statements)

References 16 publications

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“…5,8,15 -17 This metabolite is the shortest Cl 2 FA with an even-numbered carbon chain that has been found, indicating that furtheř -oxidation may be sterically hindered. 15 The Cl 2 FAs are bound both in membrane and in storage lipids 7,9,15,16 and the incorporation in membrane lipids may influence cellular functions. 18 -22 not been reported, but can be regarded as possible because a recent study showed that human cell lines can assimilate and metabolize 9,10-Cl 2 C 18 .…”

Section: Introductionmentioning

confidence: 99%

Structural characterization of 5,6‐dichlorotetradecanoic acid, an isolated metabolite of 9,10‐dichlorooctadecanoic acid, by studying picolinyl esters, pyrrolidides and methyl esters with electron ionization mass spectrometry

Åkesson-Nilsson

Wesén

2004

J. Mass Spectrom.

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A method is presented for identification of positional isomers of dichlorinated fatty acids, based on derivatization to picolinyl esters prior to gas chromatographic/mass spectrometric analysis in the electron ionization mode. The mass spectra of the picolinyl esters showed structure-specific fragmentation patterns. By using the picolinyl ester, 5,6-dichlorotetradecanoic acid was identified as a metabolite from a cell-culture medium obtained by culturing human cell lines in media supplemented with threo-9,10-dichlorooctadecanoic acid. This indicates that dichlorinated fatty acids are degraded by beta-oxidation. It is also possible to locate tentatively the position of chlorine atoms in 5,6-dichlorotetradecanoic acid as its methyl ester or pyrrolidide.

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Section: Introductionmentioning

confidence: 99%

Structural characterization of 5,6‐dichlorotetradecanoic acid, an isolated metabolite of 9,10‐dichlorooctadecanoic acid, by studying picolinyl esters, pyrrolidides and methyl esters with electron ionization mass spectrometry

Åkesson-Nilsson

Wesén

2004

J. Mass Spectrom.

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“…Chlorinated fatty acids are bound in lipids such as triacylglycerols and phospholipids (Wese´n 1995;Bjo¨rn et al 1998b), and thus, theoretically have a potency to disturb any biological process involving lipids. They have for instance been shown to have an impact on cell membrane functions (Ewald and Sundin 1993).…”

Section: Introductionmentioning

confidence: 99%

Metabolic fate of 14C-labelled chlorinated and non-chlorinated fatty acids in goldfish (Carassius auratus)

Björn

Ewald

Sundin

et al. 2004

Fish Physiol Biochem

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In order to study the metabolic fate of chlorinated fatty acids in fish, goldfish were fed either 9,10-dichlorostearic acid or oleic acid, chosen as the unchlorinated analogue, both radiolabelled at either the carboxyl (1st) or the terminal (18th) carbon of the fatty acid chain. By keeping the fish in hermetically closed aquaria, all the respired, assimilated and excreted radioactivity could be accounted for. Fish fed 9,10-dichlorostearic acid labelled in the terminal end respired radioactive CO 2 to a much lower degree than fish fed the other test compounds. As a consequence, the radioactivity bound in lipids was higher in the group of fish fed dichlorostearic acid labelled in the terminal end. It is suggested that the chlorine atoms in the middle of the carbon chain obstruct the metabolic turn-over of 9,10-dichlorostearic acid, which may have an impact on the residence time of these compounds in the ecosystem.

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“…Dichloromyristic acid is the predominating chlorinated fatty acid in fish containing low concentrations of extractable organically bound chlorine (Mu et al 1996a;Björn et al 1998b), and is also a major component of the organochlorine load in lobster digestive glands (Milley et al 1997) and in the liver of rats fed dichlorostearic acid (Conacher et al 1984). It has been suggested that dichloromyristic acid may accumulate in organisms because further b-oxidation is sterically hindered by the chlorine atoms (Conacher et al 1984;Ewald & Sundin 1993).…”

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confidence: 99%

“…phospholipids) (Ewald et al 1996;Björn et al 1998b;Vereskuns 1999). Actually, the concentration of chlorinated fatty acids was found to be higher in phospholipids than in triacylglycerols in muscle tissue of fish from Scandinavian waters (Björn et al 1998b). Likewise, a large proportion of the recovered radioactivity was associated with phospholipids in fish fed radiolabelled dichlorostearic acid (Ewald et al 1996).…”

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Removal of Xenobiotic Dichlorostearic Acid from Phospholipids and Neutral Lipids in Cultured Human Cell Lines by ß‐Oxidation and Secretion of Dichloromyristic Acid

Gustafson-Svärd

Åkesson-Nilsson

Mattsson

et al. 2001

Pharmacology & Toxicology

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Chlorinated fatty acids represent a recently discovered group of potentially hazardous organochlorine pollutants in the environment. The ability of human cells to incorporate and metabolise this type of fatty acids has never been investigated. The aim of the present study was, therefore, to investigate if two human cell lines, INT 407 and SH-SY5Y, incorporate and metabolise extracellular dichlorostearic acid. Cells were incubated with 9,10-dichlorostearic acid for 24 hr, and the amounts of chlorinated fatty acids in cells and culture medium analysed every two days for up to 6 or 10 days. Lipids were separated by solid phase extraction, transesterified to fatty acid methyl esters, and analysed by gas chromatography in combination with a halogen specific detector (GC/XSD). Dichlorostearic acid, dichloropalmitic acid and dichloromyristic acid were found in phospholipids and in neutral lipids of the INT 407 cells. Both cell lines secreted considerable amounts of dichloromyristic acid into the culture medium. Cellular or secreted metabolites shorter than dichloromyristic acid were not found. Taken together, the results suggest that human cells may (1) incorporate chlorinated fatty acids into membrane lipids and storage lipids, (2) metabolise cellular dichlorostearic acid to dichloropalmitic acid and dichloromyristic acid by ß-oxidation; but that further metabolism is hindered, possibly because of the chlorine atoms, and (3) remove formed dichloromyristic acid by secretion. The removal of cellular dichloromyristic acid might represent an important cellular defence mechanism and deserves further investigations.

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Chlorinated fatty acids in membrane lipids of fish

Cited by 14 publications

References 16 publications

Structural characterization of 5,6‐dichlorotetradecanoic acid, an isolated metabolite of 9,10‐dichlorooctadecanoic acid, by studying picolinyl esters, pyrrolidides and methyl esters with electron ionization mass spectrometry

Structural characterization of 5,6‐dichlorotetradecanoic acid, an isolated metabolite of 9,10‐dichlorooctadecanoic acid, by studying picolinyl esters, pyrrolidides and methyl esters with electron ionization mass spectrometry

Metabolic fate of 14C-labelled chlorinated and non-chlorinated fatty acids in goldfish (Carassius auratus)

Removal of Xenobiotic Dichlorostearic Acid from Phospholipids and Neutral Lipids in Cultured Human Cell Lines by ß‐Oxidation and Secretion of Dichloromyristic Acid

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