On Chlorinated Fatty Acids as Environmental Pollutants

Björn, Helena; Sundin, Peter; Wesén, Clas

doi:10.4324/9780203305515_chapter_8

Cited by 3 publications

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“…Studies during the last few years have indicated that chlorinated fatty acids represent a group of potentially hazardous organochlorine pollutants dispersed in the environment (Björn et al 1998a;Ewald 1999). The present study is the first one in which the incorporation and metabolism of chlorinated fatty acids have been investigated in cells of human origin.…”

Section: Discussionmentioning

confidence: 92%

“…A major portion of the extractable organically bound chlorine in fish and other aquatic organisms consists of longchain fatty acids with one or more chlorine atoms bound to their carbon skeleton (Wesén et al 1992(Wesén et al & 1995Mu et al 1996a & b). There are reasons to suspect that these chlorinated fatty acids represent a group of potentially hazardous organochlorine pollutants in the environment (Björn et al 1998a;Ewald 1999).…”

mentioning

confidence: 99%

“…So far, the effects of chlorinated fatty acids in biological systems have been investigated in a limited number of studies, using marine organisms and rodents, and the results have indicated that chlorinated fatty acids might have negative effects on reproduction-related processes, growth, and mortality (Björn et al 1998a). The proposed negative effect of chlorinated fatty acids on membrane integrity was confirmed in a study demonstrating that free chlorinated stearic acids cause ATP leakage from cultured cells at lower concentrations than free normal stearic acid (Ewald & Sundin 1993).…”

mentioning

confidence: 99%

“…There are reasons to suspect that these chlorinated fatty acids represent a group of potentially hazardous organochlorine pollutants in the environment (Björn et al 1998a;Ewald 1999).…”

mentioning

confidence: 99%

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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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Section: Discussionmentioning

confidence: 92%

mentioning

confidence: 99%

mentioning

confidence: 99%

“…There are reasons to suspect that these chlorinated fatty acids represent a group of potentially hazardous organochlorine pollutants in the environment (Björn et al 1998a;Ewald 1999).…”

mentioning

confidence: 99%

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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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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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Chlorinated fatty acids - Environmental pollutants with intriguing properties

Ewald

1998

Chemosphere

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On Chlorinated Fatty Acids as Environmental Pollutants

Cited by 3 publications

References 0 publications

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

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

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

Chlorinated fatty acids - Environmental pollutants with intriguing properties

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