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

Fish Physiology and Biochemistry volume 30, pages 13–20 (2004)Cite this article

Abstract

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 CO2 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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References

  • I.. Ahlgren G. Ahlgren (1975) Methods of Chemical Analysis, Compiled for Instructions in Limnology Department of Limnology Uppsala

    Google Scholar 

  • Björn H. (1999). Uptake, turnover and distribution of chlorinated fatty acids in aquatic biota. Doctoral thesis, Lund University

  • Björn H., Sundin P..,Wesén C. (1998a). In: Environmental Toxicology, Current Developments, pp. 159–170. Edited by J. Rose, Gordon and Breach Science Publishers, Amsterdam

  • H. Björn P. Sundin C. Wesén H. Mu K. Martinsen A.L. Kvernheim J.. Skramstad Odham G. (1998) ArticleTitleChlorinated fatty acids in membrane lipids of fish Naturwissenschaften 85 229–232 Occurrence Handle10.1007/s001140050488 Occurrence Handle9672905

    Article  PubMed  Google Scholar 

  • E.G.. Bligh W.J. Dyer (1959) ArticleTitleA rapid method of total lipid extraction and purification Can. J. Biochem. Physiol. 37 911–917 Occurrence Handle1:CAS:528:DyaG1MXhtVSgt70%3D Occurrence Handle13671378

    CAS  PubMed  Google Scholar 

  • K.F.. Buechler J.M. Lowenstein (1990) ArticleTitleThe involvement of carnitine intermediates in peroxisomal fatty acid oxidation: a study with 2-bromofatty acids Arch. Biochem. Biophys. 281 233–238 Occurrence Handle10.1016/0003-9861(90)90437-4 Occurrence Handle1:CAS:528:DyaK3cXltFarurg%3D Occurrence Handle2393299

    Article  CAS  PubMed  Google Scholar 

  • G.N. Cherr J.M. Shenker C.. Lundmark K.O. Turner (1987) ArticleTitleToxic effects of selected bleach kraft mill effluent constituents on sea urchin sperm cells Environ. Toxicol. Chem. 6 561–569 Occurrence Handle1:CAS:528:DyaL2sXksFersrk%3D

    CAS  Google Scholar 

  • H.B.S. Conacher R.K. Chadha J.F. Lawrence S.M.. Charbonneau F. Bryce (1984) ArticleTitleMammary transfer and metabolism in the rat of halogenated fatty acids of halogenated olive oil Lipids 19 637–642 Occurrence Handle1:CAS:528:DyaL2MXksFOm Occurrence Handle6503626

    CAS  PubMed  Google Scholar 

  • H.M.. Cunningham G.A. Lawrence (1976) ArticleTitleA comparison of the distribution and elimination of oleic and chlorinated oleic acids and their metabolites in rats Fd Cosmet. Toxicol. 14 283–288 Occurrence Handle1:CAS:528:DyaE28XlvVOguro%3D

    CAS  Google Scholar 

  • H.M.. Cunningham G.A. Lawrence (1977) ArticleTitleAbsorption and metabolism of chlorinated fatty acids and triglycerides in rats Fd Cosmet. Toxicol. 15 101–103 Occurrence Handle10.1016/S0015-6264(77)80313-1 Occurrence Handle1:CAS:528:DyaE2sXksVyksb0%3D

    Article  CAS  Google Scholar 

  • H.M.. Cunningham G.A. Lawrence (1977) ArticleTitleAbsorption and distribution studies on chlorinated oleic acid and extracts of chlorinated lipid and protein fractions of flour in rats Fd Cosmet. Toxicol. 15 105–108 Occurrence Handle10.1016/S0015-6264(77)80314-3 Occurrence Handle1:CAS:528:DyaE2sXktlOmsr0%3D

    Article  CAS  Google Scholar 

  • G.. Ewald P. Sundin (1993) ArticleTitleRelease of ATP from ELD cells after exposure to stearic, mono-chlorostearic, dichlorostearic and oleic acid Pharmacol. Toxicol. 73 159–162 Occurrence Handle1:CAS:528:DyaK2cXntFSgsA%3D%3D Occurrence Handle8265520

    CAS  PubMed  Google Scholar 

  • G. Ewald P. Sundin J.. Skramstad P. Frøyen (1996) ArticleTitleDistribution of 14C from ingested, radiolabelled dichlorostearic, stearic and oleic acid in body and in lipids of perch, Perca fluviatilis Aquat. Toxicol. 36 129–139 Occurrence Handle10.1016/S0166-445X(96)00009-4 Occurrence Handle1:CAS:528:DyaK2sXktVGmtw%3D%3D

    Article  CAS  Google Scholar 

  • Goksøyr A..,Larsen H.E. (1993). Effekter av klorerte fettsyrer og fettextrakter på cytokrom P450-systemet hos laks. Report, Laboratory for Marine Molecular Biology, University of Bergen. (In Norwegian)

  • M.I.. Gurr J.L. Harwood (1991) Lipid Biochemistry, An Introduction Chapman & Hall London

    Google Scholar 

  • H. Håkansson P. Sundin T. Andersson B. Brunström L. Dencker M. Engwall G. Ewald M. Gilek G. Holm S. Honkasalo J. Idestam-Almquist P. Jonsson N. Kautsky G Lundberg A Lund Kvernheim K. Martinsen L. Norrgren M. Pesonen M. Rundgren M. Stålberg M.. Tarkpea C. Wesén (1991) ArticleTitleIn vivo and in vitro toxicity of fractionated fish lipids, with particular regard to their content of chlorinated organic compounds Pharmacol. Toxicol. 69 459–471 Occurrence Handle1766922 Occurrence Handle10.1111/j.1600-0773.1991.tb01329.x

    Article  PubMed  Google Scholar 

  • A. Jernelöv (1989) ArticleTitleHypotes kan förklara organiskt klor i fisk Kemisk tidskrift 4 119–122

    Google Scholar 

  • Jobling H. (1993). In: Fish Ecophysiology, pp. 1–43. Edited by J.C. Rankin.,F.B. Jensen. Chapman and Hall, London

  • B.A. Jones I.J. Tinsley G.. Wilson R.R. Lowry (1983) ArticleTitleToxicology of brominated fatty acids: Metabolite concentration and heart and liver changes Lipids 18 327–334 Occurrence Handle1:CAS:528:DyaL3sXktVChsrw%3D Occurrence Handle6865665

    CAS  PubMed  Google Scholar 

  • J.M.. Leach A.N. Thakore (1977) ArticleTitleCompounds toxic to fish in pulp mill waste streams Prog. Wat. Technol. 9 787–798

    Google Scholar 

  • J.E. Milley R.K. Boyd J.M. Curtis C.. Musial Uthe J.F. (1997) ArticleTitleDichloromyristic acid, a major component of organochlorine load in lobster digestive gland Environ. Sci. Technol. 31 535–541 Occurrence Handle10.1021/es960407x Occurrence Handle1:CAS:528:DyaK2sXmtVyjtQ%3D%3D

    Article  CAS  Google Scholar 

  • H.F. Mohamed T.L.. Andreone R.L. Dryer (1980) ArticleTitleMitochondrial metabolism of (D,L)- threo- 9,10-dibromopalmitic acid Lipids 15 255–262 Occurrence Handle1:CAS:528:DyaL3cXks1arsr0%3D Occurrence Handle7374379

    CAS  PubMed  Google Scholar 

  • Mu H. (1996). Analysis of halogenated fatty acids in fish lipids by gas chromatography with electrolytic conductivity detection and mass spectrometry. Doctoral thesis, Lund University

  • H. Mu C. Wesén P. Sundin E. Nilsson (1996) ArticleTitleGas chromatographic and mass spectrometric identification of tetrachloroalkanoic and dichloroalkenoic acids in eel lipids J. Mass Spectrom. 31 517–526 Occurrence Handle10.1002/(SICI)1096-9888(199605)31:5<517::AID-JMS325>3.0.CO;2-A Occurrence Handle1:CAS:528:DyaK28XjtVenur8%3D

    Article  CAS  Google Scholar 

  • H. Mu C.. Wesén P. Sundin (1997) ArticleTitleHalogenated fatty acids I: Formation and occurrence in lipids TRAC 16 266–274 Occurrence Handle1:CAS:528:DyaK2sXksVeqsL4%3D

    CAS  Google Scholar 

  • H. Mu P.. Sundin C. Wesén (1997) ArticleTitleHalogenated fatty acids II: Methods of determination in lipids TRAC 16 274–286 Occurrence Handle1:CAS:528:DyaK2sXksVeqtrk%3D

    CAS  Google Scholar 

  • H. Mu G. Ewald E. Nilsson P. Sundin C. Wesén (2004) ArticleTitleFate of chlorinated fatty acids in migrating sockeye salmon, and their transfer to Arctic grayling Environ. Sci. Technol. 38 5548–5554 Occurrence Handle10.1021/es048744q Occurrence Handle1:CAS:528:DC%2BD2cXns1Wisb0%3D Occurrence Handle15575271

    Article  CAS  PubMed  Google Scholar 

  • Neal R.A. (1980). In: Water chlorination. Environmental impact and health effects. Volume 3, pp. 1007–1017. Edited by R.L. Jolly, W.A. Brungs, R.B. Cumming, V.A. Jacobs. Ann Arbor Science Publishers Inc., Michigan

  • S.L.. Neidleman J. Geigert (1986) Biohalogenation: Principles, Basic Roles and Applications Ellis Horwood Ltd Chichester

    Google Scholar 

  • W.H. Newsome P. Andrews H.B.S. Conacher R.R.. Rao A. Chatt (1993) ArticleTitleTotal organochlorine content of fish from the Great lakes JAOAC Int. 76 703–706 Occurrence Handle1:CAS:528:DyaK2cXntFer

    CAS  Google Scholar 

  • D.H. Sephton W.E.. Macphee WR Driedzic (1991) ArticleTitleMetabolic enzyme activities, oxygen consumption and glucose utilization in sea raven (Hemitripterus americanus) erythrocytes J. Exp. Biol. 159 407–418 Occurrence Handle1:CAS:528:DyaK3MXmt1ersrg%3D

    CAS  Google Scholar 

  • A. Södergren B.E. Bengtsson P. Jonsson S. Lagergren Å. Larsson M.. Olsson L. Renberg (1988) ArticleTitleSummary of results from the Swedish project Environment/Cellulose Wat. Sci. Technol. 20 49–60

    Google Scholar 

  • R.H.. Voss A. Rapsomatiotis (1985) ArticleTitleAn improved solvent extraction based procedure for the gas chromatographic analysis of resin.and fatty acids in pulp mill effluents J. Chromatogr. 346 205–214 Occurrence Handle10.1016/S0021-9673(00)90506-5 Occurrence Handle1:CAS:528:DyaL2MXmt1SntbY%3D

    Article  CAS  Google Scholar 

  • Wesén C. (1995). Chlorinated fatty acids in fish lipids. Doctoral thesis, Lund University

  • C. Wesén H. Mu A.. Lund-Kvernhem P. Larsson (1992) ArticleTitleIdentification of chlorinated fatty acids in fish lipids by partitioning studies and by gas chromatography with Hall electrolytic conductivity detection J. Chromatogr. 625 257–269 Occurrence Handle10.1016/0021-9673(92)85210-K

    Article  Google Scholar 

  • C. Wesén H. Mu P. Sundin P. Frøyen J.. Skramstad G. Odham (1995) ArticleTitleGas chromatographic-mass spectrometric identification of chlorinated octadecanoic acids in eel lipids J. Mass Spectrom. 30 959–968

    Google Scholar 

  • Wesén C., Mu H., Sundin P., Ringstad O..,Odham G. (1995b). In: Naturally produced organohalogens, pp. 307–316. Edited by A. Grimvall.,E.W.B. de Leer. Kluwer Academic Publishers, Dordrecht

  • R.H.. White L.P. Hager (1977) ArticleTitleOccurrence of fatty acid chlorohydrins in jellyfish lipids Biochemistry 16 4944–4948 Occurrence Handle10.1021/bi00641a032 Occurrence Handle1:CAS:528:DyaE2sXlvFOltL8%3D Occurrence Handle20944

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Chemical Ecology and Ecotoxicology, Department of Ecology, Ecology Building, Lund University, SE-223 62, Lund, Sweden

    H. Björn

  2. Department of Chemical Engineering, Lund University, P.O. Box 124, SE-221 00, Lund, Sweden

    G. Ewald

  3. Department of Environmental Assessment, Swedish University of Agricultural Sciences, P.O. Box 7050, SE-750 07, Uppsala, Sweden

    P. Sundin

  4. Department of Technical Analytical Chemistry, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00, Lund, Sweden

    C. Wesén

  5. Department of Chemistry, University of Oslo, P.O. Box 1033, NO-0315, Oslo, Norway

    J. Skramstad & P. Frøyen

Authors
  1. H. Björn
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  2. G. Ewald
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  3. P. Sundin
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  4. C. Wesén
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  5. J. Skramstad
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  6. P. Frøyen
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Corresponding author

Correspondence to G. Ewald.

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Björn, H., Ewald, G., Sundin, P. et al. Metabolic fate of 14C-labelled chlorinated and non-chlorinated fatty acids in goldfish (Carassius auratus). Fish Physiol Biochem 30, 13–20 (2004). https://doi.org/10.1007/s10695-004-4153-2

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  • DOI: https://doi.org/10.1007/s10695-004-4153-2

Keywords

  • chlorinated fatty acids
  • fatty acid turnover
  • lipid metabolism
  • respiration

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