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Chlorinated fatty acids in freshwater fish and some biological effects of dichlorostearic acid

Vereskuns, Gastons (1999). Chlorinated fatty acids in freshwater fish and some biological effects of dichlorostearic acid. Diss. (sammanfattning/summary) Uppsala : Sveriges lantbruksuniv., Acta Universitatis agriculturae Sueciae. Agraria, 1401-6249 ; 203
ISBN 91-576-5717-3
[Doctoral thesis]

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Abstract

Chlorinated fatty acids (CFAs), major constituents of extractable, organically bound
chlorine in biota, are found in almost all fish studied in this respect. The concentration of
CFAs in fish varies considerably from some micrograms per gram of lipids in fish from
remote areas up to more than two thousand micrograms per gram of lipids in fish from the
vicinity of chlorine bleached kraft mills.

CFAs were liberated from fish lipids as the corresponding methyl esters and subjected
to enrichment. The methylated CFAs were studied by gas chromatography with electrolytic conductivity detection and/or mass spectrometry.

A considerable diversity of CFAs were found in fish, e.g. more than twenty were
indicated in pike from Latvian lakes. However, only part of the CFAs could be identified.
Pattern of CFAs differ considerably between fish from different areas. Thus, the patterns of CFAs in previously studied eel caught in Idefjord differ from the CFA patterns of pike
from Latvian lakes and also from that of perch from Latvian rivers. The main CFAs in
pike are likely chlorohydroxy fatty acids and in perch chlorinated, possibly sulphur containing
carboxylic acids. In the study of pike, CFAs were released from all lipid
classes considered: steryl esters, triacylglycerols, and phospholipids.

Because an enrichment is usually needed to make CFAs in lipids detectable, their
quantification may be difficult. A method to facilitate quantitative studies was developed,
where the enrichment factor is calculated using cholesterol.

Dichlorostearic acid was taken up by rats via food and were distributed within different
organs with the highest concentration in heart lipids and the lowest in muscle lipids.
Dichlorostearic acid was metabolised in rats yielding dichloropalmitic and
dichloromyristic acids. Some shorter-chain metabolites, possibly including dichlorotridecanoic
acid were found in the liver lipids. CFAs in the lipid extracts of rat tissues
were studied also by liquid chromatography with electrospray ionisation mass
spectrometry.

In a test for mutagenicity, the Ames test, dichlorostearic acid did not show any adverse
effects. In contrast, dichlorostearic acid caused inhibition of mutagenicity of some
indirectly-acting mutagens, possibly by the inactivation of Cytochrome P450 enzymes.
Certain effects on the ability of rat enzymes to activate indirectly acting mutagens by the
same acid was found also in in vivo studies. A possible explanation to this observation
might be an interaction of dichlorostearic acid with membrane bound enzymes or changes
in the membrane lipid composition resulting from the exposure to dichlorostearic acid.

Authors/Creators:Vereskuns, Gastons
Title:Chlorinated fatty acids in freshwater fish and some biological effects of dichlorostearic acid
Series/Journal:Acta Universitatis agriculturae Sueciae. Agraria (1401-6249)
Year of publishing :1999
Volume:203
Number of Pages:27
Papers/manuscripts:
NumberReferences
I.Vereskuns, G., Sundin, P., Wesén, C., Mu, H., Björn, H., Klavins, M., Göransson, A. & Odham, G. 1999. Chlorinated fatty acids and persistent organic pollutants in pike (Esox lucius) from Latvian lakes and from the Baltic. Submitted.
II.Vereskuns, G., Sundin, P., Nilsson, E., Olsson, A., Valters, K. & Wesén, C. 1999. Chlorinated fatty acids and related compounds in perch (Perca fluviatilis) from Latvian rivers. Manuscript.
III.Vereskuns, G., Wesén, C. & Sundin, P. 1999. Using cholesterol to calculate the enrichment factor of chlorinated fatty acids after preconcentration. Submitted.
IV.Vereskuns, G., Wesén, C., Skog, K. & Jägerstad, M. 1998. Inhibitory effect of threo-9,1O-dichlorostearic acid on the mutagenic activity of MeIQx, 2-AF and B[a]P in the Ames/Salmonella test. Mutation Research 416: 149-157.
V.Vereskuns, G., Wesén, C., Skog, K. & Sundin, P. 1999. Effects of dichlorostearic acid on organs and enzyme activity in rats. Manuscript.
Place of Publication:Uppsala
Publisher:Dept. of Environmental Assessment, Swedish University of Agricultural Sciences
ISBN for printed version:91-576-5717-3
ISSN:1401-6249
Language:English
Publication Type:Doctoral thesis
Full Text Status:Public
Agris subject categories.:P Natural resources > P01 Nature conservation and land resources
T Pollution > T01 Pollution
Subjects:(A) Swedish standard research categories 2011 > 1 Natural sciences > 104 Chemical Sciences > Organic Chemistry
Agrovoc terms:fishes, chlorine, organochlorine compounds, fatty acids, residues, cytochrome p450, water pollution, industrial pollutants, chromatography, mass spectrometry, mutagenicity, latvia, sweden
Keywords:fishes, chlorine, organochlorine compounds, fatty acids, residues, cytochrome p450, water pollution, industrial pollutants, chromatography, mass spectrometry, mutagenicity, latvia, sweden
URN:NBN:urn:nbn:se:slu:epsilon-e-1907
Permanent URL:
http://urn.kb.se/resolve?urn=urn:nbn:se:slu:epsilon-e-1907
ID Code:11190
Faculty:L - Lantbruksvetenskaplig fakultet (t.o.m. 2003)
Department:(NL, NJ) > Dept. of Environmental Assessment
Deposited By: Gunilla Åkerlund
Deposited On:19 May 2014 12:08
Metadata Last Modified:02 Dec 2014 11:06

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