Alkylphenol Metabolites in Fish Bile As Biomarkers of Exposure to Offshore Oil Industry Produced Water in Feral Fish

REFERENCES

• Aas , E. , Beyer , J. and Goksøyr , A. 2000 . Fixed wavelength fluorescence (FF) of bile as a monitoring tool for polyaromatic hydrocarbon exposure in fish: An evaluation of compound specificity, inner filter effect and signal interpretation . Biomarkers , 5 : 9 – 23 .
   PubMed Web of Science ®Google Scholar
• Ariese , F. , Beyer , J. , Jonsson , G. , Porte Visa , C. and Krahn , M. M. 2005 . Review of analytical methods for determining metabolites of polycyclic aromatic compounds (PACs) in fish bile . ICES-TIMES Tech. Marine Environ. Sci. , 39 : 1 – 41 .
   Google Scholar
• Arukwe , A. , Goksøyr , A. , Thibaut , R. and Cravedi , J. P. 2000a . Metabolism and organ distribution of nonylphenol in Atlantic salmon (Salmo salar) . Mar. Environ. Res. , 50 : 141 – 145 .
   PubMedGoogle Scholar
• Arukwe , A. , Thibaut , R. , Ingebrigtsen , K. , Celius , T. , Goksøyr , A. and Cravedi , J. P. 2000b . In vivo and in vitro metabolism and organ distribution of nonylphenol in Atlantic salmon (Salmo salar) . Aquat. Toxicol. , 49 : 289 – 304 .
   PubMed Web of Science ®Google Scholar
• Bennett , B. , Bowler , B. F. J. and Larter , S. R. 1996 . Determination of C-0-C-3 alkylphenols in crude oils and waters . Anal. Chem. , 68 : 3697 – 3702 .
   Google Scholar
• Bennett , B. , Noke , K. J. , Bowler , B. F. J. and Larter , S. R. 2007 . The accurate determination of C-0-C-3 alkylphenol concentrations in crude oils . Int. J. Environ. Anal. Chem. , 87 : 307 – 320 .
   Web of Science ®Google Scholar
• Beyer , J. , Jonsson , G. , Porte , C. , Krahn , M. M. and Ariese , F. 2010 . Analytical methods for determining metabolites of polycyclic aromatic hydrocarbon (PAH) pollutants in fish bile: A review . Environ. Toxicol. Pharmacol. , 30 : 224 – 244 .
   PubMed Web of Science ®Google Scholar
• Beyer , J. , Sandvik , M. , Skåre , J. U. , Egaas , E. , Hylland , K. , Waagbø , R. and Goksøyr , A. 1997 . Time- and dose-dependent biomarker responses in flounder (Platichthys flesus L) exposed to benzo[a]pyrene, 2,3,3′,4,4′,5-hexachlorobiphenyl (PCB-156) and cadmium . Biomarkers , 2 : 35 – 44 .
   PubMed Web of Science ®Google Scholar
• Boitsov , S. , Meier , S. , Klungsøyr , J. and Svardal , A. 2004 . Gas chromatography-mass spectrometry analysis of alkylphenols in produced water from offshore oil installations as pentafluorobenzoate derivatives . J. Chromatogr. A , 1059 : 131 – 141 .
   PubMed Web of Science ®Google Scholar
• Boitsov , S. , Mjøs , S. A. and Meier , S. 2007 . Identification of estrogen-like alkylphenols in produced water from offshore oil installations . Mar. Environ. Res. , 64 : 651 – 665 .
   PubMedGoogle Scholar
• Brendehaug , J. , Johnsen , S. , Bryne , K. H. , Gjøse , A. L. , Eide , T. H. and Aamot , E. 1992 . “ Toxicity testing and chemical characterization of produced water—A preliminary study ” . In Produced water, Technological/environmental issues and solutions , Edited by: Ray , M. J. and Engelhardt , F. R. Vol. 46 , 245 – 256 . New York : Plenum Press .
   Google Scholar
• Coldham , N. G. , Sivapathasundaram , S. , Dave , M. , Ashfield , L. A. , Pottinger , T. G. , Goodall , C. and Sauer , M. J. 1998 . Biotransformation, tissue distribution, and persistence of 4-nonylphenol residues in juvenile rainbow trout (Oncorhynchus mykiss) . Drug Metab. Dispos. , 26 : 347 – 354 .
   PubMed Web of Science ®Google Scholar
• Coleman , R. 1987 . Biochemistry of bile secretion . Biochem. J. , 244 : 249 – 261 .
   PubMed Web of Science ®Google Scholar
• Collier , T. K. and Varanasi , U. 1991 . Hepatic activities of xenobiotic metabolizing enzymes and biliary levels of xenobiotics in English sole (Parophrys vetulus) exposed to environmental contaminants . Arch. Environ. Contam. Toxicol. , 20 : 463 – 473 .
   Google Scholar
• Datta , S. , Loyo-Rosales , J. E. and Rice , C. P. 2002 . A simple method for the determination of trace levels of alkylphenolic compounds in fish tissue using pressurized fluid extraction, solid phase cleanup, and high-performance liquid chromatography fluorescence detection . J. Agric. Food Chem. , 50 : 1350 – 1354 .
   PubMedGoogle Scholar
• David , A. , Fenet , H. and Gomez , E. 2009 . Alkylphenols in marine environments: Distribution monitoring strategies and detection considerations . Mar. Pollut. Bull. , 58 : 953 – 960 .
   PubMed Web of Science ®Google Scholar
• Ferreira-Leach , A. M. R. and Hill , E. M. 2000 . Bioconcentration and metabolism of 4-tert-octylphenol in roach (Rutilus rutilus) fry . Analusis , 28 : 789 – 792 .
   Google Scholar
• Ferreira-Leach , A. M. R. and Hill , E. M. 2001 . Bioconcentration and distribution of 4-tert-octylphenol residues in tissues of the rainbow trout (Oncorhynchus mykiss) . Mar. Environ. Res. , 51 : 75 – 89 .
   PubMed Web of Science ®Google Scholar
• Grung , M. , Holth , T. F. , Jacobsen , M. R. and Hylland , K. 2009 . Polycyclic aromatic hydrocarbon (PAH) metabolites in Atlantic cod exposed via water or diet to a synthetic produced water . J. Toxicol. Environ. Health A , 72 : 254 – 265 .
   PubMed Web of Science ®Google Scholar
• Grøsvik , B. E. , Meier , S. , Westrheim , K. , Skarphéðinsdóttir , H. , Liewenborg , B. , Balk , L. and Klungsøyr , J. 2007 . Condition monitoring in the water column 2005: Oil hydrocarbons in fish from Norwegian waters , 2 Bergen, , Norway : Institute of Marine Research .
   Google Scholar
• Harman , C. , Thomas , K. V. , Tollefsen , K. E. , Meier , S. , Bøyum , O. and Grung , M. 2009 . Monitoring the freely dissolved concentrations of polycyclic aromatic hydrocarbons (PAH) and alkylphenols (AP) around a Norwegian oil platform by holistic passive sampling . Mar. Pollut. Bull. , 58 : 1671 – 1679 .
   PubMedGoogle Scholar
• Horie , M. , Kobayashi , H. , Ishii , R. , Sait , K. , Nakazawa , H. and Makino , T. 2007 . Determination of nonylphenol and octylphenol in fish and shellfish by high-performance liquid chromatography/electrospray mass spectrometry . Bunseki Kagaku , 56 : 1037 – 1043 .
   Google Scholar
• Jonsson , G. , Cavcic , A. , Stokke , T. U. , Beyer , J. , Sundt , R. C. and Brede , C. 2008a . Solid–phase analytical derivatization of alkylphenols in fish bile for gas chromatography-mass spectrometry analysis . J. Chromatogr. A , 1183 : 6 – 14 .
   PubMedGoogle Scholar
• Jonsson , G. , Stokke , T. U. , Cavcic , A. , Jørgensen , K. B. and Beyer , J. 2008b . Characterization of alkylphenol metabolites in fish bile by enzymatic treatment and HPLC-fluorescence analysis . Chemosphere , 71 : 1392 – 1400 .
   PubMedGoogle Scholar
• Klungsøyr , J. , Balk , L. , Berntssen , M. H. G. , Beyer , J. , Melbye , A. G. and Hylland , K. 2003 . Contamination of fish in the North Sea by the offshore oil and gas industry: Summary report to NFR , Bergen, , Norway : Institute of Marine Research, Bergen, Norway .
   Google Scholar
• Lewis , S. K. and Lech , J. J. 1996 . Uptake, disposition, and persistence of nonylphenol from water in rainbow trout (Oncorhynchus mykiss) . Xenobiotica , 26 : 813 – 819 .
   PubMed Web of Science ®Google Scholar
• Meier , S. , Andersen , T. E. , Norberg , B. , Thorsen , A. , Taranger , G. L. , Kjesbu , O. S. , Dale , R. , Morton , H. C. , Klungsøyr , J. and Svardal , A. 2007 . Effects of alkylphenols on the reproductive system of Atlantic cod (Gadus morhua) . Aquat. Toxicol. , 81 : 207 – 218 .
   PubMed Web of Science ®Google Scholar
• Meier , S. , Klungsøyr , J. , Boitsov , S. , Eide , T. and Svardal , A. 2005 . Gas chromatography-mass spectrometry analysis of alkylphenols in cod (Gadus morhua) tissues as pentafluorobenzoate derivatives . J. Chromatogr. A , 1062 : 255 – 268 .
   PubMedGoogle Scholar
• Meldahl , A. C. , Nithipatikom , K. and Lech , J. J. 1996 . Metabolism of several C-14-nonylphenol isomers by rainbow trout (Oncorhynchus mykiss): In vivo and in vitro microsomal metabolites . Xenobiotica , 26 : 1167 – 1180 .
   PubMed Web of Science ®Google Scholar
• Mills , L. J. and Chichester , C. 2005 . Review of evidence: Are endocrine-disrupting chemicals in the aquatic environment impacting fish populations? . Sci. Total Environ. , 343 : 1 – 34 .
   PubMed Web of Science ®Google Scholar
• Myhre , L. P. , Baussant , T. , Sundt , R. , Sanni , S. , Vabø , R. , Skjoldal , H. R. and Klungsøyr , J. 2004 . Risk assessment of reproductive effects of alkyl phenols in produced water on fish stocks in the North Sea , Stavanger, , Norway : RF-Akvamiljø, AM–2004/018 .
   Google Scholar
• OSPARCOM . 2009 . Discharges, spills and emissions from offshore oil and gas installations in 2007, including the assessment of data reported in 2006 and 2007 , Offshore Industry Series, OSPAR Commission, London, UK. Publication Number 452/2009 .
   Google Scholar
• Pedersen , R. T. and Hill , E. M. 2002 . Tissue distribution and depuration of 4-tert-octylphenol residues in the cyprinid fish, Scardinius erythrophthalmus . Environ. Sci. Technol. , 36 : 3275 – 3283 .
   PubMed Web of Science ®Google Scholar
• Pedersen , R. T. and Hill , E. N. 2000 . Biotransformation of the xenoestrogen 4-tert-octylphenol in hepatocytes of rainbow trout (Oncorhynchus mykiss) . Xenobiotica , 30 : 867 – 879 .
   PubMed Web of Science ®Google Scholar
• Rice , C. P. , Schmitz-Afonso , I. , Loyo-Rosales , J. E. , Link , E. , Thoma , R. , Fay , L. , Altfater , D. and Camp , M. J. 2003 . Alkylphenol and alkylphenol-ethoxylates in carp, water, and sediment from the Cuyahoga River, Ohio . Environ. Sci. Technol. , 37 : 3747 – 3754 .
   PubMed Web of Science ®Google Scholar
• Riksheim , H. and Johnsen , S. 1994 . Determination of produced water contaminants in the marine environment . Soc. Petrol. Eng. SPE , 27151 : 479 – 484 .
   Google Scholar
• Routledge , E. J. and Sumpter , J. P. 1997 . Structural features of alkylphenolic chemicals associated with estrogenic activity . J. Biol. Chem. , 272 : 3280 – 3288 .
   PubMed Web of Science ®Google Scholar
• Røe , T. I. 1998 . Produced water discharges to the North Sea: A study of bioavailability of organic produced water compounds to marine organisms , Dr. scient. thesis, Faculty of Chemistry and Biology. Trondheim, Norway: Norwegian University of Science and Technology (NTNU) .
   Google Scholar
• Schmitz-Afonso , I. , Loyo-Rosales , J. E. , Aviles , M. D. , Rattner , B. A. and Rice , C. P. 2003 . Determination of alkylphenol and alkylphenolethoxylates in biota by liquid chromatography with detection by tandem mass spectrometry and fluorescence spectroscopy . J. Chromatogr. A , 1010 : 25 – 35 .
   PubMed Web of Science ®Google Scholar
• Smith , M. D. and Hill , E. M. 2004 . Uptake and metabolism of technical nonylphenol and its brominated analogues in the roach (Rutilus rutilus) . Aquat. Toxicol. , 69 : 359 – 369 .
   PubMed Web of Science ®Google Scholar
• Smith , M. D. and Hill , E. M. 2006 . Profiles of short chain oligomers in roach (Rutilus rutilus) exposed to waterborne polyethoxylated nonylphenols . Sci. Total Environ. , 356 : 100 – 111 .
   PubMed Web of Science ®Google Scholar
• Sundt , R. C. and Björkblom , C. 2011 . Effects of produced water discharges on the reproductive system of prespawning Atlantic cod (Gadhus morhua) . J. Toxicol. Environ. Health A , : 543 – 554 .
   PubMedGoogle Scholar
• Sundt , R. C. , Baussant , T. and Beyer , J. 2009a . Uptake and tissue distribution of C4-C7 alkylphenols in Atlantic cod (Gadus morhua): Relevance for biomonitoring of produced water discharges from oil production . Mar. Pollut. Bull. , 58 : 72 – 79 .
   PubMedGoogle Scholar
• Sundt , R. C. , Meier , S. , Jonsson , G. , Sanni , S. and Beyer , J. 2009b . Development of a laboratory exposure system using marine fish to carry out realistic effect studies with produced water discharged from offshore oil production . Mar. Pollut. Bull. , 58 : 1382 – 1388 .
   PubMedGoogle Scholar
• Tabata , A. , Kashiwada , S. , Ohnishi , Y. , Ishikawa , H. , Miyamoto , N. , Itoh , M. and Magara , Y. 2001 . Estrogenic influences of estradiol-17 beta, p-nonylphenol and bisphenol-A on Japanese medaka (Oryzias latipes) at detected environmental concentrations . Water Sci. Technol. , 43 : 109 – 116 .
   PubMed Web of Science ®Google Scholar
• Thibaut , R. , Debrauwer , L. , Rao , D. and Cravedi , J. P. 1998 . Characterization of biliary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss) . Xenobiotica , 28 : 745 – 757 .
   PubMed Web of Science ®Google Scholar
• Thibaut , R. , Debrauwer , L. , Rao , D. and Cravedi , J. P. 1999 . Urinary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss) . Sci. Total Environ. , 233 : 193 – 200 .
   PubMedGoogle Scholar
• Thibaut , R. , Monod , G. and Cravedi , J. P. 2002 . Residues of C-14-4n-nonylphenol in mosquitofish (Gambusia holbrooki) oocytes and embryos during dietary exposure of mature females to this xenohormone . Mar. Environ. Res. , 54 : 685 – 689 .
   PubMedGoogle Scholar
• Thomas , K. V. , Balaam , J. , Hurst , M. R. and Thain , J. E. 2004 . Identification of in vitro estrogen and androgen receptor agonists in North Sea offshore produced water discharges . Environ. Toxicol. Chem. , 23 : 1156 – 1163 .
   PubMed Web of Science ®Google Scholar
• Tollefsen , K. E. and Nilsen , A. J. 2008 . Binding of alkylphenols and alkylated non-phenolics to rainbow trout (Oncorhynchus mykiss) hepatic estrogen receptors . Ecotoxicol. Environ. Safety , 69 : 163 – 172 .
   PubMed Web of Science ®Google Scholar
• Tollefsen , K. E. , Ingebrigtsen , K. , Olsen , A. J. , Zachariassen , K. E. and Johnsen , S. 1998 . Acute toxicity and toxicokinetics of 4-heptylphenol in juvenile Atlantic cod (Gadus morhua L.) . Environ. Toxicol. Chem. , 17 : 740 – 746 .
   Google Scholar
• Utvik , T. I. R. 1999 . Chemical characterisation of produced water from four offshore oil production platforms in the North Sea . Chemosphere , 39 : 2593 – 2606 .
   Web of Science ®Google Scholar
• van der Oost , R. , Beyer , J. and Vermeulen , N. P. E. 2003 . Fish bioaccumulation and biomarkers in environmental risk assessment: A review . Environ. Toxicol. Pharmacol. , 13 : 57 – 149 .
   PubMed Web of Science ®Google Scholar