Alkylphenol ethoxylates and alkylphenols – update information on occurrence, fate and toxicity in aquatic environment

• Autorzy: Kovarova J , Blahova J. , Divisova L. , Svobodova Z.
• Języki publikacji: EN

Abstrakty

EN

Alkylphenols and their precursors, alkylphenol etoxylates, are a group of manmade chemicals used mainly as surfactants in domestic and industrial applications worldwide. It has been well established that they have endocrine disruption activity, hepatotoxic, genotoxic and other negative effects on animal and human health. In spite of the effort to reduce their use, they persist in the environment not only in industrial but also in remote regions, and were detected in the variety of natural matrices including air, water, soil as well as food products, and human blood and urine worldwide. This article summarizes their occurrence, fate in natural conditions, and toxicity including mode of action. A subject of our concern was the aquatic environment as the most important reservoir and target of their deleterious impact.

• Wydawca: -
• Czasopismo: Polish Journal of Veterinary Sciences
• Rocznik: 2013
• Tom: 16
• Numer: 4
• Opis fizyczny: p.763-772,fig.,ref.

Twórcy

autor

Kovarova J

• Department of Veterinary Public Health and Animal Welfare, Faculty of Veterinary Hygiene and Ecology, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho tr. 1/3, 612 42 Brno, Czech Republic

autor

Blahova J.

• Department of Veterinary Public Health and Animal Welfare, Faculty of Veterinary Hygiene and Ecology, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho tr. 1/3, 612 42 Brno, Czech Republic

autor

Divisova L.

• Department of Veterinary Public Health and Animal Welfare, Faculty of Veterinary Hygiene and Ecology, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho tr. 1/3, 612 42 Brno, Czech Republic

autor

Svobodova Z.

• Department of Veterinary Public Health and Animal Welfare, Faculty of Veterinary Hygiene and Ecology, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho tr. 1/3, 612 42 Brno, Czech Republic

Bibliografia

• Ahel M, Giger W (1993) Partitioning of alkylphenols and polyethoxylates between water and organic solvents. Chemosphere 26: 1471-1478.
• Ahel M, Scully FE Jr., Hoigne J, Giger W (1994) Photochemical degradation of nonylphenol and nonylphenol polyethoxylates in natural waters. Chemosphere 28: 1361-1368.
• Arditsoglou A, Voutsa D (2008) Determination of phenolic and steroid endocrine disrupting compounds in environmental matrices. Environ Sci Pollut Res 15: 228-236.
• Arukwe A, Forlin L, Goksoyr A (1997) Xenobiotic and steroid biotransformation enzymes in Atlantic salmon (Salmo salar) liver treated with an estrogenic compound, 4-nonylphenol. Environ Toxicol Chem 16: 2576-2583.
• Arukwe A, Goksoyr A, Thibaut R, Cravedi JP (2000) Metabolism and organ distribution of nonylphenol in Atlantic salmon (Salmo salar). Mar Environ Res 50: 141-145.
• Auriol M, Filali-Meknassi Y, Tyagi RD, Adams CD, Surampalli RY (2006) Endocrine disrupting compounds removal from wastewater, a new challenge. Process Biochem 41: 525-539.
• Basheer C, Lee HK, Tan KS (2004) Endocrine disrupting alkylphenols and bisphenol-A in coastal waters and supermarket seafood from Singapore. Mar Pollut Bull 48: 1145-1167.
• Bellingham M, Fowler PA, Amezaga MR, Whitelaw CM, Rhind SM, Cotinod C, Mandon-Pepin B, Sharpe RM, Evans NP (2010) Foetal hypothalamic and pituitary expression of gonadotrophin-releasing hormone and galanin systems is disturbed by exposure to sewage sludge chemicals via maternal ingestion. J Neuroendocrinol 22: 527-533.
• Beresford N, Routledge EJ, Harris CA, Sumpter JP (2000) Issues arising when interpreting results from an in vitro assay for estrogenic activity. Toxicol Appl Pharmacol 162: 22-33.
• Berryman D, Houde F, DeBlois C, O’Shea M (2004) Nonylphenolic compounds in drinking and surface waters downstream of treated textile and pulp and paper effluents: a survey and preliminary assessment of their potential effects on public health and aquatic life. Chemosphere 56: 247-255.
• Blackburn MA, Waldock MJ (1995) Concentrations of alkylphenols in rivers and estuaries in England and Wales. Water Res 29: 1623-1629.
• Bonefeld-Jorgensen EC, Long M, Hofmeister MV, Vinggaard AM (2007) Endocrine-disrupting potential of bisphenol A, bisphenol A dimethacrylate, 4-n-nonylphenol, and 4-n-octylphenol in vitro: new data and a brief review. Environ Health Perspect 115: 69-76.
• Brix R, Hvidt S, Carlsen L (2001) Solubility of nonylphenol and nonylphenol ethoxylates. On the possible role of micelles. Chemosphere 44: 759-763.
• Cheng CY, Liu LL, Ding WH (2006) Occurrence and seasonal variation of alkylphenols in marine organisms from the coast of Taiwan. Chemosphere 65: 2152-2159.
• Cheshenko K, Pakdel F, Segner H, Kah O, Eggen RI (2008) Interference of endocrine disrupting chemicals with aromatase CYP19 expression or activity, and consequences for reproduction of teleost fish. Gen Comp Endocrinol 155: 31-62.
• David A, Fenet H, Gomez E (2009) Alkylphenols in marine environments: distribution monitoring strategies and detection considerations. Mar Pollut Bull 58: 953-960.
• Dodds EC, Lawson W (1938) Molecular structure in relation to estrogenic activity; compounds without a phenantrene nucleus. Proc R Soc B-Biol Sci 125: 222-232.
• Dwyer FJ, Hardesty DK, Henke CE, Ingersoll CG, Mount DR, Bridges CM (1999) Assessing contaminant sensitivity of endangered and threatened species: toxicant classes. U.S. Environmental Protection Agency, Washington, DC. Ekelund R, Granmo A, Magnusson K, Berggren M, Bergman A (1993) Biodegradation of 4-nonylphenol in seawater and sediment. Environ Pollut 79: 59- 61.
• European Commission (2000) Directive 2000/60/EC of the European Parliament and of the council of 23 October 2000 establishing a Framework for Community action in the field of water policy. Official Journal of the European Communities L327: 1-72.
• European Commission (2006) Proposal for a Directive of the European Parliament and of the council on environmental quality standards in the field of water policy and amending Directive 2000/60/EC. Commission of the European Communities, Brusel.
• Facemire CF, Gross TS, Guillette LJ Jr. (1995) Reproductive impairment in the Florida panther: nature or nurture? Environ Health Perspect 103: 79-86.
• Fenlon KA, Johnson AC, Tyler CR, Hill EM (2010) Gas-liquid chromatography-tandem mass spectrometry methodology for the quantitation of estrogenic contaminants in bile of fish exposed to wastewater treatment works effluents and from wild populations. J Chromatogr A 1217: 112-118.
• Ferguson PL, Iden CR, Brownawell BJ (2001) Distribution and fate of neutral alkylphenol ethoxylate metabolites in a sewage-impacted urban estuary. Environ Sci Technol 35: 2428-2435.
• Ferreira-Leach AMR, Hill EM (2001) Bioconcentration and distribution of 4-tert-octylphenol residues in tissues of the rainbow trout (Oncorhynchus mykiss). Mar Environ Res 51: 75-89.
• Ferrara F, Fabietti F, Delise M, Funari E (2005) Alkylphenols and alkylphenol ethoxylates contamination of crustaceans and fishes from the Adriatic Sea (Italy). Chemosphere 59 1145-1150.
• Fox GA (2001) Wildlife as sentinels of human health effects in the Great Lakes – St. Lawrence basin. Environ Health Perspect 109: 853-861.
• Giger W, Brunner PH, Schaffner C (1984) 4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants. Science 225: 623-625.
• Gray MA, Metcalfe CD (1997) Induction of testis-ova in Japanese medaka (Oryzias latipes) exposed to p-nonylphenol. Environ Toxicol Chem 16: 1082-1086.
• Guenther K, Heinke V, Thiele B, Kleist E, Prast H, Raecker T (2002) Endocrine disrupting nonylphenols are ubiquitous in food. Environ Sci Technol 36: 1676-1680.
• Guillette LJ Jr., Brock JW, Rooney AA, Woodward AR (1999) Serum concentrations of various environmental contaminants and their relationship to sex steroid concentrations and phallus size in juvenile American alligators. Arch Environ Contam Toxicol 36: 447-455.
• Gutendorf B, Westendorf J (2001) Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. Toxicology 166: 79-89.
• Hwang DS, Lee JS, Rhee JS, Han J, Lee YM, Kim IC, Park GS, Lee J, Lee JS (2010) Modulation of p53 gene expression in the intertidal copepod Tigriopus japonicus exposed to alkylphenols. Mar Environ Res 69: S77-S80.
• Isobe T, Nishiyama A, Nakashima A, Takada H (2001) Distribution and behavior of nonylphenol, octylphenol and nonylphenol monoethoxylate in Tokyo metropolitan area: their association with aquatic particles and sedimentary distributions. Environ Sci Technol 35: 1041-1049.
• Jobling S, Sumpter JP (1993) Detergent components in sewage effluent are weakly oestrogenic to fish: An in vitro study using rainbow trout (Oncorhynchus mykiss) hepatocytes. Aquat Toxicol 27: 361-372.
• John DM, House WA, White GF (2000) Environmental fate of nonylphenol ethoxylates: differential adsorption of homologs to components of river sediment. Environ Toxicol Chem 19: 293-300.
• Jonsson G, Stokke TU, Cavcic A, Jorgensen KB, Beyer J (2008) Characterization of alkylphenol metabolites in fish bile by enzymatic treatment and HPLC-fluorescence analysis. Chemosphere 71: 1392-1400.
• Kitahashi T, Ogawa S, Parhar IS (2009) Cloning and expression of kiss2 in the zebrafish and medaka. Endocrinology 150: 821-831.
• Katzenellenbogen BS, Montano MM, Ediger TR, Sun J, Ekena K, Lazennec G, Martini PG, McInerney EM, Delage-Mourroux R, Weis K, Katzellenbogen JA (2000) Estrogen receptors: selective ligands, partners, and distinctive pharmacology. Recent Prog Horm Res 55: 163-195.
• Kelly, MA, Reid AM, Quinn-Hosey KM, Fogarty AM, Roche JJ, Brougham CA (2010) Investigation of the estrogenic risk to feral male brown trout (Salmo trutta) in the Shannon International River Basin District of Ireland. Ecotoxicol Environ Saf 73: 1658-1665.
• Kirk CJ, Bottomley L, Minican N, Carpenter H, Shaw S, Kohli N, Winter M, Taylor EW, Waring RH, Michelangeli F, Harris RM (2003) Environmental endocrine disrupters dysregulate estrogen metabolism and Ca²⁺ homeostasis in fish and mammals via receptor-independent mechanisms. Comp Biochem Phys A Mol Integr Physiol 135: 1-8.
• Kudo Y, Yamauchi K (2005) In vitro and in vivo analysis of the thyroid disrupting activities of phenolic and phenol compounds in Xenopus laevis. Toxicol Sci 84: 29-37.
• Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β. Endocrinology 139: 4252-4263.
• Kurihara R, Watanabe E, Ueda Y, Kakuno A, Fujii K, Shiraishi F, Hashimoto S (2007) Estrogenic activity in sediments contaminated by nonylphenol in Tokyo Bay (Japan) evaluated by vitellogenin induction in male mummichogs (Fundulus heteroclitus). Mar Pollut Bull 54: 1315-1320.
• Legler J, van den Brink CE, Brouwer A, Murk AJ, van der Saag PT, Vethaak AD, van der Burg B (1999) Development of a stably transfected estrogen receptor-mediated luciferase reporter gene assay in the human T47D breast cancer cell line. Toxicol Sci 48: 55-66.
• Li D, Kim M, Shim WJ, Yim UH, Oh JR, Kwon YJ (2004) Seasonal flux of nonylphenol in Han River, Korea. Chemosphere 56: 1-6.
• Li D, Dong M, Shim WJ, Hong SH, Oh JR, Yim UH, Jeung JH, Kanan N, Kim ES, Cho SR (2005) Seasonal and spatial distribution of nonylphenol and IBP in Saemangeum Bay, Korea. Mar Pollut Bull 51: 966-974.
• Liber K, Knuth ML, Stay FS (1999) An integrated evaluation of the persistence and effects of 4-nonylphenol in an experimental littoral ecosystem. Environ Toxicol Chem 18: 357-362.
• Lintelmann J, Katayama A, Kurihara N, Shore L, Wenzel A (2003) Endorcrine disruptors in the environment (IUPAC Technical Report). Pure Appl Chem 75: 631-681.
• Masuyama H, Hiramatsu Y, Kunitomi M, Kudo T, MacDonald PN (2000) Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate pregnane X receptor-mediated transcription. Mol Endocrinol 14: 421-428.
• Meier S, Andersen TE, Norberg B, Thorsen A, Taranger GL, Kjesbu OS, Dahle R, Morton HC, Klungsoyr J, Svardal A (2007) Effects of alkylphenols on the reproductive system of Atlantic cod (Godus morhua). Aquat Toxicol 81: 207-218.
• Meier S, Morton HC, Andersson E, Geffen AJ, Taranger GL, Larsen M, Petersen M, Djurhuus R, Klungsoyr J, Svardal A (2011) Low-dose exposure to alkylphenols adversely affects the sexual development of Atlantic cod (Gadus morhua): acceleration of the onset of puberty and delayed seasonal gonad development in mature female cod. Aquat Toxicol 105: 136-150.
• Nagarnaik PM, Mills MA, Boulanger B (2010) Concentrations and mass loadings of hormones, alkylphenols, and alkylphenol ethoxylates in healthcare facility wastewaters. Chemosphere 78: 1056-1062.
• Nakazawa K, Ohno Y (2001) Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors. Eur J Pharmacol 430: 175-183.
• Naylor CG, Mieure JP, Adams WJ, Weeks JA, Castaldi FJ, Ogle LD, Romano RR (1992) Alkylphenol ethoxylates in the environment. J Am Oil Chem Soc 69: 695-703.
• Nordic Council of Ministers (1996) Chemicals with estrogen-like effects. TemaNord, Copenhagen.
• Oakley AE, Clifton DK, Steiner RA (2009) Kisspeptin signalling in the brain. Endocr Rev 30: 713-743.
• Olea N, Pulgar R, Perez P, Olea-Serrano F, Rivas A, Novillo-Fertrell A, Pedraza V, Soto AM Sonnenschein C (1996) Estrogenicity of resin-based composites and sealants used in dentistry. Environ Health Perspect 104: 298-305.
• Paasivirta J, Rantio T (1991) Chloroterpenes and other organochlorines in Baltic, Finnish and Arctic wildlife. Chemosphere 22: 47-55.
• Pedersen SN, Christiansen LB, Pedersen KL, Korsgaard B, Bjerregaard P (1999) In vivo estrogenic activity of branched and linear alkylphenols in rainbow trout (Oncorhynchus mykiss). Sci Total Environ 233: 89-96.
• Peng X, Wang Z, Mai B, Chen F, Chen S, Tan J, Yu Y, Tang C, Li K, Zhang G, Yang C (2007) Temporal trends of nonylphenol and bisphenol A contamination in the Pearl River Estuary and the adjacent South China Sea recorded by dated sedimentary cores. Sci Total Environ 384: 393-400.
• Petrovic M, Barcelo D, Diaz A, Ventura F (2003) Low nanogram per liter determination of halogenated nonylphenols, nonylphenol carboxylates, and their non-halogenated precursors in water and sludge by liquid chromatography electrospray tandem mass spectrometry. J Am Soc Mass Spectrom 14: 516-527.
• Purdom CE, Hardiman PA, Bye VJ, Eno NC, Tyler CR, Sumpter JP (1994) Estrogenic effects from sewage treatment works. Chem Ecol 8: 275-285.
• Randak T, Zlabek V, Pulkrabova J, Kolarova J, Kroupova H, Siroka Z, Velisek J, Svobodova Z, Hajslova J (2009) Effects of pollution on chub in the River Elbe, Czech Republic. Ecotoxicol Environ Saf 72: 737-746.
• Renner R (1997) European bans on surfactant trigger transatlantic debate. Environ Sci Technol 31: 316A-320A.
• RPA (1999) Nonylphenol risk reduction strategy. Risk & Policy Analysts Limited, London.
• Rudel RA, Melly SJ, Geno PW, Sun G, Brody JG (1998) Identification of alkylphenols and other estrogenic phenolic compounds in wastewater, septage, and groundwater on Cape Cod, Massachusetts. Environ Sci Technol 32: 861-869.
• Safe SH, Gaido K (1998) Phytoestrogens and anthropogenic estrogenic compounds. Environ Toxicol Chem 17: 119-126.
• Servos MR (1999) Review of the aquatic toxicity, estrogenic responses and bioaccumulation of alkylphenols and alkylphenol polyethoxylates. Water Qual Res J Can 34: 123-177.
• Shang DY, Macdonald RW, Ikonomou MG (1999) Persistence of nonylphenol ethoxylate surfactants and their primary degradation products in sediments from near a municipal outfall in the Strait of Georgia, British Columbia, Canada. Environ Sci Technol 33: 1366-1372.
• Shiraishi H, Carter DS, Hites RA (1989) Identification and determination of tert-alkylphenols in carp from the Trenton Chhannel of the Detroit River, Michigan, USA. Biomed Environ Mass Spectrom 18: 478-483.
• Silva E, Rajapakse N, Kortenkamp A (2002) Something from “nothing” – eight weak estrogenic chemicals combined at concentrations below NOECs produce significant mixture effects. Environ Sci Technol 36: 1751-1756.
• Snyder SA, Keith TL, Pierens SL, Snyder EM, Giesy JP (2001) Bioconcentration of nonylphenol in fathead minnows (Pimephales promelas). Chemosphere 44: 1697-1702.
• Soares A, Guieysse B, Jefferson B, Cartmell E, Lester JN (2008) Nonylphenol in the environment: a critical review on occurrence, fate, toxicity and treatment in wastewaters. Environ Int 34: 1033-1049.
• Sole M, de Alda MJL, Castillo M, Porte C, Ladegaard-Pedersen K, Barcelo D (2000) Estrogenicity determination in sewage treatment plants and surface waters from the Catalonian area (NE Spain). Environ Sci Technol 34: 5076-5083.
• Sonnenschein C, Soto AM (1998) An updated review of environmental estrogen and androgen mimics and antagonists. J Steroid Biochem Mol Biol 65: 143-150.
• Soto AM, Justicia H, Wray JW, Sonnenschein C (1991) p-Nonyl-phenol: an estrogenic xenobiotic released from “modified” polystyrene. Environ Health Perspect 92: 167-173.
• Spence R, Gerlach G, Lawrence C, Smith C (2008) The behaviour and ecology of the zebrafish, Danio rerio. Biol Rev Camb Philos Soc 83: 13-34.
• Sumpter JP, Jobling S (1995) Vitellogenesis as a biomarker for estrogenic contamination of the aquatic environment. Environ Health Perspect 103: 173-178.
• Sumpter JP (1998) Xenoendocrine disrupters-environmental impacts. Toxicol Lett 102: 337-342.
• Tabata A, Kashiwada S, Ohnishi Y, Ishikawa H, Miyamoto N, Itoh M, Magara Y (2001) Estrogenic influences of estradiol-17 beta, p-nonylphenol and bis-phenol-A on Japanese Medaka (Oryzias liatipes) at detected environmental concentrations. Water Sci Technol 43: 109-116.
• Tollefsen KE (2002) Interaction of estrogen mimics singly and in combination, with plasma sex steroid-binding proteins in rainbow trout (Oncorhynchus mykiss). Aquat Toxicol 56: 215-225.
• Tollefsen KE, Nilsen AJ (2007) Binding of alkylphenols and alkylated non-phenolics to rainbow trout (Oncorhynchus mykiss) hepatic estrogen receptors. Ecotoxicol Environ Saf 69: 163-172.
• Tollefsen KE (2007) Binding of alkylphenols and alkylated non-phenolics to the rainbow trout (Onkorhynchus mykiss) plasma sex steroid-binding protein. Ecotoxicol Environ Saf 68: 40-48.
• Tollefsen KE, Nilsen A (2008) Binding of alkylphenols and alkylated non-phenolics to rainbow trout (Oncorhynchus mykiss) hepatic estrogen receptors. Ecotoxicol Environ Saf 69: 163-172.
• Tsuda T, Takino A, Kojima M, Harada H, Muraki K, Tsuji M (2000) 4-Nonylphenols and 4-tert-octylphenol in water and fish from rivers flowing into Lake Biwa. Chemosphere 41: 757- 762.
• Uguz C, Iscan M, Erguven A, Isgor B, Togan I (2003) The bioaccumulation of nonylphenol and its adverse effect on the liver of rainbow trout (Oncorhynchus mykiss). Environ Res 92: 262-270.
• US EPA (2005) Ambient aquatic life water quality criteria – nonylphenol Final. Office of Water, Office of Science and Technology, Washington, DC. Wallstrom M (2004) European Commission – SPEECH/04/203. REACH 2nd US-EU Chemical konference, Charlottesville. Warhurst AM (1995) An environmental assessment of alkylphenol ethoxylates and alkylphenols. Friends of the Earth. London, UK, 1-15.
• Weber LP, Hill RL Jr., Janz DM (2003) Developmental estrogenic exposure in zebrafish (Danio rerio) II: Histological evaluation of gametogenesis and organ toxicity. Aquat Toxicol 63: 431-446.
• Wolff MS, Toniolo PG, Lee EW, Rivera M, Dubin N (1993) Blood levels of organochlorine residues and risk of breast cancer. J Natl Cancer Inst 85: 648-652.
• Xia J, Niu C, Pei X (2010) Effects of chronic exposure to nonylphenol on locomotor activity and social behavior in zebrafish (Danio rerio). J Environ Sci 22: 1435-1440.
• Xie Z, Lakaschus S, Ebinghaus R, Caba A, Ruck W (2006) Atmospheric concentrations and air-sea exchanges of nonylphenol, tertiary octylphenol and nonylphenol monoethoxylate in the North Sea. Environ Poll 142: 170-180.
• Ying GG, Williams B, Kookana R (2002) Environmental fate of alkylphenols and alkylphenol ethoxylates – a review. Environ Int 28: 215- 226.
• Yang FX, Xu Y, Hui Y (2006) Reproductive effects of prenatal exposure to nonylphenol on zebrafish (Danio rerio). Comp Biochem Physiol C 142: 77-84.
• Zlabek V, Randak T, Cajka T, Kolarova J, Svobodova Z, Hajslova J, Jarkovsky J (2006) Alkylphenols in muscle of fish from rivers in the Czech Republic. Toxicol Lett 164: S177.