Abstract
Seven phthalate by-products were investigated for the first time, in target tissues of roach from a contaminated river of the Ile-de-France district. All parent phthalates were bioaccumulated in liver and muscle and liver contents were correlated with river concentrations (p < 0.01). All metabolites were found in liver, plasma and bile. The mono-iso-butyl phthalate (MiBP; 1.6 μg g−1 dw of liver), followed by mono-n-butyl phthalate (MnBP; 1.5 μg g−1 dw of liver) were the most abundant ones. Among the three metabolites of di-ethylhexyl phthalate (DEHP), mono (2-ethylhexyl) phthalate (MEHP) predominated in bile (15.5 ng ml−1) and liver (0.237 μg g−1 dw), whereas in plasma, it was mono (2-ethyl-5-hydroxyhexyl) phthalate – MEHHP (214 ng ml−1). In liver, MEHP/DEHP ratios ranged from 0.04 to 0.2. Among the oxidized metabolites, only mono (2-ethyl-5-oxohexyl) phthalate (MEOHP) was correlated (p < 0.05) with parent DEHP and appeared to be a more reliable marker of DEHP impact than the monoester.
Similar content being viewed by others
References
Agency GFE (2011) Substance monograph: phthalates New and updated reference values for monoesters and oxidizes metabolites in urine of adults and children. Bundesgesundheitsblatt 54:770–785
Barron MG, Albro PW, Hayton WL (1995) Biotransformation of di(2-ethylhexyl) phthalate by rainbow trout. Environ Toxicol Chem 14:873–876
Blount BC, Milgram KE, Silva MJ, Malek NA, Reidy JA, Needham LL, Brock JW (2000) Quantitative detection of eight phthalate metabolites in human urine using HPLC–APCI–MS/MS. Anal Chem 72:4127–4134
Erkekoglu P, Rachidi W, Yuzugullu OG, Giray B, Favier A, Ozturk M, Hincal F (2010) Evaluation of cytotoxicity and oxidative DNA damaging effects of di(2-ethylhexyl)-phthalate (DEHP) and mono(2-ethylhexyl)-pthalate (MEHP) on MA-10 Leydig cells and protection by selenium. Toxicol Appl Pharmacol 248:52–62
Frederiksen H, Jorgensen N, Andersson AM (2010) Correlations between phthalate metabolites in urine, serum and seminal plasma from young Danish men determined by isotope dilution liquid chromatography tandem mass spectrometry. J Anal Toxicol 34:400–410
Frederiksen H, Kolstrup Søgaard Nielsen J, Aarøe Mørckorgensen T, Winton Hansen P, Fangel Jensen J, Nielsen O, Andersson AM, Knudsen LE (2013) Urinary excretion of phthalate metabolites, phenols and parabens in rural and urban Danish mother–child pairs. Int J Hyg Environ Health 216:772–783
Gerbron M, Geraudie P, Fernandes D, Rotchell JM, Porte C, Minier C (2014) Evidence of altered fertility in female roach (Rutilus rutilus) from the River Seine (France). Environ Pollut 191:58–62
Inoue Y, Hashizume N, Yoshida T, Murakami H, Suzuki Y, Koga Y, Takeshige R, Kikushima E, Yakata N, Otsuka M (2012) Comparison of bioconcentration and biomagnification factors for poorly water-soluble chemicals using common carp (Cyprinus carpio L.). Arch Environ Toxicol 63:241–248
Kato K, Silva MJ, Reidy JA, Hurtz ID, Malek NA, Needham LL, Nakazawa H, Barr DB, Calafat AM (2004) Mono-(2-ethyl-5-hydroxyhexyl) phthalate and mono-(2-ethyl-5-oxohexyl) phtalate as biomarkers for human exposure assessment to di(2-ethylhexyl) phthalate. Environ Health Perspect 112:327–330
Kessler W, Numtip W, Grote K, Csanady GA, Chahoud I, Filser JG (2004) Blood burden of di(2-ethylhexyl) phthalate and its primary metabolite mono(2-ethylhexyl)phthalate in pregnant and nonpregnant rats and marmosets. Toxicol Appl Pharmacol 195:142–153
Latini G, De Felice C, Presta G, Del Vecchio A, Paris I, Ruggieri F, Mazzeo P (2003) In Utero exposure to di-(2-ethylhexyl) phthalate and duration of human pregnancy. Environ Health Perspect 111:1783–1785
Minier C, Caltot G, Leboulanger F, Hill EM (2000) An investigation of the incidence of intersex fish in Seine-Maritime and Sussex regions. ANALUSIS 28:801–806
Mortensen GK, Main KM, Andersson AM, Leffers H, Shakkebaek NE (2005) Determination of phthalate monoesters in human milk, consumer milk, and infant formula by tandem mass spectrometry (LC-MS/MS). Anal Bioanal Chem 382:1084–1092
Silva MJ, Barr DB, Reidy JA, Kato K, Malek NA, Hodge CC (2003) Glucuronidation patterns of common urinary and serum monoester phthalate metabolites. Arch Toxicol 77:561–567
Silva MJ, Slakman AR, Reidy JA, Preau JL Jr, Herbert AR, Samandra E, Needham LL, Calafat AM (2004) Analysis of human urine for fifteen phthalate metabolites using automated solid-phase extraction. Chromatogr B 805:161–167
Silva MJ, Samandar E, Reidy JA, Hauser R, Needham LL, Calafat AM (2007) Metabolite profiles of di-n-butyl phthalate in humans and rats. Environ Sci Technol 41:7576–7580
Sircar D, Albazi SJ, Atallah Y, Pizzi W (2008) Validation and Application of an HPLC Method for determination of di (2-ethylhexyl) phthalate and mono (2-ethylhexyl) phthalate in liver samples. J Chromatogr Sci 46:627–631
Staples CA, Peterson DR, Parkerton TF, Adam WJ (1997) The Environmental fate of phthalates esters. A literature review. Chemosphere 35:667–749
Takatori S, Kitagawa Y, Kitagawa M, Nakazawa H, Hori S (2004) Determination of di(2-ethylhexyl)phthalate and mono(2-ethylhexyl)phthalate in human serum using liquid chromatography–tandem mass spectrometry. J Chromatogr B 804:397–401
Teil MJ, Tlili K, Blanchard M, Chevreuil M, Alliot F, Labadie P (2012) Occurrence of polybrominated diphenyl ethers, polychlorinated biphenyls, and phthalates in freshwater fish from the Orge River (Ile-de France). Arch Environ Contam Toxicol 63:101–113
Ye T, Kang M, Huang K, Fang C, Chen Y, Shen H, Dong S (2014) Exposure to DEHP and MEHP from hatching to adulthood causes reproductive dysfunction and endocrine disruption in marine medaka (Orysias melastigma). Aquat Toxicol 146:115–126
Acknowledgments
This work was supported by the PIREN-SEINE Research Programme. The French National Agency for Water and Aquatic Environments (ONEMA) provided assistance for electric fishing. We thank Catherine Bourges and Annie Desportes for their technical assistance.
Author information
Authors and Affiliations
Corresponding author
Additional information
Responsible editor: Roland Kallenborn
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(DOCX 43 kb)
Rights and permissions
About this article
Cite this article
Valton, A.S., Serre-Dargnat, C., Blanchard, M. et al. Determination of phthalates and their by-products in tissues of roach (Rutilus rutilus) from the Orge river (France). Environ Sci Pollut Res 21, 12723–12730 (2014). https://doi.org/10.1007/s11356-014-3213-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-014-3213-0