Diastereoisomer- and enantiomer-specific profiles of hexabromocyclododecane in the sediment of Dongjiang River, South China

Environmental Chemistry

Volumn 8, Issue 6, 2011, Pages 561-568

  Zhang, Xian ^a   Zhang, Dandan ^a,b   Luo, Zhuanxi ^a   Lin, Lifeng ^a   Yan, Changzhou ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

distribution; hexabromocyclododecanes; occurrence

Indexed keywords

BIODEGRADATION; BIOTRANSFORMATION; BROMINE COMPOUND; CONCENTRATION (COMPOSITION); DISCHARGE; FLUVIAL DEPOSIT; MICROBIAL ACTIVITY; ORGANOHALOGEN; POINT SOURCE; SEDIMENT CHEMISTRY;

CHINA; DONG RIVER; GUANGDONG;

EID: 82155188482     PISSN: 14482517     EISSN: None     Source Type: Journal    
DOI: 10.1071/EN10136     Document Type: Article

References (46)

1. C. De Wit, An overview of brominated flame retardants in the environment. Chemosphere 2002, 46, 583. doi:10.1016/S0045-6535 (01)00225-9
2. A. Covaci, A. C. Gerecke, R. J. Law, S. Voorspoels, K. Kohler, N. V. Heeb, H. Leslie, C. R. Allchin, J. De Boer, Hexabromocyclododecanes (HBCDs) in the environment and humans: A review. Environ. Sci. Technol. 2006, 40, 3679. doi:10.1021/ES0602492 (Pubitemid 43902361)
3. J. Arnot, L. McCarty, J. Armitage, L. Toose-Reid, F. Wania, I. Cousins, An Evaluation of Hexabromocyclododecane (HBCD) for Persistent Organic Pollutant (POP) Properties and the Potential for Adverse Effects in the Environment. EU Risk Assessment Report 2009 (European Brominated Flame Retardant Industry Panel, EBFRIP). Available at http://www.unece.org/env/documents/2009/EB/wg5/wgsr45/ Informal%20docs/An%20evaluation%20of%20hexabromocyclododecane-Final%20report. pdf [Verified 9 October 2011].
4. C. H. Marvin, G. T. Tomy, M. Alaee, G. Maclnnis, Distribution of hexabromocyclododecane in Detroit River suspended sediments. Chemosphere 2006, 64, 268. doi:10.1016/J.CHEMOSPHERE.2005. 12.011
5. Z. Yu, L. Chen, B. Mai, M. Wu, G. Sheng, J. Fu, P. Peng, Diastereoisomer-and enantiomer-specific profiles of hexabromocyclododecane in the atmosphere of an Urban City in south China. Environ. Sci. Technol. 2008, 42, 3996. doi:10.1021/ES7027857 (Pubitemid 351770053)
6. E. Eljarrat, P. Guerra, E. Martinez, M. Farre, J. G. Alvarez, M. Opezteijon, D. Barcelo, Hexabromocyclododecane in human breast milk: Levels and enantiomeric patterns. Environ. Sci. Technol. 2009, 43, 1940. doi:10.1021/ES802919E
7. X. L. Zhang, F. Yang, C. Luo, S. Wen, X. Zhang, Y. Xu, Bioaccumulative characteristics of hexabromocyclododecanes in freshwater species from an electronic waste recycling area in China. Chemosphere 2009, 76, 1572. doi:10.1016/J.CHEMOSPHERE.2009.05.031
8. K. Kakimoto, K. Akutsu, Y. Konishi, Y. Tanaka, Time trend of hexabromocyclododecane in the breast milk of Japanese women Chemosphere 2008, 71, 1110. doi:10.1016/J.CHEMOSPHERE. 2007.10.035
9. D. Ueno, M. Alaee, C. Marvin, D. C. G. Muir, G. Macinnis, E. Reiner, P. Crozier, V. I. Furdui, A. Subramanian, G. Fillmann, P. K. S. Lam, G. J. Zheng, M. Muchtar, H. Razak, M. Prudente, K. Chung, S. Tanabe, Distribution and transportability of hexabromocyclododecane (HBCD) in the Asia-Pacific region using skipjack tuna as a bioindicator. Environ. Pollut. 2006, 144, 238. doi:10.1016/J.ENVPOL.2005.12.024 (Pubitemid 44307418)
10. T. Yamada-Okabe, H. Sakai, Y. Kashima, H. Yamada-Okabe, Modulation at a cellular level of the thyroid hormone receptor mediated gene expression by 1,2,5,6,9,10-hexabromocyclododecane (HBCD), 4,40-diiodobiphenyl (DIB), and nitrofen (NIP). Toxicol. Lett. 2005, 155, 127. doi:10.1016/J.TOXLET.2004.09.005 (Pubitemid 39600744)
11. P. Eriksson, C. Fischer, M. Wallin, E. Jakobsson, A. Fredriksson, Impaired behaviour, learning and memory, in adult mice neonatally exposed to hexabromocyclododecane (HBCDD). Environ. Toxicol. Pharmacol. 2006, 21, 317. doi:10.1016/J.ETAP.2005.10.001
12. Candidate list of substances of very high concern for authorisation 2008 (European Chemicals Agency: Finland.) Available at http://echa.europa.eu/chem- data/authorisation-process/candidate-list-table-en.asp [Verified 21 October 2011].
13. R. J. Law, M. Kohler, N. V. Heeb, A. C. Gerecke, P. Schmid, S. Voorspoels, A. Covaci, G. Becher, K. Janák, C. Thomsen, Hexabromocyclododecane challenges scientists and regulators. Environ. Sci. Technol. 2005, 39, 281A. doi:10.1021/ES053302F
14. K. Law, V. P. Palace, T. Halldorson, R. Danell, K. Wautier, B. Evans, M. Alaee, C. Marvin, G. T. Tomy, Dietary accumulation of hexabromocyclododecane diastereoisomers in juvenile rainbow trout (Oncorhynchus mykiss) I: Bioaccumulation parameters and evidence of bioisomerization. Environ. Toxicol. Chem. 2006, 25, 1757. doi:10.1897/05-445R.1 (Pubitemid 44669845)
15. R. Köppen, R. Becker, C. Jung, I. Nehls, On the thermally induced isomerisation of hexabromocyclododecane stereoisomers. Chemosphere 2008, 71, 656. doi:10.1016/J.CHEMOSPHERE.2007.11.009
16. X. L. Zhang, F. Yang, C. Xu, W. Liu, S. Wen, Y. Xu, Cytotoxicity evaluation of three pairs of hexabromocyclododecane (HBCD) enantiomers on Hep G2 cell. Toxicol. In Vitro 2008, 22, 1520. doi:10.1016/J.TIV.2008.05.006
17. K. Wiberg, Enantiospecific Analysis and Environmental Behavior of Chiral Persistent Organic Pollutants 2001, Ph.D. Thesis, Umeå University, Sweden.
18. F. Wong, M. Robson, M. L. Diamond, S. Harrad, J. Truong, Concentrations and chiral signatures of POPs in soils and sediments: A comparative urban versus rural study in Canada and UK. Chemosphere 2009, 74, 404. doi:10.1016/J. CHEMOSPHERE.2008.09.051
19. K. Janák, A. Covaci, S. Voorspoels, G. Becher, Hexabromocyclododecane in marine species from the western Scheldt Estuary: Diastereomer-and enantiomer-specific accumulation. Environ. Sci. Technol. 2005, 39, 1987. doi:10.1021/ES0484909 (Pubitemid 40490281)
20. B. Mai, S. Chen, X. Luo, L. Chen, Q. Yang, G. Sheng, P. Peng, J. Fu, E. Zeng, Distribution of polybrominated diphenyl ethers in sediments of the Pearl River Delta and adjacent South China Sea. Environ. Sci. Technol. 2005, 39, 3521. doi:10.1021/ES048083X (Pubitemid 40705473)
21. P. Guerra, E. Eljarrat, D. Barcelóa, Enantiomeric specific determination of hexabromocyclododecane by liquid chromatographyquadrupole linear ion trap mass spectrometry in sediment samples. J. Chromatogr. A 2008, 1203, 81. doi:10.1016/J.CHROMA.2008. 07.027
22. C. H. Marvin, G. Maclnnis, M. Alaee, G. Arsenault, G. T. Tomy, Factors influencing enantiomeric fractions of hexabromocyclododecane measured using liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 1925. doi:10.1002/RCM.3040 (Pubitemid 46953555)
23. P. N. Froelich, Analysis of organic carbon in marine sediments. Limnol. Oceanogr. 1980, 25, 564. doi:10.4319/LO.1980.25.3.0564
24. HBCD: Hexabromocyclododecane 2009 (Bromine Science and Environmental Forum, BSEF: Brussels, Belgium). Available at http://www.bsef.com/uploads/ Documents/documents/HBCD-factsheet.pdf [Verified 21 October 2011].
25. S. Morris, C. R. Allchin, B. N. Zegers, J. H. Haftka, J. P. Boon, C. Belpaire, P. E. G. Leonards, S. P. J. Van Leeuwen, J. De Boer, Distribution and fate of HBCD and TBBPA brominated flame retardants in North Sea estuaries and aquatic food webs. Environ. Sci. Technol. 2004, 38, 5497. doi:10.1021/ES049640I (Pubitemid 39447175)
26. E. Eljarrat, A. De La Cal, D. Raldua, C. Duran, D. Barcelo, Occurrence and bioavailability of polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from the Cinca River, a tributary of the Ebro River (Spain). Environ. Sci. Technol. 2004, 38, 2603. doi:10.1021/ES0301424 (Pubitemid 38579860)
27. M. Remberger, J. Sternbeck, A. Palm, L. Kaj, K. Strömberg, E. Brorström-Lunde'n, The environmental occurrence of hexabromocyclododecane in Sweden. Chemosphere 2004, 54, 9. doi:10.1016/S0045-6535(03)00758-6 (Pubitemid 38128285)
28. S. Kemmlein, D. Herzke, R. Law, BFR-governmental testing programme. Environ. Int. 2003, 29, 781. doi:10.1016/S0160-4120 (03)00112-0
29. K. Janák, U. Sellström, A. K. Johansson, G. Becher, C. De Wit, P. Lindberg, B. Helander, Enantiomer-specific accumulation pattern of hexabromocyclododecane in eggs of predatory birds breeding in Sweden. Organohalogen Compd. 2005, 67, 204.
30. J. I. Drever, The Geochemistry of Natural Waters 1997 (Prentice-Hall, Inc.: Upper Saddle River, NJ).
31. M. Haukås, K. Hylland, J. A. Berge, T. Nygård, E. Mariussen, Spatial diastereomer patterns of hexabromocyclododecane (HBCD) in a Norwegian fjord. Sci. Total Environ. 2009, 407, 5907. doi:10.1016/J.SCITOTENV.2009.08.024
32. N. V. Heeb, W. B. Schweizer, P. Mattrel, R. Haag, A. C. Gerecke, P. Schmid, M. Zennegg, H. Vonmont, Regio-and stereoselective isomerization of hexabromocyclododecanes (HBCDs): Kinetics and mechanism of g-to a-HBCD isomerization. Chemosphere 2008, 73, 1201. doi:10.1016/J.CHEMOSPHERE.2008.07.045
33. 14 hexabromocyclododecane in wastewater sludge and freshwater aquatic sediment. Environ. Sci. Technol. 2006, 40, 5395. doi:10.1021/ES060009M (Pubitemid 44373104)
34. T. V. Padma, R. M. Dickhut, H. Ducklow, Variations in a-hexachlorocyclohexane enantiomer ratios in relation to microbial activity in a temperate estuary. Environ. Toxicol. Chem. 2003, 22, 1421. doi:10.1002/ETC. 5620220702
35. M. Schlabach, E. Fjeld, A. Borgen, Brominated flame retardants in Drammen River and the Drammensfjord, Norway, in Proceedings of the Third International Workshop on Brominated Flame Retardants, 6-9 June 2004, Toronto, Canada 2004, pp. 147-150.
36. R. J. Law, D. Herzke, S. Harrad, S. Morris, P. Bersuder, C. R. Allchin, Levels and trends of HBCD and BDEs in the European and Asian environments, with some information for other BFRs. Chemosphere 2008, 73, 223. doi:10.1016/J. CHEMOSPHERE.2008.02.066
37. K. Janák, U. Sellström, A. K. Johansson, G. Becher, C. A. De Wit, P. Lindberg, B. Helander, Enantiomer-specific accumulation of hexabromocyclododecanes in eggs of predatory birds. Chemosphere 2008, 73, S193. doi:10.1016/J.CHEMOSPHERE.2007.03.077
38. K. Vorkamp, M. Thomsen, K. Falk, H. Leslie, S. Moller, P. B. Sorensen, Temporal development of brominated flame retardants in peregrine falcon (Falco peregrinus) eggs from South Greenland (1986-2003). Environ. Sci. Technol. 2005, 39, 8199. doi:10.1021/ES0508830 (Pubitemid 41572403)
39. G. T. Tomy, K. Pleskach, T. Oswald, T. Halldorson, P. A. Helm, G. MacInnis, C. H. Marvin, Enantioselective bioaccumulation of hexabromocyclododecane and congener-specific accumulation of brominated diphenyl ethers in an eastern Canadian Arctic marine food web. Environ. Sci. Technol. 2008, 42, 3634. doi:10.1021/ES703083Z (Pubitemid 351694072)
40. A. M. Peck, R. S. Pugh, A. Moors, M. B. Ellisor, B. J. Porter, P. R. Becker, J. R. Kucklick, Hexabromocyclododecane in white-sided dolphins: Temporal trend and stereoisomer distribution in tissues. Environ. Sci. Technol. 2008, 42, 2650. doi:10.1021/ES072052V (Pubitemid 351482944)
41. T. A. Müller, H. P. E. Kohler, Chirality of pollutants-effects on metabolism and fate. Appl. Microbiol. Biotechnol. 2004, 64, 300. doi:10.1007/S00253-003-1511-4 (Pubitemid 38626453)
42. H. Iwata, S. Tanabe, T. Iida, N. Baba, J. P. Ludwig, R. Tatsukawa, Enantioselective accumulation of a-hexachlorocyclohexane in northern fur seals and double-crested cormorants: Effects of biological and ecological factors in the higher trophic levels. Environ. Sci. Technol. 1998, 32, 2244. doi:10.1021/ES980115R (Pubitemid 28359860)
43. M. Schlabach, E. Fjeld, H. Gundersen, E. Mariussen, G. Kjellberg, E. Breivik, Pollution of Lake Mjøsa by brominated flame retardants. Organohalogen Compd. 2004, 66, 3730.
44. U. Sellström, A. Kierkegaard, C. deWit, B. Jansson, Polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from a Swedish river. Environ. Toxicol. Chem. 1998, 17, 1065. doi:10.1002/ETC.5620170612
45. C. H. Marvin, G. T. Tomy, M. Alaee, G. Maclnnis, Distribution of hexabromocyclododecane in Detroit River suspended sediments. Chemosphere 2006, 64, 268. doi:10.1016/J.CHEMOSPHERE.2005. 12.011
46. N. H. Minh, T. Isobe, D. Ueno, K. Matsumoto, M. Mine, N. Kajiwara, S. Takahashi, S. Tanabe, Spatial distribution and vertical profile of polybrominated diphenyl ethers and hexabromocyclododecanes in sediment core from Tokyo Bay, Japan. Environ. Pollut. 2007, 148, 409. doi:10.1016/J.ENVPOL.2006. 12.011 (Pubitemid 46830832)