Abstract
Polyhalogenated carbazoles (PHCZs) have recently emerged as a group of halogenated pollutants with broad occurrences and bioaccumulation potential in aquatic systems. However, investigations on their occurrences in coastal waters remain very limited. In the present study we investigated PHCZs in surface sediment collected from 29 sites in Sanmen Bay, East China Sea. The results demonstrated a universal presence of PHCZs in sediment, with concentrations of ∑PHCZs (including all congeners) ranging from 7.7 to 17.5 ng/g dry weight (median: 11.3 ng/g dw). The PHCZ congener composition profile revealed a dominance of 3,6-dichlorocarbazole (36-CCZ) with comparable concentration with that of carbazole. Given that PHCZs are widely distributed in Sanmen Bay sediment and their concentrations rivaled other well-known persistent organic pollutants in the same area, this group of halogenated pollutants merits additional investigations of their potential risks to the studied aquatic system, as well as other important watersheds.
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References
Bonesi SM, Erra-Balsells R (1997) On the synthesis and isolation of chlorocarbazoles obtained by chlorination of carbazoles. J Heterocycl Chem 34:877–889
Castorena G, Mugica V, Le Borgne S, Acuña M, Bustos-Jaimes I, Aburto J (2006) Carbazole biodegradation in gas oil/water biphasic media by a new isolated bacterium Burkholderia sp. strain IMP5GC. J Appl Microbiol 100:739–745
Chen WL, Xie ZY, Wolschke H, Gandrass J, Kötke D, Winkelmann M, Ebinghaus R (2016) Quantitative determination of ultra-trace carbazoles in sediments in the coastal environment. Chemosphere 150:586–595
Chen YQ, Lin KD, Chen D, Wang K, Zhou WX, Wu Y, Huang XW (2017) Formation of environmentally relevant polyhalogenated carbazoles from chloroperoxidase-catalyzed halogenation of carbazole. Environ pollut 232:264–273
Clegg H, Wilkes H, Horsfield B (1997) Carbazole distributions in carbonate and clastic source rocks. Geochim Cosmochimi Acta 61:5335–5345
Fang ML, Guo JH, Chen D, Li A, Hinton DE, Dong W (2016) Halogenated carbazoles induce cardiotoxicity in developing zebrafish (Danio rerio) embryos. Environ Toxicol Chem 35:2523–2529
Fromme H, Mi WY, Lahrz T, Kraft M, Aschenbrenner B, Bruessow B, Ebinghaus R, Xie ZY, Fembacher L (2018) Occurrence of carbazoles in dust and air samples from different locations in Germany. Sci Total Environ 610–611:412–418
Grigoriadou A, Schwarzbauer J (2011) Non-target screening of organic contaminants in sediments from the industrial coastal area of Kavala City (NE Greece). Water Air Soil Poll 214:623–643
Guo JH, Chen D, Potter D, Rockne KJ, Sturchio NC, Giesy JP, Li A (2014) Polyhalogenated carbazoles in sediments of Lake Michigan: a new discovery. Environ Sci Technol 48:12807–12815
Guo JH, Li ZN, Ranasinghe P, Bonina S, Hosseini S, Corcoran MB, Smalley C, Rockne KJ, Sturchio NC, Giesy JP, Li A (2017) Spatial and temporal trends of polyhalogenated carbazoles in sediments of upper Great Lakes: insights into their origin. Environ Sci Technol 51:89–97
Han WL, Feng JL, Gu ZP, Chen DH, Wu MH, Fu JM (2009) Polybrominated diphenyl ethers in the atmosphere of Taizhou, a major E-waste dismantling area in China. B Environ Contam Tox 83:783–788
Heim S, Schwaubauer J, Kronimus A, Littke R, Woda C, Mangini A (2004) Geochronology of anthropogenic pollutants in riparian wetland sediments of the Lippe River (Germany). Org Geochem 35:1409–1425
Ji CY, Yan L, Chen YC, Yue SQ, Dong QX, Chen JF, Zhao MR (2019) Evaluation of the developmental toxicity of 2,7-dibromocarbazole to zebrafish based on transcriptomics assay. J Hazard Mater 368:514–522
Jiang JQ, Zhao HX, Sun SB, Wang YT, Liu SS, Xie Q, Li XK (2018) Occurrence and profiles of halogenated phenols, polybrominated diphenyl ethers and hydroxylated polybrominated diphenyl ethers in the effluents of waste water treatment plants around Huang-Bo Sea, North China. Sci Total Environ 622:1–7
Kronimus A, Schwarzbauer J, Dsikowitzky L, Heim S, Littke R (2004) Anthropogenic organic contaminants in sediments of the Lippe river, Germany. Water Res 38:3473–3484
Li CS, Suzuki K (2010) Resources, properties and utilization of tar. Resour Conserv Recy 54:905–915
Liu ZS, Wang CS, Zhang ZN, Liu CG, Yang GM (2006) Seasonal dynamics of zooplankton and grazing impact of microzooplankton on phytoplankton in Sanmen Bay, China. Acta Ecol Sin 26:3931–3940
Liu Q, Liao YB, Shou L (2018) Concentration and potential health risk of heavy metals in seafoods collected from Sanmen Bay and its adjacent areas, China. Mar Pollut Bull 131:356–364
Moon HB, Kannan K, Choi M, Choi HG (2007) Polybrominated diphenyl ethers (PBDEs) in marine sediments from industrialized bays of Korea. Mar Pollut Bull 54:1402–1412
Morin JF, Leclerc M, Adès D, Siove A (2005) Polycarbazoles: 25 years of progress. Macromol Rapid Comm 26:761–778
Mumbo J, Lenoir D, Henkelmann B, Schramm KW (2013) Enzymatic synthesis of bromo- and chlorocarbazoles and elucidation of their structures by molecular modeling. Environ Sci Pollut Res 20:8996–9005
Mumbo J, Henkelmann B, Abdelaziz A, Pfister G, Nguyen N, Schroll R, Munch JC, Schramm KW (2014) Persistence and dioxin-like toxicity of carbazole and chlorocarbazoles in soil. Environ Sci Pollut Res 22:1–2
Mumbo J, Pandelova M, Mertes F, Henkelmann B, Bussian BM, Schramm KW (2016) The fingerprints of dioxin-like bromocarbazoles and chlorocarbazoles in selected forest soils in Germany. Chemosphere 162:64–72
Parette R, Mccrindle R, Mcmahon KS, Pena-Abaurrea M, Reiner E, Chittim B, Riddell N, Voss G, Dorman FL, Pearson WN (2015) Halogenated indigo dyes: a likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment. Chemosphere 127:18–26
Pena-Abaurrea M, Robson M, Chaudhuri S, Riddell N, Mccrindle R, Chittim B, Parette R, Jin UH, Safe S, Poirier D, Ruffolo R, Dyer R, Fletcher R, Helm PA, Reiner EJ (2016) Environmental levels and toxicological potencies of a novel mixed halogenated carbazole. EMCs 2:166–172
Peng H, Chen CL, Saunders DMV, Sun JX, Tang S, Codling G, Hecker M, Wiseman S, Jones PD, Li A, Rockne KJ, Giesy JP (2015) Untargeted identification of organo-bromine compounds in lake sediments by ultrahigh-resolution mass spectrometry with the data-independent precursor isolation and characteristic fragment method. Anal Chem 87:10237–10246
Peng H, Chen CL, Cantin J, Saunders DMV, Sun JX, Tang S, Codling G, Hecker M, Wiseman S, Jones PD, Li A, Rockne KJ, Sturchio NC, Giesy JP (2016) Untargeted screening and distribution of organo-bromine compounds in sediments of take Michigan. Environ Sci Technol 50:321–330
Pereira WE, Rostad CE, Taylor HE (1980) Mount St. Helens, Washington, 1980 volcanic eruption: characterization of organic compounds in ash samples. Geophys Res Lett 7:953–954
Riddell N, Jin UH, Safe S, Cheng YT, Chittim B, Konstantinov A, Parette R, Pena-Abaurrea M, Reiner EJ, Poirier D, Stefanac T, McAlees AJ, McCrindle R (2015) Characterization and biological potency of mono- to tetra-halogenated carbazoles. Environ Sci Technol 49:10658–10666
Takasuga T, Takemor H, Yamamoto T, Higashino K, Sasaki Y, Weber R (2009) The fingerprint of chlorinated aromatic compounds in contaminated sites from chloralkali process and a historic chlorine production using GC-HR-TOF-MS screening. Organohalogen Compd 71:002224–002229
Tröbs L, Henkelmann B, Lenoir D, Reischl A, Schramm KW (2011) Degradative fate of 3-chlorocarbazole and 3,6-dichlorocarbazole in soil. Environ Sci Pollut Res 18:547
Wang JX, Lin ZK, Lin KF, Wang CY, Zhang W, Cui CY, Lin JD, Dong QX, Huang CJ (2011) Polybrominated diphenyl ethers in water, sediment, soil, and biological samples from different industrial areas in Zhejiang, China. J Hazard Mater 197:211–219
Wu Y, Moore J, Guo JH, Li A, Grasman K, Choy S, Chen D (2016a) Multi-residue determination of polyhalogenated carbazoles in aquatic sediments. J Chromatogr A 1434:111–118
Wu Y, Qiu YL, Tan HL, Chen D (2016b) Polyhalogenated carbazoles in sediments from Lake Tai (China): distribution, congener composition, and toxic equivalent evaluation. Environ pollut 220:142–149
Wu Y, Tan HL, Sutton R, Chen D (2017) From sediment to top predators: broad exposure of polyhalogenated carbazoles in San Francisco Bay (U.S.A.). Environ Sci Technol 51:2038–2046
Wu Y, Tan HL, Zhou CL, Crimmins BS, Holsen TM, Chen D (2018) Bioaccumulation and spatiotemporal trends of polyhalogenated carbazoles in Great Lakes Fish from 2004 to 2016. Environ Sci Technol 52:4536–4545
Xia XM (2011) Stability of tidal inlet in the Sanmen Bay. Dissertation, Zhejiang University
Xu XF, He QQ, Song D, Yang ZL, Yu LL (2018) Comparison of hydrodynamic influence between different types of bay reclamations. J Hydrodyn 30:694–700
Yang HY, Xue B, Yu P, Zhou SS, Liu WP (2010) Residues and enantiomeric profiling of organochlorine pesticides in sediments from Yueqing Bay and Sanmen Bay, East China Sea. Chemosphere 80:652–659
Yang HY, Xue B, Jin LX, Zhou SS, Liu WP (2011) Polychlorinated biphenyls in surface sediments of Yueqing Bay, Xiangshan Bay, and Sanmen Bay in East China Sea. Chemosphere 83:137–143
Yao YM, Huang XQ (2015) Research on marine environmental capacity and total pollutant control in Sanmen Bay. Ocean press, Lancing, pp 86–89 (in Chinese)
Zhang LZ, Zhang M, Gao J, Xu DM, Zhou SX, Wang YL (2018) Efficient extraction of neutral heterocyclic nitrogen compounds from coal tar via ionic liquids and its mechanism analysis. Energ fuel 32:9358–9370
Zhou SS, Fu J, He H, Fu JJ, Tang QZ, Dong MF, Pan YQ, Li A, Liu WP, Zhang LM (2017) Spatial distribution and implications to sources of halogenated flame retardants in riverine sediments of Taizhou, an intense e-waste recycling area in eastern China. Chemosphere 184:1202–1208
Zhu LY, Hites RA (2005) Identification of brominated carbazoles in sediment cores from Lake Michigan. Environ Sci Technol 39:9446–9451
Acknowledgements
This present study was financially supported by the National Key R&D Program of China (No. 2017YFC1404300) and the National Natural Science Foundation of China (No. 41676144). We also thank the families participating in this project.
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Qiu, Y., Liu, K., Zhou, S. et al. Polyhalogenated Carbazoles in Surface Sediment from Sanmen Bay, East China Sea: Spatial Distribution and Congener Profile. Bull Environ Contam Toxicol 103, 41–47 (2019). https://doi.org/10.1007/s00128-019-02637-7
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DOI: https://doi.org/10.1007/s00128-019-02637-7