Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania
Some methoxylated polybrominated diphenyl ethers (MeO-BDEs) are known halogenated natural products (HNPs) and are frequently detected in higher organisms of the marine environment. In this study we demonstrate that a prominent MeO-BDE, previously detected in marine mammals from Australia, is identic...
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Amer Chemical Soc
2005
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ftunivqespace:oai:espace.library.uq.edu.au:UQ:75463 2023-05-15T13:46:20+02:00 Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania Melcher, J Olbrich, D Marsh, G Nikiforov, V Gaus, C Gaul, S Vetter, W J Schnoor 2005-01-01 https://espace.library.uq.edu.au/view/UQ:75463 eng eng Amer Chemical Soc doi:10.1021/es051090g issn:0013-936X orcid:0000-0002-0585-8511 Engineering Environmental Environmental Sciences Polybrominated Diphenyl Ethers Halogenated Natural-products Naturally Produced Organohalogens Identification Chromatography Diversity Sponges Fish 321299 Public Health and Health Services not elsewhere classified C1 730210 Environmental health Journal Article 2005 ftunivqespace https://doi.org/10.1021/es051090g 2020-12-22T00:29:19Z Some methoxylated polybrominated diphenyl ethers (MeO-BDEs) are known halogenated natural products (HNPs) and are frequently detected in higher organisms of the marine environment. In this study we demonstrate that a prominent MeO-BDE, previously detected in marine mammals from Australia, is identical to 3,5-dibromo-2-(2',4'-dibromo)phenoxyanisole(BC-3,6-MeO-BDE47). Up to 1.9mg/ kg of 6-MeO-BDE 47 was present in cetaceans from Australia, 0.2-0.3 mg/kg in two crocodile eggs from Australia, but concentrations of 1 or 2 orders of magnitude lower were found in shark liver oil from New Zealand and in marine mammals from Africa and the Antarctic. Concentrations of 6-MeO-BDE47 in samples from Australia were in the same range as anthropogenic pollutants such as PCB 153 and p,p'-DDE. Along with 6-MeO-BDE 47 and the known HNP 4,6-dibromo-2-(2',4'-dibromo)phenoxyanisole (BC-2,2'-MeO-BDE 68), several tribromophenoxyanisoles (MeO-triBDE) were present in tissue of Australian cetaceans. To determine their structure, abiotic debromination experiments were performed using 6-MeO-BDE 47 and 2'-MeO-BDE 68 and superreduced di cyanocobalamine. These experiments resulted in formation of eight MeO-triBDEs, all of which were detected in the cetacean samples. Five of these eight MeO-triBDEs could be identified based on two standard compounds as well as gas chromatographic and mass spectrometric features. It was also shown that the first eluting isomer (compound 1), 6-MeO-BDE 17 (compound 2), and 2-MeO-BDE 39 (compound 5) were the most prominent MeO-triBDEs in the Australian cetacean samples. The concentrations of the MeO-triBDEs in two cetacean samples were 0.20 and 0.36 mg/kg, respectively. Although the reductive debromination with dicyanocobalamine resulted in a different congener pattern than was found in the marine mammals, it could not be excluded that the tribromo congeners of 6-MeO-BDE 47 and 2'-MeO-BDE 68 in the samples were metabolites of the latter. Article in Journal/Newspaper Antarc* Antarctic The University of Queensland: UQ eSpace Antarctic The Antarctic New Zealand Environmental Science & Technology 39 20 7784 7789 |
institution |
Open Polar |
collection |
The University of Queensland: UQ eSpace |
op_collection_id |
ftunivqespace |
language |
English |
topic |
Engineering Environmental Environmental Sciences Polybrominated Diphenyl Ethers Halogenated Natural-products Naturally Produced Organohalogens Identification Chromatography Diversity Sponges Fish 321299 Public Health and Health Services not elsewhere classified C1 730210 Environmental health |
spellingShingle |
Engineering Environmental Environmental Sciences Polybrominated Diphenyl Ethers Halogenated Natural-products Naturally Produced Organohalogens Identification Chromatography Diversity Sponges Fish 321299 Public Health and Health Services not elsewhere classified C1 730210 Environmental health Melcher, J Olbrich, D Marsh, G Nikiforov, V Gaus, C Gaul, S Vetter, W Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania |
topic_facet |
Engineering Environmental Environmental Sciences Polybrominated Diphenyl Ethers Halogenated Natural-products Naturally Produced Organohalogens Identification Chromatography Diversity Sponges Fish 321299 Public Health and Health Services not elsewhere classified C1 730210 Environmental health |
description |
Some methoxylated polybrominated diphenyl ethers (MeO-BDEs) are known halogenated natural products (HNPs) and are frequently detected in higher organisms of the marine environment. In this study we demonstrate that a prominent MeO-BDE, previously detected in marine mammals from Australia, is identical to 3,5-dibromo-2-(2',4'-dibromo)phenoxyanisole(BC-3,6-MeO-BDE47). Up to 1.9mg/ kg of 6-MeO-BDE 47 was present in cetaceans from Australia, 0.2-0.3 mg/kg in two crocodile eggs from Australia, but concentrations of 1 or 2 orders of magnitude lower were found in shark liver oil from New Zealand and in marine mammals from Africa and the Antarctic. Concentrations of 6-MeO-BDE47 in samples from Australia were in the same range as anthropogenic pollutants such as PCB 153 and p,p'-DDE. Along with 6-MeO-BDE 47 and the known HNP 4,6-dibromo-2-(2',4'-dibromo)phenoxyanisole (BC-2,2'-MeO-BDE 68), several tribromophenoxyanisoles (MeO-triBDE) were present in tissue of Australian cetaceans. To determine their structure, abiotic debromination experiments were performed using 6-MeO-BDE 47 and 2'-MeO-BDE 68 and superreduced di cyanocobalamine. These experiments resulted in formation of eight MeO-triBDEs, all of which were detected in the cetacean samples. Five of these eight MeO-triBDEs could be identified based on two standard compounds as well as gas chromatographic and mass spectrometric features. It was also shown that the first eluting isomer (compound 1), 6-MeO-BDE 17 (compound 2), and 2-MeO-BDE 39 (compound 5) were the most prominent MeO-triBDEs in the Australian cetacean samples. The concentrations of the MeO-triBDEs in two cetacean samples were 0.20 and 0.36 mg/kg, respectively. Although the reductive debromination with dicyanocobalamine resulted in a different congener pattern than was found in the marine mammals, it could not be excluded that the tribromo congeners of 6-MeO-BDE 47 and 2'-MeO-BDE 68 in the samples were metabolites of the latter. |
author2 |
J Schnoor |
format |
Article in Journal/Newspaper |
author |
Melcher, J Olbrich, D Marsh, G Nikiforov, V Gaus, C Gaul, S Vetter, W |
author_facet |
Melcher, J Olbrich, D Marsh, G Nikiforov, V Gaus, C Gaul, S Vetter, W |
author_sort |
Melcher, J |
title |
Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania |
title_short |
Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania |
title_full |
Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania |
title_fullStr |
Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania |
title_full_unstemmed |
Tetra- and tribromopbenoxyanisoles in Marine Samples from Oceania |
title_sort |
tetra- and tribromopbenoxyanisoles in marine samples from oceania |
publisher |
Amer Chemical Soc |
publishDate |
2005 |
url |
https://espace.library.uq.edu.au/view/UQ:75463 |
geographic |
Antarctic The Antarctic New Zealand |
geographic_facet |
Antarctic The Antarctic New Zealand |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_relation |
doi:10.1021/es051090g issn:0013-936X orcid:0000-0002-0585-8511 |
op_doi |
https://doi.org/10.1021/es051090g |
container_title |
Environmental Science & Technology |
container_volume |
39 |
container_issue |
20 |
container_start_page |
7784 |
op_container_end_page |
7789 |
_version_ |
1766240642664497152 |