Hydroxylated and methoxylated brominated diphenyl ethers in the red algae Ceramium tenuicorne and blue mussels from the Baltic Sea

Environmental Science and Technology

Volumn 39, Issue 9, 2005, Pages 2990-2997

  Malmvärn, Anna ^a   Marsh, Göran ^a   Kautsky, Lena ^a   Athanasiadou, Maria ^a   Bergman, Åke ^a   Asplund, Lillemor ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BIODIVERSITY; CHLORINATION; ETHERS; HYDROXYLATION; IONIZATION; METABOLITES; WATER POLLUTION;

BROMINATED DIPHENYL ETHERS; ELECTRON CAPTURE NEGATIVE IONIZATION (ECNI); METHOXYLATED POLYBROMINATED DIPHENYL ETHERS (MEO-PBDE); WILDLIFE;

ALGAE;

HYDROXYLATED POLYBROMINATED DIPHENYL ETHER; METHOXYLATED POLYBROMINATED DIPHENYL ETHER; POLYBROMINATED BIPHENYL; UNCLASSIFIED DRUG;

BIOACCUMULATION; BROMINE; ETHER; MARINE POLLUTION;

ARTICLE; BALTIC SEA; BIOACCUMULATION; CHEMICAL ANALYSIS; ELECTRON CAPTURE DETECTION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MUSSEL; NONHUMAN; RED ALGA; SEA POLLUTION;

ALGAE, RED; ANIMALS; BALTIC STATES; BIVALVIA; ENVIRONMENTAL MONITORING; POLYBROMINATED BIPHENYLS; WATER POLLUTANTS, CHEMICAL;

ATLANTIC OCEAN; BALTIC SEA; OCEANIC REGIONS; WORLD;

ALGAE; CERAMIUM TENUICORNE; MYTILUS EDULIS; RHODOPHYTA;

EID: 18344392938     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es0482886     Document Type: Article

References (55)

1. Elmgren, R. Man's Impact on the Ecosystem of the Baltic Sea: Energy Flows Today and at the Turn of the Century. Ambio 1989, 18, 322-332.
2. Hänninen, J.; Vuorinen, I.; Helminen, H.; Kirkkala, T.; Lehtilä, K. Trends and Gradients in Nutrient Concentrations and Loading in the Archipelago Sea, Northern Baltic, in 1970-1997. Estuarine, Coastal Shelf Sci. 2000, 50, 153-171.
3. Bignert, A.; Olsson, M.; Persson, W.; Jensen, S.; Zakrisson, S.; Litzén, K.; Eriksson, U.; Häggberg, L.; Alsberg, T. Temporal Trends of Organochlorines in Northern Europe, 1967-1995. Relation to Global Fractionation, Leakage from Sediments and International Measures. Environ. Pollut. 1998, 99, 177-198.
4. Helander, B.; Olsson, A.; Bignert, A.; Asplund, L.; Litzén, K. The Role of DDE, PCB, Coplanar PCB and Eggshell Parameters for Reproduction in the White-Tailed Sea Eagle (Haliaeetus albicilla) in Sweden. Ambio 2002, 31, 386-403.
5. de Wit, C. An Overview of Brominated Flame Retardants in the Environment. Chemosphere 2002, 46, 583-624.
6. Haglund, P. S.; Zook, D. R.; Hu, J. Identification and Quantification of Polybrominated Diphenyl Ethers and Methoxy - Polybrominated Diphenyl Ethers in Baltic Biota. Environ. Sci. Technol. 1997, 31, 3281-3287.
7. Asplund, L. T.; Athanasiadou, M.; Sjödin, A.; Bergman, Å.; Börjesson, H. Organohalogen Substances in Muscle, Egg and Blood From Healthy Baltic Salmon (Salmon Salar) and Baltic Salmon That Produced Offspring With the M74 Syndrome. Ambio 1999, 28, 67-76.
8. Marsh, G.; Athanasiadou, M.; Bergman, Å.; Asplund, L. Identification of Hydroxylated and Methoxylated Polybrominated Diphenyl Ethers in Baltic Sea Salmon (Salmo Salar) Blood. Environ. Sci. Technol. 2004, 38, 10-18.
9. Sinkkonen, S.; Rantalainen, A.-L.; Paasivirta, J.; Lahtiperä, M. Polybrominated Methoxy Diphenyl Ethers (MeO PBDEs) in Fish and Guillemot of Baltic, Atlantic and Arctic Environments. Chemosphere 2004, 56, 767-775.
10. Örn, U.; Klasson Wehler, E. Metabolism of 2,2′,4,4′- Tetrabromodiphenyl Ether in Rat and Mouse. Xenobiotica 1998, 28, 199-211.
11. Hakk, H.; Larsen, G.; Klasson Wehler, E. Tissue Disposition, Excretion and Metabolism of 2,2′,4,4′,5-Pentabromodiphenyl Ether (BDE-99) in the Male Sprague - Dawley Rat. Xenobiotica 2002, 32, 369-382.
12. Mörck, A.; Hakk, H.; Örn, U.; Klasson Wehler, E. Decabromodiphenyl Ether in the Rat: Absorption, Distribution, Metabolism, and Excretion. Drug Metab. Dispos. 2003, 31, 900-907.
13. 14C] diphenyl Ether in Pike (Esox lucius) after Dietary Exposure. Organohalogen Compd. 2001, 52, 58-61.
14. Letcher, R. J.; D'Sa, I.; Valters, K.; Marsh, G.; Li, H.; Bennett, E.; Alaee, M. Polybrominated Diphenyl Ethers and Hydroxylated and Methoxylated Analogues in Detroit River Fish. Organohalogen Compd. 2003, 61, 29-32.
15. Gribble, G. W. The Natural Production of Organobromine Compounds. Environ. Sci. Pollut. Res. 2000, 7, 37-49.
16. Faulkner, D. J. Marine Natural Products. Nat. Prod. Rep. 2001, 18, 1-49.
17. Faulkner, D. J. Marine Natural Products. Nat. Prod. Rep. 2002, 19, 1-48.
18. Anjaneyulu, V.; Nageswara Rao, K.; Radhika, P.; Muralikrishna, M. A New Tetrabromodiphenyl Ether From the Sponge Dysidea herbacea of the Indian Ocean. Indian J. Chem. 1996, 35B, 89-90.
19. Handayani, D.; Edrada, R. A.; Proksch, P.; Wray, V.; Witte, L.; Van Soest, R. W. M.; Kunzmann, A.; Soedarsono, Four New Bioactive Polybrominated Diphenyl Ethers of the Sponge Dysidea herbacea from West Sumatra, Indonesia. J. Nat. Prod. 1997, 60, 1313-1316.
20. Kuniyoshi, M.; Yamada, K.; Higa, T. A Biologically Active Diphenyl Ether from the Green Alga Cladophora fascicularis. Experientia 1985, 41, 523-524.
21. Pedersén, M.; Saenger, P.; Fries, N. Simple Brominated Phenols in Red Algae. Phytochemistry 1974, 13, 2273-2279.
22. Pedersén, M. Bromochlorophenols and Brominated Diphenylmethane in Red Algae. Phytochemistry 1978, 17, 291-293.
23. Pedersén, M. A Brominating and Hydroxylating Peroxidase from the Red Alga Cystoclonium purpureum. Physiol. Plant. 1976, 37, 6-11.
24. Vogel. Vogel's Elementary Practical Organic Chemistry 1: Preparations; Longman Inc.: New York, 1980; pp 267-268.
25. Örn, U.; Eriksson, L.; Jakobsson, E.; Bergman, Å. Synthesis and Characterization of Polybrominated Diphenyl Ethers - Unlabeled and Radiolabeled Tetra-, Penta- and Hexabromodiphenyl Ethers. Acta Chem. Scand. 1996, 50, 802-807.
26. Marsh, G.; Stenutz, R.; Bergman, Å. Synthesis of Hydroxylated and Methoxylated Polybrominated Diphenyl Ethers - Natural Products and Potential Polybrominated Diphenyl Ether Metabolites. Eur. J. Org. Chem. 2003, 2566-2576.
27. Jensen, S.; Reutergårdh, L.; Jansson, B. Analytical Methods for Measuring Organochlorines and Methyl Mercury by Gas Chromatography. FAO Fish. Tech. Pap. 1983, 212, 21-33.
28. Hovander, L.; Athanasiadou, M.; Asplund, L.; Jensen, S.; Klasson-Wehler, E. Extraction and Cleanup Methods for Analysis of Phenolic and Neutral Organohalogens in Plasma. J. Anal. Toxicol. 2000, 24, 696-703.
29. Rosemarin, A.; Notini, M.; Söderström, M.; Jensen, S.; Landner, L. Fate and Effects of Pulp Mill Chlorophenolic 4,5,6-Trichloroguaiacol in a Model Brackish Water Ecosystem. Sci. Total Environ. 1990, 92, 69-89.
30. Malmvärn, A.; Kautsky, L.; Jensen, S.; Athanassiadis, I.; Asplund, L. Detection of a Possible Tribromodibenzo-p-dioxin in Blue Mussels (Mytilus edulis) from the Baltic Sea. Organohalogen Compd. 2003, 61, 143-146.
31. Campell, J.-A. B.; Griffin, D. A.; Deinzert, M. L. Electron Capture Negative Ion and Positive Ion Chemical Ionization Mass Spectrometry of Polychlorinated Penoxyanisols. Org. Mass Spectrom. 1985, 20, 122-133.
32. Olsson, A.; Ceder, K.; Bergman, Å.; Helander, B. Nestling Blood of the White-Tailed Sea Eagle (Haliaeetus albicilla) as an Indicator of Territorial Exposure to Organohalogen Compounds - An Evaluation. Environ. Sci. Technol. 2000, 34, 2733-2740.
33. Athanasiadou, M. Brominated Flame Retardants and Related Compounds in Baltic Sea Wildlife - Chemical Analytical Methodology and Assessment. Ph.D., Department of Environmental Chemistry, Stockholm University, 2003.
34. Padmakumar, K.; Ayyakkannu, K. Seasonal Variation of Antibacterial and Antifungal Activities of the Extracts of Marine Algae from Southern Coasts of India. Bot. Mar. 1997, 40, 507-515.
35. Zhao, J.; Fan, X.; Wang, S.; Li, S.; Shang, S.; Yang, Y.; Xu, N.; Lu, Y.; Shi, J. Bromophenol Derivatives from the Red Alga Rhodomela confervoides. J. Nat. Prod. 2004, 67, 1032-1035.
36. Carté, B.; Faulkner, D. J. Polybrominated Diphenyl Ethers from Dysidea herbacea, Dysidea chlorea and Phyllospongia foliascens. Tetrahedron 1981, 37, 2335-2339.
37. Fu X.; Schmitz, F. J.; Govindan, M.; Abbas, S. A. Enzyme Inhibitors: New and Known Polybrominated Phenols and Diphenyl Ethers from Four Indo-Pacific Dysidea Sponges. J. Nat. Prod. 1995, 58, 1384-1391.
38. 13C NMR Data for Some Brominated Diphenyl Ethers. J. Nat. Prod. 1996, 59, 1102-1103.
39. Capon, R.; Ghisalberti, E. L.; Jefferies, P. R.; Skelton, B. W.; White, A. H. Structural Studies of Halogenated Diphenyl Ethers from a Marine Sponge. J. Chem. Soc., Perkin Trans. 1 1980, 2464-2467.
40. Fu, X.; Hossain, M. B.; Schmitz, F. J.; van der Helm, D. Longithorones, Unique Prenylated Para- and Metacyclophane Type Quinones From the Tunicate Aplidium longithotax. J. Org. Chem. 1997, 62, 3810-3819.
41. Schumacher, R. W.; Davidson, B. S. Didemnolines A-D, New N9-Substituted B-Carbolines From the Marine Ascidian Didemnum Sp. Tetrahedron 1995, 51, 10125-10130.
42. Hovander, L.; Malmberg, T.; Athanasiadou, M.; Athanassiadis, I.; Rahm, S.; Bergman, Å.; Klasson Wehler, E. Identification of Hydroxylated PCB Metabolites and Other Phenolic Halogenated Pollutants in Human Blood Plasma. Arch. Environ. Contam. Toxicol. 2002, 42, 105-117.
43. Bowden, B. F.; Towerzey, L.; Junk, P. C. A New Brominated Diphenyl Ether from the Marine Sponge Dysidea herbacea. Aust. J. Chem. 2000, 53, 299-301.
44. Sharma, G. M.; Vig, B.; Burkholder, P. R. Antimicrobial Substances of Marine Sponges IV. Proc. Mar. Technol. Soc. 1969, 307.
45. Utkina, N. K.; Kazantseva, M. V.; Denisenko, V. A. Brominated Diphenyl Ethers from the Marine Sponge Dysidea fragilis. Chem. Nat. Compd. 1987, 1, 508-509.
46. Cameron, G. M.; Stapleton, B. L.; Simonsen, S. M.; Brecknell, D. J.; Garson, M. J. New Sesquiterpene and Brominated Metabolites from the Tropical Marine Sponge Dysidea Sp. Tetrahedron 2000, 56, 5247-5252.
47. Utkina, N. K.; Denisenko, V. A.; Virovaya, M. V.; Scholokova, O. V.; Prokofeva, N. G. Two New Minor Polybrominated Dibenzo-p-dioxins from the Marine Sponge Dysidea dendyi. J. Nat. Prod. 2002, 65, 1213-1215.
48. Vetter, W.; Stoll, E.; Garson, M. J.; Fahey, S. J.; Gaus, C.; Müller, J. F. Sponge Halogenated Natural Products Found at Parts-per-Million Levels in Marine Mammals. Environ. Toxicol. Chem. 2002, 21, 2014-2019.
49. Vetter, W. A GC/ECNI-MS Method for the Identification of Lipophilic Anthropogenic and Natural Brominated Compounds in Marine Samples. Anal. Chem. 2001, 73, 4951-4957.
50. Vetter, W.; Jun, W. Non-Polar Halogenated Natural Products Bioaccumulated in Marine Samples. II. Brominated and Mixed Halogenated Compounds,. Chemosphere 2003, 52, 423-431.
51. Kierkegaard, A.; Bignert, A.; Sellström, U.; Olsson, M.; Asplund, L.; Jansson, B.; de Wit, C. Polybrominated Diphenyl Ethers (PBDEs) and Their Methoxylated Derivatives in Pike from Swedish Waters with Emphasis on Temporal Trends, 1967-2000. Environ. Pollut. 2004, 130, 187-198.
52. Salva, J.; Faulkner, D. J. A New Brominated Diphenyl Ether from a Philippine Dysidea Species. J. Nat. Prod. 1990, 53, 757-760.
53. Reddy, C. M.; Xu, L.; Eglinton, T. I.; Boon, J. P.; Faulkner, D. J. Radiocarbon Content of Synthetic and Natural Semi-Volatile Halogenated Organic Compounds. Environ. Pollut. 2002, 120, 163-168.
54. Reddy, C. M.; Xu, L.; O'Neil, G. W.; Nelson, R. K.; Eglinton, T. I.; Faulkner, D. J.; Nordstrom, R.; Ross, P. S.; Tittlemier, S. A. Radiocarbon Evidence for a Naturally Produced, Bioaccumulating Halogenated Organic Compound. Environ. Sci. Technol. 2004, 38, 1992-1997.
55. Unson, M. D.; Holland, N. D.; Faulkner, D. J. A Brominated Secondary Metabolite Synthesized by the Cyanobacterial Symbiont of a Marine Sponge and Accumulation of the Crystalline Metabolite in the Sponge Tissue. Mar. Biol. 1994, 119, 1-11.