Characterization of an abundant and novel methyl- and methoxy-substituted brominated diphenyl ether isolated from whale blubber

Chemosphere

Volumn 79, Issue 4, 2010, Pages 408-413

  Unger, Maria ^a   Asplund, Lillemor ^a   Marsh, Göran ^a   Gustafsson, Örjan ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

2 (2,4 dibromophenoxy) 6 methyl 3,4 dibromoanisole; 6 MeO 5 Me 2,2 ,3,4 tetrabromo diphenyl ether (6 MeO 5 Me BDE42); Natural brominated compounds; Nuclear magnetic resonance spectroscopy (NMR); Preparative capillary gas chromatography (PCGC)

Indexed keywords

ETHERS; HALOGEN COMPOUNDS; MAGNETIC RESONANCE SPECTROMETERS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC POLLUTANTS; ORGANIC POLYMERS;

2-(2,4-DIBROMOPHENOXY)-6-METHYL-3,4-DIBROMOANISOLE; BIOACCUMULATED COMPOUNDS; BROMINATED COMPOUNDS; BROMINATED DIPHENYL ETHERS; DIPHENYL ETHER; LOW RESOLUTION MASS SPECTROMETRIES; POLYBROMINATED DIPHENYL ETHERS; PREPARATIVE CAPILLARY GAS CHROMATOGRAPHY;

GAS CHROMATOGRAPHY;

ORGANOHALOGEN DERIVATIVE; POLYBROMINATED DIPHENYL ETHER;

BIOACCUMULATION; CONCENTRATION (COMPOSITION); ESTIMATION METHOD; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; ORGANOHALOGEN; PBDE; WHALE;

ANIMAL TISSUE; ARTICLE; BIOACCUMULATION; BOTTLENOSE WHALE; CAPILLARY GAS CHROMATOGRAPHY; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; HETERONUCLEAR SINGLE QUANTUM COHERENCE; MALE; MARINE ENVIRONMENT; NONHUMAN; PREPARATIVE CAPILLARY GAS CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; WHALE;

ATLANTIC OCEAN; NORTH SEA; SKAGERRAK;

CETACEA; HYPEROODON AMPULLATUS;

EID: 77949283257     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2010.01.067     Document Type: Article

References (39)

1. Athanasiadou M., Marsh G., Athanassiadis I., Asplund L., and Bergman A. Gas chromatography and mass spectrometry of methoxylated polybrominated diphenyl ethers (MeO-PBDEs). J. Mass Spectrom. 41 (2006) 790-801
2. Covaci A., Losada S., Roosens L., Vetter W., Santos F.J., Neels H., Storelli A., and Storelli M.M. Anthropogenic and naturally occurring organobrominated compounds in two deep-sea fish species from the Mediterranean Sea. Environ. Sci. Technol. 42 (2008) 8654-8660
3. Eglinton T.I., Aluwihare L.I., Bauer J.E., Druffel E.R.M., and McNichol A.P. Gas chromatographic isolation of individual compounds from complex matrices for radiocarbon dating. Anal. Chem. 68 (1996) 904-912
4. Eglinton T.I., BenitezNelson B.C., Pearson A., McNichol A.P., Bauer J.E., and Druffel E.R.M. Variability in radiocarbon ages of individual organic compounds from marine sediments. Science 277 (1997) 796-799
5. Faulkner D.J. Marine natural products. Nat. Prod. Rep. 17 (2000) 7-55
6. Faulkner D.J. Marine natural products. Nat. Prod. Rep. 18 (2001) 1-49
7. Flodin C., and Whitfield F.B. Brominated anisoles and cresols in the red alga Polysiphonia sphaerocarpa. Phytochemistry 53 (2000) 77-80
8. Gribble G.W. Naturally occurring organohalogen compounds. Acc. Chem. Res. 31 (1998) 141-152
9. Gribble G.W. The diversity of naturally occurring organobromine compounds. Chem. Soc. Rev. 28 (1999) 335-346
10. Haglund P.S., Zook D.R., Buser H.R., and Hu J.W. Identification and quantification of polybrominated diphenyl ethers and methoxy-polybrominated diphenyl ethers in Baltic biota. Environ. Sci. Technol. 31 (1997) 3281-3287
11. Hites R.A. Electron impact and electron capture negative ionization mass spectra of polybrominated diphenyl ethers and methoxylated polybrominated diphenyl ethers. Environ. Sci. Technol. 42 (2008) 2243-2252
12. Holmstrand H., Gadomski D., Mandalakis M., Tysklind M., Irvine R., Andersson P., and Gustafsson O. Origin of PCDDs in ball clay assessed with compound-specific chlorine isotope analysis and radiocarbon dating. Environ. Sci. Technol. 40 (2006) 3730-3735
13. Holmstrand H., Mandalakis M., Zencak Z., Gustafsson O., and Andersson P. Chlorine isotope fractionation of a semi-volatile organochlorine compound during preparative megabore-column capillary gas chromatography. J. Chromatogr. A 1103 (2006) 133-138
14. Holmstrand H., Mandalakis M., Zencak Z., Andersson P., and Gustafsson O. First compound-specific chlorine-isotope analysis of environmentally-bioaccumulated organochlorines indicates a degradation-relatable kinetic isotope effect for DDT. Chemosphere 69 (2007) 1533-1539
15. Hu J.W., Kolehmainen E., and Knuutinen J. H-1 and C-13 NMR spectroscopy of brominated diphenyl ethers. A multiple linear regression analysis. Magn. Reson. Chem. 38 (2000) 375-378
16. Jensen S., Athanasiadou M., and Bergman A. A technique for separation of xenobiotics from large amounts of lipids. Organohalogen Compd. 8 (1992) 79-80
17. Korytar P., Covaci A., de Boer J., Gelbin A., and Brinkman U.A.T. Retention-time database of 126 polybrominated diphenyl ether congeners and two Bromkal technical mixtures on seven capillary gas chromatographic columns. J. Chromatogr. A 1065 (2005) 239-249
18. Kumata H., Uchida M., Sakuma E., Uchida T., Fujiwara K., Tsuzuki M., Yoneda M., and Shibata Y. Compound class specific C-14 analysis of polycyclic aromatic hydrocarbons associated with PM10 and PM1.1 aerosols from residential areas of suburban Tokyo. Environ. Sci. Technol. 40 (2006) 3474-3480
19. Malmvärn A., Zebuhr Y., Kautsky L., Bergman A., and Asplund L. Hydroxylated and methoxylated polybrominated diphenyl ethers and polybrominated dibenzo-p-dioxins in red algae and cyanobacteria living in the Baltic Sea. Chemosphere 72 (2008) 910-916
20. Mandalakis M., and Gustafsson O. Optimization of a preparative capillary gas chromatography-mass spectrometry system for the isolation and harvesting of individual polycyclic aromatic hydrocarbons. J. Chromatogr. A 996 (2003) 163-172
21. Mandalakis M., Gustafsson O., Reddy C.M., and Li X. Radiocarbon apportionment of fossil versus biofuel combustion sources of polycyclic aromatic hydrocarbons in the Stockholm metropolitan area. Environ. Sci. Technol. 38 (2004) 5344-5349
22. Marsh G., Hu J.W., Jakobsson E., Rahm S., and Bergman A. Synthesis and characterization of 32 polybrominated diphenyl ethers. Environ. Sci. Technol. 33 (1999) 3033-3037
23. Marsh G., Stenutz R., and Bergman A. Synthesis of hydroxylated and methoxylated polybrominated diphenyl ethers - natural products and potential polybrominated diphenyl ether metabolites. Eur. J. Org. Chem. (2003) 2566-2576
24. Marsh G., Athanasiadou M., Bergman A., and Asplund L. Identification of hydroxylated and methoxylated polybrominated diphenyl ethers in Baltic Sea salmon (Salmo salar) blood. Environ. Sci. Technol. 38 (2004) 10-18
25. Marsh G., Athanasiadou M., Athanassiadis I., Bergman A., Endo T., and Haraguchi K. Identification, quantification and synthesis of a novel dimethoxylated polybrominated biphenyl in marine mammals caught off the coast of Japan. Environ. Sci. Technol. 39 (2005) 8684-8690
26. Melcher J., Olbrich D., Marsh G., Nikiforov V., Gaus C., Gaul S., and Vetter W. Tetra- and tribromopbenoxyanisoles in marine samples from Oceania. Environ. Sci. Technol. 39 (2005) 7784-7789
27. Pena-Abaurrea M., Weijs L., Ramos L., Borghesi N., Corsolini S., Neels H., Blust R., and Covaci A. Anthropogenic and naturally-produced organobrominated compounds in bluefin tuna from the Mediterranean Sea. Chemosphere 76 (2009) 1477-1482
28. Rayne S., Ikonomou M.G., Ross P.S., Ellis G.M., and Barrett-Lennard L.G. PBDEs, PBBs, and PCNs in three communities of free-ranging killer whales (Orcinus orca) from the northeastern Pacific Ocean. Environ. Sci. Technol. 38 (2004) 4293-4299
29. Sheesley R.J., Kruså M., Krecl P., Johansson C., and Gustafsson O. Source apportionment of elevated wintertime PAHs by compound-specific radiocarbon analysis. Atmos. Chem. Phys. 9 (2009) 3347-3356
30. Teuten E.L., Xu L., and Reddy C.M. Two abundant bioaccumulated halogenated compounds are natural products. Science 307 (2005) 917-920
31. Teuten E.L., Johnson C.G., Mandalakis M., Asplund L., Gustafsson O., Unger M., Marsh G., and Reddy C.M. Spectral characterization of two bioaccumulated methoxylated polybrominated diphenyl ethers. Chemosphere 62 (2006) 197-203
32. Teuten E.L., Pedler B.E., Hangsterfer A.N., and Reddy C.M. Identification of highly brominated analogues of Q1 in marine mammals. Environ. Pollut. 144 (2006) 336-344
33. 2 heterocyclic compound in seabird eggs. A bioaccumulating marine natural product?. Envinron. Sci. Technol. 33 (1999) 26-33
34. Unson M.D., Holland N.D., and 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. 119 (1994) 1-11
35. Utkina N.K., Denisenko V.A., Scholokova O.V., Virovaya M.V., Gerasimenko A.V., Popov D.Y., Krasokhin V.B., and Popov A.M. Spongiadioxins A and B, two new polybrominated dibenzo-p-dioxins from an Australian marine sponge Dysidea dendyi. J. Nat. Prod. 64 (2001) 151-153
36. Vetter W. A GC/ECNI-MS method for the identification of lipophilic anthropogenic and natural brominated compounds in marine samples. Anal. Chem. 73 (2001) 4951-4957
37. Vetter W., Turek C., Marsh G., and Gaus C. Identification and quantification of new polybrominated dimethoxybiphenyls (PBDMBs) in marine mammals from Australia. Chemosphere 73 (2008) 580-586
38. Zencak Z., Klanova J., Holoubek I., and Gustafsson O. Source apportionment of atmospheric PAHs in the western Balkans by natural abundance radiocarbon analysis. Environ. Sci. Technol. 41 (2007) 3850-3855
39. Zhu L.Y., and Hites R.A. Determination of polybrominated diphenyl ethers in environmental standard reference materials. Anal. Chem. 75 (2003) 6696-6700