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Photochemical formation of polybrominated dibenzo-p-dioxins from environmentally abundant hydroxylated polybrominated diphenyl ethers
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2012 (English)In: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 46, no 14, 7567-7574 p.Article in journal (Refereed) Published
Abstract [en]

High levels of polybrominated dibenzo-p-dioxins (PBDDs) have been found in Baltic Sea biota, where the toxic load owing to, for example, polychlorinated dibenzo-p-dioxins and other organic pollutants is already high. The levels and geographic pattern of PBDDs suggest biogenic rather than anthropogenic origin, and both biotic and abiotic formation pathways have been proposed. Photochemical formation from hydroxylated polybrominated diphenyl ethers (OH-PBDE) is a proposed pathway. for PBDDs in marine environments. Ultraviolet radiation-initiated transformations of OH-BDEs 47, 68, 85, 90, 99, and 123, which all are abundant in the environment, were investigated. It was shown that the most abundant PBDDs in the environment (1,3,7-triBDD and 1,3,8-triBDD) can be formed from the most abundant OH-BDEs (OH-BDE 47 and OH-BDE 68) at high rates and with percentage yields. In fact, most of the PBDDs that have been identified in the Baltic Sea environment were formed with high yield from the six studied OH-PBDE, through initial cyclization and subsequent debromination reactions. The high formation yields point to this route as an important source of PBDDs in biota. However, congeners showing relatively high retention in fish, specifically 1,3,6,8- and 1,3,7,9-tetraBDD, were not formed. These are likely formed by enzymatic coupling of brominated phenols.

Place, publisher, year, edition, pages
2012. Vol. 46, no 14, 7567-7574 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-59535DOI: 10.1021/es301256xISI: 000306441000019OAI: oai:DiVA.org:umu-59535DiVA: diva2:552892
Available from: 2012-09-17 Created: 2012-09-17 Last updated: 2017-12-07Bibliographically approved
In thesis
1. Polybrominated dibenzo-p-dioxins: Natural formation mechanisms and biota retention, maternal transfer, and effects
Open this publication in new window or tab >>Polybrominated dibenzo-p-dioxins: Natural formation mechanisms and biota retention, maternal transfer, and effects
2012 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Polybrominated dibenzo-p-dioxins (PBDD) and dibenzofurans (PBDF) are a group of compounds of emerging interest as potential environmental stressors. Their structures as well as toxic responses are similar to the highly characterized toxicants polychlorinated dibenzo-p-dioxins. High levels of PBDDs have been found in algae, shellfish, and fish, also from remote areas in theBaltic Sea. This thesis presents studies on PBDD behavior in fish and offspring, and natural formation of PBDDs from naturally abundant phenolic precursors.

The uptake, elimination, and maternal transfer of mono- to tetraBDD/Fs were investigated in an exposure study reported in Paper I. The effects of PBDDs in fish were examined in a dose-response study (Paper II). It was shown that fish can assimilate PBDD/Fs from their feed, although non-laterally substituted congeners were rapidly eliminated. Laterally substituted congeners were retained as was congeners without vicinal hydrogens to some extent. PBDD/Fs were transferred to eggs, and congeners that were rapidly eliminated in fish showed a higher transfer ratio to eggs. Exposure to the laterally substituted 2,3,7,8-TeBDD had significant effects on the health, gene expression and several reproduction end-points of zebrafish, even at the lowest dose applied.

The geographical and temporal variations of PBDD in biota samples from the Baltic Seasuggest biogenic rather than anthropogenic origin. In Paper III, bromoperoxidase-mediated coupling of 2,4,6-tribromophenol yielded several PBDD congeners, some formed after rearrangement. The overall yield was low, but significantly higher at low temperature, and the product profile obtained was similar to congener profiles found in biota from the Swedish West Coast. In Paper IV, photo­chemi­cally induced cyclization of hydroxylated polybrominated diphenyl ethers under natural conditions produced PBDDs at percentage yield. Rearranged products were not detected, and some abundant congeners do not seem to be formed this way. However, the product profile obtained was similar to congener profiles found in biota from the Baltic Proper.

Since the PBDD congeners found in biota have a high turn-over in fish, the exposure must be high and continuous to yield the PBDD levels measured in wild fish. Thus, PBDDs must presumably be formed by common precursors in general processes, such as via enzymatic oxidations, UV-initiated reactions or a combination of both. The presented pathways for formation of PBDDs are both likely sensitive to changes in climatic conditions.

Place, publisher, year, edition, pages
Umeå: Umeå Universitet, 2012. 65 p.
Keyword
polybrominated dibenzo-p-dioxins, PBDDs, Baltic Sea, uptake, retention, maternal transfer, metabolism, bioavailability, natural formation, precursor, bromoperoxidase, bromophenol, photochemical transformation, oxidative coupling, hydroxylated polybrominated diphenyl ethers
National Category
Chemical Sciences
Research subject
Analytical Chemistry
Identifiers
urn:nbn:se:umu:diva-50887 (URN)
Public defence
2012-02-03, KBC-huset, Hörsal KB3B1, Umeå universitet, Umeå, 10:00 (English)
Opponent
Supervisors
Available from: 2012-01-13 Created: 2011-12-29 Last updated: 2017-09-01Bibliographically approved

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Arnoldsson, KristinaAndersson, Patrik LHaglund, Peter

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