Two Abundant Bioaccumulated Halogenated Compounds Are Natural Products

  title={Two Abundant Bioaccumulated Halogenated Compounds Are Natural Products},
  author={Emma L. Teuten and Li Xu and Christopher M. Reddy},
  pages={917 - 920}
Methoxylated polybrominated diphenyl ethers (MeO-PBDEs) have been found bioaccumulated in the tissues of a variety of aquatic animals and at concentrations comparable to those of anthropogenic halogenated organic compounds, including polychlorinated biphenyls (PCBs). The origin of the MeO-PBDEs has been uncertain; circumstantial evidence supports a natural and/or an industrial source. By analyzing the natural abundance radiocarbon content of two MeO-PBDEs isolated from a True's beaked whale… Expand
Biosynthesis of polybrominated aromatic organic compounds by marine bacteria
Polybrominated diphenyl ethers (PBDEs) and polybrominated bipyrroles are natural products that bioaccumulate in the marine food chain. PBDEs have attracted widespread attention due to theirExpand
Marine halogenated natural products of environmental relevance.
  • W. Vetter
  • Environmental Science, Medicine
  • Reviews of environmental contamination and toxicology
  • 2006
A wide range and steadily increasing number of halogenated natural products (HNPs) is detected in marine organisms that are not the natural source of these compounds but which have accumulated theseExpand
Natural Production of Organohalide Compounds in the Environment
More than 5000 natural organohalogen compounds have been identified. In terrestrial environments, the bulk of the organochlorine is locked up in humic polymers, collectively accounting for a globalExpand
Enzymatic Synthesis of Polybrominated Dioxins from the Marine Environment
It is reported that the bmp gene locus in marine bacteria, a recently characterized source of polybrominated diphenyl ethers, can also synthesize dibenzo-p-dioxins by employing different phenolic initiator molecules. Expand
Contemporary 14C radiocarbon levels of oxygenated polybrominated diphenyl ethers (O-PBDEs) isolated in sponge-cyanobacteria associations.
The modern radiocarbon content of diphenyl ethers, C(12)H(22)O) indicates that they are naturally produced, adding to a growing baseline on, at least, the sources of these unusual compounds. Expand
Complexity of naturally produced polybrominated diphenyl ethers revealed via mass spectrometry.
Using mass spectrometry and NMR spectroscopy, the existence of new structural classes of PBDEs in marine sponges is established and this work expands the chemical space explored by naturally producedPBDEs, which may inform future environmental toxicology studies. Expand
Biomagnification of anthropogenic and naturally-produced organobrominated compounds in a marine food web from Sydney Harbour, Australia.
The higher levels of MeO-PBDEs and PBHDs in the samples from the harbour confirmed the marine (natural) origin of these compounds, and suggests that biomagnification occurs in the studied aquatic food chain for anthropogenic brominated compounds, but also for the naturally-produced organobromines. Expand
Food web bioaccumulation of organohalogenated compounds in high mountain lakes
Persistent organic pollutants (POPs) are toxic substances that are usually produced for use in agricultural, industrial, and domestic applications. Because of their long-range atmospheric transportExpand
Concentrations of halogenated natural products versus PCB 153 in bivalves from the North and Baltic Seas.
The concentrations of HNPs varied by two orders of magnitude, compared to a factor of 10 for PCB 153, suggesting that HnPs are more spatially (and perhaps temporally) variant than POPs. Expand
Halogenated organic compounds in archived whale oil: a pre-industrial record.
An archived whale oil sample collected in 1921 from the last voyage of the whaling ship Charles W. Morgan is analyzed and indicates, at least in part, a natural source of halogenated methyl bipyrroles and dimethoxylated polybrominated biphenyl. Expand


Radiocarbon content of synthetic and natural semi-volatile halogenated organic compounds.
The results suggest that measuring the 14C content of halogenated organic compounds may be quite useful in establishing whether organic compounds encountered in the environment have natural or synthetic origins (or both) provided that any synthetic counterparts derive from petrochemical feedstock. Expand
Radiocarbon evidence for a naturally produced, bioaccumulating halogenated organic compound.
The presence of detectable 14C in the DBP-Br4Cl2 strongly points to at least a natural or biogenic source, however, these delta14C values for DBPs are more depleted than expected for a recently synthesized natural product. Expand
Sponge halogenated natural products found at parts-per-million levels in marine mammals.
The quantitative determination ofBC-2 in blubber of marine mammals from Africa and the Antarctic suggests that BC-2 is widespread, and is direct proof that marine biota can produce persistent organic chemicals that accumulate to substantial concentrations in higher trophic organisms. Expand
Two new minor polybrominated dibenzo-p-dioxins from the marine sponge Dysidea dendyi.
Two new minor tribromodibenzo-p-dioxins, spongiadioxin C and its methyl ether, were isolated from an Australian marine sponge Dysidea dendyi and inhibited the cell division of fertilized sea urchin eggs. Expand
Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia.
The marine sponge Dysidea herbacea collected from Indonesia yielded four new polybrominated diphenyl ether congeners 2-5 and the known derivatives 1, 6, and 7, which were active against the Gram-positive bacteria Bacillus subtilis and the phytopathogenic fungus Cladosporium cucumerinum. Expand
Photochemical decomposition of 15 polybrominated diphenyl ether congeners in methanol/water.
The photochemical reaction rate decreased with decreasing number of bromine substituents in the molecule but also in some cases influenced by the PBDE substitution pattern, and the reaction rate was dependent on the solvent in such a way that the Reaction rate in a methanol/water solution was consistently around 1.7 times lower than in pure methanolate and 2-3 times lower in THF. Expand
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Biodegradation of diphenyl ether and its monohalogenated derivatives by Sphingomonas sp. strain SS3
Formation of phenol, catechol, halophenol, and halocatechol from the conversion of monohalogenated diphenyl ethers gives evidence for a nonspecific attack of the dioxygenating enzyme system. Expand
Enzyme inhibitors: new and known polybrominated phenols and diphenyl ethers from four Indo-Pacific Dysidea sponges.
Extracts and pure compounds isolated from four samples of Dysidea sp. sponges collected from two geographically distinct regions of the Indo-Pacific (Chuuk Atoll and Fiji) were assayed against fiveExpand
Metabolism in the toxicokinetics and fate of brominated flame retardants--a review.
Substantially more research is necessary to fully assess BFR fate, uptake and elimination kinetics, metabolic pathways, inter-species differences, the influence of congener structure, and the potential health risks to exposed organisms. Expand