Photolytic dehalogenation of the marine halogenated natural product Q1

The marine halogenated natural product 2,3,3',4,4',5,5'-heptachloro-1'-methyl-1,2'-bipyrrole (Q1) has been detected in high-trophic level biota throughout the world. In this study we UV-irradiated Q1 in order to produce hexahalogenated 1'-methylbipyrroles (Cl(6)-MBPs). Q1 was transformed with half-lives of <5 min. Already after 5 min, all of the five existing Cl(6)-MBPs (H1-H5) were detected in the irradiated sample. Only one Cl(6)-MBP (2,3,3',4',5,5'-hexachloro-1'-methyl-1,2'-bipyrrole (MBP-77, H2) has been previously described in the literature. H5 was identified as 2,3,3',4,4',5'-hexachloro-1'-methyl-1,2'-bipyrrole (MBP-75) by a specific fragment ion detected by GC/ECNI-MS. Fractionations of the irradiation mixture by reversed-phase HPLC followed by (1)H NMR analysis led to the structure of H4, i.e. 2,3,3',4,4',5-hexachloro-1'-methyl-1,2'-bipyrrole (MBP-74). H1 and H3 showed virtually identical (1)H NMR data. Therefore, it could not determined which of either isomers is 2,3,3',4,5,5'-hexachloro-1'-methyl-1,2'-bipyrrole (MBP-76) and which is 2,3,4,4',5,5'-hexachloro-1'-methyl-1,2'-bipyrrole (MBP-78). In addition, two pentachloro-MBPs (P1 and P3) could be traced back to MBP-62 and MBP-69. Cl(6)-MBPs were analyzed in whale blubber from Australia and skua adipose tissue from Antarctica. The marine mammals contained all Cl(6)-MBPs except for the most abundant in the irradiation experiment. The concentrations of the Cl(6)-MBPs amounted to 0.04-1.76% of the concentration of Q1. The highest concentrations of Cl(6)-MBP isomers in the biota samples were found for MBP-76, MBP-77, and MBP-78. These congeners appeared to be the most lipophilic ones owing to the highest retention time in RP-HPLC. Nevertheless, it remained unclear whether the Cl(6)-MBPs were actual halogenated natural products or environmental metabolites of Q1.     

Monobromo and higher brominated congeners of the marine halogenated natural product 2,3,3',4,4',5,5'-heptachloro-1'-methyl-1,2'-bipyrrole (Q1)

The marine halogenated natural product 2,3,3',4,4',5,5'-heptachloro-1'-methyl-1,2'-bipyrrole (Q1) is widely distributed in the environment. In this study, we screened samples which have previously been found to contain remarkably high residues of Q1 (blubber of marine mammals from Australia, samples from Antarctica, human milk from the Faroe Island) for the additional presence of mixed chlorinated and brominated congeners. Using GC/ECNI-MS, all samples tested were positive and many contained four out of five possible bromohexachloro congeners (BrCl6-MBPs), five out of 14 possible dibromopentachloro congeners (Br2Cl5-MBPs), five of 21 possible tribromotetrachloro-congeners (Br3Cl4-MBPs), as well as several higher brominated congeners. About 20 heptahalo congeners of Q1 are described for the first time in the scientific literature. Isomers eluted within about one minute, respectively. Hence it is possible, that the peak clusters identified may be composed of more, co-eluting congeners. Similarities in the GC/ECNI-MS mass spectra with polychlorinated biphenyls (PCBs) were addressed. We also suggest an acronym system similar to that in use for polychlorinated biphenyls that may simplify the use of this substance class in scientific papers. In the samples from Australia, BrCl6-MBPs and Br2Cl5-MBPs amounted for 7-27.5% and 0.4-4.2% of Q1, respectively whereas Br3Cl4-MBPs and higher brominated MBPs were found in the range of <1% of Q1 or less.     

Assessment of thyroid hormone activity of halogenated bisphenol A using a yeast two-hybrid assay

The thyroid hormone agonist/antagonist activities of halogenated derivatives of bisphenol A (BPA) were assessed using a yeast two-hybrid assay incorporating the human thyroid hormone α (TRα), both with and without possible metabolic activation by rat liver S9 preparation. In the absence of the rat liver S9 preparation, 3,3′,5,5′-tetrabromobisphenol A (TBBPA), 3,3′,5,5′-tetrachlorobisphenol A (TCBPA), and 3,3′,5-trichlorobisphenol A (3,3′,5-triClBPA) exhibited agonist activity, whereas 3-chlorobisphenol A (3-ClBPA), 3,5-dichlorobisphenol A (3,5-diClBPA), 3,3′-dichlorobisphenol A (3,3′-diClBPA), and BPA did not. The activities of TBBPA and TCBPA increased markedly (7.6-fold and 3.1-fold, respectively) after their metabolic activation with the rat liver S9 preparation. TBBPA, TCBPA, and 3,3′,5-triClBPA inhibited the binding of triiodothyronine (T3) to TRα at 2 × 10⁻⁵ M without rat liver S9 treatment and 4 × 10⁻⁶ M with rat liver S9 treatment, demonstrating their T3 antagonist activity. These results revealed that metabolic activation by rat liver S9 significantly increased the agonist/antagonist potential of some halogenated BPAs.     

Photoelectrocatalytic degradation of 4,4'-dibromobiphenyl in aqueous solution on TiO₂ and doped TiO₂ nanotube arrays

Polybrominated biphenyls have been widely used as flameretardants in textile and electronic industries, and additives in plastics. Over the past few decades, much attention has been given to polybrominated biphenyls in the environment and their effects on humans. In this paper, we studied on the degradation of 4,4′-dibromobiphenyl, a typical one of polybrominated biphenyls, through photoelectrocatalytic process with TiO₂, Zr/TiO₂ and Zr, N/TiO₂ nanotube arrays. The results showed that the photoelectrocatalytic process was more efficient than photocatalytic and electrolytic process alone. The results exhibited that the photoelectrocatalytic efficiency was significantly affected by the properties of the catalysts and bias potential, and the highest photoelectrocatalytic degradation rate was achieved with Zr, N/TiO₂ at 1 V and the order was Zr, N/TiO₂ > Zr/TiO₂ > TiO₂. The mechanism was also discussed by detecting the changes of pH value, bromine anion, total organic carbon and intermediates during the process.     

Levels of organochlorine pesticides and polychlorinated biphenyls in the critically endangered Iberian lynx and other sympatric carnivores in Spain

Accumulation of organochlorine compounds is well studied in aquatic food chains whereas little information is available from terrestrial food chains. This study presents data of organochlorine levels in tissue and plasma samples of 15 critically endangered Iberian lynx (Lynx pardinus) and other 55 wild carnivores belonging to five species from three natural areas of Spain (Doñana National Park, Sierra Morena and Lozoya River) and explores their relationship with species diet. The Iberian lynx, with a diet based on the consumption of rabbit, had lower PCB levels (geometric means, plasma: <0.01 ng mL⁻¹, liver: 0.4 ng g⁻¹ wet weight, fat: 87 ng g⁻¹ lipid weight) than other carnivores with more anthropic and opportunistic foraging behavior, such as the red fox (Vulpes vulpes; plasma: 1.11 ng mL⁻¹, liver: 459 ng g⁻¹, fat: 1984 ng g⁻¹), or with diets including reptiles at higher proportion, such as the Egyptian mongoose (Herpestes ichneumon; plasma: 7.15 ng mL⁻¹, liver: 216 ng g⁻¹, fat: 540 ng g⁻¹), or the common genet (Genetta genetta; liver: 466 ng g⁻¹, fat: 3854 ng g⁻¹). Chlorinated pesticides showed interspecific variations similar to PCBs. Organochlorine levels have declined since the 80s in carnivores from Doñana National Park, but PCB levels are still of concern in Eurasian otters (Lutra lutra; liver: 3873-5426 ng g⁻¹) from the industrialized region of Madrid.     

Aerobic degradation of tetrabromobisphenol-A by microbes in river sediment

This study investigated the aerobic degradation of tetrabromobisphenol-A (TBBPA) and changes in the microbial community in river sediment from southern Taiwan. Aerobic degradation rate constants (k₁) and half-lives (t_1/2) for TBBPA (50 μg g⁻¹) ranged from 0.053 to 0.077 d⁻¹ and 9.0 to 13.1 d, respectively. The degradation of TBBPA (50 μg g⁻¹) was enhanced by adding yeast extract (5 mg L⁻¹), sodium chloride (10 ppt), cellulose (0.96 mg L⁻¹), humic acid (0.5 g L⁻¹), brij 30 (55 μM), brij 35 (91 μM), rhamnolipid (130 mg L⁻¹), or surfactin (43 mg L⁻¹), with rhamnolipid yielding a higher TBBPA degradation than the other additives. For different toxic chemicals in the sediment, the results showed the high-to-low order of degradation rates were bisphenol-A (BPA) (50 μg g⁻¹) > nonylphenol (NP) (50 μg g⁻¹) > 4,4′-dibrominated diphenyl ether (BDE-15) (50 μg g⁻¹) > TBBPA (50 μg g⁻¹) > 2,2′,3,3′,4,4′,5,5′,6,6′-decabromodiphenyl ether (BDE-209) (50 μg g⁻¹). The addition of various treatments changed the microbial community in river sediments. The results also showed that Bacillus pumilus and Rhodococcus ruber were the dominant bacteria in the process of TBBPA degradation in the river sediments.     

Polarity effect of pulsed corona discharge for the oxidation of gaseous elemental mercury

The effect of polarity on the oxidation of Hg⁰ was examined in the presence of O₂ via a pulsed corona discharge (PCD). The experimental result showed no difference in the energy yield of Hg⁰ oxidation at both positive and negative PCDs (∼8 μg Hg W h⁻¹ at following conditions: total flow rate = 2 L min⁻¹ (Hg⁰ = 50 μg N m⁻³, O₂ = 10%, and N₂ balance), temperature = 150 °C, and specific energy density = 5-15 W h N m⁻³). This suggests that the positive PCD process used to control gaseous air pollutants may play an essential key role in Hg⁰ oxidation because it consumes enough energy (∼15 W h N m⁻³) but an electrical precipitator could not because it consumes less energy (∼0.3 W h N m⁻³) to oxidize Hg⁰.     

Immunotoxicity in ascidians: antifouling compounds alternative to organotins: III--the case of copper(I) and Irgarol 1051

After the widespread ban of TBT, due to its severe impact on coastal biocoenoses, mainly related to its immunosuppressive effects on both invertebrates and vertebrates, alternative biocides such as Cu(I) salts and the triazine Irgarol 1051, the latter previously used in agriculture as a herbicide, have been massively introduced in combined formulations for antifouling paints against a wide spectrum of fouling organisms. Using short-term (60 min) haemocyte cultures of the colonial ascidian Botryllus schlosseri exposed to various sublethal concentrations of copper(I) chloride (LC₅₀ = 281 μM, i.e., 17.8 mg Cu L⁻¹) and Irgarol 1051 (LC₅₀ > 500 μM, i.e., >127 mg L⁻¹), we evaluated their immunotoxic effects through a series of cytochemical assays previously used for organotin compounds. Both compounds can induce dose-dependent immunosuppression, acting on different cellular targets and altering many activities of immunocytes but, unlike TBT, did not have significant effects on cell morphology. Generally, Cu(I) appeared to be more toxic than Irgarol 1051: it significantly (p < 0.05) inhibited yeast phagocytosis at 0.1 μM (∼10 μg L⁻¹), and affected calcium homeostasis and mitochondrial cytochrome-c oxidase activity at 0.01 μM (∼1 μg L⁻¹). Both substances were able to change membrane permeability, induce apoptosis from concentrations of 0.1 μM (∼10 μg L⁻¹) and 200 μM (∼50 mg L⁻¹) for Cu(I) and Irgarol 1051, respectively, and alter the activity of hydrolases. Both Cu(I) and Irgarol 1051 inhibited the activity of phenoloxidase, but did not show any interactive effect when co-present in the exposure medium, suggesting different mechanisms of action.     

Quantitative assessment of the toxic effects of heavy metals on 1,2-dichloroethane biodegradation in co-contaminated soil under aerobic condition

1,2-Dichloroethane (1,2-DCA) is one of the most hazardous pollutant of soil and groundwater, and is produced in excess of 5.44 × 10⁹ kg annually. Owing to their toxicity, persistence and potential for bioaccumulation, there is a growing interest in technologies for their removal. Heavy metals are known to be toxic to soil microorganisms at high concentrations and can hinder the biodegradation of organic contaminants. In this study, the inhibitory effect of heavy metals, namely; arsenic, cadmium, mercury and lead, on the aerobic biodegradation of 1,2-DCA by autochthonous microorganisms was evaluated in soil microcosm setting. The presence of heavy metals was observed to have a negative impact on the biodegradation of 1,2-DCA in both soil samples tested, with the toxic effect being more pronounced in loam soil, than in clay soil. Generally, 75 ppm As³⁺, 840 ppm Hg²⁺, and 420 ppm Pb²⁺ resulted in 34.24%, 40.64%, and 45.94% increase in the half live (t_½) of 1,2-DCA, respectively, in loam soil, while concentrations above 127.5 ppm Cd²⁺, 840 ppm Hg²⁺ and 420 ppm of Pb²⁺ and less than 75 ppm As³⁺ was required to cause a >10% increase in the t_½ of 1,2-DCA in clay soil. A dose-dependent relationship between degradation rate constant (k₁) of 1,2-DCA and metal ion concentrations was observed for all the heavy metals tested, except for Hg²⁺. This study demonstrated that different heavy metals have different impacts on the degree of 1,2-DCA degradation. Results also suggest that the degree of inhibition is metal specific and is also dependent on several factors including; soil type, pH, moisture content and available nutrients.     

Effects of nano-TiO(2) in combination with ambient UV-irradiation on a leaf shredding amphipod

Production and use of engineered nanoparticles, such as titanium dioxide nanoparticles (nTiO₂), is increasing worldwide, enhancing their probability to enter aquatic environments. However, direct effects of nTiO₂ as well as ecotoxicological consequences due to the interactions of nTiO₂ with environmental factors like ultraviolet (UV) irradiation on representatives of detrital food webs have not been assessed so far. Hence, the present study displayed for the first time adverse sublethal effects of nTiO₂ at concentrations as low as 0.2 mg L⁻¹ on the leaf shredding amphipod Gammarus fossarum both in presence and absence of ambient UV-irradiation following a 7-d exposure. In absence of UV-irradiation, however, the effects seemed to be driven by accumulation of nTiO₂ at the bottom of the test vessels to which the gammarids were potentially exposed. The adverse sublethal and lethal effects on gammarids caused by the combined application of nTiO₂ and ambient UV-irradiation are suggested to be driven by the formation of reactive oxygen species. In conclusion, both the accumulation of nTiO₂ at the bottom of the test vessel and the UV induced formation of reactive oxygen species clearly affected its ecotoxicity, which is recommended for consideration in the environmental risk assessment of nanoparticles.     

Adsorption and breakdown of penicillin antibiotic in the presence of titanium oxide nanoparticles in water

The fate and transport of antibiotics in natural water systems is controlled in part by interactions with nanometer (10⁻⁹ m) metal oxide particles. Experiments were performed by mixing solutions of ampicillin (AMP), a common, penicillin-class human and veterinary antibiotic, with 25 nm-TiO₂ (anatase) nanoparticles at different pH conditions. Both sorption and degradation of AMP were observed in the AMP-nanoparticle solutions. For AMP concentrations from ∼3 μM to 2.9 mM the overall AMP removal from solution can be described by linear isotherms with removal coefficients (K_r) of 3028 (±267) L kg⁻¹ at pH 2, 11,533 (±823) L kg⁻¹ at pH 4, 12,712 (±672) L kg⁻¹ at pH 6, and 1941 (±342) L kg⁻¹ at pH 8. Mass spectral analysis of AMP solutions after removal of the solid nanoparticles yielded ions that indicate the presence of peniclloic acid, penilloic acid and related de-ammoniated by-products as possible compounds resulting from the degradation of AMP at the TiO₂ surface.     

Decomposition of 2,2',4,4',5,5'-hexachlorobiphenyl with iron supported on an activated carbon from an ion-exchange resin

An activated carbon (AC) containing a high concentration (374 mg g⁻¹) of Fe was prepared by carbonization of an ion-exchange resin. To examine its chemical reactivity as a catalyst to decompose 2,2′,4,4′,5,5′-hexachlorobiphenyl (PCB-153), the decomposition parameters of temperature and time were varied under air or N₂. Decomposition at 350 °C was achieved within 15 min under air and 30 min under N₂, and the efficiency of PCB-153 decomposition was 99.7% and 98.0%, respectively. An analysis of inorganic chloride ions revealed that PCB-153 was mineralized effectively during the decomposition. The Brunauer-Emmett-Teller (BET) surface area and pore volume of the AC were measured to assess the adsorption capacity before and after the decomposition. The differences between decomposition under air and N₂ reflected the differences in the BET surface and pore volume measurements. A decomposition pathway was postulated, and the reactive characteristics of chlorine atoms loaded on the benzene rings followed the order of para > meta > ortho, which agrees with the calculated results from a density functional theory study.     

The sea–air exchange of mercury (Hg) in the marine boundary layer of the Augusta basin (southern Italy): Concentrations and evasion flux

The first attempt to systematically investigate the atmospheric mercury (Hg) in the MBL of the Augusta basin (SE Sicily, Italy) has been undertaken. In the past the basin was the receptor for Hg from an intense industrial activity which contaminated the bottom sediments of the Bay, making this area a potential source of pollution for the surrounding Mediterranean. Three oceanographic cruises have been thus performed in the basin during the winter and summer 2011/2012, where we estimated averaged Hg_atm concentrations of about 1.5 ± 0.4 (range 0.9–3.1) and 2.1 ± 0.98 (range 1.1–3.1) ng m⁻³ for the two seasons, respectively. These data are somewhat higher than the background Hg_atm value measured over the land (range 1.1 ± 0.3 ng m⁻³) at downtown Augusta, while are similar to those detected in other polluted regions elsewhere. Hg evasion fluxes estimated at the sea/air interface over the Bay range from 3.6 ± 0.3 (unpolluted site) to 72 ± 0.1 (polluted site of the basin) ng m⁻² h⁻¹. By extending these measurements to the entire area of the Augusta basin (∼23.5 km²), we calculated a total sea–air Hg evasion flux of about 9.7 ± 0.1 g d⁻¹ (∼0.004 t yr⁻¹), accounting for ∼0.0002% of the global Hg oceanic evasion (2000 t yr⁻¹). The new proposed data set offers a unique and original study on the potential outflow of Hg from the sea–air interface at the basin, and it represents an important step for a better comprehension of the processes occurring in the marine biogeochemical cycle of this element.     

Partitioning behaviour of perfluorinated alkyl contaminants between water, sediment and fish in the Orge River (nearby Paris, France)

This paper reports on the partitioning behaviour of 15 perfluorinated compounds (PFCs), including C₄-C₁₀ sulfonates and C₅-C₁₄ carboxylic acids, between water, sediment and fish (European chub, Leuciscus cephalus) in the Orge River (nearby Paris). Total PFC levels were 73.0 ± 3.0 ng L⁻¹ in water and 8.4 ± 0.5 ng g⁻¹ in sediment. They were in the range 43.1-4997.2 ng g⁻¹ in fish, in which PFC tissue distribution followed the order plasma > liver > gills > gonads > muscle. Sediment-water distribution coefficients (log K_d) and bioaccumulation factors (log BAF) were in the range 0.8-4.3 and 0.9-6.7, respectively. Both distribution coefficients positively correlated with perfluoroalkyl chain length. Field-based biota-sediment accumulation factors (BSAFs) are also reported, for the first time for PFCs other than perfluorooctane sulfonate. log BSAF ranged between −1.3 and 1.5 and was negatively correlated with the perfluoroalkyl chain length in the case of carboxylic acids.     

Trichloroethylene decomposition and in-situ dry sorption of Cl-products by calcium oxides prepared from hydrated limes

A comparison of CaOs produced by calcining two types of hydrated lime and calcium carbonate was made for decomposition of trichloroethylene and in-situ dry sorption of the decomposed Cl-products using a lab-scale gas flow type tubular packed bed reactor. About 20 mg of CaO sample was mixed with about 2 g of Al₂O₃ particles and packed in the reactor and allowed to react with a flowing standard gas containing 500 ppm of C₂HCl₃ (N₂ balance) at 673 and 873 K, under the condition that the reaction of CaO with C₂HCl₃ might be completed within a few hours.It was found that no thermal decomposition of C₂HCl₃ at or below 673 K was observed in a reactor packed only with Al₂O₃ particles. However, a considerable amount of decomposition of C₂HCl₃ was obtained in a reactor packed with CaO and Al₂O₃, even at 673 K. For 1 mol of CaO prepared by calcining highly reactive Ca(OH)₂ at 673 K, decomposition of 0.42 mol of C₂HCl₃ and in-situ absorption product of 0.53 mol of CaCl₂ were obtained. At 873 K, about 46% of C₂HCl₃ was thermally decomposed. The total amount of C₂HCl₃ decomposed in CaO-Al₂O₃ particle bed at 873 K became nearly twice larger than that at 673 K. For 1 mol of CaO prepared by calcining highly reactive Ca(OH)₂ at 873 K, decomposition of 0.59 mol of C₂HCl₃ and in-situ absorption product of 0.67 mol of CaCl₂ were obtained. Small amounts of C₂Cl₂, C₂Cl₄, CCl₄, etc. were detected during decomposition of C₂HCl₃ at 673 and 873 K.It was recognized that the data on decomposition of C₂HCl₃ as well as in-situ dry sorption of Cl-products in CaO particle bed were correlated with specific surface area of the CaO employed.     

Impact of nano-CuO stress on rice (Oryza sativa L.) seedlings

Indiscriminate release of metal oxide nanoparticles (NPs) into the environment due to anthropogenic activities has become a serious threat to the ecological system including plants. The present study assesses the toxicity of nano-CuO on rice (Oryza sativa cv. Swarna) seedlings. Three different levels of stress (0.5 mM, 1.0 mM and 1.5 mM suspensions of copper II oxide, <50 nm particle size) were imposed and seedling growth performance was studied along control at 7 and 14 d of experiment. Modulation of ascorbate–glutathione cycle, membrane damage, in vivo ROS detection, foliar H₂O₂ and proline accumulation under nano-CuO stress were investigated in detail to get an overview of nano-stress response of rice. Seed germination percentage was significantly reduced under stress. Higher uptake of Evans blue by nano-CuO stressed roots over control indicates loss of root cells viability. Presence of dark blue and deep brown spots on leaves evident after histochemical staining with NBT and DAB respectively indicate severe oxidative burst under nano-copper stress. APX activity was found to be significantly increased in 1.0 and 1.5 mM CuO treatments. Nevertheless, elevated APX activity might be insufficient to scavenge all H₂O₂ produced in excess under nano-CuO stress. That may be the reason why stressed leaves accumulated significantly higher H₂O₂ instead of having enhanced APX activity. In addition, increased GR activity coupled with isolated increase in GSH/GSSG ratio does not seem to prevent cells from oxidative damages, as evident from higher MDA level in leaves of nano-CuO stressed seedlings over control. Enhanced proline accumulation also does not give much protection against nano-CuO stress. Decline in carotenoids level might be another determining factor of meager performance of rice seedlings in combating nano-CuO stress induced oxidative damages.     

Glucuronidation of hydroxylated polybrominated diphenyl ethers and their modulation of estrogen UDP-glucuronosyltransferases

Polybrominated diphenyl ethers (PBDEs) can be metabolically converted to their hydroxylated metabolites (OH-PBDEs). The estrogenic effects of PBDEs may be mediated by OH-PBDEs, but the mechanisms of which are still not understood. This study investigated the glucuronidation of 11 OH-PBDEs and their potential in modulating UDP-glucuronosyltransferases (UGTs) activity of 17β-estradiol (E2) in rat liver microsomes. The number of bromine atoms at phenolic ring was observed as the most influential factor of OH-PBDEs glucuronidation. 2′-OH-BDE-28 having one bromine atom at phenolic ring showed the fastest metabolic rates with t_1/2 value of 3.86 min, while 6-OH-BDE-137 having four bromine atoms at phenolic ring was the poorest substrate with t_1/2 value over 60 min. Regarding to the modulation of E2-UGTs activity, the phenolic hydroxyl group in OH-PBDEs played an essential role. Depending on the substitution patterns of bromine and hydroxyl group, OH-PBDEs inhibited or stimulated E2-UGTs activity. Ten of OH-PBDEs inhibited both 3-glucuronidation and 17-glucuronidation of E2 with IC₅₀ values varying from 3.80 to 129.38 μM, while 3′-OH-BDE-100 exhibited stimulating effects on 3-glucuronidation with EC₅₀ value of 35.95 μM. Kinetic analysis suggested noncompetitive inhibition mode of E2 glucuronidation by 3′-OH-BDE-7, 6-OH-BDE-47 and 2′-OH-BDE-68 with K_i values varying from 11.95 to 67.22 μM. This study demonstrated OH-PBDEs exhibited large interindividual differences in glucuronidation and modulation of E2-UGTs activity. By inhibiting the formation of E2 glucuronidation, OH-PBDEs may increase E2 bioavailability in target tissue, thereby exerting an indirect estrogenic effect.