Enantioselective accumulation of chiral polychlorinated biphenyls in lotus plant (Nelumbonucifera spp.)

Dai, Shikun; Wong, Charles S.; Li, Yameng; Wang, Min; Chai, Tuanyao; Li, Fan; Yang, Shi‐Yao

doi:10.1016/j.jhazmat.2014.08.034

Cited by 22 publications

(17 citation statements)

References 32 publications

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“…To date, most PCB metabolism studies have focused on mammalian P450 enzymes; 18 , 20 − 23 , 48 however, there is growing evidence that P450 enzymes contribute to the biotransformation of PCBs in plants, 63 − 66 fish, 10 , 56 , 67 , 68 birds, 69 and marine mammals. 70 As suggested by our results, it is likely that hepatic and possibly extrahepatic metabolism by P450 enzymes plays a major role in the biotransformation of PCBs and structurally related compounds in wildlife, laboratory animals, and humans and contributes to the atropisomeric enrichment of PCBs observed in wildlife.…”

Section: Results and Discussionmentioning

confidence: 99%

Hepatic Metabolism Affects the Atropselective Disposition of 2,2′,3,3′,6,6′-Hexachlorobiphenyl (PCB 136) in Mice

Barnhart

Lein

et al. 2014

Environ. Sci. Technol.

107

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To understand the role of hepatic vs extrahepatic metabolism in the disposition of chiral PCBs, we studied the disposition of 2,2′,3,3′,6,6′-hexachlorobiphenyl (PCB 136) and its hydroxylated metabolites (HO-PCBs) in mice with defective hepatic metabolism due to the liver-specific deletion of cytochrome P450 oxidoreductase (KO mice). Female KO and congenic wild type (WT) mice were treated with racemic PCB 136, and levels and chiral signatures of PCB 136 and HO-PCBs were determined in tissues and excreta 3 days after PCB administration. PCB 136 tissue levels were higher in KO compared to WT mice. Feces was a major route of PCB metabolite excretion, with 2,2′,3,3′,6,6′-hexachlorobiphenyl-5-ol being the major metabolite recovered from feces. (+)-PCB 136, the second eluting PCB 136 atropisomers, was enriched in all tissues and excreta. The second eluting atropisomers of the HO-PCBs metabolites were enriched in blood and liver; 2,2′,3,3′,6,6′-hexachlorobiphenyl-5-ol in blood was an exception and displayed an enrichment of the first eluting atropisomers. Fecal HO-PCB levels and chiral signatures changed with time and differed between KO and WT mice, with larger HO-PCB enantiomeric fractions in WT compared to KO mice. Our results demonstrate that hepatic and, possibly, extrahepatic cytochrome P450 (P450) enzymes play a role in the disposition of PCBs.

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Section: Results and Discussionmentioning

confidence: 99%

Hepatic Metabolism Affects the Atropselective Disposition of 2,2′,3,3′,6,6′-Hexachlorobiphenyl (PCB 136) in Mice

Barnhart

Lein

et al. 2014

Environ. Sci. Technol.

107

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“…0.25 μm df) from Agilent was used for purity and concentration determinations, and the oven temperature was programmed as follows: 60 °C for 2 min, 60–150 °C at 10 °C·min −1 (held for 5 min), 150–180 °C at 1 °C·min −1 (held for 22 min). The SIM ions were m/z 360 (quantification ion), 362, and 358 7 . The purities of (−)-PCB149 and (+)-PCB149 were higher than >98.0%.…”

Section: Methodsmentioning

confidence: 99%

“…Adverse health effects such as neurological effects, in humans exposed to PCBs have been investigated in laboratory and epidemiological studies 6 . Nineteen PCBs congeners contain a chiral axis and exist as two stable isomers at ambient temperature 7 , and racemic PCBs produced via the PCB manufacturing process have been released into the environment 8 . Although enantioselective enrichments of chiral PCBs do not occur in abiotic processes, different biological and toxicological effects are observed when the individual enantiomers interact with chiral molecules such as enzymes and biological receptors 9 .…”

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confidence: 99%

Enantio-alteration of gene transcription associated with bioconcentration in adult zebrafish (Danio rerio) exposed to chiral PCB149

Chai

Cui

et al. 2016

Sci Rep

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Enantioselective enrichment of chiral PCB149 (2,2’,3,4’,5’,6-hexachlorobiphenyl) was analysed in adult zebrafish (Danio rerio) exposed to the racemate, (−)-PCB149, and (+)-PCB149. Greater enrichment of (−)-PCB149 compared to (+) PCB149 was observed following 0.5 ng/L exposure; however, as the exposure time and concentration increased, racemic enrichment was observed in adult fish exposed to the racemate. No biotransformation between the two isomers was observed in fish exposed to single enantiomers. When zebrafish were exposed to different forms of chiral PCB149, enantioselective expression of genes associated with polychlorinated biphenyls (PCBs) was observed in brain and liver tissues and enantioselective correlations between bioconcentration and target gene expression levels were observed in brain and liver tissues. The strong positive correlations between expression levels of target genes (alox5a and alox12) and PCB149 bioconcentration suggest that prolonged exposure to the racemate of chiral PCB149 may result in inflammation-associated diseases. Prolonged exposure to (−)-PCB149 may also affect metabolic pathways such as dehydrogenation and methylation in the brain tissues of adult zebrafish. Hepatic expression levels of genes related to the antioxidant system were significantly negatively correlated with bioconcentration following exposure to (+)-PCB149.

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“…The (À)-atropisomer elutes first for PCBs 95, 132, 136, and 149, and the (þ)-atropisomer elutes first for PCB 91 (Dai et al, 2014;Morrissey et al, 2007.). MeSO 2 -PCBs and OH-PCBs (OH-PCBs were derivatized to their methoxy analogues before instrumental analysis) were analyzed using an Agilent 6890 GC coupled with a 5975B mass selective detector in the electron capture negative ionization (ECNI) mode, and were separated with a DB-XLB (30 m Â 0.25 mm i.d.…”

Section: Instrumental Analysismentioning

confidence: 98%

Tracing the biotransformation of polychlorinated biphenyls (PCBs) in common carp (Cryprinus carpio): Enantiomeric fraction and compound-specific stable carbon isotope analyses

et al. 2016

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Enantioselective accumulation of chiral polychlorinated biphenyls in lotus plant (Nelumbonucifera spp.)

Cited by 22 publications

References 32 publications

Hepatic Metabolism Affects the Atropselective Disposition of 2,2′,3,3′,6,6′-Hexachlorobiphenyl (PCB 136) in Mice

Hepatic Metabolism Affects the Atropselective Disposition of 2,2′,3,3′,6,6′-Hexachlorobiphenyl (PCB 136) in Mice

Enantio-alteration of gene transcription associated with bioconcentration in adult zebrafish (Danio rerio) exposed to chiral PCB149

Tracing the biotransformation of polychlorinated biphenyls (PCBs) in common carp (Cryprinus carpio): Enantiomeric fraction and compound-specific stable carbon isotope analyses

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