Can Physicochemical and Microbial Soil Properties Explain Enantiomeric Shifts of Chiral Organochlorines?

Kobližková, Martina; Dušek, Ladislav; Jarkovský, Jiří; Hofman, Jakub; Bucheli, Thomas D.; Klánová, Jana

doi:10.1021/es800625d

Cited by 36 publications

(36 citation statements)

References 32 publications

(58 reference statements)

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“…This finding is consistent with previous observation that nonracemic EFs appeared to be increasingly probable in soil with relatively low PCB concentrations. 40 Nevertheless, a more likely explanation is that the EFs in the literature were mostly from developed countries where previously used PCBs have stayed in the soil for decades, while a significant proportion of the PCBs in the soils in the present study was newly released. The concentration alone may have a small influence on the degree of enantioselective degradation of PCBs in soil.…”

Section: ■ Results and Discussionmentioning

confidence: 78%

“…Field blanks [PUF plugs and glass fiber filters (GFFs)] were prepared, and procedural blanks were run with each bath of the field samples to assess blank levels. Several PCBs (PCB 11,26,33,37,40,71,76,103,111,128,170,175,190, and 209) were found in the procedural and field blanks; however, their quantities were less than 5% of those in the field sample extracts, in most cases. The concentrations in the samples were blank-corrected.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Elevated Levels of Polychlorinated Biphenyls in Plants, Air, and Soils at an E-Waste Site in Southern China and Enantioselective Biotransformation of Chiral PCBs in Plants

Chen

Tian

Zheng

et al. 2014

Environ. Sci. Technol.

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E-waste that contains polychlorinated biphenyls (PCBs) is moved across national boundaries, often from industrialized countries in the northern hemisphere, where the items were formerly used, to subtropical and tropical regions in southeastern Asia and Africa. As a result, there is a high likelihood that PCBs will be released into the environment from a primary source due to the elevated temperatures encountered in these lowlatitude regions. In the present study, PCBs and enantiomer fractions (EFs) of chiral PCBs (PCB 84, 95, 132, 136, 149, and 183) were analyzed in air, eucalyptus leaves, pine needles, and soil at an ewaste site and a rural site in southern China. The concentrations of PCBs at the e-waste site ranged from 7825 to 76330 pg/m 3 , 27.5 to 1993 ng/g, and 24.2 to 12045 ng/g in the air (gas plus particle), plant leaves, and soils, respectively. The atmospheric PCB composition profiles in the present study indicated relatively high abundances of penta-and hexa-PCBs, which were different from those previously observed in the air across China. The Clausius−Clapeyron regression analysis indicated that evaporation from local contaminated surfaces constitutes a primary emission source of PCBs in the air at the e-waste site. The chiral signatures of PCBs in the air at the e-waste site were essentially racemic (mean EFs = (0.484 ± 0.022)−(0.499 ± 0.004) in the gaseous phase) except for PCB 84 (0.420 ± 0.050), indicating that racemic sources dominate the PCB emission in the air. PCB chiral signatures in the soils ((0.422 ± 0.038)−(0.515 ± 0.016)) were similar to those in the air except for PCB 95. However, the chiral PCBs in the plants (especially the eucalyptus leaves) had significantly nonracemic residues ((0.368 ± 0.075)−(0.561 ± 0.045)) compared to those in the air and soil. This finding suggests that enantioselective biotransformation of these atropisomeric PCBs was very likely to occur in the plant leaves, possibly due to metabolism by cytochrome P-450 enzymes in leaves. To our knowledge, this is the first report on the enantioselective metabolism of chiral PCBs in plants under field conditions.

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Section: ■ Results and Discussionmentioning

confidence: 78%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Elevated Levels of Polychlorinated Biphenyls in Plants, Air, and Soils at an E-Waste Site in Southern China and Enantioselective Biotransformation of Chiral PCBs in Plants

Chen

Tian

Zheng

et al. 2014

Environ. Sci. Technol.

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“…To overcome the problem of coelution, chiral analysis of POPs is generally performed by heart-cut multidimensional gas chromatography (MDGC) [7,11,[15][16][17][19][20][21][22] and comprehensive two-dimensional gas chromatography (GC x GC) [11,15,17,19]. An excellent review of multidimensional chromatography in pesticides analysis can be found in Tuzimski [23].…”

Section: Introductionmentioning

confidence: 99%

“…Organochlorine pesticides are typically solvent extracted from soil by Soxhlet extraction [9,18,20,21,24,25] and by sonication [7]. Microlitre amounts are injected for analysis.…”

Section: Introductionmentioning

confidence: 99%

Two multidimensional chromatographic methods for enantiomeric analysis of o,p′-DDT and o,p′-DDD in contaminated soil and air in a malaria area of South Africa

Naude

Rohwer

2012

Analytica Chimica Acta

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In rural parts of South Africa the organochlorine insecticide DDT (1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane) is still used for malaria vector control where traditional dwellings are sprayed on the inside with small quantities of technical DDT. Since o,p'-DDT may show enantioselective oestrogenicity and biodegradability, it is important to analyse enantiomers of o,p'-DDT and its chiral degradation product, o,p'-DDD, for both health and environmentalforensic considerations. Generally, chiral analysis is performed using heartcut multidimensional gas chromatography (MDGC) and, more recently, comprehensive two-dimensional gas chromatography (GC x GC). We developed an off-line gas chromatographic fraction collection (heart-cut) procedure for the selective capturing of the appropriate isomers from a first

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“…24,26) Monitored ions are given in these references. Analytical methods for PCB atropisomers by other research groups [27][28][29][30][31][32] involve chromatography on chiral-phase columns with detection by electron impact MS. The most popular column is ChirasilDex (10% permethylated 2,3,6-tri-O-methyl β-cyclodextrin as chiral selector in polysiloxane, 25 or 30 m×0.25 mm i.d., 0.25 µm film, Chrompack or Varian), and in one case 29) Cyclosil-B (30% heptakis (2,3-di-O-methyl-6-Otert-butyldimethylsilyl)-β-cyclodextrin in 14% cyanopropylphenyl/86% methylpolysiloxane, 30 m×0.25 mm i.d., 0.5 µm film, Agilent, U.S.A.) was also used.…”

Section: Methodsmentioning

confidence: 99%

Chiral Chemicals as Tracers of Atmospheric Sources and Fate Processes in a World of Changing Climate

et al. 2013

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Elimination of persistent organic pollutants (POPs) under national and international regulations reduces "primary" emissions, but "secondary" emissions continue from residues deposited in soil, water, ice and vegetation during former years of usage. In a future, secondary source controlled world, POPs will follow the carbon cycle and biogeochemical processes will determine their transport, accumulation and fate. Climate change is likely to affect mobilisation of POPs through e.g., increased temperature, altered precipitation and wind patterns, flooding, loss of ice cover in polar regions, melting glaciers, and changes in soil and water microbiology which affect degradation and transformation. Chiral compounds offer advantages for following transport and fate pathways because of their ability to distinguish racemic (newly released or protected from microbial attack) and nonracemic (microbially degraded) sources. This paper discusses the rationale for this approach and suggests applications where chiral POPs could aid investigation of climate-mediated exchange and degradation processes. Multiyear measurements of two chiral POPs, trans-chlordane and α-HCH, at a Canadian Arctic air monitoring station show enantiomer compositions which cycle seasonally, suggesting varying source contributions which may be under climatic control. Largescale shifts in the enantioselective metabolism of chiral POPs in soil and water might influence the enantiomer composition of atmospheric residues, and it would be advantageous to include enantiospecific analysis in POPs monitoring programs.

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Can Physicochemical and Microbial Soil Properties Explain Enantiomeric Shifts of Chiral Organochlorines?

Cited by 36 publications

References 32 publications

Elevated Levels of Polychlorinated Biphenyls in Plants, Air, and Soils at an E-Waste Site in Southern China and Enantioselective Biotransformation of Chiral PCBs in Plants

Elevated Levels of Polychlorinated Biphenyls in Plants, Air, and Soils at an E-Waste Site in Southern China and Enantioselective Biotransformation of Chiral PCBs in Plants

Two multidimensional chromatographic methods for enantiomeric analysis of o,p′-DDT and o,p′-DDD in contaminated soil and air in a malaria area of South Africa

Chiral Chemicals as Tracers of Atmospheric Sources and Fate Processes in a World of Changing Climate

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