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Enantiomeric Excess of POPs in the Environment

Enantiomeric Excess of POPs in the Environment. Hiramoto S 1 , Tsurukawa M 2 , Matsumura C 2 , Nakano T 2 , Kunugi M 3 1 Hyogo Environmental Advancement Association 2 Hyogo Prefectural Institute of Public Health Association 3 National Institute for Environmental Studies. Introduction.

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Enantiomeric Excess of POPs in the Environment

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  1. Enantiomeric Excess of POPs in the Environment Hiramoto S1, Tsurukawa M2, Matsumura C2, Nakano T2, Kunugi M3 1Hyogo Environmental Advancement Association 2Hyogo Prefectural Institute of Public Health Association 3National Institute for Environmental Studies

  2. Introduction

  3. Purpose • To identify the behavior of POPs • Enantiomeric compositions of chiral POPs in seawater and air were investigated. • The results of chiral analysis were shown using Enantiomeric Excess (EE). * In this study, (+) or (-) enantiomer does not identified.

  4. Metabolites showed enantioselective degradation of (+) or (-) enantiomer. Enantiomeric Excess(EE) Changes in physicochemical status, the EE value doesnot change. Changes in metabolic status, the EE valuechanges. It is possible to distinguish between newly caused pollution and preserved by monitoring EE

  5. Materials and Methods

  6. S-1 S-2 S-3 S-4 S-9 S-5 S-8 S-6 S-10 S-7 S-11 May～June 2006 Sampling Sites (Seawater)～South China Sea～

  7. P-7 P-5 P-6 P-4 P-3 P-2 P-1 Sampling Sites (Seawater)～Pacific Ocean (West)～ August～September 2005

  8. P-8 P-9 P-10 P-11 August～September 2005 Sampling Sites (Seawater)～Pacific Ocean (East)～ UNITED STATES San Francisco

  9. N-2 N-3 N-4 N-1 May～June 2005 Sampling Sites (Air)～North Atlantic Ocean～

  10. Extraction Column Filter unit Marine pollution observation system Marine pollution observation system Solid Phase Extraction unit Control Unit

  11. Air 400m3 Seawater 100L Sample（PUF＋ACF） Soxhlet Extraction 3hr with acetone 24hr for dichloromethane Polyurethane foam （PUF） Concentration Exchange to hexane Concentration , Dehydration Glass holder Clean up with silica gel Active carbon fiber filter （ACF） Concentration HRGC/HRMS Sample Preparation for Analysis Spiked with 13C-labeld POPs

  12. o,p’ - DDT trans - Chlordane cis - Chlordane Heptachlor α - HCH o,p’ - DDD Oxychlordane Heptachlor epoxide o,p’ - DDE Target Analytes Technical compounds Metabolites

  13. HRGC/HRMS ＊BGB-172（20% tert-butyldimethylsilyl-β-cyclodextrin dissolved in 15% diphenyl-polysiloxane and 85% dimethylpolysiloxane）

  14. HP-5 α γ β δ BGB-172 δ γ β α

  15. Enantiomeric Excess (EE) EE(%) = *100 EL : amount of larger enantiomer ES : amount of smaller enantiomer EL-ES EL+ES (-) (+) (-) (-) (+) (+) (+) (-) (+) (-) Enantiomeric Excess EE= 0 %

  16. Results

  17. beta- delta- HCH alpha- standard EE = 1% gamma- Seawater ( South China Sea) EE = 6% RACEMIC Seawater ( Pacific Ocean) EE = 10% Air (North Atlantic Ocean) EE = 3%

  18. EE = 1% EE = 1% trans- Chlordane standard cis- Seawater ( South China Sea) trans-EE = 4% cis-EE = 5% RACEMIC Seawater ( Pacific Ocean) trans-EE = 4% cis-EE = 1% Air (North Atlantic Ocean) trans-EE = 4% cis-EE = 7%

  19. EE = 39% EE = 28% EE = 44% exo- Heptachlor epoxide EE = 1% standard endo- EE = 1% Seawater ( South China Sea) NON RACEMIC Seawater ( Pacific Ocean) Air (North Atlantic Ocean)

  20. EE = 51% EE = 58% DDD p,p’- o,p’- standard EE= 1 % Seawater ( South China Sea) NON RACEMIC Seawater ( Pacific Ocean) Air (North Atlantic Ocean)

  21. Oxychlordane EE=1% standard Seawater ( South China Sea) Seawater ( Pacific Ocean) RACEMIC EE=1% Air (North Atlantic Ocean)

  22. Metabolite Technical compound

  23. Metabolite Technical compound

  24. Metabolite Technical compound

  25. Conclusion(1) • EE of chiral POPs in seawater and air samples have been investigated. • Enatiomeric composition of alpha-HCH, trans-,cis-chlordane were near racemic. • The metabolites; heptachlor exo-epoxide and o,p’-DDD exist non racemic. • However, oxychlordane is the metabolite, it exists as racemic.

  26. Conclusion(2) • By monitoring enantiomeric composition, better understanding for the mechanism of environmental pollution will be provided. • Further studies about global scale observations of chiral signatures are necessary.

  27. EE values (South China Sea)

  28. S-1 S-2 S-3 S-4 S-9 S-5 S-8 S-6 S-10 S-7 S-11 EE values (South China Sea)

  29. EE values (Pacific Ocean)

  30. P-7 P-5 P-8 P-10 P-6 P-9 P-4 P-11 P-3 P-2 P-1 EE values (Pacific Ocean)

  31. EE values (North Atlantic Ocean)

  32. N-2 N-3 N-4 N-1 EE values (North Atlantic Ocean)

  33. Persistent Organic Pollutants (POPs) ① Toxic ② Persistent in the environment ③ Bioaccumulative through the food web ④ Long-range transportable Stockholm Convention (May 2001) Take measures to eliminate Reduce the release into the environment

  34. Results • EEs of alpha-HCH, trans-,cis-chlordane in air samples and seawater samples range from 0.1 to 15.9% and 0.5 to 38.4%, respectively. • EEs of metabolites heptachlor exo-epoxide in air samples and seawater samples range from 7.6 to 43.8% and 6.5 to 38.8%, respectively. • The range of EEs of metabolites o,p’-DDD in seawater samples were from 20.7 to 64.4%.

  35. trans- cis- MC5 EE= 7 % EE= 5 % EE= 5 %

  36. S-1 S-2 S-3 S-4 S-9 S-5 S-8 S-6 S-10 S-7 S-11 EE values (South China Sea)

  37. P-7 P-5 P-8 P-10 P-6 P-9 P-4 P-11 P-3 P-2 P-1 EE values (Pacific Ocean)

  38. N-2 N-3 N-4 N-1 EE values (North Atlantic Ocean)

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