Enantioselectivity tuning of chiral herbicide dichlorprop by copper: Roles of reactive oxygen species

Environmental Science and Technology

Volumn 45, Issue 11, 2011, Pages 4778-4784

  Wen, Yuezhong ^a   Chen, Hui ^a   Shen, Chensi ^a   Zhao, Meirong ^b   Liu, Weiping ^c  

^a Institute of Environmental Sciences   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT DEFENSE; ANTIOXIDANT RESPONSE; CELL TOXICITY; CHEMICAL CONTAMINANTS; ECOTOXICITY; ENANTIOSELECTIVE; GROWTH INHIBITION; PHYSIOLOGICAL FUNCTIONS; REACTIVE OXYGEN SPECIES; SCENEDESMUS; SUBCELLULAR STRUCTURE;

ALGAE; CHIRALITY; ECOLOGY; ENANTIOMERS; ENANTIOSELECTIVITY; GROWTH KINETICS; HEAVY METALS; HERBICIDES; IMPURITIES; OXYGEN; PESTICIDE EFFECTS; PHYSIOLOGICAL MODELS; RISK ASSESSMENT; WEED CONTROL;

TOXICITY;

CHLOROPHYLL A; CHLOROPHYLL B; COPPER; DICHLORPROP; REACTIVE OXYGEN METABOLITE;

ANTIOXIDANT; CHEMICAL POLLUTANT; COPPER; ECOTOXICOLOGY; GREEN ALGA; GROWTH RESPONSE; HERBICIDE; INHIBITION; OXYGEN; PHYSIOLOGICAL RESPONSE; RISK ASSESSMENT; TOXICITY TEST;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL FUNCTION; CELL MEMBRANE PERMEABILITY; CELL STRUCTURE; CHEMICAL INTERACTION; CHIRALITY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ECOTOXICITY; ENANTIOSELECTIVITY; GROWTH INHIBITION; NONHUMAN; SCENEDESMUS;

2,4-DICHLOROPHENOXYACETIC ACID; ANTIOXIDANTS; CELL MEMBRANE PERMEABILITY; CHLOROPHYLL; COPPER; HERBICIDES; MALONDIALDEHYDE; OXIDATIVE STRESS; PESTICIDE SYNERGISTS; REACTIVE OXYGEN SPECIES; SCENEDESMUS; STEREOISOMERISM;

ALGAE; SCENEDESMUS OBLIQUUS;

EID: 79957819736     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es2003793     Document Type: Article

References (28)

1. Turgut, C. The contamination with organochlorine pesticides and heavy metals in surface water in Kucuk Menderes River in Turkey, 2000-2002 Environ. Int. 2003, 29, 29-32 (Pubitemid 36336292)
2. Pinto, E., Sigaud-Kutner, T.C. S., Leitao, M. A. S., Okamoto, O. K., Morse, D., Colepicolo, P. Heavy metal-induced oxidative in algae J. Phycol. 2003, 39, 1008-1018
3. Kouba, A., Buric, M., Kozak, P. Bioaccumulation and effects of heavy metals in crayfish: A review Water, Air, Soil Pollut. 2010, 211, 5-16
4. Bernal, M., Ramiro, M. V., Cases, R., Rafael, P., Yruela, I. Excess copper effect on growth, chloroplast ultrastructure, oxygen-evolution activity and chlorophyll fluorescence in Glycine max cell suspensions Physiol. Plant. 2006, 127, 312-325 (Pubitemid 43799966)
5. Yatawara, M., Qi, S. H., Owago, O. J., Zhang, Y., Yang, D., Zhang, J. P., Burnet, J. E. Organochlorine pesticide and heavy metal residues in some edible biota collected from Quanzhou Bay and Xinghua Bay, Southeast China J. Envion. Sci-China 2010, 22, 314-320
6. Mansour, S. A., Gad, M. F. Risk assessment of pesticides and heavy metals contaminants in vegetables: A novel bioassay method using Daphnia Magna Straus. Food Chem. Toxicol. 2010, 48, 377-389
7. Garrison, A. W. Probing the enantioselectivity of chiral pesticides Environ. Sci. Technol. 2006, 40, 16-23 (Pubitemid 43069882)
8. Wen, Y. Z., Yuan, Y. L., Shen, C. S., Liu, H. J., Liu, W. P. Spectroscopic investigations of the chiral interactions between lipase and the herbicide dichlorprop Chirality 2009, 21, 396-401
9. Diao, J. L., Xu, P., Wang, P., Lu, Y. L., Lu, D. H., Zhou, Z. Q. Environmental behavior of the chiral aryloxyphenoxypropionate herbicide diclofop-methyl and diclofop: Enantiomerization and enantioselective degradation in soil Environ. Sci. Technol. 2010, 44, 2042-2047
10. Li, H., Yuan, Y. L., Shen, C. S., Wen, Y. Z., Liu, H. J. Enantioselectivity in toxicity and degradation of dichlorprop-methyl in algal cultures J. Envion. Sci. Health, Part B 2008, 43, 288-292 (Pubitemid 351595250)
11. Lewis, D. L., Garrison, A. W., Wommack, K. E., Whittemore, A., Steudler, P., Mellilo, J. Influence of environmental changes on degradation of chiral pollutants in soils Nature 1999, 401, 898-901 (Pubitemid 29518954)
12. Wen, Y. Z., Yuan, Y. L., Chen, H., Xu, D. M., Lin, K. D., Liu, W.P. Effect of chitosan on the enantioselective bioavailability of the herbicide dichlorprop to Chlorella pyrenoidosa Environ. Sci. Technol. 2010, 44, 4981-4987
13. Collen, J., Pedersen, M. A stress-induced oxidative burst in Eucheuma platycladum (Rhodophyta) Physiol. Plant. 1994, 92, 417-422 (Pubitemid 2162580)
14. Kupper, F. C., Kolareg, B., Guern, J., Potin, P. Oligoguluronates elicit an oxidative burst in the brown algal kelp Laminaria digitata Plant Physiol. 2001, 125, 278-291 (Pubitemid 32116766)
15. Camps, P., Perez, F., Soldevilla, N. R)- and (S)-3-hydroxy-4,4-dimethyl- 1-phenyl-2- pyrrolidinone as chiral auxiliaries in the enantioselective preparation of alpha-aryloxypropanoic acid herbicides and alpha-chlorocarboxylic acids Tetrahedron: Asymmetry 1998, 9, 2065-2079 (Pubitemid 28326438)
16. Knauert, S., Knauer, K. The role of reactive oxygen species in copper toxicity to two freshwater green algae J. Phycol. 2008, 44, 311-319 (Pubitemid 351548570)
17. Choo, K., Snoeijs, P., Pedersen, M. Oxidative stress tolerance in the filamentous green algae Cladophora glomerata and Enteromorpha ahlneriana J. Exp. Mar. Biol. Ecol. 2004, 298, 111-123 (Pubitemid 38069735)
18. Zahn, S., Canary, J. W. Electron-induced inversion of helical chirality in copper complexes of N, N -dialkylmethionines Science 2000, 288, 1404-1407 (Pubitemid 30366323)
19. Halliwell, B., Gutteridge, J. M. C. Free Radicals in Biology and Medicine; Oxford Univ. Press: New York, 1999; 3 nd ed, 936.
20. Gledhill, M., Nimmo, M., Hill, S. J. The toxicity of copper (II) species to marine algae with particular reference to macroalgae Phycol. 1997, 33, 2-11
21. Dorsey, J., Yentsch, C. M., Mayo, S., McKenna, C. Rapid analytical technique for the assessment of cell metabolic activity in marine microalgae Cytometry 1989, 10, 622-628
22. Cai, X. Y., Liu, W. P., Sheng, G. Y. Enantioselective degradation and ecotoxicity of the chiral herbicide diclofop in three freshwater alga cultures J. Agric. Food Chem. 2008, 56, 2139-2146
23. Florencea, T. M., Stauber, J. L. Toxicity of copper complexes to the marine diatom Nitzschia closterium Aquat. Toxicol. 1986, 8, 11-26 (Pubitemid 16071627)
24. Stauber, J. L., Florence, T. M. Mechanism of toxicity of ionic copper and copper complexes to algae Mar. Bio. 1987, 94, 511-519 (Pubitemid 17061512)
25. Blumerisinger, M., Meindl, D., Loos, E. Cell wall composition of chlorococcal algae Phytochemistry 1983, 22, 1603-1604
26. Loos, E., Meindl, D. Composition of the cell wall of Chlorella fusca Planta 1982, 156, 270-273
27. Ballan-Dufranais, C., Marcaillou, C., Amiard-Triquet, C. Response of the phytoplanktonic alga Tetraselmis suecica to copper and silver exposure: Vesicular metal bioaccumulation and lack of starch bodies Biol. Cell 1991, 72, 103-112
28. Nishikawa, K., Yamakoshi, Y., Uemura, I., Tominaga, N. Ultrastructural changes in Chlamydomonas acidophila (Chlorophyta) induced by heavy metals and polyphosphate metabolism Microb. Ecol. 2003, 44, 253-259 (Pubitemid 36423420)