Enantioselective separation and zebrafish embryo toxicity of insecticide beta-cypermethrin.
Enantioselectivity of chiral pollutants is receiving growing concern due to the difference in toxicology and environment fate between enantiomers. In this study, enantiomers of insecticide beta-cypermethrin (beta-CP) were separated on selected chiral column by HPLC, and the toxicity of enantiomers was evaluated using the zebrafish embryo-larval assays. The enantiomers of beta-CP were baseline separated on Chiralcel OD and Chiralpak AD columns and detected by circular dichroism (CD) at 236 nm. Better separation could be achieved at lower temperature (e.g., 20 degrees C) and with lower levels of polar modifiers. Pure enantiomers were obtained on Chiralcel OD. The CD spectra of enantiomers were recorded. By comparing the elution order with a previous similar study, the absolute configuration of beta-CP enantiomers was determined. The individual enantiomers were used in zebrafish embryo test, and the results showed that beta-CP enantioselectively induced yolk sac edema, pericardial edema and crooked body. The IR-cis-alphaS and 1R-trans-alphaS enantiomers showed strong developmental toxicities at concentration of 0.1 mg/L, while the 1S-cis-alphaR and 1S-trans-alphaR induced no malformations at higher concentration (e.g., 0.3 mg/L). The results suggest that the enantioselective toxicological effects of beta-CP should be considered when evaluating its ecotoxicological effects.
Xu
Chao
C
Research Center of Environmental Science, College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310032, China. chaoxu@zjut.edu.cn
Tu
Wenqing
W
Lou
Chun
C
Hong
Yingying
Y
Zhao
Meirong
M
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004625:Embryo, Nonmammalian / Q000002:abnormalities / Q000187:drug effects*; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D011722:Pyrethrins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D013237:Stereoisomerism; D013696:Temperature; D018675:Toxicity Tests / Q000379:methods*; D015027:Zebrafish / Q000196:embryology* / Q000378:metabolism*
D007306:Insecticides; D011722:Pyrethrins; C017160:cypermethrin