title: Enantioselective toxic effects and biodegradation of benalaxyl in Scenedesmus obliquus.
abstract: Enantioselectivity in ecotoxicity and biodegradation of chiral pesticide benalaxyl to freshwater algae Scenedesmus obliquus was studied. The 96 h-EC(50) values of rac-, R-(-)-, S-(+)-benalaxyl were 2.893, 3.867, and 8.441 mg L(-1), respectively. Therefore, the acute toxicities of benalaxyl enantiomers were enantioselective. In addition, the pigments chlorophyll a and chlorophyll b, antioxidant enzyme activities catalase (CAT) and superoxide dismutase (SOD) as well as lipid peroxide malondialdehyde (MDA) were determined to evaluate the different toxic effects. Chlorophyll a was induced by S-(+)-benalaxyl but inhibited by R-(-)-benalaxyl at 1 mg L(-1). Chlorophyll b were both induced at 1 mg L(-1), but S-(+)-form was fourfold higher than R-(-)-form. S-(+)-benalaxyl inhibited more CAT activities at 3 mg L(-1) and 5 mg L(-1), induced less SOD activity and MDA content at 5 mg L(-1) than R-(-)-benalaxyl. Based on these data, enantioselectivity occurred in anti-oxidative stress when S. obliquus response to benalaxyl. In the biodegradation experiment, the half-lives of S-(+)-benalaxyl and R-(-)-benalaxyl were 4.07 d and 5.04 d, respectively, resulting in relative enrichment of the R-(-)-form. These results showed that toxic effects and biodegradation of benalaxyl in S. obliquus were enantioselective, and such enantiomeric differences must be taken into consideration in pesticide risk.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, PR China.
authors.forename: Ledan
authors.initials: L
authors.lastname: Huang
authors.forename: Dahai
authors.initials: D
authors.lastname: Lu
authors.forename: Jinling
authors.initials: J
authors.lastname: Diao
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Zhou
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000378:metabolism / Q000633:toxicity; D001673:Biodegradation, Environmental; D002734:Chlorophyll / Q000378:metabolism; D008315:Malondialdehyde / Q000378:metabolism; D010575:Pesticides / Q000378:metabolism / Q000633:toxicity*; D044444:Scenedesmus / Q000187:drug effects* / Q000254:growth & development / Q000378:metabolism; D013237:Stereoisomerism; D014874:Water Pollutants, Chemical / Q000378:metabolism / Q000633:toxicity
chemical_list: D010575:Pesticides; D014874:Water Pollutants, Chemical; D002734:Chlorophyll; C052866:benalaxyl; D008315:Malondialdehyde; D000409:Alanine