Enantioselective toxicity of lactofen and its metabolites in Scenedesmus obliquus

Cheng, Cheng; Huang, Ledan; Ma, Rui; Zhou, Zhiqiang; Diao, Jinling

doi:10.1016/j.algal.2015.04.013

Cited by 37 publications

(21 citation statements)

References 46 publications

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“…When Scenedesmus obliqus was exposed to Rac-, S-, and R-lactofen, the CAT and SOD activities of algae in R-lactofen were higher than those of S-lactofen in general. And MDA content had also similar trend (Cheng et al 2015). These studies demonstrated that the data on enantioselective toxicity of chiral pesticides is necessary to improve the pesticide's safety in the environment.…”

Section: Discussionsupporting

confidence: 58%

Enantioselective effect of glufosinate on the growth of maize seedlings

Zhang

Cui

Yue

et al. 2018

Environ Sci Pollut Res

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Glufosinate is a non-selective chiral herbicide, which has been used extensively around the world. However, limited information on the enantioselectivity of Racand L-glufosinate against crops. In this study, the enantioselective effects on the growth, antioxidant, and targeted enzyme activities of maize seedlings of chiral glufosinate were investigated. The results showed the enantioselective growth inhibitions were observed at both 1 and 5 mg/L concentration levels. L-Glufosinate induced more growth rate reduction in shoot height and weight compared to Rac-glufosinate. All of the antioxidant enzyme activities increased obviously in the leaves of maize seedlings treated by 1 mg/L of glufosinate. Superoxide dismutase (SOD) activity, catalase (CAT) activity, peroxidase (POD) activity, glutathione reductase (GR) activity, and malondialdehyde (MDA) content induced by L-glufosinate were 1.36, 1.16, 1.51, 1.65, and 1.65 times higher than those by Rac-glufosinate, respectively Notably, the glutamine synthetase (GS) activity was significantly reduced to 80% and 57% in the control group at 1 mg/L treated with Racand L-glufosinate, respectively. Our results indicated that Racand L-glufosinate showed the obvious enantioselectivity in the growth of maize seedlings, which has shed light on the potential enantioselective phytotoxicity of glufosinate. Data provided here will be helpful to develop the environmentally friendly herbicides.

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Section: Discussionsupporting

confidence: 58%

Enantioselective effect of glufosinate on the growth of maize seedlings

Zhang

Cui

Yue

et al. 2018

Environ Sci Pollut Res

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“…This is in accordance with the findings of Zhang et al, who reported that cyproconazole enhanced the chlorophyll a level in C. pyrenoidosa at low concentrations. In addition, Cheng et al also found that low lactofen levels increased the content of chlorophyll a in S. obliquus . This induced effect may result from the algae using furalaxyl as a source of carbon and nitrogen .…”

Section: Resultsmentioning

confidence: 93%

“…Besides, the C. pyrenoidosa was more sensitive to enantiomer‐1 than enantiomer‐2. Cheng et al compared the enantiomeric toxicities of lactofen and desethyl lactofen to S. obliquus , and the order of acute toxicity was (R)‐(−) ‐enantiomer > racemate > (S)‐(+) ‐enantiomer. Therefore, the present data available on the toxicity of the racemic mixture are not reliable, and the study of enantioselective toxicity of chiral pesticides has been very popular for environmental safety issues …”

Section: Resultsmentioning

confidence: 99%

Enantioselective toxic effects and digestion of furalaxyl enantiomers in Scenedesmus obliquus

Cheng

et al. 2018

Chirality

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Research on the enantioselective environmental behavior of chiral pesticides has been a hot spot of environmental chemistry recently. In this study, the acute toxicity and digestion of furalaxyl enantiomers were determined on the aquatic algae Scendesmus obliquus. After exposure for 96 hours, the EC50 values for (S)‐furalaxyl and (R)‐furalaxyl were 13.59 and 15.26 mg/L, respectively. In addition, enantioselectivity was observed from the determined chlorophyll contents and antioxidant enzyme (CAT and SOD) activities of algae cells after exposure to furalaxyl enantiomers for 96 hours. The digestion rate of (S)‐furalaxyl and (R)‐furalaxyl were almost the same in S. obliquus. On the basis of these data, the inactive enantiomers (S)‐ furalaxyl is more toxic than the active one on the non‐target species S. obliquus, indicating that such enantiomeric differences should be taken into consideration in the study of pesticide risk assessment.

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“…The esterase LacH that was cloned from strain LY-2 was responsible for converting lactofen to acifluorfen. Cheng et al [ 25 ] studied the acute toxicity of lactofen and its metabolite acifluorfen in the aquatic algae Scenedesmus obliquus , and the results indicated that the toxicity of the acifluorfen was lower than that of the lactofen. Wang et al [ 26 ] evaluated the toxic effects of the herbicide lactofen and acifluorfen to the aquatic plant Lemna minor , and they found L. minor growth was inhibited in the order of lactofen > acifluorfen.…”

Section: Discussionmentioning

confidence: 99%

Biochemical characterization of an enantioselective esterase from Brevundimonas sp. LY-2

Zhang

Zhao

et al. 2017

Microb Cell Fact

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BackgroundLactofen, a member of the diphenylether herbicides, has high activity and is commonly used to control broadleaf weeds. As a post-emergent herbicide, it is directly released to the environment, and easily caused the pollution. This herbicide is degraded in soil mainly by microbial activity, but the functional enzyme involved in the biodegradation of lactofen is still not clear now.ResultsA novel esterase gene lacH, involved in the degradation of lactofen, was cloned from the strain Brevundimonas sp. LY-2. The gene contained an open reading frame of 921 bp, and a putative signal peptide at the N-terminal was identified with the most likely cleavage site between Ala 28 and Ala 29. The encoded protein, LacH, could catalyze the hydrolysis of lactofen to form acifluorfen. Phylogenetic analysis showed that LacH belong to family V of bacterial lipolytic enzymes. Biochemical characterization analysis showed that LacH was a neutral esterase with an optimal pH of 7.0 and an optimal temperature of 40 °C toward lactofen. Besides, the activity of LacH was strongly inhibited by Hg2+ and Zn2+. LacH preferred short chain p-nitrophenyl esters (C2–C6), exhibited maximum activity toward p-nitrophenyl acetate. Furthermore, the enantioselectivity of LacH during lactofen hydrolysis was also studied, and the results show that R-(−)-lactofen was degraded faster than S-(+)-lactofen, indicating the occurrence of enantioselectivity in the enzymatic reaction.ConclusionsOur studies characterized a novel esterase involved in the biodegradation of diphenylether herbicide lactofen. The esterase showed enantioselectivity during lactofen degradation, which revealed the occurrence of enzyme-mediated enantioselective degradation of chiral herbicides.Electronic supplementary materialThe online version of this article (doi:10.1186/s12934-017-0727-4) contains supplementary material, which is available to authorized users.

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Enantioselective toxicity of lactofen and its metabolites in Scenedesmus obliquus

Cited by 37 publications

References 46 publications

Enantioselective effect of glufosinate on the growth of maize seedlings

Enantioselective effect of glufosinate on the growth of maize seedlings

Enantioselective toxic effects and digestion of furalaxyl enantiomers in Scenedesmus obliquus

Biochemical characterization of an enantioselective esterase from Brevundimonas sp. LY-2

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