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Article ; Online: Biodegradation of sulfoxaflor and photolysis of sulfoxaflor by ultraviolet radiation.

Zhao, Yun-Xiu / Chen, Ke-Xin / Wang, Li / Yuan, Pan-Pan / Dai, Yi-Jun

2023 Volume 34, Issue 4, Page(s) 341–355

Abstract: Sulfoxaflor (SUL, [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl] ethyl]- ... ...

Abstract	Sulfoxaflor (SUL, [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl] ethyl]-λ
MeSH term(s)	Ultraviolet Rays ; Photolysis ; Insecticides/chemistry ; Insecticides/metabolism ; Biodegradation, Environmental
Chemical Substances	sulfoxaflor (671W88OY8K) ; Insecticides
Language	English
Publishing date	2023-02-18
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1056014-2
ISSN	1572-9729 ; 0923-9820
ISSN (online)	1572-9729
ISSN	0923-9820
DOI	10.1007/s10532-023-10020-x
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Zs.A 3094: Show issues

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Article ; Online: Asp-tRNA

Yu, Xue-Xiu / Chen, Ke-Xin / Yuan, Pan-Pan / Wang, Yu-He / Li, Hua-Xiao / Zhao, Yun-Xiu / Dai, Yi-Jun

The Science of the total environment

2024 Volume 928, Page(s) 172479

Abstract: The main metabolic product of the pyridinecarboxamide insecticide flonicamid, N-(4-trifluoromethylnicotinyl)glycinamide (TFNG-AM), has been shown to have very high mobility in soil, leading to its accumulation in the environment. Catabolic pathways of ... ...

Abstract	The main metabolic product of the pyridinecarboxamide insecticide flonicamid, N-(4-trifluoromethylnicotinyl)glycinamide (TFNG-AM), has been shown to have very high mobility in soil, leading to its accumulation in the environment. Catabolic pathways of flonicamid have been widely reported, but few studies have focused on the metabolism of TFNG-AM. Here, the rapid transformation of TFNG-AM and production of the corresponding acid product N-(4-trifluoromethylnicotinoyl) glycine (TFNG) by the plant growth-promoting bacterium Variovorax boronicumulans CGMCC 4969 were investigated. With TFNG-AM at an initial concentration of 0.86 mmol/L, 90.70 % was transformed by V. boronicumulans CGMCC 4969 resting cells within 20 d, with a degradation half-life of 4.82 d. A novel amidase that potentially mediated this transformation process, called AmiD, was identified by bioinformatic analyses. The gene encoding amiD was cloned and expressed recombinantly in Escherichia coli, and the enzyme AmiD was characterized. Key amino acid residue Val154, which is associated with the catalytic activity and substrate specificity of signature family amidases, was identified for the first time by homology modeling, structural alignment, and site-directed mutagenesis analyses. When compared to wild-type recombinant AmiD, the mutant AmiD V154G demonstrated a 3.08-fold increase in activity toward TFNG-AM. The activity of AmiD V154G was greatly increased toward aromatic L-phenylalanine amides, heterocyclic TFNG-AM and IAM, and aliphatic asparagine, whereas it was dramatically lowered toward benzamide, phenylacetamide, nicotinamide, acetamide, acrylamide, and hexanamid. Quantitative PCR analysis revealed that AmiD may be a substrate-inducible enzyme in V. boronicumulans CGMCC 4969. The mechanism of transcriptional regulation of AmiD by a member of the AraC family of regulators encoded upstream of the amiD gene was preliminarily investigated. This study deepens our understanding of the mechanisms of metabolism of toxic amides in the environment, providing new ideas for microbial bioremediation.
MeSH term(s)	Insecticides/metabolism ; Comamonadaceae/metabolism ; Comamonadaceae/genetics ; Amidohydrolases/metabolism ; Amidohydrolases/genetics ; Biodegradation, Environmental ; Nicotinic Acids/metabolism ; Niacinamide/analogs & derivatives
Chemical Substances	Insecticides ; Amidohydrolases (EC 3.5.-) ; flonicamid (9500W2Z53J) ; amidase (EC 3.5.1.4) ; Nicotinic Acids ; Niacinamide (25X51I8RD4)
Language	English
Publishing date	2024-04-14
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	121506-1
ISSN	1879-1026 ; 0048-9697
ISSN (online)	1879-1026
ISSN	0048-9697
DOI	10.1016/j.scitotenv.2024.172479
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Article ; Online: Biodegradation of the pyridinecarboxamide insecticide flonicamid by Microvirga flocculans and characterization of two novel amidases involved.

Zhao, Yun-Xiu / Guo, Ling / Wang, Li / Jiang, Neng-Dang / Chen, Ke-Xin / Dai, Yi-Jun

Ecotoxicology and environmental safety

2021 Volume 220, Page(s) 112384

Abstract: Flonicamid (N-cyanomethyl-4-trifluoromethylnicotinamide, FLO) is a new type of pyridinecarboxamide insecticide that exhibits particularly good efficacy in pest control. However, the extensive use of FLO in agricultural production poses environmental ... ...

Abstract	Flonicamid (N-cyanomethyl-4-trifluoromethylnicotinamide, FLO) is a new type of pyridinecarboxamide insecticide that exhibits particularly good efficacy in pest control. However, the extensive use of FLO in agricultural production poses environmental risks. Hence, its environmental behavior and degradation mechanism have received increasing attention. Microvirga flocculans CGMCC 1.16731 rapidly degrades FLO to produce the intermediate N-(4-trifluoromethylnicotinoyl) glycinamide (TFNG-AM) and the end acid metabolite 4-(trifluoromethyl) nicotinol glycine (TFNG). This bioconversion is mediated by the nitrile hydratase/amidase system; however, the amidase that is responsible for the conversion of TFNG-AM to TFNG has not yet been reported. Here, gene cloning, overexpression in Escherichia coli and characterization of pure enzymes showed that two amidases-AmiA and AmiB-hydrolyzed TFNG-AM to TFNG. AmiA and AmiB showed only 20-30% identity to experimentally characterized amidase signature family members, and represent novel amidases. Compared with AmiA, AmiB was more sensitive to silver and copper ions but more resistant to organic solvents. Both enzymes demonstrated good pH tolerance and exhibited broad amide substrate specificity. Homology modeling suggested that residues Asp191 and Ser195 may strongly affect the catalytic activity of AmiA and AmiB, respectively. The present study furthers our understanding of the enzymatic mechanisms of biodegradation of nitrile-containing insecticides and may aid in the development of a bioremediation agent for FLO.
MeSH term(s)	Amidohydrolases/metabolism ; Bacterial Proteins/genetics ; Bacterial Proteins/metabolism ; Biodegradation, Environmental ; Gene Expression Regulation, Bacterial/physiology ; Gene Expression Regulation, Enzymologic ; Insecticides/chemistry ; Insecticides/metabolism ; Methylobacteriaceae/metabolism ; Niacinamide/analogs & derivatives ; Niacinamide/metabolism
Chemical Substances	Bacterial Proteins ; Insecticides ; Niacinamide (25X51I8RD4) ; flonicamid (9500W2Z53J) ; Amidohydrolases (EC 3.5.-)
Language	English
Publishing date	2021-06-03
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	436536-7
ISSN	1090-2414 ; 0147-6513
ISSN (online)	1090-2414
ISSN	0147-6513
DOI	10.1016/j.ecoenv.2021.112384
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Article: Nitroreduction of imidacloprid by the actinomycete Gordonia alkanivorans and the stability and acute toxicity of the nitroso metabolite

Cheng, Xi / Chen, Ke-xin / Jiang, Neng-dang / Wang, Li / Jiang, Huo-yong / Zhao, Yun-xiu / Dai, Zhi-ling / Dai, Yi-jun

Chemosphere. 2022 Mar., v. 291

2022

Abstract: The insecticide imidacloprid (IMI), which is used worldwide, pollutes environments and has significant ecotoxicological effects. Microbial metabolism and photolysis are the major pathways of IMI degradation in natural environments. Several studies have ... ...

Abstract	The insecticide imidacloprid (IMI), which is used worldwide, pollutes environments and has significant ecotoxicological effects. Microbial metabolism and photolysis are the major pathways of IMI degradation in natural environments. Several studies have reported that the metabolites of IMI nitroreduction are more toxic to some insects and mammals than IMI itself. Thus, environmental degradation of IMI may enhance the ecotoxicity of IMI and have adverse effects on non-target organisms. Here, we report that an actinomycete—Gordonia alkanivorans CGMCC 21704—transforms IMI to a nitroreduction metabolite, nitroso IMI. Resting cells of G. alkanivorans at OD₆₀₀ ₙₘ = 10 transformed 95.7% of 200 mg L⁻¹ IMI to nitroso IMI in 4 d. Nitroso IMI was stable at pH 4–9. However, it rapidly degraded under sunlight via multiple oxidation, dehalogenation, and oxidative cleavage reactions to form 10 derivatives; the half-life of nitroso IMI in photolysis was 0.41 h, compared with 6.19 h for IMI. Acute toxicity studies showed that the half maximal effective concentration (EC₅₀) values of IMI, nitroso IMI, and its photolytic metabolites toward the planktonic crustacean Daphnia magna for immobilization (exposed to the test compounds for 48 h) were 17.70, 9.38, 8.44 mg L⁻¹, respectively. The half-life of nitroso IMI in various soils was also examined. The present study reveals that microbial nitroreduction accelerates IMI degradation and the nitroso IMI is easily decomposed by sunlight and in soil. However, nitroso IMI and its photolytic products have higher toxicity toward D. magna than the parent compound IMI, and therefore increase the ecotoxicity of IMI.
Keywords	Daphnia magna ; acute toxicity ; dehalogenation ; ecotoxicology ; environmental degradation ; half life ; imidacloprid ; median effective concentration ; metabolism ; metabolites ; oxidation ; pH ; photolysis ; plankton ; soil ; solar radiation
Language	English
Dates of publication	2022-03
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	120089-6
ISSN	1879-1298 ; 0045-6535 ; 0366-7111
ISSN (online)	1879-1298
ISSN	0045-6535 ; 0366-7111
DOI	10.1016/j.chemosphere.2021.132885
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Article ; Online: A "Pre-Division Metal Clusters" Strategy to Mediate Efficient Dual-Active Sites ORR Catalyst for Ultralong Rechargeable Zn-Air Battery.

Zhao, Yun-Xiu / Wen, Jing-Hong / Li, Ping / Zhang, Peng-Fang / Wang, Su-Na / Li, Da-Cheng / Dou, Jian-Min / Li, Yun-Wu / Ma, Hui-Yan / Xu, Liqiang

Angewandte Chemie (International ed. in English)

2023 Volume 62, Issue 11, Page(s) e202216950

Abstract: To conquer the bottleneck of sluggish kinetics in cathodic oxygen reduction reaction (ORR) of metal-air batteries, catalysts with dual-active centers have stood out. Here, a "pre-division metal clusters" strategy is firstly conceived to fabricate a N,S- ... ...

Abstract	To conquer the bottleneck of sluggish kinetics in cathodic oxygen reduction reaction (ORR) of metal-air batteries, catalysts with dual-active centers have stood out. Here, a "pre-division metal clusters" strategy is firstly conceived to fabricate a N,S-dual doped honeycomb-like carbon matrix inlaid with CoN
Language	English
Publishing date	2023-01-25
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202216950
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Article ; Online: Bioinformatics of a Novel Nitrile Hydratase Gene Cluster of the N

Zhao, Yun-Xiu / Yang, Wen-Long / Guo, Ling / Jiang, Huo-Yong / Cheng, Xi / Dai, Yi-Jun

Journal of agricultural and food chemistry

2020 Volume 68, Issue 35, Page(s) 9299–9307

Abstract: Microvirga ... ...

Abstract	Microvirga flocculans
MeSH term(s)	Amino Acid Sequence ; Bacterial Proteins/chemistry ; Bacterial Proteins/genetics ; Bacterial Proteins/metabolism ; Computational Biology ; Hydro-Lyases/chemistry ; Hydro-Lyases/genetics ; Hydro-Lyases/metabolism ; Kinetics ; Methylobacteriaceae/chemistry ; Methylobacteriaceae/enzymology ; Methylobacteriaceae/genetics ; Methylobacteriaceae/physiology ; Multigene Family ; Nitriles/chemistry ; Nitriles/metabolism ; Nitrogen Fixation ; Phylogeny ; Sequence Alignment
Chemical Substances	Bacterial Proteins ; Nitriles ; Hydro-Lyases (EC 4.2.1.-) ; nitrile hydratase (EC 4.2.1.-)
Language	English
Publishing date	2020-08-20
Publishing country	United States
Document type	Journal Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.0c03702
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Article: Bioinformatics of a Novel Nitrile Hydratase Gene Cluster of the N₂-Fixing Bacterium Microvirga flocculans CGMCC 1.16731 and Characterization of the Enzyme

Zhao, Yun-Xiu / Yang, Wen-Long / Guo, Ling / Jiang, Huo-Yong / Cheng, Xi / Dai, Yi-Jun

Journal of agricultural and food chemistry. 2020 Aug. 10, v. 68, no. 35

2020

Abstract: Microvirga flocculans CGMCC 1.16731 can degrade many cyano group-containing neonicotinoid insecticides. Here, its genome was sequenced, and a novel nitrile hydratase gene cluster was discovered in a plasmid. The NHase gene cluster (pnhF) has gene ... ...

Abstract	Microvirga flocculans CGMCC 1.16731 can degrade many cyano group-containing neonicotinoid insecticides. Here, its genome was sequenced, and a novel nitrile hydratase gene cluster was discovered in a plasmid. The NHase gene cluster (pnhF) has gene structure β-subunit 1, α-subunit, and β-subunit 2, which is different from previously reported NHase gene structures. Phylogenetic analysis of α-subunits indicated that NHases containing the three subunit (β1αβ2) structure are independent from NHases containing two subunits (αβ). pnhF was successfully expressed in Escherichia coli, and the purified PnhF could convert the nitrile-containing insecticide flonicamid to N-(4-trifluoromethylnicotinoyl)glycinamide. The enzymatic properties of PnhF were investigated using flonicamid as a substrate. Homology models revealed that amino acid residue β1-Glu56 may strongly affect the catalytic activity of PnhF. This study expands our understanding of the structures and functions of NHases and the enzymatic mechanism of the environmental fate of flonicamid.
Keywords	Escherichia coli ; amino acids ; bacteria ; bioinformatics ; catalytic activity ; environmental fate ; flonicamid ; food chemistry ; multigene family ; nitrile hydratase ; phylogeny ; plasmids
Language	English
Dates of publication	2020-0810
Size	p. 9299-9307.
Publishing place	American Chemical Society
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.0c03702
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Article ; Online: Biodegradation of flonicamid by Ensifer adhaerens CGMCC 6315 and enzymatic characterization of the nitrile hydratases involved.

Zhao, Yun-Xiu / Wang, Li / Chen, Ke-Xin / Jiang, Neng-Dang / Sun, Shi-Lei / Ge, Feng / Dai, Yi-Jun

Microbial cell factories

2021 Volume 20, Issue 1, Page(s) 133

Abstract: Background: Flonicamid (N-cyanomethyl-4-trifluoromethylnicotinamide, FLO) is a new type of pyridinamide insecticide that regulates insect growth. Because of its wide application in agricultural production and high solubility in water, it poses potential ...

Abstract	Background: Flonicamid (N-cyanomethyl-4-trifluoromethylnicotinamide, FLO) is a new type of pyridinamide insecticide that regulates insect growth. Because of its wide application in agricultural production and high solubility in water, it poses potential risks to aquatic environments and food chain. Results: In the present study, Ensifer adhaerens CGMCC 6315 was shown to efficiently transform FLO into N-(4-trifluoromethylnicotinoyl) glycinamide (TFNG-AM) via a hydration pathway mediated by two nitrile hydratases, PnhA and CnhA. In pure culture, resting cells of E. adhaerens CGMCC 6315 degraded 92% of 0.87 mmol/L FLO within 24 h at 30 °C (half-life 7.4 h). Both free and immobilized (by gel beads, using calcium alginate as a carrier) E. adhaerens CGMCC 6315 cells effectively degraded FLO in surface water. PnhA has, to our knowledge, the highest reported degradation activity toward FLO, V Conclusions: Application of E. adhaerens may be a good strategy for bioremediation of FLO in surface water. This work furthers our understanding of the enzymatic mechanisms of biodegradation of nitrile-containing insecticides and provides effective transformation strategies for microbial remediation of FLO contamination.
MeSH term(s)	Bacterial Proteins/metabolism ; Biodegradation, Environmental ; Hydro-Lyases/metabolism ; Insecticides/metabolism ; Niacinamide/analogs & derivatives ; Niacinamide/metabolism ; Nitriles/metabolism ; Rhizobiaceae/enzymology ; Rhizobiaceae/metabolism
Chemical Substances	Bacterial Proteins ; Insecticides ; Nitriles ; Niacinamide (25X51I8RD4) ; flonicamid (9500W2Z53J) ; Hydro-Lyases (EC 4.2.1.-) ; nitrile hydratase (EC 4.2.1.-)
Language	English
Publishing date	2021-07-13
Publishing country	England
Document type	Journal Article
ISSN	1475-2859
ISSN (online)	1475-2859
DOI	10.1186/s12934-021-01620-4
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Article ; Online: Nitroreduction of imidacloprid by the actinomycete Gordonia alkanivorans and the stability and acute toxicity of the nitroso metabolite.

Cheng, Xi / Chen, Ke-Xin / Jiang, Neng-Dang / Wang, Li / Jiang, Huo-Yong / Zhao, Yun-Xiu / Dai, Zhi-Ling / Dai, Yi-Jun

Chemosphere

2021 Volume 291, Issue Pt 2, Page(s) 132885

Abstract	The insecticide imidacloprid (IMI), which is used worldwide, pollutes environments and has significant ecotoxicological effects. Microbial metabolism and photolysis are the major pathways of IMI degradation in natural environments. Several studies have reported that the metabolites of IMI nitroreduction are more toxic to some insects and mammals than IMI itself. Thus, environmental degradation of IMI may enhance the ecotoxicity of IMI and have adverse effects on non-target organisms. Here, we report that an actinomycete-Gordonia alkanivorans CGMCC 21704-transforms IMI to a nitroreduction metabolite, nitroso IMI. Resting cells of G. alkanivorans at OD
MeSH term(s)	Actinobacteria ; Animals ; Insecticides/toxicity ; Neonicotinoids/toxicity ; Nitro Compounds/toxicity
Chemical Substances	Insecticides ; Neonicotinoids ; Nitro Compounds ; imidacloprid (3BN7M937V8)
Language	English
Publishing date	2021-11-11
Publishing country	England
Document type	Journal Article
ZDB-ID	120089-6
ISSN	1879-1298 ; 0045-6535 ; 0366-7111
ISSN (online)	1879-1298
ISSN	0045-6535 ; 0366-7111
DOI	10.1016/j.chemosphere.2021.132885
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Article ; Online: Bioconversion of indole-3-acetonitrile by the N

Zhao, Yun-Xiu / Guo, Lei-Lei / Sun, Shi-Lei / Guo, Jing-Jing / Dai, Yi-Jun

International microbiology : the official journal of the Spanish Society for Microbiology

2019 Volume 23, Issue 2, Page(s) 225–232

Abstract: ... An ... ...

Abstract	An N
MeSH term(s)	Bacterial Proteins/biosynthesis ; Bacterial Proteins/metabolism ; Biodegradation, Environmental ; Environmental Pollutants/metabolism ; Escherichia coli/metabolism ; Hydro-Lyases/biosynthesis ; Hydro-Lyases/metabolism ; Indoleacetic Acids/metabolism ; Indoles/metabolism ; Insecticides/metabolism ; Recombinant Proteins/biosynthesis ; Recombinant Proteins/metabolism ; Rhizobiaceae/enzymology
Chemical Substances	Bacterial Proteins ; Environmental Pollutants ; Indoleacetic Acids ; Indoles ; Insecticides ; Recombinant Proteins ; indoleacetamide (879-37-8) ; indole-3-acetonitrile (AG97OFW8JW) ; Hydro-Lyases (EC 4.2.1.-) ; nitrile hydratase (EC 4.2.1.-)
Language	English
Publishing date	2019-08-13
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1454951-7
ISSN	1618-1905 ; 1139-6709
ISSN (online)	1618-1905
ISSN	1139-6709
DOI	10.1007/s10123-019-00094-0
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