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cypermethrin
PEST MANAGEMENT SCIENCE · 2020 ·Vol. 77 ·期 4 ·2129-2141 · IF 3.75

Enhanced hydrolysis of β-cypermethrin caused by deletions in the glycin-rich region of carboxylesterase 001G from Helicoverpa armigera

Li-Sha Bai,Jing-Jing Xu,Cai-Xia Zhao,Ya-Li Chang,Yan-Ling Dong,Kai-Ge Zhang,Yong-Qiang Li,Yi-Ping Li,Zhi-Qing Ma,Xi-Li Liu

BACKGROUND Carboxylesterase (CarE) is a major class of enzyme involved in the detoxification of toxic xenobiotics in various insect species. Previous work has shown that the carboxylesterase gene CarE001G found in Helicoverpa armigera is more active and can metabolize synthesized pyrethroids, such as β -cypermethrin, one of the commonly used commercial insecticides for lepidopteran pest control. In addition, CarE001G is very special as it has a very specific glycine-rich region located adjacent to its C-terminal. But whether mutations in this unique sequence can change the biochemistry and function of CarE001G are unknown. RESULTS In this study, four variants of CarE001G with different deletions in the glycine-rich region were obtained and functionally expressed in Escherichia coli . The recombinant proteins were purified and confirmed by Western blot and mass spectrometry analyses. These mutant enzymes showed high catalytic efficiency toward the model substrate α -naphthyl acetate. Inhibition study showed that β -cypermethrin had relatively strong inhibition on CarE activities. In vitro metabolism assay showed that the mutant enzymes significantly enhanced their metabolic activities toward β -cypermethrin with specific activities between 4.0 and 5.6 nmol L -1 min −1 mg −1 protein. Molecular docking analyses consistently demonstrated that deletion mutations in the glycine-rich region may facilitate the anchoring of the β -cypermethrin molecule in the active binding pocket of the mutant enzymes. CONCLUSION The data show that deletion mutations can cause qualitative change in the capacity of CarEs in the detoxification of β -cypermethrin. This indicates that deletion mutations in the glycine-rich region may have the potential to cause synthesized pyrethroid (SP) resistance in H. armigera in the future. © 2020 Society of Chemical Industry

研究领域: 昆虫学 · 分子生物学 · 农药毒理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY · 2017 · IF 3.743

Effects of α-cypermethrin enantiomers on the growth, biochemical parameters and bioaccumulation in Rana nigromaculata tadpoles of the anuran amphibians

Peng Xu,Ledan Huang

Populations of many amphibian species are declining worldwide in part because of pesticide contamination. As a surface water contaminant, α-cypermethrin may have severe ecological impacts on amphibians. Here, we examined the acute toxicity of α-cypermethrin enantiomers to dark-spotted frog Rana nigromaculata tadpoles at 24, 48, 72 and 96   h, finding that the tadpoles were indeed sensitive to α-cypermethrin. The (S)-(1R, 3R)-enantiomer was approximately 29 times more toxic than the (R)-(1S, 3S)-enantiomer at 96   h. A significant delayed growth in R. nigromaculata tadpoles after exposure to 0.5   µg   L −1 of S-(1R, 3R)-cypermethrin was observed. Additionally, increased superoxide dismutase (SOD), catalase (CAT), glutathione-S-transferase (GST) and malondialdehyde (MDA) levels indicate the presence of oxidative stress in the tadpoles. Further, tadpoles exposed to sublethal concentrations of α-cypermethrin enantiomers exhibited enantioselective growth and oxidative damage. Bioaccumulation experiments showed that the tadpoles could rapidly accumulate α-cypermethrin. The (R)-(1S, 3S)-enantiomer was preferentially accumulated over the (S)-(1R, 3R)-enantiomer, and it was also eliminated more quickly, as evidenced in the subsequent depuration experiments.

CAS / MDL: 67375-30-8
研究领域: 环境科学 · 毒理学 · 生态学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF HAZARDOUS MATERIALS · 2023 · IF 13.6

Exposure to cypermethrin pesticide disturbs the microbiome and disseminates antibiotic resistance genes in soil and the gut of Enchytraeus crypticus

Ming-Kang Jin,Qi Zhang,Yu-Tian Yang,Cai-Xia Zhao,Jian Li,Hongjie Li,Haifeng Qian,Dong Zhu,Yong-Guan Zhu

Worldwide, pyrethroids , such as cypermethrin, are the second most applied group of insecticides, however, their effects on the soil microbiome and non-target soil fauna remain largely unknown. Herein, we assessed the change of bacterial communities and antibiotic resistance genes (ARGs) of soil and in the gut of the model soil species Enchytraeus crypticus using a combination of 16S rRNA gene amplicon sequencing, and high-throughput qPCR of ARGs. Results indicate that cypermethrin exposure enriches potential pathogens (e.g. Bacillus anthracis ) in the soil and gut microbiome of E. crypticus , heavily disrupting the latter’s microbiome structure, and even disrupts activities of the E. crypticus immune system. The co-occurrence of potential pathogens (e.g. Acinetobacter baumannii ), ARGs, and mobile genetic elements (MGEs) revealed the increased risk of pathogenicity as well as antibiotic resistance in potential pathogens. Moreover, structural equation modeling demonstrated that the dissemination of ARGs was not only promoted by MGEs, but also by the ratio of the core to non-core bacterial abundance. Collectively, these results provide an in-depth view of the previously unappreciated environmental risk of cypermethrin on the dissemination of ARGs in the soil and non-target soil fauna.

CAS / MDL: 52315-07-8
研究领域: 环境科学 · 微生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2024 · IF 8

Ga-doped carbon quantum dot-sensitized luminol molecularly imprinted electrochemiluminescence sensor used for the efficient detection of cypermethrin in aquatic products

Jinjie You,Rui Chen,Qiaofen Pan,Zeming Zhang,Aili Sun,Rongrong Zhang,Hua Liu,Xizhi Shi

The development of new electrochemical sensitizing materials is crucial for rapid detection technology. In this study, gallium-doped carbon quantum dots (Ga@CQDs) were synthesized using a one-pot hydrothermal approach to serve as coreactant for luminol. A molecular-imprinted electroluminescence sensor was prepared for rapid, sensitive cypermethrin (CYP) detection using in-situ electrodeposition. Ga doping reduces CQDs' band gap, boosts conductivity and catalysis, and enhances luminol's ECL signal. The advancement in molecular imprinting technology significantly enhances the sensor's ability to selectively detect CYP, while also providing robust interference resistance. The ECL intensity of the sensor correlated linearly with CYP concentration (0.05–100 μM) under optimal conditions (R 2 = 0.9912, LOD= 0.03 μM). In practical applications, recovery rates of water and aquatic product samples ranged from 86.4 % to 98.0 %, with RSD that did not exceed 8.13 %. A Ga@CQDs-based luminol sensitizing system for molecularly imprinted electrochemical sensors provides a solution for fast, sensitive CYP detection in environmental and aquatic products.

研究领域: 分析化学 · 环境科学 · 食品安全
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ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH · 2022 ·Vol. 30 ·期 2 ·2665-2675 · IF 5.19

Perinatal exposure to low doses of cypermethrin induce the puberty-related hormones and decrease the time to puberty in the female offspring

Gan Hongya,Zhu Bingqi,Zhou Fangmei,Ding Zhishan,Liu Jing,Ye Xiaoqing

Pyrethroid insecticides are ubiquitously detected in environmental media, food, and urine samples. Our previous epidemiological study reported a correlation between increased pyrethroid exposure and delayed pubertal development in Chinese girls. In this study, we further investigated the effects of perinatal exposure to low doses of cypermethrin (CP) on pubertal onset and hypothalamic-pituitary-ovarian axis in the female mice offspring. The treatment of CP with 60 μg/kg/day from gestation day 6 (GD6) to postnatal day 21 (PND21) significantly decreased the time to puberty in the female offspring. Exposure of CP increased the serum levels of gonadotropin-releasing hormone (GnRH) and the expression of GnRH genes in a dose-dependent manner in the female offspring. CP also induced the serum levels of luteinizing hormone (LH) and follicle-stimulating hormone (FSH), as well as the expression of gonadotropin subunit genes [LHβ, FSHβ, and chorionic gonadotropin α (Cgα)]. Furthermore, CP induced serum estradiol (E 2 ) levels and the expression of steroidogenesis-related genes [steroidogenic acute regulatory (StAR) and Cytochrome p 450, family 11, subfamily A, polypeptide 1 (CYP11A1)] in the ovary. In accordance with the in vivo tests, administration of CP (6.7, 20, and 60 μg/L) stimulated a dose-dependent increase in the synthesis and secretion of the puberty-related hormones in the explants of hypothalamus, pituitary, and ovary. The interference with calcium channels in the ovary may be responsible for CP-induced pubertal onset. Our study provided evidence that perinatal exposure to low doses of CP induced puberty-related hormones and decreased the time to puberty in the female offspring.

CAS / MDL: 7786-30-3
研究领域: 环境健康 · 内分泌学 · 生殖生物学 · 毒理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Agriculture-Basel · 2025 ·Vol. 16 ·期 1 ·83 · IF 3.6

Association of VGSC Mutations and P450 Overexpression with Beta-Cypermethrin Resistance in Aphis gossypii Glover from a Chinese Wolfberry (Lycium barbarum L.) Field

Yunfei Zhang,Xinyi Hu,Junjie Yin,Jiabin Chen,Shujing Zhang,Fang Wang

Chinese wolfberry (Lycium barbarumL.), a specialty crop with ecological, medical, and economic value in Ningxia province of China, is subject to severe damage fromAphis gossypiiGlover. Currently,A. gossypiipopulations show extremely high-level resistance to beta-cypermethrin in the major wolfberry planting areas in Ningxia. The specific resistance mechanisms, however, are still not known. In this work, we collected a fieldA. gossypiistrain (HSP) from a wolfberry orchard in Ningxia in 2021 using a single-time sampling method, and its resistance to beta-cypermethrin was determined to be extremely high (994.74-fold) as compared with that of a susceptible strain (SS). Then we explored the potential resistance mechanisms from two aspects, namely, metabolic detoxification and target-site alterations. Bioassays of beta-cypermethrin with or without a synergist showed that piperonyl butoxide (PBO) significantly increased the toxicity of beta-cypermethrin (4.72-fold) to the HSP strain, while triphenyl phosphate (TPP) and diethyl maleate (DEM) exhibited no significant synergistic effects. Correspondingly, theO-demethylase activity of cytochrome P450s in the HSP strain was 1.68-fold higher than that in the susceptive strain (SS), whereas changes in carboxylesterases and glutathioneS-transferases activities were unremarkable. Also, fifteen upregulated P450 genes were identified by both RNA-Seq and qRT-PCR technologies, containing eleven CYP6 genes, three CYP4 genes, and one CYP380 gene. Especially, five CYP6 genes with high relative expression levels (>3.00-fold) were intensively expressed by beta-cypermethrin induction in the HSP aphids. These metabolism-related results indicate the key role of P450-mediated metabolic detoxification in HSP resistance to beta-cypermethrin. Sequencing of voltage-gated sodium channel (VGSC) genes identified a prevalent M918L mutation and a new G1012D mutation in HSPA. gossypii. Moreover, heterozygous 918 M/L and 918 M/L + G1012D mutations were the dominant genotypes with frequencies of 60.00% and 36.67% in the HSP population, respectively. Overall,VGSCmutations along with P450-mediated metabolic resistance contributed to the extremely high resistance of the HSP wolfberry aphids to beta-cypermethrin, providing support forA. gossypiicontrol and resistance management in the wolfberry planting areas of Ningxia using insecticides with different modes of action.

研究领域: 昆虫学 · 杀虫剂抗性 · 分子生物学 · 植物保护 · 毒理学 · 农业科学
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JOURNAL OF HAZARDOUS MATERIALS · 2025 · IF 11.3

Mechanisms of cypermethrin degradation and remediation by Rhodococcus sp. H-3: Insights from comparative genomics, hydrolase CymE1 secretory expression, and bacterial community analysis

Guoqiang Zhao,Wenjing Chen,Rongrong Zhang,Rui Zhang,Bo Jiang,Ruyan Hou,Xing Huang

Cypermethrin, a common pyrethroid insecticide, raises significant ecological concerns due to its widespread use. In this study, a highly efficient cypermethrin-degrading strain, Rhodococcus sp. H-3, was isolated. The strain was capable of degrading 30 mg/L cypermethrin at the rate of 83.48 % within 7 days and it could hydrolyze cypermethrin into 3-phenoxybenzoic acid (3-PBA) and permethric acid (DCVA). A novel cypermethrin degradation gene, cymE1 , was identified in strain H-3 through genome analysis, and its highest level of amino acid sequence similarity observed was 33.50 % in the Swiss-Prot database. The functional strain, SCK6-E, which could secrete CymE1, was successfully constructed by using double-exchange strategies. Strain SCK6-E could be applied for the removal of cypermethrin residues from tea plant leaves with a removal rate of 57.83 % within 2 h. Furthermore, strain H-3 demonstrated the capability to remediate cypermethrin-contaminated soil, exhibiting a degradation rate of 65.80 % over 10 days. The results of the 16S rRNA high-throughput sequencing indicated that strain H-3 was conducive to the restoration of the diversity and richness of the bacterial community in the soil. This study provides novel strain and gene resources for researching the degradation mechanism of pyrethroids, and offers valuable insights for developing effective pesticide residue remediation strategies.

CAS / MDL: 52315-07-8
研究领域: 环境微生物学 · 生物修复 · 基因组学 · 分子生物学 · 农业科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PEST MANAGEMENT SCIENCE · 2019 ·Vol. 75 ·期 7 ·2009-2019 · IF 3.255

Transcription factors CncC/Maf and AhR/ARNT coordinately regulate the expression of multiple GSTs conferring resistance to chlorpyrifos and cypermethrin in Spodoptera exigua

Bo Hu,He Huang,Qi Wei,Miaomiao Ren,David K Mburu,Xiangrui Tian,Jianya Su

BACKGROUND Glutathione S -transferases (GSTs) are a superfamily of multifunctional dimeric proteins existing in both prokaryotic and eukaryotic organisms. They are involved in the detoxification of both endogenous and exogenous electrophiles, including insecticides. However, the molecular mechanisms underlying the regulation of GST genes in insects are poorly understood. RESULTS We first identified at least three GST genes involved in resistance to the insecticides chlorpyrifos and cypermethrin. Analysis of upstream sequences revealed that three GSTs ( SeGSTo2 , SeGSTe6 and SeGSTd3 ) harbor the same cap ‘n’ collar C/muscle aponeurosis fibromatosis (CncC/Maf) binding site, and SeGSTo2 and SeGSTe6 contain the aryl hydrocarbon receptor/aryl hydrocarbon receptor nuclear translocator (AhR/ARNT) binding site. Luciferase reporter assay showed co-transfection of reporter plasmid containing the SeGSTe6 promoter with CncC and/or Maf expressing constructs significantly boosted transcription. Similarly, AhR and/or ARNT expressing constructs also significantly increased the promoter activities. The co-transfection of mutated reporter plasmid with CncC/Maf or AhR/ARNT did not increase transcription activity anymore. Constitutive over-expression of CncC, Maf and AhR was also found in the HZ16 strain, which might be the molecular mechanism for up-regulated expression of multiple detoxification genes conferring resistance to insecticides. CONCLUSION These results suggest that CncC/Maf and AhR/ARNT coordinately regulate the expression of multiple GST genes involved in insecticide resistance in Spodoptera exigua . © 2019 Society of Chemical Industry

研究领域: 昆虫学 · 分子生物学 · 毒理学 · 基因组学
✓ 已验证 DOI PubMed 高影响因子
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ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH · 2021 ·Vol. 28 ·期 34 ·47099-47106 · IF 4.223

Effects of Cd2+ and Pb2+ on enantioselective degradation behavior of α-cypermethrin in soils and their combined effect on activities of soil enzymes

Jiang Wenqi,Yao Guojun,Jing Xu,Liu Xueke,Liu Donghui,Zhou Zhiqiang

Heavy metals may coexist with pesticides in farmland through wastewater irrigation, application of pesticides and chemical fertilizers, or unappropriated waste disposal. Heavy metals are toxic to soil microorganism, which may influence the environmental behavior of pesticides subsequently. In this study, the influence of Cd 2+ and Pb 2+ on the degradation of α-cypermethrin and its metabolites, 3-phenoxphenoxybenzoic acid (3-PBA) and 3-(2’,2’-dichlorovinyl)-2,2-dimethylcyclopropane carboxylic acid (DCCA), were investigated through soil incubation experiment. It was found heavy metals like Cd 2+ and Pb 2+ will inhibit the degradation of α-cypermethrin, especially at high concentrations. Pb 2+ has a stronger inhibitory effect on the degradation of α-cypermethrin than Cd 2+ in the same concentration. With the presence of 10 mg/kg Pb 2+ , the half-life of α-cypermethrin increased from 41.1 to 99.9 days, even the half-life was 129.3 days with 50 mg/kg of Pb 2+ . Besides, heavy metals influenced the chiral selective degradation of α-cypermethrin. The enantiomer fraction was near 0.5 when 10 mg/kg of heavy metals existed. Furthermore, the adverse effects of heavy metals on soil urease, catalase, and sucrase activity were assayed. In tested concentrations (10 and 50 mg kg -1 ), the heavy metals result in strong inhibition of the activity of the enzymes present on soil, jeopardizing the biodegradation by the microbiome and which may inhibit the degradation of α-cypermethrin.

研究领域: 环境科学 · 土壤微生物学
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Journal of Food Safety and Food Quality-Archiv fur Lebensmittelhygiene · 2026 ·Vol. 77 ·期 2 · IF 0.9

Development of a Surface-Enhanced Raman Spectroscopy Based Method using Molecularly Imprinted Polymers for the Detection of Trichlorfon and Cypermethrin in Fruits and Vegetables

Shuai Tang,Hong Chang,Gao-hao Tan,Hai-rong Cen,Qiu-an Mo

Background:Excessive residues of organophosphorus pesticide pose a serious threat to consumer health and negatively impact the export trade of agricultural products in China. Therefore, establishing a rapid, accurate and reliable multiresidue detection method for organophosphorus pesticides to safeguard consumer health is highly necessary.Methods:This study aimed to develop a combined detection method integrating surface-enhanced Raman spectroscopy (SERS) with molecularly imprinted polymer (SERS-MIP) technology. Quantitative analysis of two pesticides, trichlorfon and cypermethrin, as examples, enables rapid detection of pesticide residues in fruits and vegetables. The effects of four fruits and vegetables (oranges, tangerines, leeks, and spinach) on the detection of two pesticide residues were also investigated, with a focus on matrix effects on the SERS-MIP combined technique.Results:The limit of detection (LOD) for trichlorfon in oranges and tangerines was 1.27 μg/kg, with recovery rates ranging from 95.2% to 101.4%. The LOD for cypermethrin in leeks and spinach was 0.13 μg/kg, with recovery rates ranging from 95.2% to 100.3%. For all four matrices, the method enabled rapid quantitative detection with high specificity and sensitivity, meeting current market demands.Conclusions:This approach holds promise for detecting other pesticide residues and provides a useful reference direction for developing rapid pesticide residue testing methods.

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Comparative Biochemistry and Physiology D-Genomics & Proteomics · 2019 · IF 2.573

Identification of glutathione-S-transferase genes by transcriptome analysis in Meteorus pulchricornis (Hymenoptera: Braconidae) and their expression patterns under stress of phoxim and cypermethrin

Xiao-rui Zhang,Jia-qi Zhang,Ying-ying Shao,Xiao-rong Xing,Jiao Wang,Zhi-xiang Liu,Yi-jiangcheng Li,Andrews Danso Ofori,Qing-bo Tu,Jun Wang,Sheng Sheng,Fu-an Wu

Meteorus pulchricornis (Wesmael) (Hymenoptera: Braconidae) is a preponderant endoparasitoid wasp, attacking the larvae of many lepidopteran pests. We present the first body transcriptome dataset for M. pulchricornis . In total, 50,781,796 clean reads were obtained and 33,144 unigenes were assembled; 15,458 unigenes showed a significant similarity (E value < 10 −5 ) to known proteins in the NCBI non-redundant protein database . Gene ontology and cluster of orthologous group analyses were performed to classify the functions of genes. To better understand the role of glutathione-S-transferases (GSTs) in detoxification mechanism in M. pulchricornis , we identified seventeen GST genes ( MpulGSTs ) from the body transcriptome. Among these, fifteen MpulGSTs belonged to cytosolic GSTs and the other two belonged to microsomal classes. The cytosolic GSTs were classified into four different clades: four in delta, three in omega, seven in sigma, and one in zeta. The expression levels of these MpulGSTs after exposure to sub-lethal concentrations of phoxim and cypermethrin were determined using real-time quantitative polymerase chain reaction: seven MpulGSTs ( MpulGSTD3 , MpulGSTS1 , MpulGSTS2 , MpulGSTS4 , MpulGSTS6 MpulGSTO3 , and MpulGSTmic1 ) and 11 MpulGSTs ( MpulGSTD1 , MpulGSTD2 , MpulGSTD3 , MpulGSTO2 , MpulGSTS1 , MpulGSTS2 , MpulGSTS3 , MpulGSTS4 , MpulGSTS5 , MpulGSTS7 , and MpulGSTmic1 ) were highly expressed, respectively. These results suggested that GST genes may play a pivotal role in detoxification process in M. pulchricornis . Our findings would provide a theoretical base for elucidating insecticide susceptibility and should promote functional research on specific GST genes in parasitoid wasps.

研究领域: 昆虫学 · 基因组学 · 毒理学 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF HAZARDOUS MATERIALS · 2021 · IF 10.588

Characterization of a novel beta-cypermethrin-degrading strain of Lactobacillus pentosus 3-27 and its effects on bioremediation and the bacterial community of contaminated alfalfa silage

Fang Liu,Jie Bai,Wenkang Huang,Fuhou Li,Wencan Ke,Yixin Zhang,Dongmei Xie,Bo Zhang,Xusheng Guo

In this study, a novel beta-cypermethrin (beta-cyp)-degrading strain Lactobacillus pentosus 3–27 (LP3–27) was screened from beta-cyp-contaminated silage. The strain could degrade 96% of beta-cyp (50 mg/L) in MSM medium after 4 d of culture, while the strain lost its degradation ability when the beta-cyp concentration reached 250 mg/L. The effects of LP 3–27 on fermentation, bacterial community, and bioremediation of contaminated alfalfa silage at two dry matter (DM) contents were studied. The results showed that inoculation with LP3–27 not only degraded beta-cyp, but also improved the fermentation quality of alfalfa silage after 60 d of ensiling. Meanwhile, L. pentosus dominated the bacterial community during ensiling in LP3–27 inoculated silages, whereas Pediococcus acidilactici was the dominant species in the control silage. LP3–27 inoculation also simplified the bacterial interaction networks of ensiled alfalfa. Beta-cyp degradation was positively correlated with L. pentosus in LP- inoculated silages, which confirmed the function of beta-cyp degradation by L. pentosus . In addition, higher beta-cyp degradation was observed in silage with 35% versus 43% DM. In summary, strain LP3–27 could be used as a candidate inoculum for bioremediation of beta-cyp-contaminated silage and to produce safe silage for animal production.

研究领域: 微生物学 · 环境科学 · 动物营养学
✓ 已验证 DOI PubMed 高影响因子
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