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Bactericidal bissulfone B7 targets bacterial pyruvate kinase to impair bacterial biology and pathogenicity in plants

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science China(Life sciences) 2024年第2期67卷 391-402页

作者： Awei Zhang Haizhen Zhang Ronghua Wang Hongfu He Baoan Song Runjiang Song National Key Laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationCenter for R&D of Fine Chemicals of Guizhou UniversityGuiyang 550025China

The prevention and control of rice bacterial leaf blight(BLB)disease has not yet been achieved due to the lack of effective agrochemicals and available targets.Herein,we develop a series of novel bissulfones and a novel target with a unique mechanism to address this challenge.The developed bissulfones can control Xanthomonas oryzae pv.oryzae(Xoo),and 2-(bis(methylsulfonyl)methylene)-N-(4-chlorophenyl)hydrazine-1-carboxamide(B_(7))is more effective than the commercial drugs thiodiazole copper(TC)and bismerthiazol(BT).Pyruvate kinase(PYK)in Xoo has been identified for the first time as the target protein of our bissulfone B_(7).PYK modulates bacterial virulence via a CRP-like protein(Clp)/two-component system regulatory protein(reg R)axis.The elucidation of this pathway facilitates the use of B_(7)to reduce PYK expression at the transcriptional level,block PYK activity at the protein level,and impair the interaction within the PYK-Clp-reg R complex via competitive inhibition,thereby attenuating bacterial biology and pathogenicity.This study offers insights into the molecular and mechanistic aspects underlying anti-Xoo strategies that target PYK.We believe that these valuable discoveries will be used for bacterial disease control in the future.

关键词： 2-bissulfone-N-phenylhydrazine-1-carboxamide derivatives Xoo antibacterial activities pyruvate kinase regulatory mechanism

Pre-mating nitenpyram exposure in male mice leads to depression-like behavior in offspring by affecting tryptophan metabolism in gut microbiota

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Journal of Environmental sciences 2024年第3期137卷 120-130页

作者： Sen Yan Wei Sun Sinuo Tian Zhiyuan Meng Jinling Diao Zhiqiang Zhou Li Li Wentao Zhu Innovation Center of pesticide Research Department of Applied ChemistryCollege of ScienceChina Agricultural UniversityBeijing 100193China College of Plant Protection/Joint International Research Laboratory of Agriculture&Agri-Product Safety Yangzhou UniversityYangzhou 225009China College of Plant Protection Shanxi Agricultural UniversityTaiyuan 030031China

Several studies have confirmed that the health status of the paternal affects the health of the offspring,however,it remains unknown whether paternal exposure to pesticides affect the offspring health.Here,we used untargeted metabolomics and 16S rRNA sequencing technology,combined with tail suspension test and RT-qPCR to explore the effects of paternal exposure to nitenpyram on the neurotoxicity of offspring.Our results found that the paternal exposure to nitenpyram led to the offspring’s depressive-like behaviors,accompanied by the reduction of tryptophan content and the disorder of microbial abundance in the gut of the offspring.Further,we determined the expression of tryptophan metabolism-related genes tryptophanase(tnaA)and tryptophan hydroxylase 1(TpH1)in gut bacteria and colonic tissues.We found that tryptophan is metabolized to indoles rather than being absorbed into colonocytes,which coursed the reduce of tryptophan availability after nitenpyram exposure.In conclusion,our study deepens our understanding of the intergenerational toxic effects of pesticides.

关键词： Nitenpyram Depressive-like behaviors Gut microbiota Tryptophan metabolism

Discovery and structure-activity relationship studies of novel tetrahydro-β-carboline derivatives as apoptosis initiators for treating bacterial infections

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Journal of Integrative Agriculture 2024年第4期23卷 1259-1273页

作者： Shanshan Su Hongwu Liu Junrong Zhang Puying Qi Yue Ding Ling Zhang Linli Yang Liwei Liu Xiang Zhou Song Yang National Key Laboratory of Green pesticide/Key Laboratory of Green pesticide and Agricultural Bioengineering Ministry of Education/Center for R&D of Fine ChemicalsGuizhou UniversityGuiyang 550025China

Developing and excavating new agrochemicals with highly active and safe is an important tactic for protecting crop health and food safety.In this paper,to discover the new bactericide candidates,we designed,prepared a new type of1,2,3,4-tetrahydro-β-carboline(THC)derivatives and evaluated the in vitro and in vivo bioactivities against the Xanthomonas oryzae pv.oryzae(Xoo),Xanthomonas axonopodis pv.citri(Xac),and Pseudomonas syringae pv.actinidiae(Psa).The in vitro bioassay results exhibited that most title molecules possessed good activity toward the three plant pathogenic bacteria,the compound A17 showed the most active against Xoo and Xac with EC50 values of 7.27 and 4.89 mg mL^(-1)respectively,and compound A8 exhibited the best inhibitory activity against Psa with EC50value of 4.87 mg mL^(-1).Pot experiments showed that compound A17 exhibited excellent in vivo antibacterial activities to manage rice bacterial leaf blight and citrus bacterial canker,with protective efficiencies of 52.67 and 79.79%at 200 mgmL^(-1),respectively.Meanwhile,compound A8 showed good control efficiency(84.31%)against kiwifruit bacterial canker at 200 mg mL^(-1).Antibacterial mechanism suggested that these compounds could interfere with the balance of the redox system,damage the cell membrane,and induce the apoptosis of Xoo cells.Taken together,our study revealed that tetrahydro-β-carboline derivatives could be a promising candidate model for novel broadspectrum bactericides.

关键词： tetrahydro-β-carboline derivatives antibacterial activity ROS cell apoptosis

Phytochemical analysis, antioxidant, acetylcholinesterase, and α-amylase inhibitors from Hippeastrum hybridum extract

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Journal of Traditional Chinese Medicine 2024年第3期44卷 496-504页

作者： Naila Sher Mushtaq Ahmed Nadia Mushtaq department of Biotechnology University of Science and Technology department of Botany University of Science and Technology

OBJECTIVE:To investigate the effects of Hippeastrum hybridum（HH） as a free radical scavenger,and an inhibitor of the two enzymes i-e Alpha-amylase（α-amylase） and acetylcholinesterase（AChE）.METHODS:In this study,HH plant was preliminary analyzed for phytochemical screening and then tested for its antioxidant,anti-α-amylase,and anti-AChE efficiency via standard procedures.RESULTS:Phytochemical analysis shows the existence of different compounds;while Coumarins and quinones were absent.The total phenolic,flavonoid,and tannins content were found to be（78.52±0.69） mg GAE/g,（2.01±0.04） mg RUE/g,and（58.12±0.23） mg TAE/g of plant extract respectively.28.02%±0.02% alkaloid and 2.02%±0.05% saponins were present in the HH extract.The HH extract showed the anti-oxidant property with IC50（50%inhibition） of（151.01±0.13）(HH),（79.01±0.04）(Ascorbic acid) for ferric reducing,（91.48±0.13）(HH),（48.02±0.11）(Ascorbic acid) against Ammonium molybdenum,（156.02±0.31）(HH),（52.38±0.21）(Ascorbic acid) against DPPH,136.01±0.21（HH）,52.02±0.31（Ascorbic acid） against H2O2,and 154.12±0.03（HH）,（40.05±0.15）(Ascorbic acid)μg/mL against ABTS respectively.Statistical analysis indicated that HH caused a competitive type of inhibition of α-amylase(Vmaxremained constant and Km increases from 10.65 to84.37%) while Glucophage caused the un-competitive type of inhibition i-e both Km and Vmaxdecreased from40.49 to 69.15%and 38.86 to 69.61%respectively.The Ki,（inhibition constant）;KI,（dissociation constant）,Km,（Michaelis-Menten constant）,and IC50 were found to be62,364,68.1,and 38.08±0.22 for HH and 12,101.05,195,34.01±0.21 for Glucophage.Similarly,HH causes an anon-competitive type of inhibition of AChE i-e Km remains constant while Vmaxdecreases from 60.5%to74.1%.The calculated Ki,KI,Km,and IC50 were found to be 32,36.2,0.05,and 18.117±0.018.CONCLUSION:From the current results,it is concluded that HH extract contains bioactive compounds,and could be a good alternative to controlling oxidants,Alzheimer‘s and Type-Ⅱ diabetic diseases.

关键词： Hippeastrum hybridum acetylcholinesterase alpha-amylase antioxidant phytochemicals

Orthogonal Combinatorial Raman Codes Enable Rapid High-Throughput-Out Library Screening of Cell-Targeting Ligands

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Research 2024年第1期2023卷 199-208页

作者： Yuchen Tang Xingxing Zheng Tingjuan Gao China Key Laboratory of pesticide and Chemical Biology of Ministry of Education College of ChemistryCentral China Normal UniversityWuhan 430079China

High-throughput assays play an important role in the fields of drug discovery,genetic analysis,and clinical diagnostics.Although super-capacity coding strategies may facilitate labeling and detecting large numbers of targets in a single assay,practically,the constructed large-capacity codes have to be decoded with complicated procedures or are lack of survivability under the required reaction conditions.This challenge results in either inaccurate or insufficient decoding outputs.Here,we identified chemical-resistant Raman compounds to build a combinatorial coding system for the high-throughput screening of cell-targeting ligands from a focused 8-mer cyclic peptide library.The accurate in situ decoding results proved the signal,synthetic,and functional orthogonality for this Raman coding strategy.The orthogonal Raman codes allowed for a rapid identification of 63 positive hits at one time,evidencing a high-throughput-out capability in the screening process.We anticipate this orthogonal Raman coding strategy being generalized to enable efficient high-throughput-out screening of more useful ligands for cell targeting and drug discovery.

关键词： enable throughput allowed

Lighting up plants with near-infrared fluorescence probes

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science China Chemistry 2024年第3期67卷 774-787页

作者： Yida Pang Mengjiao Lu Hyeonji Rha Wenchao Yang Amit Sharma Yao Sun Jong Seung Kim National Key Laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationCenter for R&D of Fine Chemicals of Guizhou UniversityGuiyang 550025China National Key Laboratory of Green pesticide College of ChemistryCentral China Normal UniversityWuhan 430079China department of Chemistry Korea UniversitySeoul 02841Korea CSIR-Central Scientific Instruments Organisation Sector-30CChandigarh160030India TheranoChem Incorporation Seongbuk-guSeoul02856Korea

Fluorescence imaging is a non-invasive and highly sensitive bioimaging technique that has shown remarkable strides in plant science. It enables real-time monitoring and analysis of biological and pathological processes in plants by labeling specific molecular or cellular structures with fluorescent probes. However, tissue scattering and phytochrome interference have been obstacles for conventional fluorescence imaging of plants in the ultraviolet and visible spectrum, resulting in unsatisfactory imaging quality. Fortunately, advances in near-infrared(NIR) fluorescence imaging technology(650-900 nm) offer superior spatial-temporal resolution and reduced tissue scattering, which is sure to improve plant imaging quality. In this review, we summarize recent progress in the development of NIR fluorescence imaging probes and their applications for in vivo plant imaging and the identification of plant-related biomolecules. We hope this review provides a new perspective for plant science research and highlights NIR fluorescence imaging as a powerful tool for analyzing plant physiology, adaptive mechanisms, and coping with environmental stress in the near future.

关键词： NIR fluorescent probe plant imaging biologic application

Carbene-catalyzed enantioselective seleno-Michael addition as access to antimicrobial active Se-containing heterocycles

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science China Chemistry 2024年第7期67卷 2199-2205页

作者： Hongyan Long Sha Zhao Chunyan Jian Xiuli Wu Fengfei Lu Minghong Liao Fengrui Che Xingxing Wu Yonggui Robin Chi State Key Laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore

Organoseleniums exhibit a diverse set of biological activities that are pivotal for drug discovery and are widely explored in synthetic chemistry and material science.While many transformations have been developed for non-enantioselective C–Se bond formations,the catalyst-controlled stereoselective preparation of chiral organoseleniums continues to be of considerable challenge.In particular,there are limited studies on the enantioselective seleno-Michael addition reactions to access chiral selenium functional molecules.Here,we disclose a carbene-catalyzed highly enantioselective nucleophilic C–Se bond construction through formal[3+3]annulations between selenocarboxamides and bromoenals,affording seleno-thiazinone products with good yields and excellent enantioselectivities.The choice of a weak inorganic base was pivotal to suppressing the unproductive racemization and decomposition of the selenium products.Notably,the catalytically generated chiral selenium-containing heterocyclic products feature remarkable antimicrobial activities that could serve as promising lead scaffolds for further agrochemical development.

关键词： seleno-Michael addition organocatalysis N-heterocyclic carbene seleno-heterocycles antimicrobial activity

Complexed amino acid minerals vs. bis-glycinate chelated minerals:Impact on the performance of old laying hens

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Animal Nutrition 2024年第1期16卷 395-408页

作者： Marcos J.B.Santos Maria C.M.M.Ludke Leandro M.Silva Carlos B.V.Rabello Mércia R.Barros Fabiano S.Costa Clariana S.Santos Jamille S.S.Wanderley department of Animal science Rural Federal University of Pernambuco department of Veterinary science Rural Federal University of Pernambuco

The present study was to evaluate the effect of trace minerals(Zn, Mn, and Cu) from complexed amino acid minerals(ZMCAA) and bis-glycinate chelated minerals(ZMCGly) in laying hen diets on performance,internal and external egg quality, yolk mineral deposition, intestinal morphometry, and bone characteristics. From 78 to 98 weeks of age, 400 White LSL-Lite strain laying hens were distributed in a randomized design with 4 treatments with 10 replicates per treatment. Treatments were distributed in a 2 ×2 factorial arrangement using either Zn, Mn, and Cu of ZMCAA or ZMCGly source at 2 levels: low(20, 20,and 3.5 mg/kg of Zn, Mn, and Cu, respectively) or high(40, 40, and 7 mg/kg of Zn, Mn, and Cu,respectively). The analysis of variance was performed, and in cases where differences were observed, the means were compared using Tukey?s test(P < 0.05). The source and level of trace mineral supplementation had a significant impact on the performance of laying hens. Hens fed ZMCAA had higher egg production(P = 0.01), egg weight(P = 0.02), egg mass(P = 0.01), and lower feed conversion ratio(P =0.05) compared to those fed ZMCGly. The ZMCAA supplementation showed higher albumen height(P =0.01), albumen weight(P = 0.01), and eggshell thickness(P < 0.01). The deposition of Zn(P < 0.01), Mn(P< 0.01), and Cu(P < 0.01) in the egg yolk was greater for hens received ZMCAA. Tibia weight(P = 0.04)and bone densitometry(P < 0.01) in the tibia were higher with ZMCAA supplementation. In the small intestine, ZMCAA resulted in longer villi(P = 0.02) and shorter crypt depth(P = 0.01) in the duodenum.Jejunum and ileum measurements were influenced by the level and source of trace minerals(P < 0.05).Laying hens fed ZMCAA exhibited superior performance, egg quality, deposition of trace minerals in the egg yolk, and bone density compared to hens fed ZMCGly. In this study, older laying hens supplemented with ZMCAA at lower levels demonstrated adequate levels of supplementation.

关键词： Bis-glycinates Metal-amino acids Radiodensity Trace minerals

Sequential enantioselective Ugi-4CR/post-Ugi transformation strategy:a precise construction of structurally diverse azaspiro polycyclic scaffolds

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science China Chemistry 2024年第2期67卷 576-586页

作者： Xiao-Bao Wu Jun-Xiu Shi Yi-Ming Ou Hua-Jie Jiang Yi-Jun Fang Qi-Ming Wang Quan Gao Jie Yu department of Applied Chemistry Anhui Province Engineering Laboratory for Green Pesticide Development and ApplicationAnhui Province Key Laboratory of Crop Integrated Pest ManagementAnhui Agricultural UniversityHefei230036China

A privileged strategy has been developed for the precise construction of enantioenriched azaspiro polycyclic scaffolds.Structurally diverse azaspiro polycycles bearing multiple contiguous stereocenters are obtained with excellent results(up to 99:1 e.r.,>95:5 d.r.) via sequential enantioselective four-component Ugi reactions/post-Ugi transformations with substrates containing prerequisite functional groups in the presence of anionic stereogenic-at-cobalt(Ⅲ) complexes.

关键词： asymmetric catalysis post-Ugi transformation anionic stereogenic-at-cobalt(Ⅲ)complex azaspiro polycyclic scaffold one-pot synthesis