Pub Date : 2024-07-01DOI: 10.1021/acs.jafc.4c02848
Haolin Yuan, Hongwei Yang, Yang Gao, Jin Zhang, Jinzhou Ren, Xiaoyu Liu, Yixiao Li, Zhengming Li, Bin Zhao, Zhijin Fan
Corn ear rot and fumonisin caused by Fusarium verticillioides pose a serious threat to food security. To find more highly active fungicidal and antitoxic candidates with structure diversity based on naturally occurring lead xanthatin, a series of novel spiropiperidinyl-α-methylene-γ-butyrolactones were rationally designed and synthesized. The in vitro bioassay results indicated that compound 7c showed broad-spectrum in vitro activity with EC50 values falling from 3.51 to 24.10 μg/mL against Rhizoctonia solani and Alternaria solani, which was more active than the positive controls xanthatin and oxathiapiprolin. In addition, compound 7c also showed good antitoxic efficacy against fumonisin with a 48% inhibition rate even at a concentration of 20 μg/mL. Fluorescence quenching and the molecular docking validated both 7c and oxathiapiprolin targeting at FvoshC. RNA sequencing analysis discovered that FUM gene cluster and protein processing in endoplasmic reticulum were downregulated. Our studies have discovered spiropiperidinyl-α-methylene-γ-butyrolactone as a novel FvoshC target-based scaffold for fungicide lead with antitoxin activity.
{"title":"Discovery of Novel Spiropiperidinyl-α-methylene-γ-butyrolactones as Antifungal and Antitoxin Agents Targeting Oxysterol Binding Protein.","authors":"Haolin Yuan, Hongwei Yang, Yang Gao, Jin Zhang, Jinzhou Ren, Xiaoyu Liu, Yixiao Li, Zhengming Li, Bin Zhao, Zhijin Fan","doi":"10.1021/acs.jafc.4c02848","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c02848","url":null,"abstract":"<p><p>Corn ear rot and fumonisin caused by <i>Fusarium verticillioides</i> pose a serious threat to food security. To find more highly active fungicidal and antitoxic candidates with structure diversity based on naturally occurring lead xanthatin, a series of novel spiropiperidinyl-α-methylene-γ-butyrolactones were rationally designed and synthesized. The <i>in vitro</i> bioassay results indicated that compound <b>7c</b> showed broad-spectrum <i>in vitro</i> activity with EC<sub>50</sub> values falling from 3.51 to 24.10 μg/mL against <i>Rhizoctonia solani</i> and <i>Alternaria solani</i>, which was more active than the positive controls xanthatin and oxathiapiprolin. In addition, compound <b>7c</b> also showed good antitoxic efficacy against fumonisin with a 48% inhibition rate even at a concentration of 20 μg/mL. Fluorescence quenching and the molecular docking validated both <b>7c</b> and oxathiapiprolin targeting at FvoshC. RNA sequencing analysis discovered that FUM gene cluster and protein processing in endoplasmic reticulum were downregulated. Our studies have discovered spiropiperidinyl-α-methylene-γ-butyrolactone as a novel FvoshC target-based scaffold for fungicide lead with antitoxin activity.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464269","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-07-01DOI: 10.1021/acs.jafc.4c00815
Margriet Roelse, Nadejda Krasteva, Steve Pawlizak, Michaela K Mai, Maarten A Jongsma
A microfluidic tongue-on-a-chip platform has been evaluated relative to the known sensory properties of various sweeteners. Analogous metrics of typical sensory features reported by human panels such as sweet taste thresholds, onset, and lingering, as well as bitter off-flavor and blocking interactions were deduced from the taste receptor activation curves and then compared. To this end, a flow cell containing a receptor cell array bearing the sweet and six bitter taste receptors was transiently exposed to pure and mixed sweetener samples. The sample concentration gradient across time was separately characterized by the injection of fluorescein dye. Subsequently, cellular calcium responses to different doses of advantame, aspartame, saccharine, and sucrose were overlaid with the concentration gradient. Parameters describing the response kinetics compared to the gradient were quantified. Advantame at 15 μM recorded a significantly faster sweetness onset of 5 ± 2 s and a longer lingering time of 39 s relative to sucrose at 100 mM with an onset of 13 ± 2 s and a lingering time of 6 s. Saccharine was shown to activate the bitter receptors TAS2R8, TAS2R31, and TAS2R43, confirming its known off-flavor, whereas addition of cyclamate reduced or blocked this saccharine bitter response. The potential of using this tongue-on-a-chip to bridge the gap with in vitro assays and taste panels is discussed.
{"title":"Tongue-on-a-Chip: Parallel Recording of Sweet and Bitter Receptor Responses to Sequential Injections of Pure and Mixed Sweeteners.","authors":"Margriet Roelse, Nadejda Krasteva, Steve Pawlizak, Michaela K Mai, Maarten A Jongsma","doi":"10.1021/acs.jafc.4c00815","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c00815","url":null,"abstract":"<p><p>A microfluidic tongue-on-a-chip platform has been evaluated relative to the known sensory properties of various sweeteners. Analogous metrics of typical sensory features reported by human panels such as sweet taste thresholds, onset, and lingering, as well as bitter off-flavor and blocking interactions were deduced from the taste receptor activation curves and then compared. To this end, a flow cell containing a receptor cell array bearing the sweet and six bitter taste receptors was transiently exposed to pure and mixed sweetener samples. The sample concentration gradient across time was separately characterized by the injection of fluorescein dye. Subsequently, cellular calcium responses to different doses of advantame, aspartame, saccharine, and sucrose were overlaid with the concentration gradient. Parameters describing the response kinetics compared to the gradient were quantified. Advantame at 15 μM recorded a significantly faster sweetness onset of 5 ± 2 s and a longer lingering time of 39 s relative to sucrose at 100 mM with an onset of 13 ± 2 s and a lingering time of 6 s. Saccharine was shown to activate the bitter receptors TAS2R8, TAS2R31, and TAS2R43, confirming its known off-flavor, whereas addition of cyclamate reduced or blocked this saccharine bitter response. The potential of using this tongue-on-a-chip to bridge the gap with in vitro assays and taste panels is discussed.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141475400","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-07-01DOI: 10.1021/acs.jafc.4c03388
Yutong Xia, Jia Zhao, Muhammad Saeed, Nazar Hussain, Xihua Chen, Zhongjian Guo, Yangchun Yong, Huayou Chen
Some feed source plants will produce secondary metabolites such as cyanogenic glycosides during metabolism, which will produce some poisonous nitrile compounds after hydrolysis and remain in plant tissues. The consumption of feed-source plants without proper treatment affect the health of the animals' bodies. Nitrilases can convert nitriles and have been used in industry as green biocatalysts. However, due to their bottleneck problems, their application in agriculture is still facing challenges. Acid-resistant nitrilase preparations, high-temperature resistance, antiprotease activity, strong activity, and strict reaction specificity urgently need to be developed. In this paper, the application potential of nitrilase in agriculture, especially in feed processing industry was explored, the source properties and catalytic mechanism of nitrilase were reviewed, and modification strategies for nitrilase application in agriculture were proposed to provide references for future research and application of nitrilase in agricultural and especially in the biological feed scene.
{"title":"Molecular Modification Strategies of Nitrilase for Its Potential Application in Agriculture.","authors":"Yutong Xia, Jia Zhao, Muhammad Saeed, Nazar Hussain, Xihua Chen, Zhongjian Guo, Yangchun Yong, Huayou Chen","doi":"10.1021/acs.jafc.4c03388","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c03388","url":null,"abstract":"<p><p>Some feed source plants will produce secondary metabolites such as cyanogenic glycosides during metabolism, which will produce some poisonous nitrile compounds after hydrolysis and remain in plant tissues. The consumption of feed-source plants without proper treatment affect the health of the animals' bodies. Nitrilases can convert nitriles and have been used in industry as green biocatalysts. However, due to their bottleneck problems, their application in agriculture is still facing challenges. Acid-resistant nitrilase preparations, high-temperature resistance, antiprotease activity, strong activity, and strict reaction specificity urgently need to be developed. In this paper, the application potential of nitrilase in agriculture, especially in feed processing industry was explored, the source properties and catalytic mechanism of nitrilase were reviewed, and modification strategies for nitrilase application in agriculture were proposed to provide references for future research and application of nitrilase in agricultural and especially in the biological feed scene.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464270","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-07-01DOI: 10.1021/acs.jafc.4c01690
Ziyu Wang, Wei Jiang, Rong Tang, Hongxiang Liu, Hao Qian, Tao Guo, Jianjun Zhu, Wenjun Wu, Weiqing Xie, Jiwen Zhang
To synthesize the fundamental framework of dihydroagarofuran, a novel strategy was devised for constructing the C-ring through a dearomatization reaction using 6-methoxy-1-tetralone as the initial substrate. Subsequently, the dihydroagarofuran skeleton was assembled via two consecutive Michael addition reactions. The conjugated diene and trans-dihydroagarofuran skeleton were modified. The insecticidal activities of 33 compounds against Mythimna separata were evaluated. Compounds 11-5 exhibited an LC50 value of 0.378 mg/mL. The activity exhibited a remarkable 29-fold increase compared to positive control Celangulin V, which was widely recognized as the most renowned natural dihydroagarofuran polyol ester insecticidal active compound. Docking experiments between synthetic compounds and target proteins revealed the shared binding sites with Celangulin V. Structure-activity relationship studies indicated that methyl groups at positions C4 and C10 significantly improved insecticidal activity, while ether groups with linear chains displayed enhanced activity; in particular, the allyl ether group demonstrated optimal efficacy. Furthermore, a three-dimensional quantitative structure-activity relationship model was established to investigate the correlation between the skeletal structure and activity. These research findings provide valuable insights for discovering and developing dihydroagarofuran-like compounds.
{"title":"Synthetic Modification and Insecticidal Activity of 4-<i>epi</i>-cis-Dihydroagarofuran Derivatives.","authors":"Ziyu Wang, Wei Jiang, Rong Tang, Hongxiang Liu, Hao Qian, Tao Guo, Jianjun Zhu, Wenjun Wu, Weiqing Xie, Jiwen Zhang","doi":"10.1021/acs.jafc.4c01690","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c01690","url":null,"abstract":"<p><p>To synthesize the fundamental framework of dihydroagarofuran, a novel strategy was devised for constructing the C-ring through a dearomatization reaction using 6-methoxy-1-tetralone as the initial substrate. Subsequently, the dihydroagarofuran skeleton was assembled via two consecutive Michael addition reactions. The conjugated diene and trans-dihydroagarofuran skeleton were modified. The insecticidal activities of 33 compounds against <i>Mythimna separata</i> were evaluated. Compounds <b>11</b>-<b>5</b> exhibited an LC<sub>50</sub> value of 0.378 mg/mL. The activity exhibited a remarkable 29-fold increase compared to positive control Celangulin V, which was widely recognized as the most renowned natural dihydroagarofuran polyol ester insecticidal active compound. Docking experiments between synthetic compounds and target proteins revealed the shared binding sites with Celangulin V. Structure-activity relationship studies indicated that methyl groups at positions C4 and C10 significantly improved insecticidal activity, while ether groups with linear chains displayed enhanced activity; in particular, the allyl ether group demonstrated optimal efficacy. Furthermore, a three-dimensional quantitative structure-activity relationship model was established to investigate the correlation between the skeletal structure and activity. These research findings provide valuable insights for discovering and developing dihydroagarofuran-like compounds.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141475399","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-06-30DOI: 10.1021/acs.jafc.4c00864
Cindy Weng, Cade Napier, Cedric Katte, Spencer S. Walse, William A. Mitch
The post-harvest fumigant, sulfuryl fluoride (SO2F2), is a >1000-fold more potent greenhouse gas than carbon dioxide and methane. Pilot studies have shown that SO2F2 fumes vented from fumigation chambers can be captured and hydrolyzed by hydroxide (OH–) and hydrogen peroxide (H2O2) at pH ∼ 12 in a scrubber, producing SO42– and F– as waste salts. To reduce the costs and challenges associated with purchasing and mixing these reagents onsite, this study evaluates the electrochemical generation of OH– and H2O2 within spent scrubbing solution, taking advantage of the waste SO42– and F– as free sources of electrolyte. The study used a gas diffusion electrode constructed from carbon paper coated with carbon black as a catalyst selective for the reduction of O2 to H2O2. Under galvanostatic conditions, the study evaluated the effect of electrochemical conditions, including applied cathodic current density and electrolyte strength. Within an electrolyte containing 200 mM SO42– and 400 mM F–, comparable to the waste salts generated by a SO2F2 scrubbing event, the system produced 250 mM H2O2 at pH 12.6 within 4 h with a Faradaic efficiency of 98.8% for O2 reduction to H2O2. In a scrubbing-water sample from lab-scale fumigation, the system generated ∼200 mM H2O2 at pH 13.5 within 4 h with a Faradaic efficiency of 75.6%. A comparison of the costs to purchase NaOH and H2O2 against the electricity costs for electrochemical treatment indicated that the electrochemical approach could be 38–71% lower, depending on the local cost of electricity.
{"title":"Electrochemical Generation of Hydroxide and Hydrogen Peroxide for Hydrolysis of Sulfuryl Fluoride Fumigant","authors":"Cindy Weng, Cade Napier, Cedric Katte, Spencer S. Walse, William A. Mitch","doi":"10.1021/acs.jafc.4c00864","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c00864","url":null,"abstract":"The post-harvest fumigant, sulfuryl fluoride (SO<sub>2</sub>F<sub>2</sub>), is a >1000-fold more potent greenhouse gas than carbon dioxide and methane. Pilot studies have shown that SO<sub>2</sub>F<sub>2</sub> fumes vented from fumigation chambers can be captured and hydrolyzed by hydroxide (OH<sup>–</sup>) and hydrogen peroxide (H<sub>2</sub>O<sub>2</sub>) at pH ∼ 12 in a scrubber, producing SO<sub>4</sub><sup>2–</sup> and F<sup>–</sup> as waste salts. To reduce the costs and challenges associated with purchasing and mixing these reagents onsite, this study evaluates the electrochemical generation of OH<sup>–</sup> and H<sub>2</sub>O<sub>2</sub> within spent scrubbing solution, taking advantage of the waste SO<sub>4</sub><sup>2–</sup> and F<sup>–</sup> as free sources of electrolyte. The study used a gas diffusion electrode constructed from carbon paper coated with carbon black as a catalyst selective for the reduction of O<sub>2</sub> to H<sub>2</sub>O<sub>2</sub>. Under galvanostatic conditions, the study evaluated the effect of electrochemical conditions, including applied cathodic current density and electrolyte strength. Within an electrolyte containing 200 mM SO<sub>4</sub><sup>2–</sup> and 400 mM F<sup>–</sup>, comparable to the waste salts generated by a SO<sub>2</sub>F<sub>2</sub> scrubbing event, the system produced 250 mM H<sub>2</sub>O<sub>2</sub> at pH 12.6 within 4 h with a Faradaic efficiency of 98.8% for O<sub>2</sub> reduction to H<sub>2</sub>O<sub>2</sub>. In a scrubbing-water sample from lab-scale fumigation, the system generated ∼200 mM H<sub>2</sub>O<sub>2</sub> at pH 13.5 within 4 h with a Faradaic efficiency of 75.6%. A comparison of the costs to purchase NaOH and H<sub>2</sub>O<sub>2</sub> against the electricity costs for electrochemical treatment indicated that the electrochemical approach could be 38–71% lower, depending on the local cost of electricity.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":6.1,"publicationDate":"2024-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141463992","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-06-29DOI: 10.1021/acs.jafc.4c03546
Dong Hao Wang, Lerong Qi, Tingxiang Yang, Chuanshun Dai, J. Thomas Brenna, Zhen Wang
Omega-3 long-chain polyunsaturated fatty acids (LCPUFA) play critical roles in human development and health. Their intake is often effectively estimated solely based on seafood consumption, though the high intake of terrestrial animal-based foods with minor amounts of LCPUFA may be significant. Covalent adduct chemical ionization (CACI) tandem mass spectrometry is one approach for de novo structural and quantitative analysis of minor unsaturated fatty acids (FA), for which standards are unavailable. Here, CACI-MS and MS/MS are used to identify and quantify minor omega-3 LCPUFA of terrestrial animal foods based on the application of measured response factors (RFs) to various FA. American mean intakes of pork, beef, chicken, and eggs contribute 20, 27, 45, and 71 mg/day of docosahexaenoic acid (DHA), respectively. The estimated intake of omega-3 DHA, eicosapentaenoic acid, and docosapentaenoic acid from nonseafood sources is significant, at 164, 103, and 330 mg/day, greater than most existing estimates of omega-3 LCPUFA intake.
{"title":"Omega-3 Long-Chain Polyunsaturated Fatty Acids in Nonseafood and Estimated Intake in the USA: Quantitative Analysis by Covalent Adduct Chemical Ionization Mass Spectrometry","authors":"Dong Hao Wang, Lerong Qi, Tingxiang Yang, Chuanshun Dai, J. Thomas Brenna, Zhen Wang","doi":"10.1021/acs.jafc.4c03546","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c03546","url":null,"abstract":"Omega-3 long-chain polyunsaturated fatty acids (LCPUFA) play critical roles in human development and health. Their intake is often effectively estimated solely based on seafood consumption, though the high intake of terrestrial animal-based foods with minor amounts of LCPUFA may be significant. Covalent adduct chemical ionization (CACI) tandem mass spectrometry is one approach for <i>de novo</i> structural and quantitative analysis of minor unsaturated fatty acids (FA), for which standards are unavailable. Here, CACI-MS and MS/MS are used to identify and quantify minor omega-3 LCPUFA of terrestrial animal foods based on the application of measured response factors (RFs) to various FA. American mean intakes of pork, beef, chicken, and eggs contribute 20, 27, 45, and 71 mg/day of docosahexaenoic acid (DHA), respectively. The estimated intake of omega-3 DHA, eicosapentaenoic acid, and docosapentaenoic acid from nonseafood sources is significant, at 164, 103, and 330 mg/day, greater than most existing estimates of omega-3 LCPUFA intake.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":6.1,"publicationDate":"2024-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464023","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-06-29DOI: 10.1021/acs.jafc.4c03936
Lei Li, Tingting Ran, Hong Zhu, Mengyu Yin, Wei Yu, Jingpei Zou, Linwei Li, Yonghao Ye, Hao Sun, Weiwu Wang, Jingjing Guo, Feng Zhang
Fusarium head blight caused by Fusarium graminearum is a devastating disease in wheat that seriously endangers food security and human health. Previous studies have found that the secondary metabolite phenazine-1-carboxamide produced by biocontrol bacteria inhibited F. graminearum by binding to and inhibiting the activity of histone acetyltransferase Gcn5 (FgGcn5). However, the detailed mechanism of this inhibition remains unknown. Our structural and biochemical studies revealed that phenazine-1-carboxamide (PCN) binds to the histone acetyltransferase (HAT) domain of FgGcn5 at its cosubstrate acetyl-CoA binding site, thus competitively inhibiting the histone acetylation function of the enzyme. Alanine substitution of the residues in the binding site shared by PCN and acetyl-CoA not only decreased the histone acetylation level of the enzyme but also dramatically impacted the development, mycotoxin synthesis, and virulence of the strain. Taken together, our study elucidated a competitive inhibition mechanism of Fusarium fungus by PCN and provided a structural template for designing more potent phenazine-based fungicides.
{"title":"Molecular Mechanism of Fusarium Fungus Inhibition by Phenazine-1-carboxamide","authors":"Lei Li, Tingting Ran, Hong Zhu, Mengyu Yin, Wei Yu, Jingpei Zou, Linwei Li, Yonghao Ye, Hao Sun, Weiwu Wang, Jingjing Guo, Feng Zhang","doi":"10.1021/acs.jafc.4c03936","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c03936","url":null,"abstract":"Fusarium head blight caused by <i>Fusarium graminearum</i> is a devastating disease in wheat that seriously endangers food security and human health. Previous studies have found that the secondary metabolite phenazine-1-carboxamide produced by biocontrol bacteria inhibited <i>F. graminearum</i> by binding to and inhibiting the activity of histone acetyltransferase Gcn5 (FgGcn5). However, the detailed mechanism of this inhibition remains unknown. Our structural and biochemical studies revealed that phenazine-1-carboxamide (PCN) binds to the histone acetyltransferase (HAT) domain of FgGcn5 at its cosubstrate acetyl-CoA binding site, thus competitively inhibiting the histone acetylation function of the enzyme. Alanine substitution of the residues in the binding site shared by PCN and acetyl-CoA not only decreased the histone acetylation level of the enzyme but also dramatically impacted the development, mycotoxin synthesis, and virulence of the strain. Taken together, our study elucidated a competitive inhibition mechanism of Fusarium fungus by PCN and provided a structural template for designing more potent phenazine-based fungicides.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":6.1,"publicationDate":"2024-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141463989","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-06-29DOI: 10.1021/acs.jafc.4c02841
Dongdong Liu, Jialin Ye, Yixing Gao, Hongyan Pei, Chunfeng Luo, Huan Tian, Juan He, Jing Zhang, Lixin Zhang
Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds A12–A17 with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC50 values for compounds A12–A17 against Tetranychus cinnabarinus ranged from 0.58 to 0.91 mg/L. Compound A15 showed an LC50 value of 0.29 and 3.10 mg/L against Plutella xylostella and Myzus persicae, respectively. Molecular docking indicated the potential binding interactions of compound A15 with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.
{"title":"Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety","authors":"Dongdong Liu, Jialin Ye, Yixing Gao, Hongyan Pei, Chunfeng Luo, Huan Tian, Juan He, Jing Zhang, Lixin Zhang","doi":"10.1021/acs.jafc.4c02841","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c02841","url":null,"abstract":"Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds <b>A12</b>–<b>A17</b> with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC<sub>50</sub> values for compounds <b>A12</b>–<b>A17</b> against <i>Tetranychus cinnabarinus</i> ranged from 0.58 to 0.91 mg/L. Compound <b>A15</b> showed an LC<sub>50</sub> value of 0.29 and 3.10 mg/L against <i>Plutella xylostella</i> and <i>Myzus persicae</i>, respectively. Molecular docking indicated the potential binding interactions of compound <b>A15</b> with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":6.1,"publicationDate":"2024-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141463997","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-06-29DOI: 10.1021/acs.jafc.4c01487
Li-Xue Qiu, Dong-Xing Guan, Yi-Wen Liu, H. Henry Teng, Zi-Bo Li, Alexander Lux, Yakov Kuzyakov, Lena Q. Ma
Arbuscular mycorrhizal fungi (AMF) influence silicon (Si) uptake by plants, but the mechanisms remain unclear. This study investigated the mechanisms of AMF-mediated Si uptake by rice, a model Si-accumulating plant, and explored the tripartite interactions among AMF, Si, and phosphorus (P). AMF inoculation increased shoot Si content by 97% when supplied with silicic acid and by 29% with calcium silicate and upregulated expression of Si transporters Lsi1 and Lsi2 in roots. Supplying Si only to AMF hyphae increased the root Si content by 113%, indicating direct Si uptake by hyphae. Mechanisms of AMF-induced Si uptake were elucidated: 1) direct Si uptake by hyphae, 2) increased silicate dissolution, and 3) upregulation of Si transporters. Silicon application also increased AMF colonization by 28%, and the absence of interactions was observed on P uptake. Altogether, AMF support Si acquisition and Si fosters AMF colonization in rice, whereas the P uptake depends more on AMF than on Si.
{"title":"Mechanisms of Arbuscular Mycorrhizal Fungi Increasing Silicon Uptake by Rice","authors":"Li-Xue Qiu, Dong-Xing Guan, Yi-Wen Liu, H. Henry Teng, Zi-Bo Li, Alexander Lux, Yakov Kuzyakov, Lena Q. Ma","doi":"10.1021/acs.jafc.4c01487","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c01487","url":null,"abstract":"Arbuscular mycorrhizal fungi (AMF) influence silicon (Si) uptake by plants, but the mechanisms remain unclear. This study investigated the mechanisms of AMF-mediated Si uptake by rice, a model Si-accumulating plant, and explored the tripartite interactions among AMF, Si, and phosphorus (P). AMF inoculation increased shoot Si content by 97% when supplied with silicic acid and by 29% with calcium silicate and upregulated expression of Si transporters <i>Lsi1</i> and <i>Lsi2</i> in roots. Supplying Si only to AMF hyphae increased the root Si content by 113%, indicating direct Si uptake by hyphae. Mechanisms of AMF-induced Si uptake were elucidated: 1) direct Si uptake by hyphae, 2) increased silicate dissolution, and 3) upregulation of Si transporters. Silicon application also increased AMF colonization by 28%, and the absence of interactions was observed on P uptake. Altogether, AMF support Si acquisition and Si fosters AMF colonization in rice, whereas the P uptake depends more on AMF than on Si.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":6.1,"publicationDate":"2024-06-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141464060","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-06-28DOI: 10.1021/acs.jafc.3c09028
Isabella Kimmeswenger, Barbara Lieder
Obesity-related inflammation has been linked to decreased taste sensitivity and changes in the transcriptome of the taste apparatus. Increased levels of pro-inflammatory cytokines can also be found to be food-associated in individuals who consume high amounts of long-chain saturated fatty acids and sucrose independent of the body composition or individuals who exercise intensively. Previous research suggests a link between taste sensitivity and food choices. However, the interplay between food- or exercise-induced low-grade inflammation, taste perception, and food choices remains unaddressed. Understanding this relationship could provide an unnoticed explanation for interindividual differences in taste perception that influences dietary habits.
{"title":"Novel Perspective on the Plasticity of Taste Perception: Is Food- and Exercise-Induced Inflammation Associated with Sweet Taste Sensitivity and Preference?","authors":"Isabella Kimmeswenger, Barbara Lieder","doi":"10.1021/acs.jafc.3c09028","DOIUrl":"https://doi.org/10.1021/acs.jafc.3c09028","url":null,"abstract":"Obesity-related inflammation has been linked to decreased taste sensitivity and changes in the transcriptome of the taste apparatus. Increased levels of pro-inflammatory cytokines can also be found to be food-associated in individuals who consume high amounts of long-chain saturated fatty acids and sucrose independent of the body composition or individuals who exercise intensively. Previous research suggests a link between taste sensitivity and food choices. However, the interplay between food- or exercise-induced low-grade inflammation, taste perception, and food choices remains unaddressed. Understanding this relationship could provide an unnoticed explanation for interindividual differences in taste perception that influences dietary habits.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":6.1,"publicationDate":"2024-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141463529","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}