Pub Date : 2024-07-03DOI: 10.1021/acs.jafc.4c02871
Yuyan Wei, Ling Xie, Bertrand Muhoza, Qian Liu, Shiqing Song
The present study investigated the impact of four chicken liver protein hydrolysate-based cat food attractants on palatability. Aroma compounds were analyzed in these attractants, which were subsequently sprayed onto four different types of cat foods. Results revealed that CF4 exhibited the highest intake ratio and the first choice ratio, followed by CF2 sample. Orthogonal partial least-squares discriminant analysis (OPLS-DA) demonstrated significant differences among 50 volatile compounds identified from the four cat foods. Using variable importance in projection (VIP) values, we selected 17 key flavor compounds responsible for distinguishing between the four cat foods. Peptides with a molecular mass <180 Da showed correlation with nonanoic acid and cedrol, while those >3000 Da correlated with hexanoic acid ethyl ester. Regression coefficients (RCs) calculated from partial least-squares regression (PLSR) results showed positive correlations between compound content and palatability for six compounds, whereas negative correlations were observed for ten compounds. Validation experiments confirmed that nonanal, 2-propylpyridine, and 3-octen-2-one enhanced palatability and correlated with peptides ranging from 180 to 500 Da; conversely, nonanoic acid ethyl ester and 3-methyl-pentanoic acid reduced palatability and correlated with peptides ranging from 1000 to 3000 Da.
本研究调查了四种基于鸡肝蛋白水解物的猫粮引诱剂对适口性的影响。研究人员分析了这些引诱剂的芳香化合物,然后将其喷洒在四种不同类型的猫粮上。结果显示,CF4 的摄入率和首选率最高,其次是 CF2 样品。正交偏最小二乘判别分析(OPLS-DA)表明,从四种猫粮中鉴定出的 50 种挥发性化合物之间存在显著差异。利用预测中的变量重要性(VIP)值,我们选出了 17 种主要风味化合物,它们是区分四种猫粮的关键。分子质量为 3000 Da 的肽与己酸乙酯相关。根据偏最小二乘回归(PLSR)结果计算出的回归系数(RC)显示,六种化合物的含量与适口性呈正相关,而十种化合物呈负相关。验证实验证实,壬醛、2-丙基吡啶和 3-辛烯-2-酮提高了适口性,并与 180 至 500 Da 的肽相关;相反,壬酸乙酯和 3-甲基戊酸降低了适口性,并与 1000 至 3000 Da 的肽相关。
{"title":"Generation of Olfactory Compounds in Cat Food Attractants: Chicken Liver-Derived Protein Hydrolysates and Their Contribution to Enhancing Palatability.","authors":"Yuyan Wei, Ling Xie, Bertrand Muhoza, Qian Liu, Shiqing Song","doi":"10.1021/acs.jafc.4c02871","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c02871","url":null,"abstract":"<p><p>The present study investigated the impact of four chicken liver protein hydrolysate-based cat food attractants on palatability. Aroma compounds were analyzed in these attractants, which were subsequently sprayed onto four different types of cat foods. Results revealed that CF4 exhibited the highest intake ratio and the first choice ratio, followed by CF2 sample. Orthogonal partial least-squares discriminant analysis (OPLS-DA) demonstrated significant differences among 50 volatile compounds identified from the four cat foods. Using variable importance in projection (VIP) values, we selected 17 key flavor compounds responsible for distinguishing between the four cat foods. Peptides with a molecular mass <180 Da showed correlation with nonanoic acid and cedrol, while those >3000 Da correlated with hexanoic acid ethyl ester. Regression coefficients (RCs) calculated from partial least-squares regression (PLSR) results showed positive correlations between compound content and palatability for six compounds, whereas negative correlations were observed for ten compounds. Validation experiments confirmed that nonanal, 2-propylpyridine, and 3-octen-2-one enhanced palatability and correlated with peptides ranging from 180 to 500 Da; conversely, nonanoic acid ethyl ester and 3-methyl-pentanoic acid reduced palatability and correlated with peptides ranging from 1000 to 3000 Da.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141496325","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}
Aflatoxin B1 (AFB1), a mycotoxin and natural carcinogen, commonly contaminates cereals and animal feeds, posing serious health risks to human and animal. In this study, Bacillus amyloliquefaciens ZG08 isolated from kimchi could effectively remove 80.93% of AFB1 within 72 h at 37 °C and pH 7.0. Metabolome and transcriptome analysis showed that metabolic processes including glycerophospholipid metabolism and amino acid metabolism were most affected in B. amyloliquefaciens ZG08 exposed to AFB1. The adaptation mechanism likely involved activation of the thioredoxin system to restore intracellular redox equilibrium. The key genes, tpx and gldA, overexpressed in Escherichia coli BL21, achieved degradation rates of 60.15% and 47.16% for 100 μg/kg AFB1 under optimal conditions of 37 °C and pH 8.0 and 45 °C and pH 7.0, respectively. The degradation products, identified as AFD1, were less cytotoxic than AFB1 in HepG2 cells. These findings suggest potential strategies for utilizing probiotics and engineered enzymes in AFB1 detoxification.
{"title":"Biodegradation Characteristics and Mechanism of Aflatoxin B<sub>1</sub> by <i>Bacillus amyloliquefaciens</i> from Enzymatic and Multiomics Perspectives.","authors":"Honghui Shi, Guoli Chang, Yuhuan Zhang, Yan Zhao, Haifeng Wang, Jinzhi Zhang, Junli Zhu","doi":"10.1021/acs.jafc.4c04055","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c04055","url":null,"abstract":"<p><p>Aflatoxin B<sub>1</sub> (AFB<sub>1</sub>), a mycotoxin and natural carcinogen, commonly contaminates cereals and animal feeds, posing serious health risks to human and animal. In this study, <i>Bacillus amyloliquefaciens</i> ZG08 isolated from kimchi could effectively remove 80.93% of AFB<sub>1</sub> within 72 h at 37 °C and pH 7.0. Metabolome and transcriptome analysis showed that metabolic processes including glycerophospholipid metabolism and amino acid metabolism were most affected in <i>B. amyloliquefaciens</i> ZG08 exposed to AFB<sub>1</sub>. The adaptation mechanism likely involved activation of the thioredoxin system to restore intracellular redox equilibrium. The key genes, <i>tpx</i> and <i>gldA</i>, overexpressed in <i>Escherichia coli</i> BL21, achieved degradation rates of 60.15% and 47.16% for 100 μg/kg AFB<sub>1</sub> under optimal conditions of 37 °C and pH 8.0 and 45 °C and pH 7.0, respectively. The degradation products, identified as AFD<sub>1</sub>, were less cytotoxic than AFB<sub>1</sub> in HepG2 cells. These findings suggest potential strategies for utilizing probiotics and engineered enzymes in AFB<sub>1</sub> detoxification.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141489939","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}
Liver disease has become an important risk factor for global health. Resveratrol (Res) is a natural polyphenol which is widely found in foods and has a variety of biological activities. This study investigated the role of the microbiota-gut-liver axis in the Res relieving the liver fibrosis induced by inorganic mercury exposure. Twenty-eight mice were divided into four groups (n = 7) and treated with mercuric chloride and/or Res for 24 weeks, respectively. The results showed that Res mitigated the ileum injury induced by inorganic mercury and restrained LPS and alcohol entering the body circulation. Network pharmacological and molecular analyses showed that Res alleviated oxidative stress, metabolism disorders, inflammation, and hepatic stellate cell activation in the liver. In conclusion, Res alleviates liver fibrosis induced by inorganic mercury via activating the Sirt1/PGC-1α signaling pathway and regulating the microbial-gut-liver axis, particularly, increasing the relative enrichment of Bifidobacterium in the intestinal tract.
肝病已成为影响全球健康的一个重要风险因素。白藜芦醇(Res)是一种天然多酚,广泛存在于食物中,具有多种生物活性。本研究探讨了微生物群-肠-肝轴在 Res 缓解无机汞暴露诱导的肝纤维化中的作用。28 只小鼠被分为四组(n = 7),分别接受氯化汞和/或 Res 治疗 24 周。结果显示,Res 可减轻无机汞诱导的回肠损伤,并抑制 LPS 和酒精进入体循环。网络药理学和分子分析表明,Res 可减轻肝脏中的氧化应激、代谢紊乱、炎症和肝星状细胞活化。总之,Res 可通过激活 Sirt1/PGC-1α 信号通路和调节微生物-肠-肝轴,特别是增加肠道中双歧杆菌的相对富集度,缓解无机汞诱导的肝纤维化。
{"title":"Resveratrol Alleviates Liver Fibrosis Induced by Long-Term Inorganic Mercury Exposure through Activating the <i>Sirt</i>1/<i>PGC</i>-1α Signaling Pathway.","authors":"Siyu Li, Biqi Han, Jiayi Li, Zhanjun Lv, Huijie Jiang, Yunfeng Liu, Xu Yang, Jingjing Lu, Zhigang Zhang","doi":"10.1021/acs.jafc.4c02349","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c02349","url":null,"abstract":"<p><p>Liver disease has become an important risk factor for global health. Resveratrol (Res) is a natural polyphenol which is widely found in foods and has a variety of biological activities. This study investigated the role of the microbiota-gut-liver axis in the Res relieving the liver fibrosis induced by inorganic mercury exposure. Twenty-eight mice were divided into four groups (<i>n</i> = 7) and treated with mercuric chloride and/or Res for 24 weeks, respectively. The results showed that Res mitigated the ileum injury induced by inorganic mercury and restrained LPS and alcohol entering the body circulation. Network pharmacological and molecular analyses showed that Res alleviated oxidative stress, metabolism disorders, inflammation, and hepatic stellate cell activation in the liver. In conclusion, Res alleviates liver fibrosis induced by inorganic mercury via activating the <i>Sirt</i>1/<i>PGC</i>-1α signaling pathway and regulating the microbial-gut-liver axis, particularly, increasing the relative enrichment of <i>Bifidobacterium</i> in the intestinal tract.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141496330","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 : 2024-07-03DOI: 10.1021/acs.jafc.4c02041
Ju Peng, Yong Zhang, Jingguo Yang, Leliang Zhou, Shangdu Zhang, Xiang Wu, Jixiang Chen, Deyu Hu, Xiuhai Gan
Rice bacterial leaf blight and rice bacterial leaf streak have induced tremendous damage to production of rice worldwide. To discover an effective novel antibacterial agent, a series of novel trans-resveratrol (RSV) derivatives containing 1,3,4-oxadiazole and amide moieties were designed and synthesized for the first time. Most of them showed excellent antibacterial activities against Xanthomonas oryzae pv oryzicola and Xanthomonas oryzae pv oryzae. Especially, compound J12 had the best inhibitory with the half-maximal effective concentration values of 4.2 and 5.0 mg/L, respectively, which were better than that of RSV (63.7 and 75.4 mg/L), bismerthiazol (79.5 and 89.6 mg/L), and thiodiazole copper (105.4 and 112.8 mg/L). Furthermore, compound J12 had an excellent control effect against rice bacterial leaf streak and rice bacterial leaf blight, with protective activities of 46.2 and 42.1% and curative activities of 44.5 and 41.7%, respectively. Preliminary mechanisms indicated that compound J12 could not only remarkably decrease biofilm formation, extracellular polysaccharide production, and the synthesis of extracellular enzymes but also destroy bacterial cell surface morphology, thereby reducing the pathogenicity of bacteria. In addition, compound J12 could increase the activity of defense-related enzymes and affect the expression of multiple pathogenic-related genes including plant-pathogen interaction, the MAPK signaling pathway, and phenylpropanoid biosynthesis, and this could improve the defense of rice against rice bacterial leaf streak infection. The present work indicates that the RSV derivatives can be used as promising candidates for the development of antibacterial agents.
{"title":"Novel <i>trans</i>-Resveratrol Derivatives: Design, Synthesis, Antibacterial Activity, and Mechanisms.","authors":"Ju Peng, Yong Zhang, Jingguo Yang, Leliang Zhou, Shangdu Zhang, Xiang Wu, Jixiang Chen, Deyu Hu, Xiuhai Gan","doi":"10.1021/acs.jafc.4c02041","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c02041","url":null,"abstract":"<p><p>Rice bacterial leaf blight and rice bacterial leaf streak have induced tremendous damage to production of rice worldwide. To discover an effective novel antibacterial agent, a series of novel <i>trans</i>-resveratrol (RSV) derivatives containing 1,3,4-oxadiazole and amide moieties were designed and synthesized for the first time. Most of them showed excellent antibacterial activities against <i>Xanthomonas oryzae</i> pv <i>oryzicola</i> and <i>Xanthomonas oryzae</i> pv <i>oryzae</i>. Especially, compound <b>J12</b> had the best inhibitory with the half-maximal effective concentration values of 4.2 and 5.0 mg/L, respectively, which were better than that of RSV (63.7 and 75.4 mg/L), bismerthiazol (79.5 and 89.6 mg/L), and thiodiazole copper (105.4 and 112.8 mg/L). Furthermore, compound <b>J12</b> had an excellent control effect against rice bacterial leaf streak and rice bacterial leaf blight, with protective activities of 46.2 and 42.1% and curative activities of 44.5 and 41.7%, respectively. Preliminary mechanisms indicated that compound <b>J12</b> could not only remarkably decrease biofilm formation, extracellular polysaccharide production, and the synthesis of extracellular enzymes but also destroy bacterial cell surface morphology, thereby reducing the pathogenicity of bacteria. In addition, compound <b>J12</b> could increase the activity of defense-related enzymes and affect the expression of multiple pathogenic-related genes including plant-pathogen interaction, the MAPK signaling pathway, and phenylpropanoid biosynthesis, and this could improve the defense of rice against rice bacterial leaf streak infection. The present work indicates that the RSV derivatives can be used as promising candidates for the development of antibacterial agents.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141489944","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 : 2024-07-03DOI: 10.1021/acs.jafc.4c02082
Natasha L Hungerford, Diane Ouwerkerk, Rosalind A Gilbert, Zhi Hung Loh, Russell J Gordon, Luis F P Silva, Mary T Fletcher
Pimelea poisoning of cattle causes distinct symptoms and frequently death, attributable to the toxin simplexin. Pimelea poisoning was induced via addition of ground Pimelea trichostachya plant to the daily feed in a three-month trial with Droughtmaster steers. The trial tested four potential mitigation treatments, namely, biochar, activated biochar, bentonite, and a bacterial inoculum, and incorporated negative and positive control groups. All treatments tested were unable to prevent the development of simplexin poisoning effects. However, steers consuming a bentonite adsorbent together with Pimelea showed lesser rates-of-decline for body weight (P < 0.05) and four hematological parameters (P < 0.02), compared to the positive control group fed Pimelea only. Microbiome analysis revealed that despite displaying poisoning symptoms, the rumen microbial populations of animals receiving Pimelea were very resilient, with dominant bacterial populations maintained over time. Unexpectedly, clinical edema developed in some animals up to 2 weeks after Pimelea dosing was ceased.
{"title":"A Feeding Trial to Investigate Strategies to Mitigate the Impacts of <i>Pimelea</i> Poisoning in Australian Cattle.","authors":"Natasha L Hungerford, Diane Ouwerkerk, Rosalind A Gilbert, Zhi Hung Loh, Russell J Gordon, Luis F P Silva, Mary T Fletcher","doi":"10.1021/acs.jafc.4c02082","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c02082","url":null,"abstract":"<p><p><i>Pimelea</i> poisoning of cattle causes distinct symptoms and frequently death, attributable to the toxin simplexin. <i>Pimelea</i> poisoning was induced via addition of ground <i>Pimelea trichostachya</i> plant to the daily feed in a three-month trial with Droughtmaster steers. The trial tested four potential mitigation treatments, namely, biochar, activated biochar, bentonite, and a bacterial inoculum, and incorporated negative and positive control groups. All treatments tested were unable to prevent the development of simplexin poisoning effects. However, steers consuming a bentonite adsorbent together with <i>Pimelea</i> showed lesser rates-of-decline for body weight (<i>P</i> < 0.05) and four hematological parameters (<i>P</i> < 0.02), compared to the positive control group fed <i>Pimelea</i> only. Microbiome analysis revealed that despite displaying poisoning symptoms, the rumen microbial populations of animals receiving <i>Pimelea</i> were very resilient, with dominant bacterial populations maintained over time. Unexpectedly, clinical edema developed in some animals up to 2 weeks after <i>Pimelea</i> dosing was ceased.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141489938","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}
Flow-injection spin-trapping electron paramagnetic resonance (FI-EPR) methods that involve the use of 5,5-dimethyl-pyrroline-N-oxide (DMPO) as a spin-trapping reagent have been developed for the kinetic study of the O2•- radical scavenging reactions occurring in the presence of various plant-derived and synthetic phenolic antioxidants (Aox), such as flavonoid, pyrogallol, catechol, hydroquinone, resorcinol, and phenol derivatives in aqueous media (pH 7.4 at 25 °C). The systematically estimated second-order rate constants (ks) of these phenolic compounds span a wide range (from 4.5 × 10 to 1.0 × 106 M-1 s-1). The semilogarithm plots presenting the relationship between ks values and oxidation peak potential (Ep) values of phenolic Aox are divided into three groups (A1, A2, and B). The ks-Ep plots of phenolic Aox bearing two or three OH moieties, such as pyrogallol, catechol, and hydroquinone derivatives, belonged to Groups A1 and A2. These molecules are potent O2•- radical scavengers with ks values above 3.8 × 104 (M-1 s-1). The ks-Ep plots of all phenol and resorcinol derivatives, and a few catechol and hydroquinone derivatives containing carboxyl groups adjacent to the OH groups, were categorized into the group poor scavengers (ks < 1.6 × 103 M-1 s-1). The ks values of each group correlated negatively with Ep values, supporting the hypothesis that the O2•- radical scavenging reaction proceeds via one-electron and two-proton processes. The processes were accompanied by the production of hydrogen peroxide at pH 7.4. Furthermore, the correlation between the plots of ks and the OH proton dissociation constant (pKa•) of the intermediate aroxyl radicals (ks-pKa• plots) revealed that the second proton transfer process could potentially be the rate-determining step of the O2•- radical scavenging reaction of phenolic compounds. The ks-Ep plots provide practical information to predict the O2•- radical scavenging activity of plant-derived phenolic compounds based on those molecular structures.
{"title":"Mechanisms Associated with Superoxide Radical Scavenging Reactions Involving Phenolic Compounds Deduced Based on the Correlation between Oxidation Peak Potentials and Second-Order Rate Constants Determined Using Flow-Injection Spin-Trapping EPR Methods.","authors":"Yasuhiro Sakurai, Shuhei Yamaguchi, Tomoyuki Yamashita, Yao Lu, Keiko Kuwabara, Tomoko Yamaguchi, Yusuke Miyake, Kenji Kanaori, Seiya Watanabe, Kunihiko Tajima","doi":"10.1021/acs.jafc.4c02873","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c02873","url":null,"abstract":"<p><p>Flow-injection spin-trapping electron paramagnetic resonance (FI-EPR) methods that involve the use of 5,5-dimethyl-pyrroline-<i>N</i>-oxide (DMPO) as a spin-trapping reagent have been developed for the kinetic study of the O<sub>2</sub><sup>•-</sup> radical scavenging reactions occurring in the presence of various plant-derived and synthetic phenolic antioxidants (Aox), such as flavonoid, pyrogallol, catechol, hydroquinone, resorcinol, and phenol derivatives in aqueous media (pH 7.4 at 25 °C). The systematically estimated second-order rate constants (<i>k</i><sub>s</sub>) of these phenolic compounds span a wide range (from 4.5 × 10 to 1.0 × 10<sup>6</sup> M<sup>-1</sup> s<sup>-1</sup>). The semilogarithm plots presenting the relationship between <i>k</i><sub>s</sub> values and oxidation peak potential (<i>E</i><sub>p</sub>) values of phenolic Aox are divided into three groups (A1, A2, and B). The <i>k</i><sub>s</sub>-<i>E</i><sub>p</sub> plots of phenolic Aox bearing two or three OH moieties, such as pyrogallol, catechol, and hydroquinone derivatives, belonged to Groups A1 and A2. These molecules are potent O<sub>2</sub><sup>•-</sup> radical scavengers with <i>k</i><sub>s</sub> values above 3.8 × 10<sup>4</sup> (M<sup>-1</sup> s<sup>-1</sup>). The <i>k</i><sub>s</sub>-<i>E</i><sub>p</sub> plots of all phenol and resorcinol derivatives, and a few catechol and hydroquinone derivatives containing carboxyl groups adjacent to the OH groups, were categorized into the group poor scavengers (<i>k</i><sub>s</sub> < 1.6 × 10<sup>3</sup> M<sup>-1</sup> s<sup>-1</sup>). The <i>k</i><sub>s</sub> values of each group correlated negatively with <i>E</i><sub>p</sub> values, supporting the hypothesis that the O<sub>2</sub><sup>•-</sup> radical scavenging reaction proceeds via one-electron and two-proton processes. The processes were accompanied by the production of hydrogen peroxide at pH 7.4. Furthermore, the correlation between the plots of <i>k</i><sub>s</sub> and the OH proton dissociation constant (p<i>K</i><sub>a</sub><sup>•</sup>) of the intermediate aroxyl radicals (<i>k</i><sub>s</sub>-p<i>K</i><sub>a</sub><sup>•</sup> plots) revealed that the second proton transfer process could potentially be the rate-determining step of the O<sub>2</sub><sup>•-</sup> radical scavenging reaction of phenolic compounds. The <i>k</i><sub>s</sub>-<i>E</i><sub>p</sub> plots provide practical information to predict the O<sub>2</sub><sup>•-</sup> radical scavenging activity of plant-derived phenolic compounds based on those molecular structures.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141496327","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 : 2024-07-03DOI: 10.1021/acs.jafc.4c03655
Xuxuan Zhang, Weilin Yao, Yuanyuan Tang, Ju Ye, Tengfei Niu, Li Yang, Rufeng Wang, Zhengtao Wang
Prenylflavonoids are promising candidates for food additives and functional foods due to their diverse biological activities and potential health benefits. However, natural prenylflavonoids are generally present in low abundance and are limited to specific plant species. Here, we report the biosynthesis of licoflavanone from naringenin and prenol by recombinant Escherichia coli. By investigating the activities of seven different sources of prenyltransferases overexpressed in E. coli toward various flavonoid substrates, the prenyltransferase AnaPT exhibits substrate preference when naringenin serves as the prenyl acceptor. Furthermore, licoflavanone production was successfully achieved by coupling the isopentenol utilization pathway and AnaPT in recombinant E. coli. In addition, the effects of fermentation temperatures, induction temperatures, naringenin concentrations, and substrate feeding strategies were investigated on the biosynthesis of licoflavanone in recombinant E. coli. Consequently, the recombinant E. coli strain capable of improved dimethylallyl diphosphate (DMAPP) supply and suitable for prenylflavonoid biosynthesis increased licoflavanone titers to 142.1 mg/L in a shake flask and to 537.8 mg/L in a 1.3 L fermentor, which is the highest yield for any prenylflavonoids reported to date. These strategies proposed in this study provide a reference for initiating the production of high-value prenylflavonoids.
{"title":"Coupling the Isopentenol Utilization Pathway and Prenyltransferase for the Biosynthesis of Licoflavanone in Recombinant <i>Escherichia coli</i>.","authors":"Xuxuan Zhang, Weilin Yao, Yuanyuan Tang, Ju Ye, Tengfei Niu, Li Yang, Rufeng Wang, Zhengtao Wang","doi":"10.1021/acs.jafc.4c03655","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c03655","url":null,"abstract":"<p><p>Prenylflavonoids are promising candidates for food additives and functional foods due to their diverse biological activities and potential health benefits. However, natural prenylflavonoids are generally present in low abundance and are limited to specific plant species. Here, we report the biosynthesis of licoflavanone from naringenin and prenol by recombinant <i>Escherichia coli</i>. By investigating the activities of seven different sources of prenyltransferases overexpressed in <i>E. coli</i> toward various flavonoid substrates, the prenyltransferase AnaPT exhibits substrate preference when naringenin serves as the prenyl acceptor. Furthermore, licoflavanone production was successfully achieved by coupling the isopentenol utilization pathway and AnaPT in recombinant <i>E. coli</i>. In addition, the effects of fermentation temperatures, induction temperatures, naringenin concentrations, and substrate feeding strategies were investigated on the biosynthesis of licoflavanone in recombinant <i>E. coli</i>. Consequently, the recombinant <i>E. coli</i> strain capable of improved dimethylallyl diphosphate (DMAPP) supply and suitable for prenylflavonoid biosynthesis increased licoflavanone titers to 142.1 mg/L in a shake flask and to 537.8 mg/L in a 1.3 L fermentor, which is the highest yield for any prenylflavonoids reported to date. These strategies proposed in this study provide a reference for initiating the production of high-value prenylflavonoids.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141489940","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 : 2024-07-03DOI: 10.1021/acs.jafc.4c01578
Shan Yang, Jun-Rong Zhang, Mei Li, Yu-Mei Feng, Lin-Li Yang, Zhou-Qing Long, Xiang Zhou, Zhi-Bing Wu, Li-Wei Liu, Song Yang
Benzimidazoles, the representative pharmacophore of fungicides, have excellent antifungal potency, but their simple structure and single site of action have hindered their wider application in agriculture. In order to extend the structural diversity of tubulin-targeted benzimidazoles, novel benzimidazole derivatives were prepared by introducing the attractive pyrimidine pharmacophore. 2-((6-(4-(trifluoromethyl)phenoxy)pyrimidin-4-yl)thio)-1H-benzo[d]imidazole (A25) exhibited optimal antifungal activity against Sclerotinia sclerotiorum (S. s.), affording an excellent half-maximal effective concentration (EC50) of 0.158 μg/mL, which was higher than that of the reference agent carbendazim (EC50 = 0.594 μg/mL). Pot experiments revealed that compound A25 (200 μg/mL) had acceptable protective activity (84.7%) and curative activity (78.1%), which were comparable with that of carbendazim (protective activity: 90.8%; curative activity: 69.9%). Molecular docking displayed that multiple hydrogen bonds and π-π interactions could be formed between A25 and β-tubulin, resulting in a stronger bonding effect than carbendazim. Fluorescence imaging revealed that the structure of intracellular microtubules can be changed significantly after A25 treatment. Overall, these remarkable antifungal profiles of constructed novel benzimidazole derivatives could facilitate the application of novel microtubule-targeting agents.
{"title":"Expanding the Structural Diversity of Tubulin-Targeting Agents: Development of Highly Potent Benzimidazoles for Treating Fungal Diseases.","authors":"Shan Yang, Jun-Rong Zhang, Mei Li, Yu-Mei Feng, Lin-Li Yang, Zhou-Qing Long, Xiang Zhou, Zhi-Bing Wu, Li-Wei Liu, Song Yang","doi":"10.1021/acs.jafc.4c01578","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c01578","url":null,"abstract":"<p><p>Benzimidazoles, the representative pharmacophore of fungicides, have excellent antifungal potency, but their simple structure and single site of action have hindered their wider application in agriculture. In order to extend the structural diversity of tubulin-targeted benzimidazoles, novel benzimidazole derivatives were prepared by introducing the attractive pyrimidine pharmacophore. 2-((6-(4-(trifluoromethyl)phenoxy)pyrimidin-4-yl)thio)-1<i>H</i>-benzo[<i>d</i>]imidazole (<b>A</b><sub><b>25</b></sub>) exhibited optimal antifungal activity against <i>Sclerotinia sclerotiorum</i> (<i>S. s.</i>), affording an excellent half-maximal effective concentration (EC<sub>50</sub>) of 0.158 μg/mL, which was higher than that of the reference agent carbendazim (EC<sub>50</sub> = 0.594 μg/mL). Pot experiments revealed that compound <b>A</b><sub><b>25</b></sub> (200 μg/mL) had acceptable protective activity (84.7%) and curative activity (78.1%), which were comparable with that of carbendazim (protective activity: 90.8%; curative activity: 69.9%). Molecular docking displayed that multiple hydrogen bonds and π-π interactions could be formed between <b>A</b><sub><b>25</b></sub> and β-tubulin, resulting in a stronger bonding effect than carbendazim. Fluorescence imaging revealed that the structure of intracellular microtubules can be changed significantly after <b>A</b><sub><b>25</b></sub> treatment. Overall, these remarkable antifungal profiles of constructed novel benzimidazole derivatives could facilitate the application of novel microtubule-targeting agents.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141496324","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}
Given the low-calorie, high-sweetness characteristics of steviol glycosides (SGs), developing SGs with improved taste profiles is a key focus. Rebaudioside M8 (Reb M8), a novel non-natural SG derivative obtained through glycosylation at the C-13 position of rebaudioside D (Reb D) using glycosyltransferase UGT94E13, holds promise for further development due to its enhanced sweetness. However, the low catalytic activity of UGT94E13 hampers further research and commercialization. This study aimed to improve the enzymatic activity of UGT94E13 through semirational design, and a variant UGT94E13-F169G/I185G was obtained with the catalytic activity improved by 13.90 times. A cascade reaction involving UGT94E13-F169G/I185G and sucrose synthase AtSuSy was established to recycle uridine diphosphate glucose, resulting in an efficient preparation of Reb M8 with a yield of 98%. Moreover, according to the analysis of the distances between the substrate Reb D and enzymes as well as between Reb D and the glucose donor through molecular dynamics simulations, it is found that the positive effect of shortening the distance on glycosylation reaction activity accounts for the improved catalytic activity of UGT94E13-F169G/I185G. Therefore, this study addresses the bottleneck in the efficient production of Reb M8 and provides a foundation for its widespread application in the food industry.
{"title":"Highly Efficient Biosynthesis of Rebaudioside M8 through Structure-Guided Engineering of Glycosyltransferase UGT94E13.","authors":"Lifeng Yang, Mengliang Yang, Zhiwei Deng, Zhengshan Luo, Zhenbo Yuan, Yijian Rao, Yan Zhang","doi":"10.1021/acs.jafc.4c03565","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c03565","url":null,"abstract":"<p><p>Given the low-calorie, high-sweetness characteristics of steviol glycosides (SGs), developing SGs with improved taste profiles is a key focus. Rebaudioside M8 (Reb M8), a novel non-natural SG derivative obtained through glycosylation at the C-13 position of rebaudioside D (Reb D) using glycosyltransferase UGT94E13, holds promise for further development due to its enhanced sweetness. However, the low catalytic activity of UGT94E13 hampers further research and commercialization. This study aimed to improve the enzymatic activity of UGT94E13 through semirational design, and a variant UGT94E13-F169G/I185G was obtained with the catalytic activity improved by 13.90 times. A cascade reaction involving UGT94E13-F169G/I185G and sucrose synthase <i>At</i>SuSy was established to recycle uridine diphosphate glucose, resulting in an efficient preparation of Reb M8 with a yield of 98%. Moreover, according to the analysis of the distances between the substrate Reb D and enzymes as well as between Reb D and the glucose donor through molecular dynamics simulations, it is found that the positive effect of shortening the distance on glycosylation reaction activity accounts for the improved catalytic activity of UGT94E13-F169G/I185G. Therefore, this study addresses the bottleneck in the efficient production of Reb M8 and provides a foundation for its widespread application in the food industry.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141496326","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}
Root-knot nematodes pose a serious threat to crops by affecting production and quality. Over a period of time, substantial work has been done toward the development of effective and environmentally benign nematicidal compounds. However, due to the inefficiencies of previously reported synthetics in achieving the target of safe, selective, and effective treatment, it is necessary to develop new efficacious and safer nematicidal agents considering human health and environment on top priority. This work aims to highlight the efficient and convenient l-proline catalyzed synthesis of pyrano[3,2-c]pyridone and their use as potential nematicidal agents. In vitro results of larval mortality and egg hatching inhibition revealed maximum nematicidal activity against Meloidogyne incognita from compounds 15b, 15m, and 15w with LC50 values of 28.8, 46.8, and 49.18 μg/mL at 48 h, respectively. Under similar conditions, pyrano[3,2-c]pyridones derivatives 15b (LC50 = 28.8 μg/mL) was found at par with LC50 (26.92 μg/mL) of commercial nematicide carbofuran. The in vitro results were further validated with in silico studies with the most active compound 15b nematicidal within the binding to the pocket of acetylcholine esterase (AChE). In docking, binding free energy values for compound 15b were found to be -6.90 kcal/mol. Results indicated that pyrano[3,2-c]pyridone derivatives have the potential to control M. incognita.
{"title":"Design, Synthesis, Nematicidal Evaluation, and Molecular Docking Study of Pyrano[3,2-<i>c</i>]pyridones against <i>Meloidogyne incognita</i>.","authors":"Neelam Yadav, Ravi Kumar, Sarita Sangwan, Vidhi Dhanda, Reena Rani, Sheetu Devi, Anil Duhan, Jayant Sindhu, Sonu Chauhan, Vinod Kumar Malik, Saroj Yadav, Prakash Banakar","doi":"10.1021/acs.jafc.4c00103","DOIUrl":"https://doi.org/10.1021/acs.jafc.4c00103","url":null,"abstract":"<p><p>Root-knot nematodes pose a serious threat to crops by affecting production and quality. Over a period of time, substantial work has been done toward the development of effective and environmentally benign nematicidal compounds. However, due to the inefficiencies of previously reported synthetics in achieving the target of safe, selective, and effective treatment, it is necessary to develop new efficacious and safer nematicidal agents considering human health and environment on top priority. This work aims to highlight the efficient and convenient l-proline catalyzed synthesis of pyrano[3,2-<i>c</i>]pyridone and their use as potential nematicidal agents. <i>In vitro</i> results of larval mortality and egg hatching inhibition revealed maximum nematicidal activity against <i>Meloidogyne incognita</i> from compounds <b>15b</b>, <b>15m</b>, and <b>15w</b> with LC<sub>50</sub> values of 28.8, 46.8, and 49.18 μg/mL at 48 h, respectively. Under similar conditions, pyrano[3,2-<i>c</i>]pyridones derivatives <b>15b</b> (LC<sub>50</sub> = 28.8 μg/mL) was found at par with LC<sub>50</sub> (26.92 μg/mL) of commercial nematicide carbofuran. The <i>in vitro</i> results were further validated with <i>in silico</i> studies with the most active compound <b>15b</b> nematicidal within the binding to the pocket of acetylcholine esterase (AChE). In docking, binding free energy values for compound <b>15b</b> were found to be -6.90 kcal/mol. Results indicated that pyrano[3,2-<i>c</i>]pyridone derivatives have the potential to control <i>M. incognita</i>.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141496323","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}