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Generation of Olfactory Compounds in Cat Food Attractants: Chicken Liver-Derived Protein Hydrolysates and Their Contribution to Enhancing Palatability. 猫粮引诱剂中嗅觉化合物的生成:鸡肝衍生蛋白水解物及其对提高适口性的贡献》(Chicken Liver-Derived Protein Hydrolysates and Their Contribution to Enhanced Palatability.
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 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。
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引用次数: 0
Biodegradation Characteristics and Mechanism of Aflatoxin B1 by Bacillus amyloliquefaciens from Enzymatic and Multiomics Perspectives. 从酶学和多组学角度看淀粉芽孢杆菌对黄曲霉毒素 B1 的生物降解特性和机制
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 10.1021/acs.jafc.4c04055
Honghui Shi, Guoli Chang, Yuhuan Zhang, Yan Zhao, Haifeng Wang, Jinzhi Zhang, Junli Zhu

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.

黄曲霉毒素 B1(AFB1)是一种霉菌毒素和天然致癌物,通常污染谷物和动物饲料,严重危害人类和动物的健康。在这项研究中,从泡菜中分离出的淀粉芽孢杆菌 ZG08 能在 37 °C、pH 值为 7.0 的条件下,在 72 小时内有效去除 80.93% 的 AFB1。代谢组和转录组分析表明,暴露于 AFB1 的淀粉芽孢杆菌 ZG08 受影响最大的代谢过程包括甘油磷脂代谢和氨基酸代谢。适应机制可能涉及激活硫代氧化还原酶系统,以恢复细胞内的氧化还原平衡。在大肠杆菌 BL21 中过表达的关键基因 tpx 和 gldA 在 37 °C 和 pH 8.0 以及 45 °C 和 pH 7.0 的最佳条件下,对 100 μg/kg AFB1 的降解率分别为 60.15% 和 47.16%。经鉴定,降解产物 AFD1 在 HepG2 细胞中的细胞毒性低于 AFB1。这些发现为利用益生菌和工程酶解毒 AFB1 提出了潜在的策略。
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引用次数: 0
Resveratrol Alleviates Liver Fibrosis Induced by Long-Term Inorganic Mercury Exposure through Activating the Sirt1/PGC-1α Signaling Pathway. 白藜芦醇通过激活Sirt1/PGC-1α信号通路缓解长期暴露于无机汞诱发的肝纤维化
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 10.1021/acs.jafc.4c02349
Siyu Li, Biqi Han, Jiayi Li, Zhanjun Lv, Huijie Jiang, Yunfeng Liu, Xu Yang, Jingjing Lu, Zhigang Zhang

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。
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引用次数: 0
Novel trans-Resveratrol Derivatives: Design, Synthesis, Antibacterial Activity, and Mechanisms. 新型反式白藜芦醇衍生物:设计、合成、抗菌活性和机理。
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 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.

水稻细菌性叶枯病和水稻细菌性条纹叶枯病给全世界的水稻生产造成了巨大损失。为了发现一种有效的新型抗菌剂,研究人员首次设计并合成了一系列含有 1,3,4-噁二唑和酰胺分子的新型反式白藜芦醇(RSV)衍生物。其中大部分对黄单胞菌(Xanthomonas oryzae pv oryzicola)和黄单胞菌(Xanthomonas oryzae pv oryzae)表现出优异的抗菌活性。其中,化合物 J12 的抑菌效果最好,其半最大有效浓度值分别为 4.2 和 5.0 mg/L,优于 RSV(63.7 和 75.4 mg/L)、双噻唑(79.5 和 89.6 mg/L)和硫代唑铜(105.4 和 112.8 mg/L)。此外,化合物 J12 对水稻细菌性叶斑病和水稻细菌性叶枯病有很好的防治效果,保护活性分别为 46.2%和 42.1%,治疗活性分别为 44.5%和 41.7%。初步机制表明,化合物 J12 不仅能显著减少生物膜的形成、胞外多糖的产生和胞外酶的合成,还能破坏细菌细胞表面形态,从而降低细菌的致病性。此外,化合物 J12 还能提高防御相关酶的活性,影响多种致病相关基因的表达,包括植物与病原菌相互作用、MAPK 信号通路和苯丙类生物合成,从而提高水稻对水稻细菌性叶斑病的防御能力。本研究结果表明,RSV 衍生物可作为开发抗菌剂的候选物质。
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引用次数: 0
A Feeding Trial to Investigate Strategies to Mitigate the Impacts of Pimelea Poisoning in Australian Cattle. 一项饲喂试验,旨在研究减轻澳大利亚牛皮米莱中毒影响的策略。
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 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.

牛的姬松茸中毒会导致明显的症状,并经常因毒素单毒素而死亡。在一项为期三个月的试验中,通过在旱阉牛的日常饲料中添加磨碎的 Pimelea trichostachya 植物,诱发了 Pimelea 中毒。试验测试了四种潜在的缓解处理方法,即生物炭、活性生物炭、膨润土和细菌接种体,并纳入了阴性和阳性对照组。所有测试的处理方法都无法防止简单毒素中毒效应的发生。不过,与只喂食 Pimelea 的阳性对照组相比,同时食用膨润土吸附剂和 Pimelea 的母牛的体重下降率(P < 0.05)和四项血液学参数下降率(P < 0.02)较低。微生物组分析表明,尽管出现了中毒症状,但接受 Pimelea 治疗的动物的瘤胃微生物种群具有很强的复原力,优势细菌种群随着时间的推移得以维持。意想不到的是,一些动物在停止服用 Pimelea 两周后出现了临床水肿。
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引用次数: 0
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. 根据使用流动注射自旋俘获 EPR 方法测定的氧化峰电位与二阶速率常数之间的相关性,推断出涉及酚类化合物的超氧自由基清除反应的相关机制
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 10.1021/acs.jafc.4c02873
Yasuhiro Sakurai, Shuhei Yamaguchi, Tomoyuki Yamashita, Yao Lu, Keiko Kuwabara, Tomoko Yamaguchi, Yusuke Miyake, Kenji Kanaori, Seiya Watanabe, Kunihiko Tajima

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.

研究人员开发了流动注射自旋俘获电子顺磁共振(FI-EPR)方法,使用5,5-二甲基吡咯啉-N-氧化物(DMPO)作为自旋俘获试剂,在水介质(pH 7.4,25 °C)。系统估算的这些酚类化合物的二阶速率常数(ks)范围很广(从 4.5 × 10 到 1.0 × 106 M-1 s-1)。呈现 ks 值和酚类 Aox 氧化峰电位(Ep)值之间关系的半对数图分为三组(A1、A2 和 B)。含有两个或三个羟基的酚醛氧化物(如焦棓醇、儿茶酚和对苯二酚衍生物)的 ks-Ep 图属于 A1 和 A2 组。这些分子是强效的 O2 自由基清除剂,其 ks 值超过 3.8 × 104 (M-1 s-1)。所有苯酚和间苯二酚衍生物的 ks-Ep 图,以及少数儿茶酚和对苯二酚衍生物的 ks-Ep 图都被归类为差清除剂组(ks < 1.6 × 103 M-1 s-1)。各组的 ks 值与 Ep 值呈负相关,支持了 O2 自由基清除反应通过单电子和双质子过程进行的假设。在 pH 值为 7.4 时,这些过程伴随着过氧化氢的产生。此外,ks图与中间羟自由基的OH质子解离常数(pKa-)之间的相关性(ks-pKa-图)表明,第二质子转移过程可能是酚类化合物O2自由基清除反应的速率决定步骤。ks-Ep 图为根据这些分子结构预测植物源酚类化合物的 O2 自由基清除活性提供了实用信息。
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引用次数: 0
Coupling the Isopentenol Utilization Pathway and Prenyltransferase for the Biosynthesis of Licoflavanone in Recombinant Escherichia coli. 在重组大肠杆菌中将异戊烯醇利用途径和异戊烯基转移酶耦合用于甘草黄酮的生物合成。
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 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.

由于具有多种生物活性和潜在的健康益处,异戊基黄酮类化合物有望成为食品添加剂和功能食品的候选成分。然而,天然前酰基类黄酮的含量通常很低,而且仅限于特定的植物物种。在此,我们报告了重组大肠杆菌从柚皮苷和前胡醇中生物合成地衣黄烷酮的情况。通过研究在大肠杆菌中过表达的七种不同来源的前酰转移酶对各种类黄酮底物的活性,当柚皮苷作为前酰基受体时,前酰基转移酶 AnaPT 表现出底物偏好。此外,通过在重组大肠杆菌中将异戊烯醇利用途径与 AnaPT 相结合,成功实现了地黄烷酮的生产。此外,还研究了发酵温度、诱导温度、柚皮苷浓度和底物喂养策略对重组大肠杆菌生物合成甘草黄酮的影响。结果表明,重组大肠杆菌菌株能够改善二甲基烯丙基二磷酸(DMAPP)的供应,并适合进行前酰基类黄酮的生物合成,其甘草黄酮滴度在摇瓶中提高到 142.1 mg/L,在 1.3 L 发酵罐中提高到 537.8 mg/L,这是迄今为止所报道的前酰基类黄酮的最高产量。本研究提出的这些策略为开始生产高价值的前黄酮类化合物提供了参考。
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引用次数: 0
Expanding the Structural Diversity of Tubulin-Targeting Agents: Development of Highly Potent Benzimidazoles for Treating Fungal Diseases. 扩大微管蛋白靶向药物的结构多样性:开发治疗真菌疾病的强效苯并咪唑类药物。
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 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.

苯并咪唑是杀真菌剂的代表性药源,具有出色的抗真菌效力,但其结构简单、作用部位单一,阻碍了其在农业领域的广泛应用。为了扩展以小管蛋白为靶标的苯并咪唑类化合物的结构多样性,研究人员通过引入具有吸引力的嘧啶药效团制备了新型苯并咪唑衍生物。2-((6-(4-(三氟甲基)苯氧基)嘧啶-4-基)硫)-1H-苯并[d]咪唑(A25)对硬皮病菌(S. s.)具有最佳的抗真菌活性,其半最大有效浓度(EC50)为 0.158 μg/mL,高于参比制剂多菌灵(EC50 = 0.594 μg/mL)。盆栽实验显示,化合物 A25(200 μg/mL)具有可接受的保护活性(84.7%)和治疗活性(78.1%),与多菌灵(保护活性:90.8%;治疗活性:69.9%)相当。分子对接显示,A25与β-tubulin之间可形成多个氢键和π-π相互作用,从而产生比多菌灵更强的结合效应。荧光成像显示,经 A25 处理后,细胞内微管的结构会发生显著变化。总之,所构建的新型苯并咪唑衍生物具有显著的抗真菌特性,有助于新型微管靶向药物的应用。
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引用次数: 0
Highly Efficient Biosynthesis of Rebaudioside M8 through Structure-Guided Engineering of Glycosyltransferase UGT94E13. 通过糖基转移酶 UGT94E13 的结构引导工程,高效生物合成 Rebaudioside M8。
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 10.1021/acs.jafc.4c03565
Lifeng Yang, Mengliang Yang, Zhiwei Deng, Zhengshan Luo, Zhenbo Yuan, Yijian Rao, Yan Zhang

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.

鉴于甜菊糖苷(SGs)具有低热量、高甜度的特点,开发口味更佳的甜菊糖苷是一个重点。甜菊糖甙 M8(Reb M8)是一种新型的非天然甜菊糖甙衍生物,通过使用糖基转移酶 UGT94E13 在甜菊糖甙 D(Reb D)的 C-13 位进行糖基化而获得。然而,UGT94E13 的催化活性较低,阻碍了进一步的研究和商业化。本研究旨在通过半合成设计提高 UGT94E13 的酶活性,结果得到了一个变体 UGT94E13-F169G/I185G,其催化活性提高了 13.90 倍。通过 UGT94E13-F169G/I185G 与蔗糖合成酶 AtSuSy 的级联反应,实现了二磷酸尿苷葡萄糖的循环利用,从而高效制备了 Reb M8,收率高达 98%。此外,通过分子动力学模拟分析底物 Reb D 与酶以及 Reb D 与葡萄糖供体之间的距离,发现 UGT94E13-F169G/I185G 催化活性的提高是由于缩短距离对糖基化反应活性的积极影响。因此,本研究解决了 Reb M8 高效生产的瓶颈问题,为其在食品工业中的广泛应用奠定了基础。
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引用次数: 0
Design, Synthesis, Nematicidal Evaluation, and Molecular Docking Study of Pyrano[3,2-c]pyridones against Meloidogyne incognita. 针对黑僵菌的吡喃并[3,2-c]吡啶酮的设计、合成、杀线虫评价和分子对接研究
IF 5.7 1区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY Pub Date : 2024-07-03 DOI: 10.1021/acs.jafc.4c00103
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

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.

根结线虫会影响农作物的产量和质量,对农作物构成严重威胁。长期以来,人们在开发有效且对环境无害的杀线虫化合物方面做了大量工作。然而,由于之前报道的合成物在实现安全、选择性和有效治疗目标方面效率不高,因此有必要开发新的高效和更安全的杀线虫剂,将人类健康和环境放在首位。本研究旨在强调高效、便捷的 l-脯氨酸催化合成吡喃并[3,2-c]吡啶酮及其作为潜在杀线虫剂的用途。体外幼虫死亡率和卵孵化抑制结果显示,化合物 15b、15m 和 15w 对 Meloidogyne incognita 的杀线虫活性最高,48 小时的半数致死浓度分别为 28.8、46.8 和 49.18 μg/mL。在类似条件下,吡喃并[3,2-c]吡啶酮衍生物 15b(半数致死浓度 = 28.8 μg/mL)与商品杀线虫剂呋喃丹的半数致死浓度(26.92 μg/mL)相当。体外研究结果通过与乙酰胆碱酯酶(AChE)口袋结合的最有效化合物 15b 的杀线虫活性进行的硅学研究得到了进一步验证。在对接过程中,发现化合物 15b 的结合自由能值为 -6.90 kcal/mol。结果表明,吡喃并[3,2-c]吡啶酮衍生物具有防治线虫的潜力。
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Journal of Agricultural and Food Chemistry
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