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Impact of Seasonal Variation on Antioxidant, Enzyme Inhibitory, and Anti-Inflammatory Potentials of Cistus creticus Leaf Extracts 季节变化对山楂叶提取物抗氧化、酶抑制和抗炎活性的影响。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-21 DOI: 10.1002/open.202500362
Khalil Guelifet, Mokhtar Benmohamed, Khaled Kherraz, Latifa Khattabi, Barbara Sawicka, Ayomide Victor Atoki, Abderrazek Ferhat, Lilya Harchaoui, Mohamed Amine Ferhat, Wafa Zahnit, Afaf Khadra Bendrihem, Mohammed Messaoudi

This study investigates the influence of seasonal variation onthe phytochemicalcomposition and biological activities of Cistus creticus leaf extracts collected during spring, summer, autumn, and winter. Extracts are analyzed for phenolic and flavonoid contents and evaluated for antioxidant, enzyme inhibitory, anti-inflammatory, analgesic, antimicrobial, and photoprotective properties. Pronounced seasonal differences are observed. Spring and summer extracts, enriched in bioactive compounds, exhibit the strongest pharmacological potential, including notable antioxidant effects, potent enzyme inhibition, and high photoprotective capacity. The spring extract further demonstrates significant in vivo anti-inflammatory and analgesic effects, while the winter extract displays superior in vitro anti-inflammatory activity. These findings highlight the critical role of harvest season in modulating both phytochemical composition and bioefficacy. The superior performance of spring and summer extracts underscores the potential of C. creticus as a valuable natural source of antioxidants, enzyme inhibitors, and photoprotective agents. Overall, this work supports the strategic use of seasonal optimization to enhance the therapeutic and cosmeceutical applications of C. creticus.

研究了春、夏、秋、冬4个季节采集的山楂叶提取物的季节变化对其植物化学成分和生物活性的影响。对提取物的酚类和类黄酮含量进行了分析,并对其抗氧化、酶抑制、抗炎、镇痛、抗菌和光保护性能进行了评价。观察到明显的季节差异。春季和夏季提取物富含生物活性化合物,表现出最强的药理潜力,包括显著的抗氧化作用,有效的酶抑制和高光保护能力。春季提取物进一步显示出显著的体内抗炎和镇痛作用,而冬季提取物显示出较好的体外抗炎活性。这些发现强调了收获季节在调节植物化学成分和生物功效方面的关键作用。春夏提取物的优异性能凸显了红草作为抗氧化剂、酶抑制剂和光保护剂的宝贵天然来源的潜力。总的来说,这项工作支持策略性地利用季节优化来提高红草的治疗和药妆应用。
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引用次数: 0
Molecular Networking-Driven Chemical Profiling, Characterization, and Antibacterial Effects of Cuo Nanoparticles Synthesized from Citrus Unshiu Peel Extract 基于分子网络驱动的柑橘青皮提取物纳米Cuo的化学分析、表征及抗菌作用。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-19 DOI: 10.1002/open.202500374
Livhuwani Mafhala, Shohreh Azizi, Garland More, Ilunga Kamika

Molecular networking has emerged as a new in silico tool for analyzing liquid chromatography–mass spectrometry (LC–MS) data for better annotation and elucidation of novel compounds and different pathways. Green synthesized nanoparticles (NPs) have gained considerable attention as a result of their effectiveness in possessing good antimicrobial activity. Their eco-friendly nature and cost-effective synthesis have positioned them as sustainable nanomaterials in various fields. However, not much is known about the mechanism underlying the green synthesis of NPs. Therefore, herein, the copper oxide NPs (CuO NPs) are fabricated, and ultrahigh performance liquid chromatography-quadrupole time of flight mass spectrometry based molecular networking is utilized to understand the phytochemical relationship between the crude extract and the NPs, outlining metabolites that might be involved in reduction. Moreover, CuO NPs synthesized from Citrus unshiu fruit peels are tested for their antimicrobial and cytotoxic activities. Various characterization methods, such as X-ray diffraction, UV–vis spectroscopy, scanning electron microscopy-energy dispersive X-ray analysis, Fourier transform infrared, dynamic light scattering, and transmission electron microscopy, are employed to provide comprehensive insights into the atomic and structural characteristics of NPs. Molecular network reveals the presence of different metabolites such as isosakuranetin-7-O-rutinoside, hesperidin, skullcapflavone II, homoorientin, eupatorin-5-methylether, scoparin, and vitexin, which are recognized as antimicrobial and reducing agents. Additionally, the synthesized CuO NPs show exceptional antibacterial efficacy with a low minimum inhibitory concentration on Staphylococcus aureus, Bacillus cereus, Escherichia coli, and Salmonella typhimurium, highlighting the potential of using LC–MS to explain the antimicrobial properties and green synthesis pathway.

分子网络已经成为一种新的分析液相色谱-质谱(LC-MS)数据的计算机工具,可以更好地注释和阐明新化合物和不同的途径。绿色合成纳米颗粒(NPs)因其具有良好的抗菌活性而受到广泛关注。它们的生态友好性和低成本合成使它们成为各个领域的可持续纳米材料。然而,人们对NPs绿色合成的机制知之甚少。因此,本文制备了氧化铜NPs (CuO NPs),并利用基于分子网络的超高性能液相色谱-四极杆飞行时间质谱技术来了解粗提取物与NPs之间的植物化学关系,概述可能参与还原的代谢物。此外,还研究了从柑桔果皮中合成的CuO NPs的抑菌活性和细胞毒活性。利用x射线衍射、紫外可见光谱、扫描电子显微镜-能量色散x射线分析、傅里叶变换红外、动态光散射和透射电子显微镜等多种表征方法,全面了解NPs的原子和结构特征。分子网络揭示了不同代谢物的存在,如异紫苏苷-7- o -rutinoside、橙皮苷、黄芩黄酮II、同源物苷、紫苏苷-5-甲基醚、东莨菪碱和牡荆素,它们被认为是抗菌和还原剂。此外,合成的CuO NPs对金黄色葡萄球菌、蜡样芽孢杆菌、大肠杆菌和鼠伤寒沙门氏菌具有较低的最低抑菌浓度,具有优异的抑菌效果,这凸显了利用LC-MS解释其抑菌特性和绿色合成途径的潜力。
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引用次数: 0
Polylactic- Glycolic Acid Microparticles–Encapsulated Prostaglandin E1 as A Novel Strategy In Triple Negative Breast Cancer 聚乳酸-乙醇酸微颗粒包封前列腺素E1作为治疗三阴性乳腺癌的新策略。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-19 DOI: 10.1002/open.202500364
Concetta Di Natale, Elena Lagreca, Raffaele Crispino, Roberta D’Auria, Alessandro Attanasio, Rezvan Jamaledin, Raffaele Vecchione, Paolo Antonio Netti

Triple-negative breast cancer (TNBC) is characterized by unique clinical and pathological traits, from which its aggressive nature and the absence of specific treatments are the most worrying. Prostaglandin E1 (PGE1) can affect the morphology of human breast tumor cell lines, but its potential therapeutic effects appear to be counteracted by its high degradability in physiological environments. For this reason, polylactic-glycolic acid polymeric microparticles (MPs) are developed to stabilize PGE1 in damp conditions and enable sustained local release for the treatment of TNBC after surgical removal of the tumor mass. Specifically, the PGE1 embedded MPs are produced using a double emulsion solvent-evaporation method, then analyzed through Mastersizer and scanning electron microscopy. Afterward, the encapsulation efficiency and the PGE1 release are examined using liquid chromatography–mass spectrometry, and their stability at various storage temperatures is assessed. Finally, the carrier toxicity is evaluated in TNBC cells and colon adenocarcinoma epithelial cells, Caco-2. A reliable action on carcinogenic cells specific to breast cancer is observed. Although in vivo studies are still needed, these results open the way to using such a carrier for the intralesional delivery of PGE1 and its use against TNBC.

三阴性乳腺癌(TNBC)具有独特的临床和病理特征,其侵袭性和缺乏特异性治疗是最令人担忧的。前列腺素E1 (PGE1)可以影响人乳腺肿瘤细胞系的形态,但其潜在的治疗作用似乎被其在生理环境中的高降解性所抵消。因此,聚乳酸-乙醇酸聚合物微颗粒(MPs)被开发用于在潮湿条件下稳定PGE1,并在手术切除肿瘤块后实现局部持续释放,用于TNBC的治疗。具体而言,采用双乳液溶剂蒸发法制备了PGE1包埋MPs,并通过浆料粒度仪和扫描电镜进行了分析。随后,采用液相色谱-质谱法检测了PGE1的包封效率和释放量,并评估了其在不同储存温度下的稳定性。最后,在TNBC细胞和结肠腺癌上皮细胞Caco-2中评估载体毒性。观察到对乳腺癌特异性致癌细胞的可靠作用。虽然还需要进行体内研究,但这些结果为使用这种载体局部内递送PGE1及其用于TNBC开辟了道路。
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引用次数: 0
One-Pot Synthesis of Novel β-Carboline-{α-Acylaminoamide}-Bisindole Derivatives: Antibacterial Evaluation, Molecular Docking, and Density Functional Theory Studies 新型β-卡波林-{α-酰基氨基酰胺}-双吲哚衍生物的一锅合成:抗菌评价、分子对接和密度泛函理论研究。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-17 DOI: 10.1002/open.202500245
Ankit Kumar Atri, Lavanya Khullar, Gobind Kumar, Sahil Mishra, Tamanna Dua, Vinay Singh, Kusum Harjai, Parvesh Singh, Vasundhara Singh

A new series of β-carboline-{α-acylaminoamide}-bisindole hybrids (12a–l) is designed and synthesized employing an atom-economical one-pot Ugi four-component reaction (U-4CR), affording the target compounds in good yields. All synthesized compounds (12a–l) are characterized by NMR, infrared, and mass spectrometry and evaluated for their antibacterial activity against both Gram-positive and Gram-negative strains. Notably, compounds 12b, 12g, and 12h display comparable minimum inhibitory concentrations values (302–303 µg mL−1) against multidrug-resistant Acinetobacter baumannii and Pseudomonas aeruginosa, showing markedly improved activity relative to their parent compounds 6 and 9, which show weaker inhibition (MIC = 308–623 µg mL−1). Molecular docking studies of compounds 12g and 12h revealed favorable binding interactions with DNA gyrase, while density functional theory analysis supported their electronic reactivity. These findings highlight the potential of molecular hybridization in the development of novel antibacterial agents.

采用原子经济的一锅Ugi四组分反应(U-4CR),设计并合成了一系列新的β-羰基胺-{α-酰基氨基酰胺}-双吲哚杂合物(12a-l),得到了产率较高的目标化合物。所有合成的化合物(12a-l)都通过核磁共振、红外和质谱进行了表征,并对其对革兰氏阳性和革兰氏阴性菌株的抗菌活性进行了评估。值得注意的是,化合物12b、12g和12h对多药耐药鲍曼不动杆菌和铜绿假单胞菌的最低抑制浓度值(302-303µg mL-1)相当,与母体化合物6和9相比,活性明显提高,母体化合物6和9的抑制作用较弱(MIC = 308-623µg mL-1)。化合物12g和12h的分子对接研究表明它们与DNA旋切酶具有良好的结合作用,而密度泛函理论分析支持它们的电子反应性。这些发现突出了分子杂交在新型抗菌剂开发中的潜力。
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引用次数: 0
Advancements in Catalyst Design for Biomass-Derived Bio-Oil Upgrading to Sustainable Biojet Fuel: A Comprehensive Review 生物质衍生生物油转化为可持续生物喷气燃料催化剂设计进展综述。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-14 DOI: 10.1002/open.202500353
Thandiswa Jideani, Ntalane Sello Seroka, Lindiwe Khotseng

Biomass-derived bio-oil, produced through thermochemical methods such as pyrolysis and hydrothermal liquefaction, has immense potential as a renewable feedstock for aviation fuels because of its renewable nature and the potential to significantly reduce greenhouse gas emissions. The development of biojet fuel from renewable sources, such as biomass, is a critical step toward achieving global energy sustainability and reducing the carbon footprint of the aviation industry. This review aims to provide a comprehensive analysis of the advances in catalyst design to upgrade biomass-derived oil to biojet fuel. The review will also explore the mechanisms by which these catalysts operate, the optimization of catalytic processes, and the performance metrics used to evaluate their efficiency. Recent case studies demonstrate the effectiveness of catalyst design in enabling efficient and sustainable conversion of biomass-based bio-oil into high-quality fuels, advancing the viability of renewable energy sources in aviation and beyond.

通过热化学方法(如热解和水热液化)生产的生物质衍生生物油,由于其可再生性质和显著减少温室气体排放的潜力,作为航空燃料的可再生原料具有巨大的潜力。利用生物质能等可再生资源开发生物喷气燃料,是实现全球能源可持续性和减少航空业碳足迹的关键一步。本文综述了将生物质衍生油转化为生物喷气燃料的催化剂设计的最新进展。本综述还将探讨这些催化剂的运作机制,催化过程的优化,以及用于评估其效率的性能指标。最近的案例研究表明,催化剂设计在将生物质基生物油高效、可持续地转化为高质量燃料方面是有效的,从而提高了可再生能源在航空等领域的可行性。
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引用次数: 0
Morphological Modification of Metal Oxide Nanomaterials Using Different Types of Organic Modifiers 不同类型有机改性剂对金属氧化物纳米材料形态的修饰。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-13 DOI: 10.1002/open.202500342
Taskiya Akter, Asiful Islam, Abdullah Al Miad, Md. Kawcher Alam, Samina Ahmed, Md. Sahadat Hossain

Organic modifiers make incorporating nanoparticles into composite components easier, improving their optical, mechanical, and electrical characteristics. By altering the dimension, arrangement, aggregation, and surface characteristics of the nanoparticles, organic modifiers are thought to be an efficient way to regulate the morphology of nanometal oxides. This can be evaluated by the synthesis and modification of nanometal oxides using various organic agents, such as tiny ligands, various acids, polymers, and so on. Organic modifiers improve crystallinity, bind to oxide surfaces efficiently, and cause morphological changes, reducing agglomeration, raising surface roughness, and exposing more reactive facets according to XRD, FT-IR, BET, SEM, and TEM investigations. In comparison to unmodified oxides, the results showed that organic modifiers greatly decreased agglomeration, regulated particle size distribution, and improved crystallinity. In general, surface modification with organic modifiers is necessary to maximize the effectiveness of nanoparticles for many reasons, such as materials research, drug delivery, diagnosis, and catalytic processes. In this review, we primarily presented several methods for applying organic modifiers to modify the surface of nanocrystals. Here, we mainly focused on the structural modification of six types of metal oxides (TiO2, Fe3O4, ZnO, Al2O3, CuO, NiO) via organic modifiers that are commonly used in various nanoparticle-based applications. The reason behind choosing these six nanoparticles is that they are common in use and there are no such review papers where all the surface modification information is accumulated. The results of this study will assist future researchers in carefully choosing organic modifiers that can be used as a successful method of modifying the morphology of nanometal oxides to satisfy particular functional requirements in technologically sophisticated applications. The importance of organic modifiers in developing nanoparticle technology and propelling advancements in various scientific and industrial fields is also highlighted in this review.

有机改性剂使纳米颗粒更容易融入复合材料组件,改善其光学、机械和电学特性。通过改变纳米颗粒的尺寸、排列、聚集和表面特征,有机改性剂被认为是调节纳米金属氧化物形态的有效途径。这可以通过使用各种有机试剂(如微小配体、各种酸、聚合物等)合成和修饰纳米金属氧化物来评估。根据XRD, FT-IR, BET, SEM和TEM的研究,有机改性剂提高了结晶度,有效地结合到氧化物表面,并引起形态变化,减少团聚,提高表面粗糙度,并暴露出更多的活性面。结果表明,与未经改性的氧化物相比,有机改性剂可显著减少团聚,调节粒径分布,提高结晶度。一般来说,由于材料研究、药物传递、诊断和催化过程等多种原因,使用有机改性剂进行表面改性是使纳米颗粒的有效性最大化所必需的。本文主要介绍了几种应用有机改性剂修饰纳米晶体表面的方法。在这里,我们主要研究了六种金属氧化物(TiO2, Fe3O4, ZnO, Al2O3, CuO, NiO)的结构改性,这些改性剂通常用于各种基于纳米粒子的应用。选择这六种纳米粒子的原因是它们在使用中很常见,并且没有这样的综述论文,其中所有的表面改性信息都是积累的。这项研究的结果将帮助未来的研究人员仔细选择有机改性剂,这些改性剂可以作为一种成功的方法来修饰纳米金属氧化物的形态,以满足技术复杂应用中的特定功能要求。本文还强调了有机改性剂在发展纳米颗粒技术和推动各个科学和工业领域进步方面的重要性。
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引用次数: 0
Exploration of Cytotoxicity and Antibacterial Activities of M-Ceo2 (M = Ag, Cu, Te, and Ta) Nanoparticles M- ceo2 (M = Ag, Cu, Te和Ta)纳米颗粒的细胞毒性和抗菌活性的探索。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-12 DOI: 10.1002/open.202500278
Faiza Qureshi, Suhailah S. Aljameel, Muhammad Nawaz, Mohammad Azam Ansari, Firdos Alam Khan, Sultan Akhtar, Mariam Ali Alsayed, Mohammad J. Akbar,  Muzaheed

This study focuses on the ultrasonic synthesis of M-CeO2 (M = Ag, Cu, Te & Ta) nanoparticles (NPs) and screening of their cytotoxicity and antibacterial activities. The prepared NPs are characterized by different techniques such as X-ray diffraction, transmission electron microscope, SEM-EDX,DR-UV-visible spectrophotometer, and dynamic light scattering analysis. The cytotoxicity of M-CeO2 nanoparticles are assessed against cancer cells such as colorectal carcinoma (HCT-116) and cervical cancer cells (HeLa) and non-cancer cells (embryonic kidney cells HEK-293). The effect of post-48 h treatment of CeO2, Ag-CeO2, Cu-CeO2, Te-CeO2, and Ta-CeO2, on HCT-116 and HeLa cells showed a noteworthy reduction in cell viability. The treatments of Ag-CeO2 also display a reduction in cancer cell viability but statistically not significant. The treatment of CeO2 shows better inhibitory action on HCT-116 and HeLa cells. HEK-293 is treated with CeO2, Ag-CeO2, Cu-CeO2, Te-CeO2, and Ta-CeO2 NPs with the same dosages, there is a minor decline in the cell number, but the percentage of cells viability is greater than HCT-116 and HeLa cells. The antibacterial activity of NPs against E. coli and S. aureus is tested, and Te-CeO2 NPs show better antibacterial activity. The lowest MIC displayed by Te-CeO2 is 0.25 mg mL−1 against E. coli and 4 mg mL−1 for S. aureus, respectively.

本文研究了超声波合成M- ceo2 (M = Ag, Cu, Te和Ta)纳米粒子(NPs),并对其细胞毒性和抗菌活性进行了筛选。采用x射线衍射、透射电子显微镜、SEM-EDX、dr - uv -可见分光光度计和动态光散射等技术对所制备的纳米粒子进行了表征。M-CeO2纳米颗粒对结肠癌细胞(HCT-116)、宫颈癌细胞(HeLa)和非癌细胞(胚胎肾细胞HEK-293)的细胞毒性进行了评估。CeO2、Ag-CeO2、Cu-CeO2、Te-CeO2和Ta-CeO2处理48 h后对HCT-116和HeLa细胞的影响显示细胞活力明显降低。Ag-CeO2治疗也显示癌细胞活力降低,但统计学上不显著。CeO2处理对HCT-116和HeLa细胞有较好的抑制作用。同样剂量的CeO2、Ag-CeO2、Cu-CeO2、Te-CeO2、Ta-CeO2 NPs处理HEK-293,细胞数量略有下降,但细胞存活率高于HCT-116和HeLa细胞。对NPs对大肠杆菌和金黄色葡萄球菌的抑菌活性进行了测试,Te-CeO2 NPs表现出较好的抑菌活性。Te-CeO2对大肠杆菌和金黄色葡萄球菌的最低MIC分别为0.25 mg mL-1和4 mg mL-1。
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引用次数: 0
Development of 5-Amino-2,4,6-triiodoisophthalic Acid Derivatives for Carbamoylation of Amino Acids 氨基酸氨基甲酰化的5-氨基-2,4,6-三碘二苯二甲酸衍生物的研究。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-12 DOI: 10.1002/open.202500174
Kousaku Ohkawa, Tracy Nguyen, Chloe Jin, Hemdeep Kaur, Beatrice Mae Malvar, Rebecca Back, Parisa Khosropour, Shuichi Suzuki, Frank P. K. Hsu, Ichiro Yuki

Herein, 5-amino-2,4,6-triiodoisophthalic acid (ATIIPA) is used as a nucleophile to produce the corresponding 1,3-diesters. Two types of 1,3-diesters, i) diethyl 5-amino-2,4,6-triiodoisophthalate (DEtTIIP) and ii) diacetoxyethyl 5-amino-2,4,6-triiodoisophthalate (DAcOEtTIIP), are mostly prepared in quantitative yields. The 1,3-esters are tested as a carbamoylation agent toward the amino groups of the βAla esters via isocyanation of the 5-amino group. The addition reaction of DEtTIIP-NCO and βAla-OEt yields DEtTIIP:CO-βAla-OEt, and the 1,3-diethyl ester is highly resistant to alkaline hydrolysis due to the steric shielding by the adjacent 2,4,6-iodines, while the α-ethyl ester of the βAla substructure is easily removed. Alkaline hydrolysis of another adduct, DAcOEtTIIP:CO-βAla-OtBu, removes only the 1,3-acetoxy ethyl groups to form the product DAcOHTIIP:CO-βAla-OtBu, and the acidic fission of the -OtBu ester is quantitative to give DAcOEtTIIP:CO-βAla. These results indicate that the DAcOEtTIIP is a feasible precursor for the N-carbamoylation of the amino acid esters, preserving the freedom for selective ester deprotection, which further inspires the design of contrast molecules using amino acids and peptides.

本文用5-氨基-2,4,6-三碘二苯二甲酸(ATIIPA)作为亲核试剂生成相应的1,3-二酯。两种类型的1,3-二酯,i)二乙基5-氨基-2,4,6-三碘二苯二甲酸酯(DEtTIIP)和ii)二乙酰氧乙基5-氨基-2,4,6-三碘二苯二甲酸酯(DAcOEtTIIP),大多是定量制备的。通过5-氨基的异氰化,测试了1,3-酯作为氨基氨基化剂对β α酯的氨基。DEtTIIP- nco与βAla- oet加成反应生成DEtTIIP:CO-βAla-OEt,由于相邻2,4,6-碘的空间屏蔽,1,3-二乙酯具有很强的抗碱性水解能力,而βAla亚结构的α-乙酯容易被去除。另一种加合物DAcOEtTIIP:CO-βAla-OtBu的碱性水解,只去除1,3-乙酰基乙基,形成产物DAcOHTIIP:CO-βAla-OtBu,而-OtBu酯的酸性裂变定量得到DAcOEtTIIP:CO-βAla。这些结果表明,DAcOEtTIIP是氨基酸酯氨基甲酰化的可行前体,保留了选择性酯去保护的自由,这进一步启发了利用氨基酸和肽设计对比分子。
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引用次数: 0
A Robust Nanocatalyst Incorporating Multi-Walled Carbon Nanotubes Infused with Magnetic Nanoparticles and Biguanide–Silver Nanoparticles for Multicomponent Synthesis of Benzopyrano-Pyrimidines 多壁碳纳米管注入磁性纳米粒子和双胍银纳米粒子用于多组分合成苯并吡喃-嘧啶。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-12 DOI: 10.1002/open.202500398
Anwer Ali Mueen, Suranjana V. Mayani, Suhas Ballal, Shaker Al-Hasnaawei, Abhayveer Singh, Kattela Chennakesavulu, Kamal Kant Joshi, Reza Mohammadi

A highly efficient and environmentally friendly synthetic method has been developed for the preparation of benzopyrano-pyrimidines using multi-walled carbon nanotubes/magnetic nanoparticles-Biguanide-Ag NPs as a heterogeneous nanocatalyst in choline chloride–urea (ChCl–Urea) deep eutectic solvent. This approach offers numerous advantages, including high isolated yields (86–99%) and short reaction times (10–70 min), along with broad substrate compatibility for both electron-donating and electron-withdrawing functional groups. The method exhibits excellent catalytic efficiency, with high turnover numbers and turnover frequencies, even at low catalyst loading. The use of ChCl–Urea as a green, biodegradable, and nonvolatile solvent aligns with sustainable chemistry principles and allows for easy solvent recovery. Additionally, the magnetic nanocatalyst is easily recoverable and reusable, maintaining activity over multiple cycles. Operational simplicity, mild conditions, and one-pot multi-component reaction design further enhance the method's scalability and synthetic utility. Given the biological relevance of benzopyrano-pyrimidines, this strategy presents a valuable platform for green synthesis in medicinal chemistry and pharmaceutical development.

在氯化胆碱-尿素(chcl -尿素)深度共熔溶剂中,以多壁碳纳米管/磁性纳米颗粒-双胍-银纳米粒子为非均相纳米催化剂,制备了一种高效环保的苯并吡喃嘧啶合成方法。该方法具有许多优点,包括高分离收率(86-99%)和短反应时间(10-70分钟),以及对供电子和吸电子官能团的广泛底物兼容性。该方法表现出优异的催化效率,即使在低催化剂负载下也具有较高的周转次数和周转频率。氯化脲作为一种绿色的、可生物降解的、不挥发的溶剂,符合可持续化学原理,并且易于溶剂回收。此外,磁性纳米催化剂易于回收和重复使用,在多个循环中保持活性。操作简单,条件温和,一锅多组分反应设计进一步提高了该方法的可扩展性和合成实用性。鉴于苯并吡喃嘧啶的生物学相关性,该策略为药物化学和药物开发中的绿色合成提供了一个有价值的平台。
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引用次数: 0
Metabolism of Epoxidised Withanolides by a Generalist and a Specialist Insect Species 一种多面手和一种特殊昆虫的环氧化Withanolides代谢。
IF 3.1 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2025-09-11 DOI: 10.1002/open.202500359
Marie Pauline Sell, Christian Paetz, Felix Feistel, David G. Heckel, Yannick Pauchet

Major secondary metabolites of Physalis plants, epoxidized withanolides, have a potent feeding deterrent and growth inhibitory effect on most herbivorous insects. Caterpillars of the specialist moth species Heliothis (Chloridea) subflexa consume only Physalis fruits, whereas the closely related generalist Heliothis (Chloridea) virescens feeds on 14 different plant families, but not Physalis. The two species have different physiological responses to dietary withanolides, so it is wondered whether they metabolize withanolides differently. The Physalis peruviana plants are grown in a [13C]CO2-supplied atmosphere, 4β-hydroxywithanolide E is isolated and purified from the leaves, and the compound is fed to the caterpillars. Subsequent high-performance liquid chromatography with diode array UV-vis detection coupled to high-resolution electrospray ionization mass spectrometry (HPLC-DAD-HRESIMS) and nuclear magnetic resonance (NMR) analyses of the main metabolite isolated from the frass show that both species convert 4β-hydroxywithanolide E mainly to withanolide S, probably by the action of an epoxide hydrolase. Withanolide S is completely characterized regarding its NMR and electronic circular dichroism data. To date, this is the first study to analyze the fate of withanolides after ingestion by insects.

Physalis植物的主要次生代谢产物是环氧化的withanolides,它对大多数食草昆虫具有有效的阻食和生长抑制作用。专精蛾种Heliothis (Chloridea) subflexa的幼虫只吃Physalis的果实,而密切相关的通才蛾Heliothis (Chloridea) virescens以14个不同的植物科为食,但不吃Physalis。这两种植物对饮食中的威马内酯有不同的生理反应,因此它们对威马内酯的代谢是否存在差异尚不清楚。在[13C] co2供应的环境中生长的紫绒Physalis peruviana植物,从叶子中分离和纯化了4β-hydroxywithanolide E,并将该化合物喂给毛虫。随后的高效液相色谱二极管阵列紫外可见检测,高分辨率电喷雾质谱(hplc - dad - hremms)和核磁共振(NMR)分析表明,从草中分离的主要代谢物,这两个物种主要转化4β-羟基戊内酯E为戊内酯S,可能是通过环氧化物水解酶的作用。通过核磁共振和电子圆二色性数据对其进行了完全表征。到目前为止,这是第一个分析被昆虫摄入后的命运的研究。
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