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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Synthesis of Quaternary Ammonium Derivatives of Eugenol and Their Antifungal Mechanism against Gloeophyllum trabeum Wood-Decaying Fungi

Li Zhang,Xiaolin Lei,Zhaoying Wang,Zebo Liu,Jiguang Chen,Yuanyuan Zhang,Bing Cao,Yuxin Fu,Zhongping Yin,Dayong Peng,Fanxin Zeng

To discover novel preservatives for treating wood-decaying fungi, 48 novel eugenol quaternary ammonium salt derivatives were designed and synthesized. Among them, compounds 3j, 3k, 4j, 4k, 5j, 5k, and 6j showed remarkable antifungal activity against Gloeophyllum trabeum (G. trabeum), affording EC50 values ranging from 2.11–7.50 μg/mL. Notably, 3j demonstrated the most potent activity against G. trabeum (EC50 = 0.14 μg/mL), surpassing the positive control dodecyldimethylbenzylammonium chloride (DDBAC, EC50 = 3.33 μg/mL). Additionally, 3j significantly reduced wood mass loss and decay caused by G. trabeum. Mechanistic studies revealed that 3j disrupted the fungal ultrastructure, increased membrane permeability, and induced cellular leakage. Furthermore, 3j disrupted the antioxidant system and energy metabolism, resulting in the accumulation of reactive oxygen species. The multiomics data revealed the molecular mechanisms by which 3j regulated G. trabeum, including key genes, proteins, metabolites, and pathways. This study elucidates key mechanistic insights into developing a natural-product-derived wood preservative.

CAS / MDL: 2206-27-1 865-49-6
研究领域: 天然产物化学 · 林业微生物学 · 抗真菌药理学 · 分子真菌学 · 木材保护学 · 代谢组学 · 化学生物学
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FOOD CONTROL · 2024 · IF 5.6

UV−Curable antibacterial and pH−sensitive eugenol functionalized chitosan−polyurethane hydrogels for shelf−life extension of chicken

Xiaojia Wang,Jizhong Yuan,Nana Sun,Yaohuang Jiang,Yanchun Yu,Guoqiao Lai,Xiongfa Yang

Antibacterial and pH−sensitive eugenol functionalized chitosan−polyurethane hydrogels (UV−EBs) for shelf−life extension of chicken were prepared from thiol−modified chitosan (CS) and UV−curable polyurethanes grafted with eugenol and bromocresol green by UV−curable method. The antibacterial efficiency of UV−EBs is about 55% and 86% respectively after 8 h co−cultured against S. aureus and E. coli . Therefore, a contact−kill mechanism was proposed. Despite the toxicity of UV−EBs against L929 cells increased with the increment of the amount of eugenol groups, the UV−EBs prepared still have potential application in food packing and coatings. Shelf−life extension study for chicken breast demonstrated the UV−EBs can be utilized for packaging materials to extend the shelf−life of high−quality protein food such as chicken breast. The thermal stability of UV−EBs is better than eugenol because the initiate decomposition temperature ( T d5 ) of the former is in the range of 154–175 °C while that of the latter is about 134 °C. Therefore, UV−EBs have potential application in package some food that still has a high residual temperature after being cooked or heated. The UV−EBs demonstrate superior mechanical performance with tensile strength in the range of 0.77–4.90 MPa and the elongation at break in the range of 135–196%, respectively. The UV−EBs also show naked eyes visible color variation from yellow to green and finally to be Prussian blue when the pH values varied from 2 to 14. This work supplied a feasible method to develop antibacterial hydrogels for packaging materials to extend the shelf−life of high−quality protein food.

CAS / MDL: 77-99-6
研究领域: 材料科学 · 食品科学 · 生物技术 · 化学
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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Dissolving Hyaluronic Acid-Based Microneedles to Transdermally Deliver Eugenol Combined with Photothermal Therapy for Acne Vulgaris Treatment

Qi Wang,Zhiyang Gan,Xinxin Wang,Xinying Li,Lei Zhao,Derong Li,Zhilang Xu,Changdao Mu,Liming Ge,Defu Li

A microneedle transdermal drug delivery system simultaneously avoids systemic toxicity of oral administration and low efficiency of traditional transdermal administration, which is of great significance for acne vulgaris therapy. Herein, eugenol-loaded hyaluronic acid-based dissolving microneedles (E@P-EO-HA MNs) with antibacterial and anti-inflammatory activities are developed for acne vulgaris therapy via eugenol transdermal delivery integrated with photothermal therapy. E@P-EO-HA MNs are pyramid-shaped with a sharp tip and a hollow cavity structure, which possess sufficient mechanical strength to penetrate the stratum corneum of the skin and achieve transdermal delivery, in addition to excellent in vivo biocompatibility. Significantly, E@P-EO-HA MNs show effective photothermal therapy to destroy sebaceous glands and achieve antibacterial activity against deep-seated Propionibacterium acnes (P. acnes) under near-infrared-light irradiation. Moreover, cavity-loaded eugenol is released from rapidly dissolved microneedle bodies to play a sustained antibacterial and anti-inflammatory therapy on the P. acnes infectious wound. E@P-EO-HA MNs based on a synergistic therapeutic strategy combining photothermal therapy and eugenol transdermal administration can significantly alleviate inflammatory response and ultimately facilitate the repair of acne vulgaris. Overall, E@P-EO-HA MNs are expected to be clinically applied as a functional minimally invasive transdermal delivery strategy for superficial skin diseases therapy in skin tissue engineering.

研究领域: 药学 · 皮肤科 · 纳米技术 · 治疗工程 · 生物医学工程
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CHEMICAL ENGINEERING JOURNAL · 2025 · IF 13.2

Design evolution towards sustainability: From dual furan and eugenol biomass to functional epoxy resin and its upgrading

Jingjing Meng,Zhiyong Li,Xinru Bai,Xinyi Gao,Yuting Dong,Lei Sheng,Jie Sun,Kai Guo

Biobased epoxy resins have made great strides in recent years to replace their petroleum-based counterparts, particularly for the diglycidyl ether of bisphenol A (DGEBA) resins. Due to their increased sustainability and performance enhancement, bio-epoxy resins meet a multitude of requirements. Herein, a facile route was developed in high yield for the dual biomass monomer DEF from 5-hydroxymethylfurfural and eugenol, which exhibited much lower viscosity than the DGEBA counterpart (0.506 < 10.7 Pa s), thus beneficial for the solvent-free composites and prepreg procedures. The thermosets behaved with excellent mechanical properties and thermal performances. Compared with the DGEBA counterpart, remarkedly, the solvolysis proceeded in N, N-dimethylformamide at ambient conditions and permitted the full breakdown of the biobased matrices. Such merit significantly led to the ready recycling of fillers from their composites rather than being landfilled or incinerated till their end-of-life cycle. Moreover, thermal deformation and shape memory performances are not only fit for the pristine epoxy resins but suitable for the carbon fiber reinforced composites (CFRC) at about 120 ℃, thus allowing their performance upgrade. Therefore, these advantages of renewable thermosets possibly provide a facile and scalable route to access high-value integrated biobased epoxy networks in the industry.

研究领域: 材料科学 · 化学工程 · 可持续发展
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Active cellulose acetate/purple sweet potato anthocyanins@cyclodextrin metal-organic framework/eugenol colorimetric film for pork preservation

Huaiting Pang,Yimin Wu,Qianlan Tao,Yewen Xiao,Wei Ji,Linlin Li,Hualin Wang

As a natural pH-sensing colorant, purple sweet potato anthocyanins (PSPAs) have demonstrated great potential in colorimetric film for freshness monitoring. However, the photothermal instability of PSPAs is still a challengeable issue. Herein, γ-cyclodextrin metal-organic framework (CD-MOF) loaded with PSPAs (PSPAs@CD-MOF, i.e., PM) and eugenol (EUG) were incorporated in cellulose acetate (CA) matrix for developing a smart active colorimetric film of CA/PM/EUG, where PM and EUG were hydrogen-bonded with CA. Attentions were focused on the photothermal colorimetric stability, colorimetric response, and antibacterial activity of the films. The presence of PM and EUG endowed the film outstanding UV-blocking performance and enhanced the barrier against water vapor and oxygen. Target film of CA/PM15/EUG10 had good photothermal colorimetric stability due to the protection of CD-MOF on PSPAs and the color changes with pH-stimuli were sensitive and reversible. In addition to antioxidant activity, CA/PM15/EUG10 had antibacterial activity against Escherichia coli and Staphylococcus aureus . The application trial results indicated that the CA/PM15/EUG10 was valid to indicate pork freshness and extended the shelf-life by 100 % at 25 °C, which has demonstrated a good perspective on smart active packaging for freshness monitoring and shelf-life extension.

研究领域: 食品科学 · 材料科学
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PROGRESS IN ORGANIC COATINGS · 2025 · IF 7.3

Sustainably sourced covalent adaptable networks derived from eugenol for flame retardant, transparent and self-healing coating applications

Yu Li,Hao-Xin Niu,Ze-Tao Xiao,Tian-Mo Yang,Hao-Ran Jiang,Wei Wang,Yuan Hu,Xin Wang

High-transparent polycarbonate (PC) is often used to replace glass in construction, but its poor flame retardancy limits its use. In recent years, materials for covalent adaptive networks (CANs) have gained much attention. The preparation of CANs and their application to flame retardant coatings is an innovative approach. In this work, a dithiol-containing borate ester (B2SH) and P-containing eugenol monomer (TEP) were synthesized. The flame retardant self-healing eugenol bio-based covalent adaptive network (TEP-SH) was prepared by copolymerizing TEP with B2SH and polythiol monomers (such as pentaerythritol tetra(3-mercaptopropionate) (4SH)) via photo-induced thiol-ene polymerization. Among these samples, TEP/B2SH/13%4SH has the best comprehensive performance, while superior flame retardancy, self-healing and shape memory properties and high transparency are preserved. TEP/B2SH/13%4SH was coated on a PC board for the cone calorimeter test. Compared with those of PC, PHRR and THR decreased by 31.3% and 24.5%, respectively, and the char yield (CY) increased from 3.5% to 16.6%. Moreover, TEP/B2SH/13%4SH exhibited excellent adhesion to PC with a high shear strength (2.77 MPa). Therefore, TEP/B2SH/13%4SH has excellent performance and can be used as a flame-retardant, transparent and self-healing coating, thus ensuring the safe application of PC in building materials.

研究领域: 材料科学 · 化学工程
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2024 ·Vol. 25 ·期 4 ·2141 · IF 4.9

Multi-Omics Approaches for Liver Reveal the Thromboprophylaxis Mechanism of Aspirin Eugenol Ester in Rat Thrombosis Model

Qi Tao,Ning Ma,Liping Fan,Wenbo Ge,Zhendong Zhang,Xiwang Liu,Jianyong Li,Yajun Yang

Aspirin eugenol ester (AEE) is a novel medicinal compound synthesized by esterifying aspirin with eugenol using the pro-drug principle. Pharmacological and pharmacodynamic experiments showed that AEE had excellent thromboprophylaxis and inhibition of platelet aggregation. This study aimed to investigate the effect of AEE on the liver of thrombosed rats to reveal its mechanism of thromboprophylaxis. Therefore, a multi-omics approach was used to analyze the liver. Transcriptome results showed 132 differentially expressed genes (DEGs) in the AEE group compared to the model group. Proteome results showed that 159 differentially expressed proteins (DEPs) were identified in the AEE group compared to the model group. Six proteins including fibrinogen alpha chain (Fga), fibrinogen gamma chain (Fgg), fibrinogen beta chain (Fgb), orosomucoid 1 (Orm1), hemopexin (Hpx), and kininogen-2 (Kng2) were selected for parallel reaction monitoring (PRM) analysis. The results showed that the expression of all six proteins was upregulated in the model group compared with the control group. In turn, AEE reversed the upregulation trend of these proteins to some degree. Metabolome results showed that 17 metabolites were upregulated and 38 were downregulated in the model group compared to the control group. AEE could reverse the expression of these metabolites to some degree and make them back to normal levels. The metabolites were mainly involved in metabolic pathways, including linoleic acid metabolism, arachidonic acid metabolism, and the tricarboxylic acid (TCA) cycle. Comprehensive analyses showed that AEE could prevent thrombosis by inhibiting platelet activation, decreasing inflammation, and regulating amino acid and energy metabolism. In conclusion, AEE can have a positive effect on thrombosis-related diseases.

CAS / MDL: 50-78-2 97-53-0
研究领域: 药理学 · 生物信息学
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MOLECULES · 2026 ·Vol. 31 ·期 4 ·669 · IF 5.1

Intelligent Food Packaging Films Based on pH-Responsive Eugenol@ZIF-8/PVA-HACC with Enhanced Antimicrobial Activity

Jiarui Liu,Jiachang Feng,Zhefeng Xu,Jinsong Zhang,He Wang

Natural antibacterial food packaging materials endowed with environmental responsiveness are garnering substantial research interest in sustainable food preservation. This study reports the development of a pH-responsive antimicrobial composite film through encapsulation of eugenol—a natural phenolic compound—within zeolitic imidazolate framework-8 (ZIF-8). The engineered eugenol@ZIF-8 system demonstrated pH-dependent release characteristics, with cumulative release reaching 32.2% at pH 6 versus merely 0.61% at pH 7 over 4 h. Subsequent integration of this nanocarrier into a polyvinyl alcohol (PVA)/hydroxypropyltrimethyl ammonium chloride chitosan (HACC) matrix yielded a multifunctional composite film for active food packaging applications. The characterization of film revealed that while eugenol@ZIF-8 incorporation slightly compromised mechanical strength (tensile resistance decreased by 18.7%) and flexibility (elongation at break reduced to 54.3% of control), it significantly enhanced hydrophobicity (water contact angle increased to 92.5°) and thermal stability (decomposition temperature elevated by 34 °C). The composite film demonstrated synergistic antibacterial efficacy through the combined action of Zn2+ions, ZIF-8 nanostructures, and eugenol, achieving 88% inhibition againstE. coli.Practical validation through fresh noodle preservation trials confirmed the material’s effectiveness, with the optimized formulation (PVA-HACC-2% eugenol@ZIF-8, PHEZ2) extending shelf life by >5 days compared to conventional packaging. This work establishes a novel strategy for engineering intelligent ZIF-based packaging systems that respond to food spoilage microenvironments, offering significant potential for reducing food loss.

CAS / MDL: 97-53-0
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Insects · 2022 ·Vol. 13 ·期 11 ·1004 · IF 3.139

Monitoring the Methyl Eugenol Response and Non-Responsiveness Mechanisms in Oriental Fruit Fly Bactrocera dorsalis in China

Yinjun Fan,Changzhen Zhang,Yu Qin,Xinhui Yin,Xinyi Dong,Nicolas Desneux,Hongxu Zhou

Simple SummaryBactrocera dorsalisis a highly invasive polyphagous pest of fruit and vegetable, causing severe economic loss and trade restrictions by ovipositing inside hosts. Cryptic feeding habits of larval stages, strong flight ability of adults and prevalence of insecticide resistance reduce the efficiency of chemical control. Currently, the most cost-effective tool is olfaction-based trapping. Methyl eugenol (ME), a naturally occurring compound in some plants, alone or combination with insecticides has been widely used as a male attractant to monitor and controlB. dorsalispopulations for seven decades. Intense ME selection under laboratory conditions has resulted in the evolution of non- responsiveness inB. dorsalisand field management strategies based on ME has failed to eradicate recolonization ofB. dorsalisin some islands. However, the levels of ME responsiveness inB. dorsalisfield populations in China is unknown. In this study, we found that field populations had lower ME sensitivity compared to the susceptible strain. Furthermore, the results of olfactory organs, gene expressions and the bioassays showed that odorant binding protein (BdorOBP2, BdorOBP83b) and P450 may be involved in the lower sensitivity. The findings will guide the use of lures combined with insecticides and help to exploit molecular targets for the development of new attractants.AbstractBactrocera dorsalisis a notorious polyphagous pest in China, and its management strategies largely depend on methyl eugenol (ME), which has been widely used as an attractant to monitor and eradicateB. dorsalispopulations for seven decades. However, the non-responsiveness levels in fieldB. dorsalispopulations to ME is unknown. In this study, we monitored the response to ME in field populations from the four most heavily infested provinces in China, and the results showed that the populations had lower sensitivity to ME relative to GZS susceptible strain. The percent responsiveness of the lowest sensitivity population was 5.88-, 3.47-, and 1.47-fold lower relative to the susceptible strain at doses of 1, 10, and 100 µL of ME, respectively. Gene expression analysis and inhibitor assays further revealed that odorant binding protein (BdorOBP2, BdorOBP83b) and the P450 enzyme system may be associated with the lower response to ME. To our knowledge, this work is the first to report that the P450 enzyme system confers a lower responsiveness to lure insects. These findings provided valuable insights for exploiting ME non-responsiveness to protect sterile males from ME-based control strategies and the use of lures combined with insecticides.Keywords:methyl eugenol;non-responsiveness;odorant binding protein;P450;trapping

研究领域: 昆虫学 · 分子生物学 · 农业科学
✓ 已验证 DOI PubMed 高影响因子
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Microorganisms · 2021 ·Vol. 9 ·期 5 ·969 · IF 4.128

Limonin Enhances the Antifungal Activity of Eugenol Nanoemulsion against Penicillium Italicum In Vitro and In Vivo Tests

Yi Li,Runan Zhao,Yan Li,Zhiqin Zhou

Penicillium italicum, the cause of citrus blue mold, is a pathogenic fungus that seriously affects the postharvest quality of citrus fruit and causes serious economic loss. In this study, a eugenol nanoemulsion containing limonin, an antimicrobial component from citrus seeds, was prepared using a high-pressure microfluidizer and the antifungal activity of the nanoemulsions againstP. italicumwas evaluated based on the conidial germination rate, mycelial growth, and scanning electron microscopy analysis. The results showed that the minimum inhibitory concentration and the inhibition rate of limonin-loaded eugenol nanoemulsion was 160 μg/mL and 59.21%, respectively, which was more potent than that of the limonin-free eugenol emulsion. After treatment with the nanoemulsions, the integrity of theP. italicumcell membrane was disrupted, the cell morphology was abnormal, and the leakage of nucleic acid and protein was observed. In addition, the challenge test on citrus fruits revealed that the limonin-loaded eugenol emulsion inhibited citrus infection for longer periods, with an infection rate of 29.2% after 5 days. The current research shows that nanoemulsions containing limonin and eugenol have effective antifungal activity againstP. italicum, and may be used as a substitute for inhibiting blue mold in citrus fruits.Keywords:eugenol nanoemulsion;citrus blue mold;limonin;Penicillium Italicum;antifungal activity

CAS / MDL: 97-53-0
研究领域: 植物病理学 · 食品科学
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Scientific Reports · 2020 ·Vol. 10 ·期 1 ·1-12 · IF 3.998

Synthesis of mesoporous silica post-loaded by methyl eugenol as an environment-friendly slow-release bio pesticide

Chen Huayao,Chen Lishen,Shen Zhichuan,Zhou Hongjun,Hao Li,Xu Hua,Zhou Xinhua

Salicylaldimine, furfuralimine and benzaldehyde imine were adopted to modify mesoporous silica (MCM) respectively denoted as Sal-MCM, Fur-MCM and Ben-MCM before loading methyl eugenol (Me) for pesticide delivery. Me was adsorbed by Schiff base mesoporous silica without destructing regular hexagonal pore structure verified by the characterization results. DSC result implied that Me in amorphous state which was distributed in the pores of the mesoporous silica. The loading content of Me-Sal-MCM, Me-Fur-MCM and Me-Ben-MCM 67.89%, 73.34% and 73.84% which was higher than Me-MCM without modification (67.35%).Because the electrostatic interaction and π-π interaction between Schiff base and Me strengthened the adsorption capacity of the carrier. And the electrostatic interaction played a more important role in interaction between Me and Schiff base modified mesoporous silica. As a result, Schiff base modified sustained release system also has significantly longer sustained release time with a sequence of Me-Sal-MCM > Me-Ben-MCM > Me-Fur-MCM in release speed in negative correlation with the electric potential sequence. The behaviors of their sustained release performance can be fitted by First order kinetic model before Schiff base modification. After modification, their sustained release behaviors were consistent with Korsmeyer-Peppas equation with non-Fickian diffusion mechanism indicating that main impact on the release process after modification was no longer mainly controlled by the difference of the concentration. Finally, the highest lure rate of the modified MCM (Me-Fur-MCM) equals to the 73% of the pure Me due to its highest BET surface area and strongest interaction with Me among the three Schiff base modified samples. Therefore, the environment-friendly slow-release bio pesticide with long service life was prepared to reduce the damage on the environment caused by pesticide.

研究领域: 材料科学 · 化学 · 环境科学 · 农业科学
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JOURNAL OF SOLID STATE CHEMISTRY · 2019 · IF 2.291

Effect of organic template removal approaches on physiochemical characterization of Ni/Al-SBA-15 and eugenol hydrodeoxygenation

Xiangping Li,Han Yin,Jianguang Zhang,Juping Liu,Guanyi Chen

Template removing approaches can significantly impact the physiochemical properties of mesoporous molecular sieve materials. In order to better understand the relationship between template removing approaches and the properties of Ni/Al-SBA-15, four kinds of template removing approaches were introduced to remove the organic template from Al-SBA-15, respectively. The structural characteristics of these materials were analyzed by transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray fluorescence (XRF), powder X-ray diffraction (XRD), N 2 -sorption, Fourier transform infrared spectra (FT-IR), infrared spectra of pyridine adsorption (Py-FTIR), magic angle spinning-nuclear magnetic resonance (MAS-NMR), X-ray photoelectron spectroscopy (XPS) and gas chromatography-mass spectrometry (GC-MS). Ni/Al-SBA-15 of which the organic template was removed by two-step calcination method had the maximum specific surface area (619 ​m 2 /g). In contrast, Ni/Al-SBA-15 of which the organic template was removed using solvent extraction approaches had the lowest specific surface area (555 ​m 2 /g). The mesopore diameter of Ni/Al-SBA-15, using electric heating digestion method to remove the template, was significantly increased and the wall thickness was significantly decreased to 11.62 ​nm in comparison with the other samples. The selectivity of products during the process of eugenol hydrodeoxygenation was investigated. High hydrocarbons were obtained during catalytic hydrodeoxygenation over Ni/Al-SBA-15 of which the organic template was removed by using solvent extraction approaches. Compared with direct calcination process, two-step calcination was more effective in removing template and the corresponding catalyst was much more suitable for the hydrodeoxygenation process.

研究领域: 材料科学 · 催化化学
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