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eugenol
Food Bioscience · 2024 · IF 4.8

Effects of chitosan/eugenol-loaded IRMOF-3 nanoparticles composite films on reactive oxygen species metabolism and microbial community dynamics in postharvest strawberries

Yuyue Qin,Hongda Yu,Kejun Chen,Rui Cui,Jianxin Cao,Zhengxuan Wang,Zhi-Hong Zhang,Thanapop Soteyome

The market value of strawberries is considerably impacted by quality deterioration and senescence during postharvest storage. In the study, the effect of isoreticular metal-organic skeleton (IRMOF-3) nanoparticles loaded with eugenol/chitosan-based active packaging film on the metabolism of reactive oxygen species (ROS) and the change rule of the structure of the microbial community in strawberries inoculated with strawberries spoilage bacteria ( Botrytis cinerea ) during the storage period was investigated. The results demonstrated that composite film contribute to the sustenance of reduced hydrogen peroxide and superoxide anion concentrations and the suppression of malondialdehyde accumulation, in contrast to the control group. This investigation revealed that the composite film significantly bolstered the antioxidant enzyme activities and disease resistance-related enzyme activities of strawberries, encompassing polyphenol oxidase, peroxidase, superoxide dismutase (SOD), and catalase (CAT). Moreover, the transcription levels of SOD and CAT genes were notably elevated in strawberries packed within the composite films. Besides, the composite film had an inhibitory effect on pathogenic bacterial genera ( Ralstonia , Sphingomonas , and Erwinia ) and fungal genera ( Botrytis cinerea ) that cause strawberries spoilage and a delayed decline in bacterial genera (unidentified_ Chloroplast and Chryseobacterium ) and fungal genera ( Rhodotorula ) that are biocontrols of strawberries postharvest diseases. Therefore, this study provides novel perspectives on the mechanisms underlying the preservation of fruits and vegetables, focusing on alterations in ROS metabolism and microbiota composition during storage.

CAS / MDL: 7440-53-1
研究领域: 食品科学 · 植物病理学 · 分子生物学
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Polymer Chemistry · 2024 ·Vol. 15 ·期 48 ·4952-4961 · IF 4.1

Self-healable, reprocessable and anti-flammable eugenol-derived covalent adaptable thermosets based on dynamic covalent boronic esters and thiol–ene click chemistry

Haoxin Niu,Yu Li,Ping Zhang,Wenwen Guo,Xin Wang,Yuan Hu

Due to their excellent properties, thermosetting polymer materials have been widely used in many fields. Owing to the restriction of the crosslinked network, traditional thermosetting polymer materials exhibit insolubility and immiscibility. Therefore, the reprocessing of thermosetting polymer materials is a great challenge. With the depletion of petroleum-based resources, the utilization of natural resources for the preparation of bio-based thermosetting polymer materials is a major trend. In this study, eugenol-based covalent adaptable thermosets were prepared via UV curing and thermal curing according to thiol click chemistry. The mechanical properties of the eugenol-based covalent adaptable thermosets, which are better than those of the control sample, can be regulated according to the components. The eugenol-based covalent adaptable thermosets exhibited excellent transparency and UV shielding properties. The introduction of a dynamic covalent boronic ester (BSH) promoted the formation of residual char and enhanced the fire safety of the eugenol-based covalent adaptable thermosets. Owing to the dynamic borate ester bonds in the cross-linked network, the eugenol-based covalent adaptable thermosets exhibited significant stress relaxation behavior, and excellent shape memory function and self-healing properties. The samples were reprocessed at 100 °C several times. After three cycles of pulverizing and hot pressing, the recovery ratio of tensile strength of the reprocessed samples remained above 85%. This study provides a novel strategy for preparing self-healable, reprocessable and anti-flammable covalent adaptable thermosets with tunable mechanical properties.

研究领域: 材料科学 · 绿色化学
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2021 · IF 4.539

Novel fabrication of robust superhydrophobic polyester fabric with eugenol based on thiol-ene click chemistry for self-cleaning and water–oil separation

Ailing Xie,Xinpeng Chen,Xin Ai,Yahui Wang,Yirong Wang,Xiaowei Zhu,Tieling Xing,Guoqiang Chen

In this work, natural phenol eugenol and 1-octadecanethiol was adopted to fabricate superhydrophobic polyester (PET) fabric through click chemistry reaction. The surface of PET fabric was treated with eugenol to further chelate metal ions to increase the roughness. Then, under the UV irradiation and catalysis of photo initiator benzoin dimethyl ether (DMPA), 1-octadecanethiol was introduced to reduce the surface energy of fabric surface through the click chemistry reaction between the double bond in the molecular structure of eugenol and sulfhydryl group, thus the superhydrophobic PET fabric with water contact angle (WCA) of 163.8° and scrolling angle (SA) of 3.47° was prepared. XPS and FTIR results confirmed that Fe 2+ and -SH were successfully co-deposited on the surface of PET fabric through eugenol. The tests results showed that the modified PET fabric maintains stable mechanical properties . Its superhydrophobic property had good stability and durability in the harsh environment of simulated seawater immersion, UV irradiation, acid/alkali and organic reagents erosion. The superhydrophobic fabric also has good self-cleaning performance and oil-water separation performance after repeated use for 25 times and the separation efficiency was more than 95%, which has good application prospects in oily wastewater treatment and protective textiles.

研究领域: 材料科学 · 表面化学 · 纺织工程 · 环境科学
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RSC Advances · 2016 ·Vol. 6 ·期 22 ·17857-17866 · IF 3.289

Synthesis of eugenol-based multifunctional monomers via a thiol–ene reaction and preparation of UV curable resins together with soybean oil derivatives

Jinyue Dai,Yanhua Jiang,Xiaoqing Liu,Jinggang Wang,Jin Zhu

Two kinds of UV-curable monomers (EM2G and EM3G) were synthesized from eugenol via a thiol–ene reaction. Their chemical structures were confirmed by FT-IR, 1H-NMR and 13C-NMR before they were employed to copolymerize with acrylated epoxidized soybean oil (AESO). Bio-based UV curable resins were prepared and their thermal and mechanical properties were investigated by tensile testing and dynamic mechanical analysis (DMA). Their coating properties on tinplate were also studied. The results showed that the tensile strength, tensile modulus and glass transition temperatures of the cured AESO were significantly improved after the introduction of eugenol-based monomers. In addition, the UV-cured resins could be well coated on the surface of tinplate and good coating properties, such as hardness, flexibility, adhesion, solvent resistance and water absorption were demonstrated.

研究领域: 材料科学 · 有机化学 · 涂料技术
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2023 · IF 6

Characterization of chitosan/eugenol-loaded IRMOF-3 nanoparticles composite films with sustained antibacterial activity and their application in postharvest preservation of strawberries

Kejun Chen,Charles Brennan,Jianxin Cao,Guiguang Cheng,Lin Li,Yuyue Qin,Haiyan Chen

In this work, we prepared chitosan/eugenol-loaded IRMOF-3 nanoparticles (CS/IRMOF-3-EU) composite films using (0, 2, 4, and 6 wt%) isoreticular metal-organic framework (IRMOF-3) nanoparticles loaded with eugenol (IRMOF-3-EU), co-blended with chitosan to develop environmentally friendly food packaging materials with sustained antimicrobial activity. The microstructure and physicochemical properties of the composite films were investigated. The addition of IRMOF-3-EU to the CS matrix significantly enhanced the UV-blocking property and elongation at the break of the composite films; the CS/IRMOF-3-EU composite films inherited the antioxidant and antibacterial properties of eugenol (EU), and the DPPH radical scavenging ability was increased to 53.8% with the addition of 6% IRMOF-3-EU, while it showed excellent antibacterial ability; in addition, the CS/IRMOF-3-EU composite films achieved the sustainable release of eugenol to achieve the long-lasting antibacterial effect. Experiments on strawberry preservation applications showed that the CS/IRMOF-3-EU films slowed down the deterioration of strawberry quality, delayed the decline of hardness, effectively suppressed weight loss, H 2 O 2 content, and malondialdehyde content, and delayed the decline of catalase activity and peroxidase activity. It showed that the CS/IRMOF-3-EU composite films could be used to maintain the postharvest quality and prolong the shelf life of strawberries.

CAS / MDL: 97-53-0
研究领域: 食品科学 · 材料科学 · 植物病理学
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PHYTOPATHOLOGY · 2025 · IF 3.1

Eugenol Potentially Targets Oleate Delta-12 Desaturase of Botrytis cinerea and Controls Gray Mold as Part of a Combination of Multiple Fungicidal Components

Xiansu Wang,Chengyan Xia,Miss Dongxue Li,Miss Fenghua Liu,Jun Zhang,Miss Wenjing Xie,Dan Cheng,Libo Zhang,Zhuo Chen

Eugenol exhibits a broad spectrum of antimicrobial activities and fungicide efficacy against crop diseases. However, the antifungal mechanisms of eugenol remain incompletely understood. In this study, we assessed the inhibitory activity of eugenol against several phytopathogenic fungi, finding it to be particularly effective against Botrytis cinerea . The half-maximal effective concentration for inhibiting hyphal growth of B. cinerea was determined to be 72.11 µg/ml. Eugenol exhibited significant inhibition effect of 66.72 and 43.62% against gray mold on tomato fruit and leaves at the 1,500.0 µg/ml dose. Micromorphological analysis revealed that eugenol induced abnormalities in hyphal structures, including disrupted cell membranes and unclear organelle boundaries. Transcriptomic analysis indicated that differentially expressed genes in hyphae treated with eugenol were primarily enriched in processes related to lipid metabolism, transmembrane transport, and electron transfer activity. Molecular docking studies suggested that eugenol may bind to oleate delta-12 desaturase (FAD2) with a low free energy of −9.9 kcal/mol. Assays of cell membrane permeability and hyphal staining confirmed that eugenol disrupts the cell membrane, resulting in leakage of hyphal contents. Quantitative PCR assay showed that eugenol significantly altered the expression of genes involved in lipid metabolism. Compared to the wild type, fad2 mutant displayed slower hyphal growth rates and became less sensitive to the effects of eugenol. This study demonstrates that eugenol target FAD2, disrupt cell membrane integrity, thereby inhibiting the proliferation of B. cinerea . Several formulations of eugenol, including feneptamidoquin or meridianin C, exhibit stronger inhibitory effects, offering promising potential for the control of gray mold.

✓ 已验证 DOI PubMed 高影响因子
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Microbial Cell Factories · 2025 ·Vol. 24 ·期 1 ·1-12 · IF 4.9

Surface display of eugenol oxidase and dioxygenase complex as a sustainable biocatalyst for efficient bioconversion of lignin-derived 4-n-propylguaiacol to vanillin

Tian Yongqing,Yang Yige,Ni Minmin,Wo Jing

Background Vanillin is a widely utilized flavor compound of significant value in the food and pharmaceutical sectors, which can be obtained through natural extraction, chemical synthesis, or biotechnological processes. However, the yield from vanilla pods is insufficient to meet market demand, and chemically synthesized vanillin not only encounters limitations in its application within the food and pharmaceutical industries but also needs to address environmental concerns and unsustainable raw material sources. Hence, it is imperative to explore alternative approaches to develop an efficient and cost-effective green vanillin. To address the challenges encountered in vanillin biosynthesis, such as substrate uptake limitations and product-induced inhibition of cell growth,we leveraged the advantages of surface display technology and artificial multi-enzyme scaffolds to construct a hybrid surface-display biocatalytic system by assembling Eugenol oxidase (EUGO) and dioxygenase (NOV1), which can convert lignin biowaste 4- n -propylguaiacol (4-PG) into vanillin on the surface of Escherichia coli BL21(DE3). Results To assemble bioactive macromolecules of EUGO and NOV1 on the surface of E. coli BL21(DE3), we utilized Lpp-OmpA-SpyCatcher (LOAS) as an anchoring motif and displayed EUGO-linker-NOV1-SpyTag (ELNS) by covalent interaction between SpyTag andSpyCatcher to allow their spatial proximity. After optimization of the reaction system, our self-assembly display system exhibited highly efficiency in converting 4-PG into vanillin and reached a final concentration of vanillin at 12.58 g/L, 2.5 times higher than that achieved by thewhole-cell biocatalytic system. The LOAS-ELNS display system was applied to the sustainable biosynthesis of vanillin from lignin-derived 4-n-propylguaiacol at least 10 times. Conclusions This work provided a generalized approach to co-expressing proteins and offered an efficient, eco-friendly, and renewable method for the biosynthesis of vanillin from 4-PG.

研究领域: 生物化学 · 合成生物学 · 环境科学
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JOURNAL OF NANOBIOTECHNOLOGY · 2025 ·Vol. 23 ·期 1 ·1-17 · IF 12.6

Multi-stimuli-responsive pectin-coated dendritic mesoporous silica nanoparticles with Eugenol as a sustained release nanocarrier for the control of tomato bacterial wilt

Guo Xueping,Li Huiyan,Li Zhihao,Cui Ziqi,Ma Guangming,Nassor Aisha Khalfan,Guan Yi,Pan Xiaohong

Background Environmentally responsive nanoscale biocide delivery system enhances smart, regulated, and synergistic biocide application with precise biocide release. In this study, pectin-modified dendritic mesoporous silica nanoparticles (DMSNs) was used as a carrier to successfully construct a microenvironment-responsive (pH, temperature and enzyme) eugenol nano-biocide delivery system for the control of Ralstonia solanacearum infection. Results The results showed that the specific surface area, pore size and surface activity of DMSNs significantly influence the biocide loading of eugenol, and the biocide loading capability was up to 72.50%. Eu@DMSNs/Pec had significant pH and pectinase stimulating effects, with varying release amounts under different temperature conditions. Compared with eugenol alone, Eu@DMSNs/Pec significantly enhanced the efficacy of eugenol. DMSNs assisted eugenol to induce peroxidation damage, produce ROS (•O 2 − , •OH and 1 O 2 ), achieve synergistic antibacterial effects, and had better rain erosion resistance and foliar retention rate based on pectin wettability and adhesion. Eu@DMSNs/Pec-FITC showed demonstrated efficient transport characteristics in tomato roots, stems and leaves, which enhanced the control effect on tomato bacterial wilt. In addition, Eu@DMSNs/Pec exert minimal influence on tomato seed germination and root growth, and have low toxicity to non-target organisms such as earthworms. Therefore, Eu@DMSNs/Pec environment-responsive nano-controlled release nanocarrier can effectively achieve accurate biocide release and reduce biocide dosage. Conclusion This work not only provides a pectin-modified DMSNs-based eugenol nanoscale biocide delivery system in response to specific environmental conditions of R. solanacearum infection but also elucidates the eugenol biocide loading, selective release ability and antibacterial mechanism of the system.

CAS / MDL: 6066-82-6
研究领域: 植物病理学 · 纳米生物学 · 环境科学
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Coatings · 2021 ·Vol. 11 ·期 2 ·147 · IF 2.881

An Active Gelatin Coating Containing Eugenol and Vacuum Delays the Decay of Chinese Seabass (Lateolabrax maculatus) Fillets during Cold Storage: A Microbiome Perspective

Xuan Ma,Qianqian Zhou,Weiqiang Qiu,Jun Mei,Jing Xie

The purpose of this study was to evaluate the effect of an active gelatin coating containing eugenol and vacuum on the microbial diversity of Chinese seabass (Lateolabrax maculatus) during cold (−0.9 °C) storage. The bacterial sequences in Chinese seabass were observed using a high-throughput sequencing technique targeting the V3–V4 region of the 16S Ribosomal DNA (rDNA) on 0, 12th, and 24th day, which showed a more comprehensive estimate of the microbial diversity in seabass samples compared with microbial enumeration. The results revealed that the species diversity of fresh seabass was rich, mainly includingCarnobacterium,Glutamicibacter, andPseudomonas, with abundance ratios of 0.286, 0.160, and 0.130, respectively.PseudomonasandShewanellawere the primary contaminants in the spoiled control samples, where the abundance ratios increased from 0.220 and 0.174 on the 12th day to 0.802 and 0.163 on the 24th day, respectively. Vacuum treatment could inhibit the growth ofPseudomonasandShewanellasuch that when stored on the 12th day,Brochothrixbecame the superior genus. However,PseudomonasandShewanelladominated the storage until the 24th day, where their abundance ratios were 0.343 and 0.279, respectively. The inhibition ofPseudomonasandCarnobacteriumwas gradually enhanced with increasing concentrations of eugenol. Furthermore, an active gelatin coating containing eugenol and vacuum treatment was more effective at inhibiting the increase of the total volatile basic nitrogen. This study confirmed that an active gelatin coating containing eugenol and vacuum could reduce the species of bacteria, inhibit the growth and reproduction of the main dominant spoilage bacteria, and delay the spoilage of seabass.Keywords:coating preservation;high-throughput sequencing;shelf life;diversity

CAS / MDL: 97-53-0
研究领域: 食品科学 · 微生物学 · 生物技术
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Food Chemistry-X · 2022 · IF 6.443

Eugenol treatment delays the flesh browning of fresh-cut water chestnut (Eleocharis tuberosa) through regulating the metabolisms of phenolics and reactive oxygen species

Lijuan Zhu,Wanfeng Hu,Ayesha Murtaza,Aamir Iqbal,Jiaxing Li,Jiao Zhang,Junjie Li,Mengjie Kong,Xiaoyun Xu,Siyi Pan

The potential mechanism behind the browning inhibition in fresh-cut water chestnuts (FWC) after eugenol (EUG) treatment was investigated by comparing the difference in browning behavior between surface and inner tissues. EUG treatment was found to inactivate browning-related enzymes and reduce phenolic contents in surface tissue. Molecular docking further confirmed the hydrophobic interactions and hydrogen bonding between EUG and phenylalanine ammonia-lyase (PAL). Moreover, EUG also enhanced reactive oxygen species (ROS)-scavenging enzyme activities, ultimately decreasing the O 2 - generation rates. Regarding inner tissue, EUG induced the accumulation of colorless phenolic compounds and increased the antioxidant capacity. In conclusion, 1.5 % EUG exhibited the best inhibitory effect on FWC browning, which partly attribute to the direct inhibitory effects on PAL activity. Furthermore, EUG could also enhance the enzymatic/non-enzymatic antioxidant capacity and alleviate the ROS damage to membranes, thereby, preventing the contact between oxidative enzymes and phenols and indirectly inhibiting the enzymatic browning in FWC.

CAS / MDL: 97-53-0
研究领域: 食品科学 · 植物生理学
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Food and Bioprocess Technology · 2022 ·Vol. 15 ·期 8 ·1821-1835 · IF 5.581

Scavenging of ROS After Eugenol Treatment as Mechanism of Slowing Down Membrane Lipid Metabolism to Maintain the Surface Color of Fresh-Cut Yam

Bai Tingting,Li Jiaxing,Murtaza Ayesha,Iqbal Aamir,Zhu Lijuan,Zhang Jiao,Zhang Bing,Xu Xiaoyu,Pan Siyi,Hu Wanfeng

The effects of eugenol emulsion (EUG) on the browning of fresh-cut yam during storage and its inhibition mechanism were studied. The EUG treatment group had a significant anti-browning ability, and the 1.5% EUG treatment group had the best effect. During the whole storage period, the activities of peroxidase (POD) and phenylalanine ammonia-lyase (PAL) decreased significantly after 1.5% EUG treatment, especially on day 4, when the activity of POD and PAL was 3.2% and 23% of that of the control group, respectively. Molecular docking experiments showed that EUG inhibited PAL activity by binding to the active center of PAL, a key browning enzyme. A decrease in total phenol content was also observed. In addition, after EUG treatment, catalase (CAT) activity was significantly increased, preventing the accumulation of reactive oxygen species (ROS)-H 2 O 2 . EUG inhibited membrane lipid metabolism, 1.5% EUG delayed the emergence of lipoxygenase activity peak, and malondialdehyde (MDA) content decreased by 75.67% compared with the control on 4 d. In comparison with control, EUG increased the scavenging capacity of DPPH, ABTS, and iron-reducing antioxidant capacity (FRAP). The mechanism may be that EUG enhances antioxidant capacity, thereby reducing ROS-induced membrane lipid metabolism, therefore, lowering the synthesis and oxidation of phenolic compounds, and ultimately inhibiting browning.

CAS / MDL: 97-53-0
研究领域: 食品科学 · 植物生理学 · 采后技术
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Food Additives and Contaminants Part A-Chemistry Analysis Control Exposure & Risk Assessment · 2022 · IF 3.549

Hydrophobic deep eutectic solvent-based ultrasonic-assisted liquid-liquid microextraction combined with GC for eugenol, isoeugenol, and methyl isoeugenol determination in aquatic products

Jiaze Yan,Shaomin Ma,Mingrui Feng,Jiqi Zheng,Ming Guo

The use of deep eutectic solvents (DESs) has great prospects because of the green and efficient characteristics, which can be used for developing analytical methods for foods. In this research, assisted by ultrasonic waves, a liquid-liquid microextraction detection method combined with gas chromatography was established for three anaesthetics (eugenol, isoeugenol, and methyl isoeugenol) in aquatic food. The processing conditions including the components, ratio of hydrogen bond acceptor and hydrogen bond donor, DES volume, ultrasonic time, and pH were evaluated and optimised to improve the extraction efficiency, which was based on the DES structures and properties. In-house method validation was carried out by applying to real samples. A Thymol: levulinic acid DES (with a molar ratio of 1:2) was used as the extractant and the recoveries were as high as 93–101% for eugenol, 90–100% for methyl isoeugenol, and 86–94% for isoeugenol with RSDs <5% under optimum conditions. The limit of detection and quantification of the eugenol compounds were 0.08–0.10 μg/mL and 0.26–0.33 μg/mL, respectively. The method has green credentials and comparable LOD to homologous apparatus, which can be used for the determination of eugenol components in aquatic food.

研究领域: 食品科学 · 分析化学
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