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MICROCHIMICA ACTA · 2021 ·Vol. 188 ·期 7 ·1-14 · IF 5.833

Platinum nanoparticles-embedded raspberry-liked SiO2 for the simultaneous electrochemical determination of eugenol and methyleugenol

Shi Zhaoxia,Xia Ling,Li Gongke,Hu Yufei

Based on platinum nanoparticle–embedded raspberry-liked SiO 2 , a sensitive and selective electrochemical sensor was developed for simultaneous determination of eugenol (EU) and methyleugenol (MEU). Raspberry-liked SiO 2 (RL-SiO 2 ) was characterized with open pores on the surface, which can be used as a path for utilizing the inner space fully. So, platinum nanoparticles (Pt NPs) could be embedded in the inner and outer surface of RL-SiO 2 . As a carrier, RL-SiO 2 not only avoided the agglomeration of the Pt NPs but also improved the catalytic performance. Therefore, the prepared Pt NPs@RL-SiO 2 /GCE exhibited excellent electrocatalytic activity for simultaneous determination of EU and MEU; the linearity ranges were 0.50 ~ 60 μmol/L for EU at a working potential of 0.65 V (vs. saturated calomel electrode) and 0.50 ~ 50 μmol/L for MEU at a working potential of 1.10 V; the detection limits were 0.12 μmol/L and 0.16 μmol/L ( S/N =3); and the relative standard deviations (RSDs) were 3.2% and 4.5%, respectively. In addition, Pt NPs@RL-SiO 2 /GCE was successfully applied to the analysis of fish samples; the obtained recoveries were between 92.0 and 107%. Notably, the results conducted on samples were highly consistent with those obtained from high-performance liquid chromatography. It can be concluded that the study provided a simple method for simultaneous electrochemical determination of EU and MEU in fish samples. Graphical abstract Schematic illustration of the preparation of RL-SiO2@Pt NPs/GCE for simultaneous determination of eugenol and methyleugenol in fish samples.

研究领域: 分析化学 · 纳米技术 · 电化学 · 食品科学
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Oxidative Medicine and Cellular Longevity · 2021 · IF 6.543

Protective Activity of Aspirin Eugenol Ester on Paraquat-Induced Cell Damage in SH-SY5Y Cells

Zhen-Dong Zhang,Ya-Jun Yang,Zhe Qin,Xi-Wang Liu,Shi-Hong Li,Li-Xia Bai,Jian-Yong Li

Aspirin eugenol ester (AEE) is a new pharmaceutical compound esterified by aspirin and eugenol, which has anti-inflammatory, antioxidant, and other pharmacological activities. The aim of this study was to investigate the protective effect of AEE on paraquat- (PQ-) induced cell damage of SH-SY5Y human neuroblastoma cells and its potential molecular mechanism. There was no significant change in cell viability when AEE was used alone. PQ treatment reduced cell viability in a concentration-dependent manner. However, AEE reduced the PQ-induced loss of cell viability. Flow cytometry, terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL), and 46-diamidino-2-phenylindole (DAPI) staining were used to evaluate cell apoptosis. Compared with the PQ group, AEE pretreatment could significantly inhibit PQ-induced cell damage. AEE pretreatment could reduce the cell damage of SH-SY5Y cells induced by PQ via reducing superoxide anion, intracellular reactive oxygen species (ROS), and mitochondrial ROS (mtROS) and increasing the levels of mitochondrial membrane potential (). At the same time, AEE could increase the activity of glutathione peroxidase (GSH-Px), catalase (CAT), and superoxide dismutase (SOD) and decrease the activity of malondialdehyde (MDA). The results showed that compared with the control group, the expression of p-PI3K, p-Akt, and Bcl-2 was significantly decreased, while the expression of caspase-3 and Bax was significantly increased in the PQ group. In the AEE group, AEE pretreatment could upregulate the expression of p-PI3K, p-Akt, and Bcl-2 and downregulate the expression of caspase-3 and Bax in SH-SY5Y cells. PI3K inhibitor LY294002 and the silencing of PI3K by shRNA could weaken the protective effect of AEE on PQ-induced SH-SY5Y cells. Therefore, AEE has a protective effect on PQ-induced SH-SY5Y cells by regulating the PI3K/Akt signal pathway to inhibit oxidative stress.

CAS / MDL: 1910-42-5
研究领域: 药理学 · 毒理学 · 细胞生物学 · 神经科学
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2020 · IF 3.99

Copolymer of eugenol-based and pyrogallol-based benzoxazines: Low curing temperature and enhanced corrosion resistance

Chen Chen,Yuzhu Cao,Xin Lu,Xiu Li,Hongjie Yao,Zhong Xin

In this work, eugenol/stearylamine-based benzoxazine (E-s) and pyrogallol/furfurylamine-based benzoxazine (PY-f) were synthesized from renewable raw materials and mixed to prepare a series of copolymers. The curing behavior of E-s/PY-f mixtures were characterized by differential scanning calorimetry (DSC). The result shows that the curing temperature decreased obviously with the increase of PY-f content. When the mass ratio of E-s to PY-f was 8:2, the exothermic peak temperature ( T p ) of the sample (EP20) dropped to 194 ℃, which was 70 ℃ lower than that of E-s. Then, the representative copolymerization mechanism of E-s and PY-f was proposed. Furthermore, EP20 was adopted to prepare the copolymer coating (PEP) on mild steel (MS) for anti-corrosion application. The results of electrochemical impedance spectroscopy (EIS) indicated that PEP-coated MS well kept its corrosion resistance after being immersed in 3.5 wt% NaCl aqueous solution for 30 days. Hence, the copolymer of bio-based benzoxazines is promising for preparing superior anti-corrosion material with low curing temperature.

CAS / MDL: 141-78-6 87-66-1
研究领域: 材料科学 · 化学工程 · 腐蚀科学
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JOURNAL OF BIOMATERIALS APPLICATIONS · 2019 · IF 2.442

Fabrication of carboxymethylcellulose hydrogel containing β-cyclodextrin–eugenol inclusion complexes for promoting diabetic wound healing

Mengdie Li,Fang Li,Tao Wang,Liang Zhao,Yijie Shi

The difficult healing of wounds caused by diabetes remains a challenging clinical problem. The activation of nuclear factor kappa-B as a key factor contributes to prolonged inflammation and inhibition of angiogenesis. As a natural antioxidant, eugenol may downregulate the lectin-like oxidized low-density lipoprotein receptor-1 and inhibit the activation of nuclear factor kappa-B in endothelial cells. However, eugenol shows poor solubility, pungent odor, and volatility, thus impeding its clinical application as a potential therapeutic agent. This study developed a novel bioactive carboxymethylcellulose hydrogel loaded with inclusion complexes of eugenol with β-cyclodextrin (eugenol–β-cyclodextrin/carboxymethylcellulose hydrogel) to regulate lectin-like oxidized low-density lipoprotein receptor-1-induced activation of nuclear factor kappa-B to enhance angiogenesis and inhibit inflammation for accelerating diabetic wound healing in vivo. It was found that eugenol–β-cyclodextrin/carboxymethylcellulose hydrogel exhibited remarkable antibacterial activity in vivo and in vitro. Furthermore, it accelerated diabetic wound healing by reducing the lectin-like oxidized low-density lipoprotein receptor-1/nuclear factor kappa-B-induced dysfunction in endothelial cells and promoting angiogenesis.

CAS / MDL: 9004-32-4
研究领域: 药剂学 · 材料科学 · 生物医学工程 · 伤口愈合
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2021 · IF 4.539

Effective adsorption of arsenate, dyes and eugenol from aqueous solutions by cationic supramolecular gel materials

Zujin Yang,Guifang Wu,Cui Gan,Guangmei Cai,Jianyong Zhang,Hongbing Ji

Developing efficient separation technologies for wastewater treatment and recovery of natural products is crucial in practical application. Covalent capture of supramolecular gel materials and the further surface modification benefit for the improvement in adsorption performance. In the present paper, two kinds of supramolecular gels, N , N ', N ”-(3-methylpyridine) benzenetriamide (TMPTA) nanotube and N , N ', N ”-(3-pyridyl) benzenetriamide (TPTA) nanofiber, were synthesized successfully by supramolecular self-assembly of tripodal pyridines and then were further modified with α,α'-dibromo-p-xylene to obtain imidazolium-based gel materials, TMPTA-G-M and TPTA-G-M. They have stable porous structure and positively charged surfaces with different morphologies. The synthesized gels are characterized by physico-chemical techniques, and the results show that the modification process does not cause significant changes in the morphology. TMPTA-G-M and TPTA-G-M are applied as adsorbents for the selective separation of anionic Congo Red (CR) and cationic dye Rhodamine B (RhB) from aqueous solutions. Maximum adsorption amounts ( q max ) on TPTA-G-M are 87.95 mg/g for CR and 85.83 mg/g for RB, and on TMPTA-G-M are 372.03 mg/g for CR and 45.64 mg/g for RB, respectively. For the arsenate adsorption, TMPTA-G-M showed significantly better adsorption performance with q max of 66.5 mg/g in solutions at pH = 9 in 10 min. Additionally, TMPTA-G-M is used for the selective separation of eugenol from eugenol acetate which coexist extensively in Clove oil , and it shows excellent adsorption selectivity for eugenol with q max of 93.59 mg/g at pH = 11. The mechanism study suggests that the morphology of the gels affects the distribution of charge and further affects the adsorption performance. And the adsorption may involve electrostatic interactions between adsorbent and adsorbate. The results indicate high adsorption ability and regeneration efficiency for TMPTA-G-M, implying the potential application in wastewater treatment and separation of natural product.

研究领域: 环境科学 · 材料科学 · 化学工程
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JOURNAL OF POLYMER RESEARCH · 2016 ·Vol. 23 ·期 6 ·1-12 · IF 1.969

Self-healing polymers based on eugenol via combination of thiol-ene and thiol oxidation reactions

Cheng Chuanjie,Zhang Xu,Chen Xinghe,Li Jin,Huang Qinghua,Hu Zhongyu,Tu Yuanming

Eugenol, a relatively cheap and abundant renewable resource, is used to design terminal diene compounds. Thiol-ene click reactions between the terminal diene intermediates and 1,6-hexanedithiol afford the corresponding oligomers with molecular mass of about 1.3 kDa. Finally, the oligomers and tricapto compound trimethylolpropane tris(3-mercaptopropionate) undergo thiol-oxidation reactions to form disulfide-crosslinked polymers. The brown polymers indicate self-healable behavior under UV light irradiation, presumably due to reversible reshuffling of weak disulfide bonds and/or reversible addition-dissociation reaction between benzoxazine and thiol groups.

研究领域: 材料科学 · 有机化学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2015 · IF 2.416

Influence of surfactant and oil composition on the stability and antibacterial activity of eugenol nanoemulsions

Wei Li,Huanle Chen,Zongze He,Cong Han,Shilin Liu,Yan Li

Eugenol (Eu) nanoemulsions were prepared by high-pressure homogenization with two surfactants and varied oil compositions. Their stability and antibacterial activities were further evaluated. The results from dynamic light scattering demonstrated that the stability of bulk Eu emulsions stabilized by sodium dodecylsulfate (SDS) was worse than that by Tween 80 (T80). The improvement of emulsion stability by addition of bean oil (BO) depended on the interfacial surfactants. For SDS-stabilized emulsions, Eu emulsions would become stable with the increasing amount of BO. For T80-stabilized emulsions, the improvement of Eu emulsion stability was noticeably different as reported. With the increment of BO, Eu emulsions became stable first, then unstable and finally stable. The repeat instability occurred in Eu emulsions at 60 wt% BO. The results of antibacterial activity showed that emulsion encapsulation could protect and even enhance the antibacterial activity of Eu. The antibacterial capacity of Eu emulsions was affected by the surfactant type, listed as anionic > nonionic surfactant. Time-kill assay presented that lower BO content in Eu-T80 emulsions, the better effect was obtained on the bacterial inhibition against E. coli .

CAS / MDL: 97-53-0
研究领域: 食品科学 · 微生物学 · 药剂学
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CHEMICAL ENGINEERING JOURNAL · 2020 · IF 10.652

Synthesis of a novel nonflammable eugenol-based phosphazene epoxy resin with unique burned intumescent char

Jinghong Liu,Zhuojian He,Guohui Wu,Xiaoqing Zhang,Chen Zhao,Caihong Lei

Developing bioresourced epoxy resin with excellent flame retardancy is challenging for satisfying environmental and fire hazard requirements. Herein, a novel monomer with six functional epoxy groups was successfully synthesized by combining eugenol with hexachlorocyclotriphosphazene. Using aliphatic diamine as a curing agent, a novel epoxy of EHPE-D230 was prepared, and its properties were systematically evaluated. Compared with commercial epoxy resin (E51-D230), EHEP-D230 possessed a higher tensile strength (56.7 to 64.2 MPa) and better thermal resistance (T α  = 85 to 119 °C). Moreover, EHEP-D230 exhibited a high limiting oxygen index value of 31%, and it passed the UL94 V-0 test without any after-flame time. Cone calorimeter test indicated that the peak value of the heat release rate, total heat release, and total smoke production for EHEP-D230 reduced significantly by 66%, 65%, and 78%, respectively, compared with those of E51-D230. The EHEP-D230 residual char exhibited a compact and continuous exterior structure and a honeycomb-like hollow vesicle interior structure. This unique intumescent char endowed EHEP-D230 with excellent flame retardancy and smoke suppression, rendering it a potential candidate for fire-resistant applications.

研究领域: 材料科学 · 化学工程
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2022 · IF 5.999

Fabrication of cellulose acetate/gelatin-eugenol core–shell structured nanofiber films for active packaging materials

Yuanyue Shi,Xueke Cao,Zhaozhang Zhu,Jing Ren,Hao Wang,Baohua Kong

In this study, novel active materials based on cellulose acetate (CA) and gelatin (Gel) for the release of eugenol (Eg) were developed by fabricating CA/Gel-Eg core–shell structured nanofiber films using the coaxial electrospinning technique. These electrospun nanofibers were coated with a CA shell, which has excellent water stability. Eg was encapsulated on the core part of the Gel. CA/Gel-Eg fiber morphology, structure, thermal, surface wettability , mechanical, encapsulation efficiency, release profile, and biological activity were evaluated. Results showed that the Eg-loaded nanofibers had uniform fiber morphologies and average fiber diameters ranging from 302.5 to 166.6 nm. Eg could be efficiently encapsulated in nanofibers and released for 120 h. Additionally, the CA/Gel-Eg core–shell structured nanofiber films displayed good Eg dose-dependent antibacterial activity . These findings could lead to a new strategy for developing electrospun fibers with a core–shell structure for active food packaging applications.

CAS / MDL: 9004-35-7
研究领域: 材料科学 · 纳米技术 · 食品科学 · 生物技术
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Artificial Biosynthetic Pathway for Efficient Synthesis of Vanillin, a Feruloyl-CoA-Derived Natural Product from Eugenol

Xiaochong Zhu,Jieyuan Wu,Shizhong Li,La Xiang,Jian-Ming Jin,Chaoning Liang,Shuang-Yan Tang

Eugenol, the main component of essential oil from the Syzygium aromaticum clove tree, has great potential as an alternative bioresource feedstock for biosynthesis purposes. Although eugenol degradation to ferulic acid was investigated, an efficient method for directly converting eugenol to targeted natural products has not been established. Herein we identified the inherent inhibitions by simply combining the previously reported ferulic acid biosynthetic pathway and vanillin biosynthetic pathway. To overcome this, we developed a novel biosynthetic pathway for converting eugenol into vanillin, by introducing cinnamoyl-CoA reductase (CCR), which catalyzes conversion of coniferyl aldehyde to feruloyl-CoA. This approach bypasses the need for two catalysts, namely coniferyl aldehyde dehydrogenase and feruloyl-CoA synthetase, thereby eliminating inhibition while simplifying the pathway. To further improve efficiency, we enhanced CCR catalytic efficiency via directed evolution and leveraged an artificialvanillin biosensor for high-throughput screening. Switching the cofactor preference of CCR from NADP+ to NAD+ significantly improved pathway efficiency. This newly designed pathway provides an alternative strategy for efficiently biosynthesizing feruloyl-CoA-derived natural products using eugenol.

研究领域: 生物化学 · 合成生物学
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MICROCHEMICAL JOURNAL · 2024 · IF 4.9

Electroosmotic coupled with particle-assisted deep eutectic solvent flotation for the enrichment of eugenol from clove

Mengyao Gao,Chen Yan,Na Li,Yun Wei

Eugenol has many biological and pharmacological activities such as antioxidant, anticancer, anti-inflammatory, antibacterial and anesthetic.   In view of its wide range of beneficial activities, it is crucial to establish a method for the separation and purification of active components from clove. In this study, an electroosmotic coupled with particle-assisted deep eutectic solvent flotation method was established for the enrichment of eugenol from clove. Ten deep eutectic solvent (DES) extraction systems based on menthol as the hydrogen bond acceptor (HBA) were screened, and butanol was determined as the hydrogen bond donor (HBD) to prepare the optimal DES as extractant for extracting eugenol. Under the optimum operating conditions including solid–liquid ratio of 1:30, flotation time of 50 min, nitrogen flow rate of 55 mL/min, salt content of 20 g, pH of the clove suspension of 5.2, applied voltage of 15 V, copper electrode at the bottom, the yield of eugenol was 45.89 ± 1.61 mg/g. Compared with other extraction methods, the extraction rate was greatly improved. The electroosmotic coupled with particle-assisted deep eutectic solvent flotation method provides a green and efficient enrichment strategy for natural product, which has broad application prospects.

研究领域: 化学工程 · 药学 · 分析化学 · 天然产物研究
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EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS · 2024 · IF 4.4

Development of an innovative eugenol and borax-based orodispersible film for enhanced treatment of mouth ulcers

Shu-Yin Liu,Hui Chen,Feng Zhou,Jian-Ping Zheng,Jian-Tao Zhang

Orodispersible films (ODFs) have emerged as an advanced and patient-friendly delivery system due to ease of administration, improved patient compliance, quick release and taste-masking of active pharmaceutical ingredients. This research reports the preparation of the ODF containing eugenol and borax (EB-ODF) by a solvent casting technique for treating mouth ulcers. The EB-ODF consisted of vinyl pyrrolidone/vinyl acetate copolymer (Kollidon® VA64, VA64) and hydroxypropyl methylcellulose (HPMC-K250) as the film formers where eugenol and borax were loaded. The thickness of the EB-ODF obtained was 0.119 ± 0.001 mm and the tensile strength was 13.1 ± 1.1 N/mm 2 ( p  > 0.05). The prepared films disintegrated in the oral cavity within 30 s and over 90% of the eugenol was released from the film in the first 5 min. Furthermore, the combined application of eugenol and borax, loaded in EB-ODF, displayed notable synergetic antibacterial property against both gram-negative and gram-positive bacteria. In an in-vivo study on a rat model with chemical burn-induced oral ulcers, the EB-ODF treatment group had a 100% reduction in ulcer area ( p  > 0.05) after 10 days of treatment and demonstrated a 38.7% higher reduction in oral ulcer area compared to the Dingpeng Cream treatment group ( p  < 0.0001). The EB-ODF treatment group showed minimal oral irritation, scoring only 1 point and a 65% preference in the taste tests ( p  < 0.0001). In summary, EB-ODF had successfully overcome the poor palatability of commercially available formulation and provided notable potential for further ulcer treatment product development.

CAS / MDL: 9012-76-4 56-81-5
研究领域: 药学 · 药理学 · 药物递送系统 · 口腔医学
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