CHEMISTRY & BIODIVERSITY
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2025
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IF 2.5
Huilu Sun,Ruxue Wei,Genqiang Chen,Zhiping Che,Xiaobo Huang,Yingwu Chen,Yuee Tian
Eugenol is the main component of clove basil oil extracted from plants such as Syzygium aromaticum and Ocimum gratissimum . To discover biorational natural product-based pesticides, a series of eugenol/dihydroeugenol derivatives containing carbamate moiety were prepared by introducing an active aminooyloxy group at its C1 hydroxy position, and their structures were well characterized by proton nuclear magnetic resonance ( 1 H NMR), carbon-13 NMR ( 13 C NMR), high-resolution mass spectrometry, and melting point. Bioactivities of these target compounds as anti-oomycete and anti-fungal agents against two serious agricultural pests, Phytophthora capsici and Fusarium graminearum were evaluated. Among assessed compounds: (1) Title compounds 1b and 2b showed significant anti-fungal against F. graminearum , with half maximal effective concentration values of 29.13 and 35.04 mg/L, respectively. (2) The title compounds have obvious selectivity, and their anti-fungal activity is significantly better than their anti-oomycete activity. (3) The anti-oomycete and anti-fungal activities of introducing the aminoalkyloyloxy group at the C1 hydroxyl position of eugenol or dihydroeugenol are significantly better than that of introducing the aminoaryloyloxy group. (4) The presence of a double bond is beneficial for increasing anti-fungal activity, and the reduction of a double bond is beneficial for increasing anti-oomycete activity. Graphical
研究领域:
植物化学
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农药科学
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生物化学
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DOI
PubMed
高影响因子
Food Additives and Contaminants Part A-Chemistry Analysis Control Exposure & Risk Assessment
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2022
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IF 3.549
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
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分析化学
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2021
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IF 5.279
Xiuhai Gan,Zhengxing Wang,Deyu Hu
To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL–1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL–1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL–1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL–1), eugenol (456.3 and 463.2 μg mL–1), isoeugenol (478.4 and 487.5 μg mL–1), and ningnanmycin (246.5 and 286.6 μg mL–1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.
研究领域:
植物化学
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病毒学
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药物化学
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DOI
PubMed
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
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2023
·
IF 6
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.
研究领域:
食品科学
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材料科学
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植物病理学
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DOI
高影响因子
Coatings
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2018
·Vol. 8
·期 3
·88
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IF 2.35
Jinyue Dai,Shimin Yang,Na Teng,Yuan Liu,Xiaoqing Liu,Jin Zhu,Jun Zhao
In this work, several bio-based main-chain type benzoxazine oligomers (MCBO) were synthesized from eugenol derivatives via polycondensation reaction with paraformaldehyde and different diamine. Afterwards, their chemical structures were confirmed by Fourier Transform Infrared Spectroscopy (FT-IR) and Nuclear Magnetic Resonance Spectroscopy (1H-NMR). The curing reaction was monitored by Differential Scanning Calorimetry (DSC) and FT-IR. The polybenzoxazine films were prepared via thermal ring-opening reaction of benzoxazine groups without solvent, and their thermodynamic properties, thermal stability, and coating properties were investigated in detail. Results indicated that the cured films exhibited good thermal stability and mechanical properties, showing 10% thermal weight loss (Td10%) temperature as high as 408 °C and modulus at a room temperature of 2100 MPa as well as the glass transition temperature of 123 °C. In addition, the related coatings exhibited high hardness, excellent adhesion, good flexibility, low moisture absorption, and outstanding solvent resistance.Keywords:bio-based;benzoxazine;eugenol;coatings
研究领域:
材料科学
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化学工程
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DOI
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2024
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IF 5.6
Xuanhao Huang,Xinyi Guo,Yao Meng,Shaobo Lou,Xinxing Wu,Yan Zhang,Renzhong Wei,Shuaibo Han,Fangli Sun,Hui Wang
Bamboo, which has excellent physical properties and environmental credentials, is widely used in the construction industry and furniture manufacturing. Bamboo is, however, susceptible to attack by molds and bacteria; protection by natural phenolic antimicrobial agents would be a green and environmentally friendly solution to this problem. The application of such protection has, so far, been hampered by poor stability and ease of volatilization of the antimicrobial agent. Here, an innovative strategy that uses the catalytic action of the laccase to chemically attach a natural antimicrobial agent, eugenol (EU), to bamboo, is described. This modification endows bamboo with both long-lasting and extensive mold resistance and antibacterial activity. Laccase-catalyzed covalent bonding of EU to bamboo reduces the volatilization rate of the EU from 1.72 % to 0.29 %. The outstanding mold resistance and antimicrobial activity of bamboo treated using this modified process is retained during a 50-day mold resistance test, with mold growth inhibited by as much as 87.5 %. The treated bamboo is also able to inhibit the growth of both Gram-positive and Gram-negative bacteria. The antimicrobial mechanism results shown that the bamboo lignin is the primary reaction site during laccase-catalyzed EU modification of bamboo, and the long-term mold resistance derived from modified lignin. Furthermore, we analyzed bacterial morphology through SEM, and the results demonstrated that modified enzymatic hydrolysis lignin (EHL) significantly disrupts bacterial morphology, including membrane invagination and collapse. This study provides a new direction for the green development of mold- and bacteria-resistant bamboo, which has potential for use in a wide range of application.
研究领域:
材料科学
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微生物学
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植物化学
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DOI
高影响因子
MICROCHIMICA ACTA
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2021
·Vol. 188
·期 7
·1-14
·
IF 5.833
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
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纳米技术
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电化学
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食品科学
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DOI
PubMed
高影响因子
CARBOHYDRATE POLYMERS
·
2018
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IF 5.158
Ying Shao,Chunhua Wu,Tiantian Wu,Yuan Li,Shiguo Chen,Chunhong Yuan,Yaqin Hu
Eugenol is widely used in food industries where it encounters major concerns such as its poor solubility and stability. Herein, a novel eugenol-nanoemulsion was prepared by using ultrasonication as emulsification techniques, chitosan nanoparticle as carrier, and surfactant, as emulsifier. The results indicated that droplet size and encapsulation efficiency of the nanoemulsions was significantly affected by testing factors. The selected parameters for nanoemulsions were determined as chitosan-eugenol ratio of 1:1, Tween20 1 wt/v%, ultrasonic power 450 W and ultrasonic time 6 min. The nanoparticles were performed in regularly spherical shape distributed within 80–100 nm. Besides, the nanoemulsions showed great storage stability and thermal stability and the nanoeparticles performed excellent antioxidant capacity, antimicrobial activity as well as an initial burst of eugenol followed by plateau. Therefore, eugenol-chitosan nanoemulsions had great potential in food formulations for extending the shelf life.
研究领域:
食品科学
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纳米技术
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生物学
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产品关联
DOI
PubMed
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2021
·
IF 3.963
Shanshan Gao,Ruixue Lu,Yonglei Zhang,Haidi Sun,Siying Li,Kunpeng Zhang,Ruimin Li
Tribolium castaneum ( T. castaneum ) is a worldwide pest of stored grain that mainly harms flour, and not only causes serious loss of flour quality but also leads to deterioration of flour quality. Chemical detection plays a key role in insect behavior, and the role of odorant-binding proteins (OBPs) in insect chemical detection has been widely studied. However, the mechanism of OBPs in insect defense against exogenous toxic substances is still unclear. In this study, biochemical analysis showed that eugenol , the active component of A. vulgaris essential oil , significantly induced the expression of the OBP gene OBPC12 from T. castaneum ( TcOBPC12 ). The mortality of late larvae treated with eugenol was higher than that of the control group after RNA interference (RNAi) against TcOBPC12 , which indicates that the OBP gene is involved in the eugenol defense mechanism and leads to a decrease in sensitivity to eugenol. Tissue expression profiling showed that the expression of TcOBPC12 in the epidermis, hemolymph, and intestine was higher than in other larval tissues, and TcOBPC12 was expressed mainly in the epidermis, head, and fat body of adults. The developmental expression profile showed that the expression of TcOBPC12 in late eggs, early and late larval stages, and late adult stages was higher than in other developmental stages. These data suggest that TcOBPC12 may be involved in the absorption of exogenous toxic substances by the larvae from T. castaneum . Our results provide a theoretical basis for the metabolism and degradation mechanism of exogenous toxic substances and help explore more potential target genes of insect pests .
研究领域:
昆虫学
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分子生物学
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产品关联
DOI
PubMed
高影响因子
ELECTRONIC JOURNAL OF BIOTECHNOLOGY
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2018
·
IF 1.881
Peng-Cheng Chen,Hui Zhang,Pu Zheng
Background Eugenol is an economically favorable substrate for the microbial biotransformation of aromatic compounds. Coniferyl aldehyde is one kind of aromatic compound that is widely used in condiment and medical industries; it is also an important raw material for producing other valuable products such as vanillin and protocatechuic acid. However, in most eugenol biotransformation processes, only a trace amount of coniferyl aldehyde is detected, thus making these processes economically unattractive. As a result, an investigation of new strains with the capability of producing more coniferyl aldehyde from eugenol is required. Results We screened a novel strain of Gibberella fujikuroi , labeled as ZH-34, which was capable of transforming eugenol to coniferyl aldehyde. The metabolic pathway was analyzed by high-performance liquid chromatography–mass spectrometry and transformation kinetics. The culture medium and biotransformation conditions were optimized. At a 6 h time interval of eugenol fed-batch strategy, 3.76 ± 0.22 g/L coniferyl aldehyde was obtained, with the corresponding yield of 57.3%. Conclusions This work improves the yield of coniferyl aldehyde with a biotechnological approach. Moreover, the fed-batch strategy offers possibility for controlling the target product and accumulating different metabolites. How to cite: Chen P-C, Zhang H, Zheng P. Direct biodegradation of eugenol into coniferyl aldehyde and other higher value-added products by Gibberella fujikuroi ZH-34. Electron J Biotechnol 2019;38. https://doi.org/10.1016/j.ejbt.2018.12.001 .
研究领域:
微生物学
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生物技术
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产品关联
DOI
高影响因子
ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY
·
2023
·
IF 6.8
Tao Zhang,Hongzhen Sun,Shuai Hu,Shaowu Ding,Peng Zhang,Ling Wang,Weidi Fan,Feng Liu,Wei Mu,Xiuyu Pang
Currently, there is a pressing need to develop an agrochemical-loaded system that is both uncomplicated and efficient, thereby enhancing the adhesion of agrochemical to leaf surfaces and optimizing their insecticidal efficacy, while concurrently mitigating environmental risks. The flexible eugenol-loaded particles were synthesized via a one-step polyurethane self-assembly reaction, utilizing polyethylene glycol (PEG) as the soft segment and 4,4-diphenylmethane diisocyanate (MDI) as the hard segment. The increase in the length of the soft segment enhances the flexibility of the particles, thereby improving the contact area and adhesion with the foliar surface. When flexible particles are applied on the foliar surface, they can achieve satisfactory resistance to rainfall erosion. When the PEG molecular weight is 800, the residual concentration of eugenol can still reach 42.11% after 6 washes. The carrier protects the active ingredients and improves the resistance to ultraviolet irradiation. After 5 h of ultraviolet irradiation, the concentration of eugenol remained at 59.03% when PEG with a molecular weight of 200 was employed. Greenhouse experiments showed that the flexible transformation of particles greatly enhanced the application effect of spray on the foliar surface of particles. After undergoing three washes, the mortality of the particles can be enhanced by 5.4–8.4 times compared to that of emulsion concentrate (EC) sample. The enhancement of leaf retention performance reduces environmental risks caused by pesticide loss. Meanwhile, the controlled release of particles also reduces the acute toxicity to zebrafish. The toxicity selection pressure of the EUG@P800-Ps sample is 10.6 times that of the EC sample. In conclusion, the preparation process of the system is simple, and the flexible transformation is an effective strategy to improve the foliar application effect of spray and improve the environmental safety.
研究领域:
农业科学
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生态毒理学
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植物保护
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产品关联
DOI
PubMed
高影响因子
COMPOSITES PART B-ENGINEERING
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2020
·
IF 7.635
Jingkai Liu,Jinyue Dai,Shuaipeng Wang,Yunyan Peng,Lijun Cao,Xiaoqing Liu
With the purpose to obtain an eco-friendly flame retardant for epoxy resin, a facile method for the synthesis of a bio-based epoxy monomer containing DOPO units (DGEBDB) from lignin-derived vanillin and guaiacol, was presented in this work. During the synthesis process, guaiacol acted as both reactant and solvent. And it could be recycled in situ and re-used as the fresh one. In order to evaluate the flame retardancy of DGEBDB, it was mixed with diglycidyl ether of bisphenol A (DGEBA) and cured with 4,4-diaminodiphenylmethane (DDM). Results showed that, DGEBDB demonstrated a good compatibility with DGEBA, and the mechanical properties of cured resins were obviously improved with the addition of DGEBDB. As expected, the limiting oxygen index (LOI) of cured resin reached 30.2% with the content of phosphorus only 0.67 wt%, in which the weight ratio between DGEBDB and DGEBA was 1:9 (B1D9/DDM). When the weight ratio of DGEBDB to DGEBA was further increased to 2:8 for the B2D8/DDM system, the UL-94 V-0 grade was achieved. Meanwhile, the mechanism of DGEBDB in improving the flame retardancy of cured resin was discussed and revealed. This easily available and eco-friendly DGEBDB was proved to be a highly efficient reactive flame retardant for epoxy resin.
研究领域:
材料科学
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化学工程
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产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）