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In this study, essential oils and waste hydrosols of leaves of Ocimum tenuiflorum in four different geographical locations were extracted by hydrodistillation method and using gas chromatography/mass spectrometry (GC/MS) for chemical composition analysis. All four essential oil samples contained the main components (E)-β-caryophyllene (27.8-49.0 %), trans-β-elemene (20.3-37.1 %) and eugenol (9.0-44.0 %). Three of the four hydrosol samples had eugenol in absolute content (94.5-98.6 %), while the remaining hydrosol sample had two main components, elemicin (77.8 %) and eugenol (14.2 %). Essential oils and hydrosols demonstrated larvicidal activities against four important disease-transmitting mosquito species including Aedes aegypti, Aedes albopictus, Culex quinquefasciatus, and Culex fuscocephala with 24-h LC 50 values in the range 15.42-56.01 μg/mL and 53.88-97.80 μg/mL for the essential oils and the hydrosols, respectively. Essential oils and hydrosols strongly inhibited the acetylcholinesterase (AChE) enzyme of electric eels with IC 50 values in the range of 25.35-107.19 μg/mL. Microemulsion (ME) can be considered as a sustainable pesticide formulation over 300 days and has improved larvicidal activity compared to free essential oil. The O. tenuiflorum in Vietnam can be considered a low-cost source of eugenol, botanical pesticides that control disease-transmitting mosquitoes, as well as having therapeutic potential to be further investigated., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

The purpose of this study was to prepare Pickering emulsion with synergistic antibacterial effect using whey protein isolated-citral (WPI-Cit) nanoparticles with eugenol for grape preservation. In this emulsion, eugenol was encapsulated in oil phase. The particle size, ζ-potential, and antibacterial mechanism of the nanoparticles were characterized. The rheological properties, antibacterial effects and preservation effects of WPI-Cit Pickering emulsion were measured. The results showed that the optimal preparation condition was performed at WPI/Cit mass ratio of 1:1, WPI-Cit nanoparticles were found to damage the cell wall and membrane of bacteria and showed more effective inhibition against S. aureus. Pickering emulsion prepared with WPI-Cit nanoparticles exhibited a better antibacterial effect after eugenol was encapsulated in it, which extended the shelf life of grapes when the Pickering emulsion was applied as a coating. It demonstrated that the Pickering emulsion prepared in this study provides a new way to extend the shelf life., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

This article explores the important, and yet often overlooked, solid-state structures of selected bioaromatic compounds commonly found in lignin hydrogenolysis oil, a renewable bio-oil that holds great promise to substitute fossil-based aromatic molecules in a wide range of chemical and material industrial applications. At first, single-crystal X-ray diffraction (SCXRD) was applied to the lignin model compounds, dihydroconiferyl alcohol, propyl guaiacol, and eugenol dimers, in order to elucidate the fundamental molecular interactions present in such small lignin-derived polyols. Then, considering the potential use of these lignin-derived molecules as building blocks for polymer applications, structural analysis was also performed for two chemically modified model compounds, i.e., the methylene-bridging propyl-guaiacol dimer and propyl guaiacol and eugenol glycidyl ethers, which can be used as precursors in phenolic and epoxy resins, respectively, thus providing additional information on how the molecular packing is altered following chemical modifications. In addition to the expected H-bonding interactions, other interactions such as π-π stacking and C-H∙∙∙π were observed. This resulted in unexpected trends in the tendencies towards the crystallization of lignin compounds. This was further explored with the aid of DSC analysis and CLP intermolecular energy calculations, where the relationship between the major interactions observed in all the SCXRD solid-state structures and their physico-chemical properties were evaluated alongside other non-crystallizable lignin model compounds. Beyond lignin model compounds, our findings could also provide important insights into the solid-state structure and the molecular organization of more complex lignin fragments, paving the way to the more efficient design of lignin-based materials with improved properties for industrial applications or improving downstream processing of lignin oils in biorefining processes, such as in enhancing the separation and isolation of specific bioaromatic compounds).

In this study, a novel bio-composite material that allow sustained release of plant derived antimicrobial compound was developed for the biomedical applications to prevent the infections caused by microorganisms resistant to commercial antimicrobials agents. With this aim, bacterial cellulose (BC)-p(HEMA) nanocomposite film that imprinted with eugenol (EU) via metal chelated monomer, MAH was prepared. Firstly, characterization studies were utilized by FTIR, SEM and BET analysis. Then antimicrobial assays, drug release studies and in vitro cytotoxicity test were performed. A significant antimicrobial effect against both Gram (+) Staphylococcus aureus and Gram (-) Escherichia coli bacteria and a yeast Candida albicans were observed even in low exposure time periods. When antimicrobial effect of EU compared with commercially used agents, both antifungal and antibacterial activity of EU were found to be higher. Then, sustained drug release studies showed that approximately 55% of EU was released up to 50 h. This result proved the achievement of the molecular imprinting for an immobilization of molecules that desired to release on an area in a long-time interval. Finally, the in vitro cytotoxicity experiment performed with the mouse L929 cell line determined that the synthesized EU-imprinted BC nanocomposite was biocompatible.

Purpose: This study was designed to investigate the effect of post space conditioning with different solutions on the bond strength of glass FRC posts and evaluate the mode of resin failure., Methods: Sixty extracted human single rooted teeth were root filled using a resin sealer and suitable gutta-percha cones. Post spaces were prepared, and the teeth randomly allocated into 5 groups according to their irrigation regimens which included the following solutions: 17 % EDTA, 2 % CHX, 3 % NaOCl, 10 % ascorbic acid and QMix solutions. Post spaces were irrigated with 5 ml of the solution for 15 s and subsequently washed with distilled water and dried with paper points. Glass FRC posts were cemented into their spaces using a self-adhesive resin cement. The specimens were mounted in plexiglass molds using autopolymerizing acrylic resin. A universal testing machine was used to measure post retention at a crosshead speed of 2 mm/min. The results were analyzed by one-way ANOVA followed by Tukey HSD test (α = 0.05). Dislodged posts and post spaces were examined microscopically to evaluate retention failure., Results: The Ascorbic acid group exhibited the highest mean retentive strength value at 229 N, followed by QMix at 198 N, NaOCl at 186 N, CHX at 170 N, and EDTA at 124 N. The mean value of the ascorbic acid group was significantly higher than EDTA group, p = 0.012. The failure category was primarily mixed., Conclusions: Rinsing post spaces with ascorbic acid exhibited significantly superior bond strength. The failure mode was mixed., Clinical Significance: Irrigating post spaces with ascorbic acid solution before luting FRC posts significantly improves their bond strength compared to irrigation with EDTA solution. Irrigation with QMix solution produced the second highest retentive strength but showed no statistical significance when compared to using ascorbic acid, NaOCl, CHX, or EDTA solutions., Competing Interests: Declaration of competing interest The authors have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this manuscript, (Copyright © 2024 Elsevier Ltd. All rights reserved.)

The study aims to explore the effects of Eugenol (EUG) as an antioxidant on α-Chymotrypsin (α-Chy) and its interaction mechanism, with potential implications for new therapy development. The interaction between EUG and α-Chy was demonstrated through ultraviolet (UV) spectroscopy, which resulted in a shift in absorption with docking energies of -22.76 kJ/mol. An increase in fluorescence intensity indicated that the Trp residues moved to a less polar environment, which is consistent with the changes in accessible surface area (ASA) values. The presence of EUG led to a decrease in α-helix, β-turn, and random coil structures as shown by circular dichroism (CD) and Fourier-transform infrared (FTIR) analysis. Additionally, there was a slight increase in β-sheet structures, indicating a decrease in enzyme stability. However, tests for thermal stability showed a decrease in folding upon the introduction of EUG, which contradicted the results obtained from molecular dynamics (MD) simulations. The docking studies revealed that EUG forms hydrogen bonds and van der Waals forces with the enzyme, indicating the interaction mechanism. Kinetic studies confirmed that EUG acts as a mixed inhibitor. However, further research involving live organisms is necessary to fully understand its potential., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier B.V.)

Ultraviolet (UV) light poses a significant threat to human health. Here, we propose a click preparation strategy for creating biomass-based poly(urethane thioether) networks for UV-shielding goggles designed to potentially protect the eyes from UV damage. Eugenol-based diurethanes (EDUs) were synthesized first, and then cross-linked networks were prepared through thiol-ene photoclick chemistry. The obtained high-strength and toughness eugenol-based poly(urethane thioether) networks (EUTNs) show a Young's modulus of 2.6 GPa, a tensile strength of 85 MPa, and a fracture elongation of 2066%. Meanwhile, EUTNs show shape memory behaviors and good optical properties. The EUTN films exhibit transparency while effectively filtering out approximately 99% of UVB and UVC radiation without any UV absorbers added. UV goggles can be integrally fabricated with both lenses and frames made entirely of the same EUTN material. What is more, goggles can be recovered to their original thin film form when not in use.

Active packaging can efficiently enhance the shelf life of food, realizing the encapsulation and effective release of antibacterial agents and antioxidants. Zein is a natural protein derived from corn, widely used in food packaging. In this work, zein-based nanofiber membranes (NFMs) with beaded structures for food packaging were fabricated in batch using a self-made free surface electrospinning. The characteristics of NFMs were investigated in terms of their morphologies, structures and properties. The results illustrated that the antioxidant activity of NFMs was significantly improved after adding licorice extracts. Moreover, after adding the eugenol to the zein/licorice extract NFMs, zein/licorice extract/eugenol (ZLE) NFM had outstanding antibacterial activities against Staphylococcus aureus and Escherichia coli, which effectively prolonged the shelf-life of the grapes when it was used to package grapes. It proved that ZLE NFM had great potential in food packaging applications., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Eugenol, as a natural antibacterial agent, has been widely studied for its inhibitory effect on the common food-borne pathogen Staphylococcus aureus ( S. aureus ). However, the widespread application of eugenol is still limited by its instability and volatility. Herein, γ-polyglutamic acid coated eugenol cationic liposomes (pGA-ECLPs) were successfully constructed by self-assembly with an average particle size of 170.7 nm and an encapsulation efficiency of 36.2%. The formation of pGA shell significantly improved the stability of liposomes, and the encapsulation efficiency of eugenol only decreased by 20.7% after 30 days of storage at 4 °C. On the other hand, the pGA layer can be hydrolyzed by S. aureus , achieving effective control of release through response to bacterial stimuli. The application experiments further confirmed that pGA-ECLPs effectively prolonged the antibacterial effect of eugenol in fresh chicken without causing obvious sensory effects on the food. The above results of this study provide an important reference for extending the action time of natural antibacterial substances and developing new stimuli-responsive antibacterial systems.

The limited vanillin (3a) production from plant sources requires identifying some renewable and sustainable approaches for its synthesis. This study aimed to develop an efficient, eco-friendly process for synthesizing vanillin (3a) from eugenol (1a) and eugenol-rich essential oils. The chemical methodology for vanillin (3a) synthesis involved base-mediated isomerization of eugenol (1a) to isoeugenol (2a), followed by OsO 4 /NaIO 4 mediated oxidation of isoeugenol to vanillin (3a) using different additives such 1,4-diazabicyclo[2.2.2]octane (DABCO) and substituted pyridines in reusable environment-friendly solvents. Use of 2,6-dimethylpyridine and 2,6-dimethylpyridine N-oxide as additives in the oxidation step offered a significantly higher product yield (vanillin 3a, 70 %). The process synthesized vanillin (3a) irrespective of the cis/ trans stereochemistry of isoeugenol (2a). The peculiarity of the method relates to converting eugenol (1a) to vanillin (3a) without phenolic group protection, which offers step economy. Besides efficient vanillin (3a) synthesis, the process's general implications involve converting other naturally occurring phenylpropenes or phenylpropenes-enriched oils to the corresponding phenyl aldehydes (59-82 % yield)., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Electrospun zein-based eugenol nanofibers (ZEnF) with diameters (148.19-631.52 nm) were fabricated. Thermal degradation was found as <15 % until 300 °C while the nanofiber diffraction pattern presented three main peaks among the 5 o and 45 o positions. ZEnF was not only evaluated as non-toxic to cells but also possessed anticancer characteristics revealing with the MCF-7 cell line at 800 μg/mL (reduction: 18.08 %) and 1600 μg/mL (reduction: 41.64 %). Allium tests revealed that ZEnF did not have any adverse impact on the health status (chromosomes-DNA) of exposed organisms. Following the nanofiber coating for chicken meat parts (thigh and breast), it was observed up to 1.25 log CFU/g limitation in total viable bacteria counts (p < 0.05). The sensory score (difference: 3.64 in 10 points scoring on the 6th day of the cold storage) and odor score of chicken meat samples were found to be as higher than control samples (p < 0.05)., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Electrochemical studies were conducted to analyze the behavior of eugenol, CuCl 2 , and their complex using cyclic voltammetry. The oxidation mechanisms of eugenol and the redox behavior of copper ions were elucidated, showing differences in reversibility and charge transfer coefficients. Various kinetic and solvation parameters were determined. The redox behavior of CuCl 2 was found to be more reversible compared to the copper-eugenol complex. The copper-eugenol complex exhibited enhanced antioxidant activity compared to eugenol and standard ascorbic acid. The eugenol was oxidized to form eugenol quinone methide through two postulated irreversible mechanisms. Molecular docking studies suggested higher potential bioactivity of the copper-eugenol complex towards the target protein of COVID-19 than the eugenol ligand., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Protein engineering is crucial to improve enzymes' efficiency and robustness for industrial biocatalysis. NOV1 is a bacterial dioxygenase that holds biotechnological potential by catalyzing the one-step oxidation of the lignin-derived isoeugenol into vanillin, a popular flavoring agent used in food, cleaning products, cosmetics and pharmaceuticals. This study aims to enhance NOV1 activity and operational stability through the identification of distal hotspots, located at more than 9 Å from the active site using Zymspot, a tool that predicts advantageous distant mutations, streamlining protein engineering. A total of 41 variants were constructed using site-directed mutagenesis and the six most active enzyme variants were then recombined. Two variants, with two and three mutations, showed nearly a 10-fold increase in activity and up to 40-fold higher operational stability than the wild-type. Furthermore, these variants show 90-100 % immobilization efficiency in metal affinity resins, compared to approximately 60 % for the wild-type. In bioconversions where 50 mM of isoeugenol was added stepwise over 24-h cycles, the 1D2 variant produced approximately 144 mM of vanillin after six reaction cycles, corresponding to around 22 mg, indicating a 35 % molar conversion yield. This output was around 2.5 times higher than that obtained using the wild-type. Our findings highlight the efficacy of distal protein engineering in enhancing enzyme functions like activity, stability, and metal binding selectivity, thereby fulfilling the criteria for industrial biocatalysts. This study provides a novel approach to enzyme optimization that could have significant implications for various biotechnological applications., Competing Interests: Declaration of Competing Interest L. A.-C. is employed by Zymvol Biomodeling S. L. which owns proprietary rights on the algorithm Zymspot used in this study. All authors have read and agreed to the published version of the manuscript., (Copyright © 2024 The Authors. Published by Elsevier B.V. All rights reserved.)

Eugenol (EU), a natural bioactive compound found in various plants, offers numerous health benefits, but its application in the food and pharmaceutical industry is limited by its high volatility, instability, and low water solubility. Therefore, this study aimed to utilize the surface coating technique to develop zein-tween-80-fucoidan (Z-T-FD) composite nanoparticles for encapsulating eugenol using a nozzle simulation chip. The physicochemical characteristics of the composite nanoparticles were examined by varying the weight ratios of Z, T, and FD. Results showed that the Z-T-FD weight ratio of 5:1:15 exhibited excellent colloidal stability under a range of conditions, including pH (2-8), salt concentrations (10-500 mmol/L), heating (80 °C), and storage (30 days). Encapsulation of EU into Z-T-FD nanoparticles (0.5:5:1:15) resulted in an encapsulation efficiency of 49.29 ± 1.00%, loading capacity of 0.46 ± 0.05%, particle size of 205.01 ± 3.25 nm, PDI of 0.179 ± 0.006, and zeta-potential of 37.12 ± 1.87 mV. Spherical structures were formed through hydrophobic interaction and hydrogen bonding, as confirmed by Fourier transform infrared spectroscopy and molecular docking. Furthermore, the EU-Z-T-FD (0.5:5:1:15) nanoparticles displayed higher in vitro antioxidant properties (with DPPH and ABTS radical scavenging properties at 75.28 ± 0.16% and 39.13 ± 1.22%, respectively), in vitro bioaccessibility (64.78 ± 1.37%), and retention rates under thermal and storage conditions for EU compared to other formulations. These findings demonstrate that the Z-T-FD nanoparticle system can effectively encapsulate, protect, and deliver eugenol, making it a promising option for applications in the food and pharmaceutical industries., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier Ltd.)

In this study, a series of collagen-chitosan-eugenol (CO-CS-Eu) flow-casting composite films were prepared using collagen from sturgeon skin, chitosan, and eugenol. The physicochemical properties, mechanical properties, microstructure, as well as antioxidant and antimicrobial activities of the composite membranes were investigated by various characterization techniques. The findings revealed that the inclusion of eugenol augmented the thickness of the film, darkened its color, reduced the transparency, and enhanced the ultraviolet light-blocking capabilities, with the physicochemical properties of the CO-CS-0.25%Eu film being notably favorable. Eugenol generates increasingly intricate matrices that disperse within the system, thereby modifying the optical properties of the material. Furthermore, the tensile strength of the film decreased from 70.97 to 20.32 MPa, indicating that eugenol enhances the fluidity and ductility of the film. Added eugenol also exhibited structural impact by loosening the film cross-section and decreasing its density. The Fourier transform infrared spectroscopy results revealed the occurrence of several intermolecular interactions among collagen, chitosan, and eugenol. Moreover, the incorporation of eugenol bolstered the antioxidant and antimicrobial capabilities of the composite film. This is primarily attributed to the abundant phenolic/hydroxyl groups present in eugenol, which can react with free radicals by forming phenoxy groups and neutralizing hydroxyl groups. Consequently, inclusion of eugenol substantially enhances the freshness retention performance of the composite film. PRACTICAL APPLICATION: ● The CO-CS-Eu film utilizes collagen from sturgeon skin, improving the use of sturgeon resources.● Different concentrations of eugenol altered its synergistic effect with chitosan.● The CO-CS-Eu film is composed of natural products with safe and edible properties., (© 2024 Institute of Food Technologists.)

Background: Eugenol compounds (EUGs), which share chemical similarities with eugenol, belong to a group of phenolic compounds primarily found in clove oil. They are highly valued by fish dealers due to their exceptional anesthetic properties, playing a crucial role in reducing disease incidence and mortality during the transportation of live fish. Despite their widespread use, the safety of EUGs remains a contentious topic, raising concerns about the safety of aquatic products. This underscores the need for efficient and sensitive analytical methods for detecting EUGs., Results: Nanomaterial-based ratiometric fluorescence immunoassay has gained increasing attention due to its integration of the immunoassay's excellent specificity and compatibility for high-throughput analysis, coupled with the exceptional sensitivity and anti-interference capabilities of ratiometric fluorescence assays. In this study, we developed a sensitive ratiometric fluorescence immunoassay for screening five EUGs. This method employs a broad-specificity monoclonal antibody (mAb) as a recognition reagent, selective for five EUGs. It leverages the horseradish peroxidase (HRP)-triggered formation of fluorescent 2,3-diaminophenazine (DAP) and the quenching of fluorescent gold clusters (Au NCs) for detection. The assay's detection limits for eugenol, isoeugenol, eugenol methyl eugenol, methyl isoeugenol, and acetyl isoeugenol in tilapia fish and shrimp were found to be 9.8/19.5 μg/kg, 0.11/0.22 μg/kg, 19/36 Tilapia ng/kg, 8/16 ng/kg, and 3.0/6.1 μg/kg, respectively. Furthermore, when testing spiked Tilapia fish and shrimp samples, recoveries ranging from 84.1 to 111.9 %, with the coefficients of variation staying below 7.1 % was achieved., Significance: This work introduces an easy-to-use, broad-specificity, and highly sensitive method for the screening of five EUGs at a pg/mL level, which not only provides a high-throughput strategy for screening eugenol-type fish anesthetics in aquatic products, but also can serve as a benchmark for developing immunoassays for other small molecular pollutants, rendering potent technological support for guarding food safety and human health., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. Lin Luo, Zhen-Xi He, Bao-Zhu Jia, Rui-Yao Kang, Wen-Feng Zhang, Ri-Ming Huang, Zhen-Lin Xu., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Headspace solid-phase microextraction coupled to gas chromatography-mass spectrometry (HS-SPME-GC-MS) offers an alternative analysis method for isoeugenol (an active ingredient in fish sedatives) that avoids the use of organic solvents, simplifies sample preparation, and can be fully automated. This work focuses on developing and evaluating an HS-SPME-GC-MS method for isoeugenol in aquaculture samples and testing the stability of isoeugenol itself. Because of isoeugenol's relatively low volatility, more polar SPME fiber coatings (polyacrylate and polydimethylsiloxane/divinylbenzene) had better performance and the headspace extractions took over 30 min to reach equilibrium. Additionally, it was found that isoeugenol was relatively unstable compared to a deuterated standard (d 3 -eugenol) in the presence of water. To address this, after the fish samples were homogenized with water, they were heated at 50 °C for 1 h prior to analysis for equilibration. By using the method developed in this work, isoeugenol's detection limits in multiple aquaculture matrices (shrimp, tilapia, and salmon) were in the low ng/g range (<15 ng/g), well below the target testing level (200 ng/g). Additionally, by adding d 3 -eugenol as an internal standard, excellent linearity ( R 2 > 0.98), accuracy (97-99% recoveries), and precision (5-13% RSDs) were all achieved.

A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via a two-step process, with the key step being a copper(I)-catalyzed azide-alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides , the causative agent of papaya anthracnose. Triazoles 2k , 2m , 2l , and 2n , at 100 ppm, were the most effective, reducing mycelial growth by 88.3, 85.5, 82.4, and 81.4%, respectively. Molecular docking calculations allowed us to elucidate the binding mode of these derivatives in the catalytic pocket of C. gloeosporioides CYP51. The best-docked compounds bind closely to the heme cofactor and within the channel access of the lanosterol ( LAN ) substrate, with crucial interactions involving residues Tyr102, Ile355, Met485, and Phe486. From such studies, the antifungal activity is likely attributed to the prevention of substrate LAN entry by the 1,2,3-triazole derivatives. The triazoles derived from natural eugenol represent a novel lead in the search for environmentally safe agents for controlling C. gloeosporioides .

The amelioration of refractory diabetic ulcers presents a formidable conundrum on a global scale, attributable to the elevated peril of contagion and protracted convalescence durations. Within the purlieus of this reparative epoch, the deployment of efficacious wound coverings endowed with both angiogenesis and antibacterial attributes is of paramount significance. Hydrogel wound dressings are distinguished by their elevated biocompatibility, adhesive tenacity, and innate regenerative capacity. Eugenol, a substance distilled from the blossoms of the lilac, serves as a precursor to metformin and is known to impede the genesis of reactive oxygen species. Although its antibacterial effects have been extensively chronicled, the angiogenic ramifications of eugenol within the context of wound remediation remain under-investigated. This research aimed to evaluate the effectiveness of eugenol-infused hydrogel as a wound dressing material. In this context, polyurethane gelatin (PG) was combined with eugenol at concentrations of 0.5% and 1%, creating PG-eugenol hydrogel mixtures with specific mass ratios for both in vivo and in vitro assessments. The in vivo studies indicated that hydrogels infused with eugenol expedited diabetic wound healing by fostering angiogenesis. Enhanced healing was noted, attributed to improved antibacterial and angiogenic properties, increased cell proliferation, tissue regeneration, and re-epithelialization. The in vitro analyses revealed that eugenol-enriched hydrogels stimulated the growth of fibroblasts (HFF-1) and human umbilical vein endothelial cells (HUVECs) and exhibited antibacterial characteristics. This investigation confirms the potential of eugenol-laden hydrogels in effectively treating diabetic wound defects., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 The Authors. Published by Elsevier B.V. All rights reserved.)

This study investigated the release of aromatic compounds with distinct functional groups within bilayer microcapsules. Bilayer microcapsules of four distinctive core materials (benzyl alcohol, eugenol, cinnamaldehyde, and benzoic acid) were synthesized via freeze-drying. Chitosan (CS) and sodium alginate (ALG) were used as wall materials. CS concentration, using orthogonal experiments with the loading ratio as a metric. Under optimal conditions, three other types of microcapsules (cinnamic aldehyde, benzoic acid, and benzyl alcohol) were obtained. The four types of microcapsules were characterized using Fourier-transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscope (TEM), and thermogravimetric analysis (TGA), and their sustained release characteristics were evaluated. The optimal conditions were: CS dosage, 1.2 %; CS-to-eugenol mass ratio, 1:2; and CS-to-ALG mass ratio, 1:1. By comparing the IR spectra of the four types of microcapsules, wall material, and core material, the core materials were revealed to be encapsulated within the wall material. SEM results revealed that the granular protuberances on the surface of the microcapsules were closely aligned and persistent when magnified 2000×. The TEM results indicated that all four microcapsules had a spherical and bilayer structure. The thermal stability and sustained release results showed that the four microcapsules were more resilient and less volatile than the four core materials. The release conformed to first-order kinetics, and the release ratios of the four microcapsules were as follows: benzyl alcohol microcapsules ˃ eugenol microcapsules ˃ cinnamaldehyde microcapsules ˃ benzoic acid microcapsules. The prepared bilayer microcapsules encapsulated four different core materials with good sustained release properties., Competing Interests: Declaration of competing interest The authors report no declarations of interest., (Copyright © 2024 Elsevier B.V. All rights reserved.)

In this work, two neolignans - dehydrodieugenol (1) and dehydrodieugenol B (2) - were isolated from leaves of Ocotea cymbarum (H. B. K.) Ness. (Lauraceae). When tested against two human breast cancer cell lines (MCF7 and MDA-MB-231), compound 1 was inactive (IC 50  > 500 μM) whereas compound 2 displayed IC 50 values of 169 and 174 μM, respectively. To evaluate, for the first time in the literature, the synergic cytotoxic effects of compounds 1 and 2 with ion Cu 2+ , both cell lines were incubated with equimolar solutions of these neolignans and Cu(ClO 4 ) 2 ·6H 2 O. Obtained results revealed no differences in cytotoxicity upon the co-administration of compound 2 and Cu 2+ . However, the combination of compound 1 and Cu 2+ increases the cytotoxicity against MCF7 and MDA-MB-231 cells, with IC 50 values of 165 and 204 μM, respectively. The activity of compound 1 and Cu 2+ in MCF7 spheroids regarding the causes/effects considering the tumoral microenvironment were accessed using fluorescence staining and imaging by fluorescence microscopy. This analysis enabled the observation of a higher red filter fluorescence intensity in the quiescence zone and the necrotic core, indicating a greater presence of dead cells, suggesting that the combination permeates the spheroid. Finally, using ICP-MS analysis, the intracellular copper disbalance caused by mixing compound 1 and Cu 2+ was determined quantitatively. The findings showcased a 50-fold surge in the concentration of Cu 2+ compared with untreated cells (p > 0.0001) - 18.7 ng of Cu 2+ /mg of proteins and 0.37 ng of Cu 2+ /mg of protein, respectively. Conversely, the concentration of Cu 2+ in cells treated with compound 1 was similar to values of the negative control group (0.29 ng of Cu 2+ /mg of protein). This alteration allowed us to infer that compound 1 combined with Cu 2+ induces cell death through copper homeostasis dysregulation., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Eugenol (Eug) holds potential as a treatment for bacterial rhinosinusitis by nasal powder drug delivery. To stabilization and solidification of volatile Eug, herein, nasal inhalable γ-cyclodextrin metal-organic framework (γ-CD-MOF) was investigated as a carrier by gas-solid adsorption method. The results showed that the particle size of Eug loaded by γ-CD-MOF (Eug@γ-CD-MOF) distributed in the range of 10-150 μm well. In comparison to γ-CD and β-CD-MOF, γ-CD-MOF has higher thermal stability to Eug. And the intermolecular interactions between Eug and the carriers were verified by characterizations and molecular docking. Based on the bionic human nasal cavity model, Eug@γ-CD-MOF had a high deposition distribution (90.07 ± 1.58%). Compared with free Eug, the retention time Eug@γ-CD-MOF in the nasal cavity was prolonged from 5 min to 60 min. In addition, the cell viability showed that Eug@γ-CD-MOF (Eug content range 3.125-200 µg/mL) was non-cytotoxic. And the encapsulation of γ-CD-MOF could not reduce the bacteriostatic effect of Eug. Therefore, the biocompatible γ-CD-MOF could be a potential and valuable carrier for nasal drug delivery to realize solidification and nasal therapeutic effects of volatile oils., (© 2024. The Author(s), under exclusive licence to American Association of Pharmaceutical Scientists.)

Methyleugenol is one of the main active constituents in the volatile oil of the traditional Chinese medicine Asari Radix et Rhizoma. It possesses various pharmacological effects such as analgesic, anesthetic, and anti-inflammatory properties. In biosynthesis, the initial precursor phenylalanine is finally converted into methyleugenol through a series of intermediate compounds including coniferyl acid, courmaryl acid, caffeic acid, ferulic acid/ferulic-CoA, coniferyl aldehyde, conferyl alcohol, cnfiferyl acetate, and eugenol/isoeugenol, which are produced through catalysis of a large number of enzymes. Eugenol O-methyltransferase(EOMT) is one of the key enzymes in the biosynthesis pathway, capable of methylating eugenol on the para-site hydroxyl group of the benzene ring, thereby generating methyleugenol. Here, an(iso)eugenol O-methyltransferase(IEMT) gene was cloned for the first time from Asarum siebo-ldii, holding an open reading frame that consisted of 1 113 bp and encoded a protein containing 370 amino acid residues. Bioinformatics analysis results showed that this protein was equipped with the characteristic structural domains of methyltransferases such as S-adenosylmethionine(SAM) binding sites and dimerization domains. The prokaryotic expression recombinant plasmid pET28a(+)-AsIEMT was constructed, and the candidate protein was induced and purified. In vitro enzyme assays confirmed that AsIEMT had dual functions. The enzyme could catalyze the production either of methyleugenol from eugenol or of methylisoeugenol from isoeugenol, although the latter was more prevalent. When isoeugenol was used as the substrate, the kinetics parameters K&#95;m and V&#95;(max) of catalytic reaction were(0.90±0.06) mmol·L~(-1) and(1.32±0.04)nmol·s~(-1)·mg~(-1), respectively. This study expanded our understandings of critical enzyme genes involved in phenylpropanoid metabolic pathways, and would facilitate the elucidation of quality formation mechanisms of the TCM Asari Radix et Rhizoma.

Konjac glucomannan (KGM) is becoming a very potential food packaging material due to its good film-forming properties and stability. However, KGM film has several shortcomings such as low mechanical strength, strong water absorption, and poor self-antibacterial performance, which limits its application. Therefore, in order to enhance the mechanical and functional properties of KGM film, this study prepared Pickering nanoemulsion loaded with eugenol and added it to the KGM matrix to explore the improvement effect of Pickering nanoemulsion on KGM film properties. Compared to pure KGM film and eugenol directly added film, the mechanical strength of Pickering-KGM film was significantly improved due to the establishment of ample hydrogen bonding interactions between the β-cyclodextrin inclusion complex system and KGM. Pickering-KGM film had significant antioxidant capacity than pure KGM film and eugenol directly added KGM film (eugenol-KGM film) (~3.21 times better than KGM film, ~0.51 times better than eugenol-KGM film). In terms of antibacterial activity, Pickering-KGM film had good inhibitory effect on Escherichia coli, Staphylococcus aureus, and Candida albicans, and raspberry preservation experiment showed that the shelf life of the Pickering-KGM film could be extended to about 6 days. To sum up, this study developed a novel means to improve the film performance and provide a new insight for the development and application of food packaging film., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

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.

Size and monodispersity of solid particles are essential to their structuring behaviors at biphasic interfaces. However, delicate control over biomolecular nanoparticle sizes is challenging. In this study, we prepared monodisperse rice protein (RP) nanoparticles by neutralizing RP solutions (pH 12.0) using combined treatments of cationic exchange resins (CERs) and HCl. CERs absorbed Na + by releasing H + without producing salt during neutralization. By compromising the usages of CERs and HCl when preparing RPs, the generation of NaCl can be delicately tailored, leading to controllable nanoparticle sizes from 20 nm to 30 nm. By mixing these nanoparticles with eugenol in an aqueous solution, the nanoparticles accommodated eugenol in their cores due to inward diffusion. Furthermore, such eugenol-contained nanoparticles with different sizes demonstrated tunable releases of eugenol due to size-dependent capillary forces, which can be harnessed for suppression of microbial growth on fruit with prolonged effective eugenol concentration., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

This study evaluates the pediculicidal activity of nanoformulations containing different binary essential oil component mixtures (eugenol:linalool, 1,8 -cineole:linalool, and eugenol:thymol) using immersion bioassays. These have allowed us to evaluate the knockdown time affecting 50% of the individuals (KT 50 ). In addition, the type of interaction between the components in each mixture was established in terms of the combination index (IC). The KT 50 values were 6.07; 8.83; 7.17 and 27.23 h for linalool, 1,8 -cineole, eugenol, and thymol, respectively. For the eugenol:linalool mixtures, the efficacy was lower or equal to that obtained for the nanoformulations of the pure compounds, with values of KT 50 about 13.33, 8.16 and 6.71 h for mixtures with ratios 3:1, 1:1 and 1:3, respectively. These mixtures present IC > 1, evidencing antagonistic interaction, which is enhanced with eugenol content. In the case of the binary mixtures of 1,8 -cineole: linalool, KT 50 values were similar to those obtained for eugenol:linalool mixtures with similar ratios. In this case, IC assumes values close to unity, suggesting additive interactions independently of the mixture composition. On the other side, mixtures of eugenol:thymol with 1:1 and 1:3 ratios showed values of 9.40 and 32.93 h, while the mixture with a 3:1 ratio showed the greatest effectiveness (KT 50 of 4.42 h). Eugenol:thymol mixtures show synergistic interaction (IC < 1) for combinations 3:1 and 1:1, while no interaction was observed for 1:3 combination. This indicates that eugenol enhances thymol activity. These results must be considered an important step forward to the development of effective pediculicidal nanoformulations based on botanical compounds., (Copyright © 2024 Elsevier Inc. All rights reserved.)

Background: Eugenol exhibits broad-spectrum antibacterial and anti-inflammatory properties. However, cytotoxicity at high concentrations limits the full utilization of eugenol-based drug complexes. Formulations of multidrug-loaded eugenol-based nanoemulsions have reduced cytotoxicity; however, it remains crucial to understand how these eugenol complexes interact with primary human carrier proteins to design and develop therapeutic alternatives. Consequently, this study primarily aims to investigate the impact on Human Serum Albumin (HSA) when it interacts with eugenol-based complexes loaded with first-line anti-tuberculosis drugs., Methods: This study used various spectroscopic such as UV-visible spectroscopy, Fluorescence spectroscopy, Fourier-transform infrared spectroscopy and computational methods such as molecular docking and 100 ns molecular simulation to understand the impact of eugenol-based first-line anti-tuberculosis drug-loaded nanoemulsions on HSA structure., Results: The binding of the HSA protein and eugenol-based complexes was studied using UV-visible spectroscopic analysis. Minor changes in the fluorophores of the protein further confirmed binding upon interaction with the complexes. The Fourier-transform infrared spectra showed no significant changes in protein structure upon interaction with eugenol-based multidrug-loaded nanoemulsions, suggesting that this complex is safe for internal administration. Unlike eugenol or first-line anti-tuberculosis alone, molecular docking revealed the strength of the binding interactions between the complexes and the protein through hydrogen bonds. The docked complexes were subjected to a 100 ns molecular dynamics simulation, which strongly supported the conclusion that the structure and stability of the protein were not compromised by the interaction., Conclusions: From the results we could comprehend that the eugenol (EUG)-drug complex showed greater stability in HSA protein structure when compared to HSA interacting with isoniazid (INH), rifampicin (RIF), pyrazinamide (PYR), or ethambutol (ETH) alone or with EUG alone. Thus, inferring the potential of EUG-based drug-loaded formulations for a safer and efficient therapeutic use.

Pathogens and pests pose significant threats to global crop productivity and plant immunity, necessitating urgent measures from researchers to prevent pathogen contamination and pest damage to crops. A natural plant-based antibacterial agent, eugenol (EUG), has demonstrated excellent antimicrobial and insect repellent capabilities, but the characteristics of volatilization and poor dissolution limit the practical application. The nanoization of pesticide formulations holds promise in the development of highly effective pesticides for antibacterial and insecticidal purposes. Herein, a eugenol-loaded nano delivery system (EUG@CMC-PGMA-CS) was synthesized using glycidyl methacrylate (GMA) as a functional monomer to connect carrier core structure carboxymethyl cellulose (CMC) with shell structure chitosan (CS), and EUG was encapsulated within the carrier. EUG@CMC-PGMA-CS demonstrated excellent leaf affinity, with minimum contact angles (CAs) of 37.83 and 70.52° on hydrophilic and hydrophobic vegetable leaf surfaces, respectively. Moreover, the maximum liquid holding capacity (LHC) of EUG@CMC-PGMA-CS on both hydrophilic and hydrophobic vegetable leaf surfaces demonstrates a noteworthy 55.24% enhancement compared to the LHC of pure EUG. The in vitro release curve of EUG@CMC-PGMA-CS exhibited an initial burst followed by stable sustained release. It is with satisfaction that the nano delivery system demonstrated exceptional antibacterial properties against S. aureus and satisfactory insecticidal efficacy against Spodoptera litura . The development of this eugenol-loaded nano delivery system holds significant potential for enhanced antibacterial and insect repellents in agriculture, paving the way for the application of volatile bioactive substances.

Bacterial infections are a big challenge in clinical treatment, making it urgent to develop innovative antibacterial systems and therapies to combat bacterial infections. In this study, we developed a novel MOF-based synergistic antibacterial system (Eu@B-UiO-66/Zn) by loading a natural antibacterial substance (eugenol) with hierarchically porous MOF B-UiO-66 as a carrier and further complexing it with divalent zinc ions. Results indicate that the system achieved a controlled release of eugenol under pH responsive stimulation, with the complexation ability of eugenol and Zn 2+ ions as a switch. Due to the destruction of a coordination bond between eugenol and Zn 2+ ions by an acidic medium, the release of eugenol loaded in Eu@B-UiO-66/Zn reached 80% at pH 5.8, which was significantly higher than that under pH 8.0 (51%). Moreover, the inhibitory effect of Eu@B-UiO-66/Zn against Escherichia coli ( E. coli ) and Staphylococcus aureus ( S. aureus ) after 24 h was 96.4% and 99.7%, respectively, owing to the synergistic antibacterial effect of eugenol and Zn 2+ ions, which was significantly stronger than free eugenol and Eu@B-UiO-66. We hope that this strategy for constructing responsive MOF-based antibacterial carriers could have potential possibilities for the application of MOF materials in antibacterial fields.

The active biological phytochemicals, crucial compounds employed in creating hundreds of medications, are derived from valuable and medicinally significant plants. These phytochemicals offer excellent protection from various illnesses, including inflammatory disorders and chronic conditions caused by oxidative stress. A phenolic monoterpenoid known as eugenol (EUG), it is typically found in the essential oils of many plant species from the Myristicaceae, Myrtaceae, Lamiaceae, and Lauraceae families. One of the main ingredients of clove oil (Syzygium aromaticum (L.), Myrtaceae), it has several applications in industry, including flavoring food, pharmaceutics, dentistry, agriculture, and cosmeceuticals. Due to its excellent potential for avoiding many chronic illnesses, it has lately attracted attention. EUG has been classified as a nonmutant, generally acknowledged as a safe (GRAS) chemical by the World Health Organization (WHO). According to the existing research, EUG possesses notable anti-inflammatory, antioxidant, analgesic, antibacterial, antispasmodic, and apoptosis-promoting properties, which have lately gained attention for its ability to control chronic inflammation, oxidative stress, and mitochondrial malfunction and dramatically impact human wellness. The purpose of this review is to evaluate the scientific evidence from the most significant research studies that have been published regarding the protective role and detoxifying effects of EUG against a wide range of toxins, including biological and chemical toxins, as well as different drugs and pesticides that produce a variety of toxicities, throughout view of the possible advantages of EUG., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

The ultrasonically processed Eugenol (EU) and Carvacrol (CAR) nanoemulsions (NE) were successfully optimized via response surface methodology (RSM) to achieve broad spectrum antimicrobial efficacy. These NE were prepared using 2 % (w/w) purity gum ultra (i.e., succinylated starch), 10 % (v/v) oil phase, 80 % (800 W) sonication power, and 10 min of processing time as determined via RSM. The second order Polynomial method was suitable to RSM with a co-efficient of determination >0.90 and a narrow polydispersity index (PDI) ranging 0.12-0.19. NE had small droplet sizes (135.5-160 nm) and low volatility at high temperatures. The EU & CAR entrapment and heat stability (300 °C) confirmed by Fourier transform infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA). Further, the volatility of EU & CAR NE was 18.18 ± 0.13 % and 12.29 ± 0.11 % respectively, being lower than that of bulk/unencapsulated EU & CAR (i.e., 23.48 ± 0.38 % and 19.11 ± 0.08 %) after 2 h at 90 °C. Interestingly, both EU & CAR NE showed sustained release behaviour till 48 h. Their digest could inhibit Salmonella typhimurium (S. typhimurium) via membrane disruption and access to cellular machinery as evident from SEM images. Furthermore, in-vivo bio-accessibility of EU & CAR in mice serum was up to 80 %. These cost-effective and short-processed EU/CAR NE have the potential as green preservatives for food industry., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Exploring the natural, safe, and effective antimicrobial is one of the preferable ways to control foodborne bacteria. In this work, novel oil-in-water nanoemulsions were formulated with sophorolipids and eugenol without any co-surfactant using a self-assembling strategy. These nanoemulsions showed high stability with sizes less than 200 nm when exposure to low concentrations of salt ions, various pH values (5.0, 7.0, 10.0), storage temperature and time. The synergistic antibacterial effects against both Gram-negative Escherichia coli and Gram-positive Bacillus cereus were determined with a minimum inhibitory concentration (MIC) value of 0.5 mg/mL and 0.125 mg/mL, respectively. Further microscopy (SEM, TEM, LCSM) examination and ATP/Na + -K + -ATPase assay results showed that the morphological changes, intensive cell membrane permeability, leakage of ATP, and decreased Na + -K + -ATPase contributed to the antibacterial effects. Moreover, the bonding mechanism between nanoemulsions and cell membranes were further evaluated by FTIR and ITC using a DPPC vesicle model, which demonstrated that the nanoemulsions adsorbed on the surface of bilayer, interacted with the hydrophobic chains of DPPC membrane mainly through the hydrophobic interaction, and altered the structural integrity of the lipid bilayer. These results not only provide a facile green strategy for fabricating stable nanoemulsions, but also highlight a new perspective for stabilizing essential oils for their widely application in food industry., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Eugenol, a natural compound found in essential oils such as clove oil, has been extensively studied for its diverse biological activities including the therapeutic potential against microbial and parasitic infections. This review provides an overview of the synthetic strategies (shown in Supplementary Material) employed to develop bioactive derivatives and analogues derived from eugenol and related compounds (e.g., dihydroeugenol and isoeugenol), focusing on biological activity of more than 100 bioactive eugenol derivatives against bacterial, fungal, viral and protozoal pathogens. Through a comprehensive survey of literature, this paper shows the impact of structural modifications of these phenylpropanoids on antimicrobial and antiparasitic activity. Key findings highlight promising candidates for further development in antimicrobial drug discovery, suggesting directions for future research in the pursuit of effective therapeutic agents.

Aim: The design, synthesis, docking studies and evaluation of the in vitro antifungal and cytotoxic properties of eugenol (EUG) containing 1,2,3-triazole derivatives are reported. Most of the derivatives have not been reported. Materials & methods: The EUG derivatives were synthesized, molecular docked and tested for their antifungal activity. Results: The compounds showed potent antifungal activity against Trichophyton rubrum , associated with dermatophytosis. Compounds 2a and 2i exhibited promising results, with 2a being four-times more potent than EUG. The binding mode prediction was similar to itraconazole in the lanosterol-14-α-demethylase wild-type and G73E mutant binding sites. Additionally, the pharmacokinetic profile prediction suggests good gastrointestinal absorption and potential oral administration. Conclusion: Compound 2a is a promising antifungal agent against dermatophytosis caused by T. rubrum .

To evaluate the bactericidal action of antimicrobial peptide CF-14, Eugenol (EU) and carvacrol (CAR) nanoparticles (NPs) less than 200 nm were surface-modified with CF14, gaining approximately 200 nm of EU-CF and CAR-CF NPs with swollen morphology. EU-CF and CAR-CF NPs were bactericidal to E. coli at dosage of 0.09% and 0.07% (v/v), respectively; while they were just bacteriostatic to Staphylococcus aureus at 0.10% and 0.08% (v/v). Spectral variations in bacterial carbohydrates (1185-900 cm -1 ), lipids (3000-2800 cm -1 ) and DNA (1500-1185 cm -1 ) were obvious as evident from Fourier transform infrared spectroscopy (FTIR). A higher percentage of membrane damaged (non-revivable) E. coli than S. aureus was found, which indicated electrostatic interactions between Gram-negative E. coli with cationic CF conjugated NPs leading to DNA disintegration. Interestingly, EU-CF and CAR-CF NPs inhibited E. coli growth in orange juice without impacting flavour compounds., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

In northern China, clove is a common plant. Its extracted eugenol exhibits a variety of biological properties, including antioxidant and antibacterial effects. This study looked at eugenol's antioxidant potential and its impact on the flora in the intestinal tract of humans. Eugenol's ability to scavenge superoxide anions and 2,2-biphenyl-1-picrylhydrazyl (DPPH) radicals, as well as its impact on the growth of common intestinal bacteria Lactobacillus and Escherichia coli, were studied at various eugenol concentrations. The results showed that different optimal antioxidant concentrations of eugenol existed for different free radicals, and the optimal antioxidant concentrations for DPPH and superoxide anion were 0.16 μL/mL and 0.04 μL/mL, respectively. Low concentrations of eugenol had no significant inhibitory effect on Lactobacillus but a significant inhibitory effect on E. coli. This research is anticipated to offer a theoretical reference for the use of eugenol in specialized dietary food applications.

This work describes the design, synthesis and antifungal activity of new imidazoles and 1,2,4-triazoles derived from eugenol and dihydroeugenol. These new compounds were fully characterized by spectroscopy/spectrometric analyses and the imidazoles 9, 10, 13 e 14 showed relevant antifungal activity against Candida sp. and Cryptococcus gattii in the range of 4.6-75.3 μM. Although no compound has shown a broad spectrum of antifungal activity against all evaluated strains, some azoles were more active than either reference drugs employed against specific strains. Eugenol-imidazole 13 was the most promising azole (MIC: 4.6 μM) against Candida albicans being 32 times more potent than miconazole (MIC: 150.2 μM) with no relevant cytotoxicity (selectivity index >28). Notably, dihydroeugenol-imidazole 14 was twice as potent (MIC: 36.4 μM) as miconazole (MIC: 74.9 μM) and more than 5 times more active than fluconazole (MIC: 209.0 μM) against alarming multi-resistant Candida auris. Furthermore, in vitro assays showed that most active compounds 10 and 13 altered the fungal ergosterol biosynthesis, reducing its content as fluconazole does, suggesting the enzyme lanosterol 14α-demethylase (CYP51) as a possible target for these new compounds. Docking studies with CYP51 revealed an interaction between the imidazole ring of the active substances with the heme group, as well as insertion of the chlorinated ring into a hydrophobic cavity at the binding site, consistent with the behavior observed with control drugs miconazole and fluconazole. The increase of azoles-resistant isolates of Candida species and the impact that C. auris has had on hospitals around the world reinforces the importance of discovery of azoles 9, 10, 13 e 14 as new bioactive compounds for further chemical optimization to afford new clinically antifungal agents., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Masson SAS. All rights reserved.)

Clove bud is a medicinal plant used traditionally in Asia for the treatment of various disease. Previously, Clove oil is a potential source of an antimicrobial compounds especially vis-a-vis bacterial pathogens. However, the compound responsible for this activity remains to be investigated. Essential oil (EO) clove, acetylated essential oil clove, eugenol, and acetyleugenol were evaluate as an antibacterial potential agent against Staphyloccocus aureus (SE), Escherichia coli (EC) and Pseudomonas aeruginosa (PA). Essential oil containing eugenol was extracted from buds of Eugenia caryophyllata commonly named clove (Syzygium aromaticum (L.) (Family Myrtaceae) by a simple hydrodistillation. The analysis of the essential oils (EOs) using gas chromatography-mass spectrometry (GC-MS) shows eugenol as the major constituent with 70.14 % of the total. The Eugenol was isolated from the EO using chemical treatment. Afterwards, the EO and eugenol were converted to acetylated EO and acetyleugenol, respectively using acetic anhydride. The antibacterial result revealed that all compounds showed a strong activity against the three strains. The Staphyloccocus aureus and Pseudomonas aeruginosa were extremely sensitive against eugenol with an inhibition diameters of 25 mm. The MIC values of eugenol versus S. aureus and P. aeruginosa were 0.58 and 2.32 mg/mL, respectively, while the MIB values were 2.32 mg/mL and 9.28 mg/mL., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Viral infections are spread all around the world. Although there are available therapies, their safety and effectiveness are constrained by their adverse effects and drug resistance. Therefore, new natural antivirals have been used such as essential oils, which are natural products with promising biological activity. Accordingly, the present study aimed to identify the components of clove ( Syzygium aromaticum ) essential oil (EOCa) and verify its antioxidant and antiviral activity. The oil was analyzed using GC/MS, and the antioxidant capacity was evaluated as a function of the radical scavenging activity. A plaque reduction test was used to measure the antiviral activity against herpes simplex virus (HSV-1), hepatitis A virus (HAV), and an adenovirus. GC/MS analysis confirmed the presence of eugenol as the main component (76.78%). Moreover, EOCa had powerful antioxidant activity with an IC 50 of 50 µg/mL. The highest antiviral potential was found against HAV, with a selectivity index (SI) of 14.46, while showing poor selectivity toward HSV-1 with an SI value of 1.44. However, no relevant effect was detected against the adenovirus. The antiviral activity against HAV revealed that its effect was not related to host cytotoxicity. The findings imply that EOCa can be utilized to treat diseases caused by infections and free radicals.

This work aimed to investigate the encapsulation and stabilization mechanism of cinnamaldehyde and eugenol in high internal phase Pickering emulsions (HIPPEs) through regulating their interfacial rheological properties and interfacial microstructure. With the incorporation of cinnamaldehyde, the Schiff base reaction between the cinnamaldehyde and proteins favored the formation of the predominantly elastic and solid-like interfacial layers. In contrast, the hydrogen bonds between eugenol and proteins resulted in the transformation of interfacial layers to viscous dominant with weak viscoelastic responses. Thus, cinnamaldehyde-loaded HIPPEs had a better storage stability than eugenol-loaded HIPPEs, and the retention rate was increased by about 15 %∼20 %. The addition of tea camellia seed oil inhibited the mobility of immobilized water and improved the retention rates of cinnamaldehyde and eugenol by approximately 6 % and 12 % (30 days at 25 °C), respectively. These findings will be beneficial for the development and design of effective essential oil encapsulation systems in the food industry., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)

Natural value-added compounds produced from biological sources have attained immense significance in medicinal, food, flavourings, and agrochemical industries. Further, biotransformation is a powerful tool used to produce value-added compounds cost-effectively and selectively. In the present study, biotransformation of eugenol using an endophytic fungus Daldinia sp. IIIMF4010 isolated from the fresh leaves of the plant Rosmarinus officinalis leads to the production of two known value-added compounds. The biotransformation reaction of eugenol (50 mM) resulted in the production of eugenol- β -D-glucopyranoside (6.2%) and vanillin (21.8%). These biotransformed products were further characterized by liquid chromatography-mass spectroscopy (LC-MS) and nuclear magnetic resonance (NMR).

Colorectal cancer is a type of cancer encountered worldwide and ranks third among all cancer types in terms of incidence. Polyphenols have been shown to have a wide range of biological functions, including a significant impact on cancer start, development, and promotion through regulating many signaling pathways. The aim of this study was to investigate the anticancer effects of isoeugenol based compounds 1, 2 on HT29 colorectal cancer cell line in vitro. MTT test and scratch assay were carried out to determine the effect of these compounds on HT29 cell proliferation and migration respectively. In addition, mRNA expression levels of apoptosis and metastasis-related genes (p53, Bcl2, Bax, Caspase 3, Caspase7, Caspase8, Caspase9, HIF1-α, VEGF, MMP-2, MMP-9) were examined by quantitative real-time PCR. The results indicated that 1 and 2 inhibited HT29 cell proliferation and induced apoptosis by increasing the Bax/Bcl2 ratio and Caspase-9 and Caspase-3 mRNA expression. In conclusion, the results of this study showed that the treatment of these compounds significantly suppressed the mRNA expressions of metastasis-related genes such as Matrix Metalloproteinase-2, Matrix Metalloproteinase-9, Vascular Endothelial Growth Factor and Hypoxia‑Inducible Factor 1α., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Inc. All rights reserved.)

Mucormycosis, also known as Zygomycosis, is a disease caused by invasive fungi, predominantly Rhizopus species belonging to the Order of Mucorales. Seeing from the chemistry perspective, heterocyclic compounds with an "azole" moiety are widely employed as antifungal agent for minimising the effect of mucormycosis as a prescribed treatment. These azoles serve as non-competitive inhibitors of fungal CYP51B by predominantly binding to its heme moiety, rendering its inhibition. However, long-term usage and abuse of azoles as antifungal medicines has resulted in drug resistance among certain fungal pathogens. Hence, there is an unmet need to find alternative therapeutic compounds. In present study, we used various in vitro tests to investigate the antifungal activity of eugenol against R. oryzae/R. arrhizus, including ergosterol quantification to test inhibition of ergosterol production mediated antifungal action. The minimum inhibitory concentration (MIC) value obtained for eugenol was 512 μg/ml with reduced ergosterol concentration of 77.11 ± 3.25% at MIC/2 concentration. Further, the molecular interactions of eugenol with fungal CYP51B were meticulously studied making use of proteomics in silico study including molecular docking and molecular dynamics simulations that showed eugenol to be strongly interacting with heme in an identical fashion to that shown by azole drugs (in this case, clotrimazole was evaluated). This is the first of a kind study showing the simulation study of eugenol with CYP51B of fungi. This inhibition results in ergosterol synthesis and is also studied and compared with keeping clotrimazole as a reference., (© 2022. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)

Ergosterol is the key sterol component in the cell membrane of fungi including moulds and yeasts. Any decrease in the levels of ergosterol in the cell membrane of fungi render them venerable to cell membrane damage and even its death. Majority of antifungal drug targets the key enzymes involved in ergosterol biosynthesis pathway. The biochemical pathway for the synthesis of Ergosterol is a complex one, though the reactions carried by Squalene Epoxidase (SE) and 14α-demethylase (CYP51- a member of Cytochrome P450 family) serves to the key rate limiting reactions that can impact the overall production of Ergosterol. Allylamines class of antifungal drug target SE while Azoles target the CYP51. Currently advancement in the drug development is focused to introduce newer drugs that can simultaneously inhibit both this rate limiting enzymes. However, natural compounds established to possess antifungal activity but the major loophole about their understanding lies in the fact that their mode of action are severely unstudied. One such well-established antifungal natural phytochemical is Eugenol, and in current manuscript we investigated its efficacy to interact with both, SE and CYP51 of Candida albicans using molecular Docking, Free energy change calculations and Molecular Dynamics (MD) simulation, showing promising outcomes. For experimental studies, terbinafine, clotrimazole and eugenol showed 4 μg/ml, 2 μg/ml, and 512 μg/ml MIC 90 values, respectively against C. albicans and also showed reduction in Ergosterol production at sub-MIC levels. The obtained result indicates the involvement of eugenol in the inhibition of enzymes require in the ergosterol biosynthesis pathway., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)

The oriental fruit fly (Bactrocera dorsalis) is a devastating fruit pest that infests more than 450 plant species. Methyl eugenol (ME) has been used as male attractant to monitor and eradicate B. dorsalis populations for 70 years, but the molecular basis of its activity remains largely unclear. Previously, BdorOBP83b and BdorOBP56f-2 as odorant binding proteins (OBPs) were identified responsible for ME perception. In this study, ME-induced expression profiles and in vitro binding assays revealed that BdorOBP69a is also produced in response to ME and binds directly to it with strong affinity (K d  = 9.54 μM). BdorOBP69a -/- null mutants generated by CRISPR/Cas9 mutagenesis showed significantly lower electroantennogram and behavioral responses to ME than wild-type controls. Molecular docking analysis followed by site-directed mutagenesis showed that residues Leu89 and Phe145 are essential for the interaction between BdorOBP69a and ME. BdorOBP69a is therefore an important component involved in the perception of ME in B. dorsalis and a promising molecular target for the development of new male attractants. The molecular docking and binding assay data also provide an important reference for future OBP gene manipulation and ME chemical engineering to improve the efficiency of male attractants., (Copyright © 2022 Elsevier Ltd. All rights reserved.)

The clove (Syzygium aromaticum) is an important tropical spice crop in global trade. Evolving environmental pressures necessitate modern characterization and selection techniques that are currently inaccessible to clove growers owing to the scarcity of genomic and genetic information. Here, we present a 370-Mb high-quality chromosome-scale genome assembly for clove. Comparative genomic analysis between S. aromaticum and Eucalyptus grandis-both species of the Myrtaceae family-reveals good genome structure conservation and intrachromosomal rearrangements on seven of the eleven chromosomes. We report genes that belong to families involved in the biosynthesis of eugenol, the major bioactive component of clove products. On the basis of our transcriptomic and metabolomic findings, we propose a hypothetical scenario in which eugenol acetate plays a key role in high eugenol accumulation in clove leaves and buds. The clove genome is a new contribution to omics resources for the Myrtaceae family and an important tool for clove research., (© 2022. The Author(s).)

The current status of controversy regarding the use of certain preservatives in cosmetic products makes it necessary to seek new ecological alternatives that are free of adverse effects on users. In our study, two different natural terpenes Carvacrol and Eugenol were encapsulated in chitosan nanoparticles in different ratios of Chitosan:terpene. The nanoparticles were characterized by DLS and TEM showing a maximum particle size of 100 nm. The chemical structure, thermal properties, and release profile of terpenes were evaluated showing a successful protection of terpene in Chitosan matrix. Two different release profile were observed showing a faster release profile in the case of Eugenol. Antimicrobial properties of nanoparticles were evaluated against typical microbial contaminants found in cosmetic products, showing higher antimicrobial properties with chitosan encapsulation of terpenes. Furthermore, natural moisturizing cream inoculated with beforementioned microorganisms was formulated with Carvacrol-chitosan nanoparticles and Eugenol-chitosan nanoparticles to evaluate the preservative efficiency, indicating a highest preservative efficiency with the use of Eugenol-chitosan nanoparticles., (Copyright © 2022 Elsevier B.V. All rights reserved.)

This work investigated the antioxidant potential of acetylated and nitrated eugenol derivatives through structural analysis and the mechanism of hydrogen atomic transfer (HAT) by density functional theory (DFT). The structures were optimized by the hybrid functional M06-2X with basis set 6-31 + G(d,p), and the HAT mechanism was evaluated with HO, HOO, CH 3 O, DPPH radicals. In agreement with experimental data from previous studies, two steps of hydrogen transfer were tested. The thermodynamic data showed the need for two hydrogen atomic transfer steps from antioxidants, followed by the formation of p-quinomethanes (27, 28, and 29) to make the reaction spontaneous with DPPH. Furthermore, theoretical kinetic data showed that the preferred antioxidant site depends on the instability of the attacking radical and confirmed the antioxidant profile for eugenol (1, 4-allylbenzene-1,2-diol), and nitro-derivative 7 (5-allyl-3-nitrobenzene-1,2-diol) in the DPPH assay. Finally, this study showed that nitro compound 6 (4-allyl-2-methoxy-6-nitrophenol) also has anti-radical activity with smaller radicals but is not observed in the experiment due to structural characteristics and chemoselectivity of DPPH., (© 2022. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)

Ethnopharmacological Relevance: Tsantan Sumtang (TS), a traditional Tibetan medicine, has been used in the clinic for the treatment of myocardial ischemia (MI) for ages, however, the bioactive ingredients that are responsible for improving MI remain unknown., Aim of the Study: This study investigated the chemical components of TS and their medicinal efficacies at cell levels, in order to expound the bioactive ingredients in TS., Materials and Methods: First, a response-surface methodology was employed to determine the optimum ethanol reflux extraction process of polyphenols in TS (PTS) due to their close correlation with MI improvement. Second, a serum pharmacochemistry technique was used to analyze the compounds of PTS absorbed into the blood of rats. Third, hypoxia-, H 2 O 2 -, and adriamycin (ADM)-induced H9c2 cell injury models were used to investigate the cardioprotective effects of these compounds in vitro. Fourth, protective effects of isovitexin, quercitrin, and isoeugenol on mitochondrial function were further tested., Results: The optimum extraction conditions for obtaining PTS were an ethanol concentration of 78.22%, an extraction time of 67.4 min, and a material-liquid ratio of 1:72.60 mL/g. Serum pharmacochemistry analysis detected 21 compounds, of which 11 compounds were always present in the blood within 5 h. Cytotoxicity and the protective effect of 11 compounds in hypoxia-, H 2 O 2 -, and ADM-induced H9c2 cell injury models shown that isovitexin, quercitrin, and isoeugenol had almost no cytotoxicity, and they could elevate the survival rate in injured H9c2 cells. Furthermore, isovitexin, quercitrin, and isoeugenol could decrease mitochondrial reactive oxygen species (ROS) releasion, inhibite mitochondrial permeability transition pore (mPTP) opening, ameliorate the change of mitochondrial membrane potential (MMP) to exert mitochondrial protection effect., Conclusion: Isovitexin, quercitrin, and isoeugenol exhibited cardioprotective effect at cell levles, these three compounds might be the bioactive ingredients in TS. These findings elucidate the pharmacodynamic substances and mechanisms of TS, guiding its clinical use., (Copyright © 2021. Published by Elsevier B.V.)