Data-Independent Acquisition Proteome Technology for Analysis of Antifungal and Anti-aflatoxigenic Properties of Eugenol to Aspergillus flavus.

Several toxicogenic Aspergilli, such as Aspergillus flavus and A. parasiticus, could biosynthesize aflatoxin B1 (AFB1) and other mycotoxins. Chemical fungicides are commonly used to control fungal contamination, but chemical residues may pose significant risks to human health and environmental stability. Consequently, natural antifungal and aflatoxin-inhibiting agents could be sustainable alternatives. Eugenol has been used as an inhibitor of aflatoxins (AFs), which is a common essential oil. Nevertheless, the definite mechanism by which eugenol exerts its inhibitory effect on Aspergillus remains unclear. This research demonstrates that eugenol significantly suppressed fungi growth and AF production as the dose increased (40.9 to 100%). With the proteomics approach, the inhibition pathway of eugenol was investigated. The production of proteins involved in cell wall integrity was notably reduced under eugenol treatment, indicating that eugenol destroys the cell wall integrity of A. flavus. Furthermore, exposure to eugenol downregulated several fungal developmental regulators and subsequently inhibited A. flavus development. Energy metabolism in A. flavus is closely related to its secondary metabolism. Under eugenol treatment, the synthesis of proteins relevant to the pentose phosphate pathway was significantly enhanced, leading to a decrease in the availability of acetyl-CoA, a precursor for AF biosynthesis. Simultaneously, the valine, leucine, and isoleucine biosynthesis pathways were enhanced, further reducing the content of acetyl-CoA. This might be the primary factor in the inhibition of AF biosynthesis by eugenol. Ribosome biogenesis was the most dysregulated pathway based on KEGG data, indicating that eugenol disturbed ribosome biogenesis and affected its normal function in A. flavus. In conclusion, eugenol inhibits the cellular integrity, energy metabolism, and protein synthesis and then suppresses A. flavus development and AF biosynthesis, which provides a clearer grasp of the inhibitory mechanism meaningful for A. flavus and AF contamination control.

Hepatotoxicity Induced by Methyl Eugenol: Insights from Toxicokinetics, Metabolomics, and Gut Microbiota.

Due to continuous application as a flavoring agent in the pesticide, pharmaceutical, and food industries, methyl eugenol (ME) persists in the environment and causes deleterious impacts including cytotoxicity, genotoxicity, and liver damage. This study utilized a comprehensive approach, integrating toxicokinetics, metabolomics, and gut microbiota analysis, to explore the mechanisms behind ME-induced hepatotoxicity in mice. The study observed significant rises in ALT and AST levels, along with significant weight loss, indicating severe liver damage. Toxicokinetic data showed delayed Tmax and plasma accumulation after 28 days of repeated ME exposure at doses of 20 mg/kg, 40 mg/kg, and 60 mg/kg. The metabolomic analysis pinpointed four critical pathways-TCA cycle; alanine, aspartate, and glutamate metabolism; arginine biosynthesis; and tyrosine metabolism-linked to 20 potential biomarkers. Gut microbiota analysis revealed that extended ME exposure led to microbial imbalance, particularly altering the populations of Akkermansia, Prevotella, and Ruminococcus, which are key to amino acid metabolism and the TCA cycle, thus contributing to hepatotoxicity. However, the causal relationship between changes in gut microbiota and liver metabolite levels still requires further in-depth research. This study underscores the significant role of liver metabolites and gut microbiota in ME-induced liver damage.

Potential Involvement of Reactive Oxygen Species in the Bactericidal Activity of Eugenol against Salmonella Typhimurium.

There is an increasing need to develop alternative antimicrobials to replace currently used antibiotics. Phytochemicals, such as essential oils, have garnered significant attention in recent years as potential antimicrobials. However, the mechanisms underlying their bactericidal activities are not yet fully understood. In this study, we investigated the bactericidal activity of eugenol oil against Salmonella enterica serovar Typhimurium (S. Typhimurium) to elucidate its mechanism of action. We hypothesized that eugenol exerts its bactericidal effects through the production of reactive oxygen species (ROS), which ultimately leads to cell death. The result of this study demonstrated that the bactericidal activity of eugenol against S. Typhimurium was significantly (p < 0.05) mitigated by thiourea (ROS scavenger) or iron chelator 2,2'-dipyridyl, supporting the hypothesis. This finding contributes to a better understanding of the killing mechanism by eugenol oil.

Use of Natural Polymers for the Encapsulation of Eugenol by Spray Drying.

Background: Eugenol is a colourless or yellowish compound whose presence in clove essential oil surpasses the 75% of its composition. This phenylpropanoid, widely used as an antiseptic, anaesthetic and antioxidant, can be extracted by steam distillation from the dried flower buds of Syzygium aromaticum (L.). Due to its chemical instability in presence of light and air, it should be protected when developing a formulation to avoid or minimise its degradation. Methods: A promising approach would be encapsulation by spray drying, using natural coating products such as maltodextrin, gum arabic, and soy lecithin. To do so, a factorial design was carried out to evaluate the effect of five variables at two levels (inlet temperature, aspirator and flow rate, method of homogenisation of the emulsion and its eugenol:polymers ratio). Studied outcomes were yield and outlet temperature of the spray drying process, eugenol encapsulation efficiency, and particle size expressed as d(0.9). Results: The best three formulations were prepared by using a lower amount of eugenol than polymers (1:2 ratio), homogenised by Ultra-Turrax®, and pumped to the spray dryer at 35 m3/h. Inlet temperature and flow rate varied in the top three formulations, but their values in the best formulation (DF22) were 130 °C and 4.5 mL/min. These microcapsules encapsulated between 47.37% and 65.69% of eugenol and were spray-dried achieving more than a 57.20% of product recovery. Their size, ranged from 22.40 µm to 55.60 µm. Conclusions: Overall, the whole spray drying process was optimised, and biodegradable stable polymeric microcapsules containing eugenol were successfully prepared.

The Influence of Conditions of Polycondensation in Acid Medium on the Structure of Oligosilsesquioxanes with a Novel Eugenol-Containing Substituent.

Eugenol-containing oligoorganosilsesquioxanes were synthesized by the method of hydrolytic polycondensation in an active medium under various reaction conditions. The obtained products were characterized by 29Si NMR spectroscopy and MALDI-TOF spectrometry. It was shown that factors such as the reaction temperature, polycondensation duration, and molar ratio between the initial alkoxysilane monomer and acetic acid may affect the molecular weight characteristics and molecular structure of the formed oligomer, like the content of stressed cyclic units (T3, DTT, TDT) and unstressed silsesquioxane units TnDm. In particular, an increase in the ratio of the initial reagents led to an increase in the content of silsesquioxane Tn fragments from 28.2%mol to 41.7%mol, while the number of strained cyclic structures decreased by more than two times. An increase in the synthesis time is of no particular practical value since it was found that the composition of the oligomers synthesized for 6 h and 12 h was practically identical, as was that of the oligomers synthesized for 24 h and 48 h. A noticeable transition in the oligomer composition was observed only when the synthesis time was changed from 12 h to 24 h. Finally, it was shown that the choice of synthesis temperature had the strongest effect on the oligomer composition. The oligomer synthesized at 95 °C contained the highest amount of silsesquioxane Tn fragments, >77%mol, while a Tn fragment content of ~42%mol was observed during the synthesis at 117 °C. It was shown that silsesquioxanes are devitrified at room temperature (Tg from -6.4 to -10.6 °C), and their thermal stability in an inert atmosphere is 300 °C. The synthesized oligomers, due to the presence of hydroxyl-containing eugenol units, may be promising binders and additives for functional epoxy-silicone paints and coating materials.

The effects of diet and semiochemical exposure on male Bactrocera dorsalis (Hendel) (Diptera: Tephritidae) metabolic rate at a range of temperatures.

The oriental fruit fly, Bactrocera dorsalis (Hendel) (Diptera: Tephritidae), is an invasive species that has rapidly spread across the African continent, endangering the security of agricultural industries. The sterile insect technique (SIT) is being investigated as a viable additional pest management tool to suppress B. dorsalis populations after its successful implementation in other parts of the world. There is evidence to suggest that pre-release nutritional and semiochemical treatments for sterilised males can enhance their competitive performance against wild type males in SIT programs. This study examined how sterilisation, a diet rich in protein (addition of yeast hydrolysate) or containing semiochemicals (methyl eugenol or eugenol) affected the resting metabolic (RMR) of male B. dorsalis at different temperatures (15 - 30 °C), measured using flow-through respirometry. Our results indicated that the negative effect of sterilisation on RMR decreased as temperature increased and that duration of exposure to semiochemicals for 1 to 4 days was not a significant influencing factor on male B. dorsalis RMR. Protein-rich diet increased average RMR, but the difference in RMR between dietary groups decreased as temperature increased. Semiochemical feeding reduced the average RMR in male B. dorsalis. The difference in RMR between males that consumed semiochemical and those that did not increased with as temperature increased.

Eugenol transport and biosynthesis through grafting in aromatic plants of the Ocimum genus.

Aromatic compounds play essential roles in plant physiology and various industries because of their unique fragrances and beneficial properties. In this study, we investigated the transport and biosynthesis of eugenol, a prominent aromatic compound, within the Ocimum genus, using grafting experiments. Grafting sweet basil (Ocimum basilicum) scions onto diverse rootstocks, including tobacco (Nicotiana benthamiana) and thyme (Thymus vulgaris), revealed that eugenol is transported from the shoot to the root across distinct plant species. Furthermore, grafting within the Ocimum genus, which includes O. basilicum, O. tenuiflorum, and O. americanum, resulted in variations in eugenol transport and accumulation. The eugenol content in the shoots remained constant across all combinations, whereas the root eugenol levels varied depending on the scion-rootstock pair. To elucidate the biosynthetic capabilities of eugenol in Ocimum roots, we performed in vitro enzyme assays using crude protein extracts from roots, which revealed that eugenol can be synthesized in roots in addition to being transported. Expression analysis of eugenol synthase (EGSs) genes showed that EGS4 expression was influenced by grafting in O. basilicum roots, suggesting compensation by other EGSs. Our results suggest that eugenol transport and biosynthesis are multifaceted processes influenced by the interactions between different species and tissues. The potential to engineer eugenol levels in rootstocks lacking biosynthetic capacity has potential applications in agriculture and industry. This study reveals the dynamic interplay between eugenol transport and biosynthesis in the Ocimum genus, providing insights into the manipulation of aromatic compound production in plants.

Neuroprotective Potential of Eugenol in Polyglutamine-Mediated Neurodegenerative Disease Using Transgenic Drosophila Model.

Polyglutamine (PolyQ) diseases including Huntington's disease are devastating neurodegenerative disorders characterized by progressive neuronal loss and motor dysfunction. PolyQ pathology involves multiple cellular events and phytochemicals with multi-target mechanisms hold promise to treat these diseases with least side effects. One such promising phytochemical is Eugenol, which possesses antioxidant and anti-inflammatory properties, potentially targeting disrupted cellular pathways in PolyQ diseases. The present study investigated the effects of Eugenol on neurodegeneration and motor dysfunction in transgenic Drosophila models of PolyQ diseases. In this study, the robust pseudopupil assay was performed to analyze adult photoreceptor neuron degeneration, a marker of widespread degenerative events. Furthermore, the well-established crawling and climbing assays were conducted to evaluate progressive motor dysfunction in the PolyQ larvae and flies. This study found that Eugenol administration at disease onset or after progression reduced PolyQ disease phenotypes, particularly, neurodegeneration and motor dysfunction in a dose-dependent manner and with no side effects. Thus, this study suggests that Eugenol could be a viable candidate for developing treatments for PolyQ diseases, offering a multi-target approach with the potential for minimal or no side effects compared to conventional therapies.

Platelet Proteomics and Tissue Metabolomics Investigation for the Mechanism of Aspirin Eugenol Ester on Preventive Thrombosis Mechanism in a Rat Thrombosis Model.

Platelet activation is closely related to thrombosis. Aspirin eugenol ester (AEE) is a novel medicinal compound synthesized by esterifying aspirin with eugenol using the pro-drug principle. Pharmacological and pharmacodynamic experiments showed that AEE has excellent anti-inflammatory, antioxidant, and inhibitory platelet activation effects, preventing thrombosis. However, the regulatory network and action target of AEE in inhibiting platelet activation remain unknown. This study aimed to investigate the effects of AEE on platelets of thrombosed rats to reveal its regulatory mechanism via a multi-omics approach. The platelet proteomic results showed that 348 DEPs were identified in the AEE group compared with the model group, of which 87 were up- and 261 down-regulated. The pathways in this result were different from previous results, including mTOR signaling and ADP signaling at P2Y purinoceptor 12. The metabolomics of heart and abdominal aortic tissue results showed that the differential metabolites were mainly involved in steroid biosynthesis, the citric acid cycle, phenylalanine metabolism, phenylalanine, tyrosine, and tryptophan biosynthesis, and glutathione metabolism. Molecular docking results showed that AEE had a better binding force to both the COX-1 and P2Y12 protein. AEE could effectively inhibit platelet activation by inhibiting COX-1 protein and P2Y12 protein activity, thereby inhibiting platelet aggregation. Therefore, AEE can have a positive effect on inhibiting platelet activation.

In Vitro Anticancer Potential of Eugenol on Oral Cancer Cell Lines: A Systematic Review.

Oral cancer is one of the most common types of cancer and has become a global health concern. Oral squamous cell carcinoma (OSCC) is the most prevalent form of oral cancer worldwide. Eugenol, an aromatic phenolic compound, exhibits various pharmacological activities, including anticancer effects. Several studies have reported the anticancer activity of eugenol against OSCC via different pathways. However, no current review has discussed the extent of eugenol anticancer research on oral cancer cell lines using in vitro studies. This systematic review aimed to discuss the anticancer potential of eugenol against oral cancer cell lines in vitro. Articles were selected from PubMed, ScienceDirect, SpringerLink and EBSCOhost databases based on specified inclusion and exclusion criteria. Additional articles were identified through manual hand searching. The selection process followed PRISMA guidelines. A risk-of-bias assessment was performed to evaluate the reliability and relevance of the in vitro studies. Thirteen articles with high-quality results were assessed and analysed for further investigation. These studies investigated the ability of eugenol to induce cell death through apoptotic and non-apoptotic pathways, inhibit cell proliferation and affect oxidative stress, contributing to cell death in several oral cancer cell lines. Therefore, eugenol is a potential anticancer agent for OSCC, as it exhibited anticancer activity in oral cancer cell lines in vitro studies.

Step-by-step synthetic route to access eugenol-1,2,3-triazole-chalcone hybrid.

Molecular hybridization represents a strategic approach in drug design, where two or more pharmacophoric elements from distinct bioactive molecules are integrated into a single hybrid compound. In this study, we synthesized hybrid compounds of chalcone, triazole, and eugenol through straightforward reactions using 4-hydroxyacetophenone as the starting material. Initially, 4-hydroxyacetophenone (1) underwent alkylation with 1,4-dibromobutane to produce compound 2 with an 84 % yield. Compound 2 was then subjected to azidation, resulting in azidobutoxyacetophenone 3 with a 71 % yield. Subsequently, compound 3 was reacted with either benzaldehyde or 4-methoxybenzaldehyde via base-catalyzed aldol condensation, yielding azidobutoxychalcones 4a (69 %) and 4b (84 %). Finally, azide-alkyne [3+2] cycloaddition between 4a/4b and propargylated eugenol afforded chalcone derivatives bearing eugenol-1,2,3-triazole hybrids 5a and 5b, each with a 90 % yield.•Synthesized chalcones featuring an eugenol-1,2,3-triazole scaffold using 4-hydroxyacetophenone as the starting material.•Synthesis was accomplished through a four-step reaction sequence.•Products were obtained in good yield.

An environmentally benign process to synthesize vanillin and other substituted phenyl aldehydes using natural phenylpropenes.

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 OsO4/NaIO4 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).

Asiatic acid reduces lipopolysaccharides-induced pulp inflammation through activation of nuclear factor erythroid 2-related factor 2 in rats.

Background: Dental pulp inflammation, often initiated by Gram-negative microorganisms and lipopolysaccharides (LPS), can lead to pulpitis and, subsequently, dental pulp necrosis, compromising tooth structure and increasing susceptibility to fracture. Asiatic acid, derived from Centella asiatica, has demonstrated pharmacological properties, including anti-inflammatory and antioxidant effects, making it a potential candidate for mitigating LPS-induced pulp inflammation. This in vivo study aims to investigate the impact of Asiatic acid on the nuclear factor erythroid 2-related factor 2 (Nrf2) pathway in Rattus norvegicus with LPS-induced pulp inflammation. Methods: This quasi-laboratory experimental in vivo study employed a post-test-only control group design to investigate the effects of Asiatic acid on LPS-induced pulp inflammation in Wistar rats. Thirty rats were randomly divided into six groups subjected to various interventions. LPS was administered to all groups for 6 h except the standard control group (CG, n = 5). The negative control group (NCG, n = 5) received only glass ionomer cement. The positive control group (PCG, n = 5) received Eugenol with glass ionomer cement. Intervention groups 1, 2, and 3 (IG1, IG2, IG3; n = 5 each) received Asiatic acid at concentrations of 0.5%, 1%, and 2%, respectively, with glass ionomer cement. Dental pulp inflammation was confirmed through immunological (tumor necrosis factor alpha (TNF-α) levels), histopathological (inflammatory parameters), and physiological (pain assessment using the rat grimace scale) analyses. Additionally, Nrf2 levels were examined using enzyme-linked immunosorbent assay (ELISA). Results: Asiatic acid administration significantly influenced Nrf2 levels in rats with LPS-induced pulp inflammation. Nrf2 levels were significantly higher in groups treated with 0.5% (IG1) (8.810 ± 1.092 ng/mL; p = 0.047), 1.0% (IG2) (9.132 ± 1.285 ng/mL; p = 0.020), and 2.0% (IG3) (11.972 ± 1.888 ng/mL; p = 0.000) Asiatic acid compared to NCG (7.146 ± 0.706). Notably, Nrf2 levels were also significantly higher in the 2.0% Asiatic acid group (IG3) compared to the PCG treated with Eugenol (8.846 ± 0.888 ng/mL; p = 0.001), as well as IG1 (p = 0.001) and IG2 (p = 0.002). However, no significant difference was observed between administering 0.5% Asiatic acid (IG1), 1.0% Asiatic acid (IG2), and Eugenol (PCG). Conclusion: This research showed that Asiatic acid significantly impacted the Nrf2 levels in rats with LPS-induced pulp inflammation. This suggests that it has the potential to be used as a therapeutic agent for reducing dental pulp inflammation. These findings support the need to further explore Asiatic acid as a promising intervention for maintaining dental pulp health.

The aroma transformation of Japanese sea bass (Lateolabrax japonicas) through endogenous enzyme incubation during the lag phase of attached microorganisms.

Endogenous enzymes play a crucial role in determining fish product aroma. However, the attached microorganisms can promote enzyme production, making it challenging to identify specific aromatic compounds resulting from endogenous enzymes. Thus, we investigated the aroma transformation of Japanese sea bass through enzymatic incubation by controlling attached microorganisms during the lag phase. Our results demonstrate that enzymatic incubation significantly enhances grassy and sweet notes while reducing fishy odors. These changes in aroma are associated with increased levels of 10 volatile compounds and decreased levels of 3 volatile compounds. Among them, previous studies have reported enzyme reaction pathways for octanal, 1-nonanal, vanillin, indole, linalool, geraniol, citral, and 6-methyl-5-hepten-2-one; however, the enzymatic reaction pathways for germacrene D, beta-caryophyllene, pristane, 1-tetradecene and trans-beta-ocimene remain unclear. These findings provide novel insights for further study to elucidate the impact of endogenous enzymes on fish product aromas.

Apoptosis of Pancreatic Cancer Cells after Co-Treatment with Eugenol and Tumor Necrosis Factor-Related Apoptosis-Inducing Ligand.

Pancreatic cancer is a refractory cancer with limited treatment options. Various cancer types are resistant to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL). Eugenol, the main component of clove oil, exhibits anticancer, anti-inflammatory, and antioxidant effects. However, no studies have reported that eugenol increases TRAIL sensitivity by upregulating death receptor (DR) expression. Here, we aimed to investigate eugenol as a potent TRAIL sensitizer. Increased apoptosis and inhibition of cell proliferation was observed in pancreatic cancer cells treated with eugenol and TRAIL compared with those treated with eugenol alone. Eugenol upregulated the expression of DR5, inhibited the FLICE-inhibitory protein (FLIP), an anti-apoptotic protein, and increased p53, a tumor suppressor protein. In addition, eugenol induced the generation of reactive oxygen species (ROS) and caused endoplasmic reticulum (ER) stress. C/EBP-homologous protein (CHOP) knockdown using siRNA decreased the expression of DR5 and reduced the combined effects of eugenol and TRAIL. These results demonstrate that eugenol enhances TRAIL-induced apoptosis by upregulating DR5 through the ROS-mediated ER stress-CHOP pathway, which enhances ER stress by inducing p53 and downregulating FLIP expression. This suggests that eugenol has the potential to treat pancreatic cancer by increasing cell sensitivity to TRAIL.

Eugenol's electrochemical behavior, complexation interaction with copper chloride, antioxidant activity, and potential drug molecular docking application for Covid-19.

Electrochemical studies were conducted to analyze the behavior of eugenol, CuCl2, 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 CuCl2 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.

Utilizing environment-friendly eugenol as a diluent with trioctylamine for the reactive extraction of aqueous levulinic acid.

This paper focuses on the reactive extraction of levulinic acid (LA) from aqueous solution by reactive extraction. This goal is achieved using eugenol, a green alternative in the industry, as a solvent in the liquid-liquid equilibrium (LLE) measurements for the ternary system of LA + Eugenol + H2O and quaternary systems of LA + Eugenol/ Methanol (MeOH) + H2O + Tri-n-octylamine (TOA) at T = 293.15 K. Additionally, the distribution coefficients (KD) were calculated for LA using the two diluents. Also, the ability of different diluents with TOA, in the extraction of LA were compared. The distribution coefficient of eugenol with TOA (KD = 9.44) is compared with other organic diluents which indicated that eugenol is a suitable option. MeOH, being the shortest chain alcohol, also turned out to be a diluent that could be utilized for extraction of LA with TOA. Furthermore, the Non-Random Two-Liquid (NRTL) excess Gibbs energy model was applied to correlate the measured phase equilibria. The obtained parameters were further validated using a decanter model.

Genome-Wide Analysis and Characterization of the SDR Gene Superfamily in Cinnamomum camphora and Identification of Synthase for Eugenol Biosynthesis.

Short-chain dehydrogenase/reductases (SDRs) are the largest NAD(H)-dependent oxidoreductase superfamilies and are involved in diverse metabolisms. This study presents a comprehensive genomic analysis of the SDR superfamily in Cinnamomum camphora, a species that is one of the most significant woody essential oil plants in southern China. We identify a total of 222 CcSDR proteins and classify them into five types based on their cofactor-binding and active sites: 'atypical', 'classic', 'divergent', 'extended', and 'unknown'. Phylogenetic analysis reveals three evolutionary branches within the CcSDR proteins, and further categorization using the SDR-initiative Hidden Markov model resulted in 46 families, with the CcSDR110C, CcSDR108E, and CcSDR460A families being the most populous. Collinearity analysis identified 34 pairs of CcSDR paralogs in C. camphora, 141 pairs of SDR orthologs between C. camphora and Populus trichocarpa, and 59 pairs between C. camphora and Oryza sativa. Expression profile analysis indicates a preference for the expression of 77 CcSDR genes in specific organs such as flowers, bark, twigs, roots, leaves, or fruits. Moreover, 77 genes exhibit differential expression patterns during the four developmental stages of leaves, while 130 genes show variance across the five developmental stages of fruits. Additionally, to explore the biosynthetic mechanism of methyl eugenol, a key component of the leaf essential oil in the methyl eugenol chemotype, this study also identifies eugenol synthase (EGS) within the CcSDR460A family through an integrated strategy. Real-time quantitative PCR analysis demonstrates that the expression of CcEGS in the leaves of the methyl eugenol chemotype is more than fourfold higher compared to other chemotypes. When heterologously expressed in Escherichia coli, it catalyzes the conversion of coniferyl acetate into a mixture predominantly composed of eugenol (71.44%) and isoeugenol (21.35%). These insights pave the way for future research into the functional diversity of CcSDR genes, with a focus on secondary metabolism.

Efficient Improvement of Eugenol Water Solubility by Spray Drying Encapsulation in Soluplus® and Lutrol F 127.

Herein, we present an elegant and simple method for significant improvement of eugenol water solubility using the polymers Soluplus® and Lutrol F 127 as carriers and spray drying as an encapsulation method. The formulations were optimized by adding myo-inositol-a sweetening agent-and Aerosil® 200 (colloidal, fumed silica)-an anticaking agent. The highest encapsulation efficiency of 97.9-98.2% was found for the samples containing 5% eugenol with respect to the mass of Soluplus®. The encapsulation efficiencies of the spray-dried samples with 15% eugenol are around 90%. Although lowering the yield, the addition of Lutrol F 127 results in a more regular particle shape and enhanced powder flowability. The presence of Aerosil® 200 and myo-inositol also improves the rheological powder properties. The obtained formulations can be used in various dosage forms like powders, granules, capsules, creams, and gels.

Clove essential oil and its major component, eugenol: a comparative study of their in vitro antioxidant and anticancer properties.

Syzygium aromaticum L. (clove) is a species native to subtropical countries. Its dried flower buds are rich in essential oils, which have shown insecticidal, anti-inflammatory and anaesthetic effects. This work was aimed to study the differences in antioxidant and anticancer activities between clove essential oil (CEO) and its major component, eugenol. The chemical composition of the CEO was determined by GC-MS. The physicochemical properties and antioxidant activity were determined in CEO and eugenol. Finally, anticancer activities were assayed against seven cell lines. Chemical analysis revealed that 80% of the CEO was eugenol. The density and IR were similar, and the colour was ΔE*>3. CEO had a lower phenolic content, but similar antioxidant activity to eugenol. The anticancer activity of the CEO was greater than that of eugenol in all the cell lines except for HeLa cells. These results suggest that secondary compounds in CEO enhance its antioxidant and -anticancer activities.