Search Results (45)

This study investigates the impact of using Lactiplantibacillus plantarum and Saccharomyces cerevisiae, either individually or in co-culture, on the fermentation of rose beverage. We comprehensively analyzed the resulting changes in quality characteristics and volatile compound profiles. Fermentation significantly altered the physicochemical properties, appearance, color, and free amino acid/organic acid content. Both microbial strains significantly increased total polyphenols and flavonoid content, with co-fermentation exhibiting a more pronounced effect compared to single-strain fermentations. Furthermore, the volatile compounds in rose beverages fermented with different microorganisms were characterized by an electronic nose (E-nose) and headspace–solid-phase microextraction coupled with gas chromatography–mass spectrometry (HS-SPME/GC-MS). E-nose analysis demonstrated distinct volatile profiles distinguishing the four fermentation samples. HS-SPME/GC-MS identified a total of 245 volatile compounds, among which alcohols constituted the most abundant class. Integrating GC-MS data with odor activity value (OAV ≥ 1) analysis pinpointed 34 key aroma compounds. Partial least-squares discriminant analysis (PLS-DA) based on variable importance in projection (VIP) identified eight key volatile markers: eugenol, phenylethyl alcohol, (E)-3,7-dimethyl-2,6-octadienoic acid, methyleugenol, ethyl octanoate, citronellol, D-citronellol, and 2,4-bis(1,1-dimethylethyl)phenol. These findings provide valuable insights into the microbial influence on rose beverage quality and offer a theoretical basis for optimizing industrial fermentation processes. Full article

This study investigated the phytochemical composition and biological activities of Myrtus communis essential oil (EO) from Algeria, focusing on its antimicrobial, antifungal, and insecticidal properties using in vitro and in silico approaches. Gas chromatography–mass spectrometry (GC-MS) analysis identified myrtenyl acetate (57.58%), 1,8-cineole (17.82%), and α-terpineol (6.82%) as the major constituents. M. communis EO exhibited significant antibacterial activity, particularly against Staphylococcus aureus (13.00 ± 0.70 mm) and Salmonella typhimurium (13.00 ± 1.50 mm), with moderate inhibition of Bacillus subtilis (10 ± 1.00 mm) and Escherichia coli (9.00 ± 0.70 mm), while Pseudomonas aeruginosa showed resistance. The antifungal activity was notable against Fusarium oxysporum (16.50 ± 0.50 mm), Aspergillus fumigatus (11.00 ± 1.00 mm), and Penicillium sp. (9.00 ± 0.60 mm) but ineffective against Aspergillus niger. Insecticidal activity against Tribolium castaneum was evaluated using contact toxicity, fumigation toxicity, and repellent activity assays. The EO demonstrated potent insecticidal effects, with an LC₅₀ value of 0.029 µL/insect for contact toxicity and 162.85 µL/L air for fumigation after 96 h. Additionally, the EO exhibited strong repellent activity, achieving 99.44% repellency at a concentration of 0.23 mg/cm² after 24 h. Density functional theory (DFT) calculations provided insights into the molecular geometry and electronic properties of the key bioactive compounds. Molecular docking studies evaluated their binding affinities to bacterial enzymes (DNA gyrase, dihydrofolate reductase6, and Gyrase B) and insecticidal targets (acetylcholinesterase), revealing strong interactions, particularly for geranyl acetate and methyleugenol. These findings highlight M. communis EO as a promising natural antimicrobial and insecticidal agent, with potential applications in plant protection and biopesticide development. Full article

Aromatic and medicinal plants have been integral to human civilization for thousands of years, serving not only as vital components in traditional and modern medicine but also as sources of captivating fragrances that enhance our sensory experiences. The main objective of this study was to explore the chemical composition, antioxidant and antimicrobial properties, and in silico molecular docking attributes of Gardenia jasminoides essential oil (GJEO). The chemical compositions were determined using gas chromatography–mass spectrometry (GC-MS) analysis. The antioxidant activity was determined by 2,2-Diphenyl-1-picrylhydrazyl (DPPH) and total antioxidant capacity (TAC) test. The antimicrobial activity was tested in vitro using three microbial strains (Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus), and two fungal strains (Candida albicans and Aspergillus niger). In silico analysis by molecular docking was used to determine the interaction types of topoisomerase II receptors and the most important antioxidant and antimicrobial compounds (Eugenol, Methyleugenol, and α-Terpineol ligands). The obtained results highlight the presence of 25 volatile compounds including 5 new detected compounds: Methyleugenol (15.41%), 1-Undecyne (3.4%), 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl- (1.11%), 2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)- (0.4%), and 5,9-Tetradecadiyne (0.32%). The antioxidant capacity of GJEO is around 1.25 µg equivalent of ascorbic acid/mL for TAC assay and IC50 = 19.05 µL/mL for DPPH test. GJEO exhibited significant antimicrobial activity, particularly against Pseudomonas aeruginosa, with a minimum inhibitory concentration (MIC) of 16.67 µL/mL. In silico molecular docking analysis revealed strong interactions between ethyleugenol characterized by multiple bonding interactions, including Pi–Alkyl and carbon–hydrogen bonds, while α-Terpineol formed hydrogen and alkyl interactions. These results underline the potential of Gardenia jasminoides essential oil as a promising source of bioactive compounds with antioxidant and antimicrobial properties, highlighting its possible applications in pharmaceuticals and natural therapies. Full article

Alkenylbenzenes occur as natural constituents in a variety of edible plants, in particular those herbs and spices used to give a distinctive flavor to a range of food and feed items. Some alkenylbenzenes with relevance for food, such as estragole and methyleugenol, are known to be genotoxic and carcinogenic in rodents. However, the genotoxic and carcinogenic potential of other structurally related alkenylbenzenes, such as myristicin and elemicin, is still under scientific discussion. Here, we investigated the potential of myristicin and elemicin to induce micronuclei (MN) in V79 cells in comparison to that of estragole and methyleugenol. In addition, we determined the impact of these alkenylbenzenes on cell viability and on the induction of apoptosis and necrosis. All tested alkenylbenzenes affected cell viability in a concentration-dependent manner, albeit to varying degrees. Regarding MN formation, elemicin induced a weak but statistically significant response at 100 µM and 500 µM in the absence of an exogenous metabolizing system (S9 mix). Negative results were obtained for estragole and myristicin at the highest tested non-cytotoxic concentration of 10 µM and 100 µM, respectively. For methyleugenol, the MN assay results were considered equivocal, since the observed change in MN induction was rather small and not supported by a concentration-related trend. These findings indicate that traditional in vitro test systems utilizing exogenous metabolizing systems have limited explanatory power with regard to the genotoxic potential of alkenylbenzenes. Full article

In order to reveal the fermentation microflora and fermentation metabolites of traditional mung bean sour liquid (MBSL) in Luoyang area, China, this experiment was sampled from four administrative districts of Luoyang, and volatile metabolites and non-targeted metabolites were detected and analyzed by HS-SPME-GC-MS and LC-MS, and bacterial and fungal sequencing were analyzed by Illumina MiSeq high-throughput sequencing technology. And the correlation between microorganisms and metabolites was conducted. The results showed that 42 volatiles were detected in four MBSL samples named Jianxi (JX), Liujia (Liu), LiJia (LJ), Majia (MJ), with 11 identical volatile flavor subtances, and the highest content of esters was found in JX, Liu, and LJ, and the highest content of acids was found in MJ. A total of 1703 non-targeted metabolites were identified, and there were more types of amino acids, carbohydrates, fatty acids and their complexes, flavonoids, carbonyl compounds, and organic acids, accounting for 40.93%. High-throughput sequencing results showed that there were nine bacterial and fungal genera with an average abundance of more than 1%, and the dominant genera mainly belonged to lactic acid bacteria and yeast. The composition of dominant genera was different in different workshop samples, and the abundance of fungal genera differed greatly. Among the volatile substances, Methyleugenol, a volatile component, was related to more bacteria, and ketones and hydrocarbons may be more closely associated with bacteria. Acetic acid and Oxalic acid may be more closely related to fungi, while some esters were more closely related to both fungal and bacterial genera. For non-target metabolites, amino acid and alcohol metabolites may be more influenced by bacteria, and organic acids and flavonoids may be more influenced by fungi. Full article

Laurus nobilis L. is commonly used in folk medicine in the form of infusion or decoction to treat gastrointestinal diseases and flatulence as a carminative, antiseptic, and anti-inflammatory agent. In this study, the essential oil (EO) composition of wild-grown L. nobilis L. leaves collected from seven different altitudinal locations in the Molise region and adjacent regions (Abruzzo and Campania) was investigated. EOs from the leaves were obtained by hydrodistillation and analyzed by GC-FID and GC/MS, and 78 compounds were identified. The major oil components were 1,8-cineol (43.52–31.31%), methyl-eugenol (14.96–4.07%), α-terpinyl acetate (13.00–8.51%), linalool (11.72–1.08%), sabinene (10.57–4.85%), α-pinene (7.41–3.61%), eugenol (4.12–1.97%), and terpinen-4-ol (2.33–1.25%). Chemometric techniques have been applied to compare the chemical composition. To shed light on the nutraceutical properties of the main hydrophobic secondary metabolites (≥1.0%) of laurel EOs, we assessed the in vitro antioxidant activities based on 2,2-diphenyl-1-picrylhydrazyl (DPPH•) radical scavenging activity and the reducing antioxidant power by using a ferric reducing power (FRAP) assay. Furthermore, we highlighted the anti-inflammatory effects of seven EOs able to interfere with the enzyme soluble epoxide hydrolase (sEH), a key enzyme in the arachidonic acid cascade, in concentrations ranging from 16.5 ± 4.3 to 8062.3 ± 580.9 mg/mL. Thanks to in silico studies, we investigated and rationalized the observed anti-inflammatory properties, ascribing the inhibitory activity toward the disclosed target to the most abundant volatile phytochemicals (≥1.0%) of seven EOs. Full article

Different grain sources of whiskey have great potential for aroma expression. In this paper, four whiskeys fermented from different raw materials (barley, wheat, highland barley, and sorghum) were compared. Gas chromatography–mass spectrometry (GC-MS) and sensory evaluation were used to determine the composition of the aromatic compounds. A correlation analysis was further conducted between the aromatic compounds and sensory evaluations. Barley whiskey and wheat whiskey had more pronounced fruity, floral, and grain aromas, attributed to esters and terpenes. Barley whiskey had the most compounds (55), followed by highland barley whiskey (54). Highland barley whiskey had the greatest number of unique aroma compounds (seven). It exhibited a unique cocoa aroma related to concentrations of trans-2-nonenal, γ-nonanolactone, 1-nonanol, isoamyl lactate, 2-butanol, and 6-methyl-5-hepten-2-one. Sorghum whiskey had a specific leather and mushroom aroma attributed to 6-methyl-5-hepten-2-one, ethyl lactate, ethyl caprate, phenethyl octanoate, farnesol, α-terpineol, 3-methyl-1-pentanol, and methyleugenol. Alcohols were the main aroma components of grain whiskeys. Isoamyl alcohol (231.59~281.39 mg/L), phenylethyl alcohol (5.755~9.158 mg/L), citronellol (0.224~4.103 mg/L), β-damascenone (0.021~2.431 mg/L), geraniol (0.286~1.416 mg/L), isoamyl acetate (0.157~0.918 mg/L), phenylacetaldehyde (0.162~0.470 mg/L), linalool (0.024~0.148 mg/L), 1-octen-3-ol (0.016~0.145 mg/L), trans-2-nonenal (0.027~0.105 mg/L), and trans-2-octen-1-ol (0.011~0.054 mg/L) were all important aroma compounds in the whiskeys. Full article

We previously found that feeding rats with broccoli or cauliflower leads to the formation of characteristic DNA adducts in the liver, intestine and various other tissues. We identified the critical substances in the plants as 1-methoxy-3-indolylmethyl (1-MIM) glucosinolate and its degradation product 1-MIM-OH. DNA adduct formation and the mutagenicity of 1-MIM-OH in cell models were drastically enhanced when human sulfotransferase (SULT) 1A1 was expressed. The aim of this study was to clarify the role of SULT1A1 in DNA adduct formation by 1-MIM-OH in mouse tissues in vivo. Furthermore, we compared the endogenous mouse Sult1a1 and transgenic human SULT1A1 in the activation of 1-MIM-OH using genetically modified mouse strains. We orally treated male wild-type (wt) and Sult1a1-knockout (ko) mice, as well as corresponding lines carrying the human SULT1A1-SULT1A2 gene cluster (tg and ko-tg), with 1-MIM-OH. N²-(1-MIM)-dG and N⁶-(1-MIM)-dA adducts in DNA were analysed using isotope-dilution UPLC-MS/MS. In the liver, caecum and colon adducts were abundant in mice expressing mouse and/or human SULT1A1, but were drastically reduced in ko mice (1.2–10.6% of wt). In the kidney and small intestine, adduct levels were high in mice carrying human SULT1A1-SULT1A2 genes, but low in wt and ko mice (1.8–6.3% of tg-ko). In bone marrow, adduct levels were very low, independently of the SULT1A1 status. In the stomach, they were high in all four lines. Thus, adduct formation was primarily controlled by SULT1A1 in five out of seven tissues studied, with a strong impact of differences in the tissue distribution of mouse and human SULT1A1. The behaviour of 1-MIM-OH in these models (levels and tissue distribution of DNA adducts; impact of SULTs) was similar to that of methyleugenol, classified as “probably carcinogenic to humans”. Thus, there is a need to test 1-MIM-OH for carcinogenicity in animal models and to study its adduct formation in humans consuming brassicaceous foodstuff. Full article

The current study aimed to evaluate the presence of chemical variations in essential oils (EOs) extracted from Artemisia scoparia growing at different altitudes and to reveal their antibacterial, mosquito larvicidal, and repellent activity. The gas chromatographic–mass spectrometric analysis of A. scoparia EOs revealed that the major compounds were capillene (9.6–31.8%), methyleugenol (0.2–26.6%), β-myrcene (1.9–21.4%), γ-terpinene (1.5–19.4%), trans-β-caryophyllene (0.8–12.4%), and eugenol (0.1–9.1%). The EO of A. scoparia collected from the city of Attock at low elevation was the most active against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa bacteria (minimum inhibitory concentration of 156–1250 µg/mL) and showed the best mosquito larvicidal activity (LC₅₀, 55.3 mg/L). The EOs of A. scoparia collected from the high-altitude areas of Abbottabad and Swat were the most repellent for females of Ae. aegypti and exhibited repellency for 120 min and 165 min, respectively. The results of the study reveal that different climatic conditions and altitudes have significant effects on the chemical compositions and the biological activity of essential oils extracted from the same species. Full article

Asarum heterotropoides Fr. var. mandshuricum (Maxim.) is a perennial herb native to China. Its essential oil components and asarinin are health-promoting compounds. However, cultivation under natural light can affect the growth and secondary metabolite yield of this sciophyte. Adjustment of light irradiance may be beneficial in this respect. Here, we applied six types of filtered solar irradiance by using filter films of red (I), yellow (II), blue (III), green (IV), purple (V) and 50% sunlight (VI). We measured net photosynthetic rate (APn), activity of phenylpropanoid biosynthetic enzymes, asarinin content, and essential oil content and composition. Light quality treatments V and VI resulted in increased APn, enzyme activities, asarinin content and essential oil content. Samples harvested in September 2020 had relatively higher contents and enzyme activities compared to those harvested in July 2020. Elemicin, 2,5-dimethoxytoluene and methyleugenol accumulated at higher levels in response to light quality V. Light qualities III and IV showed promising results for several compounds. Overall, we conclude that controlling the light conditions in growing environments promotes the amount of asarinin and essential oil by regulating photosynthesis and the activities of phenylpropanoid biosynthetic enzymes. Full article

Aniba canelilla (Kunth) Mez essential oil has many biological activities due to its main compound 1-nitro-2-phenylethane (1N2F), followed by methyleugenol, a carcinogenic agent. This study analyzed the influence of seasonality on yields, antioxidant capacity, and 1N2F content of A. canelilla leaf and twig essential oils. Essential oils (EOs) were extracted with hydrodistillation and analyzed with gas chromatography coupled to mass spectrometry and a flame ionization detector. Antioxidant capacity was measured using the free radical scavenging method (DPPH). Chemometric analyses were carried out to verify the influence of climatic factors on the production and composition of EOs. 1-Nitro-2-phenylethane was the major constituent in A. canelilla EOs throughout the seasonal period (68.0–89.9%); methyleugenol was not detected. Essential oil yields and the 1N2F average did not show a statistically significant difference between the dry and rainy seasons in leaves and twigs. Moderate and significant correlations between major compounds and climate factor were observed. The twig oils (36.0 ± 5.9%) a showed greater antioxidant capacity than the leaf oils (20.4 ± 5.0%). The PCA and HCA analyses showed no statistical differences between the oil samples from the dry and rainy seasons. The absence of methyleugenolin in all months of study, described for the first time, makes this specimen a reliable source of 1N2F. Full article

Major depressive disorder is a severe mood disorder characterized by different emotions and feelings. This study investigated the antidepressant activity of the phenylpropanoid methyleugenol (ME) in adult female mice exposed to a stress model induced by dexamethasone. The animals were randomly divided into groups containing eight animals and were pre-administered with dexamethasone (64 μg/kg subcutaneously). After 165 and 180 min, they were treated with ME (25, 50 and 100 mg/kg intraperitoneally) or imipramine (10 mg/kg intraperitoneally) after 45 min and 30 min, respectively; they were then submitted to tests which were filmed. The videos were analyzed blindly. In the tail suspension test, ME (50 mg/kg) increased latency and reduced immobility time. In the splash test, ME (50 mg/kg) decreased grooming latency and increased grooming time. In the open field, there was no statistical difference for the ME groups regarding the number of crosses, and ME (50 mg/kg) increased the number of rearing and time spent in the center. Regarding in silico studies, ME interacted with dopaminergic D1 and α1 adrenergic pathway receptors and with tryptophan hydroxylase inhibitor. In the in vivo evaluation of the pathways of action, the antidepressant potential of ME (50 mg/kg) was reversed by SCH23390 (4 mg/kg intraperitoneally) dopaminergic D1 receptor, Prazosin (1 mg/kg intraperitoneally) α1 adrenergic receptor, and PCPA (4 mg/kg intraperitoneally) tryptophan hydroxylase inhibitor. Our findings indicate that ME did not alter with the locomotor activity of the animals and shows antidepressant activity in female mice with the participation of the D1, α1 and serotonergic systems. Full article

Basil (Ocimum basilicum L.) is one of the main condiments for fresh consumption and essential oil production. The aim of the present work was to assess the agronomic characterization and analyze the essential oil of 63 basil accessions. The experiment was conducted in two stages in a greenhouse using vases and a hydroponic cultivation system. Oil extraction was performed employing the Soxhlet method. There was a significant variation in the agronomic characteristics among the evaluated accessions. The estimated total contents of essential oils ranged from 0.05 to 0.40%, and the major volatile fraction was methyl-eugenol. In the present study, accessions with superior performance compared to commercial varieties were found. Accession BL11 presented agronomic characteristics suitable for cultivation in a hydroponic system due to its better plant structure and late flowering. Accession BL24 stood out for essential oil extraction, producing 17.6% of linalool and a high intensity of color and odor. Accessions BL11 and BL24 presented market potential, given their higher mass productivity and higher essential oil yield, respectively. These accessions can be made available as new varieties in addition to being used in genetic improvement programs for this species. Full article

Structural, conformational, and spectroscopic investigations of methyl-eugenol were made theoretically at the B3LYP-6-311++G**level. Experimental IR, Raman, and UV-vis spectra were investigated and analyzed in light of the computed quantities. Conformational analysis was carried out with the help of total energy vs. dihedral angle curves for different tops, yielding 21 stable conformers, out of which only two have energies below the room temperature relative to the lowest energy conformer. The effect of the solvent on different molecular characteristics was investigated theoretically. MEP and HOMO-LUMO analysis were carried out and barrier heights and bioactivity scores were determined. The present investigation suggests that the molecule has three active sites with moderate bioactivity. The solvent–solute interaction is found to be dominant in the vicinity of the methoxy moieties. Full article

Alkenylbenzenes are naturally occurring secondary plant metabolites. While some of them are proven genotoxic carcinogens, other derivatives need further evaluation to clarify their toxicological properties. Furthermore, data on the occurrence of various alkenylbenzenes in plants, and especially in food products, are still limited. In this review, we tempt to give an overview of the occurrence of potentially toxic alkenylbenzenes in essential oils and extracts from plants used for flavoring purposes of foods. A focus is layed on widely known genotoxic alkenylbenzenes, such as safrole, methyleugenol, and estragole. However, essential oils and extracts that contain other alkenylbenzenes and are also often used for flavoring purposes are considered. This review may re-raise awareness of the need for quantitative occurrence data for alkenylbenzenes in certain plants but especially in final plant food supplements, processed foods, and flavored beverages as the basis for a more reliable exposure assessment of alkenylbenzenes in the future. Full article