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Mammalian odorant binding proteins (OBPs) have long been suggested to transport hydrophobic odorant molecules through the aqueous environment of the nasal mucus. While the function of OBPs as odorant transporters is supported by their hydrophobic beta‐barrel structure, no rationale has been provided on why and how these proteins facilitate the uptake of odorants from the gas phase. Here, a multi‐scale computational approach validated through available high‐resolution spectroscopy experiments reveals that the conformational space explored by carvone inside the binding cavity of porcine OBP (pOBP) is much closer to the gas than the aqueous phase, and that pOBP effectively manages to transport odorants by lowering the free energy barrier of odorant uptake. Understanding such perireceptor events is crucial to fully unravel the molecular processes underlying the olfactory sense and move towards the development of protein‐based biomimetic sensor units that can serve as artificial noses. [ABSTRACT FROM AUTHOR]

A ZnO‐mediated benzoylation between carvone oxime and acyl is reported, enabling access to diverse carvone oxime ester and carvone oxime sulfonic esters under solvent‐free conditions. The operationally simple procedure provides a novel method for the synthesis of oxime‐ester bonds with excellent chemo selectivity. This strategy provides a mild, direct, and green approach for synthesizing carvone oxime ester in moderate to excellent yields with good substrate tolerance. In addition, carvone oxime was synthesized under solvent‐free conditions. [ABSTRACT FROM AUTHOR]

BACKGROUND: Carvone and limonene are naturally occurring monoterpenoids with unique aromas, making them valuable substances in synthetic fragrance production. However, their application is limited due to low stability and rapid volatilization. To address this challenge, host–guest complexes offer a promising solution. RESULTS: In this study, two acyclic cucurbit[n]urils were synthesized to form inclusion complexes with carvone and limonene, aiming to enhance their thermal stability and achieve excellent heat release properties. The binding behavior of the complexes was investigated using NMR, X‐ray diffraction (XRD), Fourier transform infrared (FTIR) and molecular bonding analyses, confirming the formation of host–guest inclusion complexes. CONCLUSION: Our study successfully prepared four inclusion complexes (M1/CA, M2/CA, M1/LI, M2/LI) and characterized them using NMR, XRD and FTIR techniques. These complexes exhibited a 1:1 stoichiometric ratio, and their binding constants were determined through fluorescence titration. The thermal controlled release experiment shows that the degree of carvone and limonene release is different with a change of temperature, indicating that the inclusion complexes have good thermally controlled release performance, and the thermal release retention rate has a certain correlation with KS value. The larger the KS value, the higher the thermal release retention rate of the inclusion complexes, the lower the volatilization of the inclusion complexes, the longer the retention time and the better the thermal stability. This study presents a novel approach for developing carvone‐ and limonene‐based fragrances, expanding their application potential in various industries. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Carvone, a natural monoterpene, has been identified in various plants, giving them a characteristic scent. Enantiomers (R-(–) and S-(+)) reveal specific biological activities that are successfully used in traditional medicine for their antifungal, antibacterial, antiparasitic, and anti-influenza properties. The presented paper is based on S-(+)-carvone, characterized by a specific caraway scent, which revealed rich biological activities both in vitro and in vivo. Thus, the aim of the study was to evaluate the potential anti-neurodegenerative activity of S-(+)-carvone, including in vitro experiments (butyrylcholinesterase inhibitory, neuro- and hepatotoxicity as well as neuro- and hepatoprotective activity), in vivo (memory acquisition, locomotor activity), and ex vivo (determination of S-(+)-carvone's level in tissues collected from mice). Results revealed the multidirectional character of S-(+)-carvone. It has been shown that S-(+)-carvone is capable of butyrylcholinesterase inhibition (40% for 0.025 mg applied onto the plate), and neuroprotection and hepatoprotection at selective concentrations against reactive oxygen species generation and lipid peroxidation along with non-hepatotoxicity character. Additionally, multiple-dose administration of the monoterpene at a dose of 100 mg/kg had a positive influence on memory acquisition. Gas chromatography–mass spectrometry analysis of the plasma and the brain showed that S-(+)-carvone can cross the blood–brain barrier and accumulate in the hippocampus (0.217 µg/mg of tissue), a crucial part of the brain associated with cognition and mental functions. [ABSTRACT FROM AUTHOR]

[(Bn-tpen)FeII(MeCN)](ClO4)2, containing the pentadentate Bn-tpen–N-benzyl-N,N′,N′-tris(2-pyridylmethyl)-1,2-diaminoethane ligand, was studied in the oxygenation of cyclohexene and limonene using low-pressure dioxygen (0.2 atm air or 1 atm pure O2) in acetonitrile. 2-Cyclohexen-1-one and 2-cyclohexen-1-ol are the main products of cyclohexene oxidations, with cyclohexene oxide as a minor product. Limonene is oxidized to limonene oxide, carvone, and carveol. Other oxidation products such as perillaldehyde and perillyl alcohol are found in trace amounts. This catalyst is slightly less active than the previously reported [(N4Py)FeII(MeCN)](ClO4)2 (N4Py–N,N-bis(2-pyridylmethyl)-N-(bis-2-pyridylmethyl)amine). Based on cyclic voltammetry experiments, it is postulated that [(Bn-tpen)FeIV=O]2+ is the active species. The induction period of approx. 3 h during cyclohexene oxygenation is probably caused by deactivation of the reactive Fe(IV)=O species by the parent Fe(II) complex. Equimolar mixtures of Fe(II) salt and the ligand (in situ-formed catalyst) gave catalytic performance similar to that of the synthesized catalyst. [ABSTRACT FROM AUTHOR]

Mints are aromatic plants of Lamiaceae, globally known for the phytochemical-rich essential oils. Most of the cultivated mints are menthol-rich, whereas spearmint being the only dominant carvone-rich species. In this study, another carvone-rich mint Mentha rotundifolia (L.) Huds., a native of temperate region was assessed for its acclimation in sub-tropical environment to see any possible changes in specialized metabolite accumulation. Plants grown under open environment was compared with glasshouse grown plants where, temperature, humidity and photoperiods were uniformly maintained. Thickened leaves with increased cuticular wax load (2.82 folds) and anthocyanin accumulation (202.97 µg/g) in the widened stems were observed in plants grown in open environment, while higher chlorophyll contents were exhibited by the glasshouse-grown plants. Enhanced antioxidant capacity in open environment, correlated with elevated concentration (86.4% increase for caffeic acid) of wall-bound phenolics was observed. Increased proline, hydrogen peroxide and malondialdehyde contents in open environment indicated the plant's ability to cope up with abiotic stress. Higher amounts of terpenes like (-)-carvone (2.68 folds) and D-limonene (1.35 folds) were found in both internal volatile pool and essential oil of glasshouse-grown plants. Histochemical study of glandular trichomes also supported this finding. In conclusion, glasshouse-grown plants showed relatively better growth and higher terpene contents, nevertheless the plant survived well in warmer environment, with increased antioxidant capacities and phenolic contents. Future study includes mass propagation of this species in different geographical locations with distinct climatic variations to determine the suitable sub-tropical locations for cultivation as a potential alternative to spearmint for commercial-scale (-)-carvone production. [ABSTRACT FROM AUTHOR]

Stomoxys flies exhibit an attraction toward objects that offer no rewards, such as traps and targets devoid of blood or nectar incentives. This behavior provides an opportunity to develop effective tools for vector control and monitoring. However, for these systems to be sustainable and eco-friendly, the visual cues used must be specific to target vector(s). In this study, we modified the existing blue Vavoua trap, which was originally designed to attract biting flies, to create a deceptive host attraction system specifically biased toward attracting Stomoxys. Our research revealed that Stomoxys flies are attracted to various colors, with red proving to be the most attractive and selective color for Stomoxys compared to the other colors tested. Interestingly, our investigation of the cattle–Stomoxys interaction demonstrated that Stomoxys flies do not prefer a specific livestock fur color phenotype, despite variation in the spectrum. To create a realistic sensory impression of the trap in the Stomoxys nervous system, we incorporated olfactory cues from livestock host odors that significantly increased trap catches. The optimized novel polymer bead dispenser is capable of effectively releasing the attractive odor carvone + p-cresol, with strong plume strands and longevity. Overall, red trap baited with polymer bead dispenser is environmentally preferred. [ABSTRACT FROM AUTHOR]

Combination of crop protectants is an important approach to increase insecticidal efficacy and reduce the application rates. In this study, the insecticidal efficacy of spinosad and seven monoterpenes, alone and in binary combinations, was evaluated against Sitophilus oryzae (L.) (Coleoptera: Curculionidae) in stored wheat. Spinosad was tested at application rates of 0.1 and 0.5 mg/kg while monoterpenes were tested at 0.5, 1.0 and 2.0 g/kg. Mortality of adults after 7, 14 and 21 days, progeny reduction after 45 and 90 days, and grain weight loss were recorded for all treatments. The results showed that the complete mortality (100.0%) of S. oryzae adults was observed in wheat treated with 0.5 mg/kg of spinosad + 2.0 g/kg of carvone or P-cymene or menthone after 21 days. At the same time, no progeny of S. oryzae was resulted in the combined treatments (0.5 mg/kg of spinosad + 2.0 g/kg of carvone or 0.5 mg/kg of spinosad + 2.0 g/kg of P-cymene) after 45 and 90 days. The same trends were observed for grains weight loss as the binary treatments at highest application rates preserved the wheat seeds free from damage caused by S. oryzae for 90 days. [ABSTRACT FROM AUTHOR]

Dill (Anethum graveolens L.) is a popular herb of the Apiaceae family, widely used in medicine and food industry. The aim of this study is to measure the effects of polyamines on the percent and the compounds of the dill essential oil. This study was conducted in three replications in a Randomized Complete Block Design (RCBD). The treatment compounds were made up of polyamines (spermine, spermidine, and putrescine) at 50, 100 and 150 mg/l concentrations, respectively. The foliar application of polyamines was performed in three replications in the beginning of the flowering stage. It was repeated 14 days apart. Our results demonstrated that the maximum values of dill essential oil (3.58%) were obtained by application of 100 mg/l of putrescine. The dill essential oil compounds include: α-phellandrene (4.03%) was obtained by application of 50 mg/l of putrescine treatment, and the maximum values of limonene (41.63%) were obtained by application of 50 mg/l spermidine treatment. but, the highest values of carvone and trans- dihydrocarone (61.96%) and (5.76%) were observed in the control treatment. The dill essential oil compounds are generally affected by the cultivar, plant type, harvest time, geographical factors, and type of fertilizers. It is also vital to mention that among polyamines, spermidine and putrescine (50 mg/l) at the lowest concentration had the highest influence on the value of the main compounds of dill essential oil. [ABSTRACT FROM AUTHOR]

Currently available antifungal therapies often have limitations such as toxicity and the development of resistance. The aim of this study was to investigate the antifungal activity and mode of action of Caraway (Carum carvi L.) essential oil (EO) and its constituent carvone against A. fumigatus, a fungal pathogen responsible for invasive aspergillosis. Caraway EO was obtained by hydrodistillation, and its antifungal activity was assessed by the broth microdilution method according to the CLSI protocol. The ergosterol content of fungal mycelia was measured using a spectrophotometric method. The mode of action of Caraway EO was assessed by electron microscopy. The interaction between Caraway EO and two known antifungals, itraconazole and caspofungin, was evaluated by determining the fractional inhibitory concentration index (FICI). At twofold dilutions ranging from 3.12 to 400 µg/mL, Caraway EO inhibited A. fumigatus growth by 10.27–100 %, with a minimum inhibitory concentration (MIC) of 200 µg/mL, while carvone inhibited fungal growth by 7.31–67.58 %, with an MIC of 400 µg/mL. The IC 50 values of the Caraway EO and carvone were 56.09 and 47.68 μg/mL, respectively. Moreover, the minimum fungicidal concentration (MFC) of the Caraway EO was reported to be 400 μg/mL. Both Caraway EO and carvone significantly inhibited ergosterol biosynthesis in A. fumigatus. Caraway EO showed synergistic antifungal activity in combination with itraconazole (FICI=0.38) and additive antifungal activity (FICI=0.75) in combination with caspofungin. Caraway EO and its constituent carvone showed strong antifungal activity against A. fumigatus by inhibiting ergosterol biosynthesis and destroying essential compartments of fungal mycelia, such as mitochondria. In addition, the combination of carvone with itraconazole or caspofungin had synergistic/additive effects, suggesting potential therapeutic efficacy for the treatment of A. fumigatus -related infections. [Display omitted] • Caraway (Carum carvi L.) essential oil (EO) and its constituent carvone strongly inhibited the growth of A. fumigatus. • Caraway EO and carvone suppressed ergosterol synthesis in the fungal hyphae dose-dependently. • Caraway EO altered fungal morphology by destructing membranous structures of the fungal hyphae. • Inhibition of A. fumigatus growth may be attributed to impaired ergosterol synthesis and increased cell membrane permeability. [ABSTRACT FROM AUTHOR]

Investigations have shown that storage bugs seriously harm grains during storage. In the interim, essential oils (EOs) have been proven to be a good botanical pesticide. The anti-Lasioderma serricorne properties of Elsholtzia ciliata essential oil, which was obtained by steam distillation, were evaluated using DL-limonene, carvone, and their two optical isomer components using contact, repelling, and fumigation techniques. Simultaneously, the fumigation, contact, and repellent activities of carvone and its two optical isomers mixed with DL-limonene against L. serruricorne were evaluated. The results showed that E. ciliata, its main components (R-carvone, DL-limonene), and S-carvone exhibited both fumigations (LC50 = 14.47, 4.42, 20.9 and 3.78 mg/L) and contact (LD50 = 7.31, 4.03, 28.62 and 5.63 µg/adult) activity against L.serricorne. A binary mixture (1:1) of R-carvone and DL-limonene displayed an obvious synergistic effect. A binary mixture (1:1) of carvone and its two optical isomers exhibited an obvious synergistic effect, too. Furthermore, the repellent activity of the EO, carvone, and its two optical isomers, DL-limonene, and a combination of them varied. To stop insect damage during storage, E. ciliata and its components can be utilized as bio-insecticides. [ABSTRACT FROM AUTHOR]

Background and aim: Carvone (CV) is a monoterpene in some essential oils that has therapeutic uses. The current study was undertaken to assay the antioxidant and antidepressant activities of CV and its possible mode of action using tail suspension test (TST) and open-field test (OFT). Methods: The acute toxicity of the CV was assessed by Lorke's method. Several doses of CV (25–100 mg kg−1) were injected 1 hour prior to TST. To evaluate the possible mode of action, receptor antagonists were administered 1 hour prior to the CV treatment (100 mg kg −1), and after 30 min, the TST was conducted. Moreover, the animal's serum catalase (CAT), glutathione (GSH), and nitric oxide(NO) were measured. Results: The LD50 of CV was 3.807 g kg−1. Moreover, the CV increased serum CAT and GSH and decreased NO levels. The 50 and 100 mg kg−1 of CA have potential antidepressant activity and decresed the numbers of crossings and rearings in OFT. Our results indicate that haloperidol, sulpiride, SCH23390, ketanserin WAY100135, yohimbine, prazosin, p-chlorophenylalanine (pCPA), and reserpine inhibited the antidepressant potential of CV (100 mg kg−1). The simultaneous use of a sub-dose of CV (25 mg kg−1) with fluoxetine (5 mg kg−1) enhances the antidepressant-like response. Conclusion: The CV presumably exerts antidepressant potential by acting as an antioxidant and enhancing dopamine, noradrenaline, and serotonin in synaptic clefts. Besides, the reduction in locomotor activity is indicative of the sedative effects of CV. These results promote the use of CV in commercial combinations as an adjuvant agent with traditional antidepressant agents.

Purpose: The use of synthetic pesticides to control the spread of mosquito-borne diseases has caused environmental pollution and insecticide resistance in mosquitoes. Developments of new green insecticides have thus received more attention to overcome these problems. Methods: Nanoliposomes containing carvone and essential oils were first prepared. The nanoliposome physicochemical characteristics (particle size, morphology, and successful loading) were then evaluated by Dynamic Light Scattering (DLS), Transmission Electron Microscopy (TEM), and the Attenuated Total Reflection-Fourier Transform InfraRed (ATR-FTIR) analyses. Larvicidal effects of carvone, Mentha spicata, and Tanacetum balsamita essential oils were investigated against the main malaria vector, Anopheles stephensi, in non-formulated and nanoformulated states. Results: The larvicidal effects of nanoformulated states were significantly more potent (7.2 folds, 3.5 folds, and 8 folds) than non-formulated states. Nanoliposomes containing M. spicata and T. balsamita essential oils with particle sizes of 175 ± 8 and 184 ± 5 nm showed the best efficacies (LC50 values = 9.74 and 9.36 μg/mL). Conclusion: The prepared samples could be used as new green potent larvicides against An stephensi mosquito in further field trials. It is also recommended to investigate their efficacies against other mosquitoes. [ABSTRACT FROM AUTHOR]

Monoterpenes are secondary plant metabolites, and such volatile compounds have antioxidant, antibacterial, antiviral, and enzyme inhibitory properties. These compounds are also able to reduce the potentially pro-neurodegenerative trace metal ions that can be sources of free radicals. One basic method used to evaluate the ability of chemical compounds to reduce Fe(III) is FRAP. To date, most studies based on a FRAP assay were performed within several dozen minutes. However, taking into account the diversity of compounds, it is justified to observe their activity over a much longer period of time. The present study aimed to observe the activity of isopulegol, γ-terpinene, α-terpinene, linalool, carvone, citral, and α-phellandrene over a 48 h period. Our study indicates that the lengthened reaction period enhanced activity from several dozen to several hundred percent. The obtained results also revealed an explicit high correlation of the increase in the activity of compounds with the increase in monoterpene concentration. Due to the hydrophobic character of monoterpenes, the FRAP method was modified by the addition of Tween 20. The highest activity was obtained for α-terpinene and γ-terpinene. [ABSTRACT FROM AUTHOR]

Background: Contact allergy to the mint‐tasting flavour carvone has been observed in patients with oral lichenoid lesions (OLL). Mint‐flavoured products such as toothpaste frequently contain carvone. Snuff is a smokeless tobacco product that is chewed or placed in the mouth rather than smoked. In Sweden, the use of snuff and its flavoured versions is extremely common. Objectives: To investigate whether the consumption of mint‐flavoured snuff is associated with contact allergy to carvone and subsequently plays a role in the aetiology of OLL. Methods: Regarding the two patients, patch testing with snuff pouches was performed. High‐performance liquid chromatography and gas chromatography–mass spectrometry analysis were used for identification of carvone in different snuff samples. Results: Two patients with OLL were contacted allergic to carvone when patch tested. Both were using mint‐flavoured snuffs several hours a day for many years. One patient was contacted allergic to the snuff pouch tested as is. Carvone was detected in the snuff samples of both patients. Conclusions: The patients were recommended to avoid the use of mint‐flavoured snuffs, toothpaste and foodstuffs. At follow‐up 3 months later, the patients had a dramatic clinical improvement of the OLL and oral symptoms. Exposure to mint‐flavoured snuffs can be overlooked as a possible aggravating/provoking factor in OLL. [ABSTRACT FROM AUTHOR]

Aim: Epilepsy affects approximately 70 million people worldwide. While many drugs can prevent seizures, they have a limited impact on preventing or curing the disease. In this perspective, natural compounds, especially monoterpenes derived from medicinal plants, have been investigated in epilepsy models, such as carvone (CAR). The principal constituent of peppermint oil, (R)-(-)-carvone (R-CAR), and the primary component in cumin and dill seed oils, (S)-(+)-carvone (S-CAR), find diverse applications in cosmetics, food, and pharmaceutical formulations. This study aims to investigate the antiepileptic effects of the natural compounds S-CAR and R-CAR in penicillin (PEN)-induced experimental epilepsy model in rats. Material and Method: In the research, 91 male Wistar rats were used. The rats were grouped into 3 main groups as common groups, pre-penicillin groups and post-penicillin groups. The main groups were divided into a total of 13 subgroups. Electrocardiogram recording was taken from rats. At the end of the experiment, the latency of the first epileptiform activity (EA), spike-wave frequency (SWF), and spike-wave amplitude (SWA) of the EA were analyzed. Results: S-CAR and R-CAR administered before penicillin prolonged the latency to the onset of the first EA. S-CAR and R-CAR administered before penicillin decreased SWF. 100 mg/kg doses of S-CAR and R-CAR injected 30 minutes after penicillin administration decreased SWF. While 200 mg/kg dose of R-CAR administered before penicillin decreased SWA in a time-dependent manner, 100 mg/kg dose of S-CAR administered after penicillin decreased SWA. Conclusion: These findings indicate that carvone could exhibit both protective and therapeutic effects in the management of epilepsy. [ABSTRACT FROM AUTHOR]

Introduction: In this study, we examined the impact of a hydroethanolic extract derived from ajwain and carvone (a compound present in ajwain), on learning, spatial memory, and anxiety levels in adult male rats that were chronically immobilized. Methods: There were 60 rats used in this study, divided into six groups of 10 rats each. To expose stress, 30 rats (in 3 groups including Stress, Stress-Carvone, and Stress-Ajwain groups) were placed in a restrainer for 6 hours every day for 21 consecutive days. Stress-Carvone and Stress-Ajwain groups received carvone (20 mg/kg) and ajwain extract (500 mg/kg) by gavage respectively. Thirty rats were also used in three groups (Control, Carvone, and Ajwain groups). Spatial learning and memory were studied using the Morris water maze, and anxiety was assessed by the elevated-plus maze. Results: Compared to the control group, chronic immobilization caused the rats to swim a longer time (P < 0.01) and distance (P < 0.05) to reach the hidden platform, and a shorter time and distance to swim in the target quarter (P < 0.05) in the Morris water maze. The percentage of entering the open arm in the elevated plus maze (P < 0.001) and the percentage of time staying in this arm (P < 0.01) were lower than the control group. The carvone improved the performance of stressed animals in the Morris maze, but the ajwain extract had no effect on the memory deficit of stressed animals. Furthermore, treating ajwain extract and carvone increased the percentage of entry into the open arm and the percentage of time spent in the open arm in animals exposed to stress. Conclusion: Ajwain extract and carvone reduce anxiety behavior in rats exposed to chronic immobility stress; carvone treatment prevents memory impairment in these animals. It is possible that the extract of ajwain (partially through carvone) is effective in reducing damage caused by stress in the nervous system.

Abstract Xanthomonas campestris pv. vesicatoria (Xcv) causes brown spots on the leaves, stems, and fruits of plants, called bacterial leaf scorch (BLS). For the control of pathogens, antibiotics have been used frequently, and they can develop the resistance. In this study, the bactericidal and synergistic effects of caraway oil and its main components against the pathogen (Xcv) were investigated. The tested caraway oil consisted of 58.4% of carvone and 31.1% of limonene. The minimum inhibitory concentration (MIC) of caraway oil and carvone was the same as 125 μg mL−1, and the minimum bactericidal concentration (MBC) was 1000 μg mL−1 for caraway oil and 500 μg mL−1 for carvone, while limonene showed no inhibition below 1000 μg ml−1. In the growth of Xcv, carvone treatment over 31.3 μg mL−1 inhibited dose-dependently, and the bactericidal effect showed after 18 h more than 250 μg mL−1; It was agreed with the release of intracellular components over 250 μg mL−1, especially. Furthermore, carvone damaged the plasmid DNA of Xcv, and it would be the reason for the bactericidal activity. The synergistic effect of carvone was found with β-lactams selectively; the fractional inhibitory concentration (FIC) indexes of carvone with ampicillin or amoxicillin were below 0.5, and the mixture of carvone (125 μg mL−1) and ampicillin (500 μg mL−1) showed the bactericidal activity as well.

This study investigated the elicitation effects of several methyl jasmonate (MeJ) concentrations (0, 25, 50, and 100 mM) on various biochemical traits of caraway (Carum carvi L.) callus cultures. The 25 lM MeJ concentration yielded the highest callus growth rate (0.57mm day-1), total flavonols content (2.58mg QE g-1 FW) and total carotenoids content (0.04 lg g-1 FW), whereas the highest relative fresh weight (75.72%), total phenolics content (76.90mg GAE g-1 FW), total flavonoids content (58.49mg QE g-1 FW) and phenylalanine ammonia lyase activity (3.40nmol cinnamic acid mg-1 h-1 FW) were obtained with the 50 lM MeJ concentration. The highest antioxidant activity through DPPH assay (8.37%) and malondialdehyde content (7.82 lmol g-1 FW) were observed at 100 lM MeJ. The HPLC conducted 21 days post-elicitation revealed a 5.55-fold increase of carvone accumulation (1.83 lg g-1 DW) at 50 lM MeJ and a 2.7-fold increase (0.62 lg g-1 DW) of limonene at 50 lM MeJ. The optimal dosages applied for carvone and limonene accumulation under MeJ elicitation could be used to scale up the economic production of these elite medicinal compounds through caraway callus cultures. [ABSTRACT FROM AUTHOR]

This study investigated the efficacy of carvone, abscisic acid (ABA), gibberellin (GA3), and variable temperature in managing dormancy and sprouting in aeroponically grown mini-tuber potato (Solanum tuberosum L.) seeds. The results showed that carvone treatment effectively reduced the weight loss rate by 12.25% and decay rate by 3.33% at day 25 compared to control. ABA treatment significantly enhanced the germination rate, increasing it to 97.33%. GA3 treatment resulted in the longest sprouts of 14.24 mm and reduced the MDA content by 23.08% at day 30, indicating its potential in shortening dormancy and maintaining membrane integrity. The variable-temperature treatment demonstrated a balanced performance in reducing weight loss and maintaining a lower relative conductivity, indicating less cellular damage. The enzymatic activities of α-amylase, CAT, and SOD were modulated by the treatments, ensuring a balanced enzymatic environment for seed vitality. These results establish a solid basis for improving postharvest management strategies to optimize germination uniformity and preserve the quality of aeroponic potato seeds during extended dormancy, promising enhanced yield and productivity in potato cultivation. [ABSTRACT FROM AUTHOR]

Background: The role of contact sensitisation in the pathogenesis of oral lichen planus (OLP) has not been clearly defined. Objective: We aimed to evaluate relevant contact sensitisers in OLP. Methods: A retrospective study was conducted on OLP patients who underwent patch testing from 1 January 2006 to 31 December 2020 at an Australian tertiary dermatology institution, compared to cheilitis patients patch tested over the same time period. Results: Ninety‐six OLP patients and 152 cheilitis patients were patch tested during the 15‐year period. Seventy‐one (73.9%) OLP patients and 100 (65.8%) cheilitis patients recorded one or more relevant reactions. Forty‐three (44.8%), 22 (22.9%), 21 (21.9%) and 17 (17.7%) OLP patients had relevant reactions to mercury‐related chemicals, amalgam, spearmint and carvone, respectively, compared to 6 (3.9%), 3 (2.0%), 4 (2.6%) and 0 (0%) cheilitis patients, respectively (p‐value <0.001 each). Four (4.2%) OLP patients had relevant positive reactions to sodium metabisulfite, compared to none in the cheilitis group (p‐value 0.021). Conclusion: While dental amalgam is used less frequently these days, we report that mercury (found in amalgam) and additionally spearmint and carvone are relevant sensitisers in OLP in Australia. Sodium metabisulfite may also be a relevant sensitiser in OLP, which has not previously been reported. [ABSTRACT FROM AUTHOR]

The reactions of (3S,4RS)-1,3-dideoxy-3-[(2Z)-4-methoxy-3-methyl-4-oxobut-2-en1-yl]-4-C-methyl-4,5-O-(1-methylethylidene)pent-2-ulose with MCPBA and trifluoroperacetic acid were studied. It was shown that 60% MCPBA in CH2Cl2 at room temperature caused isomerization in the acetonide fragment of this compound, while no expected Baeyer—Villiger (B—V) reaction was observed at the methyl ketone. In the MCPBA—AcONa system, the epoxidation of the activated double bond followed the conjugate addition—elimination scheme. The oxidation with trifluoroperacetic acid occurred at the methyl ketone moiety with subsequent decomposition of the dioxolane protecting group and intramolecular lactonization. The introduction into the B—V reaction of the corresponding aldehyde-containing partner instead of the methyl ketone-containing ulose led to an abnormal product of furanization with the loss of the chiral center. [ABSTRACT FROM AUTHOR]

Investigations have shown that storage bugs seriously harm grains during storage. In the interim, essential oils (EOs) have been proven to be a good botanical pesticide. The anti-Lasioderma serricorne properties of Elsholtzia ciliata essential oil, which was obtained by steam distillation, were evaluated using DL-limonene, carvone, and their two optical isomer components using contact, repelling, and fumigation techniques. Simultaneously, the fumigation, contact, and repellent activities of carvone and its two optical isomers mixed with DL-limonene against L. serruricorne were evaluated. The results showed that E. ciliata, its main components (R-carvone, DL-limonene), and S-carvone exhibited both fumigations (LC50 = 14.47, 4.42, 20.9 and 3.78 mg/L) and contact (LD50 = 7.31, 4.03, 28.62 and 5.63 µg/adult) activity against L.serricorne. A binary mixture (1:1) of R-carvone and DL-limonene displayed an obvious synergistic effect. A binary mixture (1:1) of carvone and its two optical isomers exhibited an obvious synergistic effect, too. Furthermore, the repellent activity of the EO, carvone, and its two optical isomers, DL-limonene, and a combination of them varied. To stop insect damage during storage, E. ciliata and its components can be utilized as bio-insecticides.

Helicobacter pylori infections are highly common amongst the global population. Such infections have been shown to be the cause of gastric ulcers and stomach carcinoma and, unfortunately, most cases are asymptomatic. Standard treatment requires antibiotics such as metronidazole or azithromycin to which many strains are now resistant. Mentha species have been used as a natural treatment for gastrointestinal diseases throughout history and essential oils (EOs) derived from these plants show promising results as potential antimicrobial agents. In this study, EOs obtained from the leaves and flowers of five cultivars of Mentha × piperita and M. spicata were examined by GC-MS. The investigated mints are representatives of four chemotypes: the menthol chemotype (M. × piperita 'Multimentha' and M. × piperita 'Swiss'), the piperitenone oxide chemotype (M. × piperita 'Almira'), the linalool chemotype (M. × piperita 'Granada'), and the carvone chemotype (M. spicata 'Moroccan'). The chemical composition of EOs from mint flowers and leaves was comparable with the exception of the Swiss cultivar. Menthol was the most abundant component in the leaves while menthone was highest in flowers. The H. pylori ATCC 43504 reference strain and 10 other H. pylori clinical strains were examined for their sensitivity to the EOs in addition to their major monoterpenoid components (menthol, menthone, carvone, dihydrocarvone, linalool, 1,8-cineole, and limonene). All tested mint EOs showed inhibitory activity against both the reference H. pylori ATCC 43504 strain (MIC 15.6–31.3 mg/L) and clinical H. pylori strains (MIC50/90 31.3–250 mg/L/62.5–500 mg/L). Among the reference monoterpenes, menthol (MIC50/90 7.8/31.3 mg/L) and carvone (MIC50/90 31.3/62.5 mg/L) had the highest anti-H. pylori activity, which also correlated with a higher activity of EOs containing these compounds (M. × piperita 'Swiss' and M. spicata 'Moroccan'). A synergistic and additive interaction between the most active EOs/compounds and antibiotics possibly points to a new plant-based anti-H. pylori treatment. [ABSTRACT FROM AUTHOR]

Xanthomonas campestris pv. vesicatoria (Xcv) causes brown spots on the leaves, stems, and fruits of plants, called bacterial leaf scorch (BLS). For the control of pathogens, antibiotics have been used frequently, and they can develop the resistance. In this study, the bactericidal and synergistic effects of caraway oil and its main components against the pathogen (Xcv) were investigated. The tested caraway oil consisted of 58.4% of carvone and 31.1% of limonene. The minimum inhibitory concentration (MIC) of caraway oil and carvone was the same as 125 μg mL−1, and the minimum bactericidal concentration (MBC) was 1000 μg mL−1 for caraway oil and 500 μg mL−1 for carvone, while limonene showed no inhibition below 1000 μg ml−1. In the growth of Xcv, carvone treatment over 31.3 μg mL−1 inhibited dose-dependently, and the bactericidal effect showed after 18 h more than 250 μg mL−1; It was agreed with the release of intracellular components over 250 μg mL−1, especially. Furthermore, carvone damaged the plasmid DNA of Xcv, and it would be the reason for the bactericidal activity. The synergistic effect of carvone was found with β-lactams selectively; the fractional inhibitory concentration (FIC) indexes of carvone with ampicillin or amoxicillin were below 0.5, and the mixture of carvone (125 μg mL−1) and ampicillin (500 μg mL−1) showed the bactericidal activity as well. [ABSTRACT FROM AUTHOR]

The postharvest life of most fruit, vegetables and cereals is limited by fungal proliferation. The chemical composition of Mentha piperita, M. spicata and M. suaveolens essential oils (EO), and the antifungal activity against four pathogenic and post-harvest fungi isolated from food, were herein investigated to evaluate their potential as natural food preservatives. The EO were obtained by hydrodistillation of aerial parts leaves, stems and inflorescences (except for peppermint oil, which was purchased in a specialized store) and submitted to GC-MS and GC-FID analysis. Regarding the EO composition, carvone (41.1%) and limonene (14.1%) were the major compounds in M. spicata, menthol (47.0%) and menthone (23.1%), as well as other menthol derivatives (neomenthol -3.6%- and menthofurane -3.7%-) in M. piperita, and piperitone oxide (40.2%) and piperitenone oxide (31.4%) in M. suaveolens. Botryotinia fuckeliana was the most sensitive fungus. The three studied EO inhibited growth by 92–100%. The highest dose of M. suaveolens EO, 400 µg/mL, produced 100% MGI in all the studied fungi, except Fusarium oxysporum with 94.21%. The M. suaveolens EO can be considered to develop a low-risk enviro-friendly botanical biofungicide.

Obesity is characterized by an expansion of adipose tissue due to excessive accumulation of triglycerides in adipocytes, causing hypertrophy and hyperplasia, followed by hypoxia, alterations in adipocyte functionality, and chronic inflammation. However, current treatments require changes in lifestyle that are difficult to achieve and some treatments do not generate sustained weight loss over time. Therefore, we evaluated the effect of the essential oil (EO) of Lippia alba (Verbenaceae) carvone chemotype on viability, lipid mobilization, and adipogenesis of adipocytes in two normal and pathological cellular models in vitro. In 3T3-L1 adipocytes, a normal and a pathological model of obesity were induced, and then the cells were treated with L. alba carvone chemotype EO to evaluate cell viability, lipid mobilization, and adipogenesis. L. alba carvone chemotype EO does not decrease adipocyte viability at concentrations of 0.1, 1, and 5 µg/mL; furthermore, there was evidence of changes in lipid mobilization and adipogenesis, leading to a reversal of adipocyte hypertrophy. These results could be due to effects produced by EO on lipogenic and lipolytic pathways, as well as modifications in the expression of adipogenesis genes. L. alba carvone chemotype EO could be considered as a possible treatment for obesity, using the adipocyte as a therapeutic target.

Spearmint essential oil and pure dew were used as research objects, the antioxidant capacity of spearmint was evaluated by measuring the scavenging capacity of superoxide anion radical and hydroxyl radical, providing technical support for the subsequent development and utilization of spearmint truffle and essential oil. The results showed that when the volume fraction (V/V) of spearmint essential oil was 1%, its antioxidant capacity was the strongest, and its scavenging rates of superoxide anion radical and hydroxyl radical were 50.94% and 90.11% respectively; When the volume fraction (V/V) of spearmint hydrosol was 100%, its antioxidant capacity was the strongest, and its scavenging rates of superoxide anion radical and hydroxyl radical were 47.65% and 45.60%. [ABSTRACT FROM AUTHOR]

The investigation of the effect of carvone (a natural monoterpene) on liver damage caused by chronic immobilisation. Male Wistar rats were divided into four groups: control, carvone, stress, and stress-carvone. To induce stress, rats were placed in a restrainer (6 h/21 day) and carvone was treated by gavage at a dose of 20 mg/kg. Alkaline phosphatase, aspartate aminotransferase, and alanine aminotransferase activities were significantly increased in sera of immobilised rats. Chronic immobilisation also increased malondialdehyde levels and decreased reduced glutathione content, as well as increased TNF-α, IL-1β, IL-6, and NF-κB mRNA expression and also led to the infiltration of inflammatory cells in the liver parenchyma. Carvone's 21-day treatment prevented all of these changes in immobilised rats. It is concluded that carvone has effectively prevented chronic immobilisation-induced liver injury, most probably through its antioxidant and anti-inflammatory capabilities. [ABSTRACT FROM AUTHOR]

Medical devices are often vulnerable to colonization by nosocomial pathogens (bacteria), leading to infections. Traditional sterilization methods may not always be effective, and as a result, alternative options are being explored to prevent microbial contamination. Recently, scientists are emphasizing using plant-derived essential oils that possess inherent antibacterial properties to produce antimicrobial coatings using plasma polymerization technology carried out at atmospheric pressure (AP). This approach shows promise compared to other coating strategies that need several processing steps, including a high-vacuum system, and are laborious, such as the immobilization of antimicrobial materials on precoated layers in the low-pressure plasma polymerization approach. The present study demonstrates the potential of AP plasma polymerization for producing thin films with excellent antibacterial properties and surface characteristics. The resulting coatings are stable, smooth, and have high wettability, making them ideal for repelling bacteria. The calculated zeta potential and deposition rate for the films are also favorable. These AP plasma-polymerized thin films created from carvone show a reduction rate of more than 90% for Escherichia coli and Staphylococcus aureus bacteria. Our computational docking studies also reveal strong binding interactions between the original carvone monomer and both bacteria. The study suggests that these AP plasma-produced coatings have great potential as antibacterial coatings for biomedical devices. [ABSTRACT FROM AUTHOR]

Simple Summary: In the last 50 years, limited modern drugs with new mechanisms of action have been incorporated; consequently, drug resistance has increased worldwide. Thus, the search for alternative pharmacological tools is a priority in ruminant production systems. Historically, natural products have played a relevant role in drug discovery. The anthelmintic activity of various phytochemicals has mainly been studied in vitro, whereas the in vivo characterization of their pharmacological properties is a challenge for upcoming years. The administration route and pharmaceutical formulation directly influence the drug concentration attained in the target parasites and, therefore, the resultant pharmacological effect. Here, we conducted an integrated pharmacological study to evaluate the combined administration of ivermectin and carvone to lambs infected with resistant nematodes. Although carvone showed a moderate in vivo anthelmintic effect and enhanced the ivermectin systemic availability after their coadministration in lambs, the concentrations attained in target tissues and in parasites were not sufficient for obtaining optimal efficacy. Innovative pharmaceutical formulations are necessary to establish phytochemicals as a useful pharmacological tool for controlling nematodes in ruminants. A wide variety of plant-derived phytochemicals with anthelmintic effects have been described. Most of them have shown activity against parasites in vitro but have not been extensively explored in vivo. The aim of the current work was to study the pharmacokinetic–pharmacodynamic relationship of the combined administration of carvone (R-CNE) and ivermectin (IVM) to lambs. Three trials were conducted to evaluate the pharmacological interaction between R-CNE and IVM in lambs infected with resistant nematodes. Drug concentrations were measured in plasma, target tissues, and H. contortus by HPLC with fluorescent (IVM) and ultraviolet (R-CNE) detection. The effect of both compounds on parasites was estimated by the fecal egg count reduction. Coadministration with R-CNE significantly increased the plasma bioavailability of IVM. R-CNE showed a moderate anthelmintic effect, which was greater on the susceptible isolate of H. contortus. After the combination of R-CNE and IVM as an oral emulsion, both compounds were quantified in H. contortus recovered from infected lambs. However, R-CNE concentrations were much lower than those reported to achieve anthelmintic effects in the in vitro assays. Optimization of the pharmaceutical formulation, dose rate, and administration schedule is needed to take advantage of the intrinsic anthelmintic activity of phytochemicals. [ABSTRACT FROM AUTHOR]

• The most abundant compounds found in the mentha species were D-carvone, menthofurane, and linalyl acetate, respectively. • The mentha species show antimicrobial activity. • The mentha species exhibit anticancer properties against different tumor cell lines. The objective of this study was to evaluate the antibacterial and antifungal activities, and cytotoxic effects of the essential oils (EOs) from Mentha spicata, M. aquatica, M. longifolia , and M. × piperita collected at three developmental stages. According to principal component analysis, carvone, menthofuran, and linalyl acetate were the distinctive major components of M. spicata (57.7–65.6%) and M. longifolia (64.7–72%), M. aquatica (23–52.4%), and M. × piperita (50.6–70.2%) EOs, respectively. Zone of inhibition (ZI) around EOs for bacterial strains ranged from 9 mm (against Klebsiella pneumonia) to 26 mm (against Staphylococcus aureus). For fungal strains, EOs were highly active towards Aspergillus niger showing ZI ranging from 23 mm (M. × piperita) to 28 mm (M. aquatica), while Candida albicans was markedly more resistant, giving ZI ranging from 11 mm (M. × piperita) to 14 mm (M. aquatica). Essential oils were active toward both Gram-positive and Gram-negative bacterial pathogens, with a MIC range from 20 µg mL−1 (in M. aquatica and M. longifolia against S. aureus) to 70 µg mL−1 (in M. × piperita against K. pneumonia). The lowest and highest MIC of the oils against fungal strains were recorded on A. niger (30.0 µg mL−1) and C. albicans (80.0 µg mL−1), respectively. Essential oils exhibited strong cytotoxicity to the cancer cell lines while being almost nontoxic toward normal cells. The most and the least active Mentha species were M. aquatica against MCF-7 (IC 50 : 36±1.9 μg/mL) and M. × piperita against A549 (IC 50 : 68±1.8 μg/mL), respectively. Overall, M. aquatica could be a good candidate for future supplementary studies. [ABSTRACT FROM AUTHOR]

Tissue engineering products have grown in popularity as a therapeutic approach for chronic wounds and burns. However, some drawbacks include additional steps and a lack of antibacterial capacities, both of which need to be addressed to treat wounds effectively. This study aimed to develop an acellular, ready-to-use ovine tendon collagen type I (OTC-I) bioscaffold with an antibacterial coating for the immediate treatment of skin wounds and to prevent infection post-implantation. Two types of crosslinkers, 0.1% genipin (GNP) and dehydrothermal treatment (DHT), were explored to optimise the material strength and biodegradability compared with a non-crosslinked (OTC) control. Carvone plasma polymerisation (ppCar) was conducted to deposit an antibacterial protective coating. Various parameters were performed to investigate the physicochemical properties, mechanical properties, microstructures, biodegradability, thermal stability, surface wettability, antibacterial activity and biocompatibility of the scaffolds on human skin cells between the different crosslinkers, with and without plasma polymerisation. GNP is a better crosslinker than DHT because it demonstrated better physicochemical properties (27.33 ± 5.69% vs. 43 ± 7.64% shrinkage), mechanical properties (0.15 ± 0.15 MPa vs. 0.07 ± 0.08 MPa), swelling (2453 ± 419.2% vs. 1535 ± 392.9%), biodegradation (0.06 ± 0.06 mg/h vs. 0.15 ± 0.16 mg/h), microstructure and biocompatibility. Similarly, its ppCar counterpart, GNPppCar, presents promising results as a biomaterial with enhanced antibacterial properties. Plasma-polymerised carvone on a crosslinked collagen scaffold could also support human skin cell proliferation and viability while preventing infection. Thus, GNPppCar has potential for the rapid treatment of healing wounds. [ABSTRACT FROM AUTHOR]

A field experiment was conducted to study the effect of three levels of seeding rate (4.7 and 10 kg·h-1) and three concentrations of licorice extract (0.3 and 6 g·L-1) the data were analyzed statistically by using a factorial experiment according to the randomized complete block design (RCBD) with three replicates. The results showed that the seeding rate 7 kg·h-1 gave a significant increase in seeds yield, volatile oil yield, and limonene ratio, which were 1162.6 kg·h-1, 25.6 kg·h-1, and 30.41%, respectively. In turn, seeding rate 4 kg·h-1 gave a higher average of the volatile oil percent and carvone percent, which were 2.3 % and 67.27%, respectively. The results also revealed that spraying of licorice extract with 3 g·L-1 gave significantly influenced in seeds yield and volatile oil yield which were (1016.6 and 23.3 kg·h-1) respectively, whereas the spraying of licorice extract with 6 g·L-1 gave the highest ratio of carvone and limonene which were 29.71% and 67.54% respectively. The interaction between the seeding rate of 7 kg·h-1 and licorice extract with 3 g·L-1 had a significant effect on seeds yield and volatile oil yield, which amounted to (1234.2 and 28.4 kg·h-1), respectively. [ABSTRACT FROM AUTHOR]

In this study, the biotransformation of carvone and camphor by Aspergillus flavus and the products were investigated. The biotransformation reaction of carvone by A. flavus resulted in the production of neodihydrocarveol, dihydrocarvone, 2-cyclohexene-1-one,2-methyl-5-(1-methylethenyl), limonene-1,2-diol, trans-p-mentha-1(7),8-dien-2-ol, p-menth-8(10)-ene-2,9-diol, and the biotransformation reaction of camphor resulted in the production of 2 -campholenic acid, 2-cyclohexene-1-one,2-hydroxy-4,4,6,6-tetramethyl, α-campholene aldehyde. The naturally produced essential oils by biotransformation of carvone and camphor were observed to be cytotoxic to breast cancer cells while no significant inhibition was seen in the healthy cell line. Additionally, biotransformation products had the highest inhibition (74%) against aflatoxin B1. The bioactivities of biotransformation products are promising, and they can be further investigated for their therapeutic potential as active agents. [ABSTRACT FROM AUTHOR]

Background: Carvone (l‐carvone) is a mint‐tasting flavour additive that most of us is exposed to and can cause allergic contact reactions. Objectives: To analyse the frequency and the relevance of positive carvone reactions in a dermatitis population. Method: A retrospective analysis of dermatitis patients consecutively tested with carvone from 2017 to 2021. Data were retrieved from the department's patch‐test database. Results: Of 3554 patients tested with carvone, 28 (0.79%) had a positive reaction. Carvone‐positive patients had higher mean age, were significantly more likely female (p < 0.001) and had often an intraoral/lip involvement (p < 0.001). In the carvone‐positive group, 50% (n = 14) had a relevant reaction, and in 4 of 14, the relevance was first revealed after test reading. Of the carvone‐positive patients, 18 of 28 did not have a coexisting allergy to a fragrance/flavour allergen and of these 44% had a relevant allergy. Conclusions: The study suggests that a significant fraction of relevant carvone contact allergies may be overlooked if the allergen is not tested. Furthermore, as the exposure is widespread, inclusion of carvone in the Swedish baseline series may be justified even if the contact allergy prevalence is below 1%. [ABSTRACT FROM AUTHOR]

The cosmetics and food fields are based on the use of synthetic substances to protect their products against oxidation. However, synthetic antioxidants were reported to have negative effects on human health. The interest to develop natural antioxidants from plants has been growing in recent decades. The aim of this study was to determine the antioxidant properties of three essential oils (EOs) of M. pulegium (L.), M. suaveolens (Ehrh.) and M. spicata (L.) from the Azrou and Ifrane regions. The organoleptic characteristics, yields and physical properties were determined for the selected EOs. Their chemical compositions were identified using GC-MS; then, their antioxidant activities were evaluated using the DPPH• free radical scavenging activity and were compared with the ascorbic acid standard. The determined physicochemical parameters of dry matter and EOs demonstrated their good quality. The analysis of the EOs showed the dominance of pulegone (68.86–70.92%) and piperitenone (24.81%), piperitenone oxide (74.69–60.3%), and carvone (71.56–54.79%) and limonene (10.5–9.69%) for M. pulegium, M. suaveolens and M. spicata, respectively, from Azrou and Ifrane. Additionally, the antiradical tests demonstrated the remarkable power of these EOs, especially M. pulegium EO (IC50 = 15.93 mg/mL), which recorded the best activity compared with ascorbic acid (IC50 = 8.849 mg/mL). The obtained results indicated that these EOs could be applied as natural antioxidants in the food industry. [ABSTRACT FROM AUTHOR]

The chemical modification of natural compounds is a promising strategy to improve their frequently poor bioavailability and low potency. This study aimed at synthesizing chemical derivatives of carvone, a natural monoterpene with anti-inflammatory properties, which we recently identified, and evaluating their potential anti-inflammatory activity. Fourteen chemical derivatives of carvone were synthesized, purified and their chemical structures confirmed. Noncytotoxic concentrations of the test compounds were selected based on the resazurin reduction assay. Among the tested compounds, four significantly reduced the lipopolysaccharides-induced protein levels of the inducible isoform of the nitric oxide synthase and nitric oxide production and showed a dual effect on pro-IL-1 protein levels in the Raw 264.7 cell line. The Ligand Express drug discovery platform was used to predict the targets of the test compounds, and an enrichment analysis was performed to group the different biological processes and molecular and cellular functions of the tested compounds. Moreover, Ligand Express also predicted that all chemicals evaluated have intestinal and blood–brain barrier permeability, do not inhibit P-gp and do not interact with major receptors. Although presenting anti-inflammatory and some advantageous ADME properties, the tested compounds still have low potency and specificity but may provide novel structures the further chemical modification of which may yield more promising drugs. [ABSTRACT FROM AUTHOR]

This study examined the effects of ultrasonic treatment on the amount and quality of essential oils extracted from caraway seeds using ultrasonic treatment followed by hydro-distillation and ultrasonic treatment followed by microwave-assisted hydro-distillation. Afterward, the obtained results were compared with those of untreated extracts issued from conventional hydro-distillation and microwave-assisted hydro-distillation. The essential oil yields ranged from 1.18 ± 0.09 to 1.36 ± 0.09% w/w, depending on the extraction technique. Analysis by gas chromatography coupled with mass spectrometry showed the presence of 21 compounds in all the extracts. Produced essential oils consisted of 9.65 ± 1.742 % to 18.59 ± 1.377 % monoterpenes hydrocarbons and 77.20 ± 2.847 to 84.60 ± 1.909 % oxygenated monoterpenes. The main components were limonene and carvone, but the amounts of each component depend on the methods. Additionally, the antioxidant activity of caraway seeds essential oils was determined using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay. The antioxidant ability of the examined oils was moderate, and the USMAHD oil median inhibitory concentration (IC50) value was the lowest. Moreover, a statistical investigation paved the way for a possible correlation between the carvone/limonene ratio and IC50. Consequently, this aspect, which is the potential for improving the extract's quality by modifying the ratio of the target components known for their high antioxidant effects, made this study novel. [ABSTRACT FROM AUTHOR]

Herein, the chemical profiles of the essential oils and volatiles obtained from the aerial parts of Mentha pulegium L. (Lamiaceae) are reported respectively using microwave-assisted hydrodistillation (MAHD) and headspace solid phase microextraction (HS-SPME) approaches associated to gas chromatography-mass spectrometric (GC-MS) quantification. Using MAHD-GC-MS and HS-SPME-GC-MS techniques, 30 and 28 constituents were screened in the essential oils and volatiles of M. pulegium L. aerial parts with high prevalence of oxygenated monoterpenes and non-terpene hydrocarbons, respectively. Accordingly, in the characterized chemical profiles, carvone was found to constitute about 56.0% of the oil using the former technique (MAHD), whereas oleic acid (20.1%), carvone (17.7%) along with limonene (16.1%) were found as the major constituent components of the volatile profile using the latter approach (SPME). The two methods might be used in combination to obtain a wider set of information about the chemical composition of one specific plant sample. [ABSTRACT FROM AUTHOR]

The genus Teucrium L., belonging to the family Lamiaceae, is divided in ten sections including Polium (Mill.) Schreb. In Cyprus, this section is represented by five endemic species: T. micropodioides, T. cyprium, T. karpasiticum, T. kyreniae and T. salaminium. Essential oils of the aerial parts of these species were separately obtained by hydrodistillation using a Clevenger-type apparatus. Chemical compositions of the obtained oils were analyzed by GC and GC/MS, simultaneously. The essential oil yields ranged between 0.03-0.75 (v/w). The major components of the essential oil of T. kyreniae were ß-caryophyllene (21.2%), (E)-nerolidol (10.9%), carvone (8.8%) and a-humulene (7.9%). T. salaminium essential oil was dominated by ß-caryophyllene (15.2%), caryophyllene oxide (13.9%), germacrene D (11.6%) and bicyclogermacrene (10.0%). Major components of the oil of T. cyprium were ß-pinene (35.4%), a-pinene (10.6%) and spathulenol (8.4%). Major compounds of the oils of T. micropodioides samples, collected from two different locations, were (1) limonene (47.0%), ß-pinene (16.0%) and ß-caryophyllene (6.9%), (2) d-cadinene (11.2%), 1-epi-cubenol (7.8%), cubebol (4.7%), cubenol (4.1%), respectively. Main constituents of the essential oil of T. karpasiticum were limonene (43.9%), ß-pinene (16.0%), a-bisabolol oxide A (7.8%), ß-caryophyllene (5.5%) and a-pinene (4.6%). The section Polium, is considered a complex and the diversity of oil compositions from the species belonging to this section provided additional proof to this consideration. [ABSTRACT FROM AUTHOR]

Following a request from the European Commission, EFSA was asked to deliver a scientific opinion on the safety and efficacy of a tincture from the fruit of Anethum graveolens L. (dill tincture) when used as a sensory additive in feed and water for drinking for all animal species. The product is a ■■■■■ solution, with a dry matter content of approximately 0.9%. The product contained 0.0247% polyphenols (of which 0.0137% were flavonoids) and 0.003% carvone. Estragole was present at concentrations between the limit of detection and the limit of quantification in the five batches examined. The Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) concluded that the dill tincture is safe at the maximum proposed use levels of 200 mg/kg complete feed for horses and 50 mg/kg complete feed for all other animal species. The FEEDAP Panel considered that the use in water for drinking is safe provided that the total daily intake of the additive does not exceed the daily amount which is considered safe when consumed via feed. No safety concern would arise for the consumer from the use of dill tincture up to the maximum proposed use levels in feed. Dill tincture should be considered as irritant to skin and eyes, and as a dermal and respiratory sensitiser. When handling the additive, exposure of unprotected users to estragole cannot be excluded. Therefore, to reduce the risk, the exposure of the users should be minimised. The use of dill tincture as a flavour in animal feed was not expected to pose a risk for the environment. Since the fruit of A. graveolens and its preparations were recognised to flavour food and their function in feed would be essentially the same as that in food, no further demonstration of efficacy was considered necessary. [ABSTRACT FROM AUTHOR]

Comparative research has been conducted to determine the content of heavy metals and chemical composition of costmary oils, as well as to identify the possibility of costmary (Tanacetum Balsamita L.)| growth on soils contaminated by heavy metals. Costmary is a plant tolerant of heavy metals and can be grown on contaminated soils. Heavy metals do not affect the development of costmary and the quality of oil obtained from it. Twenty-three components were identified, accounting for 98.26-98.99% of the total oil components. The major components (> 1.0%) contained in costmary oil are carvone (42.66-44.12%), alpha-thujone (29.81-30.07%), beta-bisabolene (5.51-6.24%), 1,8-cineole (2.71-3.58%), beta-thujone (2.47-2.60%), cis-para-mentha-1(7),8-dien-2-ol (1,63-1,72%), trans-para-mentha-2,8-dienol (1.34-1.41%), cis-carveol (1.20-1.74%), and gamma-muurolene (1.69-1.78%). The content of oxygen-containing monoterpenes (88.75-89.41%) is the highest in costmary oil, followed by sesquiterpene hydrocarbons (7.74-8.35%), oxygen-containing sesquiterpenes (1.0-1.06%) and monoterpene hydrocarbons (0.58-0.61%). The analysed costmary oils belong to the carvone - a-thujone chemotype. [ABSTRACT FROM AUTHOR]

• Use of the bio-renewable olefin, (R)-carvone makes the hydroformylation process sustainable. • The system is extremely sensitive to changes in the reaction conditions which necessitates rigorous optimizations. • Employment of Rh/Xantphos catalytic system leads to an aldehyde favoring approach. • Selectivity tuning gives 99 % conversion, 95 % yield and 96 % chemoselectivity toward the desired aldehyde under optimized conditions. • The formation of only the linear aldehyde makes the system regiospecific. An efficient protocol for the rhodium catalyzed single-step hydroformylation of renewable natural olefin, (R)-carvone was developed, obtaining the corresponding linear aldehyde as the major product. The system was found to be highly sensitive to even slight variations in the reaction conditions, which had a tendency to complicate itself through the formation of numerous byproducts; nonetheless, high conversion (99 %), yield (95 %) and chemoselectivity (96 %) toward the desired aldehyde were accomplished under the optimized conditions. Moreover, this process proved to be regiospecific as no branched aldehyde was formed. These results were achieved by a careful tuning of different parameters such as temperature, pressure, reaction time, catalyst to ligand ratio, catalyst to substrate ratio and types of catalyst precursors, ligands and solvents. [Display omitted] [ABSTRACT FROM AUTHOR]

Spearmint (Mentha spicata L.) is popular for its medicinal benefits and industrial uses, in this study forty-three half-sib progenies were evaluated over three seasons at CSIR-CIMAP, Research Centre Pantnagar to study genetic variability, correlation, path coefficient analysis and Mahalanobis D2 diversity by using five morphological and two biochemical traits. These forty-three half-sib populations were derived from nine commercially existing spearmint varieties through an intra-population improvement method. Results of correlation and path coefficient studies indicated the paramount importance of certain key traits in the selection process. Notably, traits such as herb yield per plot (kg), plant height (cm) and oil content (%) emerged as pivotal, exhibiting positive correlations, high heritability and moderate to high genetic advance. These attributes, therefore need primacy in the selection of superior lines. Furthermore, genotypes OPSP-106, OPSP-92, OPSP-47, OPSP-35 and OPSP-76 showed significant genetic divergence. These accessions hold promise as parent candidates for hybridization experiments aimed at finding transgressive segregants in later generations. Additionally, this study highlighted the presence of specific oil components, such as carvone and limonene, offering insights into potential avenues for targeted breeding efforts. This study provides a holistic view of the genetic makeup of Mentha spicata genotypes, enabling informed decisions in breeding programs. By prioritizing traits and maximizing genetic diversity, the results of this investigation will contribute to the development of improved spearmint varieties with enhanced morphological and biochemical characters, thus advancing the medicinal and industrial applications of spearmint. [Display omitted] • Key traits like herb yield, plant height, and oil content correlated positively. • Improvement in plant height, herb yield, oil content improves oil yield. • Genotypes OPSP-106, −92, −47, −35, −76 are diverse and used for hybridization. • Carvone and limonene-enriched lines are good for transgressive breeding • Selection among diverse half-sibs will boost spearmint oil yield. [ABSTRACT FROM AUTHOR]

[Display omitted] • Adsorption of carvone molecules on Ag 13 - and Ag 13 + nanoclusters were stable. • Adsorption of carvone molecules onto Ag 13 - and Ag 13 + nanoclusters increased the polarity of the complexes. • The UV–Vis analysis showed the red-shifted absorption of [silver-nanocluster] complexes. New chemical drugs have challenges like adverse side effects and drug release. Essential oils have applications in drug production but face limitations like solubility and instability. On the other hands, silver nanoparticles have a crucial role in the medical field. They find applications in wound dressings, medical equipment, and implant coatings. Their outstanding antimicrobial properties make them highly effective against a wide range of microorganisms. Therefore, in this study, the potential of silver nanoclusters as drug delivery vehicles was closely examined using density functional theory (DFT) computational methods. Specifically, the Ag 13 , Ag 13 -, and Ag 13 + nanoclusters were considered as nano-carriers for the (5R)-(−)-carvone and (5S)-(+)-carvone molecules in the gas, water, and ethanol phases. The interaction between carvone molecules and silver nanoclusters was analyzed using DFT, quantum theory of atoms in molecules (QTAIM), the electron localization function (ELF), localized orbital locator (LOL), and density of states (DOS) methods. The results showed that the adsorption of carvone on cationic and anionic silver nanoclusters is stable, with negative adsorption energy, while adsorption on neutral nanoclusters is unstable. Weak non-covalent interactions were found between carvone and cationic/anionic nanoclusters in solvent phases, facilitating drug delivery. Adsorption on Ag 13 - and Ag 13 + increased the polarity of the complexes, allowing solubility in polar solvents suitable for biological applications. The UV–Vis analysis showed the red-shifted absorption of [silver-nanocluster] complexes can be used for online detection of carvone compounds. Vibrational frequency calculations indicated the [silver-carvone] complexes are structurally stable, with changes in frequencies due to carvone adsorption, useful for complex identification. The molecular docking results indicated that [silver-carvone] complexes are more suitable for target receptor interactions compared to carvone alone. Consequently, the [silver-carvone] complexes exhibited suitable anti-inflammatory, anticancer, and antimicrobial activities. Notably, the anticancer activity was greater than antibacterial, which was higher than anti-inflammatory. These findings suggest the [silver-carvone] complexes have the potential to be an effective anticancer, antibacterial, and anti-inflammatory drug candidate for treating various diseases. [ABSTRACT FROM AUTHOR]

This study investigated the efficacy of carvone, abscisic acid (ABA), gibberellin (GA3), and variable temperature in managing dormancy and sprouting in aeroponically grown mini-tuber potato (Solanum tuberosum L.) seeds. The results showed that carvone treatment effectively reduced the weight loss rate by 12.25% and decay rate by 3.33% at day 25 compared to control. ABA treatment significantly enhanced the germination rate, increasing it to 97.33%. GA3 treatment resulted in the longest sprouts of 14.24 mm and reduced the MDA content by 23.08% at day 30, indicating its potential in shortening dormancy and maintaining membrane integrity. The variable-temperature treatment demonstrated a balanced performance in reducing weight loss and maintaining a lower relative conductivity, indicating less cellular damage. The enzymatic activities of α-amylase, CAT, and SOD were modulated by the treatments, ensuring a balanced enzymatic environment for seed vitality. These results establish a solid basis for improving postharvest management strategies to optimize germination uniformity and preserve the quality of aeroponic potato seeds during extended dormancy, promising enhanced yield and productivity in potato cultivation.

Carvone and spearmint essential oil vapours are suitable candidates for the control of citrus postharvest pathogens due to their strong antifungal activity. However, the high volatility of essential oils remains a hurdle that needs to be overcome before it can be applied as an alternative fungicide. This work investigates the antifungal activity of 20 and 30 wt-% spearmint essential oil or carvone, incorporated into ethylene–vinyl acetate (EVA) and linear low-density polyethylene (LLDPE) strands postharvest pathogens affecting kumquats. Following the melt-extrusion process, an average yield of 16–29 % and 15–28 % of the total carvone and spearmint essential oil, respectively, was determined in the polymer strands. Morphological studies using scanning electron microscopy (SEM) revealed the presence of microporous structures in the internal structure of the strands. The membrane-like skin that covers the polymer strand was also confirmed by SEM. Variations in the release rates were observed between carvone and spearmint essential oils, which was attributed to the difference in the vapour pressure of the neat essential oils. Furthermore, in this study, the results demonstrated that the diffusion exponent ‘n’ of the Korsmeyer–Peppas, Weibull and Log-logistic models exceeded 1.0. In most cases, the Super Case II mechanism was observed. In the case of the Mapossa model, as k2 was ˃> 1, it implies that the outer skin-like membrane covering the polymer strand fully controlled the carvone release. The application of the essential oil-loaded polymer strands resulted in a significant reduction in deterioration, caused by citrus postharvest pathogens, of kumquats kept at room temperature for 21 days. This study indicates that the incorporation of spearmint essential oil or carvone into LLDPE or EVA polymer strands promoted the preservation of kumquat over a 21-day period.

Abstract Following a request from the European Commission, EFSA was asked to deliver a scientific opinion on the safety and efficacy of a tincture from the fruit of Anethum graveolens L. (dill tincture) when used as a sensory additive in feed and water for drinking for all animal species. The product is a ■■■■■ solution, with a dry matter content of approximately 0.9%. The product contained 0.0247% polyphenols (of which 0.0137% were flavonoids) and 0.003% carvone. Estragole was present at concentrations between the limit of detection and the limit of quantification in the five batches examined. The Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) concluded that the dill tincture is safe at the maximum proposed use levels of 200 mg/kg complete feed for horses and 50 mg/kg complete feed for all other animal species. The FEEDAP Panel considered that the use in water for drinking is safe provided that the total daily intake of the additive does not exceed the daily amount which is considered safe when consumed via feed. No safety concern would arise for the consumer from the use of dill tincture up to the maximum proposed use levels in feed. Dill tincture should be considered as irritant to skin and eyes, and as a dermal and respiratory sensitiser. When handling the additive, exposure of unprotected users to estragole cannot be excluded. Therefore, to reduce the risk, the exposure of the users should be minimised. The use of dill tincture as a flavour in animal feed was not expected to pose a risk for the environment. Since the fruit of A. graveolens and its preparations were recognised to flavour food and their function in feed would be essentially the same as that in food, no further demonstration of efficacy was considered necessary.