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Clinopodium mexicanum (CM) has been used by the population as a home remedy for inducing sleep, and as a sedative and analgesic. This study presents the first evaluation of the antioxidant activity of the essential oil (EO) obtained through hydrodistillation of the aerial parts of CM. NaCl, CaCl2, and Tween 20 were used as additives and the yield, chemical composition, and toxicity of the EO were evaluated. The findings revealed that the highest yield of EO was obtained through hydrodistillation without additives, and the additives significantly influenced the antioxidant activity of the EO. The main components of the EO were found to be pulegone and menthone. The toxicity of the EO was determined using the brine shrimp assay, with an LD50 of 32 mg/L. Based on these results, the authors suggest that the Clinopodium mexicanum EO has the potential to serve as a natural antioxidant. [ABSTRACT FROM AUTHOR]

Ziziphora clinopodioides L. is a valuable medicinal and aromatic plant; however, its special requirements for proper growth and enhanced secondary metabolite composition have limited its production and availability. The lack of appropriate fertilizer dosage recommendations is one of these limiting factors for ex situ conservation and large-scale cultivation. This study investigated the effects of nitrogen (N) fertilization on Z. clinopodioides in both open field and unheated greenhouse conditions. The determined research factor was N dosage (0, 40, 80, and 120 kg N ha−1 in the field) and (0, 200, 400, and 600 mg N pot−1 in the greenhouse). It was found that Z. clinopodioides plants could grow successfully outside their natural habitat with sufficient N fertilization yielding a satisfactory amount of metabolites per plantation area. Specifically, among the tested dosages, the 120 kg N ha−1 (which showed no significant difference from 80 kg N ha−1) and 400 mg N pot−1 fertilizers increased the aboveground dry and fresh biomass, essential oil (EO) content, and yield. Nitrogen fertilization showed a direct correlation with menthone, neo-menthol, menthol, pulegone, E-ocimenone, and spathulenol, but a negative correlation with α-pinene, β-pinene, limonene, 1,8-cineol, trans-pulegol, and iso-menthone. This study is the first to evaluate the effects of N fertilization on the genus Ziziphora. The results indicate that utilizing N fertilizer at a moderate rate (80 kg N ha−1 in the field and 400 mg N pot−1 in the greenhouse) can improve the agronomic traits and EO of Z. clinopodioides. [ABSTRACT FROM AUTHOR]

In this study, the odour values of rosemary, mint, black cumin, lavender, and thyme oils were determined by an electronic nose working with an Arduino microprocessor. The components of the plants were compared with the sensor data, and the most sensitive sensors were determined by sorting according to the highest components. The study data indicated that the MQ3 sensor exhibited the highest sensitivity for thyme, black cumin, and lavender oils, which contain 63% carvacrol, 38% thymoquinone, and 36% linalool, respectively. Also, MQ7 was the most sensitive sensor for menthone (68%) in mint oil and eucalyptol (45%) in rosemary oil. In addition, a low-cost and non-contact device that works with an infrared sensor has been developed to detect the identity of the oil added into the vial. The study data showed that low-cost Arduino-based IR and odour sensors can determine the identity and component percentage of oils. The fact that the developed device can detect with 100 percent accuracy even in case of peppermint and rosemary oils, which are very similar in appearance, shows that the study data will be an inspiration for contactless determination of oil quality and type. [ABSTRACT FROM AUTHOR]

Mexican Coccoloba uvifera fruit contains polyphenols, flavonoids, and anthocyanins, while in the leaves, lupeol, α- and β-amyrin have been previously identified by HPLC. However, the low resolution by HPLC of pentacyclic triterpenes (PTs) is a limitation. Moreover, the volatile profile of C. uvifera fruit is still unknown. Therefore, this study aimed to identify PTs in C. uvifera leaf and fruit extracts by CG-MS analysis and to determine the volatile profile of C. uvifera pulp by headspace solid-phase microextraction. The results showed trimethylsilylated compounds of standards lupeol, α- and β-amyrin, indicating that the silylation reaction was suitable. These trimethylsilylated compounds were identified in leaf and fruit extracts. The fruit volatile profile revealed the presence of 278 esters, 20 terpenes, 9 aldehydes, 5 alcohols, and 4 ketones. The fruit showed a high content of esters and terpenes. Due to their flavour properties, esters are essential for the food, cosmetics, and pharmaceutics industries. Moreover, terpenes in the fruit, such as menthone, β-elemene, junipene, and β-caryophyllene have the potential as anticancer and phytopathogen agents. The results indicated that GC-MS is an alternative to HPLC approaches for identifying PTs. Besides, identifying volatile compounds in the fruit will increase the value of this plant and expand its application. Identifying PTs and volatile compounds in Mexican C. uvifera leads to a better understanding of the potential benefits of this plant. This would increase the consumption of Mexican C. uvifera fresh or as functional ingredients in nutraceutical or pharmaceutical products. [ABSTRACT FROM AUTHOR]

Peppermint is one of the valuable plants in the pharmaceutical industry. The reduction of water in Iran is one of the most important production limitations. The use of organic materials such as humic acid and wood vinegar can be useful to help produce medicinal plants to reduce the effects of drought stress. This research was carried out in order to investigate the effect of humic acid and wood vinegar foliar spraying on plant traits and main compounds of peppermint essential oil under drought stress conditions. A filed experiment was conducted as a split plot based on a randomized complete block design with three replications in the research farm of the Faculty of Agriculture of the Tarbiat Modares University in 2019. The experimental treatments included low irrigation regime at three levels (irrigation up to the field capacity and respectively after draining 25 (no stress), 40 (moderate drought stress) and 55 (severe drought stress) percentage of available water in the root zone) as the main plots factor was foliar application at seven levels (humic acid (1, 2, and 3%), wood vinegar (5, 10, and 15%) and no foliar application (control)) as a sub plots. The results showed that the interaction of foliar application and irrigation regimes had a significant effect on plant height, total dry weight, total chlorophyll, flavonoid, total phenol, essential oil percentage and yield, and essential oil profile. Maximum total dry weight was produced with foliar spraying of 2 and 3% humic acid in normal irrigation conditions with 3204 and 3259 kg ha-1, respectively, and moderate and severe water deficit stress, respectively, caused a decrease of 15.34 and 27.42% of the total dry weight compared to the control. Water deficit stress harmed the yield of essential oil; so that with the increase of the stress intensity, its value decreased, and moderate and severe water deficit stress, a decrease of 9.38 and 40.2 percent of essential oil yield, respectively, was observed. Increasing the concentration of humic acid from zero to 3% increased the total chlorophyll by 10.4%. The flavonoids increased by 14.6, 22.5, and 33.1 percent with the use of 1, 2, and 3 percent humic acid, respectively, and this increase with the use of 5, 10, and 15 percent wood vinegar was 14.3, 34.7, and 37.1 percent, respectively. It was 34.34 and 37.15 percent. By increasing the concentration of humic acid from zero to 3%, the essential oil content increased by 60.6%. While increasing the concentration of wood vinegar from zero to 15%, its amount increased by 90.7%. The highest amount of menthol was obtained from the application of 10% wood vinegar in normal irrigation conditions at 61.04%, and it was placed in a statistical group with the treatment of 2% humic acid application in moderate water stress conditions (60.1%). In addition, the results showed that with the use of humic acid and wood vinegar, the amount of menthol increased by 21.88 and 17.84%, respectively, compared to not using them. According to the water limitation and the results of this research, it is recommended to use 3% humic acid in optimal irrigation conditions and moderate water deficit stress and use 15% wood vinegar in severe water deficit stress conditions. [ABSTRACT FROM AUTHOR]

Analyzing exhaled breath for volatile organic compounds (VOCs) using thermal desorption–gas chromatography–mass spectrometry (TD-GC-MS) offers a non-invasive diagnostic approach for various diseases. Despite its promise, the method faces challenges like sampling heterogeneity and high costs. Following the European Respiratory Society's advocacy for methodological standardization, we developed the SPIRITAS (Standardized Product for Inexpensive Respiratory InvesTigation: A breath Sampler), a low-cost, disposable breath sampler. This study evaluates the SPIRITAS's effectiveness in detecting targeted VOCs. We tested the SPIRITAS using the Peppermint Experiment, a standardized protocol that allows for comparison between different breath sampling and analytical practices by assessing the ability to detect five peppermint-specific VOCs after ingestion of a 200-milligram peppermint oil capsule. We included ten subjects and performed six breath samples per participant, including a baseline measurement taken before ingestion. We used the Wilcoxon signed-rank test to evaluate whether baseline values were significantly lower than the peak values of the targeted VOCs. Additionally, we conducted an experiment utilizing humidified medical-grade air to identify any VOCs attributable to the SPIRITAS setup itself. Results showed successful detection of four out of five targeted "peppermint-associated" VOCs: alpha-pinene (p ≤ 0.01), beta-pinene (p ≤ 0.01), menthone (p = 0.01), and menthol (p = 0.02), indicating significant differences between the baseline and peak values in the volunteers' breath. However, detection of eucalyptol was inconsistent. In addition, we identified 16 VOCs that were released by the SPIRITAS, one of which remains unidentified. Our findings underscore the SPIRITAS's potential for clinical applications, paving the way for broader biomarker research. The combination of ease of use, low cost, reduced risk of contamination, and standardization makes SPIRITAS very suitable for large-scale international studies. Furthermore, we have demonstrated the SPIRITAS's effectiveness in detecting specific VOCs and identified 16 compounds originating from the SPIRITAS, ensuring that these compounds would not be mis-qualified as potential biomarkers in future clinical studies. [ABSTRACT FROM AUTHOR]

This present study aims to characterize the essential oil compositions of the aerial parts of M. spicata L. and endemic M. longifolia ssp. cyprica (Heinr. Braun) Harley by using GC-FID and GC/MS analyses simultaneously. In addition, it aims to perform multivariate statistical analysis by comparing with the existing literature, emphasizing the literature published within the last two decades, conducted on both species growing within the Mediterranean Basin. The major essential oil components of M. spicata were determined as carvone (67.8%) and limonene (10.6%), while the major compounds of M. longifolia ssp. cyprica essential oil were pulegone (64.8%) and 1,8-cineole (10.0%). As a result of statistical analysis, three clades were determined for M. spicata: a carvone-rich chemotype, a carvone/trans-carveol chemotype, and a pulegone/menthone chemotype, with the present study result belonging to the carvone-rich chemotype. Carvone was a primary determinant of chemotype, along with menthone, pulegone, and trans-carveol. In M. longifolia, the primary determinants of chemotype were identified as pulegone and menthone, with three chemotype clades being pulegone-rich, combined menthone/pulegone, and combined menthone/pulegone with caryophyllene enrichment. The primary determinants of chemotype were menthone, pulegone, and caryophyllene. The present study result belongs to pulegone-rich chemotype. [ABSTRACT FROM AUTHOR]

Introduction: Secondary metabolites have a complex structure which is produced by chemical bio-synthesis. Therefor, they are mostly extracted from wild or cultivated plants. The essences are natural, complex and volatile secondary metabolites which are mostly produced in medicinal and aromatic plants. Peppermint (Mentha piperita L.), a hybrid from M. aquatica and M. spicata, is an herbaceous and perennial plant belonging to Lamiaceae family. It is widely cultivated in temperate regions of Europe, Asia, America, India and Mediterranean countries due to its commercial value and unique odor. Materials and Methods: In order to investigate the influence of putrescine treatment at three levels including 0, 0.1 and 1 mM, and salicylic acid treatment at three levels including 0, 0.1 and 1 mM, on the yield performance and essence components of peppermint, a field factorial experiment was performed based on complete blocks design with three replications at Research Station of Tabriz University during 2019. Peppermint seedling were prepared from Agricultural Jihad Organization of Bostan Abad and cultivated at a distance of 30×30 cm. Foliar application of salicylic acid and putrescine was carried out twice during vegetative stage of plants (with one week interval). Harvesting and bio-chemical assessments were done at stage of 25 % flowering. The essential oil of peppermint was assessed to identify its main components. Results and Discussion: The results of the current study showed that the average yield of essential oil in plants treated with 1 mM salicylic acid was significantly increased compared to the control. A total of 24 compounds were identified in the essential oil of peppermint aerial parts. The main components of the essential oil were included menthone, menthol, L-menthol and 1,8-cineole. Menthone and menthol constituted 26.14 and 23.21 % of essential oil, respectively. Different concentrations of salicylic acid and putrescine increased the production rate of menthone, menthol, l-menthol and methyl acetate compounds in the essential oil compared to the control. The concentration of 1 mM salicylic acid had the greatest effect on the production of essential oil compounds. The correlation results between essential oil compounds showed that menthone has a positive and significant correlation with methyl acetate. Similarly, foliar application of salicylic acid (10 mM) and indole-3-acetic acid (1.5 mg L-1) increased the content of main component of peppermint and lemon balm. In the other study, foliar application of lemon balm plants with salicylic acid and putrescine caused a considerable increase in monoterpenes and sesquiterpenes content which was in line with obtained results of the present study. Conclusion: The plant growth regulators used in this research increased the yield and composition of the essential oil of aerial parts of peppermint, which shows that both salicylic acid and putrescine have a high potential in increasing the potency and chemical composition of the essential oil in the peppermint plant and probably in other aromatic crops. Therefore, foliar application of salicylic acid and putrescine during vegetative growth of peppermint could be introduced as influential technique to improve qualitative and quantitative characteristics of this aromatic and medicinal plant. [ABSTRACT FROM AUTHOR]

Mentha arvensis L. var. 'kosi', occasionally recognized as corn mint or field mint, belongs to the Lamiaceae family and is widely grown in temperate climates throughout Europe, western and central Asia, as well as North America for its medicinal significance (Aflatuni et al, 2005). The essential oil extracted from the mint plant reveals a rich assortment of secondary metabolites. Among these compounds are menthol, menthone, menthyl acetate, neomenthol, á-pinene, â-pinene, piperitone, limonene, tannins, and flavonoids. The recognition and analysis of these constituents contribute to a thorough understanding of the intricate chemical composition inherent in mint plant essential oil (Akram et al, 2011). The plant has long been utilized in Indian medicine to alleviate stomach problems, fevers, and headaches. The influence of phenolic compounds on antimicrobial, antibacterial and antioxidant activities, germination and early development of herbaceous woodland plants, and seed germination has sparked considerable attention. Menthol, obtained from the essential oil of the mint plant, is credited with therapeutic properties that effectively combat skin allergies. Additionally, it demonstrates diuretic properties and serves as an antiseptic and carminative agent. The authors observed that the stimulating effects of salicylic acid, methyl jasmonate and similar phenolic compounds can be used to increase the content present in the essential oil and medicinal and pharmacological values of the plants of the Lamiaceae family. This idea led us to try the other phenolic compounds' foliar application to various species of mint with an expectation to increase the quality of these plants. The present study had the goal to evaluate if the exogenous foliar application of different phenolic compounds (phenol, catechol, pyrogallol, picric acid and salicylic acid) at concentration of 1.0 mM can optimize the physiological, biochemical activities and essential oil production in 120-day-old mint plants. Growth and physiological, biochemical, and total essential oil content assessments inclusive of menthol, menthone, menthyl acetate indicated that 1.0 mM concentration of pyrogallol and salicylic acid were most potent at eliciting a general stimulation of mint metabolism. Overall, the findings demonstrate that salicylic acid and pyrogallol stimulate mint physiology and open up new avenues for biotechnological application on additional plant species with agronomic promise. [ABSTRACT FROM AUTHOR]

Introduction Mint has been used both as a medicinal and aromatic plant since ancient times. Peppermint volatile oil is one of the most important essential oils and has strong antimicrobial activity. The stage at which the maximum essential oil is obtained from the plant is not necessarily the stage at which the plant has the most biomass, therefore, the appropriate time for harvesting the plant should be determined according to the maximum amount of the effective substance and the yield of dry matter. In most of the methods of producing medicinal plants, quick access to the equipment for extracting effective substances is not possible, especially at high levels, and this requires drying a large part of the plants and extracting the effective substance in subsequent times. The quality of dried medicinal plants is defined by the content of their biologically active compounds. This study was aimed to determine the best time to harvest peppermint and the effect of different drying methods on the shoots biochemical compounds. Materials and MethodsIn order to increase the yield of peppermint medicinal plant essential oil, two separate experiments were designed and conducted in Shirvan Higher Education Complex (N 26 37', E 45 57', altitude 1067 m) in 2015. The aim of first experiment was finding the best harvest time at three levels (Before flowering, at flowering 50 and 100%) and the second experiment was finding the best method for shoot drying with nine levels (Microwave radiation at 90, 180, 360, 600 and 900 watts; Oven at 40 and 60°C; Shade; and Sun), were based on a completely randomized block design (CRBD) and a completely randomized design (CRD), respectively. In the spring of 2015, tillage operations were carried out and after preparing the land, 9 plots (2 × 3 meters) were created in it. The distance between the plots was considered 1.5 m. Rizhomes of peppermint plant was obtained from Mashhad Agricultural and Natural Resources Research Center and transplanted at 20 × 30 cm intervals on May 26. Some morpholocial and biochemical traits were measured. Essential oil extraction was done by distillation method with water and essential oil components were determined by GC/Mass method. Results and DiscussionThe effect of harvesting time was significant (p≤0.01) on the plant height, number of leaves per plant, wet and dry yield of peppermint plant. The height of the plant after 50% flowering stage did not show any significant difference, but the other investigated traits include the number of leaves per plant, the wet and dry yield of the plant, the yield of essential oil in terms of wet and dry weight, and the inhibition of free radicals in the branches in shoots harvested at the time of full flowering had the highest amount, which showed a statistically significant difference. The yield of essential oil in terms of dry matter in the full flower stage increased 1.8 times compared to the 50% flowering stage and 4.6 times compared to the pre-flowering stage. The percentage of essential oil components was also affected by the harvest time, and the highest amount was observed in the full flowering stage (98.92 percent), include the highest amount in menthol (42.39 percent) and menthone (19.13 percent). The use of micro rays caused the shortest drying time, so that with the increase of power of micro rays, the drying time decreased and the shoots were dried in 0.16 hours at the power of 900 watts. The oven application at 60 and 40 °C were statistically ranked second and third in terms of drying speed with 10 and 14.6 hours. Sun and shade drying needed 46 and 109.6 hours to reach constant moisture, respectively. The highest amount of essential oil was obtained in the shade drying method (2.13%) and the lowest amount was observed in the microwave application at 900 and 600 watt. (0.01%). After shade drying, the highest amount of essential oil was observed in the oven method at 40 °C (2%) and in the sun drying (1.44%). According to the results of this study, it is recommended to harvest the branches at the time of full flowering and dry them using oven at 40 °C to obtain more essential oil yield of peppermint shoots. ConclusionIn general, the harvesting time has a significant effect on the morphological characteristics and essential oil of the peppermint shoots. Harvesting peppermint in the full flowering stage resulted in the highest amount of essential oil and essential oil yield. The maximum height and number of leaves in the plant were obtained by harvesting at the time of full flowering, but the maximum wet and dry yield of shoots was observed at the harvest of 50% of flowering. The amount of menthol and menthone as the most important compounds of mint essential oil in the full flowering stage was higher than the other two harvesting times. Also, based on the results of this experiment, different methods of drying peppermint plant have various effects on the essential oil amount of peppermint shoots. The shortest time until drying was related to the use of microwave, oven, sun and shade, respectively, and the highest yield of essential oil was obtained in shade, oven at 40 °C, microwave at 90 watt and sun, respectively.

Agastache rugosa (Fisch. et Mey.) O. Ktze, also known as "Suhuoxiang" (SHX), has been cultivated for more than three hundred years as a valuable aromatic edible and medicinal plant in Jiangsu Province, China. The volatile compounds of SHX from various habitats were investigated by HS-SPME-GC-MS, detecting sixty-five chemical constituents with menthone, pulegone, and estragole being the major volatile compounds. Their relative contents showed various accumulation tendencies in different growth months by GC-MS, with the relative content of menthone gradually increasing, pulegone content decreasing, as well as estragole content climbing initially before declining. This tendency was supported by quantitative experiments using samples from various habitats, which also revealed that the full-bloom stages exhibited the highest total concentrations of menthone and pulegone. The volatile composition of SHX in various plant organs differed, with palmitic acid being the main volatile component of stems, while menthone and pulegone being the core volatile components of leaves and spikes, implying that leaves and spikes should be separated from the stem to obtain higher drug contents. The current findings provide new information for SHX cultivation and applications. [ABSTRACT FROM AUTHOR]

• Melatonin and iron play crucial roles in the growth and production of secondary metabolites in peppermint. • Increasing the concentration of melatonin and Fe-CTs NPs led to a significant increase in biomass accumulation, total carbohydrates, and leaf area in exposed plants. • The highest levels of CAT and APX activities were observed in plants treated with 100 mg L −1 melatonin and 15 mg L −1 Fe-CTs NPs. • The highest value of menthol was obtained in plants treated with 7.5 mg L −1 Fe-CTs NPs. • The highest L-Menthone content was observed in plants treated with 200 mg L −1 melatonin and 15 mg L −1 Fe-CTs NPs. Melatonin and iron play important roles in the growth processes and production of secondary metabolites in medicinal plants. To evaluate the effects of melatonin and Chitosan-Coated Iron Oxide Nanoparticles (Fe-CTs NPs) on peppermint growth, essential oil content and constituents, total carbohydrates and antioxidant enzyme activities, a factorial experiment was conducted based on randomized complete block design (CRBD) with three replications (n = 3). Treatments consisted of different concentrations of melatonin (0, 100, and 200 mg L −1) and Fe-CTs NPs (0, 7.5, and 15 mg L −1). During the experiment, foliar applications of melatonin and Fe-CTs NPs were performed three times with 20 days' interval. Treatments with melatonin, and Fe-CTs NPs had significant effects on the studied traits. The results showed that with increasing melatonin and Fe-CTs NPs concentrations, fresh and dry weights, total carbohydrates, and leaf area index were significantly (P < 0.05) increased in treated plants. The highest CAT and APX activities were observed in plants treated with melatonin at 100 mg L −1 and Fe-CTs NPs at 15 mg L −1. Eucalyptol, Menthyl acetate, Thiophene, 2-ethyl-5-(2-methylpropyl), Mint furanone, and Viridiflorol were found as the major essential oil constituents in peppermint plants under experimental treatments. Moreover, analytical results showed that the highest amount of Menthol (38.48 %) was obtained in plants exposed to Fe-CTs NPs at 7.5 mg L −1, however, the highest L-Menthone (30.53 %) was observed in plants treated with melatonin at 200 mg L −1 and Fe-CTs NPs at 15 mg L −1. The findings provide insights into the regulatory mechanisms of melatonin and Fe-CTs NPs on peppermint growth, physiology and biosynthesis of volatile compounds. [ABSTRACT FROM AUTHOR]

(+)-Neomenthylamine is an important industrial precursor used to synthesize high value-added chemicals. Here, we report a novel biocatalytic route to synthesize (+)-neomenthylamine by amination of readily available (−)-menthone substrate using ω-transaminase. By screening a panel of ω-transaminases, an ω-transaminase from Vibrio fluvialis JS17 was identified with considerable amination activity to (−)-menthone, and then characterization of enzymatic properties was conducted for the enzyme. Under optimized conditions, 10 mM (−)-menthone was transformed in a mild aqueous phase with 4.7 mM product yielded in 24 h. The biocatalytic route using inexpensive starting materials (ketone substrate and amino donor) and mild reaction conditions represents an easy and green approach for (+)-neomenthylamine synthesis. This method underscores the potential of biocatalysts in the synthesis of unnatural terpenoid amine derivatives. [ABSTRACT FROM AUTHOR]

Insecticides of synthetic origin used indiscriminately to manage insect pest populations are known for genotoxicity, neurotoxicity and teratogenicity in non-target organisms as well as the development of resistance in target insects. These issues have focused insect pest management research towards the use of plantbased chemicals of a volatile nature. In this study, two plant-origin volatile compounds, carvacrol and menthone have been evaluated for their potential insecticidal properties against the maize weevil Sitophilus zeamais (Coleoptera: Curculionidae). These two natural volatile chemicals repelled adults and caused lethality in adults as well as larvae. These two volatile chemicals inhibited acetylcholine esterase enzyme activity in adults when fumigated with sub-lethal concentrations. Both volatile chemicals reduced oviposition potential, progeny production and feeding behavior as well as prolonged the developmental period of the insect. Therefore, it can be concluded that these two natural volatile chemicals can be used in the preparation of volatile chemical-based formulations in the management of maize weevil S. zeamais. [ABSTRACT FROM AUTHOR]

Insecticides of synthetic origin used indiscriminately to manage insect pest populations are known for genotoxicity, neurotoxicity and teratogenicity in non-target organisms as well as the development of resistance in target insects. These issues have focused insect pest management research towards the use of plant-based chemicals of a volatile nature. In this study, two plant-origin volatile compounds, carvacrol and menthone have been evaluated for their potential insecticidal properties against the maize weevil Sitophilus zeamais (Coleoptera: Curculionidae). These two natural volatile chemicals repelled adults and caused lethality in adults as well as larvae. These two volatile chemicals inhibited acetylcholine esterase enzyme activity in adults when fumigated with sub-lethal concentrations. Both volatile chemicals reduced oviposition potential, progeny production and feeding behavior as well as prolonged the developmental period of the insect. Therefore, it can be concluded that these two natural volatile chemicals can be used in the preparation of volatile chemical-based formulations in the management of maize weevil S. zeamais. DOI: http://dx.doi.org/10.5281/zenodo.10145014

Wenming Zhao,1,2,&ast; Chengwei Yang,1,&ast; Ning Zhang,3,&ast; Yuanyuan Peng,3 Ying Ma,3 Keru Gu,3 Xia Liu,3 Xiaohui Liu,3 Xijian Liu,3 Yumin Liu,4 Songkai Li,1 Linjing Zhao3 1Department of Spinal Surgery, The 940th Hospital of Joint Logistics Support Force of PLA, Lanzhou, People’s Republic of China; 2Department of Orthopedics, Zhangye Second People’s Hospital, Zhangye, People’s Republic of China; 3College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People’s Republic of China; 4Instrumental Analysis Centre, Shanghai Jiao Tong University, Shanghai, People’s Republic of China&ast;These authors contributed equally to this workCorrespondence: Linjing Zhao, College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People’s Republic of China, Email ljzhao@sues.edu.cn Songkai Li, Department of Spinal Surgery, The 940th Hospital of Joint Logistics Support Force of PLA, Lanzhou, People’s Republic of China, Email lisongkai@gmail.comObjective: The characteristic constituents of essential oils from aromatic plants have been widely applied as antimicrobial agents in the last decades. However, their mechanisms of action remain obscure, especially from the metabolic perspective. The aim of the study was to explore the antimicrobial effect and mechanism of menthone, a main component of peppermint oil, against methicillin resistant Staphylococcus aureus (MRSA).Methods: An integrated approach including the microbiology and the high-coverage lipidomics was applied. The changes of membrane properties were studies by the fluorescence and electron microscopical observations. The lipid profile was analyzed by ultra-high performance liquid chromatography coupled with quadruple Exactive mass spectrometry (UHPLC-QE-MS). The lipid-related key targets which were associated with the inhibitory effect of menthone against MRSA, were studied by network analysis and molecular docking.Results: Menthone exhibited antibacterial activities against MRSA, with minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) of 3,540 and 7,080 μg/mL, respectively. The membrane potential and membrane integrity upon menthone treatment were observed to change strikingly. Further, lipids fingerprinting identified 136 significantly differential lipid species in MRSA cells exposed to menthone at subinhibitory level of 0.1× MIC. These metabolites span 30 important lipid classes belonging to glycerophospholipids, glycolipids, and sphingolipids. Lastly, the correlations of these altered lipids, as well as the potential metabolic pathways and targets associated with menthone treatment were deciphered preliminarily.Conclusion: Menthone had potent antibacterial effect on MRSA, and the mechanism of action involved the alteration of membrane structural components and corresponding properties. The interactions of identified key lipid species and their biological functions need to be further determined and verified, for the development of novel antimicrobial strategies against MRSA.Keywords: menthone, MRSA, antimicrobial activity, cell membrane, lipid homeostasis, microbial lipidomics, UHPLC-QE-MS

In this study, the effect of various drying methods (fresh plant, shade-drying, sun-drying, and oven-drying at 30 and 60 °C) on the essential oil (EO) composition of rose-scented geranium were determined. Essential oil samples were extracted by hydrodistillation and analyzed by GC and GC-MS systems. The highest EO contents were obtained in the fresh plant (1.98%), followed by shade-drying (1.34 %) and oven-drying at 30 °C (1.20 %). The main components were citronellol (23.99-39.87%), geraniol (4.15-17.09%), menthone (4.48-8.34%), linalool (1.96-7.42%), β-caryophyllene (2.63-4.32%), geranyl tiglate (0.99-4.52%), citronellyl butyrate (0.53-5.31%) and cis-rose oxide (0.71-3.15%). The drying methods showed a marked impact on the constituents of the EO samples. The results demonstrated that drying the aerial parts of fresh geranium, and shade-drying and oven-drying at 30 °C were the best optimal methods to obtain the highest oil yield, and citronellol, geraniol, and linalool contents in the oil. [ABSTRACT FROM AUTHOR]

Maceration parameters such as alcohol and mistletoe content were studied to obtain high-quality macerates to produce biska, a traditional Istrian herbal spirit. An ethanol–water solution containing 25, 40, 55, and 70 v/v% ethanol and 20, 40, and 80 g/L mistletoe was macerated and pH, total acids, extract content, and color parameters were measured. Volatile compounds were determined by GC/MS. More than 150 different volatile compounds were detected. The composition of the ethanol–water solution and mistletoe content affects the values of total extract, total acids, and color. Samples with lower alcohol content have a higher number of different acids, aldehydes, alcohols, esters, and ketones, while macerates with higher alcohol content are rich in hydrocarbons and terpenes. Ethyl decanoate; ethyl hexynoate; ethyl octanoate; benzaldehyde; hexanal; octanal; and the terpene compounds limonene, cymene, menthone, humulene, eucalyptol, linalol, and borneol contribute significantly to the aroma of the macerates due to a low odor threshold. Ylangene and α- and β-bourbonene are tentatively determined new terpene molecules that are not found in the mistletoe literature, as well as thujone, which was also detected. For the preparation of aromatic macerates, 40–50 v/v% ethanol and about 40 g/L mistletoe should be used. [ABSTRACT FROM AUTHOR]

(−)‐Menthol is one of the most popular aroma compounds worldwide. While in the past mostly extracted from mint plants, today (−)‐menthol synthesis from other raw materials is becoming more relevant. Common starting materials for menthol synthesis are m‐cresol, citral and myrcene, but also substrates like menthone, mono‐ and bicyclic terpenes and terpenoids have been used for this purpose in the past. As for many applications (−)‐menthol of high purity is required, asymmetric syntheses and enantiomeric resolution of obtained raw products are applied for menthol production. This review gives an overview on the most important synthetic menthol production processes of the companies Symrise, Takasago and BASF and relevant literature in the field of menthol synthesis with a focus on the last 20 years. [ABSTRACT FROM AUTHOR]

Background: Peppermint (Mentha x piperita L.) is one of the most important medicinal plants which used in food, pharmaceutical, perfumery, and flavoring industry. Objective: This study was planned to investigate the effects of foliar application of salicylic acid and yeast extract on production of valuable essential oil components in peppermint. Methods: A completely randomized design experiment with nine treatments consisting salicylic acid (40, 80, 160 and 320 mg/l), yeast extract (0.25, 0.75, 1 and 1.5 g/l) and distilled water (control) with three replications was carried out under greenhouse conditions. Results: In total, forty compounds were identified in the essential oils of the plant aerial parts. Menthone, menthol, piperitone, isopulegol and γ-terpinene were the major compounds of the oils studied. Menthone and menthol were 16.69 % and 14.39 % of the essential oils, respectively. Salicylic acid and yeast extract were increased menthone, neomenthol, piperitone, γ-terpinene and isomenthol acetate production 42, 60, 39, 59 and 34 % higher than control plants, respectively. Foliar application with 320 mg/l salicylic acid gave the best result in the enhancement of the major essential oil components of treated plants. The results of correlation between essential oil constituents showed that the neomenthol content had a significant positive correlation with menthone (r = 0.865**), γ-terpinene (r = 0.848**) and negative correlation with isopulegol (r = -0.886**). Conclusion: The quality of essential oil of M. piperita were influenced by the foliar application of salicylic acid and yeast extract at the appropriate concentrations. Elicitation by 320 mg/l salicylic acid was the optimum treatment for menthone, neomenthol, γ-terpinene and piperitone production.

Background: Menthone that is a monoterpene rich in Mentha × piperita L. has been found anti-inflammatory potential for treating various diseases. However, the effect of menthone supplementation in vivo on systemic allergic inflammation in allergic asthma has not been investigated yet.Purpose: To unravel the puzzle, menthone was administered by gavage to ovalbumin (OVA)-sensitized and challenged BALB/c mice for 5 weeks to evaluate the effects on allergic asthma.Study design: There were six groups in the experiment, including dietary control (DC group, 0 mg menthone/kg b.w./day), 8 (ML group), 40 (MM group) as well as 200 mg menthone/kg b.w./day (MH group), positive control (PC group, 3 mg dexamethasone/kg b.w. before OVA challenge) and non-treatment control (NTC group, normal mice without treatment).Methods: Changes in mediators of systemic immune responses including serum antibody titers, Th1/Th2 cytokines by splenocytes and pro-/anti-inflammatory cytokines by peritoneal macrophages of the experiment mice were analyzed using ELISA.Results: As a result, menthone supplementation significantly decreased Th2-polarized OVA-specific IgG1 and IgE titers, as well as total IgE levels. Menthone supplementation dose-dependently and significantly decreased IL-4 and IL-5 (Th2) secretions by splenocytes. Menthone supplementation decreased pro-/anti-inflammatory secretion ratios (TNF-α/IL-10) by peritoneal macrophages.Conclusion: Our results suggest that menthone supplementation may effectively ameliorate systemic allergic inflammation in the allergic asthmatic mice via regulating Th2-skewed immune balance.

Background: This work is development of new molecules of isoniazid derivatives as dealing with potential of antimicrobial activity against clinical pathogens causing infectious disease. Antimicrobial of novel Mannich base derivatives can be achieved via one-pot synthesis in green chemistry approach. This method offers efficient, mild reaction conditions and high yields. In this study, totally 12 compounds (1a–l) was prepared and screened for cytotoxic and antimicrobial activities. Materials and methods: Newly synthesised compounds were conformed via FT- IR, 1H, and 13C NMR (Nuclear Magnetic Resonance), and mass spectra analysis. All compounds were checked antibacterial activity against gram-positive bacteria of Enterococcus faecalis, Staphylococcus aureus and gram-negative bacteria of Pseudomonas aeruginosa, Klebsiella pneumoniae and Escherichia coli. All compounds were checked against antifungal activity against Aspergillus fumigatus, Candida albicans, Cryptococcus neoformans, Aspergillus niger, and Microsporum audouinii. All compounds were screened for cytotoxic activity against the MCF-7 (Michigan Cancer Foundation-7) cancer cell line. Result: The compound 1g was highly (MIC: 0.25 μg/mL) active against gram-negative bacterial of P. aeruginosa, whereas other compounds 1e and 1h were more active (MIC: 2 μg/mL) in K. pneumoniae and also 1g (MIC: 2 μg/mL) was more active in E. faecalis than standard ciprofloxacin. Antifungal screening, the compound 1b was highly active (MIC: 0.25 μg/mL) against C. albicance, 1g (MIC: 2 μg/mL) and 1h (MIC: 4 μg/mL) was significant of active against A. fumigatus, and the compound 1c (MIC: 4 μg/mL) was extremely active in M. audouinii than clotrimazole. Compound 1g (GI50 = 0.01 μM) exhibited high activity against the MCF-7 cell line, while 1b (GI50 = 0.02 μM) was equipotent active compared with standard doxorubicin. Conclusion: A novel set of isoniazid derivatives (1a–l) and 1h were synthesized and screened for antimicrobial and cytotoxic activities. We found some highly active molecules, which are evidencing to be a potential treatment of bacterial and fungal infection candidates.

The semi-arid highlands offer favorable temperature and radiation conditions for cultivating medicinal plants organically. This practice not only supports the sustainability of the ecosystems in these regions but also presents a valuable opportunity for the production of medicinal plants. Peppermint, a highly sought-after medicinal plant, presents a favorable choice for farmers residing in semi-arid regions due to its versatile applications across various industries. To assess the biomass and essential oil (EO) of peppermint, the utilization of diverse fertilizer sources across different cuttings has been examined. The experimental treatments consisted of four fertilizer sources including poultry manure (POM), sheep manure (SHM), cattle manure (CAM), and chemical fertilizers (CHF), and different cuttings, namely first cutting (CUT1), second cutting (CUT2) and third cutting (CUT3). Plants treated with POM and SHM gave the highest biomass in CUT1 and CUT2, respectively. The nutrient content (macro- and micro-) raised with the application of POM and SHM. The highest EO content was recorded in POM treatment and CUT2. Plants amended with POM had the greatest EO yield in three cuttings. The major EO constituents were menthol (35.2%-58.3%), menthone (3.1%–33.6%), menthyl acetate (1.1%-9.4%), iso -menthone (0.41%-8.8%), with the highest percentages of these compounds reached in treatments with organic manures in various cuttings. High-quality EOs (high menthol and low menthoufuran content) were obtained with organic manure treatments in three cuttings. Plants amended with POM, CHF and CHF showed the highest antioxidant capacity of EO in CUT1, CUT2 and CUT3, respectively. Overall, the usage of POM and SHM can be recommended for increasing biomass and improving the quality of peppermint EO during the growth season, while maintaining ecosystem sustainability by replacing chemical fertilizers in the semi-arid highlands. [Display omitted] • This is the first report to study peppermint essential oil in three cuttings • The semi-arid highlands offer favorable conditions for essential oil production • The amendment with poultry and sheep manure allowed the highest plant biomass • The use of poultry and sheep manure raised peppermint's essential oil yield • Percentages of the main volatile compounds increased by applying organic manures [ABSTRACT FROM AUTHOR]

Essential oils have a vast number of applications in different areas of our daily life. Detailed chiral analysis and structural characterization of their constituents remains an important subject in analytical chemistry. Here, we report on a broadband rotational spectroscopy study of peppermint oil in the frequency range 2–8 GHz. We focus on an unambiguous determination of the excess enantiomers of the oil constituents menthone and isomenthone in the oil by applying chirality-sensitive rotational spectroscopy, the so-called microwave three-wave mixing (M3WM) technique. Additionally, a new menthol conformer, not previously characterized, was experimentally observed, and the gas-phase structures of the two conformers of menthol and menthone were determined experimentally based on the assignment of their 13 C -isotopologues in natural abundance. [ABSTRACT FROM AUTHOR]

Menthone is rich in Mentha × Piperita L. essential oil and it has anti-inflammatory properties; research shows that it is useful, via percutaneous absorption, in treating inflammation-related diseases. However, anti-allergic inflammatory effects of volatile menthone have not yet been used to treat allergic asthma, in vivo. We hypothesized that menthone inhalation may have anti-inflammatory and anti-allergic effects in patients with allergic asthma. Therefore, in our study, menthone inhalation was used to treat ovalbumin (OVA)-sensitized and challenged asthmatic mice. Allergic inflammation mediator changes in the lungs and airways, sera, splenocytes, and peritoneal macrophages of the mice were measured. Relative expression amounts of six receptor genes related to allergic inflammation of the lungs and airways were quantitated using a two-step real time quantitative polymerase chain reaction (qPCR). Results showed that menthone inhalation increased serum OVA-specific IgG2a/IgG1 and IgG2a/IgE ratios, increased Th1-type cytokine production in the bronchoalveolar lavage fluid, and decreased nitric oxide, protein, and eotaxin levels. Menthone inhalation inhibited mast cell and eosinophil degranulation, and chemokine (C-C motif) receptor 3 (Ccr3) gene expression amounts, but (relatively) increased Th1 cytokine secretion by splenocytes. Our results evidence that menthone inhalation alleviates local and systemic allergic inflammation in asthmatic mice. [ABSTRACT FROM AUTHOR]

In order to improve the ability of starch to absorb menthone, corn starch was modified by enzymatic treatment (amyloglucosidase and α-amylase) combined with octenyl succinic anhydride (OSA) esterification. The oil absorption rate of starch modified by enzymatic treatment followed by OSA (P-OSA) reached 101.33%, whereas that of samples with reverse action sequences (OSA-P) was only 59.67%. The degree of substitution of OSA-P was also generally lower than that of P-OSA. At high OSA addition, OSA-P had a smaller specific surface area with fewer pores because octenyl succinic (OS) groups impeded the enzymatic treatment. Compared with OSA-P, the lamellar structure of P-OSA is sparser and less ordered. Owing to its pores, P-OSA was beneficial for the reaction to occur inside the granules, which was observed by Raman spectroscopy and laser confocal microscopy. At high OSA addition, the loading of P-OSA to menthone could reach 64.34 mg/g. [ABSTRACT FROM AUTHOR]

Three methods of shade (MI), open sun (MII) and new designed of solar (MIII) drying were used for peppermint dehydration. The air velocity (u) and temperature (Td) of MI, MII and MIII were 0.5, 0.5, and 1.5 m/s and 32, 36, and 48 °C, respectively. The energy utilization efficiency, Td/u ratio and drying rate of MIII reached 85%, 48 °C.s.m−1 and 12.5 gH2O/min, respectively, which were higher than those in MI and MII. The inhibition power of dried peppermints against 6-log colony forming unit/ml of Staphylococcus aureus (Sa) were also evaluated. While the chlorophyll and essential oil extraction efficiency of MIII-product were 30% and 60% respectively higher than those in MII-product, its total phenolic contents and antioxidants activities were 25% and 26% more than those in MI-product. The essential oil of MIII-product had significantly (p < 0.05) higher inhibiting compounds (mainly Menthone) against pathogenic gram-positive Sa compared with those in MI and MII-products. [ABSTRACT FROM AUTHOR]

Peppermint, Mentha piperita L. belonging to the Lamiaceae family, contains a valuable essential oil known for its high menthol and menthone content. During the vegetation seasons of 2016 and 2017, field studies were conducted in Turkey's Isparta climate by using randomized blocks to examine the yield and oil composition of the new peppermint cultivars. In these studies, Multimentha produced the highest herb yield even though the quality of its essential oil is relatively poor due to its low menthol content. Yield levels of other cultivars were similar to each other with the same statistical group. In the study, Citaro, Tokat CL-8, and Chocolate varieties had high menthol contents and were within the same chemical group. Varieties reacted differently to years and harvesting seasons, including summer and autumn. The menthol content of Citaro and Tokat CL-8 cultivars was higher in the fall harvest compared to the summer harvest. On the other hand, the menthol content of the Chocolate cultivar remained stable throughout the seasons. The study has revealed that the yields of the varieties with high menthol are low, and the oils obtained from all these varieties except Multimentha conform to the European pharmacopoeia. [ABSTRACT FROM AUTHOR]

Peppermint (Mentha piperita L.) is one of the most cultivated and consumed herbs. The pharmaceutical properties and nutrition values of peppermint oil make it an important commercial product. This study aimed to explore the volatile compounds in the essential oil extracted from different peppermint genotypes commercially grown in China. Oil extraction using a steam distillation followed by gas chromatography-mass spectrometry resulted in the quantification of 53 volatile compounds from five major classes, including esters, alcohols, ketones, terpenes, and volatile compounds. The highest essential oil yields were observed in Golden mint, Silver mint, Scottish mint, and Banana mint. Moreover, three genotypes, viz., Milk fruit mint, Winter Mint, and Pineapple, were screened with the highest diversity of volatile compounds. Major volatiles identified were linalyl acetate, 1-octene-3-acetate, geranyl acetate, neryl acetate, menthol, linalool, menthone, and carvone. The phenotypic characterization coupled with the volatile profiling in this study provides the basis for selecting and improving the investigated peppermint genotypes for specific commercial uses. [ABSTRACT FROM AUTHOR]

A series of novel menthone derivatives bearing pyrimidine and urea moieties was designed and synthesized to explore more potent natural product-derived antitumor agents. The structures of the target compounds were confirmed by FTIR, NMR, and HRMS. The in vitro antitumor activity was tested by standard methyl thiazolytetrazolium assay and showed that 4i, 4g, 4s, and 4m are the best compounds with IC50 values of 6.04 ± 0.62µM, 3.21 ± 0.67µM, 19.09 ± 0.49µM, and 18.68 ± 1.53µM, against Hela, MGC-803, MCF-7, and A549, respectively. The results of the preliminary action mechanism studies showed that compound 4i, the representative compound, could induce cell apoptosis in Hela cells in a dose-dependent manner and might arrest the cell cycle in the G2/M phase. Furthermore, the results of network pharmacology prediction and Western blot experiments indicated that compound 4i might inhibit Hela cells through inhibit PI3K/Akt/mTOR signaling pathway. The binding modes and the binding sites interactions between compound 4i and the target proteins were predicted preliminarily by the molecular docking method.

Peppermint (Mentha x piperita L.) is not only used as a medicinal plant with therapeutic activity but also as a tea infusion, herb, spice or as a flavoring agent in other preparations. However, its adverse side effects on health have been described. The outcome of this review revealed that peppermint and its main constituents (pulegone, menthone, menthol and menthofuran) are moderately toxic. Peppermint and its menthol isomers possess no major innate mutagenic, genotoxic or embryotoxic properties. Peppermint essential oil interacts with cytochrome P450 isoenzymes in human liver microsomes. It is contraindicated in patients with bile duct obstruction and gall bladder inflammation. In patients with gastrointestinal reflux or hiatus hernia, its use should be exercised with caution because it may exacerbate the symptoms of gastrointestinal reflux. [ABSTRACT FROM AUTHOR]

Liquid active ingredients are typically less stable than their solid analogues and they are also generally associated with storage and handling problems when considered for industrial usage. However, many synthetic and natural active ingredients are liquid or low melting solids under ambient conditions, and formulation or cocrystallization might be helpful to modulate this characteristic. As an alternative, crystalline porous matrices, such as metal–organic frameworks, can be used to encapsulate the guest molecules providing them with a crystalline environment very different to what might be observed in the pure liquid phase, thus stabilizing the active compounds in the solid state. In this work, PUM168, a flexible heteroleptic MOF, has been used to encapsulate three liquid compounds (propofol, carvacrol and menthone). The nanoconfinement of the three guests has been fully investigated via SCXRD in terms of host–guest interactions and framework rearrangement as a function of the guest loading. [ABSTRACT FROM AUTHOR]

In this research, the effects of 2 different planting times (autumn and spring) on the yield and quality of peppermint (Mentha × piperita L. var. Mitcham) were investigated under marginal land conditions. The test was conducted in Çukurova region located in the Eastern Mediterranean by using a randomized complete block design with three replications. Based on the results, the highest plant height (43 cm), fresh herb yield (12763 kg ha-1), dry herb yield (3407 kg ha-1), dry leaf yield (1976 kg ha-1) and essential oil yield (56.3 Lt ha-1) was determined in spring planting. The maximum ratio of essential oil was found in the first cuttings (3.18%). The yield values were higher in the first cuttings on year basis. With increasing the number of cuttings, a gradual decrease was observed in yield components. As a result of the gas chromatography analysis, oxygenated monoterpenes constituted the major chemical component group of M. × piperita essential oil (74.21-80.86%). The highest oxygenated monoterpenes were specified in the 1st cuttings of both planting seasons. Menthol (23.2-37.46 %) and menthone (22.82-31.56 %) were identified as the major components. Menthol percentage was higher in spring planting, and this rate has decreased every year compared to the previous one. As the number of cuttings increased, menthone rate also enhanced. On the other hand, as the rates of menthone increased, there was a decrease in menthol rates. a-Pinene (2.33-5.61%), limonene (0.63-4.13%), 1,8-cineole (5.22-9.98%), menthofuran (1.47-4.72%), isomenthone (1.14-5.95%), menthyl acetate (2.14-5.2%) and neomenthol (1.09-2.5%) were determined as other important components. Although the agronomic yield obtained from marginal land conditions was relatively lower, it was found superior in terms of quality and has adapted to standards values. As a result, the cultivation of the M. × piperita is economically viable in marginal lands without irrigation problems. [ABSTRACT FROM AUTHOR]

This study evaluated the influence of seasonality in essential oil (EO) chemical composition of Mentha x piperita L. and Mentha viridis L. grown in southeast of Brazil. Leaves were collected from November 2011 until August 2013, in the middle of the following seasons: Spring (November), Summer (February), Autumn (May) and Winter (August). EO extraction was carried out by hydrodistillation in Clevenger apparatus for 1 hour. Chemical composition of EO was analyzed by GC-FID and GC-MS. The EO content and its chemical composition were influenced by seasonality in both species. The highest EO content was obtained for M. x piperita during spring (4.26%) and for M. viridis during spring (3.30%) and summer (3.70%). Mentha x piperita increased menthol (16.31 to 41.26%), neomenthol (3.02 to 6.39%) and menthone (5.56 to 41.58%) contents during spring and summer, respectively. Whereas, M. viridis EO content did not show a quality response pattern in relation to seasonality. Therefore, harvest time for M. x piperita is recommended during spring, and for M. viridis is recommended during spring and summer. [ABSTRACT FROM AUTHOR]

• Mentha piperita are exploited as a natural source of bioactive phytochemicals • Several processes are available for extraction of plant phytopchemicals • Different elicitors can be used to increase secondary metabolites production • Peppermint components have new applications against diseases of different origins • M. piperita compounds have clinical, industrial , and agricultural applications Mentha piperita L. (peppermint) is one of the most popular and widely consumed species worldwide, and is used in the medical as well as in industrial and culinary fields. The importance of M. piperita is mainly due to its essential oils (EOs) and polyphenols. The present work reviews various novelty aspects of M. piperita phytochemicals, including their components, processes used to obtain EOs and extracts , agricultural strategies for the induction of EO production, shelf-life processes, and their application in phytoremediation, animal science, herbicides, pesticides, food industries, and therapeutic issues. The amount and components of M. piperita EOs (MpEOs) available vary widely depending upon the region, climatic and agronomic conditions, the extraction technique and drying procedure. In recent years, different methodologies have been evaluated to enhance EO production and other phytochemicals, such as inoculation with plant growth-promoting rhizobacteria, application of chemical elicitors, titanium dioxide nanoparticles, fly ash, and environmental factors. MpEOs and phenolic compounds possess high antimicrobial, antioxidant, antispasmodic, anthelmintic, and acetylcholinesterase inhibitory activities. Due to the wide range of bioactivity and antioxidant activity, this is an interesting topic of research due to the growing usage of natural antioxidants as additives in food and cosmetics. However, further studies should be directed towards MpEOs and extract production and formulation, to enable their wide scale application. [ABSTRACT FROM AUTHOR]

BACKGROUND Insects rely on their sense of smell to locate food and hosts, find mates and select sites for laying eggs. Use of volatile compounds, such as essential oils (EOs), to repel insect pests and disrupt their olfaction‐driven behaviors has great practical significance in integrated pest management. However, our knowledge on the olfaction‐based mechanisms of EO repellency is quite limited. RESULTS: We evaluated the repellency of peppermint oil and nine plant EO components in Drosophila melanogaster, a model insect for olfaction study, and D. suzukii, a major fruit crop pest. All nine volatiles, menthone, (−)‐menthol, menthyl acetate, (R)‐(+)‐limonene, nerol, (+)‐fenchone, (−)‐α‐thujone, camphor, norcamphor and peppermint oil, elicited repellency in D. melanogaster in a dose‐dependent manner. Most of the compounds, except camphor, also elicited repellency in D. suzukii. Menthone, (R)‐(+)‐limonene and (+)‐fenchone were the most potent repellents against D. suzukii. Repellency was reduced or abolished in two D. melanogaster mutants of the odorant receptor co‐receptor (Orco), indicating that the observed repellency is odorant receptor (Or)‐mediated. Repellency by peppermint oil, menthone, (R)‐(+)‐limonene, (−)‐α‐thujone and norcamphor also involves Or‐independent mechanism(s). Single sensillum recording from both species revealed that common and distinct Ors and olfactory receptor neurons were activated by these compounds. CONCLUSIONS: The tested plant EO components evoke repellency by activating multiple Ors in both Drosophila species. Our study provides a foundation for further elucidation of the mechanism of EOs repellency and species‐specific olfactory adaptations. © 2021 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

BACKGROUND: The rice weevil, Sitophilus oryzae (L., 1763) (Coleoptera: Curculionidae), is a stored grain/seed pest of several crops. Botanicals represent an option to manage this pest, especially those with high toxicity determined by its structure and physicochemical properties and low residue left behind on treated grains/seeds. Enantiomers are bioactive molecules in organic processes. The aim of this study was to evaluate the insecticidal activity of two enantiomeric forms of the monoterpenes citronellal, limonene, linalool, menthone and α‐pinene against S. oryzae adults through contact, fumigant and repellent assays. RESULTS: All results were compared with absolute acetone as the negative control and those from contact assays also with malathion as the positive control. (S)‐(−)‐linalool was the most toxic by contact to S. oryzae and (S)‐(−)‐menthone through fumigation, while the two enantiomeric forms of menthone and α‐pinene were the best repellents. CONCLUSIONS: The high toxicity of only one of the two monoterpene enantiomers showed the importance of form and percentage of enantiomer in the commercial product, which affect the success of the product to controlling S. oryzae. © 2021 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Background: Nitrogen is the most important nutrient requirement for plants. Nitrogen supplying affected the leaf area, carbon fixation, glandular trichomes formation, ATP and NADPH content which resulted to the terpenoids biosynthesis enhancement and essential oils accumulation. Objective: This study was aimed to evaluate changes of essential oil content and components by use different levels of Urea fertilizer and its relation with the antioxidant status of peppermint. Method: The two field experiments were conducted on randomized complete block design at 2013 and 2014. The treatments consisted of three levels of nitrogen fertilizer (urea) (0, 75, and 150 kg ha-1). The evaluated traits were included antioxidant enzymes, essential oil percentage and essential oil components. Results: The urea fertilizer had a significant effect (P≤0.01) on the soluble protein amount and antioxidant enzymes activity. Urea consumption in the both years increased the peppermint essential oil content. The interaction of nitrogen fertilizer and year had a significant effect on most of the essential oil components excepted to β-pinene, myrcene, Limonene, 1,8- Cineole, Z-β- Ocimene, and α- Terpineol. Conclusion: Using nitrogen fertilizer increased the peppermint essential oil content. Also, nitrogen deficiency reduced the soluble proteins and essential oil content and in contrast, it increased antioxidant enzymes activity and pulegone content. Therefore, consumption of 75 kg urea per hectare is recommended due to increasing essential oil content, decreasing pulegone rate, and no significant effect on menthol, menthone, and menthofuran contents.

The aims of the present study were to evaluate the effects of different ventilation systems and sucrose concentrations on the growth, photosynthetic pigment content, and chemical composition of Mentha arvensis L. and M. viridis L. Photon flux (PPF) and growth were also evaluated based on M. arvensis heterotrophic, photomixotrophic, and photoautotrophic culture systems. Nodal segment explants were cultured on medium with 0, 15, and 30 g L−1 sucrose and four alternative membrane systems (AMS) in culture medium, namely no membrane (NMS), one (AMS1), two (AMS2), and four (AMS4) membranes. Mentha arvensis cultivation on medium containing 15 g L−1 of sucrose and four membrane (AMS4) led to the highest dry weight accumulation. Mentha viridis reached the same result with medium containing 30 g L−1 sucrose and AMS2 and AMS4. Mentha arvensis produced higher chlorophyll a, b and total chlorophyll, as well as carotenoids when cultured on medium with 30 g L−1 of sucrose and AMS4 and M. viridis when cultured on medium with 15 g L−1 of sucrose and AMS4. The NMS without sucrose favored higher pulegone and AMS4 induced higher menthol, menthone, and limonene from M. arvensis cultured in vitro. Furthermore, AMS2 induced menthol production and AMS1 increased trans-sabinene, linalol, and limonene content in M. viridis. Mentha arvensis plantlets cultivated under photoautotrophic system with 130 μmol m−2 s−1 showed improved growth and the highest leaf area. Thus, the recommendation to increase upper biomass and plantlet quality in mint species lies on employing an alternative membrane system under higher PPF. [ABSTRACT FROM AUTHOR]

This study was carried out to investigate the flavoral essential oil components in the stems of Agastache rugosa. These components were analyzed using gas chromatography-mass selective detector (GC-MSD). The stems of Agastache rugosa were contained alcohols, aldehydes, ketones, fatty acid esters, and terpenoids. The peak area (%) of estragole was highest among its oil components and the next were pulegone and menthone. The terpenoid alcohols found were 1-octen-3-ol, chavicol, spatulenol, 3-hexen-1-ol, 2-cyclohexen-1-ol, methyl eugenol, and octaethyllene glycol. The stems also contained ketones such as pulegone, menthone, cis-isopulegone, 2-cyclohexene-1-one, 3-octanone, 1-cyclohexanone, isoindole-1- one, t-ionone, inden-2-one, as well as the aldehydes of 4-methoxycinnam and benzaldehyde. The following esters were also detected 1-isopulegone-3-yl acetate, caryophyllene oxide, acetate and benzendicarboxylic acid ester. The terpenoids in the stems were identified as caryophyllene, limonene, cyclohexasiloxane-D, germacrene-D, anethole, cadinene, muurolene, and bourbonene. Overall Agastache rugosa contained several functional oil components including phenylpropanoids and terpenoids as flavoral essential oil components for natural aromatherapy. [ABSTRACT FROM AUTHOR]

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Mentha arvensis, commonly named menthol mint or Japanese mint, is an important volatile oil- bearing plant having high amounts of natural menthol. M. arvensis volatile oil (VO) and menthol have a considerable share in the global trade of medicinal plants for widespread use in the pharmaceutical, food, cosmetic, and fragrance industries. This study was conducted to investigate the response of M. arvensis var. piperascens Holmes to planting time (fall and spring) under marginal land conditions. Plants were propagated by three-year-old rhizomes. Obtained results showed that the effect of growing seasons was not significant on the agronomic traits and VO yield. However, the effects of six different impressions during the experiment were significant on the studied parameters. The highest plant height (45 cm), fresh biomass (16692 kg ha-1), dry biomass (4736 kg ha-1), leaf dry yield (2816 kg ha-1), and VO yield (158 L ha-1) were observed in the 1st cuttings. The yield components decreased with the plants aging. The lowest values of the mentioned parameters were in the sixth harvest. Moreover, the VO content varied from 4.6-6.1 %. Menthol (52.19-73.53 %) and menthone (3.42-18.89 %) were identified as the most major VO components of M. arvensis. While the menthol percent decreased in the last cuttings, menthone increased correspondingly. Based on the results of this study, it can be suggested that the cultivation of mint in marginal land has a desirable agronomic yield and acceptable chemical properties. [ABSTRACT FROM AUTHOR]

This work is development of new molecules of isoniazid derivatives as dealing with potential of antimicrobial activity against clinical pathogens causing infectious disease. Antimicrobial of novel Mannich base derivatives can be achieved via one-pot synthesis in green chemistry approach. This method offers efficient, mild reaction conditions and high yields. In this study, totally 12 compounds (1a–l) was prepared and screened for cytotoxic and antimicrobial activities. Newly synthesised compounds were conformed via FT- IR, 1H, and 13C NMR (Nuclear Magnetic Resonance), and mass spectra analysis. All compounds were checked antibacterial activity against gram-positive bacteria of Enterococcus faecalis , Staphylococcus aureus and gram-negative bacteria of Pseudomonas aeruginosa , Klebsiella pneumoniae and Escherichia coli. All compounds were checked against antifungal activity against Aspergillus fumigatus , Candida albicans , Cryptococcus neoformans, Aspergillus niger , and Microsporum audouinii. All compounds were screened for cytotoxic activity against the MCF-7 (Michigan Cancer Foundation-7) cancer cell line. The compound 1g was highly (MIC: 0.25 μg/mL) active against gram-negative bacterial of P. aeruginosa , whereas other compounds 1e and 1h were more active (MIC: 2 μg/mL) in K. pneumoniae and also 1g (MIC: 2 μg/mL) was more active in E. faecalis than standard ciprofloxacin. Antifungal screening, the compound 1b was highly active (MIC: 0.25 μg/mL) against C. albicance, 1g (MIC: 2 μg/mL) and 1h (MIC: 4 μg/mL) was significant of active against A. fumigatus, and the compound 1c (MIC: 4 μg/mL) was extremely active in M. audouinii than clotrimazole. Compound 1g (GI 50 = 0.01 μM) exhibited high activity against the MCF-7 cell line, while 1b (GI 50 = 0.02 μM) was equipotent active compared with standard doxorubicin. A novel set of isoniazid derivatives (1a–l) and 1h were synthesized and screened for antimicrobial and cytotoxic activities. We found some highly active molecules, which are evidencing to be a potential treatment of bacterial and fungal infection candidates. [ABSTRACT FROM AUTHOR]

The genus Mentha has been known as culinary source of minty note. Besides, the essential oil imparts value to consumer products like confectionery, cosmetics, and pharmaceutical preparations. A simple and sensitive enantioselective gas chromatographic method is described for the quantitative analysis of terpenoid enantiomers in essential oils using different cyclodextrin coated stationary phases. Limonene, menthone, menthol, and menthyl acetate were identified as pure (-)-enantiomers whereas isomenthone, neomenthol, pulegone, and piperitone as pure (+)-enantiomers in menthol mint, and peppermint oils, respectively. The selectivity of each enantiomer was also demonstrated. A β-cyclodextrin phase with diethyl substitution provides baseline resolution for all target enantiomers with selectivity ranged from 1.004 to 1.050. Moreover, permethylated or diacetylated-β-cyclodextrin showed no selectivity for (+/-)-menthol enantiomers. The current study may facilitate the origin authentication studies of mint oils. Investigation of enantiomers involved in menthol biosynthesis revealed that only (-)-menthol is present in the essential oils of Mentha species. [ABSTRACT FROM AUTHOR]

Plants can use volatiles for remote suppression of competitors. Mints produce essential oils, which are known to affect the growth of other plants. We used a comparative approach to identify allelopathic compounds from different Mints (genus Mentha, but also including Cat Mint, Nepeta cataria, and Corean Mint, Agastache rugosa, belonging to sisters clades within the Mentheae) using the standard cress germination assay as readout. To understand the mechanism behind this allelopathic effect, we investigated the response of tobacco BY-2 cell lines, expressing GFP-tagged markers for microtubules and actin filaments to these essential oils. Based on the comparison between bioactivity and chemical components, we identified menthone as prime candidate for the allelopathic effect, and confirmed this bioactivity targeted to microtubules experimentally in both, plant cells (tobaccoBY-2), and seedlings (Arabidopsis thaliana). We could show that menthone disrupted microtubules and induced mortality linked with a rapid permeabilization (less than 15 min) of the plasma membrane. This mortality was elevated in a tubulin marker line, where microtubules are mildly stabilized. Our study paves the way for the development of novel bioherbicides that would be environmentally friendly.

Background: Acyclovir (ACV) is known to be toxic to gonads, inducing apoptosis in the reproductive system. The beneficial effects of vitamin C (Vit C) and menthone, both as antioxidant agents on various organs has been reported. Objective: This study evaluated the potential role of the Vit C and menthone on the DNA damage in rat spermatozoa induced by the ACV. Materials and Methods: In this experimental study, adult male albino Wistar rats with average weight of 250±10 gr, were divided into six groups (n=18/each), as: ACV (15 mg/kg/day), ACV+Vit C (20 mg/kg/day), ACV+ menthone (100 µl/d), ACV+ menthone (250 µl/d), ACV+ menthone (400 µl/day) and control group without any treatment. At the end of experiment, the animals were sacrificed and sperm samples were collected and isolated in phosphate-buffered saline and examined by TUNEL staining process. The percentage of TUNEL positive spermatozoa was evaluated by fluorescence microscopy. Each experiment was performed in three repeats. Results: Male rats exposed to ACV had significant increase in DNA damages in comparison to other groups. The percentage of TUNEL positive sperm cells was 90.83 (p

Quantitative and qualitative composition of essential oils of peppermint breeds Lebedinaya Pesnya, Lubenchanka, Lidiya, Ukrainskaya Perechnaya, Mama, Chornolista was investigated before and after clonal microreproduction by the method of isolated tissues and bodies culture in vitro. Methods of essential oil steam distillation, capillary gas chromatography and statistical analysis were used in the research. It is established that increase in essential oil quantity was observed for peppermint breeds on which reproduction and improvement іn vіtro technology was applied. As a result of clonal microreproduction of peppermint plants in culture іn vіtro on nutrient medium Murasige and Skug, in which the growth regulators 0.75 mg/l of 6-benzylaminopurine, 0.1 mg/l of adenine, 0.05 mg/l of indolil-3-acetic acid and 0.5 mg/l of gibberellins acid were added and virocide Ribavirin in concentration 10 mg/l, improvement was obtained in comparison with vegetatively reproduced plants; increase in essential oil quantity per hectare was established for the following breeds; Chornolista by 54.2%, Lebedinaya pesnya by 38.2%, Ukrainskaya Perechnaya by 36.7%, Mama by 28.5%, Lubenchanka by 17.1% and Lidiya by 11.6%. For oil content the highest indices were noted for Lubenchanka, Mama and Lebedinaya Pesnya peppermint breeds with product yield 4.02%, 3.98% and 3.84% respectively. It was established that the essential oil component composition in non-clonal peppermint plants raw materials and plants-regenerants after culture in vitro is variable depending on breed. Limonene, cineole, menthone, menthofuran, iso-menthone, menthyl acetate, β-caryophyllene, iso-menthol, menthol, pulegone, germacren, piperitone, carvone were identified in peppermint essential oil. High content of menthol, low content of carvone, piperitone, pulegone (except for Chornolista, Ukrainskaya Perechnaya breeds) and menthofuran (except for Chornolista, Ukrainskaya Perechnaya and Lubenchanka breeds) are characteristic for Ukrainian selection peppermint investigated breeds. A clear tendency to menthol and menthone content ratio increase is observed in plants which were improved in conditions іn vіtro. Pulegone was not detected in essential oil samples of Lebedinaya Pesnya, Lidiya and Mama breeds. Biochemical markers of Lebedinaya Pesnya, Lubenchanka, Mama breeds, which differentiate them within the group of investigated breeds, are higher limonene, piperitone and menthol pool; for Ukrainskaya Perechnaya and Chornolista breeds – pulegone, cineole and menthone; for Lidiya breed – iso-menthone.

This work was aimed at quantitative and qualitative analyses of the essential oil of peppermint leaves under different drying methods. Thin layer drying experiments of the leaves were performed in shade, hot air dryer (at temperatures of 50°C, 60°C, and 70°C), and microwave oven (at power levels of 200, 400, and 800 W). Essential oils of the fresh and dried samples were extracted by hydrodistillation and analyzed using gas chromatography-mass spectrometry (GC/MS). The highest (22.24 g/kg dry matter) and the lowest (1.33 g/kg dry matter) oil yields were obtained from the hot air-dried leaves at temperature of 50°C and microwave-dried leaves at power of 800 W, respectively. In general, increasing drying temperature decreased the essential oil content. The GC/MS analysis of essential oils showed that the chemical compounds belonged mostly to oxygenated monoterpenes class (72.34–86.41%). The chemical compounds group was significantly (p

Peppermint is an important medicinal plant, and it is known for its essential oils and phenolic acids. Verticillium wilt is a vascular disease resulted from several Verticillium spp. causing significant economic losses in peppermint cultivation. In this study, the fungus Gibellulopsis nigrescens (syn. Verticillium nigrescens) was isolated from symptomless peppermint plants during the regular control of Verticillium wilt on peppermint in Germany. A pure fungal culture was prepared, and fungal DNA was extracted. Ribosomal internal transcribed spacer (ITS), beta-tubulin (TUB), and translation elongation factor 1-α (TEF1-α) were amplified, sequenced, and deposited in the GenBank. These sequences are located within the Gibellulopsis nigrescens cluster. Koch's postulate was fulfilled, and the fungus was re-isolated from the inoculated plants. Up to our knowledge, this is the first report of Gibellulopsis nigrescens on peppermint in Germany. [ABSTRACT FROM AUTHOR]