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BackgroundThe antifungal properties of essential oils (EOs) and their active constituents have been well documented. Histone acetylation is pivotal in modulating gene expression and influences biological processes in living organisms.ResultsThis study demonstrated that menthone, the primary component of Mentha haplocalyx EO, exhibited notable antifungal activity against Fusarium proliferatum (EC50 = 6.099 mmol/L). The treatment significantly inhibited hyphal growth, reduced spore germination rates from 31.49 to 4.95%, decreased spore viability from 46.88 to 20.91%, and reduced spore production by a factor of 17.92 compared with the control group while simultaneously enhancing cell membrane permeability. However, the direct relationship between menthone and histone acetylation in inhibiting F. proliferatum remains nebulous. Our RNA sequencing (RNA-seq) analysis identified 7,332 differentially expressed genes (DEGs) between the control and menthone-treated groups, 3,442 upregulated and 3,880 downregulated, primarily enriched in pathways related to ribosome biogenesis and energy metabolism. Chromatin immunoprecipitation sequencing (ChIP-seq) analysis revealed that menthone inhibited the growth of F. proliferatum by decreasing H3K27ac levels and interfering with the transcription of energy metabolism-related genes. By integrating the RNA-seq data with the ChIP-seq results, we identified 110 DEGs associated with reduced H3K27ac modification primarily associated with ribosome biogenesis. Menthone affected the growth of F. proliferatum by reducing the expression of ribosome biogenesis-related genes (FPRO_06392, FPRO_01260, FPRO_10795, and FPRO_01372).ConclusionThis study elucidated the mechanism by which menthone inhibits F. proliferatum growth from a histone acetylation modification perspective, providing insights into its application as an antifungal agent to prevent root rot in Panax notoginseng.

Background: The antifungal properties of essential oils (EOs) and their active constituents have been well documented. Histone acetylation is pivotal in modulating gene expression and influences biological processes in living organisms. Results: This study demonstrated that menthone, the primary component of Mentha haplocalyx EO, exhibited notable antifungal activity against Fusarium proliferatum (EC50 = 6.099 mmol/L). The treatment significantly inhibited hyphal growth, reduced spore germination rates from 31.49 to 4.95%, decreased spore viability from 46.88 to 20.91%, and reduced spore production by a factor of 17.92 compared with the control group while simultaneously enhancing cell membrane permeability. However, the direct relationship between menthone and histone acetylation in inhibiting F. proliferatum remains nebulous. Our RNA sequencing (RNA-seq) analysis identified 7,332 differentially expressed genes (DEGs) between the control and menthone-treated groups, 3,442 upregulated and 3,880 downregulated, primarily enriched in pathways related to ribosome biogenesis and energy metabolism. Chromatin immunoprecipitation sequencing (ChIP-seq) analysis revealed that menthone inhibited the growth of F. proliferatum by decreasing H3K27ac levels and interfering with the transcription of energy metabolism-related genes. By integrating the RNA-seq data with the ChIP-seq results, we identified 110 DEGs associated with reduced H3K27ac modification primarily associated with ribosome biogenesis. Menthone affected the growth of F. proliferatum by reducing the expression of ribosome biogenesis-related genes (FPRO_06392 , FPRO_01260 , FPRO_10795 , and FPRO_01372). Conclusion: This study elucidated the mechanism by which menthone inhibits F. proliferatum growth from a histone acetylation modification perspective, providing insights into its application as an antifungal agent to prevent root rot in Panax notoginseng. [ABSTRACT FROM AUTHOR]

Wenming Zhao,1,2,* Chengwei Yang,1,* Ning Zhang,3,* 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*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

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

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.

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]

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.

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]

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

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.

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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]

The presence and toxicological risks of synthetic coolants in electronic nicotine delivery systems (ENDS) have not been thoroughly studied. We identified the synthetic coolant menthone 1,2-glycerol ketal (MGK) in a menthol-flavored e-liquid at a concentration of ∼170 μg/mL. We also detected MGK in aerosols resulting from heating the e-liquid with an electronic waterpipe. MGK was initially detected in the e-liquid by two-dimensional gas chromatography-time-of-flight mass spectrometry. To avoid potential analytical artifacts that could result from heating samples in the injection port of the gas chromatograph, quantitation of MGK in the e-liquid was accomplished using a liquid chromatography-tandem mass spectrometry method. Following recent reports identifying other synthetic coolants in e-liquids, these results add knowledge about inhalation exposures from ENDS use and suggest the importance of future research to study the potential inhalation toxicity related to the use of MGK-containing e-liquids in ENDS devices. Furthermore, the results demonstrate the ability to quantify ketals in e-liquids using liquid chromatography methods.

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]

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]

Background and objectives: Menthol and menthone are two important components in the essential oil of peppermint(Mentha piperita L.) which are commercially used in the pharmaceutical industries. This study has presented the allometric ratio of menthol and menthone to pulegone affected by the induction of bioregulators. Methods: The experiment was conducted in controlled condition based on completely randomized design (CRD) in three replications. The plants were subjected to different bioregulator treatments including distilled water; 5 %v/v methanol; 40 ppm GA3 (gibberellic acid) + 5%v/v methanol; 40 ppm IBA (indole butyric acid) + 5%v/v methanol, and 40 ppm GA3 + 40 ppm IBA + 5%v/v methanol. Essential oils analysis were performed using different methods of gas chromatography and gas chromatography-mass spectroscopy. Results: The application of 40 ppm IBA + 5%v/v methanol increased the essential oil content. With the use of bioregulators, the content of menthol and menthone increased and the amount of pulegone was conversely reduced. The lowest content of pulegone was measured in the treatment with 40 ppm GA3 + 40 ppm IBA + 5%v/v methanol. Allometric analysis of components showed that the ratios of menthol/pulegone, menthone/pulegone, and (menthone+menthol)/pulegone increased by bioregulators application, especially with 40 ppm GA3 + 40 ppm IBA + 5%v/v methanol. Conclusion: Using plant bioregulators could be a suitable procedure to increase pro-health potential through increasing the amount of menthol with decreasing the content of pulegone in the essential oil. It is possible that the bioregulators were able to convert pulegone to menthol and menthone.

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]

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]

In order to use commercial starch for flavor encapsulation, three starches (mungbean, rice, and tapioca) were selected to determine their ability to form inclusion complex with menthone. Mungbean starch had the highest amylose content, followed by rice starch and tapioca starch, respectively. After complexation, appearance and microstructure changes were observed for all starches. Mungbean and tapioca complexes with well-organized V7 crystalline pattern gave similar menthone entrapment (around 4%) which was higher than that of the rice sample (<1%). Molecular size distribution of the complexes revealed the role of amylose fractions for both mungbean and tapioca complexes. According to differential scanning calorimetric analysis, menthone complexes formation was confirmed by a thermoreversible event. Regarding the high yield of starch precipitate and menthone entrapment, mungbean starch is considered a more suitable material for menthone encapsulation rather than tapioca and rice starches. [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. [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]

Essential oils obtained from the hydrodistillation of fresh aerial (FA) and dried aerial parts (DA) of Satureja baborensis (Batt.) Briq. (Lamiaceae) were analyzed using GC and GC/MS, revealing the presence of 34 components for FA and 29 components for DA. The main constituents of the essential oils were limonene (FA 1.21%, DA4.73%), piperitenone oxide (FA7.84%, DA18.15%), menthone (FA9.29%, DA1.18%), pulegone (FA53.88%, DA25.85%), and cis-piperitone oxide (FA2.96%, DA15.05%). FAand DAessential oils exhibited considerable antibacterial activity against nine Gram-positive and Gram-negative bacteria by the use of the disk diffusion method. In addition, the aqueous methanol extract of Satureja baborensis (MESB) showed high polyphenol (76.33 ± 7.60 mg gallic acid equivalents) and flavonoid contents (42.18 ± 1.03 mg equiv. QUE/g) and a higher antioxidant activity in ferric-reducing power, silver nanoparticle, and phenanthroline assays (A0.5 16.90 ± 1.62, 12.18 ± 1.61 and 5.59 ± 0.79 μg/mL respectively) than in DPPH, CUPRAC, and ABTS assays. Significant butyrylcholinesterase inhibitory activity was displayed by the aqueous MESB (IC50 76.58 ± 7.88 μg/mL). [ABSTRACT FROM AUTHOR]

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<0.001) in ACV group. The protective role of both antioxidants used in high dose, compensate the adverse effects of the ACV. The results showed that the percentage of apoptotic sperm in the ACV+Vit C group was 16.38 (p<0.001) and in the ACV+ menthone (400 µl/d) group was 16.05 (p<0.001). Conclusion: The present results showed that Vit C and menthone at higher dose have a good compensatory effect with significant reduction in DNA damages in sperm cells by reversing the adverse effect of ACV on the reproductive system in male rat. [ABSTRACT FROM AUTHOR]