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Keywords = menthofuran

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16 pages, 1804 KiB  
Article
GABA and Octopamine Receptors as Potential Targets for Fumigant Actions of Bursera graveolens Essential Oil Against Callosobruchus maculatus and Callosobruchus chinensis
by Luis O. Viteri, Maria José González, Pedro B. Silva, Jonatas M. Gomes, Thiago Svacina, Lara T. M. Costa, Eduardo Valarezo, Javier G. Mantilla-Afanador, Osmany M. Herrera, Raimundo W. S. Aguiar, Gil R. Santos and Eugênio E. Oliveira
J. Xenobiot. 2025, 15(3), 91; https://doi.org/10.3390/jox15030091 - 12 Jun 2025
Viewed by 1284
Abstract
Cowpea, Vigna sp., is an important, low-cost protein source in subtropical and semi-arid regions, where seasonal rainfall makes storage necessary. However, the weevils Callosobruchus maculatus and C. chinensis cause significant grain losses during storage. While synthetic fumigants are commonly used to control these [...] Read more.
Cowpea, Vigna sp., is an important, low-cost protein source in subtropical and semi-arid regions, where seasonal rainfall makes storage necessary. However, the weevils Callosobruchus maculatus and C. chinensis cause significant grain losses during storage. While synthetic fumigants are commonly used to control these pests, their risks to mammals have prompted the search for safer alternatives. In this context, we tested palo santo, Bursera graveolens, essential oil with limonene, α-phellandrene, o-cymene and β-phellandrene, menthofuran, and germacrene-D as a sustainable approach. This plant is readily accessible, produces high fruit yields, and is used in households for various purposes. We evaluated the fumigant toxicity, repellency, and ovicidal effects of B. graveolens essential oil on both Callosobruchus species. Our results showed that B. graveolens oil was toxic to C. maculatus (LC50 = 80.90 [76.91–85.10] µL) and C. chinensis (LC50 = 63.9 [60.95–66.99] µL), with C. chinensis being more susceptible (SR = 1.27). Molecular docking analyses revealed that all the oil’s compounds bind to both the GABA and octopamine receptors, exhibiting high energy affinities; however, germacrene shows the strongest affinity in these receptors. C. chinensis was strongly repelled at all concentrations, while C. maculatus was repelled only at lethal concentrations. No ovicidal effect was observed in either species. In conclusion, our findings suggest that B. graveolens essential oil is a promising and sustainable protectant for stored cowpeas in small-scale storage units. Full article
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22 pages, 4280 KiB  
Article
Essential Oil Composition and Physiology of Three Mentha Genotypes Under Shaded Field Conditions
by Charlotte Hubert-Schöler, Saskia Tsiaparas, Katharina Luhmer, Marcel Dieter Moll, Maike Passon, Matthias Wüst, Andreas Schieber and Ralf Pude
Plants 2024, 13(22), 3155; https://doi.org/10.3390/plants13223155 - 9 Nov 2024
Cited by 1 | Viewed by 2215
Abstract
Mentha spp. are commonly used for the production of tea and for the extraction of essential oils (EOs). The key factor of mint quality is the content and composition of the EO. Health-promoting compounds such as menthol are desirable, whereas the presence of [...] Read more.
Mentha spp. are commonly used for the production of tea and for the extraction of essential oils (EOs). The key factor of mint quality is the content and composition of the EO. Health-promoting compounds such as menthol are desirable, whereas the presence of potentially health-damaging compounds such as menthofuran should be avoided. This study examines the effect of shading on the EO content and composition of three Mentha genotypes (Mentha × piperita ‘Multimentha’, Mentha × piperita ‘Fränkische Blaue’ and Mentha rotundifolia ‘Apfelminze’). The Mentha genotypes were cultivated in field trials for two years (2022–2023). Each genotype was shaded with a shading net (50% photosynthetic active radiation (PAR) reduction), and a control without shading was prepared. EO content was determined by steam distillation and EO composition was characterized by GC-MS analysis. Furthermore, biomass, vegetation indices (VIs) and the electron transport rate (ETR) were analyzed. While shading led to higher plant heights, higher EO content and a slightly reduced amount of undesired EO compounds, the unshaded control yielded a higher biomass accumulation. Significant genotypic differences were determined. In conclusion, the benefits of shading depend on the intended use and genotype selection. Full article
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20 pages, 5429 KiB  
Article
Modulation of Phytochemical Pathways and Antioxidant Activity in Peppermint by Salicylic Acid and GR24: A Molecular Approach
by Parisa Jariani, Manijeh Sabokdast, Taraneh Karami Moghadam, Farzaneh Nabati and Beata Dedicova
Cells 2024, 13(16), 1360; https://doi.org/10.3390/cells13161360 - 15 Aug 2024
Cited by 5 | Viewed by 1342
Abstract
This study uncovers the potential of salicylic acid (SA) and synthetic Strigolactone (GR24) in enhancing menthol biosynthesis and antioxidant defense mechanisms in Mentha piperita L. Our comprehensive analysis, which included a series of controlled experiments and data analysis of the effects of these [...] Read more.
This study uncovers the potential of salicylic acid (SA) and synthetic Strigolactone (GR24) in enhancing menthol biosynthesis and antioxidant defense mechanisms in Mentha piperita L. Our comprehensive analysis, which included a series of controlled experiments and data analysis of the effects of these phytohormones on enzymatic antioxidants catalase (CAT) and ascorbate peroxidase (APX) and non-enzymatic antioxidants, including carotenoids and proline, revealed promising results. The study also examined their impact on lipid peroxidation, hydrogen peroxide levels, and the expression of genes critical to menthol and menthofuran synthesis. The results indicated that SA and GR24 significantly increased menthol production and reduced the levels of menthofuran and pulegone, suggesting upregulation in the plant’s innate defense systems. Furthermore, the activities of CAT and APX were elevated, reflecting a strengthened antioxidant response. Interestingly, the menthofuran synthase (MFS) was higher in the control group. At the same time, pulegone reductase (PR) genes and menthol dehydrogenase (MDH) gene expression were upregulated, highlighting the protective effects of SA and GR24. These findings underscore the potential of SA and GR24 to serve as effective bio-stimulants, improving the quality and resilience of peppermint plants and thereby contributing to eco-friendly agricultural practices in pollution-stressed environments. Full article
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13 pages, 791 KiB  
Article
Effect of Capsule Burst in Cigarette Filters on the Compound Composition of Mainstream Cigarette Smoke
by Hyeon-Su Lim, Ji-Sang You and Heung-Bin Lim
Toxics 2023, 11(11), 901; https://doi.org/10.3390/toxics11110901 - 3 Nov 2023
Cited by 2 | Viewed by 4242
Abstract
The number of cigarette capsule users is increasing; however, a comprehensive epidemiological investigation comparing the harmfulness of capsule and non-capsule cigarettes, particularly concerning the composition of flavor components and mainstream smoke, is lacking. The present study aimed to investigate the effect of capsule [...] Read more.
The number of cigarette capsule users is increasing; however, a comprehensive epidemiological investigation comparing the harmfulness of capsule and non-capsule cigarettes, particularly concerning the composition of flavor components and mainstream smoke, is lacking. The present study aimed to investigate the effect of capsule burst on the compound composition of mainstream smoke by quantifying the Hoffmann list and flavor (geraniol, eugenol, menthofuran, and pulegone) in mainstream smoke with and without crushing the capsules. The findings indicate that while tar values tended to increase when the capsules were burst, there was no significant change observed in the other Hoffmann list components, such as nicotine, benzo[α]pyrene, tobacco-specific nitrosamines, aromatic amines, and phenolics. However, when the capsules burst, menthofuran and pulegone, which were present in the capsule and could cause toxicity, were found in the mainstream smoke via the International Standard Organization (1.5–4.0 μg/cig and 5.13–6.00 μg/cig smoking regime) and Health Canada Intense (12.8–18.2 μg/cig and 22.77–24.67 μg/cig smoking regime). Therefore, understanding the capsule composition is important, as the toxic components of the capsules can be inhaled as smoke, posing a potential health risk. Full article
(This article belongs to the Special Issue 2nd Edition: Tobacco Smoke Exposure and Tobacco Product Use)
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11 pages, 1158 KiB  
Article
Inducing the Production of Secondary Metabolites by Foliar Application of Methyl Jasmonate in Peppermint
by Wafae Kandoudi, Szilvia Tavaszi-Sárosi and Eva Németh-Zámboriné
Plants 2023, 12(12), 2339; https://doi.org/10.3390/plants12122339 - 16 Jun 2023
Cited by 4 | Viewed by 2111
Abstract
Mentha x piperita is a major source of secondary metabolites (SMs), and developing tools to enhance these compounds would be beneficial to meet the increasing demand in the industry. Elicitation by plant hormones became a new strategy to reach this goal. Three experiments [...] Read more.
Mentha x piperita is a major source of secondary metabolites (SMs), and developing tools to enhance these compounds would be beneficial to meet the increasing demand in the industry. Elicitation by plant hormones became a new strategy to reach this goal. Three experiments in a climatic chamber and two experiments in an open field were conducted with peppermint to explore the effect of methyl jasmonate (MeJa) on the essential oil (EO) content, EO composition, and the total phenolic content (TPC). The treatment was applied for all experiments by spraying the aerial parts of the plants with a dosage of 2 mM MeJa twice. The treatment influenced all the parameters studied in the trials. The volatile content increased by 9–35%; however, in one trial it remained unchanged. The treatment also affected the main compounds of the EO. Menthone increased significantly in two trials while pulegone and menthofuran decreased. In the case of menthol, the change may also be influenced by the phenological and developmental stages of the plants. In the majority of cases, the TPC was also elevated considerably due to the treatments. MeJa treatments may have promising effects in influencing the accumulation of biologically active compounds and the quality of the drug; therefore, further systematic studies are needed to optimize the technology in vivo. Full article
(This article belongs to the Special Issue Plant-Derived Natural Products and Their Applications)
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18 pages, 3454 KiB  
Article
Mentha aquatica L. Populations from the Hyrcanian Hotspot: Volatile Oil Profiles and Morphological Diversity
by Mohammad Bagher Hassanpouraghdam, Ahmad Mohammadzadeh, Mohammad Reza Morshedloo, Mohammad Asadi, Farzad Rasouli, Lamia Vojodi Mehrabani and Agnieszka Najda
Agronomy 2022, 12(10), 2277; https://doi.org/10.3390/agronomy12102277 - 23 Sep 2022
Cited by 9 | Viewed by 2393
Abstract
Mentha aquatica L. (Lamiaceae) is found in different parts of Iran. Its essential oil and preparations regulate bile function and are used as a stomach tonic and disinfectant. This study investigates the morphological and essential oil diversity of M. aquatica populations from the [...] Read more.
Mentha aquatica L. (Lamiaceae) is found in different parts of Iran. Its essential oil and preparations regulate bile function and are used as a stomach tonic and disinfectant. This study investigates the morphological and essential oil diversity of M. aquatica populations from the Hyrcanian hotspot of Iran. Plant samples were collected from Gilan, Golestan, and Mazandaran provinces in the Caspian Region for analysis. The results showed significant differences among the studied ecotypes for the stem diameter, collar diameter, number of inflorescences, length and width of inflorescence, sepal diameter, sepal length, and secondary stem length number. Principal component analysis showed that the first seven principal components explained 90.6% of the total variation. Moreover, essential oil concentration varied widely from 1.13% for a sample from Behshahr-Mazandaran, down to 0.27% for one from Abbas abad-Mazandaran. GC–MS analysis identified 29 constituents that accounted for 91% of the total essential oil. The main components of the essential oil were menthofuran (13.21–52.46%), 1,8-cineole (12.42–25.55%), (E)-caryophyllene (3.18–15.43%), viridiflorol (1.04–11.16%), germacrene D (1.70–8.29%), caryophyllene oxide (0.51–4.96%), neryl acetate (1.11–4.95%), p-cymene (1.55–4.77%), and β-pinene (1.7–3.45%). Overall, meaningful diversity was recorded among the populations; Rahimabad-Gilan and Behshahr-Mazandaran would be reliable selections for the food and pharmaceutical industries due to their higher yields and content of α-pinene, 1, 8-cineole, menthofuran, viridiflorol, and β-caryophyllene. Further evaluation of populations from diverse habitats is needed to guide future breeding programs. Full article
(This article belongs to the Special Issue Chemical Diversity, Yield and Quality of Aromatic Plant)
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20 pages, 2222 KiB  
Article
Chemotypes and Their Stability in Mentha longifolia (L.) L.—A Comprehensive Study of Five Accessions
by Katalin Patonay, Helga Szalontai, Péter Radácsi and Éva Zámboriné-Németh
Plants 2021, 10(11), 2478; https://doi.org/10.3390/plants10112478 - 16 Nov 2021
Cited by 9 | Viewed by 3483
Abstract
Mentha longifolia (L.) L. is the most widespread wild-growing mint species found, and its chemical composition is extremely diverse. We studied the essential oil (EO) yield, composition, and chemotaxonomy of five, northern Hungarian accessions of the species in a cultivation experiment covering two [...] Read more.
Mentha longifolia (L.) L. is the most widespread wild-growing mint species found, and its chemical composition is extremely diverse. We studied the essential oil (EO) yield, composition, and chemotaxonomy of five, northern Hungarian accessions of the species in a cultivation experiment covering two vegetation years at two parallel sites. The long-term goal is to establish the cultivation of this stress-tolerant species in Hungary as a source of flavoring and preservative agents for commercial use. Essential oil yield (1–2 mL/100 g) was observed to be dependent on both the accession and the year. Accession HV1 is assumed to be a new, presumably rare chemotype containing carvacrol (19.28–20.56%), 1,8-cineole (14.87–17.45%), thymol (13.36–13.90%), carvacryl acetate (8.81–10.40%), and para-cymene (7.24–8.01%). Only minor fluctuations occurred in concentrations of these constituents due to habitats and years. A radical change in essential oil composition was observed in accession HV2, as one batch was based on thymol (19.79%) and 1,8-cineole (14.93%), while the others were rich in dihydrocarvone isomers (up to 69%). Although this needs further investigation, it does explain the coexistence of limonene-oxo and γ-terpinene pathways in horsemint. According to the literature, the pathway leading to thymol isomers and/or esters may be rare in the entire Mentha genus. We also demonstrated that known chemotypes of horsemint may differ in variability of their EO composition. Our results also led to the conclusion that any declaration on chemotype needs detailed examination and is not realistic on the basis of a single sample. Assumptions were made about the potential areas of utilization: beside fragrance and flavoring uses of essential oils free from pulegone and menthofurane, thymol-based ones may be used as antioxidative and anti-spoilage agents. Full article
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12 pages, 3134 KiB  
Article
Single Wavelengths of LED Light Supplement Promote the Biosynthesis of Major Cyclic Monoterpenes in Japanese Mint
by Takahiro Ueda, Miki Murata and Ken Yokawa
Plants 2021, 10(7), 1420; https://doi.org/10.3390/plants10071420 - 12 Jul 2021
Cited by 13 | Viewed by 4371
Abstract
Environmental light conditions influence the biosynthesis of monoterpenes in the mint plant. Cyclic terpenes, such as menthol, menthone, pulegone, and menthofuran, are major odor components synthesized in mint leaves. However, it is unclear how light for cultivation affects the contents of these compounds. [...] Read more.
Environmental light conditions influence the biosynthesis of monoterpenes in the mint plant. Cyclic terpenes, such as menthol, menthone, pulegone, and menthofuran, are major odor components synthesized in mint leaves. However, it is unclear how light for cultivation affects the contents of these compounds. Artificial lighting using light-emitting diodes (LEDs) for plant cultivation has the advantage of preferential wavelength control. Here, we monitored monoterpene contents in hydroponically cultivated Japanese mint leaves under blue, red, or far-red wavelengths of LED light supplements. Volatile cyclic monoterpenes, pulegone, menthone, menthol, and menthofuran were quantified using the head-space solid phase microextraction method. As a result, all light wavelengths promoted the biosynthesis of the compounds. Remarkably, two weeks of blue-light supplement increased all compounds: pulegone (362% increase compared to the control), menthofuran (285%), menthone (223%), and menthol (389%). Red light slightly promoted pulegone (256%), menthofuran (178%), and menthol (197%). Interestingly, the accumulation of menthone (229%) or menthofuran (339%) was observed with far-red light treatment. The quantification of glandular trichomes density revealed that no increase under light supplement was confirmed. Blue light treatment even suppressed the glandular trichome formation. No promotion of photosynthesis was observed by pulse-amplitude-modulation (PAM) fluorometry. The present result indicates that light supplements directly promoted the biosynthetic pathways of cyclic monoterpenes. Full article
(This article belongs to the Special Issue The Effects of LED Light Spectra and Intensities on Plant Growth)
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17 pages, 2320 KiB  
Article
Inter-Individual Variability in Acute Toxicity of R-Pulegone and R-Menthofuran in Human Liver Slices and Their Influence on miRNA Expression Changes in Comparison to Acetaminophen
by Tomáš Zárybnický, Petra Matoušková, Bibiána Lancošová, Zdeněk Šubrt, Lenka Skálová and Iva Boušová
Int. J. Mol. Sci. 2018, 19(6), 1805; https://doi.org/10.3390/ijms19061805 - 19 Jun 2018
Cited by 20 | Viewed by 5357
Abstract
Monoterpenes R-pulegone (PUL) and R-menthofuran (MF), abundant in the Lamiaceae family, are frequently used in herb and food products. Although their hepatotoxicity was shown in rodent species, information about their effects in human liver has been limited. The aim of our study was [...] Read more.
Monoterpenes R-pulegone (PUL) and R-menthofuran (MF), abundant in the Lamiaceae family, are frequently used in herb and food products. Although their hepatotoxicity was shown in rodent species, information about their effects in human liver has been limited. The aim of our study was to test the effects of PUL, MF and acetaminophen (APAP, as a reference compound) on cell viability and microRNA (miRNA) expression in human precision-cut liver slices. Slices from five patients were used to follow up on the inter-individual variability. PUL was toxic in all liver samples (the half-maximal effective concentration was 4.0 µg/mg of tissue), while MF and surprisingly APAP only in two and three liver samples, respectively. PUL also changed miRNA expression more significantly than MF and APAP. The most pronounced effect was a marked decrease of miR-155-5p expression caused by PUL even in non-toxic concentrations in all five liver samples. Our results showed that PUL is much more toxic than MF and APAP in human liver and that miR-155-5p could be a good marker of PUL early hepatotoxicity. Marked inter-individual variabilities in all our results demonstrate the high probability of significant differences in the hepatotoxicity of tested compounds among people. Full article
(This article belongs to the Special Issue Hepatotoxicity: Molecular Mechanisms and Pathophysiology)
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10 pages, 379 KiB  
Article
Quantitative Comparative Analysis of the Bio-Active and Toxic Constituents of Leaves and Spikes of Schizonepeta tenuifolia at Different Harvesting Times
by Sheng Yu, Yiwen Chen, Li Zhang, Mingqiu Shan, Yuping Tang and Anwei Ding
Int. J. Mol. Sci. 2011, 12(10), 6635-6644; https://doi.org/10.3390/ijms12106635 - 10 Oct 2011
Cited by 32 | Viewed by 8123
Abstract
A GC-MS-Selected Ion Monitoring (SIM) detection method was developed for simultaneous determination of four monoterpenes: (-)-menthone, (+)-pulegone, (-)-limonene and (+)-menthofuran as the main bio-active and toxic constituents, and four other main compounds in the volatile oils of Schizonepeta tenuifolia (ST) leaves and spikes [...] Read more.
A GC-MS-Selected Ion Monitoring (SIM) detection method was developed for simultaneous determination of four monoterpenes: (-)-menthone, (+)-pulegone, (-)-limonene and (+)-menthofuran as the main bio-active and toxic constituents, and four other main compounds in the volatile oils of Schizonepeta tenuifolia (ST) leaves and spikes at different harvesting times. The results showed that the method was simple, sensitive and reproducible, and that harvesting time was a possible key factor in influencing the quality of ST leaves, but not its spikes. The research might be helpful for determining the harvesting time of ST samples and establishing a validated method for the quality control of ST volatile oil and other relative products. Full article
(This article belongs to the Section Biochemistry)
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