Natural Menthol Research Articles

Synthesis, bioactivity and molecular docking of novel coumarin-quinolinamide containing monocyclic monoterpenes as potential SDH inhibitors

Succinate dehydrogenase inhibitors (SDHI) are widely used in plant antifungal agents. To break the barrier of resistance, a series of new coumarin-quinolinamide SDHI derivatives containing monocyclic monoterpenes were designed and synthesized using natural camphor or natural menthol as lead compounds, and their structures were characterized by FT-IR, 1H NMR, 13C NMR and HRMS. In vitro antifungal activity test results showed that the target compounds had inhibitory activity against most plant pathogenic fungi, especially against Rhizoctonia solani and Phytophthora nicotianae var. nicotianae, which was superior to other fungi. Among them, compounds 11t and 12t showed better inhibitory effects on Rhizoctonia solani than the commercial fungicide tricyclazole, with EC50 of 16.90 mg/L and 27.09 mg/L, respectively. Based on this, the detached leaf assay was used to further explore the in vivo therapeutic and preventive effects of compounds 11t and 12t on rice sheath blight in plants. The results of the antifungal activity test in vivo showed that compound 11t was slightly better than the positive control, while compound 12t was close to the control effect of azoxystrobin. More importantly, the more bioactive compounds 11t and 12t did not affect the germination of cowpea seeds and also did not affect the growth of normal human hepatocytes and kidney cells. Molecular docking experiments showed that the introduction of the diethylamino group could promote the formation of hydrogen bonds between the hydrogen atom on the amide bond of the target compound and residue Tyr91, and compounds 11t and 12t had smaller free energy between the amino acid residue, which would enhance the antifungal activity of the compounds. These studies proved the potential value of this series of compounds for the study of novel amide-based SDHI fungicides.

Ecofriendly dual-function cotton fabric with antibacterial and anti-adhesion properties based on modified natural materials

Ecofriendly fabrics with antibacterial and anti-adhesion properties have been attracted an increasing attention in recent years. Herein, natural menthol modified polyacrylate (PMCA) antibacterial adhesion agent was synthesized by esterification and polymerisation while natural pterostilbene-grafted-chitosan (PGC) antibacterial agent was prepared through Mannich reaction. The antibacterial and anti-adhesion cotton fabric was fabricated through durable PMCA dip finishing and then layer-by-layer self-assembly of PGC. The results showed that the antibacterial adhesion rates and antibacterial rates of the dual-function cotton fabric against Staphylococcus aureus and Escherichia coli reached up to 99.9 %. Its antibacterial adhesion rates improved by 36.1 % and 40.1 % in comparison with those of cotton fabric treated by menthol alone. Meanwhile against S. aureus, the dual-function cotton fabrics improved the antibacterial rates by 56.7 % and 36.4 %, respectively, from those of chitosan- and pterostilbene-treated fabrics. Against E. coli, the improvements were 89.4 % and 24.8 %, respectively. After 20 household washings, the dual-function cotton fabric maintained >80 % of its original anti-adhesion and antibacterial rates against both species. The dual-function cotton fabric also possessed safe and excellent wearability.

Ethanopharmacological Activities of Mentha arvensis: An Updated Review

Economical natural menthol is derived from Mentha arvensis Linn (menthol mint) oil. It is an aromatic perennial herb. The leading Mentha producing state in area and production is Uttar Pradesh and India is the leading exporter contributing about 80% of essential oil, menthol crystal and allied products. It is a native herb from the Labiatae family and is most frequently referred to as “pudina”. It has historically been used to treat ischemic heart disease and hypertension. Terpenoids, alcohols and phenolics are just a few of the bioactive substances that have been identified from this plant. These bioactive compounds’ pharmacological activities include antibacterial, neuroprotective, antioxidant, antiulcer, immunomodulatory, antimutagenic, and anti-tumor properties. Studies on Ayurvedic, unani, and other traditional medical systems have also revealed this plant’s pharmacological capabilities. The current article provides a summary of the plant’s general description, phytochemical ingredients, historical context, and pharmacological qualities

Performance Assessment of Japanese Mint Varieties for Growth under Open Field and Vertical A-Frame Structure

Japanese mint (Mentha arvensis L.), is a member of the family Lamiaceae which is a perennial herbaceous aromatic plant but cultivated as an annual for culinary purpose as leafy vegetable and as natural menthol extraction. It is a major source of raw material for flavours and fragrance industry. Urban regions are losing cultivable land every day and it has become extremely difficult to produce fresh vegetables of high quality. By using vertical structures, vertical space can be utilized while increasing the quality of vegetable production. This experiment was conducted at Department of Vegetable Science, Horticultural College & Research Institute, Periyakulam during 2022-2023 to evaluate the performance of nine varieties viz., Kosi (V1), CIM-Kranti (V2), Himalaya (V3), Kalka (V4), MAS-1 (V5), Saksham (V6), Gomti (V7), Seelayampatti local (V8) and Bangalore hybrid (V9) under open field (G1) and vertical A-frame structure (G2) condition. One vertical A-frame structure is used in this study which contain 516 holes for planting. Among the nine varieties, Saksham (V6) showed increase in growth parameters in both conditions. The observations on growth parameters were recorded for plant height(cm), number of leaves, root length(cm), fresh weight of roots(g) and dry weight of roots(g). Saksham variety in vertical A-frame structure yielded maximum plant height (53.05 cm), number of leaves (112.73), root length (39.92 cm), fresh weight of roots (3.204g) and dry weight of roots (0.874g) followed by the variety CIM-Kranti in vertical A-frame structure (48.83cm, 77.61, 37.75cm, 2.582g and 0.648g). As a result, the interactive action of G2V6 showed maximum growth due to the availability of nutrients in the root system and timely application of water and nutrient helped in better plant parameters.

Inhibitory activity of Mentha spicata oils on biofilms of Proteus mirabilis isolated from burns

Introduction and Aim: Proteus mirabilis is an opportunistic pathogen, infecting humans, through the release of endotoxins and enzymes such as urease, hemolysin, protease, DNase etc. One of the factors contributing to its virulence is its unusual ability to form crystalline biofilms. This study aimed to investigate the effect of Mentha spicata volatile oil on P. mirabilis biofilm formation. Materials and Methods: P. mirabilis was isolated from infected wound of burns of patients using conventional biochemical tests. Vitek 2-Compact System was used to confirm the diagnosis of bacterial isolates. The isolates were tested for their susceptibility to 11 antibiotics. Aqueous and alcoholic extracts as well as Volatile Oil and natural Menthol extracted from M. spicata were tested for their ability to inhibit biofilm formation by P. mirabilis. Results: In this study 16 out of the 45 burn injury samples were tested positive for P. mirabilis. Bacterial isolates were found to be resistant to the drugs Levofloxacin and Norfloxacin, with percentages of 10.2% and 11.8%, respectively. Majority of these isolates had the capacity to produce several virulence factors, including biofilm in variable amounts and the enzymes protease, hemolysin, DNase, and gelatinase. The volatile oil and natural component menthol extracted from M. spicata inhibited the formation of biofilm at increasing concentrations. Conclusion: The volatile oil and the natural menthol compound of M. spicata are effective in inhibiting biofilm formation by P. mirabilis.

A contemporary review on pharmacognosy and pharmacological activities of mentha arvensis.

Mentha arvensis belongs to the family Lamiaceae, it is also called Japanese menthol mint. This plant is endemic to Japan, as well as other parts of Europe, Central Asia, and Eastern Siberia. The pharmacological activity of M. arvensis is anti-microbial, anti-ulcer, radioprotective, cardiovascular, antioxidant activity, anti-allergic activity, and antidiabetic activity, cytotoxic properties, which are consistent with the plant's ethnopharmacological applications. Menthol is obtained from plant leaves of M. arvensis. Natural menthol is widely used in foods, confections, and cigarettes because of the cooling impact it has on the skin and mucous membranes of various body organs. Traditionally it is used as a contraceptive, carminative, antispasmodic, anti-peptic ulcer healing agent, and as a treatment for cough and cold. M. arvensis also used to treat liver and spleen illnesses, as well as asthma and jaundice. The leaf extract is used to treat rheumatoid arthritis, treat infections, and prevent mosquitoes.

Influence of Planting Date on Growth, Yield, and Volatile Oil of Menthol Mint (M. arvensis) Under Marginal Land Conditions

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.

Carrot Roots as Clean and Sustainable Biocatalyst for Obtaining Natural Menthol

Carrot Roots as Clean and Sustainable Biocatalyst for Obtaining Natural Menthol

Concise Synthesis of (–)-Axenol by Using Stereocontrolled Allylic Substitution

Synthesis of (–)-axenol was achieved stereoselectively through allylic substitution to form the quaternary carbon followed by ring-closing metathesis. The key allylic picolinate was synthesized from natural menthol.

Diurnal Effects on Mentha canadensis Oil Concentration and Composition at Two Different Harvests

Japanese cornmint, also known as menthol mint (Mentha canadensis L. syn M. arvensis L.), is an essential oil crop cultivated in several countries in Asia and South America. The plant is currently the only commercially viable source for natural menthol as a result of the high concentration of menthol in the oil compared with other crops. The hypothesis of this study was that harvesting at regular intervals within a 24-hour period would have an effect on essential oil concentration and composition of Japanese cornmint grown at high altitude in northern Wyoming. Flowering plants were harvested every 2 hours on 7 to 8 Aug. and on 14 to 15 Aug. and the essential oil was extracted by steam distillation and analyzed by gas chromatography–mass spectroscopy (GC-MS). The effects of harvest date (Harvest 1 and Harvest 2) and harvest time (12 times within a 24-hour period) were significant on oil concentration and yield of menthol, but only harvest date was significant on the concentration of menthol in the oil. The interaction effect of harvest date and harvest time was significant on water content and on the concentrations of menthol and menthofuran in the oil and on the yield of limonene, menthol, and menthofuran. Overall, the oil concentration in grams per 100 g dried material for the two harvests (1.26 and 1.45, respectively), the concentration of menthol in the oil (67.2% and 72.9%, respectively), and menthol yield (1066 to 849 mg/100 g dried biomass) were higher in plants at Harvest 2 as compared with plants at Harvest 1. The oil concentration was higher in plants harvested at 1100 hr or at 1300 hr and lowest in the plants harvested at 1500 hr. Menthol yield was the highest in plants harvested at 1300 hr and lowest in the plants harvested at 0700 hr, 1900 hr, or at 0300 hr. This study demonstrated that harvesting time within a 24-hour period and harvest date (maturity of the crop) may affect essential oil concentration and composition of Japanese cornmint grown at high altitude in northern Wyoming.

Menthol: A simple monoterpene with remarkable biological properties

Menthol is a cyclic monoterpene alcohol which possesses well-known cooling characteristics and a residual minty smell of the oil remnants from which it was obtained. Because of these attributes it is one of the most important flavouring additives besides vanilla and citrus. Due to this reason it is used in a variety of consumer products ranging from confections such as chocolate and chewing gum to oral-care products such as toothpaste as well as in over-the-counter medicinal products for its cooling and biological effects. Its cooling effects are not exclusive to medicinal use. Approximately one quarter of the cigarettes on the market contain menthol and small amounts of menthol are even included in non-mentholated cigarettes. Natural menthol is isolated exclusively from Mentha canadensis, but can also be synthesised on industrial scale through various processes. Although menthol exists in eight stereoisomeric forms, (-)-menthol from the natural source and synthesised menthol with the same structure is the most preferred isomer. The demand for menthol is high and it was previously estimated that the worldwide use of menthol was 30-32,000 metric tonnes per annum. Menthol is not a predominant compound of the essential oils as it can only be found as a constituent of a limited number of aromatic plants. These plants are known to exhibit biological activity in vitro and in vivo such as antibacterial, antifungal, antipruritic, anticancer and analgesic effects, and are also an effective fumigant. In addition, menthol is one of the most effective terpenes used to enhance the dermal penetration of pharmaceuticals. This review summarises the chemical and biological properties of menthol and highlights its cooling effects and toxicity.

MENTHOL CONTAINING FORMULATION INHIBITS ADZUKI BEAN BEETLE, CALLOSOBRUCHUS CHINENSIS L. (COLEOPTERA; BRUCHIDAE) POPULATION IN PULSE GRAIN STORAGE

ABSTRACT Plants synthesize many industrially useful chemicals for the benefit of humanity. Plant biopesticides are species specific, less harmful to beneficial arthropods, biodegradable and require low cost in developing formulations than synthetic pesticides that are directly developed from petrochemical derivatives. Twenty different tablet formulations prepared from various combinations of promising plant products have been evaluated for stored pulse grains protection. The natural menthol (9.09%) based tablet formulation containing natural binder and carrier agent-Vigna mungo seed powder (73.63%), liquid preservative-Acetic acid (11.36%), solid powdered preservative - sodium benzoate (5.68%) and edible lemon yellow colour (0.22%) (Treatment - XVII) applied once was found to be the most suitable for the management of adzuki bean beetle, Callosobruchus chinensis L. adult during pulse grains storage period of three and six months. The two tablets/250g grains comprising menthol (XVII) was found to reduce significantly 100% C. chinensis population in jars containing grains of both Cicer arietinum and Lens esculenta up to six months storage period. The beetle population did not increase as compared to average increase range of 245 to 1515 adult beetle populations in C. arietinum and 1825 to 3346 in L. esculenta in other treatments and untreated control during three months of storage. Result indicates that menthol containing cost effective tablets formulation may be developed at commercial level to protect the pulse grains attack of adzuki bean beetles during storage in homes and market places.

Effect of menthol coated craft paper on corrosion of copper in HCl environment

Natural menthol was coated on craft paper by impregnation and studied as volatile corrosion inhibitor for copper in hydrochloric acid environment. The effect of menthol on copper corrosion was studied by gravimetric and electrochemical methods such as potentiodynamic polarization and electrochemical impedance measurements. The results indicate that menthol adsorbs on the metal surface, which protects copper against further corrosion. The adsorption behaviour of menthol on copper surface was found to obey Temkin’s adsorption isotherm.

Effects of Menthol on Skeletal Muscle Blood Flow

Commercially sold menthol balms and ointments are commonly used after exercise to retard inflammation and to serve as a cooling pain reliever. However, the effect of menthol on blood flow response is not well established. PURPOSE: The purpose of this study was to investigate the effects of a natural menthol product (3.5%) on blood flow in the forearm. METHODS: Twelve males and females between the ages of 21–32 years (24 ± 4 years) were recruited to participate in the study. Blood flow was measured in the brachial artery using quantitative Doppler ultrasound before and after the application of a 3.5% menthol ointment to the forearm. The application of ice to the other forearm of each subject served as a control for the study. Forearm surface area was measured (553 ± 84 cm2) for each person and used to standardize the amount of ointment applied for each person (2.77 ± 0.42 mL). Continuous blood flow measurement for 5 minutes before and for 10 minutes after the application of the ointment or the ice allowed for the determination of the time course of the blood flow response. The blood flow response was averaged after the application of the menthol or ice to give blood flow measurements at 30, 60, 120, 180, 240, and 600 seconds, respectively. RESULTS: Blood flow was not significantly different between the conditions at baseline or after the application of the menthol ointment or the ice (p = 0.204). The average blood flow response over the 10 minutes post application was reduced by approximately 30% compared to baseline. A repeated measures ANOVA indicated that there was a significant time effect for blood flow (p ≤ 0.001). Post hoc analysis indicated that blood flow was significantly reduced from baseline at 30, 60, 120, 180, and at 600 s (p ≤ 0.040). Furthermore, the blood flow at 30 and 60 s was reduced (≈ 43%) to a greater extent than at 120, 180, 240, and 600 s (≈ 23%) (p ≤ 0.039) compared to baseline. There was no significant difference between 30 and 60 seconds or between any time points after 120second. CONCLUSIONS: The application of a 3.5% menthol ointment elicits an immediate decrease in blood flow for up to 10 minutes after its application. The reduction in blood flow was similar to the response associated with the ice condition. Supported by the VP of Research at UofL

Poly(phenyleneethynylene) polymers bearing glucose substituents as promising active layers in enantioselective chemiresistors

Poly(phenyleneethynylene) (PPE) conjugated polymers bearing glucose units are used as enantioselective active layers in vapor-sensing devices. As a novel approach, a conjugated polymer bearing chiral pendant groups is used to detect different enantiomers, natural and synthetic menthol molecules in the present case. The surface analytical characterization of the organic layer reveals a compact and smooth morphology. By means of a quartz crystal microbalance revealing system, the polymer bearing glucose chiral sites is demonstrated to interact more favorably with the natural menthol. Promising perspectives are seen for the use of such polymers in chiral, chemically sensitive resistors or even transistors.

Enantioselective Synthesis of L‐CCG‐I.

Introduction of natural menthol as the chiral auxiliary in a c-Br-R,â-unsaturated ester leads to enantioselective generation of three chiral centers in a single step on reaction with a glycine anion equivalent to provide L-CCG-I in 94% ee.

Enantioselective Synthesis of L-CCG-I.

Introduction of natural menthol as the chiral auxiliary in a gamma-Br-alpha,beta-unsaturated ester leads to enantioselective generation of three chiral centers in a single step on reaction with a glycine anion equivalent to provide L-CCG-I in 94% ee.

NEW PRACTICES IN THE CULTIVATION OF THE MINT, MENTHA ARVENSIS IN THE INDO-GANGETIC PLAINS

India is the world's dominant producer of crude Mentha arvensis oil, and exporter of its processed derivative, natural menthol. This status has been achieved through superior product price competitiveness resulting from progressive agronomic improvements that include a transition from cultivation of this mint as a semi-perennial to an annual crop. This paper describes and analyses recent developments in Indian M. arvensis cultivation.Observations were made during 1998/99 and 1999/2000 in the fields of 295 farmers in the central Indo-Gangetic plains area. The criteria recorded included: mint cultivars used; the planting, weeding, irrigation, pesticide application and harvesting schedules; crop health in relation to diseases and pests; yields of the harvested herb and the distilled essential oil; the oil menthol content; and the net income.Most of the farmers used the cultivar, Kosi. The performance and returns of Kosi transplanted in April had proved superior to Kosi and Shivalik suckers and to transplanted Shivalik. The returns from late-transplanted Kosi were in the range of Rupees (Rs) 25 000 to Rs 40 000 ha−1 (Rs 50≈US$1), similar to those from Kosi suckers and much higher than for both transplanted and suckers of Shivalik. This survey revealed that rotations of rice (Oryza sativa) with chickpea (Cicer arietinum) and mint, and pigeonpea (Cajanus cajan) with wheat (Triticum aestivum) and mint could be profitable in the central Indo-Gangetic plains. They also conserved inputs and were preferable to the conventional rice-wheat rotation. A re-survey in the summer of 2002 confirmed that recommendations made to farmers have led to the adoption of the Kosi and Himalaya cultivars in 80% of the survey region and that 70% of mint cultivation in the area occurs in the summer season.

Characteristics of menthol mint Mentha arvensis cultivated on industrial scale in the Indo-Gangetic plains

Mentha arvensis L. (menthol mint) oil is the source of commercial natural menthol. This industrial crop is now cultivated in about 0.145 million ha in the Indian state of Uttar Pradesh (UP) and several other states encompassing Indo-Gangetic plains. Considerable variation has been reported in the yield and quality of oil obtained from the crops of menthol mint varieties Himalaya and Kosi taken in the area. A follow up study was made to ascertain the cause(s) of such variation in many villages of selected districts of UP. The soils sampled from the fields were studied for variability in reaction, salinity, organic carbon content, the contents of the major nutrients nitrogen, phosphorous and potassium and micro-nutrients manganese, iron, copper and zinc and crops of mint on the concerned fields were characterized for the herb, essential oil and menthol yields. The observations made in 69 farmers’ fields have indicated variation in soil characteristics, as well as herb, essential oil and menthol yields from the crops taken on them. However, herbs harvested from different fields did not differ much in their oil content. Imbalance in N, P and K supplements to the field was observed; it seemed to arise from unnecessary emphasis on urea application without concomitant K and P supplementation. The fields were particularly deficient in Mn among the micronutrients. There was need for heavier application of K, Cu, Zn, and Mn together with sufficient amount of N and P to obtain better oil yields. To increase oil yield was inferred as the best means to increase menthol production from the fields of Indo-Gangetic plains.

Solid-Phase Microextraction--Gas Chromatographic--Mass Selective Detection Analysis of Selected Sources of Menthol

Manual solid-phase microextraction (SPME) coupled with gas chromatography-mass selective detection has been shown to be a rapid, precise, and reliable method for testing the origin and purity of menthol samples. Exposure of a 65-μm carboxenpolydimethylsiloxane fiber to the headspace above a menthol sample held at 50°C in a sealed vial provides for excellent signal-to-noise responses for a variety of volatile components. Detection differences in menthol compositions are based on documenting predictable changes in the ratios of identified and/or unknown components adsorbed onto the SPME fiber. Differences in composition can be detected as a function of manufacturing site using this approach. In addition, the presence of added synthetic menthol can be detected in the natural samples employing the same principle, thus assisting in determining the purity of the natural menthol.