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PubMed2002

Antibacterial and antifungal activity of essential oils of Mentha suaveolens.

The essential oils (EO) of Mentha suaveolens, a wild Labiatae, which grows in several regions in Morocco, were characterized and their antimicrobial activity assessed. The main aromatic constituents of this plant, as characterized by IR, NMR and MS studies, were pulegone, piperitenone oxide (PEO) and piperitone oxide (PO) occurring in different amounts depending on the subspecies. These constituents as well as a series of other aromatic products such as carvone, limonene and menthone, were tested for their antimicrobial activity against 19 bacteria including Gram-positive and Gram-negative and against three fungi, using solid phase and microtitration assays. Pulegone-rich essential oil inhibited efficiently all the micro-organisms tested with MICs ranging between 0.69 and 2.77 ppm. Among the components from Mentha suaveolens EO, pulegone was the most effective against the tested microorganisms, followed by PEO and PO. The structure-activity relationship is discussed on the basis of the activity of the other aromatic derivatives tested such as carvone, limonene, menthone and the profile of the essential oils of Mentha suaveolens was compared with other Mentha species.

Anti-Bacterial Agents↗
PubMed2005

New monoterpenes from Mentha microphylla.

Four new monoterpenes, (1 R*,2 S*)-1,2-dihydroxy- p-menth-4(8)-en-3-one ( 1), (4 S*)-4-hydroxy- p-mentha-1,8-dien-3-one ( 2), (4 S*)-4-methoxy- p-mentha-1,8-dien-3-one ( 3), and (3 R*,4 R*,6 S*)-3-acetoxy-6-hydroxy- p-mentha-1,8-diene ( 4) together with four known compounds have been isolated from the aerial parts of Mentha microphylla. The structures were determined using spectroscopic methods particularly high resolution (1)H-, (13)C-NMR as well as 2D (1)H- (1)H COSY, HMQC and HMBC analysis.

Humans↗
PubMed2004

[Diversity of phytophagous and pathogens and their damage to mints (Mentha)].

UNLABELLED: The aim of this work was to estimate the phytopathologic condition of mints grown and self-growing in Kaunas Botanical Garden of Vytautas Magnus University and elsewhere in Lithuania; and to identify the specific constitution, the spread and damage of the main pests and disease agents. MATERIAL AND METHODS: Observations and examination were carried out with two local, four introduced mint species and with four hybrids in 1997-2003. We estimated the plant condition by identifying the intensity of the diseases and the abundance, spreading and damage of the pests. During the study we detected and identified the following pests--agents of diseases: Puccinia menthae, Erysiphe biocellata and Verticillium sp.; and phytophagous: Tetranychus urticae, Eupteryx atropunctata, Ovatus crataegarius, Polia persicariae, Agriotes lineatus, Chrysomela coerulans, Cassida viridis, Longitarsus lycopi. The most dangerous mint disease in Lithuania is rust; pests causing more harm are: Eupteryx atropunctata, Longitarsus lycopi. According to our data the least resistant species to most diseases and pests were Mentha arvensis and Mentha piperita, however separate samples of these species were exceptionally resistant. More resistant species was Mentha spicata and its hybrids.

Ecology↗
PubMed2001

Different stereoselectivity in the reduction of pulegone by Mentha species.

Aqueous solutions of [2H]-labeled pulegone enantiomers were fed to Mentha spicata ssp. spicata L. and Mentha spicata ssp. crispata L. shoot tip and first leaf pair. After solid phase microextraction the essential oil was analysed with enantioselective multidimensional gas chromatography/mass spectrometry. Both Mentha spicata species were able to convert labelled (1R)- and (1S)-pulegone at the same rate into the corresponding menthone and isomenthone, indicating an unspecific process. The reduction of both pulegone enantiomers preferably led to the cis-stereoisomers. The observed stereoselectivity is completely different from those of pulegone reduction by Mentha x piperita L.

Cyclohexane Monoterpenes↗
PubMed2006

Modulatory effects of Mentha piperita on lung tumor incidence, genotoxicity, and oxidative stress in benzo[a]pyrene-treated Swiss albino mice.

Mentha piperita or peppermint is currently used for alleviating nausea, flatulence, and vomiting. In the present investigation, we evaluated the chemopreventive, antigenotoxic, and antioxidative effects of an aqueous extract of Mentha piperita leaves. One-day-old Swiss albino mice were treated with a single subcutaneous injection of 0.5 mg benzo[a]pyrene (BP) and then given either water or a Mentha extract (ME; 1 g/kg body weight) by gavage starting at 3 weeks of age (weaning). The mice were killed at 9 weeks of age and tested for lung tumor incidence (chemoprevention); bone marrow micronucleus and chromosome aberration frequency (antigenotoxicity); and levels of liver and lung sulfhydral groups, superoxide dismutase (SOD) and catalase (CAT) activity, and lipid peroxidation (LPO) (antioxidative properties). The ME treatment resulted in a significant reduction in the number of lung adenomas from an incidence of 67.92% in animals given only BP to 26.31%, an inhibition of 61.26%. Tumor multiplicity was 1.22 in the BP-alone group and 1.15 in the BP + ME group. In addition, compared with the animals in the BP-alone group, ME reduced the frequency of chromosomal aberrations and micronuclei in bone marrow cells and decreased the levels of LPO and increased reduced glutathione content, and SOD and CAT activities in liver as well as lung. The results of this study indicate that ME is chemopreventive and antigenotoxic when given subsequent to an initiating dose of BP in newborn Swiss albino mice. The chemopreventive action and antigenotoxic effects observed in the present study may be due to the antioxidative properties of ME.

Adenoma↗
PubMed2006

Giardia lamblia: the effects of extracts and fractions from Mentha x piperita Lin. (Lamiaceae) on trophozoites.

Giardia lamblia is a parasite that causes giardiasis in humans and other mammals. The common treatment includes different classes of drugs, which were described to produce unpleasant side effects. Mentha x piperita, popularly known as peppermint, is a plant that is frequently used in the popular medicine to treat gastrointestinal symptoms. We examined the effects of crude extracts and fractions from peppermint against G. lamblia (ATCC 30888) on the basis of trophozoite growth, morphology and adherence studies. The methanolic, dichloromethane and hexanic extracts presented IC(50) values of 0.8, 2.5 and 9.0microg/ml after 48h of incubation, respectively. The aqueous extract showed no effect against the trophozoites with an IC(50)>100microg/ml. The aqueous fraction presented a moderate activity with an IC(50) of 45.5microg/ml. The dichloromethane fraction showed the best antigiardial activity, with an IC(50) of 0.75microg/ml after 48h of incubation. The morphological and adhesion assays showed that this fraction caused several alterations on plasma membrane surface of the parasite and inhibited the adhesion of G. lamblia trophozoites. Cytotoxic assays showed that Mentha x piperita presented no toxic effects on the intestinal cell line IEC-6. Our results demonstrated antigiardial activity of Mentha x piperita, indicating its potential value as therapeutic agent against G. lamblia infections.

Animals↗
PubMed2003

Antimicrobial and antioxidant activities of three Mentha species essential oils.

The present study describes the antimicrobial activity and free radical scavenging capacity (RSC) of essential oils from Mentha aquatica L., Mentha longifolia L., and Mentha piperita L. The chemical profile of each essential oil was determined by GC-MS and TLC. All essential oils exhibited very strong antibacterial activity, in particularly against Esherichia coli strains. The most powerful was M. piperita essential oil, especially towards multiresistant strain of Shigella sonei and Micrococcus flavus ATTC 10,240. All tested oils showed significant fungistatic and fungicidal activity [expressed as minimal inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) values, respectively], that were considerably higher than those of the commercial fungicide bifonazole. The essential oils of M. piperita and M. longifolia were found to be more active than the essential oil of M. aquatica. Especially low MIC (4 microL/mL) and MFC (4 microL/mL) were found with M. piperita oil against Trichophyton tonsurans and Candida albicans (both 8 microL/mL). The RSC was evaluated by measuring the scavenging activity of the essential oils on the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and OH radicals. All examined essential oils were able to reduce DPPH radicals into the neutral DPPH-H form, and this activity was dose-dependent. However, only the M. piperita oil reduced DPPH to 50 % (IC50 = 2.53 microg/mL). The M. piperita essential oil also exhibited the highest OH radical scavenging activity, reducing OH radical generation in the Fenton reaction by 24 % (pure oil). According to GC-MS and TLC (dot-blot techniques), the most powerful scavenging compounds were monoterpene ketones (menthone and isomenthone) in the essential oils of M. longifolia and M. piperita and 1,8-cineole in the oil of M. aquatica.

Anti-Bacterial Agents↗
PubMed2005

Inhibitory effects of the essential oil of Mentha pulegium on the isolated rat myometrium.

The effects of the essential oil of Mentha pulegium L. (EOMP), a plant commonly known as "pennyroyal" or "poejo" that is used in folk medicine as an abortifaceant, were assessed on the isolated rat myometrium. Myometrial strips were stimulated with 10 nM oxytocin or 10 microM PGF (2alpha). EOMP (10 - 300 microg/mL) concentration-dependently and reversibly inhibited the amplitude of oscillatory contractions, being approximately 3-fold more active against contractions stimulated by oxytocin than those by PGF (2alpha) (IC (50) values of 45.7 +/- 5.6 microg/mL and 160.9 +/- 5.9 microg/mL , respectively), although the maximal inhibitory effect occurred at the same concentration (300 microg/mL ) in both cases. This action was shared by pulegone (30 - 300 microM), the principal component of the essential oil (IC (50) values of 21.8 +/- 2.1 microg/mL and 12.7 +/- 4.6 microg/mL , respectively). Nifedipine (30 nM - 30 microM) also abolished agonist-stimulated contractions, and was approximately twice and 12 times as potent as EOMP in inhibiting oxytocin- and prostaglandin F (2alpha) (PGF (2alpha))-stimulated contractions, respectively. In conclusion, our results show that the essential oil of the abortifaceant plant Mentha pulegium exerts an inhibitory effect on the contractile activity of the isolated rat myometrium. This oil shares a common effect with the voltage-dependent calcium channel (VDCC) blocker nifedipine, although ostensibly acting via a different mechanism. It thus appears that EOMP and pulegone do not exert direct toxic effects on the myometrium per se that would cause abortion, and other possibilities such as systemic metabolism of plant constituents may rather underlie the abusive use of Mentha pulegium in popular medicine.

Animals↗
PubMed2026

Comprehensive plastome variation and RNA editing in Mentha: insights into phylogenetic relationships and candidate DNA barcodes.

INTRODUCTION: Mentha is an economically and medicinally important genus in Lamiaceae, but its taxonomy and species delimitation remain challenging because of frequent hybridization, polyploidy, and marked morphological plasticity. METHODS: In this study, we comparatively analyzed 12 plastomes representing major Mentha species, hybrid taxa, and unresolved accessions, including four newly assembled genomes, to characterize plastome structure, repeat composition, sequence divergence, phylogenetic relationships, and plastid RNA editing. The M. arvensis plastome and RNA-seq datasets originated from independent Swiss and Indian accessions, respectively. RESULTS: The plastomes were highly conserved in overall organization, ranging from 151,824 to 152,154 bp and displaying the typical quadripartite structure. Gene content and order were largely stable across taxa, with only minor variation likely associated with annotation differences at IR/SC boundary regions. Codon usage analysis revealed a clear bias toward A/U-ending synonymous codons, and most shared protein-coding genes showed low Ka/Ks ratios, indicating predominant purifying selection. Repeat analyses showed that simple sequence repeats were mainly composed of A/T-rich mononucleotide motifs, whereas long repeats were concentrated in the 30-40 bp size class. Comparative analyses identified six hypervariable regions, namely ccsA-ndhD, ycf1, ndhD, rpl32-trnL-UAG, rbcL-accD, and petA-psbJ, which represent promising candidate plastid markers for species discrimination. Phylogenetic analysis based on complete plastomes provided strong support for relationships among the sampled taxa and recovered a close affinity among M. aquatica, M. arvensis, and M. canadensis. In addition, RNA-seq analysis of M. arvensis identified 17 candidate plastid RNA editing sites, most of which were C-to-U conversions and nonsynonymous events. DISCUSSION: Together, these results expand plastid genomic resources for Mentha and provide a useful framework for phylogenetic inference, species identification, and future germplasm utilization.

RNA editing↗
PubMed2004

Natural variability of the enantiomeric composition of bioactive chiral terpenes in Mentha piperita.

The variability of the enantiomeric distribution of biologically active chiral terpenes in Mentha piperita plants from different geographical origins was evaluated by solid phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS). The optimisation of some parameters (i.e. exposure temperature, extraction time and type of fibre) affecting SPME-extraction enabled relative standard deviations ranging from 4 to 13% to be achieved. The use of two different chiral stationary phases allowed to separate the identified chiral terpenes into their corresponding enantiomers as well as to verify the enantiomeric excesses of those compounds which were enantiomerically resolved on both phases. For all chiral terpenes, the enantiomeric composition varied within a very narrow range all over the samples. Consequently, it may be stated that the enantiomeric composition of chiral terpenes in Mentha piperita appears to be independent of the geographical origin of the plant and, thus, any alteration in the characteristic value may be related to an adulteration or inadequate sample handling. These results support the usefulness of the enantiomeric composition of bioactive chiral terpenes in Mentha piperita in authenticity studies.

Mentha piperita↗
PubMedDate not supplied

[Study on the antioxidant activity of Menthae longifoliae folium and effect of pesticide treatment with Topsin M on the antioxidant activity].

This study evaluated both the antioxidant activity of Menthae longifoliae folium and the influence of Topsin M (a pesticide which is widely used nowadays) upon the antioxidant activity of the drug. In this respect, there have been used leaves of Mentha longifolia (L.) Huds., both untreated and treated with Topsin M. The leaves were dried, powdered and extracted with aqueous methanol. Taking into account the fact that polyphenols, and especially flavonoids act as antioxidants, these compounds were quantified in the crude extracts. Both the capacity of inhibition of 15-lipoxygenase and the diphenylpicrylhydrazyl radical-scavenging capacity were also evaluated. The undergone study highlighted the fact that crude extracts of Menthae longifoliae folium had a good antioxidant activity; the extracts were active both as diphenylpicrylhydrazyl radical scavengers and as 15-lipoxygenase inhibitors. Treatment with Topsin M did not consistently influence the antioxidant activity of the drug.

Antioxidants↗
PubMed1993

Production and characterization of polyclonal antibodies in rabbits to 4S-limonene synthase from spearmint (Mentha spicata).

Limonene synthase, a monoterpene cyclase from the oil glands of spearmint (Mentha spicata) leaves that catalyzes the conversion of geranyl pyrophosphate to (-)-4S-limonene, was purified, and polyclonal antibodies were generated in rabbits against the sodium dodecyl sulfate-denatured protein. Immunoblotting analysis revealed that the antibodies were very specific for denatured limonene synthase from all Mentha species tested. However, no immunological cross-reactivity was observed with denatured limonene synthases from Valencia oranges (Citrus sinensis, Rutaceae) or wormseed (Chenopodium ambrosioides, Chenopodiaceae). Furthermore, the antibody preparation did not detectably cross-react with other monoterpene cyclases from related angiosperm species of the Lamiaceae, Asteraceae, and Umbellifereae, or from conifer species, and no cross-reactivity was demonstrated toward several sesquiterpene cyclases of higher plant and fungal origin. Although the antibody preparation was highly selective for denatured limonene cyclase from Mentha, the antibodies did not recognize the native protein in several different types of experiments. Nevertheless, specificity for the target enzyme was unambiguously demonstrated when the antibody preparation was shown to cross-react with the cyclase protein expressed in Escherichia coli that harbored the corresponding limonene synthase cDNA gene from M. spicata.

Animals↗
PubMed1999

Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.

Mentha x piperita shoot tips and first leaf pairs were fed with aqueous solutions of different deuterium-labeled pulegone and various enantiomeric distributions. The essential oil was extracted by solid-phase microextraction and analyzed using enantioselective multidimensional gas chromatography/mass spectrometry. The genuine p-menthan-3-ones (-)-menthone and (+)-isomenthone as well as their labeled analogues were analyzed simultaneously. Both enantiomers of labeled pulegone were converted into the corresponding labeled p-menthan-3-ones by Mentha x piperita, indicating an unspecific reduction process. The generation of 4S- and 4R-configured p-menthan-3-ones differed in their stereoselectivities. Labeled (S)-pulegone was reduced by Mentha x piperita more rapidly rather than (R)-pulegone. From a comparison of labeled pulegone enantiomers the bioconversion preferrably led to 4S-configured diastereomers.

Biotransformation↗
PubMed1976

Studies on the metabolism of d-limonene (p-mentha-1,8-diene). IV. Isolation and characterization of new metabolites and species differences in metabolism.

1. The main route of elimination of d-limonene administered orally was via the urine in animals and man, 75-95% of the administered radioactivity being excreted in the urine during 2-3 days. Faecal excretion accounted for less than 10% of the dose in animals during 2-3 days. 2. In addition to six metabolites, namely p-mentha-1,8-dien-10-ol (M-I), p-menth-1-ene-8,9-diol (M-II), perillic acid (M-III), perillic acid-8,9-diol (M-IV), p-mentha-1,8-dien-10-yl-beta-D-glucopyranosiduronic acid (M-V) and 8-hydroxy-p-meth-1-en-9-yl-beta-D-glucopyranosiduronic acid (M-VI) isolated from rabbit urine previously (Kodama et al., 1974), five new metabolites have been isolated from dog and rat urine, and which were characterized as 2-hydroxy-p-menth-8-en-7-oic acid (M-VII), perillylglycine (M-VIII), perillyl-beta-D-glucopyranosiduronic acid (M-IX), p-mentha-1,8-dien-6-ol (M-X) and probably p-menth-1-ene-6,8,9-triol (M-XI). 3. The major metabolite of d-limonene in the urine was M-IV in rat and rabbit, M-IX in hamster, M-II in dog and M-VI in guinea pig and man.

Animals↗
PubMed2002

Influence of the leaf extract of Mentha arvensis Linn. (mint) on the survival of mice exposed to different doses of gamma radiation.

BACKGROUND: The aim of the present study was to evaluate the radioprotective effect of Mentha arvensis (mint) on the survival of mice exposed to various doses of whole-body gamma radiation. MATERIAL AND METHODS: The radioprotective effect of various doses (0, 2.5, 5, 10, 20, 40 and 80 mg/kg body weight) of chloroform extract of mint (Mentha arvensis Linn.) was studied in mice exposed to 10 Gy gamma radiation. RESULTS: The 10 mg/kg of mint extract was found to afford best protection as evidenced by the highest number of survivors in this group at 30 days post-irradiation, and further experiments were carried out using this dose of mint extract. The mice treated with 10 mg/kg body weight mint extract or oil were exposed to 6, 7, 8, 9 and 10 Gy of gamma radiation and observed for the induction of radiation-sickness and mortality up to 30 days post-irradiation. The mint extract pretreatment was found to reduce the severity of symptoms of radiation sickness and mortality at all exposure doses and a significant increase in the animal survival was observed when compared with the oil + irradiation group. All of the animals that were treated with 10 mg/kg mint extract and then exposed to 7 Gy irradiation were protected against the radiation-induced mortality when compared with the concurrent oil + irradiation group, in which 20% animals died by 30 days post-irradiation. The mint extract treatment protected the mice against the gastrointestinal death as well as bone marrow deaths. The DRF was found to be 1.2. The drug was non-toxic up to a dose of 1,000 mg/kg body weight, the highest drug dose that could be tested for acute toxicity. CONCLUSION: From our study it is clear that mint extract provides protection against the radiation-induced sickness and mortality and the optimum protective dose of 10 mg/kg is safe from the point of drug-induced toxicity.

Animals↗
PubMed2003

Medicinal and aromatic plant materials as nitrification inhibitors for augmenting yield and nitrogen uptake of Japanese mint (Mentha arvensis L. Var. Piperascens).

Pot experiments were conducted to evaluate the relative performance of medicinal and aromatic plant materials and dicyandiamide (DCD) as nitrification inhibitors to regulate transformation of N from urea. Their effect on the efficiencies of use of N by Japanese mint (Mentha arvensis cv. Hy 77) was tested. Urea was coated with these materials viz., Mentha spicata, Artemisia annua or DCD at the rate of 5% (w/w) of fertilizer urea using an appropriate coating technique. Nimin (tetranortriterpenoids, an ethanol extract of neem (Azadirachta indica Juss) coating was done at the rate of 1% w/w of urea. Fertilizer nitrogen was applied at 100 and 200 mg kg(-1) soil. These natural coating materials significantly increased the herb and essential oil yields of the crop at both rates of fertilizer nitrogen compared to urea alone and were found to be as effective as DCD in retarding NO3- formation in soil. Herb yield increased by 6-81% when compared to uncoated urea. The increase in essential oil yield ranged between 3% and 68% due to coating. The effectiveness of the nitrification-inhibitor--coated urea, however, varied with the soils used and the rate of fertilizer nitrogen applied. The results suggest that the natural products could be potential nitrification inhibitors for increasing fertilizer N use efficiency.

Biological Availability↗
PubMed2004

Screening of free radical scavenging compounds in water extracts of Mentha samples using a postcolumn derivatization method.

An on-line high-performance liquid chromatography-1,1-diphenyl-2-picrylhydrazyl (HPLC-DPPH*) method has been improved for the detection of polar and nonpolar radical scavenging compounds in complex plant extracts. Nine water extracts were prepared from different Mentha species, varieties, hybrids, and cultivars. After the components within each extract had been separated by reverse phase chromatography using 10-100% methanol with 2% acetic acid as a mobile phase, analytes within the eluent capable of scavenging a citric acid-sodium citrate-buffered methanol 1,1-diphenyl-2-picrylhydrazyl solution were detected by postcolumn derivatization at 517 nm. The HPLC-DPPH* on-line method was applied to the qualitative and quantitative analysis of Mentha extracts. There was a strong correlation between the scavenging (negative) peak area and the concentration of the radical scavenging reference substances used. The minimum detectable concentration (microg/mL) of the antioxidant compounds was determined. Caffeic acid, eriocitrin (eriodictyol-7-O-rutinoside), luteolin-7-O-glucoside, and rosmarinic acid were identified as the dominant radical scavengers in these extracts by this method.

Antioxidants↗
PubMed2006

Changes in the enantiomeric distribution of selected volatile constituents of Mentha pulegium L. powders caused by hot water treatment.

The variation, in general, of the composition of the aromatic fraction and, in particular, of the enantiomeric composition of certain chiral volatile compounds of commercial Mentha pulegium L. powders caused by boiling water was evaluated. A comparison between the volatile profile of the studied herbs demonstrated that most M. pulegium L. samples contained high proportions of Mentha piperita L., even when this information was not specified on the label. Likewise, substantial changes in the volatile fraction of the infusions with respect to the composition of the original plant used in their preparation were found. The enantiomeric composition of some chiral compounds of the dried plant material, particularly limonene, was modified by adding hot water, whereas others were kept invariable. The results shown in this work reflect the need for the control of the composition of commercial powders and brews of M. pulegium L. to ensure their correct application.

Gas Chromatography-Mass Spectrometry↗