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PubMed2001

Isoprenoid biosynthesis. Metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis.

Two independent pathways operate in plants for the synthesis of isopentenyl diphosphate and dimethylallyl diphosphate, the central intermediates in the biosynthesis of all isoprenoids. The mevalonate pathway is present in the cytosol, whereas the recently discovered mevalonate-independent pathway is localized to plastids. We have used isolated peppermint (Mentha piperita) oil gland secretory cells as an experimental model system to study the effects of the herbicides fosmidomycin, phosphonothrixin, methyl viologen, benzyl viologen, clomazone, 2-(dimethylamino)ethyl diphosphate, alendronate, and pamidronate on the pools of metabolites related to monoterpene biosynthesis via the mevalonate-independent pathway. A newly developed isolation protocol for polar metabolites together with an improved separation and detection method based on liquid chromatography-mass spectrometry have allowed assessment of the enzyme targets for a number of these herbicides.

Binding Sites↗
PubMed1967

Effects of light and temperature on the monoterpenes of peppermint.

Peppermint (Mentha piperita L.) was grown in a growth chamber under several combinations of temperature and illumination, and the monoterpenes of each leaf pair were analyzed by gas chromatography. Effects on the monoterpenes could be seen in the new leaves after a few days in the growth chamber. Long-day conditions enhanced growth, with a corresponding increase in the total amount of monoterpenes. Either short nights or cool nights, combined with full light intensity during the day, enhanced the formation of menthone and depressed the accumulation of menthofuran and pulegone. Experiments with interrupted night and with low light intensity indicated that photoperiod, as such, does not directly influence the terpene composition. It is suggested that the oxidation-reduction level of the monoterpenes reflects the oxidation-reduction state of the respiratory coenzymes of the terpene-producing cells, and that this, in turn, depends on the concentrations of respiratory substrates in the cells. This suggestion is based on the likelihood that warm nights cause depletion of respiratory substrates, resulting in oxidizing conditions, while cool nights preserve high levels of respiratory substrates, and thus maintain reducing conditions.

Journal Article↗
PubMed1984

Metabolism of Monoterpenes : Early Steps in the Metabolism of d-Neomenthyl-beta-d-Glucoside in Peppermint (Mentha piperita) Rhizomes.

Previous studies have shown that the monoterpene ketone l-[G-(3)H] menthone is reduced to the epimeric alcohols l-menthol and d-neomenthol in leaves of flowering peppermint (Mentha piperita L.), and that a portion of the menthol is converted to menthyl acetate while the bulk of the neomenthol is transformed to neomenthyl-beta-d-glucoside which is then transported to the rhizome (Croteau, Martinkus 1979 Plant Physiol 64: 169-175). Analysis of the disposition of l-[G-(3)H]menthone applied to midstem leaves of intact flowering plants allowed the kinetics of synthesis and transport of the monoterpenyl glucoside to be determined, and gave strong indication that the glucoside was subsequently metabolized in the rhizome. Studies with d-[G-(3)H]neomenthyl-beta-d-glucoside as substrate, using excised rhizomes or rhizome segments, confirmed the hydrolysis of the glucoside as an early step in metabolism at this site, and revealed that the terpenoid moiety was further converted to a series of ether-soluble, methanol-soluble, and water-soluble products. Studies with d-[G-(3)H]neomenthol as the substrate, using excised rhizomes, showed the subsequent metabolic steps to involve oxidation of the alcohol back to menthone, followed by an unusual lactonization reaction in which oxygen is inserted between the carbonyl carbon and the carbon bearing the isopropyl group, to afford 3,4-menthone lactone. The conversion of menthone to the lactone, and of the lactone to more polar products, were confirmed in vivo using l-[G-(3)H]menthone and l-[G-(3)H]-3,4-menthone lactone as substrates. Additional oxidation products were formed in vivo via the desaturation of labeled neomenthol and/or menthone, but none of these transformations appeared to lead to ring opening of the p-menthane skeleton. Each step in the main reaction sequence, from hydrolysis of neomenthyl glucoside to lactonization of menthone, was demonstrated in cell-free extracts from the rhizomes of flowering mint plants. The lactonization step is of particular significance in providing a means of cleaving the p-menthane ring to afford an acyclic carbon skeleton that can be further degraded by modifications of the well-known beta-oxidation sequence.

Journal Article↗
PubMed1985

Metabolism of Monoterpenes : Evidence for the Function of Monoterpene Catabolism in Peppermint (Mentha piperita) Rhizomes.

l-Menthone of peppermint leaves is reduced to d-neomenthol which is glucosylated and transported to the rhizome, whereupon the beta-d-glucoside is hydrolyzed, the aglycone oxidized back to l-menthone, and this ketone converted to l-3,4-menthone lactone. l-[G-(3)H]-3,4-Menthone lactone and its labeled progenitors, when incubated with excised mint rhizomes, gave rise to nonvolatile lipids as well as polar metabolites. The lipids thus generated consisted of labeled squalene and phytosterols in the nonsaponifiable fraction and C(14)-C(26) fatty acids in the saponifiable fraction. These results imply degradation of the terpenoid to acetylcoenzyme A and reduced pyridine nucleotide, and reincorporation of label via these products. Starch and soluble carbohydrates were also found to be labeled; however, chemical degradation of the [(3)H]glucose obtained on hydrolysis of starch indicated the presence of tritium only on interior carbons, suggesting that labeling had occurred via reduced pyridine nucleotides. Analysis of the labeled organic acids revealed the presence of several hydroxy methylacyl intermediates suggesting the operation of a modified beta-oxidation pathway in the degradation of the acyclic terpenoid skeleton. The results indicate that monoterpenes transported to the rhizome are oxidized to yield acetyl-coenzyme A and reduced pyridine nucleotides, and suggest that metabolic turnover of monoterpenes in mint represents a mechanism for recycling carbon and energy from foliar terpenes into other metabolites of the rhizome.

Journal Article↗
PubMed1991

Biochemical characterization of a spearmint mutant that resembles peppermint in monoterpene content.

A radiation-induced mutant of Scotch spearmint (Mentha x gracilis) was shown to produce an essential oil containing principally C3-oxygenated p-menthane monoterpenes that are typical of peppermint, instead of the C6-oxygenated monoterpene family characteristic of spearmint. In vitro measurement of all of the enzymes responsible for the production of both the C3-oxygenated and C6-oxygenated families of monoterpenes from the common precursor (-)-limonene indicated that a virtually identical complement of enzymes was present in wild type and mutant, with the exception of the microsomal, cytochrome P-450-dependent (-)-limonene hydroxylase; the C6-hydroxylase producing (-)-trans-carveol in the wild type had been replaced by a C3-hydroxylase producing (-)-trans-isopiperitenol in the mutant. Additionally, the mutant, but not the wild type, could carry out the cytochrome P-450-dependent epoxidation of the alpha,beta-unsaturated bond of the ketones formed via C3-hydroxylation. Although present in the wild type, the enzymes of the C3-pathway that convert trans-isopiperitenol to menthol isomers are synthetically inactive because of the absence of the key C3-oxygenated intermediate generated by hydroxylation of limonene. These results, which clarify the origins of the C3- and C6-oxygenation patterns, also allow correction of a number of earlier biogenetic proposals for the formation of monoterpenes in Mentha.

Journal Article↗
PubMed2006

Oral peppermint oil is a useful antispasmodic for double-contrast barium meal examination.

BACKGROUND AND AIM: Intraluminally administered peppermint oil (PO) is reportedly a safe and useful antispasmodic for gastroscopy, colonoscopy and double-contrast barium enema. The aim of this study was to examine the efficacy of oral PO for double-contrast barium meal examination (DCBM) without other antispasmodics. METHODS: Two hundred and five randomly chosen subjects (PO group) and 215 sex- and age-matched controls were enrolled. All participants underwent DCBM. The PO group was orally administered PO and a barium suspension mixture at the start of DCBM. Radiographs were blindly evaluated for spasm and overlapping with barium-filled duodenal loops (scored 0-3, indicating none to severe). The quality of barium coating of the mucosa and overall diagnostic quality (scored 0-3, indicating not acceptable to excellent) were also evaluated. RESULTS: There was no significant difference in subject acceptance between PO group and controls, and no adverse effects in either group. Scores for spasm at the esophagus, lower stomach and duodenal bulb were significantly lower in the PO than in the control group (P < 0.001). Scores for overlapping at the lower stomach and duodenal bulb were significantly lower in the PO than in the control group (P < 0.05, P < 0.01, respectively). Scores for overall diagnostic quality at the esophagus, lower stomach and duodenal bulb were significantly higher in the PO than in the control group (P < 0.001). Oral PO reduces spasm of the esophagus, lower stomach and duodenal bulb, inhibits barium flow to the distal duodenum, and improves diagnostic quality without other antispasmodics. CONCLUSIONS: Oral PO is a safe, easy to use and effective antispasmodic for DCBM.

Administration, Oral↗
PubMed1977

Turpentine-induced hypersensitivity to peppermint oil.

After a dental operation a former laboratory technician was referred to our clinic because of swelling of his tongue, lips, and gingival mucosa. Patch testing with the ICDRG standard test battery gave positive reactions to colophony, balsam of Peru, and turpentine peroxides. Further patch testing revealed hypersensitivity to peppermint oil (an ingredient of several dental preparations) due to the sensitizing properties of three ingredients: alpha-pinene, limonene, and phellandrene. These compounds also occur in turpentine oil, a substance used in the patient's laboratory.

Aged↗
PubMed2002

The treatment of small intestinal bacterial overgrowth with enteric-coated peppermint oil: a case report.

Recent investigations have shown that bacterial overgrowth of the small intestine is associated with a number of functional somatic disorders, including irritable bowel syndrome (IBS), fibromyalgia, and chronic fatigue syndrome. A number of controlled studies have shown that enteric-coated peppermint oil (ECPO) is of benefit in the treatment of IBS. However, despite evidence of strong antimicrobial activity, ECPO has not been specifically investigated for an effect on small intestinal bacterial overgrowth (SIBO). A case report of a patient with SIBO who showed marked subjective improvement in IBS-like symptoms and significant reductions in hydrogen production after treatment with ECPO is presented. While further investigation is necessary, the results in this case suggest one of the mechanisms by which ECPO improves IBS symptoms is antimicrobial activity in the small intestine.

Adult↗
PubMed1992

Purification of 4S-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita) and spearmint (Mentha spicata).

The p-menthane monoterpenes of the Mentha species are biosynthesized from geranyl pyrophosphate via the monocyclic olefin 4S-limonene. A monoterpene cyclase was isolated from both Mentha x piperita (peppermint) and Mentha spicata (spearmint) that catalyzes the cyclization of geranyl pyrophosphate to 4S-limonene. This enzyme, 4S-limonene synthase, was purified to apparent homogeneity by dye ligand, anion exchange, and hydrophobic interaction chromatography. Since the monoterpenes of Mentha are synthesized and secreted in modified epidermal hairs called glandular trichomes, an extract of isolated glandular trichome cells was used as the source of this enzyme. A combination of gel permeation chromatography and sodium dodecyl sulfate-polyacrylamide gel electrophoresis showed that purified 4S-limonene synthase had a native molecular weight of 56,000 and was monomeric. The principal product of the enzyme was enantiomerically pure (-)-4S-limonene, and a catalytic constant of 0.3/s was determined. The basic properties of 4S-limonene synthase from both M. x piperita and M. spicata are identical and, in general, are similar to those of other monoterpene, sesquiterpene, and diterpene cyclases isolated from microorganisms and higher plants.

Chromatography, Liquid↗
PubMed2006

[Use of essential oil of peppermint (Mentha piperita) in the complex treatment of patients with infiltrative pulmonary tuberculosis].

The paper describes the effects of peppermint (Mentha piperita) essential oil inhaled by patients with infiltrative pulmonary tuberculosis in the penitentiary system. This procedure is shown to be most effective in infiltrative pulmonary tuberculosis in the phase of resorption of infiltrates and/or closure of decay cavities. The efficiency is determined by the rapid positive changes in a tuberculous process, which appear as a rapider regression of tuberculous inflammation, causing small residual changes. This procedure may be used to prevent recurrences and exacerbations of pulmonary tuberculosis.

Administration, Inhalation↗
PubMedDate not supplied

Extraction of light filth from whole peppermint leaves: collaborative study.

Results are reported for a collaborative study of a method for the extraction of light filth from whole peppermint leaves. A 5 g sample is defatted with isopropanol in a simple reflux appartus. Rat hairs, insect fragments, and whole insects are isolated by wet sieving on a No. 230 sieve, a deaerating boil in 40% isopropanol solution, flotation with Tween 80-Na4EDTA (1 + 1) and mineral oil-heptane (85 + 15), and trappings in a Wildman trap flask. Average recoveries obtained by 6 collaborators for 3 spike levels of rat hairs (5, 10, 15) were 83.3, 87.5, and 82.2%, respectively. For whole insects (5, 10, 15) recoveries averaged 85.0, 80.0 and 77.2% respectively; for insect fragments (20, 30, 50) recoveries averaged 79.6, 88.3, and 84.8%, respectively. The average recoveries for the 3 levels of each analyte were not significantly different. The method has been adopted official first action.

Animals↗