piperitenone and piperitone

The aerial parts of wild and cultivated Mentha mozaffarianii Jamzad were collected at full flowering stage from two provinces (Hormozgan and Fars) of Iran. The essential oils were extracted by a Clevenger approach and analysed using GC and GC-MS. The main components in wild plants were piperitenone (33.85%), piperitone (21.18%), linalool (6.89%), pulegone (5.93%), 1, 8.cineole (5.49%), piperitenone oxide (5.17%) and menthone (4.69%) and in cultivated plants, cis-piperitone epoxide (28.89%), linalool (15.36%), piperitone (11.57%), piperitenone oxide (10.14%), piperitenone (8.42%),1,8-cineole (3.60%) were the main constituents in essential oil. The in vitro antimicrobial activity of the essential oil of M. mozaffarianii was studied against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Candida albicans. The results of the bioassays showed that the oil exhibited high antimicrobial activity against all the tested pathogens.

Topics: Acyclic Monoterpenes; Anti-Infective Agents; Candida albicans; Cyclohexane Monoterpenes; Cyclohexanols; Eucalyptol; Gas Chromatography-Mass Spectrometry; Iran; Mentha; Menthol; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Plant Components, Aerial; Plants, Medicinal; Staphylococcus aureus

Essential oil (EO) extracts coming from two representative populations of Mentha suaveolens Ehrh. subesp. suaveolens in Eastern Iberian Peninsula were analyzed by gas chromatography coupled with mass spectrometry and flame ion detector. Plant sampling was carried out in the morning and evening in order to study diurnal variation in EO profiles. Likewise, leaves and inflorescences were analyzed separately. Two chemotypes corresponding to each one of the populations were identified, with piperitenone oxide (35.2 - 74.3%) and piperitone oxide (83.9 - 91.3%), respectively, as major compounds. Once different chemotypes were identified, canonical correspondence analysis was employed to evaluate the effect of the bioclimatic and edaphic factors recorded in each location on the observed differences. Statistical analysis suggested that these chemotypes were closely related to specific environmental factors, mainly the bioclimatic ones. Concretely, piperitenone oxide chemotype can be associated to supramediterranean bioclimatic conditions and soils with major salinity and water field capacity. On the other hand, the most volatile fraction (hydrocarbon monoterpenes) reached its higher level in the morning; specifically, a noticeable amount of limonene was found in morning samples of flowers (4.8 - 10.6%). This fact can be related to ecological role of volatile compounds in order to attract pollinator insects.

Topics: Climate; Cyclohexane Monoterpenes; Gas Chromatography-Mass Spectrometry; Mentha; Monoterpenes; Oils, Volatile; Oxides; Plant Leaves; Soil; Spain

Essential oils from Greek Mentha species showed different chemical compositions for two populations of M. pulegium, characterized by piperitone and pulegone. Mentha spicata essential oil was characterized by endocyclic piperitenone epoxide, piperitone epoxide, and carvone. The bioactivities of these essential oils and their components have been tested against insect pests (Leptinotarsa decemlineata, Spodoptera littoralis and Myzus persicae), root-knot nematodes (Meloydogine javanica) and plants (Lactuca sativa, Lolium perenne, Solanum lycopersicum). The structure-activity relationships of these compounds have been studied including semi-synthetic endocyclic trans-carvone epoxide, exocyclic carvone epoxide, a new exocyclic piperitenone epoxide and trans-pulegone epoxide. Leptinotarsa decemlineata feeding was affected by piperitenone and piperitone epoxide. Spodoptera littoralis was affected by piperitone epoxide and pulegone. The strongest nematicidal agent was piperitenone epoxide, followed by piperitone epoxide, piperitenone and carvone. Germination of S. lycopersicum and L. perenne was significantly affected by piperitenone epoxide. This compound and carvone epoxide inhibited L. perenne root and leaf growth. Piperitenone epoxide also inhibited the root growth of S. lycopersicum. The presence of a C(1) epoxide resulted in strong antifeedant, nematicidal and phytotoxic compounds regardless of the C(4) substituent. New natural crop protectants could be developed through appropriate structural modifications in the p-menthane skeleton.

Topics: Animals; Cyclohexane Monoterpenes; Epoxy Compounds; Gas Chromatography-Mass Spectrometry; Germination; Mentha; Monoterpenes; Oils, Volatile; Plant Leaves; Plant Roots; Solanum lycopersicum; Spodoptera; Structure-Activity Relationship

Phytochemical analysis of the rhizome extract of Curcuma ecalcarata, a hitherto uninvestigated south Western Ghats endemic species, resulted in the isolation and identification of the diaryl heptanoid trans, trans-1,7-diphenyl-5-hydroxy-4,6-heptadiene-3-one (1), steroid β-sitosterol (2), flavanone pinocembrin (4) and monoterpenoids piperitenone (3) and 8-hydroxy piperitone (5). HPTLC estimation of pinocembrin in the rhizome revealed the plant as a rich source of pinocembrin (0.37% dry wt.). The rhizome essential oil was isolated by hydrodistillation and analysed by GC-FID, GC-MS and (13)C NMR. Among the 30 constituents identified in the oil, monoterpenoids predominated (94.2%) followed by sesquiterpenoids (5.8%). The major compound consisting of 65.2% of the oil was isolated and identified as piperitenone (3). The study highlights the plant as a rich source of the flavanone pinocembrin and the volatile aroma compound piperitenone.

Topics: Curcuma; Cyclohexane Monoterpenes; Flavanones; Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Molecular Structure; Monoterpenes; Oils, Volatile; Plant Extracts; Plant Oils; Rhizome; Sitosterols; Volatile Organic Compounds

The essential oil of 46 spontaneous plants of Calamintha nepeta (L.) Savi subsp. nepeta growing wild in Sud, Italy (Salento, Apulia), were investigated by GC/MS. Fifty-seven components were identified in the oil representing over the 98% of the total oil composition. Four chemotypes were identified: piperitone oxide, piperitenone oxide, piperitone-menthone and pulegone.

Topics: Cyclohexane Monoterpenes; Gas Chromatography-Mass Spectrometry; Italy; Monoterpenes; Nepeta; Oils, Volatile

Calamintha glandulosa (Req.) Bentham is an aromatic perennial plant belonging to the family Lamiaceae, mostly found on rocky pastures, dry meadows, and abandoned places of the Mediterranean area. Plants belonging to this genus are known as highly aromatic and to possess significant antimicrobial and antifungal properties. The aim of this study was to provide clear picture of the volatiles of this plant species, and, for the first time, to present C. glandulosa from Croatia in terms of its antioxidant activity.. The essential oil and headspace obtained from odorous parts of C. glandulosa were subjected to capillary gas chromatography-mass spectrometry analysis. More than 50 volatile compounds were identified in six samples obtained using different extraction techniques. The most abundant components in all the samples examined were oxygenated monoterpenes, with piperitone (19.9-59.5%) and piperitenone (7.1-42.6%) as the main representatives. The total phenolic content of extracts obtained by successive Soxhlet extraction was measured, and the scavenging potency of the samples, indicated as IC50 values, were examined using four different spectrophotometric and spectrofluorimetric methods. In all cases the essential oil showed the lowest antioxidant activity, while the aqueous extract showed the highest. This can be explained by the levels of the phenolic compounds in the samples examined.. A clear picture of aroma profile of C. glandulosa is presented, and the results obtained differ from those published previously. The high antioxidant potential of C. glandulosa from Croatia was established for the first time. Results from the present study suggest further analysis on this plant species in order to define its medicinal properties.

Topics: Antioxidants; Croatia; Cyclohexane Monoterpenes; Inhibitory Concentration 50; Lamiaceae; Monoterpenes; Odorants; Oils, Volatile; Phenols; Plant Extracts

Populations of Mentha longifolia, an endangered species in Israel, were tested for essential oil composition and conservational ability. In 2002-2003, 25 wild populations country-wide were tested, indicating population divergence into two chemotypes. Chemotype A was characterized by high levels of menthone and pulegone, and chemotype B by high levels of piperitenone oxide and piperitone oxide. Chemotype A was more abundant (22 of 25 populations) than chemotype B (11 of 25 populations). However, a chemotype/population interaction was not recorded (P > 0.05). In spring 2003, seven of the 25 wild populations were resampled, propagated, and cultivated at the Newe Ya'ar campus. Then, in 2004, the propagated plants were tested for essential oil composition. The propagated plants maintained the essential oil composition as well as the chemotype-frequency distribution of the original wild population from which they were obtained. Since a chemotype/population interaction was not recorded, and the cultivated plants displayed the wild population essential oil composition, it can be concluded that i) the chemotype diversity is genetically based, and ii) the M. longifolia populations sampled can be horticulturally conserved.

Topics: Cyclohexane Monoterpenes; Israel; Mentha; Menthol; Monoterpenes; Oils, Volatile

The aim of this study was to evaluate the activity of essential oil from Tagetes erecta against 3rd instars of Aedes aegypti and to determine the amounts of larvicidal thiophenes in all plant tissues. The oil obtained by steam distillation and analyzed by gas chromatography/mass spectrometry showed 14 compounds. The main compounds were piperitone (45.72%), D-limonene (9.67%), and piperitenone (5.89%). The essential oil was active against larvae of Ae. aegypti, with LC50 of 79.78 microg/ml and LC90 of 100.84 microg/ml. The larvicidal thiophene contents were higher in the roots and flowers as demonstrated by high-performance liquid chromatography analysis. Thus, T. erecta constitutes a good source of varied compounds showing larvicidal activity against Ae. aegypti.

Topics: Aedes; Animals; Cyclohexane Monoterpenes; Cyclohexenes; Gas Chromatography-Mass Spectrometry; Insecticides; Larva; Lethal Dose 50; Limonene; Monoterpenes; Mosquito Control; Oils, Volatile; Plant Oils; Tagetes; Terpenes

The flowering aerial parts of Mentha pulegium L. (Labiatae) has been traditionally used for its antiseptic properties for treatment of infectious diseases.. In order to validate its antiseptic properties with respect to traditional uses, we have screened the antimicrobial activity of flowering aerial parts of Mentha pulegium L. essential oil against different microorganisms.. This oil was obtained using hydrodistillation method and analyzed by GC and GC/MS. The antimicrobial activity was achieved using disc diffusion method and microbroth dilution assay.. Analysis of the essential oil revealed the presence of piperitone (38.0%), piperitenone (33.0%), alpha-terpineol (4.7%), and pulegone (2.3%) as the major components. The results showed a significant activity against microorganisms especially Gram-positive bacteria with inhibition zones and minimal inhibitory concentration values in the range of 8-21 mm and 0.25-4 microl/ml, respectively, whereas the least susceptible were Gram-negative bacteria especially Escherichia coli.. This investigation showed that the oil of Mentha pulegium L. has a potent antimicrobial activity and the Iranian Mentha pulegium L. oil belongs to piperitone/piperitenone type. Further research is required to evaluate the practical values of therapeutic applications.

Topics: Anti-Infective Agents; Chromatography, Gas; Cyclohexane Monoterpenes; Gas Chromatography-Mass Spectrometry; Iran; Medicine, Traditional; Mentha pulegium; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Plant Components, Aerial

Topics: Cyclohexane Monoterpenes; Ketones; Monoterpenes