RESUMEN

Clinopodium mexicanum (CM) has been used by the population as a home remedy for inducing sleep, and as a sedative and analgesic. This study presents the first evaluation of the antioxidant activity of the essential oil (EO) obtained through hydrodistillation of the aerial parts of CM. NaCl, CaCl2, and Tween 20 were used as additives and the yield, chemical composition, and toxicity of the EO were evaluated. The findings revealed that the highest yield of EO was obtained through hydrodistillation without additives, and the additives significantly influenced the antioxidant activity of the EO. The main components of the EO were found to be pulegone and menthone. The toxicity of the EO was determined using the brine shrimp assay, with an LD50 of 32 mg/L. Based on these results, the authors suggest that the Clinopodium mexicanum EO has the potential to serve as a natural antioxidant.

RESUMEN

ETHNOPHARMACOLOGY RELEVANCE: Agastache mexicana is a popular plant of great demand in folk medicine, essentially due to its calming properties and for alleviating arthritic, muscular and abdominal pain. Despite its spectrum for pain relief, pharmacological studies of its bioactive constituents have been barely investigated. AIM OF THE STUDY: To evaluate protective properties of the A. mexicana and bioactive compounds improving pathological gastrointestinal conditions in rodents. MATERIAL AND METHODS: Different doses of the essential oil of A. mexicana ssp. mexicana and ssp. xolocotziana (30-562.2 mg/kg, i.p.) and individual monoterpenes (3-300 mg/kg, i.p.) were evaluated in an abdominal pain model. The most active monoterpene limonene and sulfasalazine (reference drug, 100 mg/kg, p.o.) were also evaluated in the oxazolone-induced colitis model using an oral gavage, where some inflammatory cytokines were analyzed by enzyme-linked immunosorbent assays. Finally, colonic histological assessment and gastroprotection in the absolute ethanol-induced ulcer model were explored. RESULTS: Our results demonstrated that the essential oil of both subspecies produced a significant reduction in the abdominal writhes, where monoterpenes limonene and pulegone were partially responsible bioactive metabolites. Limonene showed the major antinociceptive efficacy in the writhing test. It also significantly decreased hyperalgesia, pathological biomarkers, and colonic inflammatory cytokines in the oxazolone-induced colitis model, as well as prevention in gastric damage. CONCLUSIONS: Present results provide scientific evidence to reinforce the use of A. mexicana in the traditional medicine for gastrointestinal conditions, mainly related to pain and inflammation, demonstrating the potential of monoterpenes as natural products in the therapeutics of gastrointestinal affections such as ulcer, colitis, and abdominal pain.

Asunto(s)

Agastache/química , Analgésicos/farmacología , Monoterpenos/farmacología , Aceites Volátiles/farmacología , Analgésicos/química , Analgésicos/aislamiento & purificación , Animales , Colitis Ulcerosa/tratamiento farmacológico , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Fármacos Gastrointestinales/administración & dosificación , Fármacos Gastrointestinales/aislamiento & purificación , Fármacos Gastrointestinales/farmacología , Limoneno/administración & dosificación , Limoneno/aislamiento & purificación , Limoneno/farmacología , Masculino , Ratones , Ratones Endogámicos BALB C , Monoterpenos/química , Monoterpenos/aislamiento & purificación , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Dolor/tratamiento farmacológico , Ratas , Ratas Wistar , Sulfasalazina/farmacología

RESUMEN

The insecticidal activity of Mentha oil and its main components has been tested and established for various insects/pests. Several mint ketones have demonstrated to act on GABAA receptors (GABAA-R), a transmembrane channel target of several important insecticides whose activity can be modulated by surface-active compounds and by changes in the physical properties of the lipid membrane. In the present work, we analyze the capacity of monoterpenic ketones most commonly found in Mentha species, pulegone and menthone, to interact with DPPC membranes by molecular dynamics (MD) simulations and Langmuir monolayers. The experimental results indicate that the presence of menthone and pulegone in the subphase modify the interfacial characteristics of DPPC isotherms. The changes were reflected as expansion of the isotherms and disappearance or bringing forward of DPPC phase transition. MD simulation corroborate these results and indicate that both ketones are located at the region of the carbonyl group, at the interface with the acyl chains. Ketone intercalation between lipid molecules would induce an increasing intermolecular interaction, diminishing the film elasticity and causing an ordering effect. Our results suggest that the insecticidal activity of both ketones could involve their interaction with lipid molecules causing disturbance of the cell membrane as postulated for several larvicide compounds, or at least modulating the receptor surrounding.

Asunto(s)

Fenómenos Biofísicos/efectos de los fármacos , Membrana Celular/efectos de los fármacos , Membrana Celular/metabolismo , Insecticidas/farmacología , Cetonas/farmacología , Conformación Molecular , Simulación de Dinámica Molecular

RESUMEN

ETHNOBOTANICAL AND ETHNOMEDICINAL RELEVANCE: In southern Ecuador, horchata lojana is a popular aromatic and refreshing beverage that is prepared from an aqueous infusion of different mixtures of local medicinal and aromatic plants. The drink is considered a traditional anti-inflammatory agent and brain tonic; due these properties, it has been drunk since Colonial Times. Several pharmacological studies have evaluated the effects of horchata aqueous infusion. However, the aromatic profile and the contribution of the volatile components to the biological activity of the drink have not been investigated so far. For these reasons, we have determined the chemical composition of the essential oils (EOs) distilled from five mixtures of aromatic plants commonly used for the preparation of this traditional drink. Moreover, to support the curative properties of the aromatic plants, the anticholinesterase activity of the EOs was examined. MATERIAL AND METHODS: Different bunches of fresh mixed medicinal and aromatic plants, called tongos, are sold at local markets in the province of Loja for the preparation of different types of horchata. In this research we have purchased plant bunches sold at five popular markets of Loja province. Subsequently, aromatic plants in each bunch were separated from medicinal plants and were then hydrodistilled to give the corresponding EOs. Subsequently, the chemical composition of each EO was determined by GC-MS/GC-FID techniques, whereas the cholinesterase inhibitory activity in vitro was determined against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. AIMS OF THE STUDY: i) to contribute to the chemical and pharmacological study of the aroma components of the traditional Ecuadorian drink horchata lojana; ii) to identify botanically the mixtures of aromatic plants used to make the drink; iii) to establish, on the basis of the chemical composition of the EOs, the compounds mainly responsible for the characteristic beverage flavor; iv) to establish the possible existence of an aromatic pattern characteristic of each horchata preparation; v) to test the anticholinesterase activity of the EOs against AChE and BuChE in order to support the traditional consume of the drink as an effective brain tonic. RESULTS: A total of 23 botanical families and 32 species of plants used for the preparation of five different variants of the traditional horchata lojana beverage, have been identified. Fourteen aromatic species were determined to be responsible for the characteristic flavor of the drink. All the analyzed EOs belong to the monoterpene type. A total of 88 compounds have been identified in the different EOs, twenty-four of which are common components of the oils. CONCLUSIONS: According to the main components of the EOs distilled from the five groups of horchata lojana plants, four aromatic profiles have been defined: (i) neral + geranial + carvone, (ii) neral + geranial + myrcene; (iii) geranial + methyl eugenol + isomenthone + neral + citronellol; (iv) (E)-anethole + geranial + pulegone. Moreover, according to the literature, several aromatic plants and individual EOs components exhibit a wide range of biological activities. This finding as well as the significant BuChE inhibitory activity exhibited in vitro by the EOs give scientific support to the use of identified aromatic plants in the traditional preparation of horchata, that is considered a natural analgesic and anti-inflammatory remedy, and an effective brain tonic.

Asunto(s)

Bebidas , Butirilcolinesterasa/metabolismo , Inhibidores de la Colinesterasa/química , Aceites Volátiles/química , Plantas Medicinales , Inhibidores de la Colinesterasa/aislamiento & purificación , Inhibidores de la Colinesterasa/farmacología , Ecuador , Activación Enzimática/efectos de los fármacos , Activación Enzimática/fisiología , Cromatografía de Gases y Espectrometría de Masas/métodos , Humanos , Aceites Volátiles/aislamiento & purificación , Aceites Volátiles/farmacología , Hojas de la Planta

RESUMEN

The Cunila angustifolia essential oil was obtained from fresh leaves by hydrodistillation and analyzed by GC-FID and GC-MS to determine its chemical composition. The essential oil presented pulegone (29.5 %) and isomenthol (27.0 %) as major components, and other compounds such as menthone (8.6 %), neomenthol (7.2 %), menthyl acetate (2.5 %) and caryophyllene oxide (2.0 %) were identified. The cytotoxic activity of the essential oil was evaluated by MTS assay, with the human cancer cell lines of the lung (A549), breast (MCF-7) and skin melanoma (SK-Mel-28). The assay showed the highest selectivity, to MCF-7 cell lines, with IC50 equal to 34.0 µg mL-1 , low selectivity for SK-Mel-28 cell lines, with IC50 equal to 279.9 µg mL-1 , and no mortality to A549 cell lines.

Asunto(s)

Lamiaceae/química , Aceites Volátiles/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Cromatografía de Gases y Espectrometría de Masas , Humanos , Lamiaceae/metabolismo , Aceites Volátiles/análisis , Aceites Volátiles/farmacología , Hojas de la Planta/química , Hojas de la Planta/metabolismo

RESUMEN

The effects of plant inoculation with plant growth-promoting rhizobacteria (PGPR) and those resulting from the exogenous application of salicylic acid (SA) or methyl jasmonte (MeJA) on total phenolic content (TPC) and monoterpenes in Mentha x piperita plants were investigated. Although the PGPR inoculation response has been studied for many plant species, the combination of PGPR and exogenous phytohormones has not been investigated in aromatic plant species. The exogenous application of SA produced an increase in TPC that, in general, was of a similar level when applied alone as when combined with PGPR. This increase in TPC was correlated with an increase in the activity of the enzyme phenylalanine ammonia lyase (PAL). Also, the application of MeJA at different concentrations in combination with inoculation with PGPR produced an increase in TPC, which was more relevant at 4 mM, with a synergism effect being observed. With respect to the main monoterpene concentrations present in peppermint essential oil (EO), it was observed that SA or MeJA application produced a significant increase similar to that of the combination with rhizobacteria. However, when plants were exposed to 2 mM MeJA and inoculated, an important increase was produced in the concentration on menthol, pulegone, linalool, limonene, and menthone concentrations. Rhizobacteria inoculation, the treatment with SA and MeJA, and the combination of both were found to affect the amount of the main monoterpenes present in the EO of M. piperita. For this reason, the expressions of genes related to the biosynthesis of monoterpene were evaluated, with this expression being positively affected by MeJA application and PGPR inoculation, but was not modified by SA application. Our results demonstrate that MeJA or SA application combined with inoculation with PGPR constitutes an advantageous management practice for improving the production of secondary metabolites from M. piperita.

Asunto(s)

Mentha piperita/crecimiento & desarrollo , Monoterpenos/análisis , Fenoles/análisis , Reguladores del Crecimiento de las Plantas/farmacología , Rhizobiaceae/fisiología , Acetatos/farmacología , Ciclopentanos/farmacología , Sinergismo Farmacológico , Regulación del Desarrollo de la Expresión Génica/efectos de los fármacos , Regulación de la Expresión Génica de las Plantas/efectos de los fármacos , Mentha piperita/química , Mentha piperita/microbiología , Oxilipinas/farmacología , Fenilanina Amoníaco-Liasa/metabolismo , Extractos Vegetales/análisis , Proteínas de Plantas/metabolismo , Ácido Salicílico/farmacología , Metabolismo Secundario/efectos de los fármacos

RESUMEN

Essential oils, which are mixtures of terpenes, frequently show stronger insecticide activity, i.e., lower lethal dose 50 (LC50), than their most abundant terpenes. Synergy between terpenes provides a plausible explanation, but its demonstration has been elusive. In the present work, we look for an alternative explanation, by considering the influence of insect metabolic detoxification. Basically, we propose a model (metabolic model, MM) in which the LC50 of the major terpene in a mixture is expected to include a fraction that is detoxified by the insect, whereas a minor terpene would act unimpeded, showing a lower LC50 than when acting alone. In order to test this idea, we analyzed the effects of inhibiting the cytochrome P450 detoxification system with piperonyl butoxide (PBO), on the lethal concentration of terpenes as fumigants against Musca domestica. We found that, within a group of 10 terpenes [linalool, citronellal, (R)-α-pinene, 1,8-cineole, γ-terpinene, limonene, α-terpinene, (S)-ß-pinene, thymol and (R)-pulegone], seven showed the LC50PBO (the lethal concentration for PBO-treated flies) between 1.7 and 12.4 times lower than the corresponding LC50 when P450 was not inhibited. Only in one case, that of (R)-pulegone, was the LC50PBO greater than the LC50, while two terpenes [(S)-ß-pinene and thymol] showed no changes in toxicity. The increased activity of most terpenes (particularly linalool and citronellal) in PBO-treated flies supports our hypothesis that normally the LC50 includes a fraction of inactive compound, due to detoxification. Having previously determined that M. domestica preferentially oxidizes the most abundant terpene in a mixture, while terpenes in smaller proportions are poorly or not detoxified by the P450 system, we assessed whether the toxicity of minority terpenes in a mixture is similar to their activity under P450 inhibition. We chose suitable binary combinations in such a way that one terpene (in greater proportion) should be the target of P450 while the other (in smaller proportion) should intoxicate the fly with LC50PBO or similar. Combinations of 1,8-cineole-citronellal, 1,8-cineole-linalool, linalool-citronellal, (R)-pulegone-linalool, (R)-pulegone-1,8-cineole and (R)-pulegone-citronellal were assayed against M. domestica, and the LC50 of each mixture was determined and compared to values predicted by MM (considering the LC50PBO for minor component) or by the classical approach (LC50 for both components). The MM showed the best fit to the data, suggesting additive rather than synergistic effects, except for the combination of (R)-pulegone-citronellal that was clearly synergistic. Thus, the experimental data indicate that the insect preferentially oxidizes the major component in a mixture, while the terpene in lesser proportion acts as a toxicant, with higher toxicity than when it was assayed alone. These findings contribute to a deeper understanding of the higher toxicity of essential oils compared to their component terpenes and provide important information for the design of effective insecticides based on essential oils or terpenes.

RESUMEN

Clinopodium gilliesii (Benth.) Kuntze, harvested in the Chilean highlands, contains a surprising 93.87% of the toxic monoterpene pulegone in the essential oil. These results show remarkable differences with studies of the same species carried out in Argentina and Peru. These dissimilarities in the monoterpene composition of essential oils should be associated with differences in toxicity and biological activity of this medicinal plant used in ethnomedicine in different countries for the treatment of similar discomforts and diseases. These results are discussed considering the risk of consuming C. gilliesii, without clear recommendations and control of at least pulegone content in essential oils.

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Clinopodium gilliesii (Benth.) Kuntze, recolectada en el altiplano chileno, contiene un sorprendente 93,87% del monoterpeno toxico pulegona, en el aceite esencial. Estos resultados muestran diferencias notables con estudios de la misma especie realizados en Argentina y Perú. Estas disimilitudes, en la composición de los aceites esenciales deben estar asociadas con diferencias en la toxicidad y actividad biológica de esta especie medicinal que se utiliza en etnomedicina en diferentes lugares para el tratamiento de molestias y enfermedades similares. Estos resultados se discuten considerando el riesgo de consumir C. gilliesii, sin recomendaciones claras y control de al menos el contenido de pulegona en los aceites esenciales.

Asunto(s)

Aceites Volátiles/efectos adversos , Aceites Volátiles/química , Lamiaceae , Monoterpenos/análisis , Plantas Medicinales , Chile , Monoterpenos/efectos adversos

RESUMEN

ABSTRACT Commercial antiparasitics have been the main tool to control parasites, but due to the resistance development, plant extracts have been widely investigated to find new molecules. The present study aimed to investigate the in vitro acaricide and anthelmintic activities of the essential oil from the aerial parts of Hesperozygis myrtoides (A.St.-Hil. ex Benth.) Epling, Lamiaceae. The essential oil was obtained by hydrodistillation analyzed by GC-FID and GC-MS. Four tests were conducted in vitro to screen the antiparasitic action of the essential oil. The evaluation on Rhipicephalus (Boophilus) microplus was performed with the adult immersion test at concentrations ranging from 0.391 to 25 mg/ml and the larval packet test from 3.125 to 100 mg/ml. For Haemonchus contortus the egg hatch test was performed from 0.012 to 25 mg/ml and the larval development test from 0.003 to 0.4 mg/ml. The LC50 and LC90 values were calculated by Probit. The main components identified in the essential oil were isomenthone (47.7%), pulegone (21.4%), limonene (7.7%), isomenthyl acetate (6.8%) and neoisomenthol (3.9%). In the larval packet test the LC50 and LC90 were 13.5 and 21.8 mg/ml, respectively. In egg hatch test, the LC50 and LC90 were 0.249 and 0.797 mg/ml, respectively, while in the larval development test were 0.072 and 0.167 mg/ml, respectively. This is the first report of the H. myrtoides evaluation against those parasites. The anthelmintic results proved its efficacy on H. contortus encouraging new research with a focus on their main bioactives.

RESUMEN

The chemical composition of the essential oil of Kurzamra pulchella (Lamiaceae) was determined. Twelve compounds were identified, with isomenthone (60.6%) and pulegone (37.1%) predominating. Chemotaxonomical considerations were discussed.

Asunto(s)

Lamiaceae/química , Aceites Volátiles/química , Chile , Cromatografía de Gases , Monoterpenos Ciclohexánicos , Lamiaceae/clasificación , Espectrometría de Masas , Monoterpenos

RESUMEN

Abstract This study was developed to evaluate the effect of seasonality on the yield and chemical composition of the essential oil (EO) of Hesperozygis ringens (Benth.) Epling, a native species from the Brazilian Pampa. Leaves were collected from four specimens of a single population in each of the four seasons for a year and were extracted in triplicate by hydro-distillation for 2 hours. The yield of EO (% w/w) was calculated on fresh weight basis (FWB), and the 16 oil samples were analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) were used as statistical tools to evaluate differences in chemical composition. The highest yields were obtained in autumn, spring and summer (2.32-4.38%), while the lowest yields were detected in winter, ranging from 1.15 to 1.91%. Oxygenated monoterpenoids were the predominant class of chemical constituents in the EO obtained in all seasons, showing the highest contents in autumn and summer, and pulegone was identified as a major compound, whose contents varied between 54.13 and 81.17%. The EO samples were divided into three chemical groups by HCA and PCA and were assigned to the same group, except for the three samples gathered in winter. The results showed a seasonal influence on the yield and chemical composition of the EO.(AU)

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Resumo Este estudo foi desenvolvido a fim de avaliar o efeito da sazonalidade no rendimento e composição química do óleo essencial (OE) de Hesperozygis ringens (Benth.) Epling., uma espécie nativa do Pampa brasileiro. Folhas foram coletadas de quatro indivíduos de uma mesma população, em cada uma das quatro estações de um ano, e foram extraídas em triplicada por hidrodestilação durante 2 horas. O rendimento do OE (% m/m) foi calculado considerando a base fresca (BF) e as 16 amostras de óleo foram analisadas por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e cromatografia gasosa com detector de ionização de chamas (CG-DIC). Análise Hierárquica de Cluster (AHC) e Análise de Componentes Principais (ACP) foram utilizadas como ferramentas estatísticas para avaliar as diferenças na composição química. Os maiores rendimentos foram obtidos no outono, primavera e verão (2,32-4,38%), enquanto que os menores foram detectados no inverno, variando de 1,15 até 1,91%. Os monoterpenoides oxigenados foram a classe predominante dos constituintes do OE obtido em todas as estações, apresentando os maiores teores no outono e no verão, e a pulegona foi identificada como o constituinte majoritário, cujos teores variaram entre 54,13 e 81,17%. As amostras de OE foram divididas em três grupos químicos por AHC e ACP e foram classificadas no mesmo grupo, com exceção de três amostras coletadas no inverno. Os resultados demonstraram influência sazonal no rendimento e na composição química dos OE.(AU)

Asunto(s)

Lamiaceae/química , Lamiaceae/crecimiento & desarrollo , Aceites Volátiles/análisis , Aceites Volátiles/química

RESUMEN

Abstract This study was developed to evaluate the effect of seasonality on the yield and chemical composition of the essential oil (EO) of Hesperozygis ringens (Benth.) Epling, a native species from the Brazilian Pampa. Leaves were collected from four specimens of a single population in each of the four seasons for a year and were extracted in triplicate by hydro-distillation for 2 hours. The yield of EO (% w/w) was calculated on fresh weight basis (FWB), and the 16 oil samples were analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) were used as statistical tools to evaluate differences in chemical composition. The highest yields were obtained in autumn, spring and summer (2.32-4.38%), while the lowest yields were detected in winter, ranging from 1.15 to 1.91%. Oxygenated monoterpenoids were the predominant class of chemical constituents in the EO obtained in all seasons, showing the highest contents in autumn and summer, and pulegone was identified as a major compound, whose contents varied between 54.13 and 81.17%. The EO samples were divided into three chemical groups by HCA and PCA and were assigned to the same group, except for the three samples gathered in winter. The results showed a seasonal influence on the yield and chemical composition of the EO.

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Resumo Este estudo foi desenvolvido a fim de avaliar o efeito da sazonalidade no rendimento e composição química do óleo essencial (OE) de Hesperozygis ringens (Benth.) Epling., uma espécie nativa do Pampa brasileiro. Folhas foram coletadas de quatro indivíduos de uma mesma população, em cada uma das quatro estações de um ano, e foram extraídas em triplicada por hidrodestilação durante 2 horas. O rendimento do OE (% m/m) foi calculado considerando a base fresca (BF) e as 16 amostras de óleo foram analisadas por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e cromatografia gasosa com detector de ionização de chamas (CG-DIC). Análise Hierárquica de Cluster (AHC) e Análise de Componentes Principais (ACP) foram utilizadas como ferramentas estatísticas para avaliar as diferenças na composição química. Os maiores rendimentos foram obtidos no outono, primavera e verão (2,32-4,38%), enquanto que os menores foram detectados no inverno, variando de 1,15 até 1,91%. Os monoterpenoides oxigenados foram a classe predominante dos constituintes do OE obtido em todas as estações, apresentando os maiores teores no outono e no verão, e a pulegona foi identificada como o constituinte majoritário, cujos teores variaram entre 54,13 e 81,17%. As amostras de OE foram divididas em três grupos químicos por AHC e ACP e foram classificadas no mesmo grupo, com exceção de três amostras coletadas no inverno. Os resultados demonstraram influência sazonal no rendimento e na composição química dos OE.

Asunto(s)

Lamiaceae/química , Lamiaceae/metabolismo , Aceites Volátiles/química , Aceites Volátiles/metabolismo , Análisis por Conglomerados , Ionización de Llama , Cromatografía de Gases y Espectrometría de Masas , Análisis de Componente Principal , Hojas de la Planta/química , Estaciones del Año

RESUMEN

Abstract This study was developed to evaluate the effect of seasonality on the yield and chemical composition of the essential oil (EO) of Hesperozygis ringens (Benth.) Epling, a native species from the Brazilian Pampa. Leaves were collected from four specimens of a single population in each of the four seasons for a year and were extracted in triplicate by hydro-distillation for 2 hours. The yield of EO (% w/w) was calculated on fresh weight basis (FWB), and the 16 oil samples were analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and gas chromatography with flame ionization detector (GC-FID). Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) were used as statistical tools to evaluate differences in chemical composition. The highest yields were obtained in autumn, spring and summer (2.32-4.38%), while the lowest yields were detected in winter, ranging from 1.15 to 1.91%. Oxygenated monoterpenoids were the predominant class of chemical constituents in the EO obtained in all seasons, showing the highest contents in autumn and summer, and pulegone was identified as a major compound, whose contents varied between 54.13 and 81.17%. The EO samples were divided into three chemical groups by HCA and PCA and were assigned to the same group, except for the three samples gathered in winter. The results showed a seasonal influence on the yield and chemical composition of the EO.

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Resumo Este estudo foi desenvolvido a fim de avaliar o efeito da sazonalidade no rendimento e composição química do óleo essencial (OE) de Hesperozygis ringens (Benth.) Epling., uma espécie nativa do Pampa brasileiro. Folhas foram coletadas de quatro indivíduos de uma mesma população, em cada uma das quatro estações de um ano, e foram extraídas em triplicada por hidrodestilação durante 2 horas. O rendimento do OE (% m/m) foi calculado considerando a base fresca (BF) e as 16 amostras de óleo foram analisadas por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e cromatografia gasosa com detector de ionização de chamas (CG-DIC). Análise Hierárquica de Cluster (AHC) e Análise de Componentes Principais (ACP) foram utilizadas como ferramentas estatísticas para avaliar as diferenças na composição química. Os maiores rendimentos foram obtidos no outono, primavera e verão (2,32-4,38%), enquanto que os menores foram detectados no inverno, variando de 1,15 até 1,91%. Os monoterpenoides oxigenados foram a classe predominante dos constituintes do OE obtido em todas as estações, apresentando os maiores teores no outono e no verão, e a pulegona foi identificada como o constituinte majoritário, cujos teores variaram entre 54,13 e 81,17%. As amostras de OE foram divididas em três grupos químicos por AHC e ACP e foram classificadas no mesmo grupo, com exceção de três amostras coletadas no inverno. Os resultados demonstraram influência sazonal no rendimento e na composição química dos OE.

RESUMEN

O objetivo deste estudo foi comparar o rendimento, a composição química e a atividade antifúngica do óleo essencial de Mentha pulegium (poejo) em diferentes estágios de desenvolvimento, cultivada sob condições controladas no sul do Brasil. A hidrodestilação de folhas frescas de M. pulegium, coletadas aos 60, 70 e 85 dias após o transplante, apresentou rendimento de óleo essencial de 0,17 %, 0,23 % e 0,17 %, respectivamente. Todas as amostras de óleo apresentaram atividade contra Cladosporium herbarum. Através das análises de cromatografia gasosa (GC) e GC/MS do óleo essencial, foram identificados onze constituintes, sete (mentona, isomentona, neoisomentol, pulegona, piperitona, 1.1- dimetoxi-2- nonino e piperitenona) comuns às três amostras, enquanto dois outros (mentofurano, mirtenal) foram detectados somente nas amostras da primeira e segunda coletas. A pulegona foi o principal constituinte nas duas primeiras amostras (26,65 %), seguida pela piperitenona (20,41; 12,60 %). A concentração de pulegona aumentou para 31,05 % na última coleta, porém o constituinte majoritário foi a piperitenona (36,32 %). Os resultados demonstraram que o óleo essencial de M. pulegium apresenta potencial como agente antifúngico e sua composição química depende do estágio de desenvolvimento da planta.(AU)

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The aim of this study was to compare the yield, chemical composition and antifungal activity of the essential oil that is obtained from Mentha pulegium in different developmental stages and cultivated under controlled conditions in southern Brazil. The hydrodistillation of fresh leaves that were collected at 60, 70 and 85 days resulted inessential oil yields of 0.17 %, 0.23 % and 0.17 %, respectively. All of the essential oil samples showed antifungal activity against Cladosporium herbarum. The gas chromatograph (GC) and GC/MS analysis revealed eleven constituents: seven (pulegone, piperitenone, menthone, isomenthone, neoisomenthol, piperitone and 1.1-dimethoxy-2-nonyne) were common to three samples, while menthofuran and myrtenal were detected only in samples of the first and second stages. Pulegone was the main constituent of the essential oil samples from the first and second stages (26.65 %), followed by piperitenone (20.41; 12.60 %). The pulegone concentration increased to 31.05 % in the last collection, while the major constituent was piperitenone (36.32 %). In conclusion, the results demonstrated that M. pulegium essential oil presents potential as an antifungal agent, and its chemical composition depends on the stage of development during which it was extracted.(AU)

Asunto(s)

Mentha pulegium/química , Aceites de Plantas/análisis , Antifúngicos/análisis , Cladosporium/efectos de los fármacos

RESUMEN

O objetivo deste estudo foi comparar o rendimento, a composição química e a atividade antifúngica do óleo essencial de Mentha pulegium (poejo) em diferentes estágios de desenvolvimento, cultivada sob condições controladas no sul do Brasil. A hidrodestilação de folhas frescas de M. pulegium, coletadas aos 60, 70 e 85 dias após o transplante, apresentou rendimento de óleo essencial de 0,17 %, 0,23 % e 0,17 %, respectivamente. Todas as amostras de óleo apresentaram atividade contra Cladosporium herbarum. Através das análises de cromatografia gasosa (GC) e GC/MS do óleo essencial, foram identificados onze constituintes, sete (mentona, isomentona, neoisomentol, pulegona, piperitona, 1.1- dimetoxi-2- nonino e piperitenona) comuns às três amostras, enquanto dois outros (mentofurano, mirtenal) foram detectados somente nas amostras da primeira e segunda coletas. A pulegona foi o principal constituinte nas duas primeiras amostras (26,65 %), seguida pela piperitenona (20,41; 12,60 %). A concentração de pulegona aumentou para 31,05 % na última coleta, porém o constituinte majoritário foi a piperitenona (36,32 %). Os resultados demonstraram que o óleo essencial de M. pulegium apresenta potencial como agente antifúngico e sua composição química depende do estágio de desenvolvimento da planta.

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The aim of this study was to compare the yield, chemical composition and antifungal activity of the essential oil that is obtained from Mentha pulegium in different developmental stages and cultivated under controlled conditions in southern Brazil. The hydrodistillation of fresh leaves that were collected at 60, 70 and 85 days resulted inessential oil yields of 0.17 %, 0.23 % and 0.17 %, respectively. All of the essential oil samples showed antifungal activity against Cladosporium herbarum. The gas chromatograph (GC) and GC/MS analysis revealed eleven constituents: seven (pulegone, piperitenone, menthone, isomenthone, neoisomenthol, piperitone and 1.1-dimethoxy-2-nonyne) were common to three samples, while menthofuran and myrtenal were detected only in samples of the first and second stages. Pulegone was the main constituent of the essential oil samples from the first and second stages (26.65 %), followed by piperitenone (20.41; 12.60 %). The pulegone concentration increased to 31.05 % in the last collection, while the major constituent was piperitenone (36.32 %). In conclusion, the results demonstrated that M. pulegium essential oil presents potential as an antifungal agent, and its chemical composition depends on the stage of development during which it was extracted.

Asunto(s)

Antifúngicos/análisis , Cladosporium/efectos de los fármacos , Mentha pulegium/química , Aceites de Plantas/análisis

RESUMEN

INTRODUCTION: R(+)-pulegone is a ketone monoterpene and it is the main constituent of essential oils in several plants. Previous studies provided some evidence that R(+)-pulegone may act on isolated cardiac myocytes. In this study, we evaluated in extended detail, the pharmacological effects of R(+)-pulegone on cardiac tissue. METHODS: Using in vivo measurements of rat cardiac electrocardiogram (ECG) and patch-clamp technique in isolated myocytes we determinate the influence of R(+)-pulegone on cardiac excitability. RESULTS: R(+)-pulegone delayed action potential repolarization (APR) in a concentration-dependent manner (EC50=775.7±1.48, 325.0±1.30, 469.3±1.91 µM at 10, 50 and 90% of APR respectively). In line with prolongation of APR R(+)-pulegone, in a concentration-dependent manner, blocked distinct potassium current components (transient outward potassium current (I(to)), rapid delayed rectifier potassium current (I(Kr)), inactivating steady state potassium current (I(ss)) and inward rectifier potassium current (I(K1))) (EC50=1441±1.04; 605.0±1.22, 818.7±1.22; 1753±1.09 µM for I(to), I(Kr), I(ss) and I(K1), respectively). The inhibition occurred in a fast and reversible way, without changing the steady-state activation curve, but instead shifting to the left the steady-state inactivation curve (V1/2 from -56.92±0.35 to -67.52±0.19 mV). In vivo infusion of 100 mg/kg R(+)-pulegone prolonged the QTc (∼40%) and PR (∼62%) interval along with reducing the heart rate by ∼26%. CONCLUSION: Taken together, R(+)-pulegone prolongs the APR by inhibiting several cardiomyocyte K(+) current components in a concentration-dependent manner. This occurs through a direct block by R(+)-pulegone of the channel pore, followed by a left shift on the steady state inactivation curve. Finally, R(+)-pulegone induced changes in some aspects of the ECG profile, which are in agreement with its effects on potassium channels of isolated cardiomyocytes.

Asunto(s)

Potenciales de Acción/efectos de los fármacos , Monoterpenos/farmacología , Miocitos Cardíacos/efectos de los fármacos , Aceites Volátiles/química , Aceites de Plantas/química , Canales de Potasio/efectos de los fármacos , Animales , Monoterpenos Ciclohexánicos , Electrocardiografía , Femenino , Corazón/efectos de los fármacos , Masculino , Técnicas de Placa-Clamp , Ratas , Ratas Wistar

RESUMEN

In the present work an analytical methodology to micro scale based on the use of the HS-SPME/GC-MS to determine volatile compounds present in Clinopodium odorum (Griseb.) Harley (Lamiaceae)was optimized and settled differences and similarities with itsessential oil. A systematic description of the volatile components of flowers, stems, leaves and combined aerial parts (whole plant) was constructed via GC-MS analyses of HS-SPME adsorbed compounds and of essential oils obtained through hydrodistillation of the same tissues. Pulegone was the main component of both the HS-SPME analysis and essential oil analysis. In addition, piperitenone oxide andpiperitone oxide were the other main components in the essential oil whereas in the HS-SPME analysis cis-isopulegone and menthone prevailed. The HS-SPME method can achieve comparable results to those obtained by essential oil analysis, by using very fewer samples, ashorter extraction time and a much simpler procedure.

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En el presente trabajo se ha optimizado una metodología analítica a micro-escala basada en HS-SPME/GC-MS para determinar los compuestos volátiles presentes en Clinopodium odorum (Griseb.) Harley (Lamiaceae), y se establecieron diferencias y similitudes con su aceite esencial. Se realizó una descripción sistemática de los componentes volátiles de flores, tallos, hojas y partes aéreas combinadas(planta entera) a partir de los análisis por GC-MS a través del sistema HS-SPME y de los aceites esenciales. Pulegona fue el componenteprincipal tanto del análisis por HS-SPME, como del aceite esencial. Además, el óxido de piperitenona y el óxido de piperitona eran los otroscomponentes principales en el aceite esencial mientras que en el análisis por HS-SPME, prevalecieron cis-isopulegona y mentona. El método de HS-SPME puede lograr resultados comparables a los obtenidos por el análisis de aceite esencial, mediante el uso de muestras de menor tamaño, un tiempo de extracción más corto y un procedimiento más simple.

Asunto(s)

Aceites Volátiles/química , Cromatografía de Gases y Espectrometría de Masas/métodos , Destilación , Lamiaceae/química , Mentol/análisis , Monoterpenos/análisis

RESUMEN

Recent studies have shown the spasmolytic activity of p-menthane monoterpenes (+)-pulegone and 4-terpinyl acetate (4-T) in guinea pig ileum. Since the action mechanism of these monoterpenes in intestinal smooth muscle is unknown, the present study was conducted to characterize their relaxant mechanism in isolated guinea pig ileum. We tested the involvement of voltage-dependent calcium and potassium channels and muscarinic antagonism. Both the monoterpenes caused a shift in the calcium curve to the right with reduction in the maximum effect. Pretreatment with tetraethylammonium chloride partially inhibited relaxation produced by both 4-T and (+)-pulegone. Both compounds caused a shift in the bethanechol curve to the right with reduction in the maximum effect. The results of this study indicate that the mechanisms of action of the smooth muscle relaxant monoterpenes (+)-pulegone and 4-T possibly involve the partial blockade of calcium channels, the activation of potassium channels, and the non-competitive antagonism of muscarinic receptors.

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Estudios recientes han demostrado la actividad espasmolítica de los monoterpenos p-mentano de (+)-pulegona y acetato de 4-terpinilo (4-T) en el íleon de cobayo. Dado que el mecanismo de acción de estos monoterpenos en el músculo liso intestinal es desconocido, el presente estudio se llevó a cabo para caracterizar su mecanismo relajante en íleon aislado de conejillo de indias. Hemos probado la participación de tanto los canales calcio dependiente de voltaje como los canales de potasio y antagonistas muscarínicos. Ambos monoterpenos causaron un desplazamiento en la curva de calcio a la derecha con la reducción en el efecto máximo. El tratamiento previo con cloruro de tetraetilamonio inhibe parcialmente la relajación producida por tanto 4-T y (+)-pulegona. Ambos compuestos causaron un cambio en la curva de betanecol a la derecha con la reducción en el efecto máximo. Los resultados de este estudio indican que los mecanismos de acción de los monoterpenos relajantes del músculo liso (+)-pulegona y 4-T posiblemente implican el bloqueo parcial de los canales de calcio, la activación de los canales de potasio, y el antagonismo no competitivo de los receptores muscarínicos.

Asunto(s)

Animales , Cobayas , Íleon , Monoterpenos/farmacología , Monoterpenos/química , Hojas de la Planta , Parasimpatolíticos/farmacología , Aceites Volátiles/farmacología , Antagonistas Muscarínicos/farmacología , Canales Iónicos , Músculo Liso , Relajación Muscular