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Article in Chinese | WPRIM | ID: wpr-879015


The volatile oil from Mastiche and Olibanum medicinal materials was extracted by steam distillation, and the chemical components of the volatile oil were analyzed by GC-MS technology. The differences of the volatile oil components were compared and study on the Helicobacter pylori in vitro antimicrobial activitiy was conducted. The results showed that the yields of the volatile oil from Mastiche and Olibanum were 11.93% and 2.40%, respectively. A total of 46 compounds(91.31%) were identified from the volatile oil from Mastiche annd 35 compounds(92.49%) from Olibanum. The classification and comparison study of the components showed that the content of monoterpenes in the volatile oil from Mastiche was the highest(40.69%), followed by alcohols(28.48%); while the content of alcohols in the volatile oil from Olibanum was the highest(35.81%), followed by esters(24.92%). There were significant differences in the components of volatile oil from Mastiche and Olibanum, which might be one of the reasons for the difference in efficacy and application. In vitro bacteriostatic experiments showed that the minimum inhibitory concentration(MIC) of the volatile oil from Mastiche against H. pylori was 1 mg·mL~(-1), and the MIC of the volatile oil from Olibanum against H. pylori was more than 1 mg·mL~(-1). In combination with the results of the oil yield experiment, Mastiche had the advantage of inhibiting H. pylori activity. The research results provide scientific basis for the rational application of Mastiche and Olibanum.

Anti-Bacterial Agents/pharmacology , Frankincense , Gas Chromatography-Mass Spectrometry , Helicobacter pylori , Monoterpenes/analysis , Oils, Volatile/pharmacology
Article in Chinese | WPRIM | ID: wpr-878981


To compare the effect of hot or warm property of Chinese medicine(CM) on the skin toxicity of essential oils(EOs) as penetration enhancer in vitro and in vivo, and explore the mechanism. EOs were extracted from WIM of Bichengqie(Litseae Fructus), Dingxiang(Flos Syzygii Aromatici), Huajiao(Pericarpium Zanthoxyli Bungeani), and Xiaohuixiang(Fructus Foeniculi) with warm property, and Ganjiang(Rhizoma Zingiberis), Gaoliangjiang(Rhizoma Alpiniae Officinari), Hujiao(Fructus Piperis), and Wuzhuyu(Fructus Evodiae Rutaecarpae) with hot property, respectively. Then the in vitro toxicity was evaluated by human keratinocyte cytotoxicity. In vivo skin irritation potency was also evaluated through pathological observation after topical administration. The components, especially those located in stratum corneum, were analyzed by GC-MS. The main components, namely monoterpenes and sesquiterpenes, of EOs extracted from CM with hot property,were detected for the interaction with keratino-lipid ceramide 3 by molecular simulation technology; and the interaction energy value was calculated based on the optimal conformation. It was found that the skin cell toxicity of EOs from CM with hot property was significantly higher than that of EOs from CM with warm property. However, there was no significant difference between them by in vivo skin irritation evaluation. Whether from CM with hot property or warm property, EOs showed a significant reduced toxicity compared with azone. Sesquiterpenes(33.56%±19.38%) were found to be one of the main components in EOs from CM with hot property, while almost no sesquiterpenes was found in EOs from CM with warm property. After topical administration of EOs from CM with hot property, sesquiterpenes were demonstrated to be prone to locate in stratum corneum. The results of molecular simulation also revealed that the interaction between sesquiterpenes and ceramide 3 was significantly stronger than that of monoterpenes(P<0.01). In conclusion, the location of sesquiterpenes in stratum corneum resulted in the significant difference between in vitro skin cell toxicity and in vivo skin irritation potency. The EOs from CM with hot property shall be taken into account for further development of potent penetration enhancer.

Humans , Monoterpenes/metabolism , Oils, Volatile/toxicity , Sesquiterpenes/metabolism , Skin/metabolism , Skin Absorption
Article in English | LILACS | ID: biblio-1284447


This paper described the chemical compositions and antimicrobial activity of the essential oils from the leaves and stem of Amomum rubidumLamxay & N. S. Lý, collected from Bidoup Nui Ba National Park, Lam Dong, Vietnam. The essential oils were obtained by hydrodisitllation method while antimicrobial activity was evaluetd by microdilution broth susceptibility assay. The main constituents of the leaf essential oil were identified as 1,8-cineole (37.7%), δ-3-carene (19.5%) and limonene (16.3%) while δ-3-carene (21.9%), limonene (17.8%) and ß-phellandrene (14.6%) dominated in the stem essentialoil. The leaf and stem essential oils displayed stronger inhibition of Pseudomonas aeruginosa with MIC of 25 µg/mLand 50 µg/mL respectively. The stem essential oil was active against Candida albicans (MIC, 50 µg/mL) while both essential oils inhibited the growth of Fusarium oxysporum (MIC 50 µg/mL). This is the first report on chemical constituents and antimicrobial activity of the essential oils of A. rubidum.

Este artículo describe la composición química y la actividad antimicrobiana de aceites esenciales de las hojas y el tallo de Amomum rubidum Lamxay & N. S. Lý recolectados del Parque Nacional Bidoup Nui Ba, Lam Dong, Vietnam. Los aceites esenciales se obtuvieron mediante el método de hidrodisitilación, mientras que la actividad antimicrobiana se evaluó mediante un ensayo de susceptibilidad de caldo de microdilución. Los principales componentes del aceite esencial de la hoja se identificaron como 1,8-cineol (37,7%), δ-3-careno (19,5%) y limoneno (16,3%), mientras que δ-3-careno (21,9%), limoneno (17,8 %) y ß-felandreno (14,6%) dominaron en el aceite esencial del tallo. Los aceites esenciales de hoja y tallo mostraron una inhibición más fuerte de Pseudomonas aeruginosa con un MIC de 25 µg/mL y 50 µg/mL, respectivamente. El aceite esencial del tallo fue activo contra Candida albicans (MIC, 50 µg/mL) mientras que ambos aceites esenciales inhibieron el crecimiento de Fusarium oxysporum (MIC 50 µg/mL). Este es el primer informe sobre los componentes químicos y la actividad antimicrobiana de los aceites esenciales de A. rubidum.

Oils, Volatile/pharmacology , Amomum/chemistry , Anti-Infective Agents/pharmacology , Pseudomonas aeruginosa/drug effects , Candida albicans/drug effects , Oils, Volatile/chemistry , Microbial Sensitivity Tests , Distillation , Chromatography, Gas , Plant Stems , Plant Leaves , Monoterpenes/analysis , Fusarium/drug effects , Anti-Infective Agents/chemistry
Bol. latinoam. Caribe plantas med. aromát ; 20(1): 61-70, 2021. tab, ilus
Article in English | LILACS | ID: biblio-1284444


Identification of the chemical compositionof essential oils is very important for ensuring the quality of finished herbal products. The objective of the study was to analyze the chemical components present in the essential oils of five Beilschmiediaspecies (i.e. B. kunstleri, B. maingayi, B. penangiana, B. madang, and B. glabra) by multivariate data analysis using principal component analysis (PCA) and hierarchical clustering analysis (HCA) methods. The essential oils were obtained by hydrodistillation and fully characterized by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 108 chemical components were successfully identified from the essential oils of five Beilschmiediaspecies. The essential oils were characterized by high proportions of ß-caryophyllene (B.kunstleri), δ-cadinene (B. penangianaand B. madang), and ß-eudesmol (B. maingayiand B. glabra). Principal component analysis (PCA) and hierarchical cluster analysis (HCA) revealed that chemical similarity was highest for all samples, except for B. madang. The multivariate data analysis may be used for the identification and characterization of essential oils from different Beilschmiediaspecies that are to be used as raw materials of traditional herbal products.

La identificación de la composición química de los aceites esenciales es muy importante para garantizar la calidad de los productos herbales terminados. El objetivo del estudio fue analizar los componentes químicos presentes en los aceites esenciales de cinco especies de Beilschmiedia (B. kunstleri, B. maingayi, B. penangiana, B. madangy B. glabra) mediante análisis de datos multivariados utilizando los métodos de análisis de componente principal (PCA) y análisis de agrupamiento jerárquico (HCA). Los aceites esenciales se obtuvieron por hidrodestilación y se caracterizaron completamente por cromatografía de gases (GC) y cromatografía de gases-espectrometría de masas (GC-MS). Se identificaron con éxito un total de 108 componentes químicos a partir de los aceites esenciales de las cinco especies de Beilschmiedia. Los aceites esenciales se caracterizaron por altas proporciones de ß-cariofileno (B. kunstleri), δ-cadineno (B. penangianay B. madang) y ß-eudesmol (B. maingayiy B. glabra). El análisis de componentes principales (PCA) y el análisis de conglomerados jerárquicos (HCA) revelaron que la similitud química fue más alta para todas las muestras, excepto para B. madang. El análisis de datos multivariados puede usarse para la identificación y caracterización de aceites esenciales de diferentes especies de Beilschmiedia que se utilizan como materias primas de productos herbales tradicionales.

Oils, Volatile/chemistry , Lauraceae/chemistry , Sesquiterpenes/analysis , Cluster Analysis , Distillation , Multivariate Analysis , Chromatography, Gas/methods , Principal Component Analysis , Monoterpenes/analysis
Article in Chinese | WPRIM | ID: wpr-878849


Chemical investigation on the constituents of the ethyl acetate soluble extraction of Litsea cubeba has resulted in the isolation and structure elucidation of thirty compounds, including one sesquiterpene(1), four monoterpenes(2-5), two γ-butyrolactone derivatives(6 and 7), seven tyramine derivatives(8-14), fifteen aromatic compounds(15-29), and one pyrone derivative(30) via various chromatographic techniques and spectroscopic data analysis(MS, IR, 1 D and 2 D NMR). Compounds 1-7, 13 and 14 were obtained from the genus Litsea for the first time.

Acetates , Litsea , Monoterpenes , Sesquiterpenes
J. appl. oral sci ; 28: e20190519, 2020. tab, graf
Article in English | LILACS, BBO | ID: biblio-1101254


Abstract Natural products have emerged as a rich source of bioactive compounds for adjunctive treatments of many infectious and inflammatory conditions, including periodontitis. Among the monoterpenes with significant biological properties, there is the perillyl alcohol (POH), which can be found in several essential oils and has shown immunomodulatory properties in recent studies, which may be interesting in the treatment of non-neoplastic inflammatory disorders. Objective To determine the antibacterial and immune modulatory activities of the POH. Methodology The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) of the POH for two significant Gram-negative periodontal pathogens were determined by macrodilution and subculture, respectively. Cell proliferation and cytotoxicity in RAW 264.7 macrophages were determined by Trypan Blue and mitochondrial enzymatic activity assay. The modulation of reactive oxygen species (ROS) was analyzed by flow cytometry and expression of TNF and arginase-1 by real-time PCR. Results The POH was effective against P. gingivalis (ATCC 33277) and F. nucleatum (ATCC 25586) with MIC= MBC=1600 μM. No cytotoxicity up to 100 µM was observed on macrophages. The cell proliferation was inhibited from 48 hours at 100 μM (p<0.05) and 250 μM (p<0.01). The POH increased ROS production at both 10 μM and 100 μM (p<0.05) in unstimulated cells. The PMA-induced ROS production was not affected by POH, whereas 100 μM significantly reduced lipopolysaccharide-induced (LPS-induced) ROS. The expression of TNF was not affected by POH in unstimulated cells or in cells polarized to M1 phenotype, whereas both concentrations of POH reduced (p<0.05) the expression of arginase-1 in M2-polarized macrophages. Conclusion The POH has antibacterial activity against periodontal pathogens and reduced proliferation of murine macrophages without significant cytotoxicity at concentrations up to 100 μM. In addition, the POH reduced the LPS-induced ROS and the expression of arginase-1 in M2-polarized macrophages.

Animals , Mice , Fusobacterium nucleatum/drug effects , Reactive Oxygen Species/analysis , Porphyromonas/drug effects , Monoterpenes/pharmacology , Macrophages/drug effects , Anti-Bacterial Agents/pharmacology , Arginase/analysis , Time Factors , Biological Products/pharmacology , Microbial Sensitivity Tests , Gene Expression , Lipopolysaccharides/pharmacology , Reproducibility of Results , Tumor Necrosis Factor-alpha/analysis , Fusobacterium nucleatum/growth & development , Reactive Oxygen Species/metabolism , Porphyromonas/growth & development , Cell Proliferation/drug effects , Real-Time Polymerase Chain Reaction , Flow Cytometry , RAW 264.7 Cells , Macrophages/metabolism
Article in English | LILACS | ID: biblio-1284300


The chemical composition and larvicidal activity of essential oils derived from the leaves and rhizomes of Zingiber montanum (J. Koenig) Link ex. A. Dietr. were reported. The main compounds in the leaf oil were ß-pinene (13.8%), ß-phellandrene (11.3%) and α-pinene (7.3%) while the rhizome oil was dominated by sabinene (41.1%), terpinen-4-ol (22.7%) and (E)-nerolidol (14.3%). The minimum lethal concentration (larvicidal activity) LC50of the rhizome oil at 24 h against Aedes albopictus was 35.17 µg/mL, while LC50 values of 32.20 µg/mL and 31.12 µg/mL were obtained against Aedes aegypti and Culex quinquefasciatus respectively. At 48 h the oil displayed larvicidal action with LC50 values of 23.18 µg/mL, 25.58 µg/mL and 18.99 µg/mL respectively towards Ae. albopictus, Ae. Aegyptiand Cx. quinquefasciatus. The leaf oil did not exhibit significant mortality and larvicidal action. The results indicate the potential of rhizome essential oil of Z. montanumas a source of larvicidal agent.

En el presente trabajo se reportan la composición química y actividad larvicida de los aceites esenciales obtenidos de hojas y rizomas de Zingiber montanum (J. Koenig) Link ex. A. Dietr. Los principales compuestos en el aceite de hojas fueron ß-pineno (13.8%), ß-felandrene (11.3%) y α-pineno (7.3%); mientras que los más abundantes en el aceite de rizomas fueron sabineno (41.1%), terpinen-4-ol (22.7%) y (E)-nerolidol (14.3%). La concentración letal mínima (actividad larvicida) LC50 del aceite de riomas ante Aedes albopictus fue 35.17 µg/mL, mientras que los valores de LC50 de 32.20 µg/mL y 31.12 µg/mL fueron obtenidos ante Aedes aegyptiy Culex quinquefasciatus respectivamente. A las 48 horas, el aceite mostró acción larvicida con valores de LC50 de 23.18 µg/mL, 25.58 µg/mL y 18.99 µg/mL respectivamente, ante Ae. albopictus, Ae. Aegyptiand Cx. quinquefasciatus. El aceite de hojas no mostró mortalidad ni acción larvicida significativa. Los resultados indican el potencial del aceite esencial de rizomas de Z. montanum como una fuente de agentes larvicidas.

Animals , Pesticides/pharmacology , Oils, Volatile/pharmacology , Zingiberaceae/chemistry , Culicidae/drug effects , Pesticides/chemistry , Oils, Volatile/chemistry , Analysis of Variance , Chromatography, Gas , Aedes/drug effects , Culex/drug effects , Monoterpenes/analysis , Larvicides , Mosquito Vectors
Rev. bras. parasitol. vet ; 29(1): e013119, 2020. tab, graf
Article in English | LILACS | ID: biblio-1058018


Abstract The objective of this study was to evaluate the efficacy of carvacryl acetate (CVA) and nanoencapsulated CVA (nCVA) on gastrointestinal nematodes of sheep. The CVA was nanoencapsulated with chitosan/gum arabic and the efficacy of nanoencapsulation (EE), yield, zeta potential, nanoparticle morphology and release kinetics at pH 3 and 8 were analyzed. Acute and subchronic toxicity were evaluated in rodents and reduction of egg counts in the faeces (FECRT) of sheep. The sheep were divided into four groups (n = 10): G1, 250 mg/kg CVA; G2, 250 mg/kg nCVA; G3, polymer matrix and G4: 2.5 mg/kg monepantel. EE and nCVA yield were 65% and 57%, respectively. The morphology of the nanoparticles was spherical, size (810.6±286.7 nm), zeta potential in pH 3.2 (+18.3 mV) and the 50% release of CVA at pHs 3 and 8 occurred at 200 and 10 h, respectively. nCVA showed LD50 of 2,609 mg/kg. CVA, nCVA and monepantel reduced the number of eggs per gram of faeces (epg) by 57.7%, 51.1% and 97.7%, respectively. The epg of sheep treated with CVA and nCVA did not differ from the negative control (P>0.05). Nanoencapsulation reduced the toxicity of CVA; however, nCVA and CVA presented similar results in the FECRT.

Resumo O objetivo deste trabalho foi avaliar a eficácia do acetato de carvacrila (ACV) e do ACV nanoencapsulado (nACV) sobre nematóides gastrintestinais de ovinos. O ACV foi nanoencapsulado com quitosana/goma arábica e foi analisada a eficácia de nanoencapsulamento (EE), o rendimento, potencial zeta, morfologia das nanopartículas e cinética de liberação em pH 3 e 8. Foram avaliadas as toxicidades aguda e subcrônica em roedores e a redução da contagem de ovos nas fezes (RCOF) de ovinos. Os ovinos foram divididos em quatro grupos (n = 10): G1, 250 mg/kg ACV; G2, 250 mg/kg de nACV; G3, matriz polimérica e G4: 2,5 mg/kg de monepantel. A EE e o rendimento de nACV foram de 65% e 57%, respectivamente. A morfologia das nanopartículas foi esférica, tamanho (810,6±286,7 nm), potencial zeta no pH 3,2 (+18,3 mV) e a liberação de 50% de CVA nos pHs 3 e 8 ocorreu às 200 e 10 h, respectivamente. nACV apresentou DL50 de 2.609 mg/kg. ACV, nACV e o monepantel reduziram a contagem de ovos por grama de fezes (opg) em 57,7%, 51,1% e 97,7%, respectivamente. A contagem de opg de ovelhas tratadas com ACV e nCVA não diferiu do controle negativo (P>0,05). O nanoencapsulamento reduziu a toxicidade do AVC; no entanto, nACV e ACV apresentaram resultados semelhantes na RCOF.

Animals , Female , Sheep Diseases/drug therapy , Monoterpenes/administration & dosage , Gastrointestinal Tract/parasitology , Nanocapsules/administration & dosage , Anthelmintics/administration & dosage , Nematoda/drug effects , Nematode Infections/drug therapy , Parasite Egg Count , Rodentia , Sheep Diseases/parasitology , Sheep , Toxicity Tests , Parasitic Sensitivity Tests , Monoterpenes/toxicity , Nanocapsules/toxicity , Feces/parasitology , Real-Time Polymerase Chain Reaction , Anthelmintics/toxicity , Mice , Nematoda/isolation & purification , Nematoda/classification , Nematode Infections/parasitology
Bol. latinoam. Caribe plantas med. aromát ; 18(6): 566-576, nov. 2019. ilus, tab
Article in English | LILACS | ID: biblio-1102643


This paper reports for the first time volatile compounds, anti-nociceptive and anti-inflammatory activities of essential oils from the leaves of Waltheria indica L. (Stericullaceae) growing in Nigeria. The essential oil was hydro-distilled and characterized by gas chromatography-flame ionization detection (GC-FID) and gas chromatography coupled with mass spectrometry (GC-MS) analyses. The anti-inflammatory activity was evaluated on carrageenan induced rat paw edema while the anti-nociceptive test was based on hot plate model. The hydro-distillation afforded 0.41% (dry weight basis) of light green oil. Forty compounds representing 99.8% were identified in the oil. The main constituents of the oil were limonene (34.7%), sabinene (21.2%) and citronellal (9.7%). The anti-nociceptive property of the essential oils statically inhibited edema development (p<0.001) at a dose of 200 and 400 mg/kg independent of time of exposure. However, the 100 mg/kg Waltheria indica essential oils (WIEO) displayed a relatively low inhibition (p<0.01-p>0.5) which declines as exposure time increases. The anti-inflammatory activities shows a steady rate and non-dose dependent activity (p<0.001) up to the 3rd h of inflammation study. Conversely, a sharp reduction at the rate of p<0.5, 0.1 and 0.01 for the 100, 200 and 400 mg/kg WIEO doses respectively. Overall, the results presented sustain and establish the anti-nociceptive and anti-inflammatory properties and justifies the need for further evaluation and development of the essential oils from this plant.

Este artículo informa por primera vez de compuestos volátiles, actividades anti-nociceptivas y antiinflamatorias de aceites esenciales de las hojas de Waltheria indica L. (Stericullaceae) que crecen en Nigeria. El aceite esencial fue hidro-destilado y se caracterizó por cromatografía de gases-detección de ionización de llama (GC-FID) y cromatografía de gases junto con análisis de espectrometría de masas (GC-MS). La actividad antiinflamatoria se evaluó en el edema de pata de rata inducido por carragenano, mientras que la prueba antinociceptiva se basó en el modelo de placa caliente. La destilación hidráulica proporcionó 0,41% (en peso seco) de aceite verde claro. Cuarenta compuestos que representan el 99.8% fueron identificados en el aceite. Los principales componentes del aceite fueron el limoneno (34,7%), el sabineno (21,2%) y el citronelal (9,7%). La propiedad anti-nociceptiva de los aceites esenciales inhibió estáticamente el desarrollo del edema (p<0.001) a una dosis de 200 y 400 mg/kg independientemente del tiempo de exposición. Sin embargo, los aceites esenciales de Waltheria indica de 100 mg/kg (WIEO) mostraron una inhibición relativamente baja (p<0.01-p>0.5) que disminuye a medida que aumenta el tiempo de exposición. Las actividades antiinflamatorias muestran una tasa constante y una actividad no dependiente de la dosis (p<0.001) hasta la tercera hora del estudio de inflamación. Por el contrario, una fuerte reducción a una tasa de p<0.5, 0.1 y 0.01 para las dosis de 100, 200 y 400 mg/kg de WIEO respectivamente. En general, los resultados presentados sostienen y establecen las propiedades anti-nociceptivas y antiinflamatorias y justifican la necesidad de una mayor evaluación y desarrollo de los aceites esenciales de esta planta.

Animals , Male , Female , Rats , Oils, Volatile/pharmacology , Malvaceae/chemistry , Anti-Inflammatory Agents/pharmacology , Temperature , Carrageenan/toxicity , Chromatography, Gas/methods , Rats, Wistar , Monoterpenes/analysis , Flame Ionization , Analgesics/pharmacology , Inflammation/chemically induced
Bol. latinoam. Caribe plantas med. aromát ; 18(5): 480-491, sept. 2019. ilus, tab
Article in English | LILACS | ID: biblio-1008273


In the present study, we investigated the antiproliferative activity of essential oil from leaves of Melissa officinalis L. grown in Southern Bosnia and Herzegovina. In vitro evaluation of antiproliferative activity of the M. officinalis essential oil was carried out on three human tumor cell lines: MCF-7, NCI-H460 and MOLT-4 by MTT assay. M. officinalis essential oil was characterized by high percentage of monoterpenes (77,5%), followed by the sesquiterpene fraction (14,5%) and aliphatic compounds (2,2%). The main constituents of the essential oil of M. officinalis are citral (47,2%), caryophyllene oxide (10,2%), citronellal (5,4%), geraniol (6,6%), geranyl acetate (4,1%) and ß- caryophyllene (3,8%). The essential oil showed significant antiproliferative activity against three cancer cell lines, MOLT-4, MCF-7, and NCI-H460 cells, with GI50 values of <5, 6±2 and 31±17 µg/mL, respectively. The results revealed that M. officinalis L. essential oil has a potential as anticancer therapeutic agent.

En el presente estudio, investigamos la actividad antiproliferativa del aceite esencial de las hojas de Melissa officinalis L. cultivadas en el sur de Bosnia y Herzegovina. La evaluación in vitro de la actividad antiproliferativa del aceite esencial de M. officinalis se llevó a cabo en tres líneas celulares de tumores humanos: MCF-7, NCI-H460 y MOLT-4 utilizando el ensayo de MTT. El aceite esencial de M. officinalis se caracterizó por un alto porcentaje de monoterpenos (77,5%), seguido de la fracción sesquiterpénica (14,5%) y compuestos alifáticos (2,2%). Los principales constituyentes del aceite esencial de M. officinalis fueron citral (47,2%), óxido de cariofileno (10,2%), citronelal (5,4%), geraniol (6,6%), acetato de geranilo (4, 1%), y ß-cariofileno (3,8%). El aceite esencial mostró una actividad antiproliferativa significativa contra las líneas celulares de cáncer MOLT-4, MCF-7 y NCI-H460, con valores GI50 de <5, 6±2 y 31±17 µg/mL, respectivamente. Los resultados revelaron que el aceite esencial de M. officinalis L. tiene potencial como agente terapéutico contra el cáncer.

Oils, Volatile/pharmacology , Melissa , Antineoplastic Agents/pharmacology , Sesquiterpenes/analysis , In Vitro Techniques , Oils, Volatile/chemistry , Tumor Cells, Cultured , Plant Leaves , Monoterpenes/analysis , Cell Line, Tumor/drug effects , Cell Proliferation/drug effects , Gas Chromatography-Mass Spectrometry , Antineoplastic Agents/chemistry
Bol. latinoam. Caribe plantas med. aromát ; 18(4): 435-443, jul. 2019. ilus, tab
Article in English | LILACS | ID: biblio-1008258


Volatiles compounds are involved in defensive induction against insects, playing an important role in insect-plant interaction being induced by response to mechanical damage. However, they could decrease according to the domestication degree in cultivated plants. Currently, it has been established that secondary metabolites are reduced due to the domestication process in murtilla. Hence, the follow question emerges: Are volatile organic compounds induced by mechanical damage reduced in cultivated murtilla plants in relation to wild plants? Two cultivated ecotypes and their respective wild counterparts were sampled. Volatiles compounds were obtained using Porapak-Q columns and analyzed by gas chromatography. Results showed that compounds as 2-hexanone, α-pinene, 2-thujene, 3-thujene and 1,8- cineole were more abundant in wild plants exposed to a mechanical damage than cultivated plants. Hence, these compounds have been associated to induced defense, these results suggest that domestication reduced the induction of defensive volatiles in cultivated murtilla in response to mechanical damage.

Los compuestos volátiles están implicados en la defensa inducida contra insectos, desempeñando un papel importante en esta interacción. Sin embargo, estos compuestos podrían disminuir según el grado de domesticación. Actualmente, se ha reportado que algunos metabolitos secundarios son reducidos en plantas de murtilla domesticadas. Por lo tanto, surge la siguiente pregunta de investigación: ¿Los compuestos orgánicos volátiles inducidos por el daño mecánico son reducidos en plantas cultivadas de murtilla en comparación con plantas silvestres? Para dos ecotipos cultivados y sus respectivas contrapartes silvestres, los compuestos volátiles fueron capturados usando columnas de Porapak-Q y las muestras analizadas por cromatografía gaseosa. Los resultados mostraron que compuestos tales como 2- hexanona, α-pineno, 2-tujeno, 3-tujeno y 1,8-cineol fueron más abundantes en plantas silvestres expuestas a daño mecánico que en cultivadas. Debido a que estos compuestos se han asociado a defensa inducida, estos resultados sugieren que la domesticación reduce la inducción de volátiles en plantas cultivadas sometidas a daño mecánico.

Animals , Oils, Volatile/metabolism , Myrtaceae/metabolism , Myrtaceae/microbiology , Domestication , Insecta/physiology , Sesquiterpenes/analysis , Sesquiterpenes/metabolism , Oils, Volatile/chemistry , Myrtaceae/chemistry , Monoterpenes/analysis , Monoterpenes/metabolism , Wilderness , Larva/physiology , Gas Chromatography-Mass Spectrometry
Bol. latinoam. Caribe plantas med. aromát ; 18(3): 325-335, mayo 2019. tab, ilus
Article in English | LILACS | ID: biblio-1008004


The concentration and composition of an essential oil can vary according to environmental variations and seasonal periods. The objective of this study was to correlate meteorological elements with the content and concentration of components of Aloysia triphylla essential oil, for the four seasons of the year. The experiment was conducted in a plastic greenhouse of the UFSM, Frederico Westphalen campus ­ RS, Brazil, in a complete randomized blocks design during the four seasons, with three repetitions. The meteorological data were collected with the aid of a compact meteorological station, in order to characterize the environment in which the species was conducted. The evaluations were carried out at the middle date of each season. It was observed a correlation between the meteorological variables with the essential oil production and its components. According to the analysis, there influence of the temperature on the essential oil contents, considering that the maximum temperature shows a direct positive influence on the concentration of limonene and negative for spathulenol.

El contenido y la composición de un aceite esencial pueden variar según las variaciones ambientales y los períodos estacionales. El objetivo de este estudio fue correlacionar los elementos meteorológicos con el contenido y la concentración de los componentes del aceite esencial de Aloysia triphylla, para las cuatro estaciones del año. El experimento se realizó en un invernadero de plástico de la UFSM, campus de Frederico Westphalen - RS, Brasil, en un diseño completo de bloques al azar durante las cuatro estaciones, con tres repeticiones. Los datos meteorológicos se recopilaron con la ayuda de una estación meteorológica compacta, para caracterizar el entorno en el que se realizó la especie. Las evaluaciones se llevaron a cabo en la fecha media de cada temporada. Se observó una correlación entre las variables meteorológicas con la producción de aceites esenciales y sus componentes. De acuerdo con el análisis, existe una influencia de la temperatura en los contenidos de aceites esenciales, considerando que la temperatura máxima muestra una influencia positiva directa sobre la concentración de limoneno y negativa para el espatulenol.

Seasons , Oils, Volatile/chemistry , Verbenaceae/chemistry , Temperature , Brazil , Monoterpenes/chemistry , Flame Ionization , Gas Chromatography-Mass Spectrometry
Bol. latinoam. Caribe plantas med. aromát ; 18(2): 95-105, mar. 2019. tab
Article in English | LILACS | ID: biblio-1007685


The Lippia alba species consists of an aromatic plant used in Brazilian traditional medical practice and in the medical practice of several countries as well. Presenting a wide variability in its essential oil chemical composition, the Lippia alba is classified in chemotypes, or chemical races, according to the major constituents contained in its essential oil. Considering the quali and quantitative distribution of the components in the essential oil affect directly its pharmacological properties, which are presented in the medicinal species, this paper proposes a scientific literature review to correlate both biological and pharmacological properties presented by L. alba according to its chemical constitution.

Lippia alba es una planta aromática utilizada en la medicina tradicional de Brasil y de varios países. Con una gran variabilidad en la composición química de su aceite esencial, se clasifica en quimiotipos, o razas químicas, de acuerdo con los constituyentes mayoritarios presentes en el aceite esencial. Dado que la distribución cualitativa y cuantitativa de los componentes del aceite esencial afecta directamente a las propiedades farmacológicas presentadas por la especie medicinal, este trabajo propone realizar una revisión en la literatura científica para correlacionar las propiedades biológicas y farmacológicas de los quimiotipos presentes en el aceite essencial de la L. alba.

Oils, Volatile/pharmacology , Lippia , Bacteria/drug effects , Brazil , Oils, Volatile/chemistry , Cardiovascular System/drug effects , Central Nervous System/drug effects , Monoterpenes/pharmacology , Gastrointestinal Tract/drug effects , Medicine, Traditional
Bol. latinoam. Caribe plantas med. aromát ; 18(1): 58-70, ene. 2019. tab, ilus
Article in English | LILACS | ID: biblio-1007470


The aim of this study was to evaluate the concentration and chemical composition of the essential oil the leaves of basil cultivars and hybrids cultivated in different cropping seasons: dry season and rainy season. The variables evaluated were the content and composition of essential oils in the two seasons. The essential oil content ranged from 0.66% to 3.21% in the dry season and from 0.80% to 4.20% in the rainy season. The major compounds found among the genotypes were linalool, methyl chavicol, neral, geranial, eugenol, and methyl (E)- cinnamate, defining the formation of five groups in each season, classified in the following chemotypes: methyl chavicol (Group 1), citral (neral+geranial) (Group 2), methyl cinnamate (Group 3), linalool (Group 4), and intermediate linalool (Group 5). All the traits evaluated had heritability (h ) greater than 95% and high CVg/CVe ratio values. The cropping season affected the content and chemical compositions of basil essential oil.

El objetivo de este estudio fue evaluar la concentración y composición química del aceite esencial las hojas de cultivares de albahaca e híbridos cultivados en diferentes temporadas de cultivo: estación seca y estación lluviosa. Las variables evaluadas fueron la contenido y la composición de los aceites esenciales en las dos estaciones. La contenido de aceite esencial varió de 0.66% a 3.21% en la estación seca y de 0.80% a 4.20% en la estación lluviosa. Los principales compuestos encontrados entre los genotipos fueron linalool, metilchavicol, neral, geranial, eugenol y metil (E)-cinamato, definiendo la formación de cinco grupos en cada estación, clasificados en los siguientes quimiotipos: metil chavicol (Grupo 1), citral (neral + geranial) (Grupo 2), cinamato de metilo (Grupo 3), linalool (Grupo 4) y linalol intermedio (Grupo 5). Todos los rasgos evaluados mostraron una heredabilidad (h ) mayor que el 95% y altos valores de relación CVg/CVe. La temporada de cultivo afectó la contenido y las composiciones químicas del aceite esencial de albahaca.

Seasons , Oils, Volatile/chemistry , Plant Leaves/chemistry , Ocimum basilicum , Eugenol/analysis , Cinnamates/analysis , Monoterpenes/analysis , Anisoles/analysis
Article in Chinese | WPRIM | ID: wpr-773665


Pistacia lentiscus,which belongs to foreign medicine resources,is widely distributed in the Mediterranean and Middle Eastern area. The essential oils are a mixture of several volatile compounds mainly monoterpenes and sesquiterpenes obtained from different parts of P. lentiscus by hydrodistillation. The variability of chemical composition,biological activities and content of essential oil is strongly affected by extraction technology,environmental and sex factors. It is indicated that essential oils of P. lentiscus have kinds of biological activities such as antibacterial,anticancer,anti-atherogenesis,antioxidant,anti-inflammatory and insecticidal activities.Many scholars hold the opinion that combination of different components with synergistic and/or additive actions should account for their biological activities. Due to its diverse efficacy and special taste,the essential oil of P. lentiscus has been extensively used in medicine,food and cosmetics industries. A mini review of chemical constituents and biological activities of essential oil of P. lentiscus in the past20 years is made here to provide valuable reference for the construction of " the Belt and Road".

Monoterpenes , Chemistry , Pharmacology , Oils, Volatile , Chemistry , Pharmacology , Pistacia , Chemistry , Plant Oils , Chemistry , Pharmacology , Sesquiterpenes , Chemistry , Pharmacology
Article in English | WPRIM | ID: wpr-760559


Marrubium vulgare, plant species belonging to Marrubium genus, is widespread in the Mediterranean areas, introduced elsewhere and also cultivated in many countries. Its oil is recognized to possess a considerable biological activities with varied chemical composition. This paper aims to overview the chemical composition and biological activities of M. vulgare essential oil's considered as a medicinal plant, widely used in folk medicine overall the world. In essential oils of M. vulgare, germacrene D, β-caryophyllene, β-bisabolene, bicyclogermacrene and carvacrol are generally considered as either mains or minor constituents and each species presents its own composition. Sesquiterpenoids were the dominant fraction while monoterpenoids were present in appreciable or in trace amount. Oxygenated fractions dominated in monoterpenes however, hydrocarbon fraction overpowered in sesquiterpenes. These oils are biologically active, they exhibit an antioxidant and antimicrobial activities and other activities. Due to the variability of composition of essential oil, further studies are necessary, particularly regarding their chemical's which may cause an important change in the biological activities of oils and probably defined different chemotype.

Marrubium , Medicine, Traditional , Monoterpenes , Oils , Oils, Volatile , Oxygen , Plants , Plants, Medicinal , Sesquiterpenes
Vitae (Medellín) ; 26(2): 78-83, 2019. Ilustraciones
Article in English | LILACS, COLNAL | ID: biblio-1021402


Background: accumulating evidence suggests that natural compounds and specifically monoterpenes exert a vasodilator action. Objetive: to investigate the vascular effects of isoespintanol (2-isopropil-3,6-dimetoxi-5-metilfenol, ISO) monoterpene isolated from the leaves of Oxandra cf xylopioides. Methods: thoracic aortic rings isolated from Wistar rats were contracted with KCl 80 mM and then relaxed by exposure to Ca2+-free solution in absence and in presence of ISO 0.6 mg/mL. The force/tissue ratio (F/W) and the time to obtain 50% of relaxation (T-50) were used to assess the maximal contractile response and the relaxation, respectively. To examine the participation of NO additional experiments were performed under inhibition of nitric oxide synthase with L-NAME (L-NG-Nitroarginine methyl ester). Results: ISO significantly decreased the F/W ratio (257 ± 19 vs. 360 ± 18) and did not change T-50. In presence of L-NAME the effects of ISO on contractile response was abolished. Conclusions: these results demonstrate that ISO exerts a vasodilator effect through NO-dependent pathways and suggest that an inhibition of calcium influx could be the involved mechanism

Antecedentes: la evidencia acumulada sugiere que los compuestos naturales, especialmente monoterpenos, ejercen una acción vasodilatadora. Objetivo: investigar los efectos vasculares del monoterpeno isoespintanol (2-isopropil-3,6-dimetoxi-5-metilfenol, ISO) aislado de hojas de Oxandra cf xylopioides. Métodos: anillos de aorta torácica aislados de ratas Wistar fueron contraídas con cloruro de potasio 80 mM y luego relajadas por exposición a una solución libre de Ca2+ en ausencia y presencia de isoespintanol 0,6 µg/mL. El radio fuerza/tejido (F/T) y el tiempo para obtener 50% de relajación (T50) se usaron para lograr la máxima respuesta contráctil y de relajación, respectivamente. Para evaluar la participación del óxido nítrico, se realizaron experimentos adicionales bajo la inhibición de la óxido nítrico sintetasa con L-NAME (L-NG-éster metílico de nitroarginina). Resultados: Isoespintanol disminuyó el radio F/W significativamente (257 ± 19 vs. 360 ± 18) y no cambió T-50. En presencia de L-NAME, los efectos del isoespintanol en la respuesta contráctil fueron suprimidos. Conclusiones: Estos resultados demuestran que el isoespintanol ejerce un efecto vasodilatador a través de vías NO dependientes y sugiere que la inhibición de la entrada de calcio puede ser el mecanismo involucrado.

Humans , Vasodilation , Monoterpenes , Aorta, Thoracic , Nitric Oxide
Bol. latinoam. Caribe plantas med. aromát ; 17(6): 604-609, nov. 2018. tab
Article in English | LILACS | ID: biblio-1007366


This study describes the qualitative and quantitative seasonal analysis of the essential oils from an unexplored plant Eugenia brevistyla, native from Brazilian Atlantic Rain Forest and Semidecidual Forest. Analysis by GC-FID and GC-MS allowed the identification of 28 compounds. The largest fraction corresponds to oxygenated sesquiterpenes in all seasons. The major compound was E-nerolidol in all seasons, being higher in winter (83.14%) and lower in spring (69.6%). The second major compound was byciclogermacrene in the spring and in the summer essential oils. Alloaromadendrene and spathulenol were the second major compounds in autumn and winter, respectively. Sesquiterpenes hydrocarbons showed higher variation along the year (58%) than oxygenated sesquiterpenes (2%). No monoterpenes were found in the analyzed essential oils.

Este estudio describe el análisis estacional cualitativo y cuantitativo del aceite esencial de la planta inexplorada Eugenia brevistyla, nativa de la Selva Tropical Atlántica dey del Bosque Semidecidual de Brasil. El análisis por GC-FID y GC-MS permitió la identificación de 28 compuestos. La fracción más grande corresponde a sesquiterpenos oxigenados en todas las estaciones. El compuesto principal fue E-nerolidol en todas las estaciones, siendo más alto en invierno (83.14%) y más bajo en la primavera (69.6%). El segundo compuesto principal fue biciclogermacreno en los aceites esenciales de la primavera y del verano. El aloaromadendreno y el espatulenol fueron los segundos compuestos principales en otoño e invierno, respectivamente. Los hidrocarburos sesquiterpénicos mostraron una mayor variación a lo largo del año (58%) que los sesquiterpenos oxigenados (2%). No se encontraron monoterpenos en los aceites esenciales analizados.

Seasons , Oils, Volatile/chemistry , Eugenia , Sesquiterpenes/analysis , Brazil , Plant Leaves/chemistry , Monoterpenes/analysis , Flame Ionization , Gas Chromatography-Mass Spectrometry
Braz. j. biol ; 78(4): 691-696, Nov. 2018. tab
Article in English | LILACS | ID: biblio-951593


Abstract This study aimed to evaluate the in vitro antibacterial activity of the phytochemicals thymol, linalool, and citronellol against Streptococcus mutans, Streptococcus salivarius and Streptococcus oralis. Disk diffusion screening on solid medium and measurement of the diameter of the bacterial growth inhibition halos was the technique utilized. The Minimum Inhibitory Concentration (MIC) of the substances was determined using serial substance dilutions and microdilution technique in Brain Heart Infusion culture medium. After incubation for 24 hours in an oven at 37 °C, plate reading was completed and confirmed by visual method using 2,3,5 triphenyl tetrazolium chloride dye. The Minimum Bactericidal Concentration (MBC) was determined from MIC subcultures. Assays were performed in triplicate, and chlorhexidine was used as a positive control. The diameters in mm of the growth inhibition halos ranged between 7.3 and 10.7 for S. mutans, 7.3 and 10.0 for S. oralis, and 8.2 and 9.8 for S. salivarius. The MIC and MBC values obtained converged, ranging from maximum values in the presence of Linalool (1,250.0 mg/mL, 2,500.0 mg/mL and 2,500.0 mg/mL, respectively, for S. mutans, S. oralis, and S. salivarius); and minimum values with Thymol (312.5 μg/ml, 156.2 μg/mL and 156.2 μg/ml, respectively for S. mutans, S. oralis, and S. salivarius). All the tested phytochemicals displayed antibacterial activity, thus representing substances with potential applications in preventing tooth decay.

Resumo Este estudo objetivou avaliar a atividade antibacteriana in vitro dos fitoquímicos timol, linalol e citronelol sobre Streptococcus mutans, Streptococcus salivaris e Streptococcus oralis. Utilizou-se a técnica de discos de difusão em meio sólido e medição do diâmetro dos halos de inibição. A concentração inibitória mínima (CIM) das substâncias foi determinada utilizando diluições em série das substâncias e técnica de microdiluição em meio de cultura de Brain Heart Infusion. Após incubação durante 24 horas em estufa a 37 °C, a leitura da placa foi confirmada pelo método visual usando o corante 2,3,5 trifenil cloreto de tetrazólio. A concentração bactericida mínima (CBM) foi determinada a partir de subculturas de MIC. Os ensaios foram realizados em triplicata, e clorexidina foi usada como um controle positivo. Os diâmetros dos halos de inibição do crescimento variaram entre 7,3 e 10,7 por S. mutans, 7,3 e 10,0 por S. oralis, e 8,2 e 9,8 para S. salivaris. Os valores de CIM e CBM obtidos variaram de valores máximos na presença de linalol (1.250,0 mg/mL, 2.500.0 mg/mL e 2.500.0 mg/mL, respectivamente, para o S. mutans, S oralis e S. salivaris); a valores mínimos com timol (312,5 μg/ml, 156,2 μg/mL e 156,2 μg/ml, respectivamente para S. mutans, S. oralis e S. salivaris). Todos os fitoquímicos testados apresentaram atividade antibacteriana, representando, assim, substâncias com potencial de aplicações na prevenção da cárie dentária.

Streptococcus/drug effects , Thymol/pharmacology , Monoterpenes/pharmacology , Anti-Bacterial Agents/pharmacology , Microbial Sensitivity Tests/methods , Dental Caries/microbiology , Phytochemicals/pharmacology , Acyclic Monoterpenes
Biosci. j. (Online) ; 34(5): 1200-1209, sept./oct. 2018.
Article in English | LILACS | ID: biblio-967307


The present study evaluated the antifungal activity of the essential oils of chemotypes of Myrcia lundiana and their major compounds on the fungi Fusarium pallidoroseum, Fusarium solani, and Colletotrichum musae. The essential oils were obtained by hydrodistillation and analyzed by GCMS/FID. For the evaluation of the antifungal activity, the essential oils and the major compounds were tested at the concentration of 0.1 mL/L until the fungicidal effect was detected. The major compounds detected in the essential oil were 1,8-cineole, isopulegol, and citral. The chemotypes (MLU-005 and MLU-019) provided 100% mycelial growth inhibition for the fungus F. pallidoroseum from the concentration of 1.1 mL/L (minimum inhibition concentration - MIC). For chemotype (MLU-022), the minimum fungicidal concentration (MFC) was 0.3 mL/L. For F. solani, the essential oils of the chemotypes (MLU-005 and MLU-019) presented MIC at concentrations of 7.0 and 5.0 mL/L, respectively. The essential oil of the chemotype (MLU-022) presented MFC of 0.6 mL/L. Different MIC was observed for the three studied chemotypes for the fungus C. musae, ranging between 0.4 mL/L, for the chemotype (MLU-005); 0.5 mL/L, for the chemotype (MLU-022); and 0.7 mL/L, for the chemotype (MLU-019). The best MFC was observed for the chemotype (MLU-005) (0.5 mL/L). The major compounds tested separately presented better MIC values when compared with their chemotypes, except for the compound 1,8-cineole, which presented lower mycelial growth inhibition for the three fungi tested, suggesting that the chemical profile or the presence of some other compound of the essential oil may inhibit the growth of the three fungi studied. The compound isopulegol provided lower MFC for the fungus C. musae (0.4517 mL/L) when compared with the fungi F. pallidoroseum and F. solani, (MFC of 0.4927 mL/L). The compound citral provided a lower MFC on the fungus C. musae (0.1668 mL/L) in relation to the other fungi tested. The essential oils of the chemotypes of M. lundiana and their major compounds showed potential to control the studied phytopathogens and can be an alternative for agriculture for presenting an inhibitory and fungicidal effect against these organisms at lower concentrations.

O presente trabalho avaliou a atividade antifúngica de óleos essenciais de quimiotipos de Myrcia lundiana dos seus compostos majoritários sobre os fungos Fusarium pallidoroseum, Fusarium solani e Colletotrichum musae. Os óleos essenciais foram obtidos por hidrodestilação e analisados por CGEM/DIC. Para avaliação da atividade antifúngica, foram testados os óleos essenciais e os compostos majoritários na concentração de 0,1 mL/L até encontrar o efeito fungicida. Os principais compostos presentes no óleo essencial foram 1,8-cineol, isopulegol e citral. Os quimiotipos (MLU-005 e MLU-019) proporcionaram 100% de inibição do crescimento micelial para o fungo F. pallidoroseum a partir da concentração de 1,1 mL/L (Concentração Inibitória Mínima ­ CIM). Para o quimiotipo (MLU-022), a melhor concentração fungicida mínima (CFM) foi de 0,3 mL/L. Para F. solani, os óleos essenciais dos quimiotipos (MLU-005 e MLU-019) apresentaram CIM nas concentrações de 7,0 e 5,0 mL/L, respectivamente. O óleo essencial do quimiotipo (MLU-022) apresentou CFM de 0,6 mL/L. Observou-se CIM diferenciado para os três quimiotipos estudados para o fungo C. musae, variando entre 0,4 mL/L, para o quimiotipo (MLU-005); 0,5 mL/L, para o quimiotipo (MLU-022); e 0,7 mL/L, para o quimiotipo (MLU-019). O quimiotipo MLU-005 apresentou o melhor CFM, 0,5 mL/L. Os compostos majoritários testados separadamente apresentaram melhores valores de CIM frente aos seus quimiotipos, exceto o composto 1,8-cineol, que apresentou menor inibição do crescimento micelial para os três fungos testados, sugerindo que o perfil químico ou a presença de algum outro composto no óleo essencial pode estar atuando na inibição do crescimento dos três fungos estudados. O composto isopulegol proporcionou menor CFM para o fungo C. musae (0,4517 mL/L) em relação aos fungos F. pallidoroseum e F. solani, para os quais apresentou CFM de 0,4927 mL/L. O composto citral proporcionou um menor CFM sobre o fungo C. musae (0,1668 mL/L), em relação aos demais fungos testados. Os óleos essenciais de quimiotipos de M. lundiana e seus compostos majoritários apresentaram potencial para o controle dos fitopatógenos estudados, podendo ser considerados como uma alternativa para a agricultura, uma vez que em concentrações mais baixas apresentaram efeito inibitório e fungicida frente a estes organismos.

Oils, Volatile , Colletotrichum , Myrtaceae , Monoterpenes , Fungi , Fusarium