RESUMO
Ferula ovina (Boiss.) Boiss is one of the most important endemic medicinal plants in Iran, which has three main terpenoid compounds including ferutinin, stylosin and tschimgine. Ferutinin is the strongest natural phytoestrogen that has agonistic activity on estrogen receptors, particularly α-receptors. To determine the amount of ferutinin in F. ovina roots, we firstly used HPLC-UV method. In the HPLC method, the resolution of ferutinin from the two other compounds, stylosin and tshimgine, was poor. Therefore, we decided to use qHNMR method for simultaneous quantification of ferutinin, stylosin and tshimgine in the plant roots. Quantitative 1H-NMR (qHNMR) was carried out based on the relative ratio of signal integration of each compound [(H-1 for tschimgine (δH 4.94-5.03), OCH3 for stylosin (δH 3.8), and H-9 for ferutinin (δH 5.58)] to certain amount of the internal standard dimethyl sulfone (DMSO2). The qHNMR method showed good precision (intra-day RSD ≤ 2.31%, inter-day RSD ≤ 2.72%), linearity (in the ranges of 1.3-10.41, 1.2-9.7 and 1.1-9.02 mg/mL with correlation coefficients at 0.9991), repeatability (RSD ≤ 2.99%) and stability (RSD ≤ 2.4%) for the quantification of the compounds. This work confirmed that qHNMR represents a feasible alternative to high-performance liquid chromatography based methods for simultaneous quantification of ingredients in plant extracts.
Assuntos
Ferula/química , Extratos Vegetais/química , Espectroscopia de Prótons por Ressonância Magnética/métodos , Benzoatos/análise , Compostos Bicíclicos com Pontes/análise , Cicloeptanos/análise , Composição de Medicamentos/normas , Estudos de Viabilidade , Hidroxibenzoatos/análise , Monoterpenos/análise , Extratos Vegetais/normas , Raízes de Plantas/química , Controle de Qualidade , Sesquiterpenos/análiseRESUMO
In the present study, the chemical composition of the essential oil from the aerial parts of Anthemis secundiramea Biv. subsp. secundiramea L. collected in Sicily was evaluated by GC and gas chromatography-mass spectrometry. The main components of A. secundiramea were (Z)-lyratyl acetate (14.6%), (Z)-chrysanthenyl acetate (9.9%), (Z)-chrysanthenol (8.7%) and (E)-chrysanthenyl acetate (7.7%). The comparing with other studied oils of genus Anthemis belonging to the same clade is discussed. Antibacterial and antifungal activities against some micro-organisms infesting historical art craft, were also determined.
Assuntos
Anthemis/química , Óleos Voláteis/química , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Arte , Asteraceae/química , Compostos Bicíclicos com Pontes/análise , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/análise , Óleos de Plantas/química , SicíliaRESUMO
AIMS: The study was focused on the evaluation of antimicrobial activity in vitro of the essential oil (EO) of leaves from Schinus molle against bacteria and fungi of clinical importance in the search for the discovery of new active compounds. METHODS AND RESULTS: The chemical composition of the S. molle EO was determined by gas chromatography/mass spectrometry and its antimicrobial effect was verified by broth microdilution method. The major compounds found were ß-pinene (25·23%), epi-α-cadinol (21·29%), α-pinene (18·72%), myrcene (11·54%) and sabinene (5·02%). The EO showed significant antifungal activity against Paracoccidioides brasiliensis (39·06 µg ml-1 ), weak action against Cryptococcus neoformans (625 µg ml-1 ) and Trichophyton quinckeanum (625 µg ml-1 ) and was inactive against Candida sp. In the analysis of the antibacterial action, the micro-organisms tested did not show sensitivity. CONCLUSIONS: This study showed a promising result of S. molle volatiles against the fungus P. brasiliensis, which causes paracoccidioidomycosis (PCM), a systemic mycosis of great clinical importance in Latin America. SIGNIFICANCE AND IMPACT OF THE STUDY: The results found here are novel and encourage investigations of the compounds present in this EO, which represents a source of molecules with potential use in the treatment of PCM.
Assuntos
Anacardiaceae/química , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Óleos Voláteis/farmacologia , Óleos de Plantas/farmacologia , Monoterpenos Acíclicos , Alcenos/análise , Antibacterianos/química , Antifúngicos/química , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Cryptococcus neoformans/efeitos dos fármacos , Monoterpenos/análise , Óleos Voláteis/química , Paracoccidioides/efeitos dos fármacos , Folhas de Planta/química , Óleos de Plantas/química , Terpenos/análise , Trichophyton/efeitos dos fármacosRESUMO
The growing demand and commercial value of black pepper (Piper nigrum) has resulted in considerable interest in developing suitable and cost-effective methods for chemical characterization and quality evaluation purposes. In the current study, an extensive set of oil samples (n = 23) that were extracted by steam distillation from black pepper seeds was investigated to compare the chemical profiles of samples originating from nine major producing countries, as well as to identify potential chemical markers for quality evaluation. The twenty-two most abundant volatile compounds, mainly terpenes, in these oils were determined by conventional GC/MS analysis. Principal component analysis with this set of data revealed distinct clusters for samples that originated from China and Malaysia. Relatively low concentrations of sabinene (< 0.2%) and high concentrations of 3-carene (10.9â-â21.1%) were observed in these samples, respectively, compared to oil samples from other countries. The enantiomeric distributions of key terpene markers, viz., ß-pinene, sabinene, limonene, and terpinen-4-ol, were determined by chiral GC/MS analysis. Interestingly, for these four monoterpenes, levo-isomers were found to be predominant, emphasizing the highly conserved enzymatic processes occurring in P. nigrum. Moreover, consistent enantiomeric ratios ((-) isomer/(+) isomer) of 92.2 ± 3.0% for ß-pinene, 94.8 ± 2.8% for sabinene, 60.7 ± 1.1% for limonene, and 78.3 ± 1.3% for terpinen-4-ol were observed, independent of geographical location. These results demonstrate the potential of using stereospecific compositions as chiral signatures for establishing the authenticity and quality of black pepper oil.
Assuntos
Piper nigrum/química , Óleos de Plantas/química , Terpenos/análise , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Cromatografia Gasosa-Espectrometria de Massas , Limoneno/análise , Monoterpenos/análise , Óleos de Plantas/normas , EstereoisomerismoRESUMO
The chemical constituents identified in the essential oils hydrodistilled from the leaves of Amomum gagnepainii T.L.Wu, K.Larsen and Turland and Amomum repoense Pierre ex Gagnep (Zingiberaceae) of Vietnam origin are reported. The chemical analyses were performed by means of gas chromatography-flame ionisation detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC-MS). The main compounds of A. gagnepainii were farnesyl acetate (18.5%), zerumbone (16.4%) and ß-caryophyllene (10.5%). On the other hand, Amomum repoense comprised of monoterpenes dominated by ß-pinene (33.5%), (E)-ß-ocimene (9.6%), γ-terpinene (9.1%) and α-pinene (8.4%). This is the first report on the essential oils of A. gagnepainii and A. repoense grown in Vietnam or elsewhere.
Assuntos
Amomum/química , Óleos Voláteis/análise , Folhas de Planta/química , Óleos de Plantas/análise , Terpenos/análise , Monoterpenos Acíclicos , Alcenos/análise , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Monoterpenos Cicloexânicos , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/análise , Óleos Voláteis/química , Óleos de Plantas/química , Sesquiterpenos Policíclicos , Sesquiterpenos/análise , Vietnã , ZingiberaceaeRESUMO
The leafminer Tuta absoluta Meyrick (Lepidoptera: Gelechiidae) is one of the most important pests of tomato, reducing crop yields by up to 100% in greenhouses and fields, in several countries globally. Because synthetic insecticides lead to resistance and have adverse effects on natural enemies and the health of producers, alternative control methods are needed. In this study, we assessed the oviposition-deterring effect of basil plants, Ocimum gratissimum L. and O. basilicum L. (Lamiaceae), using dual-choice behavioural assays performed in flight tunnels. We found that both plants significantly reduced T. absoluta oviposition behaviour on a tomato plant located nearby. To evaluate the potential effect of basil volatile organic compounds, we formulated essential oils of both plant species in paraffin oil, and observed a similar oviposition-deterring effect. Gas chromatography analyses detected 18 constituents in these essential oils which the major constituents included thymol (33.3%), p-cymene (20.4%), γ-terpinene (16.9%), myrcene (3.9%) in O. gratissimum and estragol (73.8%), linalool (8.6%), ß-elemene (2.9%) and E-ß-ocimene (2.6%) in O. basilicum. Twenty and 33 compounds were identified of the volatiles collected on O. gratissimum and O. basilicum plants, respectively. The main components include the following: p-cymene (33.5%), γ-terpinene (23.6%), α-terpinene (7.2%), α-thujene (6.7%) and E-α-bergamotene (38.9%) in O. gratissimum, and methyl eugenol (26.1%), E-ß-ocimene (17.7%), and linalool (9.4%) in O. basilicum. Four compounds (α-pinene, ß-pinene, Myrcene, Limonene) were common in essential oils and plants. Our results suggest the valuable potential of basil and associated essential oils as a component of integrated management strategies against the tomato leafminer.
Assuntos
Lepidópteros/efeitos dos fármacos , Ocimum/química , Óleos Voláteis/farmacologia , Oviposição/efeitos dos fármacos , Extratos Vegetais/farmacologia , Óleos de Plantas/farmacologia , Monoterpenos Acíclicos , Alcenos/análise , Alcenos/farmacologia , Animais , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/farmacologia , Monoterpenos Cicloexânicos , Cimenos , Feminino , Lepidópteros/fisiologia , Monoterpenos/análise , Monoterpenos/farmacologia , Óleos Voláteis/química , Extratos Vegetais/análise , Óleos de Plantas/química , Compostos Orgânicos Voláteis/química , Compostos Orgânicos Voláteis/farmacologiaRESUMO
The chemical composition, including the enantiomeric excess of the main terpenes, of essential oils from seeds and cones of Abies concolor was studied by chromatographic (GC) and spectroscopic methods (mass spectrometry, nuclear magnetic resonance), leading to the determination of 98 compounds. Essential oils were mainly composed of monoterpene hydrocarbons. The dominant volatiles of seed essential oil were: limonene (47 g/100 g, almost pure levorotary form) and α-pinene (40 g/100 g), while α-pinene (58 g/100 g), sabinene (11 g/100 g), and ß-pinene (4.5 g/100 g) were the predominant components of the cone oil. The seed and cone essential oils exhibited mild antibacterial activity, and the MIC ranged from 26 to 30 µL/mL against all of the tested bacterial standard strains: Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium, Escherichia coli, and Klebsiella pneumoniae. The cytotoxic studies have demonstrated that tested essential oils were cytotoxic to human skin fibroblasts and human microvascular endothelial cells at concentrations much lower than the MIC. The essential oils from A. concolor seeds and cones had no toxic effect on human skin fibroblasts and human microvascular endothelial cells, when added to the cells at a low concentration (0-0.075 µL/mL) and (0-1.0 µL/mL), respectively, and cultured for 24 h.
Assuntos
Abies/química , Antibacterianos/farmacologia , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Sementes/química , Antibacterianos/química , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Sobrevivência Celular/efeitos dos fármacos , Cicloexenos/análise , Avaliação Pré-Clínica de Medicamentos , Fibroblastos/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Limoneno , Testes de Sensibilidade Microbiana , Monoterpenos/análise , Óleos Voláteis/análise , Terpenos/análiseRESUMO
Ferula hermonis, a well-known species of the genus Ferula found in Lebanon and Syria, has a brilliant history in traditional medicine as it has been used for the treatment of erectile dysfunction in men and menopausal disturbances in women. Thanks to modern pharmacological and clinical investigations, F. hermonis is a valuable medicinal and condimental plant that may be used for the treatment of impotence and diabetes, the prevention of osteoporosis, and possesses anti-microbial and anti-inflammatory properties. Phytochemical investigations have shown that this plant contains daucane aryl esters such as ferutinin, which has exhibited various biological activities including hypoglycemic and estrogenic activities. Ferutinin is one of the strongest natural phytoestrogen which has agonistic activity on estrogen receptors, particularly α receptor. It seems that ferutinin and its derivatives play an important role in F. hermonis biological activities, mainly the beneficial effects of this plant on impotence, diabetes and osteoporosis. The present review discusses the available data on the active constituents and biological activities of F. hermonis and their possible underlying mechanisms of action.
Assuntos
Ferula/química , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Benzoatos/análise , Benzoatos/farmacologia , Benzoatos/uso terapêutico , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/farmacologia , Compostos Bicíclicos com Pontes/uso terapêutico , Cicloeptanos/análise , Cicloeptanos/farmacologia , Cicloeptanos/uso terapêutico , Humanos , Raízes de Plantas/química , Sesquiterpenos/análise , Sesquiterpenos/farmacologia , Sesquiterpenos/uso terapêuticoRESUMO
The chemical composition of the essential oils isolated from the aerial parts of Anthemis arvensis L. subsp. arvensis, Anthemis cretica subsp. messanensis (Brullo) Giardina & Raimondo and from flowers and leaves of Anthemis cretica subsp. columnae (Ten.) Frezén were determinated by GC-FID and GC-MS analyses. Torreyol (85.4%) was recognised as the main constituent of the Anthemis arvensis subsp. arvensis essential oil, while in the essential oils of Anthemis cretica subsp. messanensis, collected on the rock and cultivated in Hortus Botanicus Panormitanus, (E)-chrysanthenyl acetate (28.8 and 24.2% resp.), 14-hydroxy-α-humulene (8.1 and 5.3% resp.), santolina triene (8 and 5.8% resp.) and α-pinene (6.7 and 5.4% resp.) prevailed. 18-cineole (13.3 and 12.2% resp.), was the main component of both flower and leaf oils of Anthemis cretica subsp. columnae together with δ-cadinene (9.0 and 8.2% resp.) and (E)-caryophyllene (8.3 and 5.6% resp.).
Assuntos
Anthemis/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Óleos Voláteis/química , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Cicloexanóis/análise , Avaliação Pré-Clínica de Medicamentos/métodos , Eucaliptol , Flores/química , Cromatografia Gasosa-Espectrometria de Massas , Testes de Sensibilidade Microbiana , Monoterpenos/análise , Óleos Voláteis/análise , Folhas de Planta/química , Sesquiterpenos Policíclicos , Sesquiterpenos/análise , SicíliaRESUMO
Plant specialised metabolites like essential oils are highly variable depending on genetic and various ecological factors. The aim of the present work was to characterise essential oils of the species Seseli rigidum Waldst. & Kit. (Apiaceae) in various organs on the individual and populational levels. Geographical variability and the impact of climate and soil type on essential oil composition were also investigated. Individually sampled essential oils of roots, aerial parts and fruits of plants from seven populations were analysed by GC-FID and GC-MS. The investigated populations showed high interpopulational and especially intrapopulational variability of essential oil composition. In regard to the variability of essential oils, different chemotypes were defined. The essential oils of S. rigidum roots represented a falcarinol chemotype, oils of aerial parts constituted an α-pinene or α-pinene/sabinene chemotype and fruit essential oils can be characterised as belonging to a complex sabinene/α-pinene/ß-phellandrene/falcarinol/germacrene B chemotype. At the species level, analysis of variance (ANOVA), principal component analysis (PCA) and canonical discriminant analysis (CDA) showed that the plant part exerted the strongest influence on the composition of essential oils. Climate had a high impact on composition of the essential oils of roots, aerial parts and fruits, while influence of the substrate was less pronounced. The variations in main compounds of essential oils based on climate or substrate were complex and specific to the plant part.
Assuntos
Apiaceae/química , Óleos Voláteis/química , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Monoterpenos Cicloexânicos , Cicloexenos/análise , Frutas/química , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/análise , Componentes Aéreos da Planta/química , Óleos de Plantas/química , Raízes de Plantas/químicaRESUMO
The compositions of the essential oils obtained from leaves and stems of Gynura bicolor DC. were analyzed by GC-MS. One hundred eight components of these oils were identified. (E)-ß-caryophyllene (31.42 %), α-pinene (17.11 %), and bicyclogermacrene (8.09 %) were found to be the main components of the leaf oil, while α-pinene (61.42 %), ß-pinene (14.39 %), and myrcene (5.10 %) were the major constituents of the stem oil. We found 73 previously unidentified components in these oils from G. bicolor. The oils were also subjected to odor evaluation. Eleven and 12 aroma-active compounds were detected in the leaf and stem oils, respectively. The abilities of these oils to inhibit acetylcholinesterase (AChE) activity were determined. The sesquiterpenoids in the oils were found to inhibit AChE activity more strongly than the monoterpenoids in the oils did. It was suggested that the three main components in each essential oil act synergistically against AChE activity. These results show that the essential oils obtained from G. bicolor are a good dietary source of AChE activity inhibition.
Assuntos
Acetilcolinesterase/metabolismo , Asteraceae/química , Inibidores da Colinesterase/farmacologia , Odorantes/análise , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Monoterpenos Acíclicos , Alcenos/análise , Alcenos/farmacologia , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/farmacologia , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Monoterpenos/análise , Monoterpenos/farmacologia , Óleos Voláteis/química , Extratos Vegetais/química , Folhas de Planta/química , Caules de Planta/química , Sesquiterpenos Policíclicos , Sesquiterpenos/análise , Sesquiterpenos/farmacologiaRESUMO
Essential oil of the aerial parts of Allium neapolitanum Cirillo collected in Sicily were analyzed by gas-chromatography-flame-ionization detection and gas-chromatography-mass spectrometry. Nineteen compounds were identified in the oil and the main components were found to be (E)-chrysanthenyl acetate (28.1%), (Z)-chrysanthenyl acetate (23.8%), (E)-ß-farnesene (9.6%), dimethyl trisulfide (9.6%), camphor (7.4%), methyl allyl disulfide (6.8%) and 1-methyl-3-allyl trisulfide (5.8%). The essential oil showed good antimicrobial activity against 11 strains of test microorganisms, including several species infesting historical material.
Assuntos
Allium/química , Arte , Bactérias/efeitos dos fármacos , Compostos Bicíclicos com Pontes/isolamento & purificação , Compostos Bicíclicos com Pontes/farmacologia , Fungos/efeitos dos fármacos , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Óleos de Plantas/química , Óleos de Plantas/farmacologia , Sesquiterpenos/isolamento & purificação , Sulfetos/isolamento & purificação , Sulfetos/farmacologia , Compostos Alílicos/análise , Compostos Alílicos/isolamento & purificação , Compostos Alílicos/farmacologia , Artefatos , Compostos Bicíclicos com Pontes/análise , Cânfora/análise , Cânfora/isolamento & purificação , Cânfora/farmacologia , Dissulfetos/análise , Dissulfetos/isolamento & purificação , Dissulfetos/farmacologia , Farmacorresistência Bacteriana , Farmacorresistência Fúngica , Ionização de Chama , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/análise , Óleos Voláteis/isolamento & purificação , Componentes Aéreos da Planta/química , Óleos de Plantas/isolamento & purificação , Sesquiterpenos/análise , Sesquiterpenos/farmacologia , Sicília , Sulfetos/análiseRESUMO
Amomum maximum Roxb. is a perennial herb distributed in South China and Southeast Asia. The objective of this work was to analyze the chemical constituents and assess insecticidal and repellent activities of the essential oil from Amomum maximum fruits against Tribolium castaneum (Herbst) and Liposcelis bostrychophila (Badonnel). The essential oil was obtained by hydrodistillation and analyzed by gas chromatography-flame ionization detector and gas chromatography-mass spectrometry. The main components of the essential oil were identified to be ß-pinene (23.39%), ß-caryophyllene (16.43%), α-pinene (7.55%), sylvestrene (6.61%) and ç-cadinene (4.19%). It was found that the essential oil of A. maximum fruits possessed contact and fumigant toxicities against T. castaneum adults (LD50 = 29.57 µg/adult and LC(50) = 23.09 mg/L air, respectively) and showed contact toxicity against L. bostrychophila (LD(50) = 67.46 µg/cm(2)). Repellency of the crude oil was also evaluated. After 2 h treatment, the essential oil possessed 100% repellency at 78.63 nL/cm(2) against T. castaneum and 84% repellency at 63.17 nL/cm(2) against L. bostrychophila. The results indicated that the essential oil of A. maximum fruits had the potential to be developed as a natural insecticide and repellent for control of T. castaneum and L. bostrychophila.
Assuntos
Amomum/química , Repelentes de Insetos , Inseticidas , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Óleos de Plantas/isolamento & purificação , Óleos de Plantas/farmacologia , Tribolium/efeitos dos fármacos , Animais , Sudeste Asiático , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/isolamento & purificação , Compostos Bicíclicos com Pontes/farmacologia , Compostos Bicíclicos com Pontes/toxicidade , China , Destilação/métodos , Ionização de Chama/métodos , Frutas/química , Fumigação , Cromatografia Gasosa-Espectrometria de Massas , Dose Letal Mediana , Monoterpenos/análise , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Monoterpenos/toxicidade , Óleos Voláteis/análise , Óleos Voláteis/toxicidade , Óleos de Plantas/análise , Óleos de Plantas/toxicidade , Sesquiterpenos Policíclicos , Sesquiterpenos/análise , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Sesquiterpenos/toxicidadeRESUMO
Baccharis is a widespread genus belonging to the Asteraceae family that includes almost 400 species exclusively from the Americas. Even when studied in detail, the taxonomic classification among species from this genus is not yet fully defined. Within the framework of our study of the volatile composition of the Baccharis genus, four species (B. trimera, B. milleflora, B. tridentata, and B. uncinella) were collected from the 'Campos de Cima da Serra' highlands of the Brazilian state of Rio Grande do Sul. The aerial parts were dried and extracted by the simultaneous distillation extraction (SDE) procedure. This is the first time that SDE has been applied to obtain and compare the volatile-extract composition in the Baccharis genus. Characterization of the volatile extracts allowed the identification of 180 peaks with many coeluting components; these latter being detailed for the first time for this genus. The multivariate statistical analyses allowed separating the volatile extracts of the four populations of Baccharis into two separate groups. The first one included the B. milleflora, B. trimera, and B. uncinella volatile extracts. The three species showed a high degree of similarity in their volatile composition, which was characterized by the presence of high contents of sesquiterpene compounds, in particular of spathulenol. The second group comprised the extract of B. tridentata, which contained α-pinene, ß-pinene, limonene, and (E)-ß-ocimene in high amounts.
Assuntos
Baccharis/química , Odorantes/análise , Extratos Vegetais/química , Compostos Orgânicos Voláteis/análise , Monoterpenos Acíclicos , Alcenos/análise , Alcenos/isolamento & purificação , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/isolamento & purificação , Análise por Conglomerados , Cicloexenos/análise , Cicloexenos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Limoneno , Monoterpenos/análise , Monoterpenos/isolamento & purificação , Análise de Componente Principal , Terpenos/análise , Terpenos/isolamento & purificação , Compostos Orgânicos Voláteis/isolamento & purificaçãoRESUMO
The Baccharis genus has more than 400 species of aromatic plants. However, only approximately 50 species have been studied in oil composition to date. From these studies, very few take into consideration differences between male and female plants, which is a significant and distinctive factor in Baccharis in the Asteraceae family. Baccharis articulata is a common shrub that grows wild in south Brazil, northern and central Argentina, Bolivia, Paraguay and Uruguay. It is considered to be a medicinal plant and is employed in traditional medicine. We report B. articulata male and female volatile composition obtained by simultaneous distillation-extraction technique and analyzed by gas chromatography with mass spectrometry. Also, an assessment of aromatic differences between volatile extracts was evaluated by gas chromatography with olfactometry. The results show a very similar chemical composition between male and female extracts, with a high proportion of terpene compounds of which ß-pinene, limonene and germacrene D are the main components. Despite the chemical similarity, great differences in aromatic profile were found: male plant samples exhibited the strongest odorants in number and intensity of aromatic attributes. These differences explain field observations which indicate differences between male and female flower aroma, and might be of ecological significance in the attraction of pollinating insects.
Assuntos
Baccharis/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Olfatometria/métodos , Extratos Vegetais/análise , Baccharis/fisiologia , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Cromatografia em Camada Fina , Cicloexenos/análise , Destilação , Limoneno , Monoterpenos/análise , Odorantes/análise , Óleos Voláteis/análise , Plantas Medicinais/química , Plantas Medicinais/fisiologia , Sesquiterpenos de Germacrano/análise , Temperatura , Terpenos/análise , Compostos Orgânicos Voláteis/análiseRESUMO
BACKGROUND: Cancer has become a global public health problem and the search for new control measures is urgent. Investigation of plant products such as essential oils from Monodora myristica, Xylopia aethiopica and Xylopia parviflora might lead to new anticancer therapy. In this study, we have investigated the antineoplastic activity of essential oils from fruits of these plants growing in Chad and Cameroon. METHODS: The essential oils obtained by hydrodistillation of fruits of Monodora myristica, Xylopia aethiopica and Xylopia parviflora collected in Chad and Cameroon were analyzed by GC-FID and GC-MS and investigated for their antiproliferative activity against the breast cancer cell line (MCF7). RESULTS: Overall, monoterpenes were mostly found in the six essential oils. Oils from X. aethiopica and X. parviflora from Chad and Cameroon mainly contain ß-pinene at 24.6%, 28.2%, 35.7% and 32.9% respectively. Monodora myristica oils from both origins contain mainly α-phellandrene at 52.7% and 67.1% respectively. The plant origin did not significantly influence the chemical composition of oils. The six essential oils exerted cytotoxic activity against cancer (MCF-7) and normal cell lines (ARPE-19), with more pronounced effect on neoplastic cells in the majority of cases. The highest selectivity was obtained with the essential oils of X. parviflora from Chad and Cameroon (5.87 and 5.54) which were more cytotoxic against MCF-7 than against normal cell line (ARPE-19) with IC50 values of 0.155 µL/mL and 0.166 µL/mL respectively. CONCLUSIONS: Essential oils from fruits of Monodora myristica, Xylopia aethiopica and Xylopia parviflora have shown acceptable antineoplastic potency, and might be investigated further in this regard.
Assuntos
Annonaceae/química , Antineoplásicos Fitogênicos/uso terapêutico , Neoplasias da Mama/tratamento farmacológico , Óleos Voláteis/uso terapêutico , Fitoterapia , Extratos Vegetais/uso terapêutico , Xylopia/química , Antineoplásicos Fitogênicos/análise , Antineoplásicos Fitogênicos/farmacologia , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/farmacologia , Compostos Bicíclicos com Pontes/uso terapêutico , Camarões , Linhagem Celular , Chade , Monoterpenos Cicloexânicos , Frutas , Humanos , Células MCF-7 , Monoterpenos/análise , Monoterpenos/farmacologia , Monoterpenos/uso terapêutico , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologiaRESUMO
The essential oil of different parts of Senecio graciliflorus DC was obtained by hydrodistillation and analysed by GC-FID and GC-MS for the first time. A total of 17, 20, 19 and 17 constituents were identified comprising 99.90, 95.50, 98.93 and 95.96% of the essential oil of flower, leaf, stem and root parts of Senecio graciliflorus respectively. Monoterpene hydrocarbons predominated in the essential oil with 85.28% in flower, 57.53% in leaf, 67.74% in stem and 64.98% in root oil. α-pinene, cis-ocimene, 1,2,3-trimethylcyclohexane and ß-pinene were the major constituents of the essential oil. The flower essential oil exhibited a strong antioxidant potential displaying IC50 values of 21.6±0.6 and 26.0±1.0µg/ml in DPPH and hydroxyl radical assays respectively. On the other hand the essential oil of flower and root displayed highest cytotoxicity against lung (A-549) cancer cell lines (IC50=19.1±0.9 and 21.3±1.1µg/ml respectively. This study which represents the first report of the essential oil composition and bioevaluation of Senecio graciliflorus, can serve as a new source of cytotoxic and antioxidant activity.
Assuntos
Antineoplásicos Fitogênicos/uso terapêutico , Antioxidantes/uso terapêutico , Neoplasias Pulmonares/tratamento farmacológico , Óleos Voláteis/uso terapêutico , Fitoterapia , Estruturas Vegetais/química , Senécio/química , Antineoplásicos Fitogênicos/análise , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/análise , Antioxidantes/farmacologia , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Linhagem Celular Tumoral , Cicloexanos/análise , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Concentração Inibidora 50 , Monoterpenos/análise , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Óleos de Plantas/químicaRESUMO
As a peculiar folk medicinal plant, Acanthopanax brachypus was widely used to treat various diseases in China. At present, however, there is not a good quality standard for its quality evaluation. In this study, on the basis of the validation tests of precision, stability and repeatability, the chromatographic fingerprint of A. brachypus was established by using gas chromatography (GC)-flame ionization detector (FID) and GC-MS techniques, as well as computer aided similarity evaluation system. Thirty-two different batches of samples collected from the different producing regions and the different parts of A. brachypus were studied. The results showed that the dominant constituents of all oils were monoterpenes and sesquiterpenes, as well as oxygenated monoterpenes and sesquiterpenes. The fingerprinting profiles were found to be consistent for the fresh stem bark acquired from various production areas, 48 common peaks were determined, but the relative abundance of peaks was varied. ß-Pinene, linalool, p-cymene, spathulenol, camphene, endo-borneol, verbenone, ß-caryophyllene, γ-terpinene, germacrene-D, camphor, ß-thujone and ß-cadinene were the main constituents of the fresh stem bark oil. Except for the leaf, the chemical components among different medicinal parts of fresh plant were inconsistent with the stem bark. Besides, the varieties and relative levels of chemical components in the fresh stem bark were more abundant than in the dry counterpart. The GC-MS fingerprint can be successfully applied to distinguish the substitute or adulterant, and further assess the differences of A. brachypus grown in various areas of China.
Assuntos
Eleutherococcus/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Monoterpenos Acíclicos , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Monoterpenos Cicloexânicos , Cimenos , Monoterpenos/análise , Sesquiterpenos Policíclicos , Sesquiterpenos/análise , Sesquiterpenos de Germacrano/análise , Terpenos/análiseRESUMO
Essential oils of the resins of Pinus brutia and Pinus pinea were evaluated for their biological potential. Essential oils were characterized using GC-MS and GC/FID. in vitro antimicrobial, phytotoxic, antioxidant, and insecticidal activities were carried out using the direct contact and the fumigant assays, respectively. The chemical profile of the essential oils of the resins of P. pinea and P. brutia included mainly α-pinene (21.39% and 25.40%), ß-pinene (9.68% and 9.69%), and caryophyllene (9.12% and 4.81%). The essential oils of P. pinea and P. brutia exerted notable antimicrobial activities on Micrococcus luteus and Bacillus subtilis, insecticidal activities on Ephestia kuehniella eggs, phytotoxic activities on Lactuca sativa, Lepidium sativum, and Portulaca oleracea, as well as antioxidant potential. Indications of the biological activities of the essential oils suggest their use in the formulation of ecofriendly and biocompatible pharmaceuticals.
Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Inseticidas/farmacologia , Óleos Voláteis/farmacologia , Pinus/química , Extratos Vegetais/farmacologia , Terpenos/farmacologia , Animais , Anti-Infecciosos/análise , Antioxidantes/análise , Bacillus subtilis/efeitos dos fármacos , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Insetos/efeitos dos fármacos , Inseticidas/análise , Lepidium/efeitos dos fármacos , Lactuca/efeitos dos fármacos , Região do Mediterrâneo , Micrococcus luteus/efeitos dos fármacos , Monoterpenos/análise , Monoterpenos/farmacologia , Óleos Voláteis/química , Extratos Vegetais/química , Óleos de Plantas/química , Óleos de Plantas/farmacologia , Sesquiterpenos Policíclicos , Portulaca/efeitos dos fármacos , Resinas Vegetais/química , Sesquiterpenos/análise , Sesquiterpenos/farmacologia , Terpenos/análiseRESUMO
OBJECTIVES: This study aimed to evaluate the variations of the chemical composition and bioactivity of essential oils of Liquidambar styracifluaâ L. (Altingiaceae) collected in different seasons. METHODS: The oils were analysed by GLC/FID and GLC/MS. The antioxidant activity was investigated by diphenylpicrylhydrazyl (DPPH) and superoxide anion radical scavenging assays and the deoxyribose degradation assay. Inhibition of both 5-lipoxygenase (5-LOX) and prostaglandin E2 (PGE2) production in hepatic cancer (HepG-2) cells were used to assess the anti-inflammatory activity. The cytotoxic activity was investigated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. KEY FINDINGS: Altogether, 64 volatile secondary metabolites were identified. The major components of the leaf oil were d-limonene, α-pinene and ß-pinene, and of the stem oil were germacrine D, α-cadinol, d-limonene, α-pinene, and ß-pinene. Leaf and stem oils collected in spring could reduce DPPHâ (IC50 = 3.17 and 2.19 mg/ml) and prevent the degradation of the deoxyribose sugar (IC50 = 17.55 and 14.29 µg/ml). The stem oil exhibited a higher inhibition of both 5-LOX and PGE2 than the leaf oil. The cytotoxic activity of leaf and stem oils was low in cancer cell lines (IC50 = 136.27 and 119.78 µg/ml in cervical cancer (HeLa) cells). CONCLUSIONS: Essential oils of L. styraciflua exhibited an interesting anti-inflammatory activity with low cytotoxicity, supporting its traditional use to treat inflammation.