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1.
Plants (Basel) ; 10(9)2021 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-34579388

RESUMO

Lauraceae families have great diversity in the world's tropical regions and are represented mainly by aromatic shrubs and trees with significant production of essential oils (EOs). This work presents a review of the EO chemical profiles from specimens of Aniba, including their seasonal variations, geographical distributions, and biological activities in the Amazon biome. Based on the survey, 15 species were reviewed, representing 167 oil samples extracted from leaves, twig barks, and woods. Brazilian Amazon was the most representative geographic area in the number of specimens, highlighting the locations Belém, (Pará state, PA) (3 spp., 37 samples), Santarém (PA) (3 spp., 10 samples), Carajás (PA) (3 spp., 7 samples), and Manaus (Amazonas state, AM) (3 spp., 16 samples). The main compound classes identified in oils were benzenoids and phenylpropanoids, represented by 1-nitro-2-phenylethane, benzyl salicylate, benzyl benzoate and methyleugenol, along with terpenoids, especially monoterpenes and sesquiterpenes, such as linalool, α-phellandrene, ß-phellandrene, ß-selinene, and spathulenol. The EOs from Aniba showed considerable variation in the chemical profiles according to season and collection site. The hierarchical cluster analysis classified the samples into two main groups according to chemical composition. This review highlights its comprehensive and up-to-date information on history, conservation, traditional uses, chemosystematics, pharmacological potential of Aniba species.

2.
Molecules ; 26(7)2021 Mar 29.
Artigo em Inglês | MEDLINE | ID: mdl-33805452

RESUMO

Lauraceae species are widely represented in the Amazon, presenting a significant essential oil yield, large chemical variability, various biological applications, and high economic potential. Its taxonomic classification is difficult due to the accentuated morphological uniformity, even among taxa from a different genus. For this reason, the present work aimed to find chemical and molecular markers to discriminate Aniba species collected in the Pará State (Brazil). The chemical composition of the essential oils from Aniba canelilla, A. parviflora, A. rosaeodora, and A. terminalis were grouped by multivariate statistical analysis. The major compounds were rich in benzenoids and terpenoids such as 1-nitro-2-phenylethane (88.34-70.85%), linalool (15.2-75.3%), α-phellandrene (36.0-51.8%), and ß-phellandrene (11.6-25.6%). DNA barcodes were developed using the internal transcribed spacer (ITS) nuclear region, and the matK, psbA-trnH, rbcL, and ycf1 plastid regions. The markers psbA-trnH and ITS showed the best discrimination for the species, and the phylogenic analysis in the three- (rbcL + matK + trnH - psbA and rbcL + matK + ITS) and four-locus (rbcL + matK + trnH - psbA + ITS) combination formed clades with groups strongly supported by the Bayesian inference (BI) (PP:1.00) and maximum likelihood (ML) (BS ≥ 97%). Therefore, based on statistical multivariate and phylogenetic analysis, the results showed a significant correlation between volatile chemical classes and genetic characteristics of Aniba species.


Assuntos
Código de Barras de DNA Taxonômico/métodos , DNA de Plantas , Lauraceae , Óleos Voláteis/análise , Brasil , Lauraceae/química , Lauraceae/classificação , Filogenia , Especificidade da Espécie
3.
Microorganisms ; 9(3)2021 Feb 25.
Artigo em Inglês | MEDLINE | ID: mdl-33669088

RESUMO

To elucidate defense mechanisms of Piper nigrum against fusariosis, an experiment based on co-inoculation of arbuscular mycorrhizal fungi (AMF) and Fusarium solani f. sp. piperis was performed. Variations in secondary metabolism in plants infected with F. solani f. sp. piperis (FUS) and co-inoculated with AMFs and F. solani (AMF + FUS) were monitored at 7- and 21-days post inoculations (dpi). The pathogen induced a decrease in oxygenated sesquiterpenes (82.0-77.4%), and changes in the concentrations of the main compounds, α-muurolene, α-muurolol, and 2E-hexenal in the leaves. It was observed that the concentration of 2E-hexenal decreased at 7 dpi, α-muurolene decreased at 21 dpi, and α-muurolol increased at 21 dpi. There was a prevalence of sesquiterpene and monoterpene hydrocarbons in the roots, such as ß-caryophyllene, δ-elemene, and limonene. The infection and co-inoculation induced greater production of phenolics in the roots at 7 dpi. The enzymatic activity of phenylalanine ammonia-lyase decreased in the leaves at 21 dpi and in the roots on both days, while the lipoxygenase activity decreased only in the roots at 21 dpi. The results demonstrated that co-inoculation with AMFs and F. solani induces changes in the defense metabolism of P. nigrum, but it is not efficient in the biocontrol of fusariosis during the evaluated period.

4.
Int J Mol Sci ; 22(2)2021 Jan 17.
Artigo em Inglês | MEDLINE | ID: mdl-33477389

RESUMO

This study evaluated the chemical compositions of the leaves and fruits of eight black pepper cultivars cultivated in Pará State (Amazon, Brazil). Hydrodistillation and gas chromatography-mass spectrometry were employed to extract and analyze the volatile compounds, respectively. Sesquiterpene hydrocarbons were predominant (58.5-90.9%) in the cultivars "Cingapura", "Equador", "Guajarina", "Iaçará", and "Kottanadan", and "Bragantina", "Clonada", and "Uthirankota" displayed oxygenated sesquiterpenoids (50.6-75.0%). The multivariate statistical analysis applied using volatile composition grouped the samples into four groups: γ-Elemene, curzerene, and δ-elemene ("Equador"/"Guajarina", I); δ-elemene ("Iaçará"/"Kottanadan"/"Cingapura", II); elemol ("Clonada"/"Uthirankota", III) and α-muurolol, bicyclogermacrene, and cubebol ("Bragantina", IV). The major compounds in all fruit samples were monoterpene hydrocarbons such as α-pinene, ß-pinene, and limonene. Among the cultivar leaves, phenolics content (44.75-140.53 mg GAE·g-1 FW), the enzymatic activity of phenylalanine-ammonia lyase (20.19-57.22 µU·mL-1), and carotenoids (0.21-2.31 µg·mL-1) displayed significant variations. Due to black pepper's susceptibility to Fusarium infection, a molecular docking analysis was carried out on Fusarium protein targets using each cultivar's volatile components. F. oxysporum endoglucanase was identified as the preferential protein target of the compounds. These results can be used to identify chemical markers related to the susceptibility degree of black pepper cultivars to plant diseases prevalent in Pará State.


Assuntos
Piper nigrum/metabolismo , Sesquiterpenos/análise , Sesquiterpenos/metabolismo , Brasil , Frutas/química , Frutas/genética , Cromatografia Gasosa-Espectrometria de Massas/métodos , Metaboloma , Simulação de Acoplamento Molecular , Monoterpenos/análise , Monoterpenos/metabolismo , Óleos Voláteis/química , Piper nigrum/genética , Folhas de Planta/genética , Óleos Vegetais/química , Sesquiterpenos/química
5.
J Food Sci Technol ; 57(9): 3176-3183, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32728267

RESUMO

Chemical composition and antioxidant and antifungal action of the oils from leaves and wood bark of two chemotypes of Cinnamomum verum J. Presl were evaluated. Plants were sampled in the cities of São Luís and Santa Inês, state of Maranhão, Brazil. GC-MS and GC-FID, DPPH radical scavenging, and in vitro test against the phytopathogenic fungus Colletotrichum musae were used to perform these analyses. Cinnamomum verum is worldwide known as Cinnamon, highlighted for its extensive use in the cooking of diverse cultures of the world, and as a medicinal plant to treat environmental viral diseases. In the leaf oil of São Luís chemotype, eugenol (93.6%) was the main constituent, while in Santa Inês chemotype, it was benzyl benzoate (95.3%). In the bark wood oil of São Luís chemotype, (E)-cinnamaldehyde (89.3%) was the main constituent, while in Santa Inês chemotype, they were benzyl benzoate (23.3%), linalool (14.0%), (E)-caryophyllene (9.1%), caryolan-8-ol (7.2%) and borneol (4.7%). Leaf oils from both chemotypes showed strong to moderate antifungal activity, reaching 100% efficacy in eugenol-containing oils and above 70% in benzyl benzoate oils. In the antioxidant evaluation, the chemotype with a high eugenol content presented an inhibitory concentration higher than 80%, compared to Trolox. The leaf oils of the two C. verum chemotypes showed significant antifungal and antioxidant potential, considering their economic use as a functional and nutraceutical food supplement.

6.
Biomolecules ; 10(6)2020 06 05.
Artigo em Inglês | MEDLINE | ID: mdl-32517106

RESUMO

Lauraceae species are known as excellent essential oil (EO) producers, and their taxa are distributed throughout the territory of Brazil. This study presents a systematic review of chemical composition, seasonal studies, occurrence of chemical profiles, and biological activities to EOs of species of Licaria, Nectandra, and Ocotea genera collected in different Brazilian biomes. Based on our survey, 39 species were studied, with a total of 86 oils extracted from seeds, leaves, stem barks, and twigs. The most representative geographic area in specimens was the Atlantic Forest (14 spp., 30 samples) followed by the Amazon (13 spp., 30 samples), Cerrado (6 spp., 14 samples), Pampa (4 spp., 10 samples), and Caatinga (2 spp., 2 samples) forests. The majority of compound classes identified in the oils were sesquiterpene hydrocarbons and oxygenated sesquiterpenoids. Among them, ß-caryophyllene, germacrene D, bicyclogermacrene, caryophyllene oxide, α-bisabolol, and bicyclogermacrenal were the main constituents. Additionally, large amounts of phenylpropanoids and monoterpenes such as safrole, 6-methoxyelemicin, apiole, limonene, α-pinene, ß-pinene, 1,8-cineole, and camphor were reported. Nectandra megatopomica showed considerable variation with the occurrence of fourteen chemical profiles according to seasonality and collection site. Several biological activities have been attributed to these oils, especially cytotoxic, antibacterial, antioxidant and antifungal potential, among other pharmacological applications.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Lauraceae/química , Óleos Voláteis/química , Animais , Antibacterianos/química , Antifúngicos/química , Antineoplásicos Fitogênicos/química , Antioxidantes/química , Brasil , Ecossistema , Humanos , Especificidade da Espécie
7.
Biomolecules ; 10(2)2020 02 19.
Artigo em Inglês | MEDLINE | ID: mdl-32092893

RESUMO

The essential oil of Eugenia uniflora has been attributed anti-depressive, antinociceptive, antileishmanial, larvicidal, antioxidant, antibacterial, and antifungal activities. It is known that the cultivation of this plant can be affected by seasonality, promoting alteration in the oil composition and its biological activities. This study aims to perform the annual evaluation of the curzerene-type oil of E. uniflora and determine its antioxidant activity. The oil yield from the dry season (1.4 ± 0.6%) did not differ statistically from that of the rainy season (1.8 ± 0.8%). Curzerene, an oxygenated sesquiterpene, was the principal constituent, and its percentage showed no significant difference between the two periods: dry (42.7% ± 6.1) and rainy (40.8 ± 5.9%). Principal component and hierarchical cluster analyses presented a high level of similarity between the monthly samples of the oils. Also, in the annual study, the yield and composition of the oils did not present a significant correlation with the climatic variables. The antioxidant activity of the oils showed inhibition of DPPH radicals with an average value of 55.0 ± 6.6%. The high curzerene content in the monthly oils of E. uniflora suggests their potential for use as a future phytotherapeutic alternative.


Assuntos
Antioxidantes/química , Eugenia/química , Óleos Voláteis/química , Antioxidantes/farmacologia , Óleos Voláteis/farmacologia , Estações do Ano , Sesquiterpenos/química , Sesquiterpenos/farmacologia
8.
Molecules ; 24(23)2019 Nov 21.
Artigo em Inglês | MEDLINE | ID: mdl-31766491

RESUMO

Black pepper (Piper nigrum) is historically one of the most important spices and herbal medicines, and is now cultivated in tropical regions worldwide. The essential oil of black pepper fruits has shown a myriad of biological activities and is a commercially important commodity. In this work, five black pepper essential oils from eastern coastal region of Madagascar and six black pepper essential oils from the Amazon region of Brazil were obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. The major components of the essential oils were α-pinene, sabinene, ß-pinene, δ-3-carene, limonene, and ß-caryophyllene. A comparison of the Madagascar and Brazilian essential oils with black pepper essential oils from various geographical regions reported in the literature was carried out. A hierarchical cluster analysis using the data obtained in this study and those reported in the literature revealed four clearly defined clusters based on the relative concentrations of the major components.


Assuntos
Frutas/química , Óleos Voláteis/análise , Piper nigrum/química , Compostos Orgânicos Voláteis/análise , Análise por Conglomerados , Óleos Voláteis/química , Compostos Orgânicos Voláteis/química
9.
Colloids Surf B Biointerfaces ; 182: 110382, 2019 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-31352250

RESUMO

Solid inclusion complexes with cyclodextrins (CD) may be used to overcome volatility and solubility problems of essential oils of pharmacological interest. However, they lack the many dermatological advantages of lipid nanoparticles. This study intends to evaluate the ability of nanostructured lipid carriers (NLC) to encapsulate hydroxypropyl-ß-cyclodextrin inclusion complexes of Lippia origanoides essential oil (EO) and to maintain the desirable aspects of lipid colloids interaction with the skin, specifically follicular accumulation and controlled delivery. CD and NLC were also evaluated separately. Thymol (TML) was used as the essential oil marker and to produce control formulations. As expected, CD alone, though effective in overcoming volatility and low aqueous solubility of TML, were ineffective in controlling marker release (˜50% of EO released after 3 h, Hixson-Crowell kinetics). Even though NLC controlled drug release (˜20% EO released after 12 h, zero-order kinetics) enabling TML penetration into the skin (> 40 µg/cm2after 12 h), NLC alone were not efficient in preventing TML volatility, especially at higher temperatures (calculated shelf-life of 2 days at 35 °C). The combined approach resulted in a synergistic effect (˜20% EO released after 12 h; shelf life of 6 days). The lack of statistical difference of TML skin penetration from NLC and NLC-CD suggests the developed system maintained all skin interaction aspects of lipid colloids, including follicular accumulation forming a depot for controlled delivery. In conclusion, lipid nanoparticles demonstrated to be promising carriers for inclusion complexes of this particular volatile essential oil.


Assuntos
Ciclodextrinas/administração & dosagem , Portadores de Fármacos/química , Lipídeos/química , Nanopartículas/química , Óleos Voláteis/administração & dosagem , Administração Cutânea , Animais , Ciclodextrinas/química , Ciclodextrinas/farmacocinética , Preparações de Ação Retardada/administração & dosagem , Preparações de Ação Retardada/química , Preparações de Ação Retardada/farmacocinética , Liberação Controlada de Fármacos , Nanopartículas/ultraestrutura , Óleos Voláteis/química , Óleos Voláteis/farmacocinética , Pele/metabolismo , Solubilidade , Suínos , Temperatura , Timol/administração & dosagem , Timol/química , Timol/farmacocinética , Volatilização
10.
AMB Express ; 9(1): 29, 2019 Feb 26.
Artigo em Inglês | MEDLINE | ID: mdl-30806846

RESUMO

The aim of this study was to evaluate the changes in the production of secondary metabolites Piper aduncum seedlings were inoculated by spores of the arbuscular mycorrhizal fungi (AMF) Rhizophagus clarus and Claroideoglomus etunicatum. P. aduncum seedlings were inoculated by spores of R. clarus and C. etunicatum and then, development parameters, root colonization, lipoxygenase (LOX) activity, and essential oil (OE) chemical composition were monitored at 30, 60 and 90 days' post-inoculation (dpi). The inoculation had influenced the plant height and root length at 30 and 90 dpi and microscopic analysis of roots showed the presence of hyphae, arbuscules and vesicles in the inoculated plants. Phenylpropanoids and sesquiterpene hydrocarbons were the main compounds in the EO. In the leaves, the concentration of phenylpropanoids showed a decrease, mainly at 60 dpi, with increased sesquiterpene hydrocarbon production. The main compounds were dillapiole, myristicin, and germacrene D; the dillapiole concentration decreased in all treatments. LOX activity had an increase in the leaves and roots at 90 dpi. These results suggest that alterations in the secondary metabolites of P. aduncum can be induced by its mechanisms of resistance during AMF interaction.

11.
J Ethnopharmacol ; 232: 90-102, 2019 Mar 25.
Artigo em Inglês | MEDLINE | ID: mdl-30562552

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Peperomia pellucida (L.) Kunth is an annual weed with a preference to humid places with reduced solar radiation. This plant is mainly distributed in the Neotropics, Africa, Southeast Asia, and Australia. It is popularly employed in the treatment of a variety of health conditions such as abscesses, abdominal pain, skin sores, conjunctivitis, measles, and kidney troubles. Several studies have also described its antimicrobial, cytotoxic, antidiabetic and a variety of other bioactivities. THE AIM OF THE REVIEW: The aim of this work is to evaluate, using a critical review, the present ethnomedicinal applications, phytochemistry and pharmacological studies of P. pellucida essential oils (EOs) and extracts from different locations around the world. MATERIALS AND METHODS: This review was performed through an online survey of the ethnomedicinal practices, chemical compositions and pharmacological applications of P. pellucida EOs and extracts. The data were mainly obtained from online journals and books published in English, Portuguese and Spanish. The information was collected from websites such as Google, Google Scholar, PubMed, Science Direct, ResearchGate and other online databases that provided more information about this herb. RESULTS: Peperomia pellucida bioactivities such as antimicrobial, cytotoxic, antioxidant, fracture healing, antidiabetic and anti-hypercholesterolemia have been described in several literature sources. Nonetheless, most reports only provide the phytochemical screening of extracts, which does not allow the identification of the active compounds. From these studies, some reported constituents are not included in the Dictionary of Natural Products (DNP), which raises questions toward their identification. In addition, some biological assays were even performed without standard controls for comparison which also makes these results questionable. CONCLUSION: This review evaluates data regarding the phytopharmaceutical potential of P. pellucida. In general, several important aspects were questionable or missing in these manuscripts, which points out the need of more investigation on the pharmacological properties and phytochemical compositions of this herb.


Assuntos
Peperomia , Compostos Fitoquímicos/farmacologia , Fitoterapia , Animais , Humanos , Medicina Tradicional , Peperomia/química , Compostos Fitoquímicos/análise
12.
Nat Prod Res ; 33(4): 506-515, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-29130365

RESUMO

Chemical composition of the methanol extract of Myrciaria floribunda leaves was investigated. The nor-lupane triterpenoids platanic acid and messagenic I acid were identified, along with other known triterpenoids (betulinic aldehyde, ursolic acid acetate and betulinic acid), a new lupane triterpenoid (2α,6α,30-trihydroxybetulinic acid) and the flavonoids catechin, quercetrin and mirycitrin. The structures were determined by spectroscopic methods (NMR, LC-MS, GC-MS). The major isolated compound was betulinic acid. The methanol extract and 2α,6α,30-trihydroxybetulinic acid were evaluated for their DPPH scavenging potential. The tested triterpenoid was one hundred times more active than betulinic acid, but less active than the extract. Screening for antimicrobial activity showed that the methanol extract was active against Staphylococcus aureus and Escherichia coli, but inactive against Candida albicans and Candida krusei, while 2α,6α,30-trihydroxybetulinic acid was inactive to all tested microorganisms.


Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Myrtaceae/química , Extratos Vegetais/química , Triterpenos/farmacologia , Anti-Infecciosos/análise , Anti-Infecciosos/química , Antioxidantes/análise , Antioxidantes/química , Candida albicans/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos/métodos , Flavonoides/química , Cromatografia Gasosa-Espectrometria de Massas , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Triterpenos Pentacíclicos , Extratos Vegetais/análise , Extratos Vegetais/farmacologia , Folhas de Planta/química , Staphylococcus aureus/efeitos dos fármacos , Triterpenos/análise , Triterpenos/química , Triterpenos/isolamento & purificação
13.
J Ethnopharmacol ; 232: 30-38, 2019 Mar 25.
Artigo em Inglês | MEDLINE | ID: mdl-30543916

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Oils and extracts of Eugenia uniflora have been reported as antimicrobial, antifungal, antinociceptive, antiprotozoal, antioxidant and cytotoxic. AIM OF THE STUDY: The oils of five specimens (E1 to E5) that occur in the Brazilian Amazon were extracted, analyzed for their chemical composition, and submitted to antioxidant and cytotoxic assays. MATERIAL AND METHODS: Oils were hydrodistilled, analyzed by GC and GC-MS, and submitted to PCA and HCA analyses. The antioxidant activity of the oils was evaluated by the DPPH radical scavenging and the ß-carotene/linoleic acid assays. Antiproliferative effects of the oils and curzerene were tested against colon (HCT-116), gastric (AGP-01), and melanoma (SKMEL-19) human cancer cell lines and a normal human fibroblast cell line (MRC-5), using MTT assay. RESULTS: Oxygenated sesquiterpenes and sesquiterpene hydrocarbons such as curzerene, selina-1,3,7(11)-trien-2-one, selina-1,3,7(11)-trien-2-one epoxide, germacrene B, caryophyllene oxide, and (E)-caryophyllene were predominant in the oils. PCA and HCA analyses classified the oils samples into four chemotypes. TEAC values of chemotype II (E3 oil, 228.3 ±â€¯19.2 mg TE/mL) and chemotype III (E4 oil, 217.0 ±â€¯23.3 mg TE/mL) displayed significant antioxidant activities. The oils E2 and E4 showed cytotoxic activity against all cell lines tested HCT-116 (IC50 E2:16.26 µg/mL; IC50 E4:9.28 µg/mL), AGP-01, (IC50 E2:12.60 µg/mL; IC50 E4:8.73 µg/mL), SKMEL-19 (IC50 E2:12.20 µg/mL; IC50 E4:15.42 µg/mL), and MRC-5 (IC50 E2:10.27 µg/mL; IC50 E4:14.95 µg/mL). Curzerene showed the more significant activity against melanoma cells (SKMEL-19, IC50:5.17 µM), induced apoptosis at 5.0 µM and 10.0 µM compared to DMSO, exhibiting a decrease in the cell migration at 5.0 µM and 10.0 µM, after 30 h of treatment. CONCLUSION: The curzerene chemotype oil and E. uniflora oils can be indicated as drug candidates for anticancer activity of the lung, colon, stomach, and melanoma, with a real prospect to their subsequent phytotherapeutic development.


Assuntos
Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Eugenia , Óleos Vegetais/farmacologia , Antineoplásicos/química , Antioxidantes/química , Brasil , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Eugenia/química , Humanos , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Óleos Vegetais/química , Cicatrização/efeitos dos fármacos
14.
Chem Cent J ; 12(1): 52, 2018 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-29748791

RESUMO

BACKGROUND: Psidium guineense, known as Araçá, is a Brazilian botanical resource with commercial application perspectives, based on the functional elements of its fruits and due to the use of its leaves as an anti-inflammatory and antibacterial agent. The essential oils of leaves of twelve specimens of Araçá were analyzed by GC and GC-MS to identify their volatile constituents and associate them with the biological activities reputed to the plant. RESULTS: In a total of 157 identified compounds, limonene, α-pinene, ß-caryophyllene, epi-ß-bisabolol, caryophyllene oxide, ß-bisabolene, α-copaene, myrcene, muurola-4,10(14)-dien-1-ß-ol, ß-bisabolol, and ar-curcumene were the primary components in descending order up to 5%. Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) displayed three different groups with the following chemical types: limonene/α-pinene, ß-bisabolene/epi-ß-bisabolol, and ß-caryophyllene/caryophyllene oxide. With the previous description of another chemical type rich in spathulenol, it is now understood that at least four different chemotypes for P. guineense should occur. CONCLUSIONS: In addition to the use of the Araçá fruits, which are rich in minerals and functional elements, it should be borne in mind that the knowledge of the chemical composition of the essential oils of leaves of their different chemical types may contribute to the selection of varieties with more significant biological activity.

15.
Medicines (Basel) ; 4(3)2017 Jul 08.
Artigo em Inglês | MEDLINE | ID: mdl-28930266

RESUMO

Background:Eugenia species are appreciated for their edible fruits and are known as having anticonvulsant, antimicrobial and insecticidal actions. Methods: The plant material was collected in the southeastern Pará state of Brazil and submitted to hydrodistillation. GC-MS analyzed the oils, and their antioxidant and cytotoxic activities were evaluated by the DPPH and MTT assays. Results: The main components identified in the Eugenia oils were 5-hydroxy-cis-calemene, (2E,6E)-farnesol, (2E,6Z)-farnesol, caryophylla-4(12),8(13)-dien-5α-ol-5ß-ol, E-γ-bisabolene, ß-bisabolene, germacrene D, and ishwarane. The oil of E. egensis showed the most significant antioxidant activity (216.5 ± 11.6 mg TE/mL), followed by the oils of E. flavescens (122.6 ± 6.8 mg TE/mL) and E. patrisii (111.2 ± 12.4 mg TE/mL). Eugenia oils were cytotoxic to HCT-116 (colon cancer) cells by the MTT assay, where the most active was the oil of E. polystachya (10.3 µg/mL), followed by the oils of E. flavescens (13.9 µg/mL) and E. patrisii (16.4 µg/mL). The oils of E. flavescens and E. patrisii showed the highest toxicity for MRC5 (human fibroblast) cells, with values of 14.0 µg/mL and 18.1 µg/mL, respectively. Conclusions: These results suggest that Eugenia oils could be tested in future studies for the treatment of colon cancer and oxidative stress management.

16.
PLoS One ; 12(5): e0175598, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28459864

RESUMO

The essential oils (EOs) of the aerial parts of Lippia origanoides (LiOr), collected in different localities of the Amazon region, were obtained by hydrodistillation and analyzed by GC and CG-MS. Principle component analysis (PCA) based on chemical composition grouped the oils in four chemotypes rich in mono- and sesquiterpenoids. Group I was characterized by 1,8-cineole and α-terpineol (LiOr-1 and LiOr-4) and group II by thymol (LiOr-2). The oil LiOr-3 showed ß-caryophyllene, α-phellandrene and ß-phellandrene as predominant and LiOr-5 was rich in (E)-nerolidol and ß-caryophyllene. All samples were evaluated for antioxidant activity and inhibition of tyrosinase in vitro and in silico. The highest antioxidant activity by the DPPH free radical method was observed in LiOr-2 and LiOr-5 oils (132.1 and 82.7 mg TE∙mL-1, respectively). The tyrosinase inhibition potential was performed using L-tyrosine and L-DOPA as substrates and all samples were more effective in the first step of oxidation. The inhibition by samples LiOr-2 and LiOr-4 were 84.7% and 62.6%, respectively. The samples LiOr-1, LiOr-4 and LiOr-5 displayed an interaction with copper (II) ion with bathochromic shift around 15 nm. In order to elucidate the mechanism of inhibition of the main compounds, a molecular docking study was carried out. All compounds displayed an interaction between an oxygen and Cu or histidine residues with distances less than 4 Å. The best docking energies were observed with thymol and (E)-nerolidol (-79.8 kcal.mol-1), which suggested H-bonding interactions with Met281 and His263 (thymol) and His259, His263 ((E)-nerolidol).


Assuntos
Antioxidantes/farmacologia , Lippia/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Óleos Voláteis/farmacologia , Óleos Vegetais/farmacologia , Animais , Antioxidantes/química , Quelantes/química , Quelantes/farmacologia , Cromatografia Gasosa , Cobre/química , Destilação , Ligação de Hidrogênio , Levodopa/metabolismo , Espectrometria de Massas , Simulação de Acoplamento Molecular , Monofenol Mono-Oxigenase/metabolismo , Óleos Voláteis/química , Fitoterapia , Óleos Vegetais/química , Análise de Componente Principal , Análise Espectral
17.
Chem Biodivers ; 14(3)2017 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-27701813

RESUMO

Lavandula pubescens Decne. is one of five Lavandula species growing wild in Yemen. The plant is used in Yemeni traditional medicine, and the essential oil tends to be rich in carvacrol. In this work, L. pubescens was collected from eight different locations in Yemen, the essential oils obtained by hydrodistillation, and the oils analyzed by gas chromatography/mass spectrometry (GC/MS). Principal component analysis (PCA) and hierarchical cluster analysis (HCA) were used to differentiate between the L. pubescens samples. The essential oils were rich in carvacrol (60.9 - 77.5%), with lesser concentrations of carvacrol methyl ether (4.0 - 11.4%), caryophyllene oxide (2.1 - 6.9%), and terpinolene (0.6 - 9.2%). The essential oil compositions in this study showed very high similarity, but it was possible to discern two separate groups based on minor components, in particular the concentrations of terpinolene, carvacrol methyl ether, m-cymen-8-ol, and caryophyllene oxide.


Assuntos
Lamiaceae/química , Óleos Voláteis/química , Análise por Conglomerados , Cimenos , Cromatografia Gasosa-Espectrometria de Massas , Lamiaceae/metabolismo , Monoterpenos/análise , Monoterpenos/química , Óleos Voláteis/análise , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Análise de Componente Principal , Iêmen
18.
Lipids Health Dis ; 15(1): 174, 2016 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-27717404

RESUMO

BACKGROUND: Piper aequale Vahl is a small shrub that grows in the shadow of large trees in the Carajás National Forest, Municipality of Parauapebas, Para state, Brazil. The local people have used the plant against rheumatism and inflammation. METHODS: The essential oil of the aerial parts was extracted and analyzed by GC and GC-MS. The MTT colorimetric assay was used to measuring the cytotoxic activity of the oil against human cancer lines. The determination of antioxidant activity of the oil was conducted by DPPH radical scavenging assay. RESULTS: The main constituents were δ-elemene (18.92 %), ß-pinene (15.56 %), α-pinene (12.57 %), cubebol (7.20 %), ß-atlantol (5.87 %), and bicyclogermacrene (5.51 %), totalizing 65.63 % of the oil. The oil displayed a strong in vitro cytotoxic activity against the human cancer cell lines HCT-116 (colon) and ACP03 (gastric) with IC50values of 8.69 µg/ml and 1.54 µg/ml, respectively. The oil has induced the apoptosis in a gastric cancer cells in all tested concentration (0.75-3.0 µg/ml), after 72 h of treatment, when compared to negative control (p < 0.001). Also, the oil showed a significant antioxidant activity (280.9 ± 22.2 mg TE/ml), when analyzed as Trolox equivalent, and a weak acetylcholinesterase inhibition, with a detection limit of 100 ng, when compared to the physostigmine standard (1.0 ng). CONCLUSION: The higher cell growth inhibition induced by the oil of P. aequale is probably due to its primary terpene compounds, which were previously reported in the proliferation inhibition, in stimulation of apoptosis and induction of cell cycle arrest in malignant cells.


Assuntos
Antioxidantes/administração & dosagem , Neoplasias do Colo/tratamento farmacológico , Óleos Voláteis/administração & dosagem , Óleos Vegetais/administração & dosagem , Neoplasias Gástricas/tratamento farmacológico , Antioxidantes/química , Apoptose/efeitos dos fármacos , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Neoplasias do Colo/patologia , Células HCT116 , Humanos , Óleos Voláteis/química , Piper/química , Óleos Vegetais/química , Neoplasias Gástricas/patologia
19.
Nat Prod Commun ; 11(5): 695-8, 2016 May.
Artigo em Inglês | MEDLINE | ID: mdl-27319154

RESUMO

The essential oils (EOs) of leaves and twigs of Endlicheria arenosa Chanderb. were obtained by hydrodistillation using a Clevenger-type apparatus and the chemical composition was determined by GC and GC-MS. In total, 47 constituents were identified and sesquiterpene hydrocarbons (77.6%) were the main compounds found in the leaf EO, such as bicyclogermacrene (42.2%), germacrene D (12.5%) and ß-caryophyllene (10.1%). Limonene (33.2%), terpinen-4-ol (15.6%) and δ-cadinol (6.9%) were the predominant constituents in the EO of the twigs. Using the DPPH radical-scavenging method, the EO of the leaves showed the greater radical-scavenging activity (216.5 ± 11.6 mg Trolox equivalents (TE)/mL compared to the EO of the twigs (122.6 ± 6.8 mg TE/mL). Also, the EO of leaves displayed promising antimicrobial activity against Escherichia coli (MIC 19.5 µg x mL(-1)). The present study is the first report about evaluation of volatile oils for this species.


Assuntos
Anti-Infecciosos/análise , Antioxidantes/análise , Lauraceae/química , Óleos Voláteis/química , Brasil , Testes de Sensibilidade Microbiana , Óleos Voláteis/análise
20.
Nat Prod Commun ; 11(7): 1025-1028, 2016 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30452187

RESUMO

Essential oils (EOs) from leaves and branches of Aniba parviflora (Meisn.) Mez were obtained by hydrodistillation and their chemical compositions determined by gas chromatography - mass spectrometry. Oxygenated sesquiterpenoids were the most representative compound class in both EOs (~ 40%). However, the leaf EO was rich in ß-phellandrene (15.1%), linalool (14.1%), and y-eudesmol (12.9%). The EO from the branches showed high concentrations of γ-eudesmol (16.8%), ß-caryophyllene (15.7%), linalool (12.4%), ß-phellandrene (6.7%), and bicyclogermacrene (6.0%). The EOs were screened for radical-scavenging activity using the DPPH assay. In the DPPH assay, the EOs showed an antioxidant activity with TEAC values of 296.8 ± 20.2 and 357.3 ± 43.8 mg.TE.mL⁻¹, about one-third that of the Trolox standard. The EOs were subjected to antibacterial screening and displayed promising activity against Escherichia coli (MIC < 19.5 µg.mL⁻¹). In addition, the EOs were tested for cytotoxic activity against MCF-7 breast tumor cells and the leaf EO (IC50 = 67.9 ± 3.0 µg.mL⁻¹.) was more active than that from the branches (IC50 = 102.2 ± 3.0 µg.mL⁻¹).


Assuntos
Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Lauraceae/química , Óleos Voláteis/farmacologia , Anti-Infecciosos/química , Antineoplásicos Fitogênicos/química , Antioxidantes/química , Bactérias/efeitos dos fármacos , Compostos de Bifenilo , Sobrevivência Celular/efeitos dos fármacos , Humanos , Células MCF-7 , Óleos Voláteis/química , Picratos
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