RESUMO
The essential oils (EOs) of Guatteria schomburgkiana (Gsch) and Xylopia frutescens (Xfru) (Annonaceae) were obtained by hydrodistillation, and their chemical composition was evaluated by gas chromatography-mass spectrometry (GC/MS). Herbicide activity was measured by analyzing the seed germination percentage and root and hypocotyl elongation of two invasive species: Mimosa pudica and Senna obtusifolia. The highest yield was obtained for the EO of Xfru (1.06%). The chemical composition of Gsch was characterized by the presence of the oxygenated sesquiterpenes spathulenol (22.40%) and caryophyllene oxide (14.70%). Regarding the EO of Xfru, the hydrocarbon monoterpenes α-pinene (35.73%) and ß-pinene (18.90%) were the components identified with the highest concentrations. The germination of seeds of S. obtusifolia (13.33 ± 5.77%) showed higher resistance than that of seeds of M. pudica (86.67 ± 5.77%). S. obtusifolia was also more sensitive to the EO of Xfru in terms of radicle (55.22 ± 2.72%) and hypocotyl (71.12 ± 3.80%) elongation, while M. pudica showed greater sensitivity to the EO of Gsch. To screen the herbicidal activity, the molecular docking study of the major and potent compounds was performed against 4-hydroxyphenylpyruvate dioxygenase (HPPD) protein. Results showed good binding affinities and attributed the strongest inhibitory activity to δ-cadinene for the target protein. This work contributes to the study of the herbicidal properties of the EOs of species of Annonaceae from the Amazon region.
Assuntos
Annonaceae , Guatteria , Óleos Voláteis , Xylopia , Annonaceae/química , Xylopia/química , Guatteria/química , Óleos Voláteis/química , Brasil , Simulação de Acoplamento Molecular , Folhas de Planta/químicaRESUMO
In the present study, it was evaluated the chemical composition and the antinociceptive activity of the essential oil obtained from the leaves of Guatteria friesiana. Seven compounds corresponding to 96.2% of the crude essential oil were identified. The main components identified were the mixture of ß-eudesmol and α-eudesmol (58.1%), and γ-eudesmol (16.8%). A new α-eudesmol derivative, named 5-hydroxy-α-eudesmol, was isolated together with the known compounds ß-eudesmol and a mixture of α-eudesmol, ß-eudesmol and γ-eudesmol of the essential oil. The chemical structures were determined by 1D and 2D NMR, and MS experiments. Essential oil has significant antinociceptive properties, which are related probably with the involvement of the opioid receptors and K+-ATP channels.
Assuntos
Annonaceae , Guatteria , Óleos Voláteis , Óleos Voláteis/química , Guatteria/química , Annonaceae/química , Folhas de Planta/química , Analgésicos/farmacologiaRESUMO
Guatteria megalophylla Diels (Annonaceae) is an 8-10â¯m tall tree that grows near streams and is widely spread throughout Colombian, Ecuadorian, Peruvian, Brazilian and Guianese Amazon rainforest. Herein, we investigated for the first time the chemical composition and in vitro and in vivo anti-leukemia potential of G. megalophylla leaf essential oil (EO) using human promyelocytic leukemia HL-60 cells as model. EO was obtained by a hydrodistillation clevenger-type apparatus and characterized quali- and quantitatively by GC-MS and GC-FID, respectively. In vitro cytotoxic potential of EO was evaluated in human cancer cell lines (HL-60, MCF-7 CAL27, HSC-3, HepG2 and HCT116) and in human non-cancer cell line (MRC-5) by Alamar blue method. Annexin V/propidium iodide staining, cell cycle distribution and reactive oxygen species (ROS) were assessed by flow cytometry for HL-60 cells treated with EO. In vivo efficacy of EO (50 and 100â¯mg/kg) was evaluated in C.B-17 SCID mice with HL-60 cell xenografts. Chemical composition analyses showed spathulenol, γ-muurolene, bicyclogermacrene, ß-elemene and δ-elemene as main constituents of assayed sample. EO displayed in vitro cytotoxicity, including anti-leukemia effect with IC50 value of 12.51⯵g/mL for HL-60 cells. EO treatment caused augment of phosphatidylserine externalization and DNA fragmentation without increasing of ROS in HL-60 cells. In vivo tumor mass inhibition rates of EO was 16.6-48.8 %. These data indicate anti-leukemia potential of G. megalophylla leaf EO.
Assuntos
Annonaceae/química , Proliferação de Células/efeitos dos fármacos , Guatteria/química , Leucemia Promielocítica Aguda/tratamento farmacológico , Óleos Voláteis/farmacologia , Folhas de Planta/química , Preparações de Plantas/farmacologia , Animais , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular , Linhagem Celular Tumoral , Células HCT116 , Células HL-60 , Células Hep G2 , Humanos , Células MCF-7 , Masculino , Camundongos SCIDRESUMO
The essential oils (EOs) extracted from four species of the genus Guatteria, G. australis, G. ferruginea, G. latifolia, and G. sellowiana were analyzed. A total of 24, 22, 25, and 19 constituents of the oils from four species, respectively, were identified by GC/MS. These oils showed qualitative and quantitative differences. All the oils contained the oxygenated sesquiterpenes spathulenol (11.04 - 40.29%) and caryophyllene oxide (7.74 - 40.13%) as predominant constituents. Evaluation of antiproliferative activity of the EOs showed strong selectivity (1.1 - 4.1 µg/ml) against the tumor cell line OVCAR-03 (ovarian cancer), i.e., more active than the positive control doxorubicin (11.7 µg/ml). All EOs showed strong antibacterial activity (minimum inhibitory concentrations of 0.062 - 0.25 mg/ml) against strains of Rhodococcus equi.
Assuntos
Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Bactérias/efeitos dos fármacos , Guatteria/química , Óleos Voláteis/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificaçãoRESUMO
Phytochemical investigation of the bark of Guatteria friesiana afforded 12 new aporphines (1-12), along with nine known alkaloids (13-21). The structures of the new alkaloids were determined on the basis of spectroscopic data interpretation. The cytotoxic activity of the isolated compounds against a small panel of tumor cell lines was assessed using the Alamar blue assay.
Assuntos
Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Aporfinas/isolamento & purificação , Guatteria/química , Casca de Planta/química , Alcaloides/química , Alcaloides/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Aporfinas/química , Aporfinas/farmacologia , Brasil , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Células Hep G2 , Humanos , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Essential oil from the leaves of Guatteria australis was obtained by hydrodistillation, analyzed by Gas Chromatography coupled to Mass Spectromery (GC-MS) and their antiproliferative, antileishmanial, antibacterial, antifungal and antioxidant activities were also evaluated. Twenty-three compounds were identified among which germacrene B (50.66%), germacrene D (22.22%) and (E)-caryophyllene (8.99%) were the main compounds. The highest antiproliferative activity was observed against NCI-ADR/RES (TGI = 31.08 µg/ml) and HT-29 (TGI = 32.81 µg/ml) cell lines. It also showed good antileishmanial activity against Leishmania infantum (IC50 = 30.71 µg/ml). On the other hand, the oil exhibited a small effect against Staphylococcus aureus ATCC 6538, S. aureus ATCC 14458 and Escherichia coli ATCC 10799 (MIC = 250 µg/ml), as well as small antioxidant activity (457 µmol TE/g) assessed through ORACFL assay. These results represent the first report regarding chemical composition and bioactivity of G. australis essential oil.
Assuntos
Antibacterianos/química , Antineoplásicos Fitogênicos/química , Antiprotozoários/química , Guatteria/química , Óleos Voláteis/química , Óleos de Plantas/química , Antibacterianos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antiprotozoários/isolamento & purificação , Células HT29 , Humanos , Folhas de Planta/química , Sesquiterpenos Policíclicos , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/isolamento & purificaçãoRESUMO
Guatteria pogonopus Martius, a plant belonging to the Annonaceae family, is found in the remaining Brazilian Atlantic Forest. In this study, the chemical composition and antitumor effects of the essential oil isolated from leaves of G. pogonopus was investigated. The chemical composition of the oil was determined by GC-FID and GC/MS analyses. The in vitro cytotoxicity was evaluated against three different tumor cell lines (OVCAR-8, NCI-H358M, and PC-3M), and the in vivo antitumor activity was tested in mice bearing sarcoma 180 tumor. A total of 29 compounds was identified and quantified in the oil. The major compounds were γ-patchoulene (13.55%), (E)-caryophyllene (11.36%), ß-pinene (10.37%), germacrene D (6.72%), bicyclogermacrene (5.97%), α-pinene (5.33%), and germacrene B (4.69%). The essential oil, but neither (E)-caryophyllene nor ß-pinene, displayed in vitro cytotoxicity against all three tumor cell lines tested. The obtained average IC50 values ranged from 3.8 to 20.8â µg/ml. The lowest and highest values were obtained against the NCI-H358M and the OVCAR-8 cell lines, respectively. The in vivo tumor-growth-inhibition rates in the tumor-bearing mice treated with essential oil (50 and 100â mg/kg/d) were 25.3 and 42.6%, respectively. Hence, the essential oil showed significant in vitro and in vivo antitumor activity.
Assuntos
Antineoplásicos Fitogênicos/química , Guatteria/química , Óleos Voláteis/química , Animais , Antineoplásicos Fitogênicos/uso terapêutico , Antineoplásicos Fitogênicos/toxicidade , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Masculino , Camundongos , Neoplasias/tratamento farmacológico , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/toxicidade , Folhas de Planta/química , Sarcoma/tratamento farmacológico , Transplante HeterólogoRESUMO
Guatteria friesiana (W. A. Rodrigues) Erkens & Maas (synonym Guatteriopsis friesiana W. A. Rodrigues), popularly known as "envireira", is a medicinal plant found in the Brazilian and Colombian Amazon basin that is used in traditional medicine for various purposes. Recent studies on this species have demonstrated antimicrobial activity. In this study, the antitumor activity of the essential oil from the leaves of G. friesiana (EOGF) and its main components ( α-, ß-, and γ-eudesmol) were determined using experimental models. In the in vitro study, EOGF and its components α-, ß-, and γ-eudesmol displayed cytotoxicity against tumor cell lines, showing IC50 values in the range of 1.7 to 9.4 µg/mL in the HCT-8 and HL-60 cell lines for EOGF, 5.7 to 19.4 µg/mL in the HL-60 and MDA-MB-435 cell lines for α-eudesmol, 24.1 to > 25 µg/mL in the SF-295 and MDA-MB-435 cell lines for ß-eudesmol, and 7.1 to 20.6 µg/mL in the SF-295 and MDA-MB-435 cell lines for γ-eudesmol, respectively. In the in vivo study, the antitumor effect of EOGF was evaluated in mice inoculated with sarcoma 180 tumor cells. Tumor growth inhibition rates were 43.4-54.2 % and 6.6-42.8 % for the EOGF treatment by intraperitoneal (50 and 100 mg/kg/day) and oral (100 and 200 mg/kg/day) administration, respectively. The treatment with EOGF did not significantly affect body mass, macroscopy of the organs, or blood leukocyte counts. Based on these results, we can conclude that EOGF possesses significant antitumor activity and has only low systemic toxicity. These effects could be assigned to its components α-, ß-, and γ-eudesmol.
Assuntos
Antineoplásicos Fitogênicos/administração & dosagem , Guatteria/química , Óleos Voláteis/administração & dosagem , Óleos de Plantas/administração & dosagem , Administração Oral , Animais , Antineoplásicos Fitogênicos/uso terapêutico , Brasil , Linhagem Celular Tumoral , Colômbia , Humanos , Concentração Inibidora 50 , Injeções Intraperitoneais , Masculino , Camundongos , Estrutura Molecular , Óleos Voláteis/uso terapêutico , Folhas de Planta/química , Óleos de Plantas/uso terapêutico , Plantas Medicinais/química , Sarcoma 180 , Sesquiterpenos de Eudesmano/administração & dosagem , Sesquiterpenos de Eudesmano/uso terapêuticoRESUMO
Our current research on applications of mass spectrometry to natural product drug discovery against malaria aims to screen plant extracts for new ligands to Plasmodium falciparum thioredoxin reductase (PfTrxR) followed by their identification and structure elucidation. PfTrxR is involved in the antioxidant defense and redox regulation of the parasite and is validated as a promising target for therapeutic intervention against malaria. In the present study, detannified methanol extracts from Guatteria recurvisepala, Licania kallunkiae, and Topobea watsonii were screened for ligands to PfTrxR using ultrafiltration and liquid chromatography/mass spectrometry-based binding experiments. The PfTrxR ligand identified in the extract of Guatteria recurvisepala displayed a relative binding affinity of 3.5-fold when incubated with 1 µM PfTrxR. The ligand corresponding to the protonated molecule m/z 282.2792 [M+ H]+ was eluted at a retention time of 17.95 min in a 20-min gradient of 95% B consisting of (A) 0.1%formic acid in 95% H2O-5% ACN, and (B) 0.1% formic acid in 95% ACN-5% H2O in an LC-QTOF-MS.Tandem MS of the protonated molecule m/z 282.2792 [M + H]+, C18H36NO (DBE: 2; error: 1.13 ppm) resulted in two daughter ions m/z 265.2516[M + H-NH3]+ (DBE: 3; error: 0.35 ppm) and m/z 247.2405 [M + H-NH3-H2O] +, (DBE: 4; error:2.26 ppm). The PfTrxR ligand was identified as oleamide and confirmed by comparison of the retention time, molecular formula, accurate mass,and double bond equivalence with the standard oleamide. This is the first report on the identification of oleamide as a PfTrxR ligand from Guatteria recurvisepala R. E. Fr. and the corresponding in vitro activity against P. falciparum strain K1 (IC50 4.29 µg/mL).
Assuntos
Antimaláricos/química , Guatteria/química , Ácidos Oleicos/química , Extratos Vegetais/química , Plasmodium falciparum/enzimologia , Tiorredoxina Dissulfeto Redutase/metabolismo , Animais , Antimaláricos/isolamento & purificação , Linhagem Celular , Sobrevivência Celular , Cromatografia Líquida , Chrysobalanaceae/química , Descoberta de Drogas , Concentração Inibidora 50 , Ligantes , Espectrometria de Massas , Melastomataceae/química , Ácidos Oleicos/isolamento & purificação , Panamá , Extratos Vegetais/isolamento & purificação , Ratos , Padrões de Referência , UltrafiltraçãoRESUMO
Phytochemical investigation of the bark of Guatteria hispida afforded three new alkaloids, 9-methoxy-O-methylmoschatoline (1), 9-methoxyisomoschatoline (2), and isocerasonine (3), along with 10 known alkaloids, 8-oxopseudopalmatine (4), O-methylmoschatoline (5), lysicamine (6), liriodenine (7), 10-methoxyliriodenine (8), nornuciferine (9), anonaine (10), xylopine (11), coreximine (12), and isocoreximine (13). The major compounds, 2, 6, 12, and 13, showed significant antioxidant capacity in the ORAC(FL) assay. Compounds 5, 6, and 7 were active against S. epidermidis and C. dubliniensis, with MIC values in the range 12.5-100 microg mL(-1).