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1.
Molecules ; 27(14)2022 Jul 09.
Artigo em Inglês | MEDLINE | ID: mdl-35889279

RESUMO

Guatteria olivacea R. E. Fries (synonym Guatteria punctata (Aubl.) R.A. Howard) is a tree of 10-27 m tall popularly known as "envira-bobó", "envira-fofa", "envireira", "embira", "embira-branca", "embira-preta", envira-branca", and "envira-preta", which can be found in the Brazilian Amazon biome. In this study, we evaluated the cytotoxic and antitumor effects of the essential oil (EO) obtained from the leaves of G. olivacea against liver cancer using HepG2 cells as a model. EO was obtained using a hydrodistillation Clevenger-type apparatus and was qualitatively and quantitatively characterized using GC-MS and GC-FID, respectively. The alamar blue assay was used to assess the cytotoxic potential of EO in a panel of human cancer cell lines and human non-cancerous cells. In HepG2 cells treated with EO, YO-PRO-1/propidium iodide staining, cell cycle distribution, and reactive oxygen species (ROS) were examined. In C.B-17 SCID mice with HepG2 cell xenografts, the efficacy of the EO (20 and 40 mg/kg) was tested in vivo. GC-MS and GC-FID analyses showed germacrene D (17.65%), 1-epi-cubenol (13.21%), caryophyllene oxide (12.03%), spathulenol (11.26%), (E)-caryophyllene (7.26%), bicyclogermacrene (5.87%), and δ-elemene (4.95%) as the major constituents of G. olivacea leaf EO. In vitro cytotoxicity of EO was observed, including anti-liver cancer action with an IC50 value of 30.82 µg/mL for HepG2 cells. In HepG2 cells, EO treatment increased apoptotic cells and DNA fragmentation, without changes in ROS levels. Furthermore, the EO inhibited tumor mass in vivo by 32.8-57.9%. These findings suggest that G. olivacea leaf EO has anti-liver cancer potential.


Assuntos
Annonaceae , Guatteria , Neoplasias , Óleos Voláteis , Animais , Humanos , Camundongos , Camundongos SCID , Óleos Voláteis/farmacologia , Folhas de Planta , Espécies Reativas de Oxigênio
2.
Biomed Pharmacother ; 122: 109713, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31918282

RESUMO

Guatteria megalophylla Diels (Annonaceae) is an 8-10 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 100 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 µg/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 SCID
3.
Phytochemistry ; 145: 18-25, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29059536

RESUMO

Three guaianolide sesquiterpenes, denoted guatterfriesols A-C, and four aporphine alkaloid derivatives were isolated from the stem bark of the Amazonian plant Guatteria friesiana. Thus far, sesquiterpene lactones have not been described in Annonaceae. Structures of the previously undescribed compounds were established by using 1D and 2D NMR spectroscopy in combination with MS. The absolute stereochemistry was assigned via NOE NMR experiments, ECD spectroscopy, and theoretical calculations using the TDDFT approach. Among the isolated compounds, the alkaloid guatterfriesidine showed anti-glycation activity by inhibiting the formation of advanced glycation end-products (AGEs) through the prevention of oxidation in both BSA/methylglyoxal and BSA/fructose systems.


Assuntos
Aporfinas/farmacologia , Produtos Finais de Glicação Avançada/antagonistas & inibidores , Guatteria/química , Lactonas/farmacologia , Sesquiterpenos de Guaiano/farmacologia , Aporfinas/química , Aporfinas/isolamento & purificação , Relação Dose-Resposta a Droga , Produtos Finais de Glicação Avançada/metabolismo , Glicosilação/efeitos dos fármacos , Lactonas/química , Lactonas/isolamento & purificação , Estrutura Molecular , Casca de Planta/química , Caules de Planta/química , Teoria Quântica , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/isolamento & purificação , Relação Estrutura-Atividade
4.
Chem Biodivers ; 14(10)2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28719026

RESUMO

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 & purificação
5.
Exp Parasitol ; 172: 51-60, 2017 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-28011169

RESUMO

Leishmaniasis is caused by protozoan parasites belonging to the genus Leishmania and includes cutaneous, mucocutaneous and visceral clinical forms. The drugs currently available for leishmaniasis treatment are pentavalent antimonials, amphotericin B and miltefosine, which present high toxicity, elevated cost and development of parasite resistance. The natural products constitute an important source of substances with leishmanicidal potential. Here we evaluated in vitro the anti-Leishmania amazonensis activity of crude extracts of branches, leaves and fruits of Guatteria latifolia. The branch extract (GCE) exhibited promising leishmanicidal activity against promastigotes (IC50 51.7 µg/ml), and was submitted to fractionation guided by in vitro assays. Among the seven subfractions obtained, GF1 and GF2 were the most actives against promastigotes with IC50 25.6 and 16 µg/ml, respectively. Since GCE, GF1 and GF2 were not toxic for macrophages, next, we tested their effect on intracellular amastigotes, and the IC50 values obtained were, respectively 30.5, 10.4 and 7.4 µg/ml, after 24 h treatment. The selectivity index for GCE, GF1 and GF2 were >6.5, >19.2 and > 27, respectively. Additionally, GCE, GF1 and GF2 affected the division pattern of the promastigotes by increasing 6.7, 9.4 and 7-fold the cells in Sub-G0/G1 phase, and decreasing 1.6, 2.5 and 1.8-fold the cells in G0/G1 phase, respectively. To assess the GCE and GFs capacity to modulate microbicidal mechanisms of macrophages, nitric oxide (NO) and TNF-α production were tested. Our results indicated that at the IC50s GCE, GF1 and GF2 decreased NO production of infected macrophages stimulated with IFN-γ and LPS, besides, only GF1 decreased the production of TNF-α. Our data warrant further studies of GCE, GF1 and GF2 to identify active compounds against Leishmania parasites.


Assuntos
Alcaloides/farmacologia , Antiprotozoários/farmacologia , Guatteria , Leishmania mexicana/efeitos dos fármacos , Extratos Vegetais/farmacologia , Alcaloides/análise , Alcaloides/isolamento & purificação , Antiprotozoários/química , Antiprotozoários/isolamento & purificação , Ciclo Celular/efeitos dos fármacos , Interferon gama/biossíntese , Leishmania mexicana/citologia , Leishmania mexicana/metabolismo , Ativação de Macrófagos , Macrófagos/imunologia , Macrófagos/parasitologia , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Óxido Nítrico/metabolismo , Extratos Vegetais/química , Fator de Necrose Tumoral alfa/biossíntese
7.
J Photochem Photobiol B ; 160: 154-62, 2016 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27107335

RESUMO

Photodynamic Therapy, a tumor therapy idealized at the beginning of the last century, emerges nowadays as a promising treatment alternative against infectious diseases. In this study we report a bioguided study of Guatteria blepharophylla phytoderivatives for antimicrobial PDT. Crude extracts and fraction from the species bark were obtained and further fractionated for substances isolation. All samples were evaluated in relation to their photophysical (absorbance and fluorescence) and photochemical properties (1,3-DPBF bleaching method). Then, bioassays were conducted using as biological models bacteria and yeast strains and a diode laser as a light source. Phytochemical analyses lead to the isolation of 5 isoquinoline alkaloids from oxoaporphine subclass, denominated GB1 to GB5. Photophysical and photochemical analysis showed that extracts, fraction and GB1 (isomoschatoline) presented absorption profile with bands at 600-700nm and were positive for singlet oxygen production. Photobiological assays indicate that these samples presented photodynamic antimicrobial activity against both gram-positive and gram-negative bacterial and some Candida ssp. yeast strains at sub-inhibitory concentrations. The susceptibility of gram-negative bacteria was significantly enhanced when CaCl2 or MgCl2 were employed. Greater energy doses and double sample's dosage also decreased microbial survival. It is suggested that GB1 photodynamic activity happens through both types I and II photochemical mechanisms, but with a predominance of the latter. Phytoderivatives of G. blepharophylla promoted antimicrobial effect, however more detailed study concerning chemical composition of the crude extracts and fractions as also photophysical and photochemical characteristics of GB1 are necessary to ensure their potential as photosensitizers at antimicrobial photodynamic inactivation.


Assuntos
Alcaloides/farmacologia , Antibacterianos/farmacologia , Aporfinas/farmacologia , Guatteria/química , Extratos Vegetais/farmacologia , Testes de Sensibilidade Microbiana , Espectrometria de Fluorescência
8.
Alkaloids Chem Biol ; 74: 233-409, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25845063

RESUMO

This chapter presents an overview of the chemistry and pharmacology of the alkaloids found in species of the Annonaceae family. The occurrence of alkaloids from Annonaceae species, as well as their chemical structures and pharmacological activities are summarized in informative and easy-to-understand tables. Within the Annonaceae family, the genera Annona, Duguetia, and Guatteria have led to many important publications. Valuable and comprehensive information about the structure of these alkaloids is provided. The alkaloids of the aporphine type represent the predominant group in this family. Many of the isolated alkaloids exhibit unique structures. In addition to the chemical structures, the pharmacological activities of some alkaloids are also presented in this chapter. Thus, the leishmanicidal, antimicrobial, antitumor, cytotoxic, and antimalarial activities observed for these alkaloids are highlighted. The chapter is presented as a contribution for the scientific community, mainly to enable the search for alkaloids in species belonging to the Annonaceae family.


Assuntos
Alcaloides/química , Alcaloides/farmacologia , Annonaceae/química , Alcaloides/classificação , Annona/química , Annonaceae/classificação , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antimaláricos/química , Antimaláricos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Aporfinas/química , Aporfinas/farmacologia , Guatteria/química , Estrutura Molecular
9.
Nat Prod Res ; 29(20): 1966-9, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25710362

RESUMO

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 Vegetais/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 & purificação
10.
Chem Biodivers ; 10(4): 722-9, 2013 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-23576358

RESUMO

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 20.8 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 100 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 Heterólogo
11.
Planta Med ; 78(5): 409-14, 2012 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-22274812

RESUMO

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 Vegetais/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 Vegetais/uso terapêutico , Plantas Medicinais/química , Sarcoma 180 , Sesquiterpenos de Eudesmano/administração & dosagem , Sesquiterpenos de Eudesmano/uso terapêutico
12.
Planta Med ; 77(15): 1749-53, 2011 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-21567357

RESUMO

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 , Ultrafiltração
13.
J Nat Prod ; 73(6): 1180-3, 2010 Jun 25.
Artigo em Inglês | MEDLINE | ID: mdl-20476748

RESUMO

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).


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Guatteria/química , Plantas Medicinais/química , Alcaloides/química , Antibacterianos/química , Antifúngicos/química , Antioxidantes/química , Aporfinas/química , Brasil , Candida/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química , Pseudomonas aeruginosa/efeitos dos fármacos , Staphylococcus/efeitos dos fármacos
14.
Planta Med ; 72(3): 270-2, 2006 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-16534735

RESUMO

Nine known alkaloids [(+)-isodomesticine (1), (+)-norisodomesticine (2), (+)-nantenine ( 3), (+)-neolitsine (4), (+)-lirioferine (5), (+)-N-methyllaurotetanine (6), (+)-norlirioferine (7), (+)-isoboldine (8) and (+)-reticuline (9)] were isolated from young leaves of Guatteria dumetorum. Their structures were confirmed by NMR, mass and UV spectral analysis and by comparison to literature data. The growth inhibitory activity of each alkaloid was determined against the parasite Leishmania mexicana. Compounds 1-4 all showed significant activity whereby potency increased when a methylenedioxy functionality was present, especially at the 1,2-positions.


Assuntos
Guatteria , Leishmania mexicana/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/farmacologia , Tripanossomicidas/farmacologia , Animais , Chlorocebus aethiops , Humanos , Leishmaniose Cutânea/tratamento farmacológico , Macrófagos/efeitos dos fármacos , Camundongos , Testes de Sensibilidade Parasitária , Extratos Vegetais/administração & dosagem , Extratos Vegetais/uso terapêutico , Folhas de Planta , Tripanossomicidas/administração & dosagem , Tripanossomicidas/uso terapêutico , Células Vero/efeitos dos fármacos
15.
Planta Med ; 69(7): 677-9, 2003 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-12898429

RESUMO

Fractionation of Guatteria amplifolia yielded the alkaloids xylopine (1), nornuciferine (4), lysicamine (6), and laudanosine (5). Fractionation of Guatteria dumetorum yielded the alkaloids cryptodorine (2) and nornantenine (3). Compounds 1-4 demonstrated significant activity against Leishmania mexicana and L. panamensis. Xylopine (1) was among the most active compounds (LD 50 = 3 microM) and showed a 37-fold higher toxicity towards L. mexicana than macrophages, the regular host cells of Leishmania spp.


Assuntos
Alcaloides/isolamento & purificação , Guatteria/química , Leishmania mexicana/efeitos dos fármacos , Leishmania/efeitos dos fármacos , Alcaloides/farmacologia , Animais , Humanos
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