RESUMO
7-(2'-Hydroxy-3'-chloroprenyloxy)-4,8-dimethoxyfuroquinoline (1) and 6-(2'-hydroxy-3'-chloroprenyloxy)-4,7-dimethoxyfuroquinoline (2), together with ten known compounds, have been isolated from the aerial parts of Ertela (Monnieria) trifolia (L.) Kuntze. All the isolates were tested for antiproliferative activity against the A2780 human ovarian cancer cell line.
Assuntos
Alcaloides/química , Quinolinas/química , Rutaceae/química , Clima Tropical , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Feminino , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Neoplasias Ovarianas/patologia , Quinolinas/farmacologia , Chuva , SurinameRESUMO
A new cytotoxic macrocyclic glycoresin, ipomoeassin F (6), has been isolated from the leaves of Ipomoea squamosa. The structure was elucidated by the interpretation of spectral data. Compound 6 was strongly active in the A2780 (human ovarian cancer cell line) assay with an IC(50) value of 0.036 microM.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Glicoconjugados/administração & dosagem , Glicoconjugados/química , Glicoconjugados/farmacologia , Glicoconjugados/uso terapêutico , Ipomoea , Fitoterapia , Extratos Vegetais/farmacologia , Antineoplásicos Fitogênicos/administração & dosagem , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/uso terapêutico , Linhagem Celular Tumoral/efeitos dos fármacos , Humanos , Concentração Inibidora 50 , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Folhas de Planta , SurinameRESUMO
Bioassay-guided fractionation of the MeOH and EtOAc fractions of extracts of two lianas collected in Suriname has led to the isolation of five new diterpenoids, humirianthone 1, 1-hydroxy-humirianthone 2, 15R-humirianthol 3, patagonol 4, and patagonal 5, and the five known diterpenoids, humirianthol 7, annonalide 8, acrenol 9, icacinol 10, and the oxidized annonalide 11. All 10 diterpenoids showed cytotoxic activity against the A2780 human ovarian cancer cell line, and compounds 1, 3, 8, and 9 also showed activity against phytopathogenic fungi.
Assuntos
Diterpenos/isolamento & purificação , Diterpenos/toxicidade , Plantas Medicinais/química , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antifúngicos/toxicidade , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Diterpenos/química , Diterpenos/farmacologia , Fungos/efeitos dos fármacos , Fungos/fisiologia , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Chuva , Suriname , ÁrvoresRESUMO
The new glycoresins, ipomoeassins A-E (1-5), have been isolated from the leaves of Ipomoea squamosa. The structures were elucidated by spectroscopic analyses and chemical transformations. The absolute configurations of C-5 (ipomoeassins 3-5) and C-11 (ipomoeassins 1 and 2) were determined by their derivatives with (R)- and (S)-MPA. All the isolates were active in the A2780 human ovarian cancer cell line assay, and 4 showed the highest activity with an IC(50) value of 35 nM.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Glicosídeos/isolamento & purificação , Ipomoea/química , Plantas Medicinais/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Estereoisomerismo , Suriname , Células Tumorais CultivadasRESUMO
Bioassay-guided fractionation of an EtOAc extract of the leaves of Melampodium camphoratum using an assay for inhibitors of the degradation of hemin resulted in the isolation of six new eudesmane sesquiterpenes (1-6) and the known 6-epi-beta-verbesinol coumarate (7). The structures of compounds 1-6 were established as 6alpha-(4'-O-methyl-7'E-coumaryloxy)eudesm-4(14)-ene (1), 6alpha-({4'-O-stearyl}-7'E-coumaryloxy)eudesm-4(14)-ene (2), 6alpha-({4'-O-palmityl}-7'E-coumaryloxy)eudesm-4(14)-ene (3), 6alpha-({4'-O-[9' 'Z-hexadecenoyl]}-7'E-coumaryloxy)eudesm-4(14)-ene (4), 6alpha-(7'Z-coumaryloxy)eudesm-4(14)-ene (5), and 6alpha-({4'-acetoxy}-7'Z-coumaryloxy)eudesm-4(14)-ene (6). Compounds 1-4 showed weak activity in the hemin degradation assay, while compounds 5-7 were inactive.
Assuntos
Antimaláricos/isolamento & purificação , Asteraceae/química , Hemina/metabolismo , Plantas Medicinais/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Animais , Antimaláricos/química , Antimaláricos/farmacologia , Concentração Inibidora 50 , Estrutura Molecular , Folhas de Planta/química , Plasmodium falciparum/efeitos dos fármacos , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia , Estereoisomerismo , SurinameRESUMO
Bioassay-guided fractionation of the EtOAc extract of the twigs of Garcinia macrophylla from Suriname produced the known benzophenone, guttiferone A (1), and a new guttiferone analogue, guttiferone G (2). Friedelin was also isolated. The structures of compounds 1 and 2 were elucidated using 1D and 2D NMR spectroscopy. Compounds 1 and 2 were weakly cytotoxic in the A2780 human ovarian cell line, with IC (50) values of 6.8 and 8.0 microg/mL, respectively.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Benzofenonas/farmacologia , Garcinia , Fitoterapia , Extratos Vegetais/farmacologia , Antineoplásicos Fitogênicos/administração & dosagem , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/uso terapêutico , Benzofenonas/administração & dosagem , Benzofenonas/química , Benzofenonas/uso terapêutico , Linhagem Celular Tumoral/efeitos dos fármacos , Relação Dose-Resposta a Droga , Feminino , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Neoplasias Ovarianas/prevenção & controle , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , SurinameRESUMO
Two novel triterpene acids, esculentoic acid A ( 1) and B ( 2) as well as the seven known compounds 3 - 9 were isolated from an EtOAc extract of leaves, stems, and twigs of Manihot esculenta by bioassay-guided fractionation for cytotoxic activity. The structures of the two new compounds were established as 3alpha-hydroxytaraxer-14-en-29-oic acid ( 1) and 3-oxotaraxer-14-en-29-oic acid ( 2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. The two new compounds 1 and 2 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Manihot , Fitoterapia , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/uso terapêutico , Feminino , Humanos , Espectroscopia de Ressonância Magnética , Neoplasias Ovarianas/tratamento farmacológico , Neoplasias Ovarianas/patologia , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Folhas de Planta , Caules de Planta , Suriname , Triterpenos/química , Triterpenos/uso terapêutico , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Bioassay-guided fractionation of the MeOH extract of Acacia tenuifolia using the engineered yeast strains 1138, 1140, 1353, and Sc7 as the bioassay tool resulted in the isolation of the three new saponins 3, 5, and 6 and the three known saponins 1, 2, and 4. The structures of the new compounds were established on the basis of HRMS, 1D and 2D NMR spectral data on the intact saponins, and GC-MS analyses of the sugars. Compounds 1,2 and 5,6 showed cytotoxicity against mammalian cell lines.
Assuntos
Acacia/química , Antineoplásicos Fitogênicos/isolamento & purificação , Ácido Oleanólico/análogos & derivados , Plantas Medicinais/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Animais , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Concentração Inibidora 50 , Neoplasias Pulmonares , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Neoplasias Ovarianas , Saponinas/química , Saponinas/farmacologia , Estereoisomerismo , Suriname , Triterpenos/química , Triterpenos/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacos , Leveduras/efeitos dos fármacosRESUMO
Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.