RESUMO
The phytochemical investigations of the tuber roots of Asparagus flagellaris led to the isolation of a new alkaloid, schweinfurthiamide (1) and eight known compounds. The structures of the isolated compounds were elucidated using spectroscopic techniques 1D and 2D NMR (1H, 13C, COSY, HMBC, HMQC, HSQC-TOCSY). The absolute configuration of 1 was unambiguously determined using DP4+ calculations. Compound 1 showed significant cytotoxicity against MCF-7 (breast cancer), NCI-H460 (lung cancer), and Hela (cervical cancer) cancer cell lines with IC50 values of 1.18 ± 0.02 µM, 2.25 ± 0.19 µM, and 4.23 ± 0.26 µM, respectively and no toxicity against normal human fibroblast (BJ).
RESUMO
Six new triterpenoid saponins, named senegalosides A-F (1-6) were isolated from the seedpods and roots of Acacia senegal (Mimosaceae). Their structures were elucidated using 1D and 2D-NMR spectroscopic analysis and mass spectrometry. Compound 1 possesses an unusual sapogenin, 3ß-hydroxy-21-oxo-olean-12-en-28-oic acid (machaeric acid), and was reported here in its natural form for the first time within the genus Acacia. Senegaloside A is the first example of a machaeric-type triterpenoid glycoside in the plant kingdom. The cytotoxic effect of isolated saponins was evaluated on the H4IIE rat hepatoma cell line. As a result, compounds 1, 3-6 were not significantly cytotoxic to H4IIE cells even at 200 µM. Compound 2 was suppressed cell viability at 50-200 µM.
Assuntos
Acacia/química , Antineoplásicos Fitogênicos/farmacologia , Saponinas/farmacologia , Triterpenos/farmacologia , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Camarões , Linhagem Celular Tumoral , Sobrevivência Celular , Ensaios de Seleção de Medicamentos Antitumorais , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Raízes de Plantas/química , Ratos , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificaçãoRESUMO
Three new fusarielins, 3-epi-fusarielin H (1), 3-O-methyl-fusarielin H (2), and 3-O-methyl-epi-fusarielin H (3), were isolated from the fungus Fusarium sp. together with the known analogues, fusarielins F (4) and G (5). The structures of these compounds were elucidated by analysis of their ESI-HRTOFMS, 1D and 2D NMR spectroscopic data. The new compounds exhibited weak antibacterial effect against Staphylococcus aureus.
Assuntos
Antibacterianos/química , Antifúngicos/química , Fusarium/química , Naftalenos/química , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Compostos de Epóxi/química , Compostos de Epóxi/farmacologia , Fermentação , Humanos , Espectroscopia de Ressonância Magnética , Naftalenos/farmacologiaRESUMO
Two new triterpene saponins, albidosides H (1) and I (2), along with the three known saponins were isolated from the barks of Acacia albida. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry. Albidosides H (1) and I (2) were assayed for their cytotoxicity against HeLa and HL60 cells using MTT method.
Assuntos
Acacia/química , Saponinas/química , Triterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais/métodos , Células HL-60 , Células HeLa , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Ácido Oleanólico/análogos & derivados , Casca de Planta/química , Saponinas/farmacologia , Triterpenos/farmacologiaRESUMO
Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1-4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR data and HR-ESI-MS analyses. At concentrations of 100 µM of each compounds, none of the tested compounds caused a significant growth reduction against HL60 cells.
Assuntos
Acacia/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Raízes de Plantas/química , Saponinas/química , Triterpenos/química , Triterpenos/farmacologia , Proliferação de Células/efeitos dos fármacos , Células HL-60 , HumanosRESUMO
A new eremophilane sesquiterpene, 13,13-dimethoxyintegric acid (1), together with known compound integric acid (2) have been isolated from a fungus, Xylaria sp. V-27, obtained from a dead branch. The structure of 1 was established by means of spectroscopic analyses. 1 and 2 promoted growth restoring activity against the mutant yeast strain (Saccharomyces cerevisiae (zds1Δ erg3Δ pdr1Δ pdr3Δ)) and inhibited degranulation of rat basophilic leukemia RBL-2H3 cells stimulated by immnunoglobulin G + 2,4-dinitrophenylated-bovine serum albumin (IgE+DNP-BSA), thapsigargin and A23187.
Assuntos
Ácidos Carboxílicos/farmacologia , Degranulação Celular/efeitos dos fármacos , Naftalenos/farmacologia , Saccharomyces cerevisiae/crescimento & desenvolvimento , Sesquiterpenos/farmacologia , Animais , Ácidos Carboxílicos/isolamento & purificação , Linhagem Celular Tumoral , Naftalenos/isolamento & purificação , Sesquiterpenos Policíclicos , Ratos , Saccharomyces cerevisiae/genética , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Xylariales/metabolismoRESUMO
A new compound, (3aS,6aR)-4,5-dimethyl-3,3a,6,6a-tetrahydro-2H-cyclopenta [b]furan-2-one (2), along with two known metabolites, myrotheciumone A (1) and 4-oxo-4H-pyron-3-acetic acid (3) was isolated from the ethyl acetate extract of fermentation broth of Xylaria curta 92092022. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HRESITOFMS, 1D NMR, and 2D NMR). Compounds 1 and 2 showed moderate antibacterial and phytotoxic activities.
Assuntos
Antibacterianos/farmacologia , Lactonas/química , Xylariales/química , Acetatos/química , Antibacterianos/química , Antifúngicos/química , Antifúngicos/farmacologia , Compostos Bicíclicos Heterocíclicos com Pontes/química , Compostos Bicíclicos Heterocíclicos com Pontes/isolamento & purificação , Compostos Bicíclicos Heterocíclicos com Pontes/farmacologia , Ciclopentanos/química , Avaliação Pré-Clínica de Medicamentos , Endófitos/química , Fermentação , Furanos/química , Lactonas/isolamento & purificação , Lactonas/farmacologia , Lactuca/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Pironas/química , Espectrofotometria Ultravioleta , Testes de ToxicidadeRESUMO
Seven previously undescribed bidesmosidic triterpenoid saponins named albidosides A - G, were isolated from a methanol extract of the roots of Acacia albida. Their structures were elucidated using 1D and 2D NMR spectroscopy and mass spectrometry and determined to be bidesmosides of oleanolic acid and of 16α-hydroxyoleanolic acid. Albidosides B - G were assayed for their cytotoxicity against HeLa and HL60 cells using MTT method and microscopic observation.
Assuntos
Acacia/química , Antineoplásicos Fitogênicos/isolamento & purificação , Ácido Oleanólico/análogos & derivados , Saponinas/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Camarões , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Células HeLa , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Raízes de Plantas/química , Saponinas/químicaRESUMO
Phytochemical investigation of the roots of Albizia chevalieri led to the isolation of two new 5-deoxyflavan-3,4-diol glucosides from roots of A. chevalieri, Chevalieriflavanosides A and B. Their structures were established by 2D NMR techniques, UV, IR, CD, and mass spectrometry. Cytotoxicity of the two compounds was evaluated against acute promyelocytic leukemia HL60 cells. The antibacterial activities of 1 and 2 also were evaluated against Pseudomonas aeruginosa and Staphylococcus aureus using the agar diffusion test. Copyright © 2016 John Wiley & Sons, Ltd.