RESUMO
Phytochemical investigation on the stems of Strophanthus divaricatus led to the isolation of four undescribed cardiac glycosides and one undescribed C21 pregnane, together with eleven known steroids. Their structures were elucidated by a comprehensive analysis of HRESIMS, 1D and 2D NMR spectra. The absolute configuration of 16 was determined by comparison of the experimental and computed ECD spectra. Compounds 1-13 and 15 displayed potent to significant cytotoxicity against human cancer cell lines K562, SGC-7901, A549 and HeLa with IC50 values of 0.02-16.08, 0.04-23.13, 0.06-22.31 and 0.06-15.13 µM, respectively.
Assuntos
Antineoplásicos , Strophanthus , Humanos , Glicosídeos/química , Pregnanos/farmacologia , Pregnanos/química , Linhagem Celular Tumoral , Estrutura MolecularRESUMO
To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC50 values of 7.62, 6.28, and 3.55 µM, respectively.
Assuntos
Carpóforos/química , Ganoderma/química , Lanosterol/análogos & derivados , Triterpenos/isolamento & purificação , Humanos , Concentração Inibidora 50 , Lanosterol/química , Lanosterol/isolamento & purificação , Lanosterol/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Triterpenos/química , Triterpenos/farmacologiaRESUMO
The chemical investigation on the fruiting bodies of Amauroderma subresinosum led to the isolation of 10 compounds including 2 new ones named amaurosubresin (1) and erythro(23,24)-5α,6α-epoxyergosta-8-ene-7-one-3ß,23-diol (2). Their structures were elucidated on the basis of 1D and 2D NMR spectroscopy as well as MS. The bioassay of inhibitory activity against acetylcholinesterase (AChE) of two new isolates exhibited definite inhibitory activity.
Assuntos
Acetilcolinesterase/efeitos dos fármacos , Inibidores da Colinesterase/isolamento & purificação , Ergosterol/análogos & derivados , Hidroquinonas/isolamento & purificação , Polyporales/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Ergosterol/química , Ergosterol/isolamento & purificação , Ergosterol/farmacologia , Carpóforos/química , Hidroquinonas/química , Hidroquinonas/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Twelve lanostane triterpenoids (1-12) including a new one 16α,26-dihydroxylanosta-8,24-dien-3-one (1) were isolated from the fruiting bodies of Ganoderma hainanense. The structure of the new compound was elucidated by 1D and 2D NMR and MS spectroscopic analyses. All isolates were evaluated for their cytotoxicities against human tumor cell lines K-562, SMMC-7721, and SGC-7901 and five compounds (1, 2, 5,7, and 9) showed definite cytotoxicities against K-562 cell line. Meanwhile, compounds 2, 5,7, and 9 exhibited cytotoxic activities against SMMC-7721 and SGC-7901 cell lines.
Assuntos
Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Ganoderma/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Antineoplásicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Carpóforos/química , Humanos , Células K562 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Triterpenos/químicaRESUMO
One new compound named amauroamoienin (1), together with thirteen known compounds (2-14), was isolated from the EtOAc extract of Amauroderma amoiensis. The structures of these compounds were elucidated by the analysis of 1D and 2D spectroscopic data and the MS technique. The bioassays of inhibitory activities of these isolates against acetylcholinesterase were evaluated, and compounds 1, 3, and 5 exhibited acetylcholinesterase inhibitory activities.
Assuntos
Inibidores da Colinesterase/farmacologia , Compostos Heterocíclicos de 4 ou mais Anéis/farmacologia , Extratos Vegetais/farmacologia , Polyporales/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Eritrócitos/enzimologia , Compostos Heterocíclicos de 4 ou mais Anéis/química , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Humanos , Técnicas In Vitro , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificaçãoRESUMO
Three new sesquiterpenes dobinins A-C (1-3), together with five known compounds, were isolated from the root of Dobinea delavayi. The structures of the three new compounds were determined on the basis of spectroscopic analysis including 1D-, 2D-NMR and MS techniques as well as by comparison of the spectral data with those of analogous compounds reported in the literatures. Compounds 1-3 were screened for antitumor activity in vitro and exhibited definite cytotoxic activity against the human tumor cell line HL-60 with IC50 levels of 8.0 × 10-5, 4.7 × 10-5, and 5.1 × 10-5 M, respectively.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Leucemia/tratamento farmacológico , Neoplasias Pulmonares/tratamento farmacológico , Sapindaceae/química , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Citotoxinas/isolamento & purificação , Células HL-60 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Raízes de Plantas/química , Plantas Medicinais/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Seven previously unreported daphnane-type diterpene esters named acutilobins A-G, together with 12 known ones, were isolated from EtOAc extract of Daphne acutiloba Rehd. Their structures were elucidated based on the spectroscopic data. The cytotoxic and anti-HIV-1 activities of these daphnane-type diterpene esters were evaluated through bioassays. Fourteen of these isolates exhibited definite cytotoxic activities against the five human tumor cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480. Additionally, anti-HIV-1 activities were observed in 13 daphnane-type diterpene esters, among which acutilobins A-G exhibited significant anti-HIV-1 activities with EC50 below 1.5 nM and SI over 10,000. Particularly, genkwanineVIII showed the strongest activity with EC50 0.17 nM and SI 187,010.
Assuntos
Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Daphne/química , Diterpenos/farmacologia , Ésteres/farmacologia , HIV-1/efeitos dos fármacos , Extratos Vegetais/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Ésteres/química , Ésteres/isolamento & purificação , Células HL-60 , Humanos , Conformação Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
Two new guaiane-type sesquiterpenoids, valerol A (1) and kessyl 3-acetate (2), together with nine known compounds, valeracetate (3), anismol A (4), orientalol C (5), spatulenol (6), 4α,10α-epoxyaromadendrane (7), (+)-8-hydroxypinoresinol (8), pinorespiol (9), pinoresinol 4-O-ß-D-glucopyranoside (10), and 8-hydroxypinoresinol 4'-O-ß-D-glucopyranoside (11) were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1 and 2 were elucidated on the basis of spectroscopic methods (1D- and 2D-NMR, MS, UV, and IR). These compounds were evaluated for inhibitory activity on acetylcholinesterase (AChE) and enhancing activity on nerve growth factor (NGF)-mediated neurite outgrowth in PC12 cells.
Assuntos
Lignanas/química , Lignanas/farmacologia , Plantas Medicinais/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Valeriana/química , Animais , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Avaliação Pré-Clínica de Medicamentos , Glucosídeos/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fator de Crescimento Neural/fisiologia , Neuritos/efeitos dos fármacos , Células PC12 , Raízes de Plantas/química , Ratos , Sesquiterpenos de Guaiano/químicaRESUMO
OBJECTIVE: To study the chemical constituents of the herb of Antenoron filiforme. METHODS: The constituents were separated by column chromatography and their structures were elucidated by spectral data analyses. RESULTS: Eleven compounds were isolated from the ethanol extract of A. filiforme and identified as, bronane-5-hydroxy-2-O-beta-D-glucopyranoside (I), adenosine (II), bonaroside (III), rhamnetin (IV), hyperoside (V), rhamnetin-3-O-beta-D-galactopyranoside (VI), kaempferol-3, 7-O-bis-alpha-L-rhamnopyranoside (VII), stigmasterol (VIII), nonacosanoic acid (IX), daucosterol (X), 3beta-sitosterol (XI). CONCLUSION: All compounds are obtained from A. filiforme for the first time.
Assuntos
Flavonóis/isolamento & purificação , Glucosídeos/isolamento & purificação , Polygonaceae/química , Sitosteroides/isolamento & purificação , Adenosina/química , Adenosina/isolamento & purificação , Flavonóis/química , Glucosídeos/química , Estrutura Molecular , Plantas Medicinais/química , Quercetina/análogos & derivados , Quercetina/química , Quercetina/isolamento & purificação , Sitosteroides/química , Estigmasterol/química , Estigmasterol/isolamento & purificaçãoRESUMO
Natural inhibitors of fatty acid synthase (FAS) are emerging as potential therapeutic agents to treat cancer and obesity. The bioassay-guided chemical investigation of the hulls of Garcinia mangostana led to the isolation of 13 phenolic compounds (1-13) mainly including xanthone and benzophenone, in which compounds 7, 8, 9, 10, and 11 were isolated from this plant for the first time and compound 9 was a new natural product. These isolates possess strong inhibitory activity of FAS with the IC(50) values ranging from 1.24 to 91.07 µM. The study indicates that two types of natural products, xanthones and benzophenones, could be considered as promising FAS inhibitors.