RESUMO
Objective: To study the non-alkaloid chemical constituents of Macleaya cordata. Methods: Alcohol extraction and liquidliquid partitionmethods were used to extract the chemical constituents. Silica gel,reverse-phase octadecylsilyl( ODS), and Sephadex LH-20 column chromatographic methods were applied for isolation and purification. Spectroscopic methods including MS and NMR were used to determine their structures. Results: Eleven non-alkaloid compounds were isolated from the fruits of Macleaya cordata, and their structures were identified as 3-( 3,4-dihydroxy) phenylpropanoic acid methyl ester( 1),ferulic acid( 2),1-octacosanol( 3),syringic acid( 4),p-hydroxy-benzoic acid( 5),p-coumaric acid( 6),quercetin-3-O-ß-D-glucoside( 7),N-p-coumaroyl tyramine( 8),10-eicosenoic acid( 9) and ß-sitosterol( 10) and daucosterol( 11). Conclusion: Compounds 1,3 ~9 are isolated from Macleaya cordata for the first time.
Assuntos
Papaveraceae , Alcaloides , Ácidos Cumáricos , Ácido Gálico/análogos & derivados , Glucosídeos , Quercetina , Sitosteroides , Tiramina/análogos & derivadosRESUMO
A new cytotoxic benzophenanthridine isoquinoline alkaloid, named cordatine (1), together with one known alkaloid 8-methoxydihydrochelerythrine (2), was isolated from the fruits of Macleaya cordata. The structure of the new compound was elucidated by spectroscopic methods including 1D and 2D NMR, HR-ESI-MS. Both compounds indicated significant cytotoxicity against MCF-7 and SF-268 cell lines.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Benzofenantridinas/isolamento & purificação , Benzofenantridinas/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Frutas/química , Papaveraceae/química , Alcaloides/química , Antineoplásicos Fitogênicos/química , Benzofenantridinas/química , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Humanos , Isoquinolinas , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Two new ent-kaurane diterpene glycosides, ranunculosides A (1) and B (2), and a new benzophenone, ranunculone C (3), were isolated from the aerial part of Ranunculus muricatus Linn. The chemical structures of compounds 1-3 were established to be (2S)-ent-kauran-2ß-ol-15-en-14-O-ß-d-glucopyranoside, (2S,4S)-ent-kauran-2ß,18-diol-15-en-14-O-ß-d-glucopyranoside, and (R)-3-[2-(3,4-dihydroxybenzoyl)-4,5-dihydroxy-phenyl]-2-hydroxylpropanoic acid, respectively, by spectroscopic data and chemical methods. The absolute configuration of 1 was determined by the combinational application of RP-HPLC analysis and Mosher's method.
Assuntos
Benzofenonas/isolamento & purificação , Diterpenos/isolamento & purificação , Glicosídeos/isolamento & purificação , Ranunculus/química , Benzofenonas/química , Cromatografia Líquida de Alta Pressão , Diterpenos/química , Glicosídeos/química , Conformação Molecular , Extratos VegetaisRESUMO
OBJECTIVE: To study the alkaloids of Macleaya cordata and their anti-tumor activities. METHOD: Alcohol and liquid-liquid extraction were used methods were used to extract the alkaloids constituents, and silica gel, reverse-phase octadecylsilyl (ODS), sephadex LH-20 chromatographic methods and HPLC were applied to isolate and purify compounds. MS, NMR spectroscopic methods were used to determine their structures. Furthermore, the cytotoxicity of these chemical components for MCF-7 and SF-268 cell lines was measured by MTT method. RESULT: Twelve alkaloids were isolated from the fruits of M. cordata, and their structures were identified as: maclekarpine E (1), 6-acetonyldihyrochelerythrine (2), cavidilinine (3), 6-acetonyldihyrosanguinnarine (4), O-methylzanthoxyline (5), 6-methoxy-dihydrosanguinarine (6), spallidamine (7), 6-hydroxyldihydrochelerythrine (8), arnotianamida (9), dihydrosanguinarine (10), protopine (11), and cryptopine (12). CONCLUSION: Compounds 1, 3, 7-9 were isolated from M. cordata for the first time, and compound 5 is a new natural product. The results of cytotoxic assay indicated that compound 6 showed strong cytotoxicity against MCF-7 and SF-268 cell lines with IC50 values of 0.61 µmol · L(-1) and 0.54 µmol · L(-1), respectively.
Assuntos
Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Papaveraceae/química , Alcaloides/farmacologia , Linhagem Celular Tumoral , HumanosRESUMO
The chemical constituents of 95% ethanol extract of Melastoma dodecandrum were isolated and purified by chromatography on silica gel, Sephadex LH-20, and HPLC, to obtain thirteen compounds eventually. On the basis of their physico-chemical properties and spectroscopic data, these compounds were identified as quercetin (1), quercetin-3-O-ß-D-glucopyranoside (2), quercetin-3-O-(6"-O-p-coumaroyl) -ß-D-glucopyranoside (3), kaempferol (4), kaempferol-3-O-ß-D-glucopyranoside (5), kaempferol-3-O- [2",6"-di-O-(E)-coumaroyl]-ß-D-glucopyra-noside (6), luteolin (7), luteolin-7-O-(6"-p-coumaroyl) -ß-D-glucopyranoside (8), apigenin (9), apigenin-7-(6"-acetyl-glucopyranoside) (10) , naringenin (11), isovitexin (12), and epicatechin-[8,7-e] -4ß-(4-hydroxyphenyl)-3,4-dyhydroxyl-2(3H)-pyranone (13). Eight compounds(3,5,6,8-11 and 13) were obtained from M. dodecandrum for the first time.
Assuntos
Flavonoides/análise , Glicosídeos/análise , Magnoliopsida/química , Plantas Medicinais/química , Apigenina/análise , Cromatografia/métodos , Cromatografia Líquida de Alta Pressão , Dextranos , Flavanonas/análise , Flavonoides/química , Glicosídeos/química , Quempferóis/análise , Luteolina/análise , Quercetina/análise , Sílica GelRESUMO
Three new iridoid glycosides, 6â³-O-trans-feruloylgenipin gentiobioside (1), 2'-O-trans-p-coumaroylgardoside (2), 2'-O-trans-feruloylgardoside (3), were isolated from the fruit of Gardenia jasminoides var. radicans MAKINO (Rubiaceae). The structures of these compounds were elucidated on the basis of MS, NMR spectra analysis, glycoside hydrolysis, and sugar derivatization coupled with HPLC analysis.