RESUMO
Four new monacolin analogs, monacolin T (1), monacolin U (2) 6a-O-methyl-4,6-dihydromonacolin L (3), and 6a-O-ethyl-4,6-dihydromonacolin L (4) were isolated from the ethanolic extract of Monascus purpureus-fermented rice. Their structures were determined by a combination of 1D, 2D NMR experiments (1H-1HCOSY, HSQC, HMBC, and ROESY), and mass spectrometry. In vitro cytotoxic assay, all compounds were inactive at the concentration of 10 µM.
Assuntos
Monascus/química , Naftalenos/isolamento & purificação , Oryza/microbiologia , Ensaios de Seleção de Medicamentos Antitumorais , Fermentação , Estrutura Molecular , Naftalenos/químicaRESUMO
OBJECTIVE: To analyze the chemical constituents of low polar components from ethanol extract of Ainsliaea yunnanensis. METHODS: The air-dried stems and leaves of Ainsliaea yunnanensis were extracted with ethanol using ultrasonic extration. After removal of solvent under reduced pressure, the residue was suspended in H2O, and then partitioned sequentially with petroleum ether, EtOAc and n-BuOH, respectively. Then the petroleum ether fraction was chromatographed on normal phase silica gels eluting with a gradient increasing Me2 CO in petroleum ether. Then the components of low polarity were separated from the petroleum ether-Me2CO(50:1 - 20: 1) fraction and identified by GC-MS, and the relative contents of the components were determined with area percentage method. RESULTS: 50 constituents were identified from the low polar components of Ainsliaea yunnanensis. CONCLUSION: The research provides a theoretical basis for the study of chemical constituents and pharmaceutical activities of Ainsliaea yunnanensis.
Assuntos
Antioxidantes/análise , Asteraceae/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Terpenos/análise , Anti-Inflamatórios não Esteroides/análise , Anti-Inflamatórios não Esteroides/isolamento & purificação , Antioxidantes/isolamento & purificação , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Solventes/química , Terpenos/isolamento & purificaçãoRESUMO
Two new monacolin analogs, monacolins O (1) and P (2), along with three known analogs, have been isolated from the ethanolic extract of Monascus purpureus-fermented rice. Their structures and absolute configurations were elucidated by spectroscopic methods, especially 2D NMR and CD spectral analyses as well as chemical method. Both 1 and 2 were tested against five tumor cell lines, and compound 1 exhibited selective cytotoxic activity against A2780 and A549 cell lines, with IC50 values of 3.7 and 8.0 µM, respectively.
Assuntos
Antineoplásicos/isolamento & purificação , Monascus/química , Naftalenos/isolamento & purificação , Oryza/microbiologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Fermentação , Humanos , Estrutura Molecular , Naftalenos/química , Naftalenos/farmacologia , Ressonância Magnética Nuclear Biomolecular , Oryza/metabolismoRESUMO
The compounds of Ainsliaea yunnanensis were isolated and purified by various kinds of column chromatography methods and their structures were determined by spectroscopic data analysis. Twelve compounds were obtained from the petroleum ether of ethanolic extract of A. yunnanensis and elucidated as bauerenyl acetate (1), bauerenol (2), alpha-amyrin (3), psi-taraxasterol (4), beta-amyrin (5), echinocystic acid (6), multiflorenol (7), 3beta-hydroxy-olean-18-ene germanicol (8), 3beta-hexadecanoyl-12-oleanen-11-one (9), fernenol (10), fern-7-en-3beta-ol (11), and lupeol (12). All compounds were isolated from this genus for the first time except compound 1, 3, 5 and 10, and they were all isolated from this plant for the first time.
Assuntos
Asteraceae/química , Medicamentos de Ervas Chinesas/química , Triterpenos/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Triterpenos/isolamento & purificaçãoRESUMO
One unusual aromatic monacolin analog, aromonacolin A (1), was isolated from the ethanolic extract of Monascus purpureus-fermented rice. Its structure was elucidated by extensive spectroscopic (HRESIMS, (1)H NMR, (13)C NMR, HSQC, HMBC, and NOESY) and chemical methods. The absolute configuration of the C-6 secondary alcohol was deduced via the circular dichroism data of the in situ formed [Rh(2)(OCOCF(3))(4)] complex.