ABSTRACT
A new isoflavanone, (3S)-5,7-dihydroxy-2',3',4'-trimethoxy-6,5'-diprenylisoflavanone (1) and eight known compounds including five flavones (2-6), two triterpenes (7-8) and a steroid (9) were isolated from the whole plant of Uraria crinita (Leguminosae). The structure of 1 was elucidated by detailed spectroscopic means including IR, HR-ESI-MS, 1D and 2D NMR, and CD data. Compounds 1-9 were evaluated for their cytotoxicity against four human cancer cell lines KB (mouth epidermal carcinoma), HepG2 (hepatocellular carcinoma), Lu (lung carcinoma) and MCF7 (breast carcinoma). Compound 1 showed cytotoxic activity against the tested cell lines with IC50 values of 33.2, 29.4, 59.6 and 66.8 µM, respectively.
Subject(s)
Fabaceae/chemistry , Isoflavones/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Carbon-13 Magnetic Resonance Spectroscopy , Cell Death/drug effects , Cell Line, Tumor , Humans , Isoflavones/chemistry , Isoflavones/pharmacology , Proton Magnetic Resonance SpectroscopyABSTRACT
Repeated column chromatography of the n-hexane extract of Ficus hirta leaves (Moraceae) led to isolation of a new oleanane triterpene, 3ß-hydroxy-11-oxo-olean-12-enyl-3-stearate (1) in addition to three known compounds, taraxerol (2), 3ß-acetoxy-11α-methoxy-12-ursene (3) and 3ß-acetoxy-11α-hydroxy-12-ursene (4). Their structures were elucidated by spectroscopic methods and by comparison with data reported in the literatures.
Subject(s)
Ficus/chemistry , Oleanolic Acid/analogs & derivatives , Triterpenes/isolation & purification , Molecular Structure , Oleanolic Acid/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , Spectrum AnalysisABSTRACT
OBJECTIVE: To investigate the anti-proliferative effects of 20-hydroxyecdysone isolated from the bark of Dacrycarpus imbricatus (Blume) de Laub. METHODS: Column chromatography was used for isolation of compounds from plant material. The structure of the isolated compound was identified by mass spectrometry and nuclear magnetic resonance techniques, including HSQC, HMBC, NOE-difference experiments. The isolated compound was tested for its anti-proliferative activity in acute myeloid leukemia (AML) and OCI-AML cells. RESULTS: Compound 1 was isolated from the ethyl acetate fraction of Dacrycarpus imbricatus barks by column chromatography. Its chemical structure was identified as 20-hydroxyecdysone (20HE), a cholestane-type ecdysteroid, by a combination of mass spectrometry and nuclear magnetic resonance spectrometric analyses. Our goal was to test the anti-proliferative activity of 20HE using the OCI-AML cell line. 20HE significantly decreased OCI cell number at a concentration of 1 mg/mL, whereas lower concentrations were ineffective. Moreover, this decrease was due to partial blockage of the G1/S phase of the cell cycle, with a reduction of cells in the G2M phase, not due to increased apoptosis. CONCLUSIONS: This indicates that 20HE significantly decreases the number of cells in the G1/S phase of the cell cycle in human AML cells. This is the first time that the anti-proliferative activity of 20HE against a human tumor cell line has been reported.