Abstract
Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.
Highlights
We report the structural determination of the new compounds by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis, followed by either X-ray crystallographic or chromatographic analysis
The MeOH extract of the E. cilicica tubers was allowed to pass through the porous-polymer polystyrene resin (Diaion HP-20) column, and a series of chromatographic separations of the glycoside-enriched fraction using column chromatography (CC) on silica gel and octadecylsilanized (ODS) silica gel were performed to obtain compounds 1–13 (Figure 1)
The known compound 12 was identified as 3β-[(O-β-D-glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-23hydroxyolean-12-en-28-oic acid by direct comparison with an authentic sample isolated from Anemone coronaria [6]
Summary
We carried out systematic phytochemical screenings of the plants belonging to the family. Ranunculaceae, such as the Adonis [1,2,3,4], Anemone [5,6], Cimicifuga [7,8], Clematis [9], Helleborus [10,11,12,13,14], and Pulsatilla species [15,16], and isolated various triterpene and steroidal glycosides, including cardiac and pregnane glycosides. As part of our ongoing phytochemical study of Ranunculaceae plants, the cytotoxic activity of the cycloartane-type glycosides 2 and 8, the aglycone 1a and its C-23 epimer 8a, and the oleanane-type triterpene glycosides.
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
