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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 IC 50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC 50 14.8 μM) than 1a (IC 50 101.1 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 .

Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica