Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

• Main Authors: Kazuki Watanabe, Yoshihiro Mimaki, Haruhiko Fukaya, Yukiko Matsuo
• Format: Article
• Language: English
• Published: MDPI AG 2018-12-01
• Series: Molecules
• Subjects: Eranthis cilicica; Ranunculaceae; cycloartane glycoside; oleanane glycoside; spectroscopic analysis; X-ray crystallographic analysis; apoptosis
• Online Access: http://www.mdpi.com/1420-3049/24/1/69

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.