Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Phytochemical analysis of the tubers of was performed as part of our continuous study on the plants of the family , which resulted in the isolation of eleven new cycloartane glycosides ( ⁻ ) and one new oleanane glycoside ( ), together with one known oleanane glycoside ( ). The structures of the new...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2018-12, Vol.24 (1), p.69
Main Authors: Watanabe, Kazuki, Mimaki, Yoshihiro, Fukaya, Haruhiko, Matsuo, Yukiko
Format: Article
Language:English
Subjects:
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Apoptosis
Carbon
Cell death
Cell Survival - drug effects
Chromatography
Crystallography
cycloartane glycoside
Cytology
Cytotoxicity
Eranthis
Eranthis cilicica
Glucose
Glycosides
Glycosides - chemistry
Glycosides - pharmacology
HL-60 Cells
Humans
Leukemia
NMR
Nuclear magnetic resonance
oleanane glycoside
Oleanolic Acid - analogs & derivatives
Oleanolic Acid - chemistry
Oleanolic Acid - pharmacology
Phytochemicals
Plant Tubers - chemistry
Ranunculaceae
Ranunculaceae - metabolism
spectroscopic analysis
Spectrum analysis
Triterpenes - chemistry
Tubers
Two dimensional analysis
X-ray crystallographic analysis
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Summary:Phytochemical analysis of the tubers of was performed as part of our continuous study on the plants of the family , which resulted in the isolation of eleven new cycloartane glycosides ( ⁻ ) and one new oleanane glycoside ( ), together with one known oleanane glycoside ( ). 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 ( ) of and its C-23 epimer ( ), and the oleanane glycosides ( and ) showed cytotoxic activity against HL-60 leukemia cells with IC values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to (IC 14.8 μM) than (IC 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 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 .
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24010069