Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis.

Abstract

Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of (1)D and (2)D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.

• Authors: Xiao-Yang Wang, Hui Gao, Wei Zhang, Yuan Li, Guang Cheng, Xiao-Li Sun, Hai-Feng Tang
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 23 Issue 20 Pg. 5714-20 (Oct 15 2013) ISSN: 1464-3405 [Electronic] England
• PMID: 23992864 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2013 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents, Phytogenic
• Saponins
• oleanane
• Oleanolic Acid

Topics

• Anemone (chemistry, metabolism)
• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, toxicity)
• Apoptosis (drug effects)
• Cell Line, Tumor
• Drug Screening Assays, Antitumor
• HL-60 Cells
• HeLa Cells
• Hep G2 Cells
• Humans
• Magnetic Resonance Spectroscopy
• Molecular Conformation
• Oleanolic Acid (analogs & derivatives, chemistry)
• Rhizome (chemistry, metabolism)
• Saponins (chemistry, isolation & purification, toxicity)
• Spectrometry, Mass, Electrospray Ionization