Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis

Bioorg Med Chem Lett. 2013 Oct 15;23(20):5714-20. doi: 10.1016/j.bmcl.2013.08.006. Epub 2013 Aug 11.

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.

Keywords: Anemone taipaiensis; Cytotoxicity; Ranunculaceae; Triterpenoid saponin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anemone / chemistry*
  • Anemone / metabolism
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / 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*
  • Oleanolic Acid / chemistry
  • Rhizome / chemistry*
  • Rhizome / metabolism
  • Saponins / chemistry*
  • Saponins / isolation & purification
  • Saponins / toxicity
  • Spectrometry, Mass, Electrospray Ionization

Substances

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