New 23, 27-dihydroxy-oleanane-type triterpenoid saponins from Anemone Raddeana Regel

Nat Prod Res. 2021 Feb;35(3):384-391. doi: 10.1080/14786419.2019.1634708. Epub 2019 Jul 2.

Abstract

Two new 23, 27-dihydroxy-oleanane-type triterpenoid saponins named Raddeanoside Rf and Raddeanoside Rg (1 and 2), along with thirteen known triterpenoid saponins (3-15) were isolated from the rhizome of Anemone raddeana Regel. Their structures were determined by chemical and spectral analysis, including 1 D, 2 D NMR data and HRESIMS. The type of aglycone 23, 27-dihydroxy oleanolic acid is extremely rare in natural products. In addition, the anti-cancer activity for all the compounds were evaluated. Compounds 9 and 10 exhibited significant cytotoxicity with IC50 values of 4.47 and 8.97 μM against human pancreatic cancer lines (PANC-1), while compound 6 with IC50 value of 8.19 μM against human lung lines (A549). The possible structure-activity relationships of these triterpenoid saponins were also tentatively discussed.

Keywords: Anemone raddeana Regel; cytotoxicity; triterpenoid saponins.

MeSH terms

  • A549 Cells
  • Anemone / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Pancreatic Neoplasms / drug therapy
  • Pancreatic Neoplasms / pathology
  • Plant Extracts / chemistry
  • Rhizome / chemistry
  • Saponins / chemistry*
  • Saponins / pharmacology*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Plant Extracts
  • Saponins
  • Triterpenes
  • oleanane
  • Oleanolic Acid