Cytotoxic Oleanane-Type Saponins from the Leaves of Albizia anthelmintica Brongn

Chem Biodivers. 2016 Dec;13(12):1666-1673. doi: 10.1002/cbdv.201600102. Epub 2016 Nov 16.

Abstract

Two new oleanane-type saponins: β-d-xylopyranosyl-(1 → 4)-6-deoxy-α-l-mannopyranosyl-(1 → 2)-1-O-{(3β)-28-oxo-3-[(2-O-β-d-xylopyranosyl-β-d-glucopyranosyl)oxy]olean-12-en-28-yl}-β-d-glucopyranose (1) and 1-O-[(3β)-28-oxo-3-{[β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 6)-2-acetamido-2-deoxy-β-d-glucopyranosyl]oxy}olean-12-en-28-yl]β-d-glucopyranose (2), along with two known saponins: (3β)-3-[(β-d-Glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)oxy]olean-12-en-28-oic acid (3) and (3β)-3-{[α-l-arabinopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]oxy}olean-12-en-28-oic acid (4) were isolated from the acetone-insoluble fraction obtained from the 80% aqueous MeOH extract of Albizia anthelmintica Brongn. leaves. Their structures were identified using different NMR experiments including: 1 H- and 13 C-NMR, HSQC, HMBC and 1 H,1 H-COSY, together with HR-ESI-MS/MS, as well as by acid hydrolysis. The four isolated saponins and the fractions of the extract exhibited cytotoxic activity against HepG-2 and HCT-116 cell lines. Compound 2 showed the most potent cytotoxic activity among the other tested compounds against the HepG2 cell line with an IC50 value of 3.60μm. Whereas, compound 1 showed the most potent cytotoxic effect with an IC50 value of 4.75μm on HCT-116 cells.

Keywords: Albizia anthelmintica; Cytotoxicity; Fabaceae; MTT assay; Oleanane saponins.

MeSH terms

  • Albizzia / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • Hep G2 Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Conformation
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Plant Leaves / chemistry*
  • Saponins / chemistry
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Structure-Activity Relationship

Substances

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