Triterpenoids from the leaves of Alphitonia xerocarpus Baill and their biological activity

Phytochemistry. 2016 Sep:129:45-57. doi: 10.1016/j.phytochem.2016.07.005. Epub 2016 Jul 21.

Abstract

Ten previously undescribed triterpenoid saponins and a previously undescribed norlupane triterpenoid were isolated, with three known saponins, four known flavonoids, two known lupane derivatives, sitosterol and 6'-heptadecanoyl-3-O-β-d-glucopyranosylsitosterol from the leaves of Alphitonia xerocarpus (Rhamnaceae), an endemic tree of New Caledonia. The chemical structures of the purified compounds were identified by nuclear magnetic resonance and mass spectrometry. The isolated compounds were tested for their antioxidant, antityrosinase, antibacterial and cytotoxic activity. The aqueous methanol extract showed antioxidant activity (DPPH assay) due to the presence of rutin. Ceanothenic acid showed good cytotoxic activity against a KB cell line (IC50 = 2.6 μM) and antibacterial activity against Staphylococcus aureus and Enterococcus faecalis with MIC values of 8 and 16 μg/mL, respectively. The previously undescribed 29-hydroxyceanothenic acid exhibited moderate cytotoxic activity (IC50 = 10 μM), good antibacterial activity against S. aureus (MIC = 4 μg/mL) and moderate antibacterial activity against E. faecalis (MIC = 16 μg/mL).

Keywords: Alphitonia xerocarpus; Flavonoids; Leaves; Norlupane; Rhamnaceae; Secodammarane; Triterpenoids.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Enterococcus faecalis / drug effects
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology*
  • Humans
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • New Caledonia
  • Plant Leaves / chemistry
  • Rhamnaceae / chemistry*
  • Saponins / chemistry
  • Saponins / isolation & purification
  • Saponins / pharmacology
  • Staphylococcus aureus / drug effects
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Flavonoids
  • Saponins
  • Triterpenes