Chemical constituents from leaves and trunk bark of Rinorea oblongifolia (Violaceae)

Nat Prod Res. 2020 Jul;34(14):2014-2021. doi: 10.1080/14786419.2019.1573230. Epub 2019 Feb 20.

Abstract

Two new coruleoellagic acid derivatives, 3,4',5,5',-tetramethylcoruleoellagic acid (1); 3',4,4',5,5'-pentamethylcoruleoellagic acid (2) and a new friedelane-type triterpene derivative rinol (5), were isolated from leaves and trunk bark of Rinorea oblongifolia (Violaceae) along with seven known compounds including 3,3',4,4',5'-pentamethylcoruleoellagic acid (3), hexamethylcoruleoellagic acid (4), 28-hydroxyfriedelin (6), friedelin (7), friedelan-3-ol (8), scopoletin (9) and β-sitosterol-3-O-β-D-glucopyranoside (10). Their structures were elucidated by means of spectroscopic methods including IR, 1D and 2D NMR in conjunction with mass spectrometry. Crude extracts of leaves and trunk bark as well as compounds 1-4 were evaluated for their antibacterial activities against 7 pathogenic bacterial strains (Streptococcus pneumoniae ATCC49619, Staphylococcus aureus ATCC 43300, Klepsiella pneumoniae ATCC 700603, Haemophilus influenza ATCC 49247, Escherichia coli ATCC 25922, Pseudomonas aeruginosa HM601, Staphylococcus aureus BAA 977). Compound (3) displayed noteworthy activity against Haemophilus influenza with MIC value of 9.38 µg/mL.

Keywords: Rinorea oblongifolia; antibacterial activity; coruleoellagic acid; friedelane-type triterpene.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Bacteria / drug effects
  • Haemophilus influenzae / drug effects
  • Microbial Sensitivity Tests
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry*
  • Triterpenes / analysis
  • Triterpenes / isolation & purification
  • Violaceae / chemistry*

Substances

  • Anti-Bacterial Agents
  • Plant Extracts
  • Triterpenes
  • friedelan-3-ol
  • friedelane
  • friedelin