Antimicrobial and antioxidant effects of phenolic constituents from Klainedoxa gabonensis

Pharm Biol. 2010 Oct;48(10):1124-9. doi: 10.3109/13880200903486644.

Abstract

Bioassay-guided fractionation of the methanol extract of the stem bark of Klainedoxa gabonensis Pierre ex Engl. (Irvingiaceae) afforded 12 compounds, namely, ellagic acid (1), ellagic acid 3,3'-dimethylether (2), gallic acid (3), methyl gallate (4), lupeol (5), β-amyrin (7), erythrodiol (8), oleanolic acid (9), betulinic acid (6), hederagenin (10), bayogenin acid (11), and stigmasterol-3-O-β-d-glucopyranoside (12). Compounds 1-3 and 7-12 were isolated for the first time from this genus. The structures were established on the basis of 1D/2D NMR experiments and mass spectrometric data. Crude extract, fractions (A, B, C and D) and pure compounds were tested for their antimicrobial activity using paper disk agar diffusion assay. The test delivered a range of low to high activities for phenolic compounds 1-4, low or missing activities for terpenoid compounds 5-11, and impressive very high antibacterial/antifungal values for two fractions C and D probably due to synergistic effects of compounds. The broth microdilution assay revealed MICs of 15.4-115.1 μg/mL for phenolic compounds, MICs higher than 1 mg/mL for terpenoids and MICs of 4.5-30.3 μg/mL for fractions C and D. The determination of the radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay gave high antioxidant values for the methanol extract and fraction D (IC(50) 10.45 and 5.50 μg/mL) as well as for the phenolic compounds 1-4 (IC(50) 45.50-48.25 mM) compared to the standard 3-t-butyl-4-hydroxyanisole (BHA) (IC(50) 44.20 mM).

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / chemistry
  • Microbial Sensitivity Tests
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Picrates / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Roots / chemistry
  • Streptophyta / chemistry*

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal Agents
  • Antioxidants
  • Biphenyl Compounds
  • Phenols
  • Picrates
  • Plant Extracts
  • 1,1-diphenyl-2-picrylhydrazyl