Three new anthraquinone derivatives isolated from Symplocos racemosa and their antibiofilm activity

Chin J Nat Med. 2017 Dec;15(12):944-949. doi: 10.1016/S1875-5364(18)30011-6.

Abstract

Three new alkyl substituted anthraquinone derivatives, trivially named as symploquinones A-C (Compounds 1-3) were isolated from Symplocos racemosa. The structures of these compounds were determined on the basis of extensive spectroscopic analyses (UV, IR, Mass, 1H- and 13C-NMR, and two-dimensional (2D) NMR techniques). The resulting data were also compared with the reported literature. These compounds were then subjected to antibacterial or antibiofilm testing. Compounds 1 and 3 exhibited good antibacterial activity in the concentration range of 160-83 μg·mL-1 against Streptococcus mutans, methicillin resistant Staphylococcus aureus and Proteus mirabilis. Both compounds were further screened for anti-biofilm activity, which revealed promising activities at sub-MIC concentrations. None of the compounds were found to be active against Klebsiella pneumoniae.

Keywords: Antibiofilm activity; Substituted anthraquinone; Symplocos racemosa.

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification
  • Anthraquinones / pharmacology*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Biofilms / drug effects*
  • Biofilms / growth & development
  • Ericales / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Methicillin-Resistant Staphylococcus aureus / drug effects*
  • Methicillin-Resistant Staphylococcus aureus / physiology
  • Microbial Sensitivity Tests
  • Proteus mirabilis / drug effects*
  • Proteus mirabilis / physiology
  • Spectrophotometry, Infrared
  • Streptococcus mutans / drug effects*
  • Streptococcus mutans / physiology

Substances

  • Anthraquinones
  • Anti-Bacterial Agents