Disulfides with Anti-inflammatory Activity from the Brown Alga Dictyopteris membranacea

J Nat Prod. 2016 Mar 25;79(3):584-9. doi: 10.1021/acs.jnatprod.5b01031. Epub 2016 Mar 4.

Abstract

Six new (1, 2, and 4-7) and two previously reported (3 and 8) disulfides, along with 4-butyl-2,6-cycloheptadienone, γ-tocopherol, and δ-tocopherol, were isolated from an organic extract of the brown alga Dictyopteris membranacea, collected at Gerolimenas Bay, Greece. The structure elucidation of the isolated natural products was based on analysis of their spectroscopic data. Compounds 1, 3-6, and 8 were evaluated for their antibacterial and anti-inflammatory activities. None of the compounds displayed antibacterial activity against two resistant strains of Staphylococcus aureus and one strain of Escherichia coli. In contrast, metabolite 5 was able to cause strong inhibition of NO production with an IC50 value of 3.8 μM using an LPS stimulation assay.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology*
  • Disulfides / chemistry
  • Disulfides / isolation & purification*
  • Disulfides / pharmacology*
  • Escherichia coli / drug effects
  • Greece
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Phaeophyceae / chemistry*
  • Staphylococcus aureus / drug effects
  • Tocopherols

Substances

  • Anti-Bacterial Agents
  • Anti-Inflammatory Agents
  • Disulfides
  • Lipopolysaccharides
  • Nitric Oxide
  • delta-tocopherol
  • Tocopherols