Hypocrol A, a new tyrosol derivative from a sponge-derived strain of the fungus Hypocrea koningii

Nat Prod Res. 2016 Jul;30(14):1633-8. doi: 10.1080/14786419.2015.1129333. Epub 2016 Feb 1.

Abstract

In continuation of our search for new antibacterial and antioxidant metabolites from sponge-derived fungi, one new tyrosol derivative, hypocrol A (1), together with four known congeners, trichodenol B (2), 4-hydroxyphenethyl acetate (3), 4-hydroxyphenethyl tetradecanoate (4) and 1-oleyltyrosol (5), was isolated from the strain Hypocrea koningii PF04. Their planar structures were unequivocally elucidated by spectroscopic methods and comparison with the literature data. All the compounds displayed weak antibacterial activities against Staphylococcus aureus, methicillin-resistant S. aureus and Escherichia coli, whereas compounds 1 and 2 exhibited a moderate antioxidant efficacy in the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assay with IC50 values of 48.5 and 97.4 μg/mL, respectively.

Keywords: Hypocrea koningii; antibacterial activity; antioxidant; tyrosol derivative.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / pharmacology
  • Antioxidants / pharmacology
  • Biphenyl Compounds
  • Chromatography, High Pressure Liquid
  • Escherichia coli / drug effects
  • Fermentation
  • Hypocrea / chemistry*
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / chemistry
  • Phenylethyl Alcohol / isolation & purification
  • Phenylethyl Alcohol / pharmacology
  • Picrates
  • Porifera / microbiology*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Biphenyl Compounds
  • Picrates
  • hypocrol A
  • 4-hydroxyphenylethanol
  • 1,1-diphenyl-2-picrylhydrazyl
  • Phenylethyl Alcohol