Flavusides A and B, antibacterial cerebrosides from the marine-derived fungus Aspergillus flavus

Chem Pharm Bull (Tokyo). 2011;59(9):1174-7. doi: 10.1248/cpb.59.1174.

Abstract

Flavusides A (1) and B (2), two new antibacterial cerebroside derivatives, and the previously described phomaligol A (3), kojic acid (4), methyl kojic acid (5), and dimethyl kojic acid (6) have been isolated from the extract of a marine isolate of the fungus Aspergillus flavus. The structure and absolute stereochemistry of two cerebrosides were assigned on the basis of NMR and Tandem FAB-MS/MS experiments. Compounds 1, 2, and 3 exhibited a mild antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and multidrug-resistant S. aureus. The minimum inhibitory concentration (MIC) values for each strain are as follows: compounds 1 and 2 showed 15.6 μg/ml for S. aureus and 31.2 μg/ml for methicillin-resistant S. aureus and multidrug-resistant S. aureus, and compound 3 exhibited 31.2 μg/ml for S. aureus and methicillin-resistant S. aureus and 62.5 μg/ml for multidrug-resistant S. aureus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Aquatic Organisms / microbiology
  • Aspergillus flavus / chemistry*
  • Cerebrosides / chemistry*
  • Cerebrosides / isolation & purification
  • Cerebrosides / pharmacology
  • Drug Resistance, Bacterial / drug effects
  • Glycosphingolipids / chemistry*
  • Glycosphingolipids / isolation & purification
  • Glycosphingolipids / pharmacology
  • Magnetic Resonance Spectroscopy
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Staphylococcus aureus / drug effects
  • Tandem Mass Spectrometry

Substances

  • Anti-Bacterial Agents
  • Cerebrosides
  • Glycosphingolipids
  • flavuside A
  • flavuside B