Hyaladione, an S-methyl cyclohexadiene-dione from Hyalangium minutum

J Nat Prod. 2012 Apr 27;75(4):768-70. doi: 10.1021/np200776v. Epub 2012 Apr 12.

Abstract

A bioassay-guided fractionation of the crude methanol extract of the myxobacterium Hyalangium minutum, strain NOCB-2(T) (DSM 14724(T)), led to the isolation of hyaladione (1), a novel S-methyl cyclohexadiene-dione. The structure of 1 was established by HRESIMS, NMR, and IR spectroscopy as well as X-ray crystallography. Compound 1 was active against growing mammalian cell lines, with IC(50) values ranging from 1.23 to 3.93 μM, in addition to a broad spectrum of antibacterial and antifungal activities, including inhibition of pathogenic methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa with an MIC of 0.83 and 8.5 μg mL(-1), respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Crystallography, X-Ray
  • Cyclohexenes / chemistry
  • Cyclohexenes / isolation & purification*
  • Cyclohexenes / pharmacology
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Myxococcales / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Pseudomonas aeruginosa / drug effects

Substances

  • Anti-Bacterial Agents
  • Cyclohexenes
  • hyaladione
  • 1,4-cyclohexadiene