Salimyxins and enhygrolides: antibiotic, sponge-related metabolites from the obligate marine myxobacterium Enhygromyxa salina

Chembiochem. 2013 Jul 22;14(11):1363-71. doi: 10.1002/cbic.201300268. Epub 2013 Jun 21.

Abstract

Unlike their terrestrial counterparts, marine myxobacteria are hardly investigated for their secondary metabolites. This study describes three new compounds (1-3), named salimyxins and enhygrolides, obtained from the obligate marine myxobacterium Enhygromyxa salina. These are the first natural products obtained from Enhygromyxa species. Their structures were elucidated by spectroscopic analysis, including NMR and CD spectroscopy. Enhygrolides are closely related to the nostoclides, which were initially isolated from a cyanobacterium of the genus Nostoc. The salimyxins, representing structurally most unusual degraded sterols, are close to identical to demethylincisterol from the sponge Homaxinella sp. Salimyxin B and enhygrolide A inhibit the growth of the Gram-positive bacterium Arthrobacter cristallopoietes (MIC salimyxin B, 8 μg mL⁻¹; enhygrolide A, 4 μg mL⁻¹).

Keywords: Enhygromyxa salina; marine; myxobacteria; natural products; structure elucidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Arthrobacter / drug effects
  • Benzylidene Compounds / chemistry*
  • Benzylidene Compounds / isolation & purification
  • Benzylidene Compounds / pharmacology
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Myxococcales / classification
  • Myxococcales / metabolism*
  • Phylogeny
  • Porifera / metabolism

Substances

  • Anti-Bacterial Agents
  • Benzylidene Compounds
  • Diterpenes
  • enhygrolide A
  • salimyxin B
  • 4-Butyrolactone