Borrelidins C-E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp

Mar Drugs. 2017 Jun 6;15(6):166. doi: 10.3390/md15060166.

Abstract

Chemical investigation of a halophilic actinomycete strain belonging to the genus Nocardiopsis inhabiting a hypersaline saltern led to the discovery of new 18-membered macrolides with nitrile functionality, borrelidins C-E (1-3), along with a previously reported borrelidin (4). The planar structures of borrelidins C-E, which are new members of the rare borrelidin class of antibiotics, were elucidated by NMR, mass, IR, and UV spectroscopic analyses. The configurations of borrelidines C-E were determined by the interpretation of ROESY NMR spectra, J-based configuration analysis, a modified Mosher's method, and CD spectroscopic analysis. Borrelidins C and D displayed inhibitory activity, particularly against the Gram-negative pathogen Salmonella enterica, and moderate cytotoxicity against the SNU638 and K562 carcinoma cell lines.

Keywords: Salmonella enterica; antibacterial; borrelidin; halophilic actinomycetes; saltern.

MeSH terms

  • Actinobacteria / chemistry*
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Cell Line, Tumor
  • Fatty Alcohols / chemistry
  • Fatty Alcohols / pharmacology
  • Humans
  • K562 Cells
  • Macrolides / chemistry*
  • Macrolides / pharmacology
  • Salmonella enterica / drug effects
  • Spectrum Analysis / methods

Substances

  • Anti-Bacterial Agents
  • Fatty Alcohols
  • Macrolides
  • borrelidin