Sinefungin VA and dehydrosinefungin V, new antitrypanosomal antibiotics produced by Streptomyces sp. K05-0178

J Antibiot (Tokyo). 2010 Nov;63(11):673-9. doi: 10.1038/ja.2010.102. Epub 2010 Sep 22.

Abstract

Two new nucleotide antibiotics, named sinefungin VA and dehydrosinefungin V, were separated by cation exchange column chromatography and purified by HPLC from the culture broth of Streptomyces sp. K05-0178, together with the known antibiotics, sinefungin, dehydrosinefungin and KSA-9342. The structures of the two novel sinefungin analogs were elucidated by spectroscopic studies, including various NMR and advanced peptide chemical methods. Sinefungin VA consists of adenosine and ornithylvalylalanine, whereas dehydrosinefungin V consists of 4',5'-dehydroadenosine and ornithylvaline. Sinefungin VA showed potent antitrypanosomal activity with an IC(50) value of 0.0026 μg ml(-1) in vitro without cytotoxicity against MRC-5 cells. Dehydrosinefungin V showed moderate antitrypanosomal activity (IC(50)=0.15 μg ml(-1)).

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemistry
  • Adenosine / isolation & purification
  • Adenosine / pharmacology
  • Cell Line
  • Chromatography, Ion Exchange / methods
  • Fermentation
  • Fibroblasts / drug effects
  • Fibroblasts / metabolism
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy / methods
  • Spectrum Analysis / methods
  • Streptomyces / metabolism*
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / isolation & purification
  • Trypanocidal Agents / pharmacology*

Substances

  • Trypanocidal Agents
  • dehydrosinefungin V
  • sinefungin VA
  • Adenosine