RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening

J Antibiot (Tokyo). 2014 Apr;67(4):323-9. doi: 10.1038/ja.2013.144. Epub 2014 Feb 5.

Abstract

Two novel quinomycin derivatives, RK-1355A (1) and B (2), and one known quinomycin derivative, UK-63,598 (3), were isolated from a microbial metabolites fraction library of Streptomyces sp. RK88-1355 based on Natural Products Plot screening. The structural elucidation of 1 and 2 was established through two-dimensional NMR and mass spectrometric measurements. They belong to a class of quinomycin antibiotics family having 3-hydroxyquinaldic acid and a sulfoxide moiety. They are the first examples for natural products as a quinoline type quinomycin having a sulfoxide on the intramolecular cross-linkage. They showed potent antiproliferative activities against various cancer cell lines and they were also found to exhibit moderate antibacterial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Discovery*
  • Echinomycin / analogs & derivatives*
  • Echinomycin / chemistry
  • Echinomycin / isolation & purification
  • Echinomycin / metabolism
  • Echinomycin / pharmacology
  • Escherichia coli / drug effects*
  • Escherichia coli / growth & development
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Small Molecule Libraries
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / growth & development
  • Streptomyces / metabolism*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • RK-1355A
  • Small Molecule Libraries
  • UK 63598
  • Echinomycin