A New Analogue of Echinomycin and a New Cyclic Dipeptide from a Marine-Derived Streptomyces sp. LS298

Mar Drugs. 2015 Nov 18;13(11):6947-61. doi: 10.3390/md13116947.

Abstract

Quinomycin G (1), a new analogue of echinomycin, together with a new cyclic dipeptide, cyclo-(l-Pro-4-OH-l-Leu) (2), as well as three known antibiotic compounds tirandamycin A (3), tirandamycin B (4) and staurosporine (5), were isolated from Streptomyces sp. LS298 obtained from a marine sponge Gelliodes carnosa. The planar and absolute configurations of compounds 1 and 2 were established by MS, NMR spectral data analysis and Marfey's method. Furthermore, the differences in NMR data of keto-enol tautomers in tirandamycins were discussed for the first time. Antibacterial and anti-tumor activities of compound 1 were measured against 15 drug-sensitive/resistant strains and 12 tumor cell lines. Compound 1 exhibited moderate antibacterial activities against Staphylococcuse pidermidis, S. aureus, Enterococcus faecium, and E. faecalis with the minimum inhibitory concentration (MIC) values ranged from 16 to 64 μg/mL. Moreover, it displayed remarkable anti-tumor activities; the highest activity was observed against the Jurkat cell line (human T-cell leukemia) with an IC50 value of 0.414 μM.

Keywords: anti-tumor activity; antibacterial activity; marine-derived Streptomyces; secondary metabolites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / administration & dosage
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / administration & dosage
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Bacteria / drug effects
  • Cell Line, Tumor
  • Dipeptides / administration & dosage
  • Dipeptides / isolation & purification
  • Dipeptides / pharmacology*
  • Drug Resistance, Bacterial
  • Echinomycin / administration & dosage
  • Echinomycin / analogs & derivatives*
  • Echinomycin / isolation & purification
  • Echinomycin / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Jurkat Cells
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Microbial Sensitivity Tests
  • Porifera / microbiology
  • Streptomyces / isolation & purification
  • Streptomyces / metabolism*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Dipeptides
  • quinomycin
  • Echinomycin