Bioactive phenazines from an earwig-associated Streptomyces sp

Chin J Nat Med. 2019 Jun;17(6):475-480. doi: 10.1016/S1875-5364(19)30055-X.

Abstract

Three new phenazine-type compounds, named phenazines SA-SC (1-3), together with four new natural products (4-7), were isolated from the fermentation broth of an earwig-associated Streptomyces sp. NA04227. The structures of these compounds were determined by extensive analyses of NMR, high resolution mass spectroscopic data, as well as single-crystal X-ray diffraction measurement. Sequencing and analysis of the genome data allowed us to identify the gene cluster (spz) and propose a biosynthetic pathway for these phenazine-type compounds. Additionally, compounds 1-5 exhibited moderate inhibitory activity against acetylcholinesterase (AChE), and compound 3 showed antimicrobial activities against Micrococcus luteus.

Keywords: Acetylcholinesterase inhibitory activity; Antimicrobial activity; Biosynthetic pathway; Earwig-associated actinomycete; Phenazine.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology
  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism
  • Crystallography, X-Ray
  • Insecta / microbiology*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects
  • Molecular Structure
  • Multigene Family
  • Phenazines / chemistry*
  • Phenazines / metabolism
  • Phenazines / pharmacology
  • Streptomyces / chemistry*
  • Streptomyces / genetics
  • Streptomyces / metabolism

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Phenazines
  • phenazine