Carbamothioic S-acid derivative and kigamicins, the activated production of silent metabolites in Amycolatopsis alba DSM 44262Δ abm9 elicited by N-acetyl-D-glucosamine

Nat Prod Res. 2020 Dec;34(24):3514-3521. doi: 10.1080/14786419.2019.1574783. Epub 2019 Feb 20.

Abstract

One new carbamothioic S-acid derivative (1) and five known kigamicin derivatives (2-6) were isolated from the fermentation extract of Amycolatopsis alba DSM 44262Δabm9 elicited by N-acetyl-D-glucosamine. HPLC-DAD-UV analyses indicated that the DSM 44262Δabm9 strain did not produce these metabolites originally and the production of 1-6 was induced by adding 25 mM N-acetyl-D-glucosamine in the culture medium. The structures of 1-6 were identified on the basis of NMR spectroscopic data and high-resolution ESIMS. These results highlight that addition of N-acetyl-D-glucosamine in the microbial culture medium could activate cryptic gene expression, induce and increase the production of new or known secondary metabolites.

Keywords: Amycolatopsis alba DSM 44262Δabm9; N-acetyl-D-glucosamine; carbamothioic S-acid; elicitation; kigamicins.

MeSH terms

  • Acetylglucosamine / metabolism
  • Acetylglucosamine / pharmacology*
  • Amycolatopsis / drug effects
  • Amycolatopsis / metabolism
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Cell Line, Tumor
  • Culture Media / chemistry
  • Culture Media / pharmacology
  • Doxorubicin / analogs & derivatives*
  • Doxorubicin / chemistry
  • Doxorubicin / metabolism
  • Drug Screening Assays, Antitumor
  • Fermentation
  • Humans
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Oxazoles / chemistry
  • Oxazoles / metabolism*
  • Secondary Metabolism
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Anti-Bacterial Agents
  • Culture Media
  • Oxazoles
  • kigamicin A
  • Doxorubicin
  • Acetylglucosamine

Supplementary concepts

  • Amycolatopsis alba