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Activating and Attenuating the Amicoumacin Antibiotics.

Hyun Bong Park1,2, Corey E Perez3,4, Elena Kim Perry5,6

  • 1Department of Chemistry, Yale University, New Haven, CT 06520, USA. hyunbong.park@yale.edu.

Molecules (Basel, Switzerland)
|June 28, 2016
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Summary
This summary is machine-generated.

Researchers activated a silent pathway in Xenorhabdus bovienii, discovering new amicoumacins. This bacterium, previously unknown to produce these compounds, yielded novel N-acetylated variants lacking antibacterial activity.

Keywords:
biosynthesisgenome mininginsect pathogenisocoumarinnatural productorphan pathway

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Area of Science:

  • Microbiology
  • Natural Product Chemistry
  • Biochemistry

Background:

  • Amicoumacins are dihydroisocoumarin natural products with diverse bioactivities, produced by Gram-positive bacteria via hybrid biosynthetic pathways.
  • Xenorhabdus bovienii, a Gram-negative entomopathogen, was not previously known to produce amicoumacins.
  • X. bovienii engages in a symbiotic relationship with Steinernema nematodes, impacting insect hosts.

Purpose of the Study:

  • To investigate the potential for amicoumacin production in Xenorhabdus bovienii.
  • To characterize novel amicoumacin variants and their biosynthetic pathway.
  • To compare the X. bovienii amicoumacin pathway with related pathways in other bacteria.

Main Methods:

  • Stimulation of a cryptic amicoumacin pathway using a specialized growth medium mimicking waxmoth hemolymph.
  • Structural elucidation of amicoumacins via 2D-NMR, HR-ESI-QTOF-MS, tandem MS, and polarimetry.
  • Comparative genomic analysis of amicoumacin gene clusters and in vitro biochemical validation of N-acetylation.

Main Results:

  • Successful detection and characterization of amicoumacins in X. bovienii.
  • Identification of a unique acetyltransferase in the X. bovienii pathway, leading to N-acetyl-amicoumacins.
  • Demonstration that N-acetylation abolishes the antibacterial activity of amicoumacins.

Conclusions:

  • A cryptic amicoumacin biosynthetic pathway was activated in the Gram-negative bacterium X. bovienii.
  • The presence of an acetyltransferase results in inactive N-acetylated amicoumacins, suggesting a mechanism for self-regulation or host interaction.
  • This study expands the known producers of amicoumacins and reveals novel structural and functional diversity within this natural product class.