Structure, Biosynthesis, and Occurrence of Bacterial Pyrrolizidine Alkaloids

Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12702-5. doi: 10.1002/anie.201504877. Epub 2015 Aug 25.

Abstract

Pyrrolizidine alkaloids (PAs) are widespread plant natural products with potent toxicity and bioactivity. Herein, the identification of bacterial PAs from entomopathogenic bacteria using differential analysis by 2D NMR spectroscopy (DANS) and mass spectrometry is described. Their biosynthesis was elucidated to involve a non-ribosomal peptide synthetase. The occurrence of these biosynthesis gene clusters in Gram-negative and Gram-positive bacteria indicates an important biological function in bacteria.

Keywords: Baeyer-Villiger oxidation; biosynthesis; natural products; non-ribosomal peptide synthetases; pyrrolizidine alkaloids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacteria / chemistry
  • Bacteria / enzymology
  • Bacteria / metabolism*
  • Bacterial Proteins / metabolism
  • Biosynthetic Pathways
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Peptide Synthases / metabolism
  • Pyrrolizidine Alkaloids / chemistry*
  • Pyrrolizidine Alkaloids / metabolism*
  • Xenorhabdus / chemistry
  • Xenorhabdus / enzymology
  • Xenorhabdus / metabolism

Substances

  • Bacterial Proteins
  • Pyrrolizidine Alkaloids
  • Peptide Synthases