Pseudopyronines A and B, alpha-pyrones produced by a marine Pseudomonas sp. F92S91, and evidence for the conversion of 4-hydroxy-alpha-pyrone to 3-furanone

J Nat Prod. 2005 Jun;68(6):920-3. doi: 10.1021/np050038v.

Abstract

In our search for inhibitors of bacterial fatty acid biosynthesis, two new alpha-pyrones, pseudopyronines A (1) and B (2), were isolated from a marine Pseudomonas sp. F92S91. The naturally occurring alpha-pyrones appeared to be unstable, evidenced by the conversion of pseudopyronine B into an oxidation product, 3-furanone (3). Structural elucidations were made by spectroscopic analyses including 2D-NMR data.

MeSH terms

  • Furans / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pseudomonas / chemistry*
  • Pseudomonas / metabolism
  • Pyrones / chemistry
  • Pyrones / isolation & purification*
  • Pyrones / pharmacology

Substances

  • Furans
  • Pyrones
  • pseudopyronine A
  • pseudopyronine B