Pleofungins, novel inositol phosphorylceramide synthase inhibitors, from Phoma sp. SANK 13899. II. Structural elucidation

J Antibiot (Tokyo). 2007 Feb;60(2):143-52. doi: 10.1038/ja.2007.14.

Abstract

Pleofungins (formerly called F-15078) A, B, C and D, novel depsipeptide antifungal antibiotics, were found in a mycelium extract of the producing fungus, Phoma sp. SANK 13899. The structures of pleofungins A, B, C and D were elucidated mainly by various NMR studies. The absolute configurations of the amino acids and N-methyl amino acids of pleofungin A constituents in the hydrolysate were determined by the application of advanced Marfey's method in combination with gas chromatography/mass spectrometry analysis of their silylation products with N-methyl-N-(tert-butylsilyl)trifluoroacetamide. Two alpha-hydroxy acid constituents, alpha-hydroxyisocaproic acid and alpha-hydroxyisovaleric acid, were isolated from the hydrolysate and their stereochemistries were determined by their specific rotations.

MeSH terms

  • Acetic Anhydrides / chemistry
  • Alkalies
  • Ascomycota / chemistry*
  • Chemical Phenomena
  • Chemistry, Physical
  • Depsipeptides / chemistry*
  • Enzyme Inhibitors / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Hexosyltransferases / antagonists & inhibitors*
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Methanol / chemistry
  • Methylation
  • Molecular Conformation
  • Spectrometry, Mass, Electrospray Ionization
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Acetic Anhydrides
  • Alkalies
  • Depsipeptides
  • Enzyme Inhibitors
  • acetic anhydride
  • Hexosyltransferases
  • phosphatidylinositol-ceramide phosphoinositol transferase
  • Methanol