Plipastatins: New Inhibitors of Phospholipase A2, Produced by Bacillus Cereus BMG302-fF67. II. Structure of Fatty Acid Residue and Amino Acid Sequence

J Antibiot (Tokyo). 1986 Jun;39(6):745-54. doi: 10.7164/antibiotics.39.745.

Abstract

Plipastatins, new inhibitors of phospholipase A2, were produced by a strain classified as Bacillus cereus BMG302-fF67. The plipastatins are a family of acylated decapeptides which differ from each other by amino acid composition and the nature of the fatty acid side chain. The fatty acids have been shown to be 3(R)-hydroxyhexadecanoic acid (n-C16h3) and 14(S)-methyl-3(R)-hydroxyhexadecanoic acid (a-C16h3) by mass, NMR and optical rotation. Amino acid sequence analysis by secondary ion mass spectrometry and additional physico-chemical evidence indicate that the structures of plipastatinic acids, the lactone-opened peptides are as follows: beta-Hydroxy fatty acid----L-Glu----D-Orn----L-Tyr----D-allo-Thr----L-Glu----D-Ala(Val)---- L-Pro----L-Gln----D-Tyr----L-Ile X OH.

MeSH terms

  • Amino Acid Sequence
  • Anti-Bacterial Agents / analysis*
  • Bacillus cereus / metabolism
  • Fatty Acids / analysis*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Oligopeptides / analysis*
  • Peptides, Cyclic
  • Phospholipases / antagonists & inhibitors*
  • Phospholipases A / antagonists & inhibitors*
  • Phospholipases A2

Substances

  • Anti-Bacterial Agents
  • Fatty Acids
  • Oligopeptides
  • Peptides, Cyclic
  • plipastatin
  • Phospholipases
  • Phospholipases A
  • Phospholipases A2