Pyloricidins, novel anti-Helicobacter pylori antibiotics produced by bacillus sp. II. Isolation and structure elucidation

J Antibiot (Tokyo). 2001 Nov;54(11):934-47. doi: 10.7164/antibiotics.54.934.

Abstract

Novel anti-Helicobacter pylori antibiotics, pyloricidins A, A1, A2, B, C and D were isolated from Bacillus sp. HC-70 and Bacillus sp. HC-72 by column chromatographies using adsorption and ion exchange resins. Their structures have been elucidated based on spectroscopic and degradation studies and shown to be peptide-like compounds. These compounds contained two unusual amino acids, viz., 5-amino-2,3,4,6-tetrahydroxyhexanoic acid and 3-amino-3-phenylpropionic acid (beta-phenylalanine). The structure-activity relationship studies suggested that 3-(5-amino-2,3,4,6-tetrahydroxyhexanoyl)amino-3-phenylpropionic acid moiety was essential for anti-H. pylori activity.

MeSH terms

  • Amino Acids / analysis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Bacillus / chemistry*
  • Crystallography, X-Ray
  • Fermentation
  • Gas Chromatography-Mass Spectrometry
  • Helicobacter Infections / drug therapy
  • Helicobacter pylori / drug effects
  • Magnetic Resonance Spectroscopy
  • Optical Rotation
  • Peptides*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship

Substances

  • Amino Acids
  • Anti-Bacterial Agents
  • Peptides