Petrosamine B, an inhibitor of the Helicobacter pylori enzyme aspartyl semialdehyde dehydrogenase from the Australian sponge Oceanapia sp

J Nat Prod. 2005 May;68(5):804-6. doi: 10.1021/np049595s.

Abstract

Bioassay-guided fractionation of the MeOH extract of the sponge Oceanapia sp. using the Helicobacter pylori enzyme, aspartyl semialdehyde dehydrogenase, ASD, to detect antibacterial activity, led to the isolation of a new pyridoacridine alkaloid, petrosamine B (1). Petrosamine B is a bright blue compound that is sparingly soluble in many organic solvents. The structure of 1 was determined from detailed NMR studies performed in TFA/D2O. Petrosamine B was found to be a weak inhibitor of ASD with an IC50 of 306 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemistry
  • Acridines / isolation & purification*
  • Acridines / pharmacology
  • Aldehyde Dehydrogenase / antagonists & inhibitors*
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Australia
  • Bacterial Proteins / antagonists & inhibitors*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Helicobacter pylori / enzymology*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification*
  • Phenanthrenes / pharmacology
  • Porifera / chemistry*

Substances

  • Acridines
  • Alkaloids
  • Bacterial Proteins
  • Enzyme Inhibitors
  • Phenanthrenes
  • petrosamine B
  • Aldehyde Dehydrogenase
  • aspartyl semialdehyde dehydrogenase, Helicobacter pylori