Psammaplin A, a chitinase inhibitor isolated from the Fijian marine sponge Aplysinella rhax

Bioorg Med Chem. 2002 Apr;10(4):1123-8. doi: 10.1016/s0968-0896(01)00372-8.

Abstract

Several brominated tyrosine derived compounds, psammaplins A (1), K (2) and L (3) as well as bisaprasin (4) were isolated from the Fijian marine sponge Aplysinella rhax during a bioassay guided isolation protocol. Their structures were determined using NMR and MS techniques. Psammaplin A was found to moderately inhibit chitinase B from Serratia marcescens, the mode of inhibition being non-competitive. Crystallographic studies suggest that a disordered psammaplin A molecule is bound near the active site. Interestingly, psammaplin A was found to be a potent antifungal agent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Catalytic Domain
  • Chitinases / antagonists & inhibitors*
  • Disulfides / chemistry
  • Disulfides / isolation & purification*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Insecta / drug effects
  • Insecticides / chemistry
  • Insecticides / isolation & purification
  • Kinetics
  • Molecular Structure
  • Plant Proteins / antagonists & inhibitors
  • Porifera / chemistry*
  • Spores, Fungal / drug effects
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemistry
  • Tyrosine / isolation & purification*

Substances

  • Antifungal Agents
  • Disulfides
  • Enzyme Inhibitors
  • Insecticides
  • Plant Proteins
  • psammaplin A
  • Tyrosine
  • Chitinases
  • PLC-B protein, Phytolacca americana

Associated data

  • PDB/1GPF