Characterization of anticholinesterase-active 3-alkylpyridinium polymers from the marine sponge Reniera sarai in aqueous solutions

J Nat Prod. 1997 Oct;60(10):991-6. doi: 10.1021/np970292q.

Abstract

From the marine sponge Reniera sarai 3-alkylpyridinium oligomers and polymers have been isolated. 3-Alkylpyridinium polymers are potent anticholinesterase agents; in addition, they show hemolytic and cytotoxic activities. Oligomers with a molecular weight lower than 3000 Da do not possess any significant activity. We report structural characterization of 3-alkylpyridinium polymers and their behavior in aqueous solutions. We found that biologically active polymers are composed of head-to-tail 3-alkylpyridinium units. According to MALDI-TOF spectrometry two species of polymers exist, the smaller with a molecular weight of 5520 Da and the larger with a molecular weight of 18,900 Da. Both polymers are soluble only in water, while low molecular oligomers are readily soluble in organic solvents. Polymers form large water-dissolved supramolecular structures with an average hydrodynamic radius of 23 +/- 2 nm and, therefore, cannot be separated with size-exclusion chromatography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / pharmacology*
  • Chromatography, Gel
  • Chromatography, High Pressure Liquid
  • Light
  • Molecular Weight
  • Porifera / chemistry*
  • Pyridinium Compounds / isolation & purification
  • Pyridinium Compounds / pharmacology*
  • Scattering, Radiation
  • Solutions
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Spectrophotometry, Ultraviolet
  • Ultrafiltration

Substances

  • Cholinesterase Inhibitors
  • Pyridinium Compounds
  • Solutions