Antifouling properties of simple indole and purine alkaloids from the Mediterranean gorgonian Paramuricea clavata

J Nat Prod. 2011 Oct 28;74(10):2304-8. doi: 10.1021/np200537v. Epub 2011 Sep 22.

Abstract

Chemical investigation of the Mediterranean gorgonian Paramuricea clavata resulted in the isolation of two new alkaloids, 2-bromo-N-methyltryptamine (1) and 3-bromo-N-methyltyramine (2), together with nine known compounds (3-10 and linderazulene). The bromoindole derivative 3 is reported herein for the first time from a natural source. The chemical structures of these compounds were assigned by spectroscopic analyses and comparison with literature values. The antifouling activity and toxicity of compounds 1-10 were assessed using three marine biofilm bacteria and the Microtox assay. In contrast to commercial antifoulants, bufotenine (5) and 1,3,7-trimethylisoguanine (10) showed significant antiadhesion activity against one bacterial strain while being nontoxic.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Biofouling / prevention & control*
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology*
  • Molecular Structure
  • Purines / chemistry
  • Purines / isolation & purification*
  • Purines / pharmacology
  • Tryptamines / chemistry
  • Tryptamines / isolation & purification*
  • Tryptamines / pharmacology*
  • Tyramine / analogs & derivatives*
  • Tyramine / chemistry
  • Tyramine / isolation & purification
  • Tyramine / pharmacology

Substances

  • 2-bromo-N-methyltryptamine
  • 3-bromo-N-methyltyramine
  • Indole Alkaloids
  • Purines
  • Tryptamines
  • Tyramine