Nematocidal thiocyanatins from a southern Australian marine sponge Oceanapia sp

J Nat Prod. 2004 Aug;67(8):1277-82. doi: 10.1021/np049977y.

Abstract

Investigations of a southern Australian marine sponge, Oceanapia sp., have yielded two new beta methyl branched bisthiocyanates, thiocyanatins D1 (3a) and D(2) (3b), along with two new thiocarbamate thiocyanates, thiocyanatins E1 (4a) and E2 (4b). The new thiocyanatins belong to a rare class of bioactive marine metabolite previously only represented by thiocyanatins A-C (1, 2a/b). Structures were assigned on the basis of detailed spectroscopic analysis, with comparisons to the known bisthiocyanate thiocyanatin A (1) and synthetic model compounds (5-7). The thiocyanatins exhibit potent nematocidal activity, and preliminary structure-activity relationship investigations have confirmed key characteristics of the thiocyanatin pharmacophore.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Animals
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / isolation & purification*
  • Antinematodal Agents / pharmacology
  • Australia
  • Molecular Structure
  • Porifera / chemistry*
  • Structure-Activity Relationship
  • Thiocyanates / chemistry
  • Thiocyanates / isolation & purification*
  • Thiocyanates / pharmacology

Substances

  • Alkenes
  • Antinematodal Agents
  • Thiocyanates
  • thiocyanatin A
  • thiocyanatin B
  • thiocyanatin D1
  • thiocyanatin D2