Equilibrating isomers: bromoindoles and a seco-xanthine encountered during a study of nematocides from the southern Australian marine sponge Hymeniacidon sp

J Nat Prod. 2002 Mar;65(3):368-70. doi: 10.1021/np010337u.

Abstract

Bioassay-directed fractionation of a Hymeniacidon sp. yielded as nematocidal agents the equilibrating E/Z bromoindole ethyl esters 1 and 2 and corresponding methyl esters 3 and 4. Also isolated for the first time as a natural product was an equilibrating mixture of seco-xanthine formamides, attributed the trivial name hymeniacidin (5). The structure for 5 was assigned on the basis of detailed spectroscopic analysis and total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / isolation & purification*
  • Antinematodal Agents / pharmacology
  • Australia
  • Bromides / chemistry
  • Chromatography, High Pressure Liquid
  • Indoles / chemistry
  • Indoles / isolation & purification*
  • Indoles / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera
  • Stereoisomerism
  • Xanthenes / chemistry
  • Xanthenes / isolation & purification*
  • Xanthenes / pharmacology

Substances

  • Antinematodal Agents
  • Bromides
  • Indoles
  • Xanthenes
  • hymeniacidin