Three new cyclic peroxides from the marine sponge Plakortis aff simplex

J Nat Prod. 2003 May;66(5):682-5. doi: 10.1021/np020589a.

Abstract

In our continuing program to identify bioactive compounds from marine invertebrates, the MeOH-EtOAc (1:1) extract of the sponge Plakortis aff simplex, collected in Madagascar, was found to be cytotoxic to a series of human tumor cells. From this sponge, three new compounds and one known one, two new 1,2-dioxane peroxylactones named plakortolides H (1) and I (2), and one new 1,2-dioxolane, designated andavadoic acid (3), have been isolated and their structures elucidated. In addition, the known N(3)-methyladenine (4) was isolated, to the best of our knowledge, for the first time from a marine source. Andavadoic acid (3) showed significant activity against 13 tumor cells with GI(50) values in the submicromolar range.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Heterocyclic Compounds, 1-Ring / chemistry
  • Heterocyclic Compounds, 1-Ring / isolation & purification*
  • Heterocyclic Compounds, 1-Ring / pharmacology
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Heterocyclic Compounds, 2-Ring / isolation & purification*
  • Heterocyclic Compounds, 2-Ring / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Madagascar
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peroxides / chemistry
  • Peroxides / isolation & purification*
  • Peroxides / pharmacology
  • Porifera / chemistry*
  • Tumor Cells, Cultured / drug effects

Substances

  • Antineoplastic Agents
  • Heterocyclic Compounds, 1-Ring
  • Heterocyclic Compounds, 2-Ring
  • Peroxides
  • andavadoic acid
  • plakortolide H
  • plakortolide I