Spiculoic acids A and B, new polyketides isolated from the Caribbean marine sponge Plakortis angulospiculatus

Org Lett. 2004 Jan 8;6(1):75-8. doi: 10.1021/ol0361047.

Abstract

[structure: see text] Two novel polyketides, spiculoic acids A (1) and B (2), have been isolated from extracts of the Caribbean marine sponge Plakortisangulospiculatus. The structures of 1 and 2 were elucidated by detailed analysis of spectroscopic data. Spiculoic acid A (1) showed in vitro cytotoxicity against human breast cancer MCF-7 cells. It has a putative polyketide biogenetic origin that involves incorporation of four butyrate units and a Diels Alderase catalyzed intramolecular [4 + 2] cycloaddition reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Apoptosis
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / isolation & purification*
  • Carboxylic Acids / pharmacology
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Indans / chemistry
  • Indans / isolation & purification*
  • Indans / pharmacology
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Porifera / chemistry*
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Carboxylic Acids
  • Indans
  • Macrolides
  • spiculoic acid A
  • spiculoic acid B