Bicyclic alpha,omega-dicarboxylic acid derivatives from a colonial tunicate of the family Polyclinidae

Bioorg Med Chem Lett. 2009 Nov 1;19(21):6205-8. doi: 10.1016/j.bmcl.2009.08.094. Epub 2009 Sep 3.

Abstract

In the course of our search for bioactive metabolites from a colonial tunicate of the family Polyclinidae, six new (1-6) cyclic fatty acid derivatives were isolated. Their planar structures were established on the basis of NMR and MS spectroscopic analyses. The relative configuration was determined by NOESY experiment. Compounds 1-6 represent a fused bicyclic skeleton possibly derived from alpha,omega-dicarboxylic acids such as eicosanedioic acid or docosanedioic acid via a Diels-Alder type of cyclization. Compounds 1-4 and 6 showed mild cytotoxicity against a panel of five human solid tumor cell lines.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / toxicity
  • Cell Line, Tumor
  • Dicarboxylic Acids / chemistry*
  • Dicarboxylic Acids / isolation & purification
  • Dicarboxylic Acids / toxicity
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Urochordata / chemistry*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Dicarboxylic Acids