Caulibugulones A-F, novel cytotoxic isoquinoline quinones and iminoquinones from the marine bryozoan Caulibugula intermis

J Nat Prod. 2004 Jan;67(1):70-3. doi: 10.1021/np030378l.

Abstract

An extract of the marine bryozoan Caulibugula intermis, collected in the Indo-Pacific off Palau, produced a distinct pattern of differential cytotoxicity in the National Cancer Institute's 60 cell line antitumor screen. Bioactivity-directed fractionation of the extract provided six new compounds, caulibugulones A-F (1-6). The structures of these novel metabolites were determined by spectrochemical analyses including LC-MS, HRFABMS, 1-D and 2-D NMR experiments, and by comparison with related compounds. The structures of compounds 2 and 3 were confirmed by chemical interconversion. The isolated compounds exhibited IC(50)'s of 0.03-1.67 microg/mL against murine tumor cells in an in vitro cytotoxicity assay.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Bryozoa / chemistry*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Isoquinolines / chemistry
  • Isoquinolines / isolation & purification*
  • Isoquinolines / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Palau
  • Quinones / chemistry
  • Quinones / isolation & purification*
  • Quinones / pharmacology

Substances

  • Antineoplastic Agents
  • Isoquinolines
  • Quinones