Antineoplastic diterpene-benzoate macrolides from the Fijian red alga Callophycus serratus

Org Lett. 2005 Nov 10;7(23):5261-4. doi: 10.1021/ol052121f.

Abstract

[structures: see text] Three diterpene-benzoate natural products, with novel carbon skeletons and an unusual proposed biosynthesis, were isolated from extracts of the Fijian red alga Callophycus serratus and identified by a combination of X-ray crystallographic, NMR, and mass spectral analyses. Bromophycolide A (1) displayed cytotoxicity against several human tumor cell lines via specific apoptotic cell death. This represents the first discovery of natural products incorporating a diterpene and benzoate skeleton into a macrolide system.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Benzoates / chemistry
  • Benzoates / isolation & purification*
  • Benzoates / pharmacology
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drug Resistance, Bacterial
  • Drug Screening Assays, Antitumor
  • Fiji
  • Humans
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Rhodophyta / chemistry*
  • Tumor Cells, Cultured

Substances

  • Anti-Bacterial Agents
  • Anti-HIV Agents
  • Antineoplastic Agents
  • Benzoates
  • Diterpenes
  • Macrolides
  • bromophycolide A