11-oxoaerothionin: a cytotoxic antitumor bromotyrosine-derived alkaloid from the Caribbean marine sponge Aplysina lacunosa

J Nat Prod. 1992 Jul;55(7):1007-12. doi: 10.1021/np50085a031.

Abstract

A new cytotoxic bromotyrosine-derived secondary metabolite, 11-oxoaerothionin [3], was isolated from the Caribbean sea sponge Aplysina lacunosa. The structure of 3 was argued on the basis of detailed spectroscopic analysis and by chemical conversion to the known antibiotic compound 11-hydroxyaerothionin [2]. When screened against a panel of four human cell lines, 11-oxoaerothionin [3] showed pronounced as well as selective antitumor activity toward the human colon (HCT 116) cell line within the limited concentration range of 0.01-0.1 microgram/ml.

Publication types

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

MeSH terms

  • Animals
  • Antineoplastic Agents / isolation & purification*
  • Cell Survival / drug effects
  • Colonic Neoplasms
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Oxazoles / chemistry
  • Oxazoles / isolation & purification*
  • Oxazoles / pharmacology
  • Porifera / chemistry*
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology

Substances

  • Antineoplastic Agents
  • Oxazoles
  • Spiro Compounds
  • 11-oxoaerothionin