Gerronemins A-F, cytotoxic biscatechols from a Gerronema species

Phytochemistry. 2002 Mar;59(6):643-8. doi: 10.1016/s0031-9422(02)00013-4.

Abstract

The gerronemins A-F (1-6) were isolated as the cytotoxic components of an extract of a Gerronema species detected in a screening for new cytotoxic metabolites from basidiomycetes. Their structures were elucidated by spectroscopic techniques, and they are composed of a C12-C16 alkane or alkene substituted at both ends by 2,3-dihydroxyphenyl groups. The gerronemins blocked the inducible expression of a hCOX-2 and iNOS promoter driven reporter gene with IC50-values of 1-5 microg/ml. In addition, cytotoxic activities were observed which were due the inhibition of cellular macromolecular syntheses.

MeSH terms

  • Agaricales / chemistry*
  • Alkanes / chemistry
  • Alkanes / isolation & purification
  • Alkanes / pharmacology
  • Alkenes / chemistry
  • Alkenes / isolation & purification
  • Alkenes / pharmacology
  • Animals
  • Catechols / chemistry
  • Catechols / isolation & purification
  • Catechols / pharmacology*
  • Cell Survival / drug effects
  • Cells, Cultured
  • Cyclooxygenase 2
  • Gene Expression / drug effects*
  • Genes, Reporter
  • HL-60 Cells
  • Humans
  • Isoenzymes / genetics
  • Jurkat Cells
  • Membrane Proteins
  • Molecular Conformation
  • Nitric Oxide Synthase / genetics
  • Nitric Oxide Synthase Type II
  • Promoter Regions, Genetic
  • Prostaglandin-Endoperoxide Synthases / genetics
  • Tumor Cells, Cultured

Substances

  • Alkanes
  • Alkenes
  • Catechols
  • Isoenzymes
  • Membrane Proteins
  • NOS2 protein, human
  • Nitric Oxide Synthase
  • Nitric Oxide Synthase Type II
  • Cyclooxygenase 2
  • PTGS2 protein, human
  • Prostaglandin-Endoperoxide Synthases