Novel extracellular diterpenoids with biological activity from the cyanobacterium Nostoc commune

J Nat Prod. 2000 Mar;63(3):339-43. doi: 10.1021/np9903090.

Abstract

Five novel extracellular metabolites with an unprecedented diterpenoid skeleton, 5-[(5-carboxy-2-hydroxy)benzyl]-11-hydroxymethyl-2,5,6,8a, 11-pentamethyldodecahydrocyclopenta<a>naphthalene (1), 5-[(5-carboxy-2-hydroxy)benzyl]-11-formyl-2,5,6,8a, 11-pentamethyl-dodecahydrocyclopenta<a>naphthalene (2), 5-[(5-carboxy-2-hydroxy)benzyl]-11-carboxy-2,5,6,8a, 11-pentamethyl-dodecahydrocyclopenta<a>naphthalene (3), 5-[(5-carboxy-2-hydroxy)benzyl]-11-dihydroxymethyl-2,5,6,8a, 11-pentamethyldodecahydrocyclopenta<a>naphthalene (4), and 5-[(5-carboxy-2-hydroxy)benzyl]-11-acetyl-2,5,6, 8a-tetramethyldodecahydrocyclopenta<a>naphthalene (5), have been isolated from the culture medium of the terrestrial cyanobacterium Nostoc commune by means of bioguided isolation. The molecules were designated as comnostins A-E. The structures were determined by spectroscopic methods, mainly NMR and mass spectrometry. The relative stereochemistry of comnostin A was confirmed by single-crystal X-ray structure analysis. All comnostins showed antibacterial activities. Additionally, cytotoxic and molluscicidal activities were found for comnostin B.

MeSH terms

  • Cyanobacteria / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Spectrum Analysis
  • Tumor Cells, Cultured

Substances

  • Diterpenes