A new cytotoxic calyculinamide derivative, geometricin A, from the Australian sponge Luffariella geometrica

J Nat Prod. 2002 Jul;65(7):1056-8. doi: 10.1021/np010544u.

Abstract

Geometricin A (1), together with the known compounds (7E,12E,18S,20Z)-variabilin (2), clathryimine A (3), tryptophol (4), and L-tryptophan, has been isolated from the methanol extract of the Australian sponge Luffariella geometrica. The structure of the new compound geometricin A (1) was elucidated by employing spectroscopic techniques (NMR, MS, UV, and IR) and by comparison of its NMR data with those of the calyculins and calyculinamides. Geometricin A (1) was found to be moderately cytotoxic toward the tumor cell lines HM02 and HEPG2 with GI50's of 1.7 and 2.8 microg/mL, respectively, and to have antialgal activity (growth inhibition zone 5 mm at the 50 microg level).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Australia
  • Bacillus megaterium / drug effects
  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / isolation & purification
  • Biphenyl Compounds / pharmacology
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • Escherichia coli / drug effects
  • Eukaryota / drug effects
  • Fungi / drug effects
  • Furans / chemistry
  • Furans / isolation & purification
  • Furans / pharmacology
  • HIV Reverse Transcriptase / metabolism
  • Humans
  • Indoles / chemistry
  • Indoles / isolation & purification
  • Indoles / pharmacology
  • Liver Neoplasms
  • Lymphocyte Specific Protein Tyrosine Kinase p56(lck) / metabolism
  • Mass Spectrometry
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxazoles / chemistry
  • Oxazoles / isolation & purification*
  • Oxazoles / pharmacology
  • Porifera / chemistry*
  • Quinolizines / chemistry
  • Quinolizines / isolation & purification
  • Quinolizines / pharmacology
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism
  • Stomach Neoplasms
  • Tumor Cells, Cultured / drug effects

Substances

  • (7E,12E,18S,20Z)-variabilin
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antineoplastic Agents
  • Biphenyl Compounds
  • Furans
  • Indoles
  • Oxazoles
  • Quinolizines
  • clathryimine A
  • geometricin A
  • tryptophol
  • Lymphocyte Specific Protein Tyrosine Kinase p56(lck)
  • HIV Reverse Transcriptase