Sequoiamonascins a-d: novel anticancer metabolites isolated from a redwood endophyte

J Org Chem. 2003 Jun 13;68(12):4966-9. doi: 10.1021/jo0340253.

Abstract

Aspergillus parasiticus, a fungal isolate from the bark of a redwood tree (Sequoia sempervirens), has been shown to produce the antitumor metabolites sequoiatones A and B and more recently the sequoiatones C-F. We have also isolated another series of compounds with a new carbon skeleton, the sequoiamonascins. The structures of sequoiamonascins A-D were deduced by interpretation of their spectral data and that of some reaction products. The sequoiamonascins were isolated by brine shrimp lethality-guided fractionation and were submitted to the NCI for anticancer evaluation.

Publication types

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

MeSH terms

  • Animals
  • Artemia / drug effects
  • Aspergillus / chemistry*
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification*
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sequoia / chemistry
  • Tumor Cells, Cultured / drug effects

Substances

  • Heterocyclic Compounds, 4 or More Rings
  • Lactones