The structure of microcarpalide, a microfilament disrupting agent from an endophytic fungus

Org Lett. 2001 Nov 1;3(22):3479-81. doi: 10.1021/ol016515s.

Abstract

[structure: see text]. A new alkyl-substituted nonenolide, microcarpalide 1, has been isolated from fermentation broths of an unidentified endophytic fungus. Microcarpalide is weakly cytotoxic to mammalian cells and acts as a microfilament disrupting agent. The structure of 1 was elucidated by application of spectroscopic methods. The absolute configuration was determined by the exciton chirality method.

Publication types

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

MeSH terms

  • Actin Cytoskeleton / drug effects*
  • Alkenes / chemical synthesis*
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology
  • Cell Line
  • Circular Dichroism
  • Fungi / chemistry*
  • Humans
  • Lactones / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Microscopy, Fluorescence
  • Molecular Conformation
  • Muscle, Smooth / cytology
  • Muscle, Smooth / drug effects
  • Rats
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism
  • Tumor Cells, Cultured

Substances

  • Alkenes
  • Antineoplastic Agents
  • Lactones
  • oximidine I
  • oximidine II