(Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties

J Nat Prod. 1996 Sep;59(9):896-9. doi: 10.1021/np960450y.

Abstract

Reaction of the fungal sesquiterpene illudin S with excess paraformaldehyde in dilute H2SO4 gives (hydroxymethyl)acylfulvene. The primary allylic hydroxyl thus formed can undergo very facile replacement by a variety of nucleophiles. (Hydroxymethyl)acylfulvene (MGI.114) was more toxic than a precursor, acylfulvene, but less toxic than the parent compound illudin S to HL 60 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antibiotics, Antineoplastic / pharmacology
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Basidiomycota / chemistry*
  • Chromatography, Thin Layer
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Lung Neoplasms / drug therapy
  • Magnetic Resonance Spectroscopy
  • Mice
  • Mice, Inbred BALB C
  • Neoplasm Transplantation
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • irofulven
  • illudin S