Asimilobin and cis- and trans-murisolinones, novel bioactive Annonaceous acetogenins from the seeds of Asimina triloba

J Nat Prod. 1995 Oct;58(10):1533-42. doi: 10.1021/np50124a009.

Abstract

Three new bioactive Annonaceous acetogenins, asimilobin [1], cis-murisolinone [2], and trans-murisolinone [3], have been isolated from an ethanolic extract of the seeds of Asimina triloba by directing the fractionation with brine shrimp lethality. The structure were elucidated based on spectroscopic and chemical methods, In addition, cis- and trans-bullatacinone, which are known compounds, were obtained. Asimilobin [1] has adjacent bis-THF rings, located at C-10 to C-17 and having only one flanking hydroxyl group at C-18. Compounds 1-3 showed cytotoxicity values comparable with adriamycin against six human solid tumor cell lines.

Publication types

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

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Decapoda / drug effects
  • Furans / chemistry
  • Furans / isolation & purification*
  • Furans / toxicity
  • Humans
  • Insecticides / chemistry
  • Insecticides / isolation & purification*
  • Insecticides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Seeds / chemistry*
  • Stereoisomerism
  • Trees / embryology*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Furans
  • Insecticides