Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring

J Nat Prod. 2005 Feb;68(2):194-7. doi: 10.1021/np040184l.

Abstract

Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.

MeSH terms

  • Animals
  • Artemia / drug effects
  • Asimina / chemistry*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Electron Transport Complex I / antagonists & inhibitors
  • Furans / chemistry
  • Furans / isolation & purification*
  • Furans / pharmacology
  • Humans
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Maryland
  • Molecular Structure
  • Seeds / chemistry

Substances

  • 4-hydroxytrilobin
  • Furans
  • Lactones
  • asimitrin
  • Electron Transport Complex I