The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba

Bioorg Med Chem. 1996 Jan;4(1):25-32. doi: 10.1016/0968-0896(95)00155-7.

Abstract

A novel acetogenin, asiminocin (1), was isolated by activity-directed fractionation from the stem bark of the paw paw tree, Asimina triloba. By spectral and chemical methods, 1 was identified as (30S)-hydroxy-4-deoxyasimicin. The absolute configuration of 1, along with those of previously reported acetogenins asimin, asiminacin, bullatin, (30S)-bullanin, and (30R) bullanin, was determined by Mosher ester methodology. Compound 1 was highly inhibitory to three human solid tumor cell lines with over a billion times the potency of adriamycin.

Publication types

  • 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*
  • Artemia / drug effects
  • Circular Dichroism
  • Drug Screening Assays, Antitumor
  • Furans / chemistry*
  • Furans / isolation & purification
  • Furans / pharmacology*
  • Humans
  • Lactones / chemistry*
  • Lactones / pharmacology*
  • Lethal Dose 50
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetrahydrofolates / chemistry*
  • Trees / chemistry*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Furans
  • Lactones
  • Tetrahydrofolates
  • asiminocin
  • bullatacin
  • 5,6,7,8-tetrahydrofolic acid