Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba

J Nat Prod. 1996 Nov;59(11):1029-34. doi: 10.1021/np9605145.

Abstract

Three new adjacent bis-tetrahydrofuran ring Annonaceous acetogenins with four hydroxy groups, bullatetrocin (1), 10-hydroxyasimicin (2), and 10-hydroxytrilobacin (3), were isolated by activity-directed fractionation from the stem bark of Asimina triloba. Their structures were established on the basis of chemical and spectral evidence. The absolute stereochemistry at the C-10 hydroxy position was determined by converting 2 and 3 to their ketolactone isomers, 2,4-cis/trans 10-hydroxyasimicinones and 2,4-cis/trans 10-hydroxytrilobacinones, respectively. The bioactivities of the new compounds against brine shrimp larvae and six human solid-tumor cell lines are reported, and structure-activity relationships between trihydroxylated and tetrahydroxylated acetogenins are discussed. In addition to 1-3, gigantetrocin A, 2,4-cis/trans-gigantetrocin A-ones, annonacin, and annonacin A were also isolated for the first time from this species.

Publication types

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

MeSH terms

  • Animals
  • Artemia
  • Drug Screening Assays, Antitumor
  • Furans / isolation & purification*
  • Furans / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Plant Epidermis / chemistry*
  • Plants, Medicinal / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • 10-hydroxyasimicin
  • Furans
  • bullatetrocin