New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata

Planta Med. 2003 Mar;69(3):241-6. doi: 10.1055/s-2003-38485.

Abstract

Bioactivity-guided fractionation led to the isolation of two new Annonaceous acetogenins, annocatacin A ( 1). and annocatacin B ( 2). from the seeds and the leaves, respectively, of Annona muricata. Compounds 1 and 2 are the first examples where the adjacent bis-tetrahydrofuran ring system is located at C-15. The new structures were elucidated and characterized by spectral and chemical methods. Both Annonaceous acetogenins 1 and 2 showed significant in vitro cytotoxicity toward the human hepatoma cell lines, Hep G2 and 2,2,15, and were compared with the known adjacent bis-tetrahydrofuran acetogenins, neoannonin ( 3). desacetyluvaricin ( 4). bullatacin ( 5). asimicin ( 6). annoglaucin ( 7). squamocin ( 8). and rollimusin ( 9).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Annona*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Carcinoma, Hepatocellular / drug therapy
  • Carcinoma, Hepatocellular / pathology
  • Furans / pharmacology*
  • Humans
  • Liver Neoplasms / drug therapy
  • Liver Neoplasms / pathology
  • Magnetic Resonance Spectroscopy
  • Phytotherapy*
  • Plant Leaves
  • Plant Preparations / chemistry
  • Plant Preparations / pharmacology*
  • Seeds
  • Structure-Activity Relationship
  • Tumor Cells, Cultured / drug effects

Substances

  • Antineoplastic Agents, Phytogenic
  • Furans
  • Plant Preparations
  • annocatacin A
  • annocatacin B