Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re-collection of Aglaia foveolata

J Nat Prod. 2010 Nov 29;73(11):1873-8. doi: 10.1021/np100503q. Epub 2010 Oct 12.

Abstract

Two new minor silvestrol analogues [2'''-episilvestrol (1) and 2''',5'''-diepisilvestrol (2)], together with a new 21-norbaccharane-type triterpene (3), two new 3,4-secodammarane triterpenes (4 and 5), and a new eudesmane sesquiterpene (6), as well as nine known compounds, were isolated from a large-scale re-collection of the CHCl(3)-soluble extract of the stem bark of Aglaia foveolata obtained in Kalimantan, Indonesia. The structures of the new compounds were established by interpretation of their spectroscopic data. All of the isolates were tested for cytotoxicity against HT-29 cells. The new silvestrol analogues, 1 and 2, were considerably less active as cytotoxic agents than silvestrol (7) and episilvestrol (5'''-episilvestrol) (8) against this cell line, showing the importance of the configuration at C-2''' in mediating such activity within this compound class. Several of the compounds isolated were also evaluated in a NF-κB (p65) inhibition assay.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aglaia / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Indonesia
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Resins, Plant / chemistry
  • Resins, Plant / isolation & purification
  • Sesquiterpenes, Eudesmane / chemistry
  • Sesquiterpenes, Eudesmane / isolation & purification*
  • Sesquiterpenes, Eudesmane / pharmacology
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • 2''',5'''-diepisilvestrol
  • 2'''-episilvestrol
  • Antineoplastic Agents, Phytogenic
  • NF-kappa B
  • Resins, Plant
  • Sesquiterpenes, Eudesmane
  • Triterpenes
  • episilvestrol
  • silvestrol