Digoniodiol, deoxygoniopypyrone A, and goniofupyrone A: three new styryllactones from Goniothalamus amuyon

Planta Med. 2005 Feb;71(2):153-9. doi: 10.1055/s-2005-837783.

Abstract

Three new styrylpyrone analogues, digoniodiol (2), deoxygoniopypyrone A (3), and goniofupyrone A (4), along with ten known styryllactones, were isolated from the aerial parts of Goniothalamus amuyon. Among these compounds, 2 is the first example of a bis-styrylpyrone. Compound 4 represents a new skeleton for styryllactones. All structures were established on the basis of spectroscopic data. The stereochemistry of 2 and 4 was determined by X-ray crystallographic analysis. The absolute configuration of 3 and 4 was further confirmed by Mosher ester derivatives. All styryllactones were subjected to cytotoxicity assays. Among them, goniothalamin, goniothalamin epoxide, and 8-chlorogoniodiol showed significant cytotoxicity against the HepG2 cancer cell line with IC50 in the range of 0.19 - 0.64 microg/mL, and moderate activity toward Hep3B, MDA-MB-231, and MCF-7 cancer cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Annonaceae*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor / drug effects
  • Crystallography, X-Ray
  • Humans
  • Inhibitory Concentration 50
  • Isomerism
  • Lactones / chemistry
  • Lactones / pharmacology*
  • Phytotherapy*
  • Plant Components, Aerial
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Lactones
  • Plant Extracts