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

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.

• Authors: Yu-Hsuan Lan, Fang-Rong Chang, Chih-Chuang Liaw, Chin-Chung Wu, Michael-Y Chiang, Yang-Chang Wu
• Journal: Planta medica (Planta Med) Vol. 71 Issue 2 Pg. 153-9 (Feb 2005) ISSN: 0032-0943 [Print] Germany
• PMID: 15729624 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents, Phytogenic
• Lactones
• Plant Extracts

Topics

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