Planta Med 2005; 71(2): 153-159
DOI: 10.1055/s-2005-837783
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Digoniodiol, Deoxygoniopypyrone A, and Goniofupyrone A: Three New Styryllactones from Goniothalamus amuyon

Yu-Hsuan Lan1 , Fang-Rong Chang1 , Chih-Chuang Liaw1 , Chin-Chung Wu1 , Michael-Y Chiang2 , Yang-Chang Wu1
  • 1Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 2Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, Taiwan
Further Information

Publication History

Received: April 26, 2004

Accepted: August 29, 2004

Publication Date:
24 February 2005 (online)

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 μg/mL, and moderate activity toward Hep3B, MDA-MB-231, and MCF-7 cancer cell lines.

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Prof. Dr. Yang-Chang Wu

Graduate Institute of Natural Products

Kaohsiung Medical University

Kaohsiung 807

Taiwan

Republic of China

Fax: +886-7-311-4773

Email: yachwu@kmu.edu.tw