Digoniodiol, deoxygoniopypyrone A, and goniofupyrone A: three new styryllactones from Goniothalamus amuyon.
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.
Lan
Yu-Hsuan
YH
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan.
Chang
Fang-Rong
FR
Liaw
Chih-Chuang
CC
Wu
Chin-Chung
CC
Chiang
Michael-Y
MY
Wu
Yang-Chang
YC
D029061:Annonaceae; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor / Q000187:drug effects; D018360:Crystallography, X-Ray; D006801:Humans; D020128:Inhibitory Concentration 50; D007536:Isomerism; D007783:Lactones / Q000737:chemistry / Q000494:pharmacology*; D008517:Phytotherapy; D035261:Plant Components, Aerial; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*
D000972:Antineoplastic Agents, Phytogenic; D007783:Lactones; D010936:Plant Extracts