Isolation and identification of ingredients inducing cancer cell death from the seeds of Alpinia galanga, a Chinese spice

• Published in: Food & function 2015-02, Vol.6 (2), p.431-443
• Main Authors: Zeng, Qiao-hui, Lu, Chuan-Li, Zhang, Xue-wu, Jiang, Jian-Guo
• Format: Article
• Language: English
• Subjects: Acetates - chemistry; Alpinia; Alpinia - chemistry; Alpinia galanga; Animals; Antineoplastic Agents, Phytogenic - pharmacology; Cell Death - drug effects; Cell Line, Tumor; Dextrans; Food Analysis; HeLa Cells; Hep G2 Cells; Humans; Hydrogen Peroxide; PC12 Cells; Plant Extracts - pharmacology; Rats; Seeds - chemistry; Spices
• ISSN: 2042-6496; 2042-650X
• DOI: 10.1039/c4fo00709c

This study was carried out to isolate ingredients from the seeds of a Chinese spice ( Alpinia galangal ) and to evaluate their cytotoxic activity on cancer cell lines. Isolation and purification of the phytochemical constituents were conducted using silica gel, Sephadex LH-20 and ODS columns. After extraction using 95% ethanol, the total extracts were re-extracted, resulting in petroleum ether (PE), ethyl acetate (EA) and water fractions, respectively. Activity tests showed that the EA fraction exhibited obvious ( p < 0.05) protective effects on H 2 O 2 damaged PC-12 cells at 20 μg mL −1 , and showed much higher ( p < 0.05) cytotoxic activity on cancer cell lines than other fractions. Five compounds, 1′- S -1′-acetoxyeugenol acetate ( I ), 1′- S -1′-acetoxychavicol acetate ( II ), 2-propenal, 3-[4-(acetyloxy)-3-methoxyphenyl] ( III ), isocoronarin D ( IV ) and caryolane-1, 9β-diol ( V ), were obtained from the EA fraction and identified by HPLC, UV, MS, and NMR spectroscopic analyses. Compounds III and V were isolated from A. galangal for the first time. Moreover, compounds I , II , IV and V were the main active ingredients for inducing death of the tested cancer cells, and their IC 50 values ranged from 60 to 90 μg mL −1 , indicating that these compounds possessed a wide anti-cancer capability. Therefore, A. galangal seeds could be a potential source of healthy food for tumor prevention. This study was carried out to isolate ingredients from the seeds of a Chinese spice ( Alpinia galangal ) and to evaluate their cytotoxic activity on cancer cell lines.