A novel diarylheptanoid-bearing sesquiterpene moiety from the rhizomes of Alpinia officinarum

Abstract A new diarylheptanoid analogue-bearing sesquiterpene moiety, named Alpinisin A, was isolated from the rhizomes of Alpinia officinarum Hance. The new structure was determined by various spectroscopic techniques 1H-nuclear magnetic resonance (1H NMR), 13C-attached proton test (13C-APT), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), 1H-1H correlation spectroscopy (1H–1HCOSY), nuclear overhauser effect spectroscopy (NOESY) and high resolution electrospray ionization mass spectrometry (HR–ESI–MS). The compound was tested for cytotoxic activity in vitro against human tumour cell lines (gastric carcinoma cell -7901 (SGC-7901), Michigan Cancer Foundation-7 (MCF-7) and Caski), which showed significant inhibitory effects with IC50 levels of 11.42, 15.14 and 14.78 μM, respectively. The novel chemical structure characterised with a diarylheptanoid linked to a chain-like sesquiterpenoid should be highlighted.

[1]  Qiongyu Zou,et al.  A new labdane diterpene from the rhizomes of Alpinia officinarum , 2016, Natural product research.

[2]  Wenjing Zhang,et al.  Galangin induces B16F10 melanoma cell apoptosis via mitochondrial pathway and sustained activation of p38 MAPK , 2013, Cytotechnology.

[3]  Bing-Mei Chen,et al.  Anti-obesity and hypolipidemic effects of ethanolic extract from Alpinia officinarum Hance (Zingiberaceae) in rats fed high-fat diet. , 2010, Journal of medicinal food.

[4]  Hi-Joon Park,et al.  Anti-inflammatory, anti-nociceptive, and anti-psychiatric effects by the rhizomes of Alpinia officinarum on complete Freund's adjuvant-induced arthritis in rats. , 2009, Journal of ethnopharmacology.

[5]  Takashi Suzuki,et al.  New cytotoxic diarylheptanoids from the rhizomes of Alpinia officinarum. , 2008, Planta medica.

[6]  Xiaofeng Ma,et al.  Antimicrobial effect by extracts of rhizome of Alpinia officinarum Hance may relate to its inhibition of beta-ketoacyl-ACP reductase. , 2008, Journal of enzyme inhibition and medicinal chemistry.

[7]  Z. Zou,et al.  Diarylheptanoids from Alpinia officinarum , 2006, Journal of Asian natural products research.

[8]  H. Matsuda,et al.  Inhibitors from the rhizomes of Alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity. , 2006, Bioorganic & medicinal chemistry.

[9]  M. Shimoyamada,et al.  Isolation and characterization of some antioxidative compounds from the rhizomes of smaller galanga (Alpinia officinarum Hance). , 2003, Journal of agricultural and food chemistry.

[10]  K. Kinoshita,et al.  Antiemetic principles of Alpinia officinarum. , 2002, Journal of natural products.