Glycolipids from the aerial parts of Orostachys japonicus with fatty acid synthase inhibitory and cytotoxic activities

Title
Glycolipids from the aerial parts of Orostachys japonicus with fatty acid synthase inhibitory and cytotoxic activities
Author(s)
나민균장해연오준석[오준석]장태수[장태수]민병선[민병선]
Keywords
CANCER-CELLS; APOPTOSIS; TARGETS
Issue Date
201204
Publisher
ELSEVIER SCI LTD
Citation
FOOD CHEMISTRY, v.131, no.4, pp.1097 - 1103
Abstract
Inhibition of fatty acid synthase (FAS) has been proposed as a new therapeutic target for the treatment of cancer. In our preliminary study, a MeOH extract of the aerial parts of Orostachys japonicus A. Berger (Crassulaceae) inhibited FAS activity (>95% inhibition at 62.5 mu g/mL). Through bioassay-guided fractionation, we isolated three cerebrosides (1-3), including one new compound (1), and seven glyceroglycolipids (4-10) from a FAS inhibitory hexane-soluble fraction of the MeOH extract of O. japonicus. On the basis of physicochemical and spectroscopic analyses including 10 and 20 NMR, HRFABMS, and ESIMS/MS, the structure of the new compound 1 was 1-O-(beta-D-glucopyranosyl)-(2S,3S,4R,6Z,10E)-2-[(2'R,6'Z,9'Z)-2-hydroxyeicosa-6',9'-dienoylamino)]-1,3,4-trihydroxytetracosa-6,10-diene, and it was named orostachyscerebroside A. Compounds 1-10 were tested for their in vitro FAS inhibitory activity, and compounds 1, 4, 5, 6, 7, and 8 inhibited the enzyme with micro-molar IC(50) values both in the incorporation of [(3)H] acetyl CoA (from 52.2 to 108.0 mu M) and in the oxidation of NADPH (from 19.5 to 30.3 mu M). Interestingly, compounds 1, 4, 5, 6, 7, and 8 with FAS inhibitory activity showed cytotoxic activity against HL-60 (human leukemia) and A549 (human lung adenocarcinoma) cancer cells, while none of them displayed cytotoxicity against MCF-7 (human breast adenocarcinoma) cells. This is the first report on the inhibition of FAS by glycolipids from O. japonicus and their cytotoxic activity and may provide a scientific basis for the folk remedy using the plant to treat cancer. (C) 2011 Elsevier Ltd. All rights reserved.
URI
http://hdl.handle.net/YU.REPOSITORY/28621http://dx.doi.org/10.1016/j.foodchem.2011.09.058
ISSN
0308-8146
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약학대학 > 약학부 > Articles
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