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Cytotoxic Effects of New Geranyl Chalcone Derivatives Isolated from the Leaves of Artocarpus communis in SW 872 Human Liposarcoma Cells

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Department of Food Nutrition, Chung Hwa University of Medical Technology, 89 Wenhwa First Street, Tainan 71703, Taiwan, and Department of Food Science and Biotechnology, National Chung Hsing University, 250 Kuokuang Road, Taichung 40227, Taiwan
* To whom correspondence should be addressed. Tel: 886-4-2287-9755. Fax: 886-4-2285-4378. E-mail: [email protected]
†Chung Hwa University of Medical Technology.
‡National Chung Hsing University.
Cite this: J. Agric. Food Chem. 2008, 56, 19, 8859–8868
Publication Date (Web):September 4, 2008
https://doi.org/10.1021/jf8017436
Copyright © 2008 American Chemical Society

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    Abstract

    Breadfruit (Artocarpus communis Moraceae) is cultivated in tropical and subtropical regions as a traditional starch crop and also has potential medicinal properties. The aim of this work was to study the in vitro anticancer activity of compounds isolated from the leaves of Artocarpus communis. Three new geranyl chalcone derivatives including isolespeol (1), 5′-geranyl-2′,4′,4-trihydroxychalcone (2), and 3,4,2′,4′-tetrahydroxy-3′-geranyldihydrochalcone (3), together with two known compounds lespeol (4) and xanthoangelol (5), were isolated from the leaves of Artocarpus communis. The structures of 15 were elucidated by spectroscopy and through comparison with data reported in the literature. The effects of geranyl chalcone derivatives (15) on the viability of human cancer cells (including SW 872, HT-29, COLO 205, Hep3B, PLC5, Huh7, and HepG2 cells) were investigated. The results indicate that isolespeol (1) showed the highest inhibitory activity with an IC50 value of 3.8 μM in SW 872 human liposarcoma cells. Treatment of SW 872 human liposarcoma cells with isolespeol (1) caused the loss of mitochondrial membrane potential (ΔΨm). Western blotting revealed that isolespeol (1) stimulated increased protein expression of Fas, FasL, and p53. The expression ratios of pro- and antiapoptotic Bcl-2 family members were also changed by isolespeol (1) treatment to subsequently induce the activation of caspase-9 and caspase-3, which was followed by cleavage of poly (ADP-ribose) polymerase (PARP). These results demonstrate that isolespeol (1) induces apoptosis in SW 872 cells through Fas- and mitochondria-mediated pathways.

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