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Cytotoxic effects of new geranyl chalcone derivatives isolated from the leaves of Artocarpus communis in SW 872 human liposarcoma cells.
J Agric Food Chem. 2008 Oct 08; 56(19):8859-68.JA

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 1- 5 were elucidated by spectroscopy and through comparison with data reported in the literature. The effects of geranyl chalcone derivatives (1- 5) 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 IC 50 value of 3.8 muM in SW 872 human liposarcoma cells. Treatment of SW 872 human liposarcoma cells with isolespeol (1) caused the loss of mitochondrial membrane potential (DeltaPsim). 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.

Authors+Show Affiliations

Department of Food Nutrition, Chung Hwa University of Medical Technology, 89 Wenhwa First Street, Tainan 71703, Taiwan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18767861

Citation

Fang, Song-Chwan, et al. "Cytotoxic Effects of New Geranyl Chalcone Derivatives Isolated From the Leaves of Artocarpus Communis in SW 872 Human Liposarcoma Cells." Journal of Agricultural and Food Chemistry, vol. 56, no. 19, 2008, pp. 8859-68.
Fang SC, Hsu CL, Yu YS, et al. Cytotoxic effects of new geranyl chalcone derivatives isolated from the leaves of Artocarpus communis in SW 872 human liposarcoma cells. J Agric Food Chem. 2008;56(19):8859-68.
Fang, S. C., Hsu, C. L., Yu, Y. S., & Yen, G. C. (2008). Cytotoxic effects of new geranyl chalcone derivatives isolated from the leaves of Artocarpus communis in SW 872 human liposarcoma cells. Journal of Agricultural and Food Chemistry, 56(19), 8859-68. https://doi.org/10.1021/jf8017436
Fang SC, et al. Cytotoxic Effects of New Geranyl Chalcone Derivatives Isolated From the Leaves of Artocarpus Communis in SW 872 Human Liposarcoma Cells. J Agric Food Chem. 2008 Oct 8;56(19):8859-68. PubMed PMID: 18767861.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cytotoxic effects of new geranyl chalcone derivatives isolated from the leaves of Artocarpus communis in SW 872 human liposarcoma cells. AU - Fang,Song-Chwan, AU - Hsu,Chin-Lin, AU - Yu,Yu-Shen, AU - Yen,Gow-Chin, Y1 - 2008/09/04/ PY - 2008/9/5/pubmed PY - 2008/12/20/medline PY - 2008/9/5/entrez SP - 8859 EP - 68 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 56 IS - 19 N2 - 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 1- 5 were elucidated by spectroscopy and through comparison with data reported in the literature. The effects of geranyl chalcone derivatives (1- 5) 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 IC 50 value of 3.8 muM in SW 872 human liposarcoma cells. Treatment of SW 872 human liposarcoma cells with isolespeol (1) caused the loss of mitochondrial membrane potential (DeltaPsim). 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. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/18767861/Cytotoxic_effects_of_new_geranyl_chalcone_derivatives_isolated_from_the_leaves_of_Artocarpus_communis_in_SW_872_human_liposarcoma_cells_ L2 - https://doi.org/10.1021/jf8017436 DB - PRIME DP - Unbound Medicine ER -