Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata |
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Authors: | Lee Byong Won Lee Jin Hwan Lee Sung-Tae Lee Hyun Sun Lee Woo Song Jeong Tae-Sook Park Ki Hun |
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Institution: | aDepartment of Agricultural Chemistry, Division of Applied Life Science, Institute of Agriculture & Life Science, Gyeongsang National University, Jinju 660-701, Republic of Korea bDepartment of Biology, Sunchon National University, Sunchon, Republic of Korea cKorea Research Institute of Bioscience and Biotechnology, 52 Oun, Yusong, Daejeon 305-333, Republic of Korea |
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Abstract: | The new catecholic xanthone, 1,3,7-trihydroxy-4-(1,1-dimethyl-2-propenyl)-5,6-(2,2-dimethylchromeno)-xanthone (1), was isolated from the root bark of Cudrania tricuspidata together with seven known xanthones. The structures were fully characterized by analysis of physical and spectral (UV, IR, mass, and NMR) data. Relationships between the structural characteristics of xanthones and their antioxidant activities (DPPH, superoxide, and hydroxyl radical) were studied. Among the range of catecholic xanthones, 6,7-dihydroxyl xanthones (3–8) exhibited a strong scavenging effect on the DPPH radical. When one of the catecholic hydroxyl groups was protected as in compounds 1 and 2, DPPH radical scavenging activity was markedly decreased (IC50 > 200 μM). DPPH activities were consistent with electrochemical response by cyclic voltammetry. Interestingly, compounds (1, 2) which had the weak activities on DPPH, exhibited both potent superoxide and hydroxyl radical scavenging activities. The strong activity on the hydroxyl radical of compounds (1, 2) could be rationalized by their chelating effect with iron (Fe2+) due to a redshift of its complex. The catecholic xanthones (3–8), being able to convert quinone methide intermediate, showed potent cytotoxicities against human cancer cell lines (HT-29, HL-60, SK-OV3, AGS, and A549). In particular, compounds 3, 6, and 7 had strong cytotoxic activities against AGS (LD50 < 5 μM). DNA fragmentation patterns induced by catecholic xanthones revealed that tumor cell death was due to apoptosis. |
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Keywords: | Antioxidant activity Catecholic xanthones Cudrania tricuspidata Cytotoxicity |
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