کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1375476 981939 2005 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata
چکیده انگلیسی

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.

The eight catecholic xanthones with antioxidant and cytotoxic activities were isolated from Cudrania tricuspidata. Catecholic xanthones possessed potent various free radical scavenging activities and also cytotoxicities against human cancer cell lines.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 15, Issue 24, 15 December 2005, Pages 5548–5552
نویسندگان
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