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Title 

Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata

Authors 

B W LeeJ H LeeS T LeeHyun Sun LeeWoo Song LeeTae Sook JeongK H Park

Publisher 

Elsevier

Issue Date 

2005

Citation 

Bioorganic & Medicinal Chemistry Letters, vol. 15, no. 24, pp. 5548-5552

Keywords 

antioxidant activitycatecholic xanthonescudrania tricuspidatacytotoxicity1,3,7 trihydroxy 4 (1,1 dimethyl 2 propenyl) 5,6 (2,2 dimethylchromeno) xanthoneantioxidantxanthone derivativeantineoplastic activitydrug cytotoxicity

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 (LD 50 < 5 μM). DNA fragmentation patterns induced by catecholic xanthones revealed that tumor cell death was due to apoptosis.

ISSN 

0960-894X

Link 

http://dx.doi.org/10.1016/j.bmcl.2005.08.099

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2017-04-19


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