Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata.
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 (IC(50)>200microM). 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 (Fe(2+)) 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)<5microM). DNA fragmentation patterns induced by catecholic xanthones revealed that tumor cell death was due to apoptosis.
Lee
Byong Won
BW
Department of Agricultural Chemistry, Division of Applied Life Science, Institute of Agriculture & Life Science, Gyeongsang National University, Jinju 660-701, Republic of Korea.
Lee
Jin Hwan
JH
Lee
Sung-Tae
ST
Lee
Hyun Sun
HS
Lee
Woo Song
WS
Jeong
Tae-Sook
TS
Park
Ki Hun
KH
D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D000975:Antioxidants / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D029586:Moraceae / Q000737:chemistry*; D010084:Oxidation-Reduction; D044004:Xanthones / Q000302:isolation & purification* / Q000494:pharmacology
D000970:Antineoplastic Agents; D000975:Antioxidants; D044004:Xanthones