Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones.
Seven hydroxyanthraquinone derivatives, 1-7, were isolated from the root of Rheum palmatum (Polygonaceae). Two propionated anthraquinone derivatives, 8 and 9, were synthesized. Four hydroxynaphthoquinone derivatives, 13, 14, 16 and 21, were isolated from the root of Lithospermum erythrorhizon Sieb. et Zucc. (Boraginaceae) and also three naphthoquinone derivatives, 19, 22 and 23, were isolated from the root of Macrotomia euchroma (Royle) Pauls. (Boraginaceae). The cytotoxicity of the anthraquinone and naphthoquinone derivatives on P-gp-underexpressing HCT 116 cells and P-gp-overexpressing Hep G2 cells was examined by MTT assay. Among the anthraquinone derivatives, compounds 3-5 which had OH, CH(2)OH and COOH substituent groups on the anthraquinone skeletons, respectively, showed potent growth inhibitory activities against both types of cancer cells (IC(50) values: 5.7+/-0.9 to 13.0+/-0.7 microM in the case of HCT 116 cells and 5.2+/-0.7 to 12.3+/-0.9 microM in the case of Hep G2 cells). All hydroxynaphthoquinone derivatives isolated in this study exhibited extremely potent growth inhibitory activities against both types of cancer cells (IC(50) values: 0.3+/-0.09 to 0.46+/-1.0 microM in the case of HCT 116 cells and 0.22+/-0.03 to 0.59+/-0.06 microM in the case of Hep G2 cells) as well as shikonin 10 (IC(50) values: 0.32+/-0.02 microM in the case of HCT 116 cells and 0.24+/-0.03 microM in the case of Hep G2 cells).
Cui
Xing-Ri
XR
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai 1-1, Sakado, Saitama 350-0295, Japan.
Tsukada
Maiko
M
Suzuki
Nao
N
Shimamura
Takeshi
T
Gao
Li
L
Koyanagi
Jyunichi
J
Komada
Fusao
F
Saito
Setsuo
S
D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D028082:Boraginaceae / Q000737:chemistry; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D029684:Lithospermum / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D012250:Rheum / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D000880:Anthraquinones; D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones