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The Pharmaceutical Society of Korea (대한약학회)
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Cytotoxicity and DNA Topoisomerase Inhibitory Activity of Constituents Isolated from the Fruits of Evodia officinalis

  • Xu, Ming-Lu (College of Pharmacy, Yeungnam University) ;
  • Li, Gao (Key Laboratory of Natural Resources of the Changbai Mountain and Functional Molecules (Yanbian University), Ministry of Education,College of Pharmacy, Yanbian University) ;
  • Moon, Dong-Cheol (College of Pharmacy, Chungbuk National University) ;
  • Lee, Chong-Soon (Department of Biochemistry, College of Natural Sciences, Yeungnam University) ;
  • Woo, Mi-Hee (College of Pharmacy, Catholic University of Daegu) ;
  • Lee, Eung-Seok (College of Pharmacy, Yeungnam University) ;
  • Jahng, Yurng-Dong (College of Pharmacy, Yeungnam University) ;
  • Chang, Hyeun-Wook (College of Pharmacy, Yeungnam University) ;
  • Lee, Seung-Ho (College of Pharmacy, Yeungnam University) ;
  • Son, Jong-Keun (College of Pharmacy, Yeungnam University)
  • Published : 2006.07.01
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Abstract

Four alkaloids (1-4), three quinolone alkaloids (5-7), and three flavanoid glucosides (8-10) were isolated from the fruits of Evodia officinalis Dode, and their structures were determined from chemical and spectral data. Compounds, 3, 8, 9 and 10 were isolated from this plant for the first time. Of these compounds, 1-3 and 5-7 exhibited moderate cytotoxicities against cultured human colon carcinoma (HT-29), human breast carcinoma (MCF-7), and human hepatoblastoma (HepG-2). Compound 8 showed strong inhibitory effects on DNA topoisomerases I and II (70 and 96% inhibition at a concentration of $20\;{\mu}M$, respectively).

Keywords

References

  1. Ahmed, A., Ishak, M. S., Micheal, H. N., El-ansari, M. A., and El-Sissi, H. I., Flavonoids of Asteriscus fraveolens, 54, 1092- 1093 (1991)
  2. Akira, I., Hisaom, U., and Takayuki, N., A new indolopyridoquinazoline- type alkaloid from Phellodendron amurense Callus Tissues. J. Nat. Prod., 61, 1012-1014 (1988)
  3. Asano, N., Kato, A., Kizu, H., and Matsui, K., 1${\beta}$-amino- 2${\alpha}$,3${\beta}$,5${\beta}$-trihydroxycy-cloheptane from Physalis alkekengi var. francheti. Phytochemistry, 42(3), 719-721 (1996) https://doi.org/10.1016/0031-9422(96)00034-9
  4. Ulubelen, A., Timmermann, N., and Mabry, T. J., Flavonoids from Brickellia chlorolepis and B. Dentata., Phytochemistry, 19, 905-908 (1980) https://doi.org/10.1016/0031-9422(80)85136-3
  5. Bergman J. and Bergamn S., Strudies of rutaecarpine and related quinazolinocar-boline alkaloids. J. Org. Chem., 50, 1246-1255 (1985) https://doi.org/10.1021/jo00208a018
  6. Buschi, C. A. and Pomilio, A. B., Isorhamentin 3-O-robinobioside from Gomphrena Martiana. J. Nat. Prod., 45, 557-559 (1982) https://doi.org/10.1021/np50023a007
  7. Chen, A. Y. and Liu, L. F., DNA topoisomerase: essential enzymes and lethal targets. Annu. Rev. Pharmacol. Toxicol., 34, 191-218 (1994) https://doi.org/10.1146/annurev.pa.34.040194.001203
  8. Crawford, D., Flavonoid chemistry of Chenopodium fremontii. Infraspecific variation and systematic implications at the interspecific level. J. Biochem. Syst. Ecol., 6, 189. (1978) https://doi.org/10.1016/0305-1978(78)90006-6
  9. D'Arpa, P. and Liu, L. F., Topoisomerase-targeting antirumor drugs. Biochim. Biophys. Acta., 989, 163-177 (1998)
  10. Fukuda, M., Nishio, K., Kanzawa, F., Ogasawara, H., Ishida, T., Arioka, H., Bojamowski, K., Oka, M., and Saijo, N., Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells. Cancer Res., 56, 789-793 (1996)
  11. Harborne, J. B., Two Gossypetin methyl ethers as ultraviolet patterning guides in the Flowers of Coronilla valentine. Phytochemistry, 20, 1117-1119 (1981) https://doi.org/10.1016/0031-9422(81)83038-5
  12. Ikuta, A., Nakamura, T., and Urabe, H., Indolopyridoquinazoline, furoquinoline and canthinone type alkaloids from Phellodendron amurense Callus Tissues. Phytochemistry, 48, 285-291 (1998) https://doi.org/10.1016/S0031-9422(97)01130-8
  13. Ikuta, A., Urabe, H., and Nakamura, T., A new indolopyridoquinazoline- type alkaloid from Phellodendron amurense Callus Tissues. J. Nat. Prod., 61, 1012-1014 (1988)
  14. Ito, Y., Nishitani, E., Konoshima, T., Takasaki, M., Kozuka, M., and Yoshida, T., Flavonoid and benzophenone glycosides from Coleogyne ramosissima. Phytochemistry, 54, 695-700 (2000) https://doi.org/10.1016/S0031-9422(00)00192-8
  15. Liu, L. F., DNA topoisomerase poisons as antitumor drugs. Annu. Rev. Biochem., 58, 351-375 (1989) https://doi.org/10.1146/annurev.bi.58.070189.002031
  16. Pommier, Y., DNA topoisomerase I and II in cancer chemotherapy: update and perspectives. Cancer Chemother. Pharmacol., 32, 103-108 (1993) https://doi.org/10.1007/BF00685611
  17. Potmesil, M., Camptothecins: from bench research to hospital wards. Cancer Res., 54, 1431-1439 (1994)
  18. Rubinstein, L. V., Shoemaker, R. H., Paul, K. D., Simon, R. M., Tosini, S., Skehan, P., Scudiero, D. A., Monks, A., and Boyd, M. R., Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J. Nat. Cancer Inst., 82, 1113-1118 (1990) https://doi.org/10.1093/jnci/82.13.1113
  19. Slichenmyer, W. J., Rowinsky, E. K., Donehower, R. C., and Kaufmann, S. H., The current status of camptothecin analogues as antitumor agents. J. Natl. Cancer Inst., 85, 271-291 (1993) https://doi.org/10.1093/jnci/85.4.271
  20. Sugimoto, T., Miyase, T., Kuroyanagi, M., and Ueno, A., Limonoids and quinolone alkaloids from Evodia rutaecarpa Bentham. Chem. Pharm. Bull., 36, 4453-4461 (1988) https://doi.org/10.1248/cpb.36.4453
  21. Ulubelen, A., Oksuz, S., Halfon, B., Aynehchi, Y., Mabry, T. J., and Matlin, S. A., Flavonoids from Haplophyllum pedicellatum, H. robustum and H. glabrinum. Phytochemistry, 23, 2941-2943 (1984) https://doi.org/10.1016/0031-9422(84)83046-0
  22. Ulubelen, A., Barbara, N., and Tom J. M., Flavonoids from brickellia chlorolepis and B. Dentata. Phytochemistry, 19, 905-908 (1980) https://doi.org/10.1016/0031-9422(80)85136-3
  23. Wang, J. C., DNA topoisomerases. Annu. Rev. Biochem., 65, 635-692 (1996) https://doi.org/10.1146/annurev.bi.65.070196.003223
  24. Wang, Y., Hamburger, M., Gueho, J., and Hostettmann, K., Antimicrobial. Flavonoids from Psiadia trinervia and their methylated and acetylated derivatives. Phytochemistry, 28, 2323-2327 (1989) https://doi.org/10.1016/S0031-9422(00)97976-7
  25. Wattanapiromsakul, C., Forster, P. I., and Waterman, P. G., Alkaloids and limonoids from Bouchardatia neurococca: systematic significance. Phytochemistry, 64, 609-615 (2003) https://doi.org/10.1016/S0031-9422(03)00205-X
  26. Tang, Y. Q., Feng, X. Z., and Huang, L., Quinolone alkaloids from Evodia futaecarpa. Phytochemistry, 43, 719-722 (1996) https://doi.org/10.1016/0031-9422(96)00304-4
  27. Zuo, G. Y., Yang, X. S., and Hao, X. J., Two new indole alkaloids from Evodia rutaecarpa. Chinese Chem. Lett., 11, 127-128 (2000)