Advertisement

Archives of Pharmacal Research

, Volume 29, Issue 7, pp 541–547 | Cite as

Cytotoxicity and DNA topoisomerase inhibitory activity of constituents isolated from the fruits ofEvodia officinalis

  • Ming-Lu Xu
  • Dong-Cheol Moon
  • Chong-Soon Lee
  • Mi-Hee Woo
  • Eung Seok Lee
  • Yurngdong Jahng
  • Hyeun-Wook Chang
  • Seung-Ho Lee
  • Jong-Keun SonEmail author
Articles Drug Design

Abstract

Four alkaloids (1–4), three quinolone alkaloids (5–7), and three flavanoid glucosides (8–10) were isolated from the fruits ofEvodia officinalis Dode, and their structures were determined from chemical and spectral data. Compounds,3, 8, 9 and10 were isolated from this plant for the first time. Of these compounds,1–3 and5–7 exhibited moderate cytotoxicities against cultured human colon carcinoma (HT-29), human breast carcinoma (MCF-7), and human hepatoblastoma (HepG-2). Compound8 showed strong inhibitory effects on DNA topoisomerases I and II (70 and 96% inhibition at a concentration of 20 μM, respectively).

Key words

Evodia officinalis DNA topoisomerases I and II inhibitors Cytotoxicity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Ahmed, A., Ishak, M. S., Micheal, H. N., El-ansari, M. A., and El-Sissi, H. I., Flavonoids ofAsteriscus fraveolens, 54, 1092–1093 (1991).Google Scholar
  2. Akira, I., Hisaom, U., and Takayuki, N., A new indolopyridoquinazoline-type alkaloid fromPhellodendron amurense Callus Tissues.J. Nat. Prod., 61, 1012–1014 (1988).Google Scholar
  3. Asano, N., Kato, A., Kizu, H., and Matsui, K., 1β-amino-2α,3β,5β-trihydroxycy-cloheptane fromPhysalis alkekengi var.francheti.Phytochemistry, 42(3), 719–721 (1996).CrossRefGoogle Scholar
  4. Ulubelen, A., Timmermann, N., and Mabry, T. J., Flavonoids fromBrickellia chlorolepis andB. Dentata., Phytochemistry, 19, 905–908 (1980).CrossRefGoogle Scholar
  5. Bergman, J. and Bergamn S., Strudies of rutaecarpine and related quinazolinocar-boline alkaloids.J. Org. Chem., 50, 1246–1255 (1985).CrossRefGoogle Scholar
  6. Buschi, C. A. and Pomilio, A. B., Isorhamentin 3-O-robinobioside fromGomphrena Martiana.J. Nat. Prod., 45, 557–559 (1982).CrossRefGoogle Scholar
  7. Chen, A. Y. and Liu, L. F., DNA topoisomerase: essential enzymes and lethal targets.Annu. Rev. Pharmacol. Toxicol., 34, 191–218 (1994).PubMedCrossRefGoogle Scholar
  8. Crawford, D., Flavonoid chemistry ofChenopodium fremontii. Infraspecific variation and systematic implications at the interspecific level.J. Biochem. Syst. Ecol., 6, 189. (1978).CrossRefGoogle Scholar
  9. D'Arpa, P. and Liu, L. F., Topoisomerase-targeting antirumor drugs.Biochim. Biophys. Acta., 989, 163–177 (1998).Google Scholar
  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).PubMedGoogle Scholar
  11. Harborne, J. B., Two Gossypetin methyl ethers as ultraviolet patterning guides in the Flowers ofCoronilla valentine.Phytochemistry, 20, 1117–1119 (1981).CrossRefGoogle Scholar
  12. Ikuta, A., Nakamura, T., and Urabe, H., Indolopyridoquinazoline, furoquinoline and canthinone type alkaloids fromPhellodendron amurense Callus Tissues.Phytochemistry, 48, 285–291 (1998).CrossRefGoogle Scholar
  13. Ikuta, A., Urabe, H., and Nakamura, T., A new indolopyridoquinazoline-type alkaloid fromPhellodendron amurense Callus Tissues.J. Nat. Prod., 61, 1012–1014 (1988).CrossRefGoogle Scholar
  14. Ito, Y., Nishitani, E., Konoshima, T., Takasaki, M., Kozuka, M., and Yoshida, T., Flavonoid and benzophenone glycosides fromColeogyne ramosissima.Phytochemistry, 54, 695–700 (2000).PubMedCrossRefGoogle Scholar
  15. Liu, L. F., DNA topoisomerase poisons as antitumor drugs.Annu. Rev. Biochem., 58, 351–375 (1989).PubMedCrossRefGoogle Scholar
  16. Pommier, Y., DNA topoisomerase I and II in cancer chemotherapy: update and perspectives.Cancer Chemother. Pharmacol., 32, 103–108 (1993).PubMedCrossRefGoogle Scholar
  17. Potmesil, M., Camptothecins: from bench research to hospital wards.Cancer Res., 54, 1431–1439 (1994).PubMedGoogle Scholar
  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 ofin 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).PubMedCrossRefGoogle Scholar
  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).PubMedCrossRefGoogle Scholar
  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).Google Scholar
  21. Ulubelen, A., Öksüz, S., Halfon, B., Aynehchi, Y., Mabry, T. J., and Matlin, S. A., Flavonoids fromHaplophyllum pedicellatum, H. robustum andH. glabrinum.Phytochemistry, 23, 2941–2943 (1984).CrossRefGoogle Scholar
  22. Ulubelen, A., Barbara, N., and Tom, J. M., Flavonoids frombrickellia chlorolepis andB. Dentata.Phytochemistry, 19, 905–908 (1980).CrossRefGoogle Scholar
  23. Wang, J. C., DNA topoisomerases.Annu. Rev. Biochem., 65, 635–692 (1996).PubMedCrossRefGoogle Scholar
  24. Wang, Y., Hamburger, M., Gueho, J., and Hostettmann, K., Antimicrobial. Flavonoids fromPsiadia trinervia and their methylated and acetylated derivatives.Phytochemistry, 28, 2323–2327 (1989).CrossRefGoogle Scholar
  25. Wattanapiromsakul, C., Forster, P. I., and Waterman, P. G., Alkaloids and limonoids fromBouchardatia neurococca: systematic significance.Phytochemistry, 64, 609–615 (2003).PubMedCrossRefGoogle Scholar
  26. Tang, Y. Q., Feng, X. Z., and Huang, L., Quinolone alkaloids fromEvodia futaecarpa.Phytochemistry, 43, 719–722 (1996).CrossRefGoogle Scholar
  27. Zuo, G. Y., Yang, X. S., and Hao, X. J., Two new indole alkaloids fromEvodia rutaecarpa.Chinese Chem. Lett. 11, 127–128 (2000).Google Scholar

Copyright information

© The Pharmaceutical Society of Korea 2006

Authors and Affiliations

  • Ming-Lu Xu
    • 2
    • 3
  • Dong-Cheol Moon
    • 4
  • Chong-Soon Lee
    • 5
  • Mi-Hee Woo
    • 6
  • Eung Seok Lee
    • 1
  • Yurngdong Jahng
    • 1
  • Hyeun-Wook Chang
    • 1
  • Seung-Ho Lee
    • 1
  • Jong-Keun Son
    • 1
    Email author
  1. 1.College of PharmacyYeungnam UniversityGyongsanKorea
  2. 2.Key Laboratory of Natural Resources of the Changbai Mountain and Functional Molecules (Yanbian University)Ministry of EducationYanjiChina
  3. 3.College of PharmacyYanbian UniversityYanjiChina
  4. 4.College of PharmacyChungbuk National UniversityCheongjuKorea
  5. 5.Department of Biochemistry, College of Natural SciencesYeungnam UniversityGyongsanKorea
  6. 6.College of PharmacyCatholic University of DaeguGyongsanKorea

Personalised recommendations