An oxepinoflavone from Artocarpus elasticus with cytotoxic activity against P-388 cells

  • Iqbal Musthapa
  • Lia D. Juliawaty
  • Yana M. Syah
  • Euis H. Hakim
  • Jalifah Latip
  • Emilio L. Ghisalberti
Research Articles Drug Discovery and Development


A new oxepinoflavone, artoindonesianin E1 (1), was isolated from the wood of Artocarpus elasticus, along with four known prenylated flavones: artocarpin (2), cycloartocarpin (3), cudraflavones A (4) and C (5). The structure of the new compound was identified by spectroscopic methods. Upon cytotoxic evaluation against murine leukemia P-388 cells, the new compound showed IC50 5.0 μg/mL.

Key words

Artocarpus elasticus Flavonoids Oxepinoflavone Artoindonesianin E1 Cytotoxicity P-388 cells 


  1. Cerqueira, F., Cidade, H., van Ufford, L., Beukelman, C., Kijjoa, A., and Nascimento, M. S. J., The natural prenylated flavone artelastin is an inhibitor of ROS and NO production. Intl. Immunopharmacol., 8, 597–602 (2008).CrossRefGoogle Scholar
  2. Cidade, H. M., Nacimento, M. S. J., Pinto, M. M. M., Kijjoa, A., Silva, A. M. S., and Herz, W., Artelastocarpin and carpelastofuran, two new flavones, and cytotoxicities of prenyl flavonoids from Artocarpus elasticus against three cancer cell lines. Planta Med., 67, 867–870 (2001).PubMedCrossRefGoogle Scholar
  3. Hakim, E. H., Achmad, S. A., Juliawaty, L. D., Makmur, L., Syah, Y. M., Aimi, N., Kitajima, M., Hiromitsu, H., and Ghisalberti, E. L., Prenylated flavonoids and related compounds on the Indonesian Artocarpus (Moraceae). J. Nat. Med., 60, 161–184 (2006).Google Scholar
  4. Hakim, E. H., Fahriyati, A., Kau, M. S., Achmad, S. A., Makmur, L., Ghisalberti, E. L., and Nomura, T., Artoindonesianins A and B, two new prenylated flavones from the root of Artocarpus champeden. J. Nat. Prod., 62, 613–615 (1999).PubMedCrossRefGoogle Scholar
  5. Hano, Y., Matsumoto, Y., Shinohara, K., Sun, J., and Nomura, T. Constituents of the Moraceae plants. 10. Cudraflavones C and D, two new prenylflavones from the root bark of Cudrania tricuspidata (Carr.) Bur. Heterocycles, 31, 1339–1344 (1990).Google Scholar
  6. Heyne, K., The Useful Indonesian Plants. Research and Development Agency, Ministry of Forestry, Jakarta, Indonesia, p. 676 (1987).Google Scholar
  7. Kijjoa, A., Cidade, H. M., Pinto, M. M. M., Gonzalez, M. J. T. G., Anantachoke, C., Gedris, T. E., and Herz, W., Prenylflavonoids from Artocarpus elasticus. Phytochemistry, 43, 691–694 (1996).CrossRefGoogle Scholar
  8. Kijjoa, A., Cidade, H M., Gonzalez, M. J. T. G., Afonso, C. M., Silva, A. M. S., and Herz, W., Further prenylflavonoids from Artocarpus elasticus. Phytochemistry, 47, 875–878 (1998).CrossRefGoogle Scholar
  9. Ko, H. -H., Lu, Y. -H., Yang, S. -Z., Won, S. -J., and Lin, C. -N. Cytotoxic prenylflavonoids from Artocarpus elasticus. J. Nat. Prod., 68, 1692–1695 (2005).PubMedCrossRefGoogle Scholar
  10. Lin, C. -N., Lu, C. -M., and Huang, P. -L., Flavonoids from Artocarpus heterophyllus. Phytochemistry, 39, 1447–1451 (1995).CrossRefGoogle Scholar
  11. Lu, C. M. and Lin, C. N., Flavonoids and 9-hydroxytridecyl docosanoate from Artocarpus heterophyllus. Phytochemistry, 35, 781–783 (1994).CrossRefGoogle Scholar
  12. Mabry, T. J., Markham, K. R., and Thomas, M. B., The Systematic Identification of Flavonoids, Springer-Verlag, New York, pp. 41–164 (1970).Google Scholar
  13. Nair, A. G. R., Vijayan, V. K., and Sethumadhavan, C. V., Confirmation of structure of cycloartocarpin from Artocarpus hirsutus. Indian J. Chem., 29B, 881–882 (1990).Google Scholar
  14. Nascimento, M. S. J., Cidade, H., Pinto, M., and Kijjoa, A., Anticomplementary activity of prenylated flavones from Artocarpus elasticus. Pharm. Pharmacol. Lett., 7, 135–137 (1997).Google Scholar
  15. Nomura, T. and Hano, Y., Isoprenoid-substituted phenolic compounds of moraceous plants. Nat. Prod. Rep., 11, 205–218 (1994).PubMedCrossRefGoogle Scholar
  16. Nomura, T., Hano, Y., and Aida, M., Isoprenoid-substituted flavonoids from Artocarpus plants (Moraceae). Heterocycles, 47, 1179–1205 (1998).CrossRefGoogle Scholar
  17. Pedro, M., Ferreira, M. M., Cidade, H., Kijjoa, A., Bronze-da-Rocha, E., and Nascimento, M. S. J., Artelastin is a cytotoxic prenylated flavone that disturbs microtubules and interferes with DNA replication in MCF-7 human breast cancer cells. Life Sci., 77, 293–311 (2005).PubMedCrossRefGoogle Scholar
  18. Sahidin, Hakim, E. H., Juliawaty, L. D., Syah, Y. M., Din, L. B., Ghisalberti, E. L., Latip, J., Said, I. M., and Achmad, S. A., Cytotoxic properties of oligostilbenoids from the tree bark of Hopea dryobalanoides. Z. Naturforsch., 60c, 723–727 (2005).Google Scholar
  19. Syah, Y. M., Hakim, E. H., Makmur, L., Kurdi, V. A., Ghisalberti, E. L., Aimi, N., and Achmad, S. A., Prenylated 2-arylbenzofurans from two species of Artocarpus. Nat. Prod. Commun., 1, 549–552 (2006a).Google Scholar
  20. Syah, Y. M., Juliawaty, L. D., Hakim, E. H., Achmad, S. A., and Ghisalberti, E. L. Cytotoxic prenylated flavones from Artocarpus champeden. J. Natur. Med., 60, 308–312 (2006b).CrossRefGoogle Scholar
  21. Syah, Y. M., Achmad, S. A., Aimi, N., Hakim, E. H., Juliawaty, L. D., and Hiromitsu, H., Two prenylated flavones from the tree bark of Artocarpus lanceifolius. Z. Naturforsch., 61b, 1134–1137 (2006c).Google Scholar
  22. Wang, Y. -H., Hou, A. -J., Chen, L., Chen, D. -F., Sun, H. -D., Zhao, Q. -S., Bastow, K. F., Nakanish, Y., Wang, X. -H., and Lee, K. -H., New isoprenylated flavones, artochamins A-E, and cytotoxic principles from Artocarpus chama. J. Nat. Prod., 67, 757–761 (2004).PubMedCrossRefGoogle Scholar
  23. Wei, B. -L., Weng, J. -R., Chiu, P. -H., Hung, C. -F., Wang, J. -P., and Lin, C. -N. Antiinflammatory flavonoids from Artocarpus heterophyllus and Artocarpus communis. J. Agric. Food Chem., 53, 3867–3871 (2005).PubMedCrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 2009

Authors and Affiliations

  • Iqbal Musthapa
    • 1
  • Lia D. Juliawaty
    • 1
  • Yana M. Syah
    • 1
  • Euis H. Hakim
    • 1
  • Jalifah Latip
    • 2
  • Emilio L. Ghisalberti
    • 3
  1. 1.Institut Teknologi BandungNatural Products Research Group, Faculty of Mathematics and Natural SciencesBandungIndonesia
  2. 2.School of Chemistry and Food Technology, Faculty of Science and TechnologyNational University of MalaysiaBangiMalaysia
  3. 3.Chemistry, School of Biomedical, Biomolecular and Chemical SciencesUniversity of Western AustraliaCrawleyAustralia

Personalised recommendations