Advertisement

Archives of Pharmacal Research

, Volume 22, Issue 5, pp 524–528 | Cite as

cis-Annonacin and (2,4)-cis-andtrans-isoannonacins: Cytotoxic monotetrahydrofuran annonaceous acetogenins from the seeds ofAnnona cherimolia

  • Mi-Hee Woo
  • Soon-Ok Chung
  • Dal-Hwan Kim
Research Articles Natural Products

Abstract

cis-Annonacin (1) and the mixture of (2,4)-cis-andtrans-isoannonacins (2 and3), three known mono-tetrahydrofuran annonaceous acetogenins, have been isolated from the seeds ofAnnona cherimolia by the use of the brine shrimp lethality test (BST) for bioactivity directed fractionation. Their structures were elucidated based on spectroscopic and chemical methods.1 showed potent cytotoxicities in the brine shrimp lethality test (BST) and among six human solid tumor cell lines with notable selectivity for the pancreatic cell line (PaCa-2) at about 1,000 times the potency of adriamycin. The mixture of2 and3 is over 10,000 times cytotoxic as adriamycin in the pancreatic cell line (PaCa-2). All of the compounds are about 10 to 100 times as cytotoxic as adriamycin in the prostate cell line (PC-3).

Key words

Annonaceous acetogenins Annona cherimolia cis-Annonacin (2,4)-cis- andtrans-Isoannonacins Cytotoxicities 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Mali, F., Liu, X.-X., McLaughlin, J. L., Annonaceous acetogenins: Recent progress.J. Nat. Prod., 62, 504–540 (1999).CrossRefGoogle Scholar
  2. Alkofahi, A., Rupprecht, J. K., Smith, D. L., Chang, C.-J., McLaughlin, J. L., Coniothalamicin and annonacin: Bioactive acetogenins fromGoniothalamus giganteus (Annonaceae).Experientia, 44, 83–85 (1988).PubMedCrossRefGoogle Scholar
  3. Barriga, H. G.,Flora Medicinal de Colombia. Vol. 1, Botánica, Bogatá, p. 340, (1974).Google Scholar
  4. Fang, X.-P., Rieser, M. J., Gu, Z.-M., Zhao, G.-X., McLaughlin, J. L., Annonaceous acetogenins: an updated review.Phytochem. Anal., 4, 27–67 (1993).CrossRefGoogle Scholar
  5. Fies, R. E., ⇌Annonaceae”, in “Die Natürlichen Pflanzenfamilien”, Engler, A., Prantl, K. (Eds.) 2nd ed., Dunker and Humbolt, Berlin, Vol. 17, 1959.Google Scholar
  6. Fujimoto, Y., Murasaki, C., Shimada, H., Nishioka, S., Kakinuma, K., Singh, S., Singh, M., Gupta, Y.K., Sahai, M., Annonaceous acetogenins from the seeds ofAnnona squamosa, non-adjacent bis-tetrahydrofuranic acetogenins.Chem. Pharm. Bull., 42, 1175–1184 (1994).Google Scholar
  7. Harmange, J. C., Figadere, B., Cavé, A., Stereocontrolled synthesis of 2,5-linked monotetrahydrofuran units of acetogenins.Tetrahedron Lett. 33, 5749–5752 (1992).CrossRefGoogle Scholar
  8. Jossang, A., Dubaele, B., Cavé, A., Bartoli, M. H., Beriel, H., Annomontacin: une nouvelle acetogenines γ-lactone-monotetrahydrofurannique cytotoxique de I'Annona montana.J. Nat. Prod., 54, 967–971 (1991).PubMedCrossRefGoogle Scholar
  9. Laprevote, O., Girard, C., Das, B. C., Formation of gas-phase lithium complexes from acetogenins and their analysis by fast atom bombardment mass spectrometry.Tetrahedron Lett., 33, 5237–5240 (1992).CrossRefGoogle Scholar
  10. McLaughlin, J. L., “Methods in Plant Biochemistry”, Hostettmann, K. (Ed.), Academic Press, London, Vol. 6, pp. 1–35, (1991).Google Scholar
  11. Meyer, B. N., Ferrigni, N. R., Putnam, J. E., Jacobson, L. B., Nichols, D. E., McLaughlin, J. L., Brine shrimp: a convenient general bioassay for active plant constituents.Planta Med., 45, 31–34 (1982).CrossRefGoogle Scholar
  12. Morre, J. D., Decabo, R. D., Farley, C., Oberlies, N. H., McLaughlin, J. L., Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HELA and HL-60, but not liver, plasma membranes,Life Sci., 56, 343–348 (1995).PubMedGoogle Scholar
  13. Rieser, M. J., Cu, Z.-M., Fang, X.-P., Zeng, L., Wood, K. V., McLaughlin, J. L., Five novel mono-tetrahydrofuran ring acetogenins from the seeds ofAnnona muricata, J. Nat. Prod., 59, 100–108 (1996).PubMedCrossRefGoogle Scholar
  14. Rupprecht, J. K., Hui, Y.-H., McLaughlin, J. L., Annonaceous acetogenins: a review.J. Nat. Prod. 53, 237–278 (1990).PubMedCrossRefGoogle Scholar
  15. Woo, M. H., Kim, D. H., Fotopoulos, S. S., McLaughlin, J. L., Annocherin and (2, 4)-cis-andtrans-annocherinones: monotetrahydrofuran Annonaceous acetogenins with a C-7 carbonyl group fromAnnona cherimolia seeds.J. Nat. Prod., accepted (1999).Google Scholar
  16. Xu, L. Z., Chang, C. J., Yu, J. G., Cassady, J. M., Chemistry and selective cytotoxicity of annonacin-10-one, isoannonacin, and isoannonacin-10-one. Novel polyketides fromAnnona densicoma (Annonaceae).J. Org. Chem., 54, 5418–5421 (1989).CrossRefGoogle Scholar
  17. Zeng, L., Ye, Q., Oberlies, N. H., Shi, G., Gu, Z.-M., He, K., McLaughlin, J. L., Recent Advances in Annonaceous acetogenins.Nat. Prod. Rep., 13, 275–306 (1996).PubMedCrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 1999

Authors and Affiliations

  1. 1.Department of Pharmacy, College of PharmacyCatholic University of Taegu-HyosungKyongsanKorea

Personalised recommendations