Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

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

  • 101 Accesses

  • 7 Citations

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).

This is a preview of subscription content, log in to check access.

References

  1. Mali, F., Liu, X.-X., McLaughlin, J. L., Annonaceous acetogenins: Recent progress.J. Nat. Prod., 62, 504–540 (1999).

  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).

  3. Barriga, H. G.,Flora Medicinal de Colombia. Vol. 1, Botánica, Bogatá, p. 340, (1974).

  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).

  5. Fies, R. E., ⇌Annonaceae”, in “Die Natürlichen Pflanzenfamilien”, Engler, A., Prantl, K. (Eds.) 2nd ed., Dunker and Humbolt, Berlin, Vol. 17, 1959.

  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).

  7. Harmange, J. C., Figadere, B., Cavé, A., Stereocontrolled synthesis of 2,5-linked monotetrahydrofuran units of acetogenins.Tetrahedron Lett. 33, 5749–5752 (1992).

  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).

  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).

  10. McLaughlin, J. L., “Methods in Plant Biochemistry”, Hostettmann, K. (Ed.), Academic Press, London, Vol. 6, pp. 1–35, (1991).

  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).

  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).

  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).

  14. Rupprecht, J. K., Hui, Y.-H., McLaughlin, J. L., Annonaceous acetogenins: a review.J. Nat. Prod. 53, 237–278 (1990).

  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).

  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).

  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).

Download references

Author information

Correspondence to Mi-Hee Woo.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Woo, M., Chung, S. & Kim, D. cis-Annonacin and (2,4)-cis-andtrans-isoannonacins: Cytotoxic monotetrahydrofuran annonaceous acetogenins from the seeds ofAnnona cherimolia . Arch Pharm Res 22, 524–528 (1999). https://doi.org/10.1007/BF02979164

Download citation

Key words

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