Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Xylomaticin and Gonionenin, Cytotoxic Annonaceous Acetogenins from the Seeds of Annona cherimolia

  • Kim, Dal-Hwan (Testing and Analysis Team, Korea Food and Drug Administration) ;
  • Fang, Zhe (College of Pharmacy, Catholic University of Daegu) ;
  • Lee, Young-Eun (College of Pharmacy, Catholic University of Daegu) ;
  • Woo, Mi-Hee (College of Pharmacy, Catholic University of Daegu)
  • Published : 2007.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

Further bioactivity-directed fractionation of the ethanol extract of the seeds of Annona cherimolia has led to the isolation of two mono-tetrahydrofuran acetogenins, xylomaticin (1) and gonionenin (2). The structures of these compounds were characterized on the basis of chemical and spectroscopic data. Compounds 1 and 2 have a relative stereochemistry relationship of threo/trans/threo across the mono-tetrahydrofuran ring with its two flanking hydroxyls. Compounds 1 and 2 are known, but are first isolated from this plant. In brine shrimp lethality test (BST), 1 and 2 exhibited cytotoxic activity.

Keywords

References

  1. Alkofahi, A., Rupprecht, J.K. Smith, D.L., and Chang, C.J., Bioactive acetogenins from Goniothalamus giganteus (Annonaceae). Experientia 44, 83-85 (1988) https://doi.org/10.1007/BF01960258
  2. Barriga, H.G., Flora Medicinal de Colombia, Vol. 1, Botanica, Bogata, pp. 340, 1974
  3. Colman-Saizarbitoria, T., Zambrano, J., Ferrigni, N.R., Gu, Z.M., Ng, J.H., Smith, D.L., and McLaughlin. J. L., Bioactive annonaceous acetogenins from the bark of Xylopia aromatica. J. Nat. Prod. 57, 486 (1994)
  4. Fang, X.P., Rieser, M.J., Gu, Z.M., Zhao, G.X., and McLaughlin, J. L., Annonaceous acetogenins: an updated review. Phytochem. Anal. 4, 27-67 (1993) https://doi.org/10.1002/pca.2800040108
  5. Fies, R.E., 'Annonaceae', in 'Die Natürlichen Pflanzen familien', 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., Sihgh, S., Singh, M., Gupta, Y. K., and Sahai, M., Annonaceous acetogenins from the seeds of Annona squamosa, non-adjacent bistetrahydrofuranic acetogenins. Chem. Pharm. Bull. 42, 1175-1184 (1994) https://doi.org/10.1248/cpb.42.1175
  7. Gu, Z.M., Fang, X.P., Zeng, L., Song, R., Ng, J.H., Wood, K.V., Smith, D.L., and McLaughlin, J.L., Gonionenin: A new cytotoxic annonaceous acetogenin from Goniothalamus giganteus and the conversion of mono-THF acetogenins to bis-THF acetogenins. J. Org. Chem. 59, 3472-3479 (1994) https://doi.org/10.1021/jo00091a043
  8. Harmange, J.C., Figadere, B., and Cave, A., Stereocontrolled synthesis of 2,5-linked monotetrahydrofuran units of acetogenins. Tetrahedron Lett. 33, 5749-5752 (1992) https://doi.org/10.1016/0040-4039(92)89022-5
  9. Kim, D.H., Ma, E.S., Suk, K.D., Son, J.K., Lee, J.S., and Woo, M.H., Annomolin and annocherimolin, new cytotoxic Annonaceous acetogenins from Annona cherimolia seeds. J. Nat. Prod. 64, 502-506 (2001) https://doi.org/10.1021/np000335u
  10. Kim, D.H. and Woo, M.H., Corrosolin and compound-2: cytotoxic annonaceous acetogenins from the seeds of Annona cherimolia. Yakhak Hoeji 43, 584-590 (1999)
  11. Laprevote, O., Girard, C., and 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) https://doi.org/10.1016/S0040-4039(00)79142-8
  12. McLaughlin, J.L., 'Methods in Plant Biochemistry', Hostettmann, K. (Ed.), Academic Press, London, 6, 1-35, (1991)
  13. Meyer, B.N., Ferrigni, N.R., Putnam, J.E., Jacobson, L.B., Nichols, D.E., and McLaughlin, J.L., Brine shrimp: a convenient general bioassay for active plant constituent. Planta Med. 45, 31-34 (1982) https://doi.org/10.1055/s-2007-971236
  14. Ratnayake, S., Gu, Z.M., Miesbauer, L.R., Smith, L., Wood, K.V., Evert, D.R., and McLaughlin, J.L., Parvifloracin and parviflorin: cytotoxic bistetrahydrofuran acetogenins with 35 carbons from Asimina parviflora (Annonaceae). Can. J. Chem. 72, 287-293 (1994) https://doi.org/10.1139/v94-044
  15. Rupprecht, J.K., Hui, Y.H., and McLaughlin, J.L., Annonaceous acetogenins: a review. J. Nat. Prod. 53, 237-278 (1990) https://doi.org/10.1021/np50068a001
  16. Son, J.K., Kim, D.H., and Woo, M.H., Two new epimeric pairs of acetogenins bearing a carbonyl group from Annona cherimolia seeds. J. Nat. Prod. 66, 1369-1372 (2003) https://doi.org/10.1021/np0301487
  17. Woo, M.H., Kim, D.H., Fotopoulos, S.S., and McLaughlin, J.L., Annocherin and (2,4)-cis- and trans-annocherinones: monotetrahydrofuran Annonaceous acetogenins with a C-7 carbonyl group from Annona cherimolia seeds. J. Nat. Prod. 62, 1250-1255 (1999a) https://doi.org/10.1021/np990135m
  18. Woo, M.H., Chung, S.O., and Kim, D.H., cis-Annonacin and (2,4)-cisand trans-isoannonacins: cytotoxic monotetrahydrofuran Annonaceous acetogenins from the seeds of Annona cherimolia. Arch. Pharm. Res. 22, 524-528 (1999b) https://doi.org/10.1007/BF02979164