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Annomocherin, Annonacin and Annomontacin: a novel and two known Bioactive mono-tetrahydrofuran annonaceous acetogenins fromAnnona cherimolia seeds

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  • Medicinal Chemistry & Natural Products
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Abstract

A novel and two known bioactive mono-tetrahydrofuran (THF) annonaceous acetogenins, annomocherin (1), annonacin (2) and annomontacin (3), have been isolated from the fractionated ethanolic extracts of the seeds ofAnnona cherimolia, guided by the brine shrimp lethality test (BST). Their structures were elucidated on the basis of spectroscopic and chemical methods. All compounds have a relative stereochemistry ofthreo/trans/threo for the mono-THF ring with two flanking hydroxyls. Compound1 has a double bond at C-23/ 24 of aliphatic chain. Compound1 was isolated from natural sources for the first time, and was named annomocherin. Two known Compounds2 and3 which have never been isolated from this species before, were obtained. Compound1 exhibited potent and selective cytotoxicities against the breast carcinoma (MCF-7) and kidney carcinoma (A-498) cell lines with 100 to 1,000 times the potency of adriamycin. In brine shrimp lethality test (BST),1–3 exhibited cytotoxicity.

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References

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

    Article  PubMed  CAS  Google Scholar 

  • Alkofahi, A., Rupprecht, J. K., Smith, D. L., Chang, C. J., and McLaughlin, J. L., Coniothalamicin and annonacin: Bioactive acetogenins fromGoniothalamus giganteus (Annonaceae).Experientia, 44, 83–85 (1988).

    Article  PubMed  CAS  Google Scholar 

  • Araya, H., Hara, N., Fujimoto, Y., Srivastava, A., and Sahai, M., Squamosten-A, a novel mono-tetrahydrofu- ranic acetogenin with a double bond in the hydrocarbon chain, fromAnnona squamosa L.Chem. Pharm. Bull., 42, 388–391 (1994).

    CAS  Google Scholar 

  • Barriga, H. C.Flora Medicinal de Colombia. Vol. 1, Botánica, Bogatá, p. 340, 1974.

    Google Scholar 

  • Born, L., Lieb, F., Moescher, J. P., Nonfon, H. F., Soller, R., and Wendish, D. The relative configuration of acetogenins isolated fromAnnona squamosa: annonin I (squamocin) and annonin.Planta Med., 56, 312–316 (1990).

    Article  PubMed  CAS  Google Scholar 

  • 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 ofXylopia aromatica.J. Nat. Prod., 57, 486–493 (1994).

    Article  PubMed  CAS  Google Scholar 

  • Colman-Saizarbitoria, T., Johnson, H. A., Alali, F. Q., Hopp, D. C. Rogers, L. L., and McLaughlin, J. L., Annojahnin formAnnona jahnii: A possible precursor of mono-THF acetogenins.Phytochemistry, 49, 1609–1616 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Corters, D. Myint, S. H., Laurens, A., Hocquemiller, R. Leboeuf, M., and Cave A., Corossolone et corossoline, deux nouvelles γ-lactone fromAnnona muricata.Heterocycles, 31, 861–867 (1991).

    Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Fies, R. E., “Annonaceae”, in “Die Natülichen Pflanzenfamilien”, Engler, A., Prantl, K. (Eds.) 2nded., Dunker and Humbolt, Berlin, Vol. 17, 1959.

    Google Scholar 

  • Fogh, J. and Trempe, G.,New human tumor cell lines In human tumor cells; Fogh, J., Ed.; Plenum Press: New York, pp 115–119 (1973).

    Google Scholar 

  • Giard, D. L., Aronson, S. A., Todaro, G. J., Arnstein, P., Kersey, J. H., Dosik, H., and Parks, W. P., In vitro cultivation of human tumors: establishment of cell lines derived from a series of solid tumors.J. Natl. Cancer Inst. 51, 1417–1423 (1973).

    PubMed  CAS  Google Scholar 

  • Gu. Z. M., Zeng, L., and Fang, X. P., Colman-Saizarbitoria, T. Huo, M., McLaughlin, J. L., Determining absolute configurations of stereocenters in annonaceous acetogenin through formaldehyde acetal derivatives and Mosher ester methodology.J. Org. Chem., 59, 5162–5172 (1994a).

    Article  CAS  Google Scholar 

  • Gu. Z. M., Fang, X. P., Zeng, L., Song, R., Ng, J. H., and Wood, K. V., Gonionenin: a new cytotoxic annonaceous acetogenin fromGoniothalamus giganteus and the conversion of mono-THF acetogenins to bis-THF acetogenins.J. Org. Chem. 59, 3472–3479 (1994b).

    Article  CAS  Google Scholar 

  • Harmange, J. C., Figadere, B., and Cave, A., Stereo-controlled synthesis of 2,5-linked monotetrahydrofuran units of acetogenins.Tetrahedron Lett. 33, 5749–5752 (1992).

    Article  CAS  Google Scholar 

  • Hopp, D. C., Zeng, L., Gu, Z. M., Kozlowski, J. F., and McLaughlin, J. L., Novel mono-tetrahydrofuran ring acetogenins, from the barkof Annona squamosa, showing cytotoxic selectivities for the human pancreatic carcinoma cell line, PACA-2.J. Nat. Prod., 60, 581–585 (1997).

    Article  PubMed  CAS  Google Scholar 

  • Hoye, T. R., Hanson, P. R., Hasenwinkel, L. E., Ranirez, E. A., and Zhuang, Z., Stereostructural studies on the 4-hydroxylated annonaceous acetogenins; Synthesis of model butenolides of known relative and absolute configuration involving an intriguing translactonization reaction.Tetrahedron Lett., 35, 8525–8528 (1994a).

    Article  CAS  Google Scholar 

  • Hoye, T. R., Hanson, P. R., Hasenwinkel, L. E., Ranirez, E. A., and Zhuang, Z., Stereostructural studies on the 4-hydroxylated annonaceous acetogenins; A novel use of mosher ester data for determining relative configuration [between C(4) and C(36)].Tetrahedron Lett., 35, 8529–8532 (1994b).

    Article  CAS  Google Scholar 

  • Joldad, S. D., Hoffmann, J. J. Cole, J. R., Barry, C. E., Bates, R. B., Linz, G. S., and Konig, W. A., Uvaricin, a new antitumor agent fromUvaria accuminata (Annonaceae).J. Nat. Prod., 48, 644–645 (1985).

    Article  Google Scholar 

  • Jossang, A., Dubaele, B., and Cave, A., Deux nouvelles acetogenines monotetrahydrofuraniques cytotoxiques: 1′annonacine et la montanacine.Tetrahedron Lett., 31, 1861 (1990).

    Article  CAS  Google Scholar 

  • Jossang, A., Dubaele, B., Cave, A., Bartoli, M. H., and Beriel, H., Annomontacin: une nouvelle acetogenine γ-lactone-monotetrahydrofuranique cytotoxique de 1′Annona montana.J. Nat. Prod., 54, 967–971 (1991).

    Article  PubMed  CAS  Google Scholar 

  • Kaighn, M. E., Narayan, K. S., Ohnuki, Y., Lechner, J. F., and Jones, L. W., Establishment and characterization of a human prostatic carcinoma cell line (PC-3).Invest. Urol., 17, 16–23 (1979).

    PubMed  CAS  Google Scholar 

  • Kim, D. H. and Woo, M. H., Corrosolin and compound- 2: Cytotoxic annonaceous acetogenins from the seeds ofAnnona cherimolia.Yakhak Hoeji, 43, 584–590 (1999).

    CAS  Google Scholar 

  • 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 fromAnnona cherimolia Seeds.J. Nat. Prod. 64, 502–506 (2001).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

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

    Google Scholar 

  • 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 constituents.Planta Med., 45, 31–34 (1982).

    Article  CAS  Google Scholar 

  • Morre, J. D., Decabo, R, D., Farley, C., Oberlies, N. H., and 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).

    PubMed  CAS  Google Scholar 

  • Mosher, H. S., and Dale, J. A. Nuclear magnetic resonance enantiomer reagents. Configurational correlationsvia nuclear magnetic resonance chemical shifts of diastereomeric mandelate,O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters.J. Am. Chem. Soc., 95, 512–519 (1973).

    Article  Google Scholar 

  • Rieser, M. J., Hui, Y. H., Rupprecht, J. K., Kozlowshi, J. F., Wood, K. V., McLaughlin, J. L., Hanson, P. R., Zhuang, A., and Hoye, T. R., Determination of absolute configuration of sterogenic carbinol centers in annonaceous acetogenins by1H- and19F-NMR analysis of mosher ester derivatives.J. Am. Chem. Soc., 144, 10203–10213 (1992).

    Article  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  • Sahai, M., Singh, S., Singh, M., Gupta, Y. K., Akashi, S., Yuji, R., Hirayama, K., Asaki, H., Araya, H., Hara, N., Eguchi, T., Kakinuma, K., and Fujimoto, Y., Annonaceous acetogenins from the seeds ofAnnona squamosa. Adjacent bis-tetrahydrofuranic acetogenins.Chem. Pharm. Bull., 42, 1163–1174 (1994).

    CAS  Google Scholar 

  • Soule, H. D., Vazquez, J., Long, A., Albert, S., and Brennam, M., A human cell line from a pleural effusion derived from a breast carcinoma.J. Natl. Cancer Inst, 51, 1409–1416. (1973).

    PubMed  CAS  Google Scholar 

  • Woo, M. H., Zeng, L., and McLaughlin, J. L., Asitribin and asiminenins A and B, novel bioactive Annonaceous acetogneins from the seeds ofAsimina triloba.Heterocycles, 41, 1731–1742 (1995).

    Article  CAS  Google Scholar 

  • Woo, M. H., Kim, D. H., Fotopoulos, S. S., and McLaughlin, J. L., Annocherin and (2, 4)-cis-andtrans-annocherinones: monotetrahydrofuran Annonaceous aceto-genins with a C-7 carbonyl group fromAnnona cherimolia seeds.J. Nat. Prod., 62, 1250–1255 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Woo, M. H., Chung, S. O., and Kim, D. H.,cis-Annonacin and (2,4)-cis- andtrans-isoannonacins: cytotoxic monotetrahydrofuran annonaceous acetogenins from the seeds ofAnnona cherimolia.Arch. Pharm. Res., 22, 524–528 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Yunis, A. A., Arimura, G. K., and Russin, D., Human pancreatic carcinoma (MIA PaCa-2) in continuing culture: sensitivity to asparaginase.Int. J. Cancer, 19, 128–135 (1977).

    Article  PubMed  CAS  Google Scholar 

  • Zeng, L., Ye, Q., Oberlies, N. H., Shi, G., Gu, Z. -M., He, K., and McLaughlin, J. L., Recent Advances in Annonaceous acetogenins.Nat. Prod. Rep., 13, 275–306 (1996).

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Pharmacy, College of Pharmacy, Catholic University of Daegu, 712-702, Gyeongsan, Korea

    Dal Hwan Kim & Mi Hee Woo

  2. Department of Pharmacy, College of Pharmacy, Yeungnam University, 712-749, Gyeongsan, Korea

    Jong Keun Son

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  1. Dal Hwan Kim
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  2. Jong Keun Son
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Correspondence to Mi Hee Woo.

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Kim, D.H., Son, J.K. & Woo, M.H. Annomocherin, Annonacin and Annomontacin: a novel and two known Bioactive mono-tetrahydrofuran annonaceous acetogenins fromAnnona cherimolia seeds. Arch Pharm Res 24, 300–306 (2001). https://doi.org/10.1007/BF02975096

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  • DOI: https://doi.org/10.1007/BF02975096

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