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Annonaceous Acetogenins

Potent Mitochondrial Inhibitors with Diverse Applications

  • Chapter
Phytochemistry of Medicinal Plants

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 29))

Abstract

Annonaceous acetogenins are a relatively new, but rapidly growing, class of compounds. Since the first of them, uvaricin, was reported in 1982,1 more than 160 compounds have been published. These natural products have attracted considerable interest due to their diversity of bioactivities. Most acetogenins are potently bioactive and offer exciting potential as new antitumor, immunosuppressive, pesticidal, antiprotozoal, antifeedant, anthelmintic, and antimicrobial agents.2-7 Chemically, the Annonaceous acetogenins seem to be derivatives of C32 or C34 fatty acids which are combined with a 2-propanol unit at C-2; the propanol is incorporated into a 2,4-disubstituted γ-lactone which can assume several different forms. Usually, one, two, or three tetrahydrofuran (Thf) rings exist in the middle of the long hydrocarbon chain, which often contains a number of oxygenated moieties (hydroxyls, acetoxyls, ketones, epoxides), and/or a double bond.

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References

  1. Jolad, S. D., Hoffmann, J. J., Schram, K. H., Cole, J. R. 1982. Uvaricin, a new antitumor agent from Uvaria accuminata (Annonaceae). J. Org. Chem. 47: 3151–3153.

    Article  Google Scholar 

  2. Moeschler, H. F., Pfluger, W., Wendish, D. 1986. Annonin insecticide. German Patent, No.De 3438763 Al.

    Google Scholar 

  3. Moeschler, H. F., Pfluger, W., Wendish, D. 1987. Pure annonin and a process for the preparation. U.S. Patent, No. 4,689,232.

    Google Scholar 

  4. Mikolajczak, K. L., McLaughlin, J. L., Rupprecht, J. K. 1988. Control of pests with Annonaceous acetogenins. U.S. Patent, No. 4,721,727.

    Google Scholar 

  5. Mikolajczak, K. L., McLaughlin, J. L., Rupprecht, J. K. 1989. Control of pests with Annonaceous acetogenins. U.S. Patent, No. 4,855,319.

    Google Scholar 

  6. Cave, A., Hocquemiller, R., Laprevote, O. 1989. Utilisation d’acetogenins en therapeutique en tant que substances antiparasitaires. F Patent 1048 No. 88 09 674.

    Google Scholar 

  7. Ikekawa, N., Fujimoto, Y, Ikekawa, T., Sumuralimited Co. 1991. Novel bistetrahydrofuran compounds and their preparations used as anticancer agents. Japan Patent No. He 3-41076.

    Google Scholar 

  8. Rupprecht, J. K., Hui, Y.-H., McLaughlin, J. L. 1990. Annonaceous acetogenins: A review. J. Nat. Prod. 53: 237–278.

    Article  PubMed  CAS  Google Scholar 

  9. Fang, X.-R, Rieser, M. J., Gu, Z.-M., Zhao, G.-X., McLaughlin, J. L. 1993. Annonaceous acetogenins: an updated review. Phytochem. Anal. 4: 27–67.

    Article  CAS  Google Scholar 

  10. Cave, A., Cortes, D., Figadere, B., Hocquemiller, R., Laprevote, O., Laurens, A., Leboeuf, M. 1991. Recent Advances In Phytochemistry. (Downum, K. R.; Romeo, J.; Stafford, H. A., eds). Plenum Press, New York, 27: 167–202.

    Google Scholar 

  11. Cortes, D., Figadere, R., Cave, A. 1993. Bistetrahydrofuran acetogenins from Annonaceae. Phytochemistry 32: 1467–1473.

    Article  CAS  Google Scholar 

  12. Abreo, M. J., Sneden, A. T. 1989. 4-Hydroxy-25-desoxyneorollinicin, a new bistetra-hydrofuranoid acetogenin from Rollinia papilionella. J. Nat. Prod. 52: 822–828.

    Article  PubMed  CAS  Google Scholar 

  13. Meyer, B. N., Ferrigni, N. R. Putnam, J. E. Jacobson, L. B. Nichols, D. E. McLaughlin, J. L. 1982 Planta Med. 45: 31–34.

    Article  CAS  Google Scholar 

  14. McLaughlin, J. L. 1991. Methods in Plant Biochemistry, vol. 6. (K. Hostettmann, ed.), Academic Press, London, 1991, pp. 1–33.

    Google Scholar 

  15. Fogh, J., Trempe, G. 1975. New Human Tumor Cell Lines in Human Tumor Cells, in vitro, J. Fogh, Ed., Plenum Press, New York, p. 115.

    Chapter  Google Scholar 

  16. Giard, D. J., Aronson, S. A., Todaro, G. J., Arnstein, P., Kersey, J. H., Dosik, H., Parks, W. P. 1973. J. Natl. Cancer Inst. 51: 1417–1423.

    PubMed  CAS  Google Scholar 

  17. Soule, H. D., Vazquez, J., Long, A., Albert, S., Brennan, M. 1973. J. Natl. Cancer Inst. 51: 1409–1416.

    PubMed  CAS  Google Scholar 

  18. Gromek, D., Hocquemiller, R. Cave, A. 1994. Qualitative and quantitative evaluation of Annonaceous acetogenins by high performance liquid chromatography. Phytochem. Anal. 5: 133–140.

    Article  CAS  Google Scholar 

  19. Laprevote, O., Girard, C., Das, B. C. 1992. Formation of gas-phase lithium complexes from acetogenins and their analysis by fast atom bombardment mass spectrometry. Tetrahedron Lett. 33: 5237–5240.

    Article  CAS  Google Scholar 

  20. Laprevote, O., Girard, C., Das, B. C., Laurens, A., Cave, A. 1993. Desorption of lithium complexes of acetogenins by fast atom bombardment: Application to semi-quantitative analysis of crude plant extracts. Analysis 21: 207–210.

    CAS  Google Scholar 

  21. Smith, D. L., Liu, Y M., Wood, K. V. 1991. Structure elucidation of natural products by mass spectrometry. Recent Advances in Phytochemistry. (N. H. Fischer, M. B. Isman, T. H. A. Hafford, eds.) Plenum Press, New York, vol. 25, pp. 251–269.

    Google Scholar 

  22. Laprevote, O., Das, B. C. 1994. Structural elucidation of acetogenins from Annonaceae by fast atom bombardment mass spectrometry. Tetrahedron 50: 8479–8490.

    Article  CAS  Google Scholar 

  23. Gu, Z.-M., Fang. X.-R, Zeng, L., Wood, K. V., McLaughlin, J. L. 1993. Bullacin: a new cytotoxic Annonaceous acetogenin from Annona bullata. Heterocycles 36: 2221–2228.

    Article  CAS  Google Scholar 

  24. Laprevote, O., Girard, C., Das, B. C. 1992. Location of epoxy ring in a long chain acetogenin by fast-atom bombardment and linked scan (B/E) mass spectrometry of lithiumcationized molecules. Rapid Commun. Mass Spectrom. 6: 352–355.

    Article  CAS  Google Scholar 

  25. Laprevote, O. Roblot, F., Hocquemiller, R., Cave, A., Charles, B., Tabet, J. C. 1991. Structural elucidation of five stereoisomeric acetogenins, uleicins A-E, by tandem mass spectrometry. Phytochemistry 30: 2721–2727.

    Article  CAS  Google Scholar 

  26. Laprevote, O., Roblot, F., Hocquemiller, R., Cave, A. 1990. Structural elucidation of two new acetogenins, epoxyrollins A and B, by tandem mass spectrometry. Tetrahedron Lett. 31: 2283–2286.

    Article  CAS  Google Scholar 

  27. Nonfon, M., Lieb, F., Moeschler, H., Wendisch, D. 1990. Four annonins from Annona squamosa. Phytochemistry 29: 1951–1954.

    Article  CAS  Google Scholar 

  28. Rieser, M. J. 1993. Ph.D. Thesis. Annonaceous acetogenins from the seeds of Annona muricata. Purdue University, West Lafayette, Indiana, pp. 149–155.

    Google Scholar 

  29. Hui, Y. H., Rupprecht, J. K., Anderson, J. E., Liu, Y. M., Smith, D. L., Chang, C. J., McLaughlin, J. L. 1989. Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata. J. Nat. Prod. 52: 463–477.

    Article  PubMed  CAS  Google Scholar 

  30. Gu, Z.-M., Fang, X.-P., Miesbauer, L. R.; Smith, D. L., McLaughlin, J. L. 1993. 30-, 31-, and 32-Hydroxybullatacinones: bioactive terminally hydroxylated Annonaceous acetogenins from Annona bullata. J. Nat. Prod. 56: 870–876.

    Article  PubMed  CAS  Google Scholar 

  31. Gu, Z.-M., Fang, X.-P., Hui, Y.-H., McLaughlin J. L. 1994. 10-, 12-, and 29-Hydroxybullatacinones: new cytotoxic Annonaceous acetogenins from Annona bullata Rich. (Annonaceae). Natural Toxins 2: 49–55.

    Article  PubMed  CAS  Google Scholar 

  32. Gu, Z. M., Zeng, L., McLaughlin, J. L. 1994. Five bioactive adjacent bis-Thf Annonaceous acetogenins from Annona bullata. Phytochemistry (accepted).

    Google Scholar 

  33. Gu, Z.-M., Fang, X.-P., Zeng, L., Kozlowski, J. F., McLaughlin J. L. 1994. Novel cytotoxic Annonaceous acetogenins: (2,4-cis and trans)-bulladecinones from Annona bullata (Annonaceae). Bioorg. Med. Chem. Lett. 4: 473–478.

    Article  CAS  Google Scholar 

  34. Rieser, M. J., Fang, X. P., Anderson, J. E., Miesbauer, L. R., Smith, D. L., McLaughlin, J. L. 1994. Muricatetrocins A and B and gigantetrocin B: three new cytotoxic monotetrahydrofuran-ring acetogenins from Annona muricata. Helv. Chim. Acta 76: 2433–2444.

    Article  Google Scholar 

  35. Colman-Saizarbitoria, T., Zambrano, J., Ferrigni, N. R., Gu, Z. M., Ng, J. H., Smith, D. L., McLaughlin, J. L. 1994. Bioactive Annonaceous acetogenins from the bark of Xylopia aromatica. J. Nat. Prod. 57: 486–493.

    Article  PubMed  CAS  Google Scholar 

  36. Colman-Saizarbitoria, Gu, Z. M., McLaughlin, J. L. 1994. Two new bioactive monotetrahydrofuran Annonaceous acetogenins from the bark of Xylopia aromatica. J. Nat. Prod. 57: 1661–1669.

    Article  PubMed  CAS  Google Scholar 

  37. Fang, X.-P., Anderson, J.E., Smith, D. L., Wood, K. V., McLaughlin, J. L. 1991. Giganenin, a highly potent monotetrahydrofuran acetogenin and 4-deoxygigantecin from Goniothalamus giganteus. Heterocycles 34: 1075–1082.

    Google Scholar 

  38. Gu, Z.-M., Fang, X.-P., Zeng, L., Song, R., Ng, J. H., Wood, K. V, Smith, D. L., cLaughlin, J. L. 1994. 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.

    Article  CAS  Google Scholar 

  39. Araya, H., Hara, N., Fujimoto, Y., Srivastava, A., Sahai, M. 1994. Squamosten-A, a novel mono-tetrahydrofuranic acetogenin with a double bond in the hydrocarbon chain, from Annona squamosa L. Chem. Pharm. Bull. 42: 388–391.

    Article  CAS  Google Scholar 

  40. Fang, X.-P, Rupprecht, J. K., Alkofahi, A., Hui, Y.-H., Liu, Y.-M., Smith, D. L., Wood, K.V., McLAUGHLIN, J. L. 1991. Gigantetrocin and gigantriocin: two novel bioactive Annonaceous acetogenins from Goniothalamus giganteus. Heterocycles 32: 11–17.

    Article  CAS  Google Scholar 

  41. Wu, F. E., Gu, Z. M., Zeng, L., Zhao, G. X., Zhang, Y, McLaughlin, J. L. 1994. Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata. J. Nat. Prod, (accepted).

    Google Scholar 

  42. Gu, Z.-M., Zeng, L., Fang, X.-P., COLMAN-Saizarbitoria, T., Huo, M., McLaughlin, J. L. 1994. Determining absolute configurations of stereocenters in Annonaceous acetogenins through formaldehyde acetal derivatives and Mosher ester methodology. J. Org. Chem. 59: 5162–5172.

    Article  CAS  Google Scholar 

  43. Born, L., Lieb, F., Lorentzen, J. P., MOESCHER, H., Nonfon, M., Sollner, R., Wendisch, D. 1990. The relative configuration of acetogenins isolated from Annona squamosa: annonin I (squamocin) and annonin Vi. Planta Med. 56: 312–316.

    Article  PubMed  CAS  Google Scholar 

  44. Jossang, A., Dubaele, B., Cave, A. 1990. Deux nouvelles acetogenins onotetrahy-drofuranniques cytotoxiques: l’annomonicine et la montanacine. Tetrahedron Lett. 31: 1861–1864.

    Article  CAS  Google Scholar 

  45. Hoye, T. R., Zhuang, Z. 1988. Validation of the 1H Nmr chemical shift method for determination of stereochemistry in the bis (tetrahydrofuranyl) moiety of uvaricin-related acetogenins from Annonaceae: Rolliniastatin 1 (and asimicin). J. Org. Chem. 53: 5578–5580.

    Article  CAS  Google Scholar 

  46. Hoye, T. R., Hanson, P. R. 1991. Assigning the relative stereochemistry between C(2) and C(4) of the 2-acetonyl-4-alkylbutyrolactone substructures of the appropriate Annonaceous acetogenins. J. Org. Chem. 56: 5092–5095.

    Article  CAS  Google Scholar 

  47. Rieser, M. J., Hui, Y.-H., Rupprecht, J. K., Kozlowski, J. F., Wood, K. V, McLaughlin, J. L., Hanson, P. R., Zhuang, A., Hoye, T. R. 1992. Determination of absolute configuration of stereogenic carbinol centers in Annonaceous acetogenins by 1H-and 19F-Nmr analysis of Mosher ester derivatives. J. Am. Chem. Soc. 144: 10203–10213.

    Article  Google Scholar 

  48. Fujimoto, Y., Murasaki, C., Shimada, H., Nishioka, S., Kakinuma, K., Singh, S., Singh, M., Gupta, Y K., Sahai, M. 1994. Annonaceous acetogenins from the seeds of Annona squamosa. Non-adjacent bis-tetrahydrofuranic acetogenins. Chem. Pharm. Bull. 42: 1175–1184.

    Article  CAS  Google Scholar 

  49. Gale, J. B., Yu, J. G., Hu, X. E., Khare, A., Ho, D. K., Cassady, J. M. 1993. Stereochemistry of mono-tetrahydrofuranyl moiety in cytotoxic polyketides. Part B: application of proton chemical shift patterns. Tetrahedron Lett. 34: 5851–5854.

    Article  CAS  Google Scholar 

  50. Yu, J. G., Ho, D. K., Cassady, J. M., Xu, L. Z., Chang, C. J. 1992. Cytotoxic polyketides from Annona densicoma (Annonaceae): 10,13-trans-13,14-erythro-densicomacin, 10,13-trans-13,14-threo-densicomacin, and 8-hydroxyannonacin. J. Org. Chem. 57: 6198–6202.

    Article  CAS  Google Scholar 

  51. Hishioka, S., Araya, H., Murasaki, C., Sahai, M., Fujimoto, Y. 1994. Determination of absolute stereochemistry at carbinol stereocenters of tetrahydrofuranic acetogenins by advanced Mosher method. Nat. Prod. Lett. 5: 117–121.

    Article  Google Scholar 

  52. Shimada, H., Nishioka, S. Singh, S., Sahai, M., Fujimoto, Y. 1994. Absolute stereochemistry of non-adjacent bis-tetrahydrofuranic acetogenins. Tetrahedron Lett. 35: 3961–3964.

    Article  CAS  Google Scholar 

  53. Mikolajczak, K. J., Madrigal, R. V., Rupprecht, J. K., Hui, Y H., Liu, Y M., Smith, D. L., McLaughlin, J. L. 1990. Sylvaticin: a new cytotoxic and insecticidal acetogenin from Rollinia sylvatica (Annonaceae). Experientia 46: 324–327.

    Article  PubMed  CAS  Google Scholar 

  54. Fang, X.-P, Gu, Z.-M., Rieser, M. J., Hui, Y.-H., McLaughlin, J. L. 1993 Structural revisions of some non-adjacent bis-tetrahydrofuran Annonaceous acetogenins. J. Nat. Prod. 56: 1095–1100.

    Article  PubMed  CAS  Google Scholar 

  55. Cortes, D., Myint, S. H., Dupont, B., Davoust, D. 1993. Bioactive acetogenins from seeds of Annona cherimolia. Phytochemistry 32: 1475–1482.

    Article  CAS  Google Scholar 

  56. Fujimoto, Y., Murasaki, C., Kakinuma, K., Eguchi, T., Ikekawa, N., Fu-Ruya, M., Hirayama, K., Ikekawa, T., Sahai, M, Gupta, Y K., Ray, A. B. 1990. Squamostatin-A: unprecedented bis-tetrahydrofiiran acetogenin from Annona squamosa. Tetrahedron Lett. 31: 535–538.

    Article  CAS  Google Scholar 

  57. Yu, J.-G., Luo, X.-Z., Sun, L., Liu, C.-Y., Hong, S.-L., Ma, L.B. 1993. Squamostatin-B, a new polyketide from Annona squamosa (Annonaceae). Chin. Chem. Lett. 4: 423–426.

    CAS  Google Scholar 

  58. Zhao, G.-X., Hui, Y. H., Rupprecht, J. K., McLaughlin, J. L. 1992. Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba. J. Nat. Prod. 55: 347–356.

    Article  PubMed  CAS  Google Scholar 

  59. Zhao, G.-X., Gu, Z.-M., Zeng, L., Chao, J.-F., Kozlowski, J. R, Wood, K. V., McLaughlin, J. L. 1995. The absolute configurations of trilobacin and trilobin, a novel highly potent acetogenin from the stem bark of Asiminia triloba (Annonaceae). Tetrahedron (submitted)

    Google Scholar 

  60. Rieser, M. J., Fang, X. P., Anderson, J. E., Miesbauer, L. R., Smith, D. L., McLaughlin, J. L. 1994. Erratum. Helv. Chim. Acta 77:882.

    Article  CAS  Google Scholar 

  61. Myint, S. H., Cortes, D., Laurens, A., Hocquemiller, R., Leboeuf, M., Cave, A., Cotte, J., Queros, A. M. 1991. Solamin, a cytotoxic mono-tetrahydrofuranic γ-lactone acetogenin from Annona muricata seeds. Phytochemistry 30: 3335–3338.

    Article  CAS  Google Scholar 

  62. Wu, Y.-C., Chang, F.-R., Chen, K.-S., Liang, S.-C., Lee, M.-R. 1994. Diepoxymontin, a novel acetogenin from Annona montana. Heterocycles 38: 1475–1478.

    Article  CAS  Google Scholar 

  63. Gromek, D., Figadere, B., Hocquemiller, R. Cave, A. 1993. Corepoxylone, a possible precursor of mono-tetrahydrofuran γ-lactone acetogenins: biomimetic synthesis of corossolone. Tetrahedron 49: 5247–5252.

    Article  CAS  Google Scholar 

  64. Hisham, A., Sreekala, U., Pieters, L., Bruyne, T. D., Heuvel, H. V. D., Claeys, M. 1993. Epoxymurins A and B, two biogenetic precursors of Annonaceous acetogenins from Annona muricata. Tetrahedron 31: 6913–6920.

    Article  Google Scholar 

  65. Sahpaz, S., Laurens, A., Hocquemiller, R., Cave, A. 1994. Senegalene, une nouvelle acetogenine olefinique mono-tetrahydrofuranique des graines d’Annona senegalensis. Can. J. Chem. 72: 1–4.

    Article  Google Scholar 

  66. 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., Fujimoto, Y. 1994. Annonaceous acetogenins from the seeds of Annona squamosa. Adjacent bis-tetrahy-drofuranic acetogenins. Chem. Pharm. Bull. 42: 1163–1174.

    Article  CAS  Google Scholar 

  67. Hui, Y.-H. 1991. Ph.D. Thesis. The search for bioactive constituents from Annona bullata Rich. (Annonaceae). Purdue University, West Lafayette, Indiana, pp. 136–145.

    Google Scholar 

  68. Duret, P., Laurens, A., Hocquemiller, R., Cortes, D., Cave, A. 1994. Isoacetogenins, artifacts issued from translactonization from Annonaceous acetogenins Heterocycles, 39: 741–749.

    CAS  Google Scholar 

  69. Ahammadsahib, K. I., Hollingworth, R. M., McGovren, J. P., Hui, Y.-H., McLaughlin, J. L. 1993. Mode of action of bullatacin: A potent antitumor and pesticidal Annonaceous acetogenin. Life Sciences 53: 1113–1120.

    Article  PubMed  CAS  Google Scholar 

  70. Fang, X.-P. Anderson, J. E., Smith, D. L, McLaughlin, J. L., Wood, K. V. 1992. Gigantetronenin and gigantrionenin: novel cytotoxic acetogenins from Goniothalamus giganteus. J. Nat. Prod. 55: 1655–1663.

    Article  PubMed  CAS  Google Scholar 

  71. Roblot, F., Laugel, T., Leboeuf, M., Cave, A., Laprevote, O. 1993. Two acetogenins from Annona muricata seeds. Phytochemistry 34: 281–285.

    Article  CAS  Google Scholar 

  72. Gu, Z. M., Fang, X. P., Zeng, L., McLaughlin, J. L. 1994. Goniocin from Goniothalamus giganteus: the first tri-Thf Annonaceous acetogenin. Tetrahedron Lett. 35: 5367–5368.

    Article  CAS  Google Scholar 

  73. Tam, V. T., Hieu, P. Q. C., Chappe, B., Roblot, F., Laprevote, O., Figadere, B., Cave, A. 1994. Four new acetogenins from the seeds of Annona reticulata. Nat. Prod. Lett. 4: 255–262.

    Article  Google Scholar 

  74. Sahpaz, S., Figadere, B. Saez, J., Hocquemiller, R., Cave, A., Cortes, D. 1994. Tripoxyrollin, a new epoxy acetogenin from the seeds of Rollinia membranacea. Nat. Prod. Lett. 2: 301–308.

    Article  Google Scholar 

  75. Hoye, T. R., Hanson, P. R., Kovelesky, A. C., Ocain, T. D., Zhuang, Z. P. 1991. Synthesis of (+)-(15,16,19,20,23,24)-hexepi-uvaricin: A bis (tetrahydrofuranyl) Annon-aceous acetogenin analogue. J. Am. Chem. Soc. 113: 9369–9371.

    Article  CAS  Google Scholar 

  76. Hoye, T. R., Hanson, P. R. 1993. Synthesis of (-)-bullatacin: The enantiomer of a potent, antitumor, 4-hydroxylated, Annonaceous acetogenin. Tetrahedron Lett. 34: 5043–5046.

    Article  CAS  Google Scholar 

  77. Yao, Z. J., Wu, Y. L. 1994. Total synthesis of (10, 15R, 16R, 19S, 20S, 34R)-corossoline. Tetrahedron Lett. 35: 157–160.

    Article  CAS  Google Scholar 

  78. Koert, U. 1994. Total synthesis of (+)-rolliniastatin 1. Tetrahedron Lett. 35: 2517–2520.

    Article  CAS  Google Scholar 

  79. Sinha, S. C., Keinan, E. 1993. Total synthesis of naturally occurring acetogenins: solamin and reticulatacin. J. Am. Chem. Soc. 115: 4891–4892.

    Article  CAS  Google Scholar 

  80. Tam, V. T., Chaboche, C., Figadere, B., Chappe, B., Hieu, B. C., Cave, A. 1994. First synthesis of a new acetogenin of Annonaceae, reticulatamol: activated tin hydride with enhanced reducing ability. Tetrahedron Lett. 35: 883–886.

    Article  CAS  Google Scholar 

  81. Hoye, T. R., Suhadolnik, J. C. 1986. Stereocontrolled synthesis of 2,5-linked bistetra-hydrofurans via the triepoxide cascade reaction. Tetrahedron 42: 2855–2862.

    Article  CAS  Google Scholar 

  82. Bertrand, P., Gesson, J.-P. 1992. Approach to the synthesis of Annonaceous acetogenins from D-glucose. Tetrahedron Lett. 33: 5177–5180.

    Article  CAS  Google Scholar 

  83. Harmange, J. C., Figadere, B., Cave, A. 1992. Stereocontrolled synthesis of 2,5-linked monotetrahydrofuran units of acetogenins. Tetrahedron Lett. 33: 5749–5752.

    Article  CAS  Google Scholar 

  84. Cortes, D., Myint, S. H., Harmange, J. C., Sahpaz, S., Figadere, B. 1992. Catalytic hydrogenation of Annonaceous acetogenins. Tetrahedron Lett. 33: 5225–5226.

    Article  CAS  Google Scholar 

  85. Figadere, B., Harmange, J. C., Hai, L. X., Cave, A. 1992. Synthesis of 2,33-dihy-dro-4-oxo-murisolin: conjugate addition of primary alkyl iodides to α, β-unsaturated ketones. Tetrahedron Lett. 33: 5189–5192.

    Article  CAS  Google Scholar 

  86. Jonathan, B. G., Yu, J. G., Hu, X. E., Khare, A., Ho, D. K., Cassady, J. M. 1993. Stereochemistry of mono-tetrahydrofuranyl moiety in cytotoxic polyketides. Part A: synthesis of model compounds. Tetrahedron Lett. 34: 5847–5850.

    Article  Google Scholar 

  87. Hoppe, R., Flasche, M., Scharf, H. D. 1994. An approach towards 2,5-disubstituted tetrahydrofurans of Annonaceous acetogenins. Tetrahedron Lett. 35: 2873–2876.

    Article  CAS  Google Scholar 

  88. Harmange, J. C., Figadere, B., Hocquemiller, R. 1991. Enantiospecific preparation of the lactone fragment of murisolin. Tetrahedron: Asymmetry 2: 347–350.

    Article  CAS  Google Scholar 

  89. Bertrand. P., Gesson, J.-P. 1992. Stereoselective synthesis of the trans 2,4-disubstituted butyrolactone moiety of Annonaceous acetogenins. Synlett. 889-890.

    Google Scholar 

  90. Scholz, G., Tochtermann, W. 1991. Optisch aktive γ-lactone aus cyclooctin und furan-synthese von (-)-muricatacin. Tetrahedron Lett. 32: 5535–5538.

    Article  CAS  Google Scholar 

  91. Figadere, B., Chaboche, C., Peyrat, J.-F., Cave, A. 1993. Stereocontrolled synthesis of key intermediates in the total synthesis of acetogenins of Annonaceae. Tetrahedron Lett. 34: 8093–8096.

    Article  CAS  Google Scholar 

  92. Londershausen, M., Leicht, W., Lieb, F., Moeschler, H., Weiss, H. 1991. Molecular mode of action of annonins. Pesticide Sci. 33: 427–438.

    Article  CAS  Google Scholar 

  93. Lewis, M A., Arnason, J. T., Philogene, B. J. R., Rupprecht, J. K., McLaughlin, J. L. 1993. Inhibition of respiration at site I by asimicin, an insecticidal acetogenin of the pawpaw, Asimina triloba (Annonaceae). Pesticide Biochem. Physiol. 45: 15–23.

    Article  CAS  Google Scholar 

  94. Hollingworth, R. M., Ahammadsahib, K. I., Gadelhak, G., McLaughlin, J. L. 1994. New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides. Biochem. Soc. Trans. 22: 230–233.

    PubMed  CAS  Google Scholar 

  95. Espositi, M. D., Ghelli, A., Batta, M., Cortes, D., Estornell. E. 1994. Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial Nadh dehydrogenase (complex I). Biochem. J. 301: 161–167.

    Google Scholar 

  96. Friedrich, T., Ohnishi, T., Forche, E., Kunze, B., Jansen, R., Trowitzsch, W., Hofle, G., Reichenbach, H., Weiss, H. 1994. Two binding sites for naturally occurring inhibitors in mitochondrial and bacterial Nadh: ubiquinone oxidoreductase (complex I). Biochem. Soc. Trans. 22: 226–230.

    PubMed  CAS  Google Scholar 

  97. Morre, J. D., Decabo, R., Farley, C., Oberlies, N. H., McLaughlin, J. L. 1995. 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 Sciences 56: 343–348.

    Article  PubMed  CAS  Google Scholar 

  98. Landolt, J. L., Ahammadsahib, K. I., Hollingworth, R. M., Barr, R., Crane, F. L., Buerck, N. L., McCabe, G. P., McLaughlin, J. L. 1995 Chemico-Biol. Interact, (in press).

    Google Scholar 

  99. Zhao, G.-X., Miesbauer, L. R., Smith, D. L., McLaughlin, J. L. 1994. Asimin, asiminacin and asiminecin: novel highly cytotoxic asimicin isomers from Asimina triloba. J. Med. Chem. 37: 1971–1976.

    Article  PubMed  CAS  Google Scholar 

  100. McLaughlin, J. L., Hui, Y. H. 1993. Chemotherapeutically active acetogenins. U.S. Patent, No. 5,229,419.

    Google Scholar 

  101. Holschneider, C. H., Johnson, M. T., Knox, R. M., Rezai, A., Ryan, W. J., Montz, F. J. 1994. Bullatacin-in vivo and in vitro experience in an ovarian cancer model. Cancer Chemother. Pharmacol. 34: 166–170.

    Article  PubMed  CAS  Google Scholar 

  102. Cepleanu, F., Ohtani, K., Hamburger, M., Gupta, M. P., Solis, P., Hostettmann, K. 1993. Novel acetogenins from the leaves of Annona purpurea. Helv. Chim. Acta 76: 1379–1388.

    Article  CAS  Google Scholar 

  103. Ohsawa, D., Atsuzawa, S., Mitsui, T., Yamamoto, I. 1991 Isolation and insecticidal activity of three acetogenins from seeds of pond apple, Annona glabra L. J. Pesticide Sci. 16: 93–96.

    Article  CAS  Google Scholar 

  104. Sahpaz, S., Bories, C, Loiseau, P., Cortes, D., Hocquemiller, R., Laurens, A., Cave, A. 1994. Cytotoxic and antiparasitic activity from Annona senegalensis seeds. Planta Med. 60: 538–540.

    Article  PubMed  CAS  Google Scholar 

  105. Boris, C., Loiseau, P., Cortes, D., Myint, S. H., Hocquemiller, R., Gayral, P., Cave, A., Laurens, A. 1991. Antiparasitic activity of Annona muricata and Annona cherimolia seeds. Planta Med. 57: 434–436.

    Article  Google Scholar 

  106. Weinberg, M. L. D., Pires, V., Weinberg, J., Oliveira, A., B. D. 1993. Inhibition of drug-induced contractions of guinea-pig ileum by Annona crassiflora seed extract. J. Pharm. Pharmacol. 45: 70–72.

    Article  PubMed  CAS  Google Scholar 

  107. Avalos, J., Rupprecht, J. K., McLaughlin, J. L., Rodriguez, E. 1993. Guinea pig maximization test of the bark extract from pawpaw, Asimina triloba (Annonaceae). Contact Dermatitis 29: 33–35.

    Article  PubMed  CAS  Google Scholar 

  108. Alkofahi, A.; Rupprecht, J. K.; Smith, D. L.; Chang, C.-J.; McLaughlin, J. L. 1988. Goniothalamicin and annonacin: bioactive acetogenins from Goniothalamus giganteus (Annonaceae). Experientia 44: 83–85.

    Article  PubMed  CAS  Google Scholar 

  109. Rieser, M. J., Fang, X. P., Rupprecht, J. K., HUI, Y. H., Smith, D. L., McLaughlin, J. L. Bioactive single-ring acetogenins from seed extracts of Annona muricata. Planta Med. 59: 91–92.

    Google Scholar 

  110. Chang, F. R., Wu, Y. C., Duh, C. Y., Wang, S. K. 1993. Studies on the acetogenins of Formosan Annonaceous plants, II. Cytotoxic acetogenins from Annona reticulata. J. Nat. Prod. 56: 1688–1694.

    Article  PubMed  CAS  Google Scholar 

  111. Myint, S. H., Laurens, A., Hocquemiller, R., Cave, A. 1990. Murisolin: a new cytotoxic mono-tetrahydrofuran-γ-lactone from Annona muricata. Heterocycles 31: 861–867.

    Article  CAS  Google Scholar 

  112. Cortes, D., Myint, S. H., Laurens, A., Hocquemiller, R. Leboeuf, M., Cave A. 1991. Corossolone et corossoline, deux nouvelles γ-lactones mono-tetrahydrofuraniques cytotoxiques. Can. J. Chem. 69: 8–11.

    Article  CAS  Google Scholar 

  113. Wu, Y. C., Chang, F. R., Duh, C. Y., Wang, S. K. 1992. Annoreticuin and isoannoreticuin: two new cytotoxic acetogenins from Annona reticulata. Heterocycles 34: 667–674.

    Article  CAS  Google Scholar 

  114. Li, X. H., Hui, Y. H., Rupprecht, J. K., Liu, Y M., Wood, K. V., Smith, D. L., Chang, C. J., McLaughlin, J. L. 1990. Bullatacin, bullatacinone, and squamone, a new bioactive acetogenin, from the bark of Annona squamosa. J. Nat. Prod. 53: 81–86.

    Article  PubMed  CAS  Google Scholar 

  115. Jossang, A., Dub Aele, B., Cave, A., Bartoli, M. H., Beriel, H. 1991 Annomontacin: une nouvelle acetogenine γ-lactone-monotetrahydrofurannique cytotoxique de l’Annona montana. J. Nat. Prod. 54: 967–971.

    Article  PubMed  CAS  Google Scholar 

  116. Lieb, F., Nonfon, M., Wachendorff-Neumann, U., Wendisch, D. 1990 Annonacin and annonastatin from Annona squamosa. Planta Med. 56: 317–319.

    Article  PubMed  CAS  Google Scholar 

  117. McCloud, T. G., Smith, D. L., Chang, C. J., Cassady, J. M. 1987. Annonacin, a novel, biologically active polyketide from Annona densicoma. Experientia 43: 947–949.

    Article  PubMed  CAS  Google Scholar 

  118. Zhao, G. X., Rieser, M. J., Hui, Y. H., Miesbauer, L. R., Smith, D. L., McLaughlin, J. L. 1993. Biologically active acetogenins from stem bark of Asimina triloba. Phytochemistry 33: 1065–1073.

    Article  PubMed  CAS  Google Scholar 

  119. Xu, L. Z., Chang, C. J., Yu, J. G., Cassady, J. M. 1989. Chemistry and selective cytotoxicity of annonacin-10-one, isoannonacin, and isoannonacin-10-one. Novel polyketides from Annona densicoma (Annonaceae). J. Org. Chem. 54: 5418–5421.

    Article  CAS  Google Scholar 

  120. Hisham, A., Pieters, L. A. C., Claeys, M., Esmans, E., Dommisse, R., Vlietinck, A. J. 1990. Uvariamicin-I, II and III: three novel acetogenins from Uvaria narum. Tetrahedron Lett. 31: 4649–4652.

    Article  CAS  Google Scholar 

  121. Hui, Y. H., Wood, K. V, McLaughlin, J. L. 1992. Bullatencin, 4-deoxyasimicin, and the uvariamicins: additional bioactive Annonaceous acetogenins from Annona bullata Rich. (Annonaceae). Natural Toxins 1: 4–14.

    Article  PubMed  CAS  Google Scholar 

  122. Cortes, D., Myint, S. H., Leboeuf, M., Cave A. 1991. A new type of cytotoxic acetogenins: the tetrahydrofuranic β-hydroxy methyl γ-lactones. Tetrahedron Lett. 32: 6133–6134.

    Article  CAS  Google Scholar 

  123. Saad, J. M., Hui, Y H., Rupprecht, J. K., Anderson, J. E., Kozlowski, J. F., Zhao, G. X., Wood, K. V., McLaughlin, J. L. 1991. Reticulatacin: a new bioactive acetogenin from Annona reticulata (Annonaceae). Tetrahedron 47: 2751–2756.

    Article  CAS  Google Scholar 

  124. Ratnayake, S., Gu, Z. M., Miesbauer, L. R. Smith, D. L., Wood, K. V, Evert, D. R., McLaughlin, J. L. 1994. Parvifloracin and parviflorin: cytotoxic bistetrahydrofuran acetogenins with 35 carbons from Asimina parviflora (Annonaceae). Can. J. Chem. 72: 287–293.

    Article  CAS  Google Scholar 

  125. Duret, P., Gromek, D., Hocquemiller, R., Cave., A. 1995. Isolation and structure of three new bis-tetrahydrofuranic acetogenins from the roots of Annona cherimolia. J. Nat. Prod. 58: (in press).

    Google Scholar 

  126. Hisham, A., Pieters, L. A. C., Claeys, M., Esmans, E., Dommisse, R., Vlietinck, A. J. 1991. Acetogenins from root bark of Uvaria narum. Phytochemistry 30: 2373–2377.

    Article  CAS  Google Scholar 

  127. Rios, J. L., Cortes, D., Valerde, S. 1989. Acetogenins, aporphinoids, and azaanthraquinone from Annona cherimolia seeds. Planta Med. 55: 321–323.

    Article  PubMed  CAS  Google Scholar 

  128. Rupprecht, J. K., Chang, C. J., Cassady, J. M., McLaughlin, J. L. 1986. Asimicin, a new cytotoxic and pesticidal acetogenin from the pawpaw, Asimina triloba (Annonaceae). Heterocycles 24: 1197–1201.

    Article  CAS  Google Scholar 

  129. Kawazu, K., Alcatara, J. P., Kobayashi, A. 1989. Isolation and structure of Neoannonin, a novel insecticidal compound from the seeds of Annona squamosa. Agric. Biol. Chem. 53: 2719–2722.

    Article  CAS  Google Scholar 

  130. Cortes, D., Myint, S. H., Hocquemiller, R. 1991. Molvizarin and motrilin: two novel cytotoxic bis-tetrahydrofuranic γ-lactone acetogenins from Annona cherimolia. Tetrahedron 47: 8195–8202.

    Article  CAS  Google Scholar 

  131. Gu, Z.-M., Fang, X.-P., Rieser, M. J., Hui, Y.-H., Miesbauer, L. R., Smith, D. L., Wood, K. V., McLaughlin, J. L. 1993 New cytotoxic Annonaceous acetogenins: bullatanocin and cis-and trans-bullatanocinone, from Annona bullata (Annonaceae). Tetrahedron 49: 747–754.

    Article  CAS  Google Scholar 

  132. Jolad, S. D., Hoffmann, J. J., Cole, J. R. 1985. Desacetyluvaricin from Uvaria accuminata, configuration of uvaricin at C-36. J. Nat. Prod. 48: 644–645.

    Article  PubMed  CAS  Google Scholar 

  133. Etse J. T., Waterman, P. G. 1986. Chemistry in the Annonaceae, XXII. 14-hydroxy-25-desoxyrollinicin from the stem bark of Annona reticulata. J. Nat. Prod. 49: 684–686.

    Article  CAS  Google Scholar 

  134. Pettit, G. R., Riesen, R., Leet, J. E., Polonsky, J., Smith, C. R., Schmidt, J. M., Dufresne, C., Schaufelberger, D., Moretti, C. 1989. Isolation and structure of rolliniastatin 2: a new cell growth inhibitory acetogenin from Rollinia mucosa. Heterocycles 28: 213–217.

    Article  CAS  Google Scholar 

  135. Zhao, G.-X., Ng, J. H., Kozlowzki, J. F., Smith, D. L., McLaughlin, J. L. 1994. Bullatin and bullanin: two novel, highly cytotoxic acetogenins from Asimina triloba. Heterocycles 38: 1897–1908.

    Article  CAS  Google Scholar 

  136. Fujimoto, Y., Eguchi, T., Kakinuma, K., Ikekawa, N., Sahai, M., Gupta, Y K. 1988. Squamocin, a new cytotoxic bis-tetrahydrofuran containing acetogenin from Annona squamosa. Chem. Pharm. Bull. 36: 4802–4806

    Article  PubMed  CAS  Google Scholar 

  137. Saez, J., Sahpaz, S., Villaescusa, L., Hocquemiller, R., Cave, A., Cortes, D. 1993. Rioclarine et membranacine, deux nouvelles acetogenines bis-tetrahydrofuraniques des graines de Rollinia membranacea. J. Nat. Prod. 56: 351–356.

    Article  CAS  Google Scholar 

  138. Dabrah, T. T., Sneden A. 1384. Rollinicin and isorollinicin, cytotoxic acetogenins from Rollinia papilionella. Phytochemistry 23: 2013–2016

    Article  Google Scholar 

  139. Hisham, A., Pieters, L. A. C., Claeys, M., Esmans, E., Dommisse, R., Vlietinck, A. J. 1991. Squamocin-28-one and panalicin, two acetogenins from Uvaria narum. Phytochemistry 30: 545–548.

    Article  CAS  Google Scholar 

  140. Pettit, G. R., Cragg, G. M., Polonsky, J., Herald, D. L., Goswami, A., Smith, C. R., Moretti, C., Schmidt, J. M., Weisleder, D. 1987. Isolation and structure of rolliniastatin 1 from the South American tree Rollinia mucosa. Can. J. Chem. 65: 1433–1435.

    Article  CAS  Google Scholar 

  141. Abreo, M. J., Sneden, A. T. 1989. Rollinone, a revision and extension of structure. J. Nat. Prod. 53: 935–983.

    Google Scholar 

  142. Dabrah, T. T., Sneden A. 1984. Rollinone, a new cytotoxic acetogenin from Rollinia papilionella. J. Nat. Prod. 47: 652–657.

    Article  PubMed  CAS  Google Scholar 

  143. Alkofahi, A., Rupprecht, J. K., Liu, Y.-M., Chang, C.-J., Smith, D. L., McLaughlin, J. L. 1990. Gigantecin: a novel antimitotic and cytotoxic acetogenin, with nonadjacent tetrahydrofuran rings, from Goniothalamus giganteus (Annonaceae). Experientia 46: 539–541.

    Article  PubMed  CAS  Google Scholar 

  144. Hui, Y. H., Rupprecht, J. K., Liu, Y.M., Anderson, J. E., Smith, D. L., Chang, C. J., McLaughlin, J. L. 1989. Bullatalicin, a novel bioactive acetogenin from Annona bullata (Annonaceae). Tetrahedron 45: 6941–6948.

    Article  CAS  Google Scholar 

  145. Hui, Y. H., Rupprecht, J. K., Anderson, J. E., Wood, K. V, McLaughlin, J. L. 1991. Bullatalicinone, a new potent bioactive acetogenin, and squamocin from Annona bullata (Annonaceae). Phytotherapy Res. 5: 124–129.

    Article  CAS  Google Scholar 

  146. Cortes, D., Rios, J. L., Villar, A., Valverde, S. 1984. Cherimoline et dihydro-cherimoline: deux nouvelles γ-lactones bis-tetrahydrofuranniques possédant une activite antimicrobienne. Tetrahedron Lett. 25: 3199–3202.

    Article  CAS  Google Scholar 

  147. Gu, Z. M., Zeng, L., McLaughlin, J. L. 1995. Isolation and structural elucidation of bioactive C-12, 15-cis-non-adjacent bis-THF Annonaceous acetogenins. Heterocycles (accepted).

    Google Scholar 

  148. Fang, X.-P., Rong, S., Gu, Z.-M., Rieser, M. J., Miesbauer, L. R., Smith, D. L., McLaughlin, J. L. 1993. Anew type of cytotoxic Annonaceous acetogenin: giganin from Goniothalamus giganteus. Bioorg. Med. Chem. Lett. 3: 1153–1156.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana, 47907, USA

    Zhe-Ming Gu, Geng-Xian Zhao, Nicholas H. Oberlies, Lu Zeng & Jerry L. McLaughlin

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  1. Zhe-Ming Gu
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  2. Geng-Xian Zhao
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  3. Nicholas H. Oberlies
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  4. Lu Zeng
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  1. Université d’ Ottawa, Ottawa, Ontario, Canada

    John T. Arnason

  2. Universidad Nacional Autónoma de México, Coyoacán, México

    Rachel Mata

  3. University of South Florida, Tampa, Florida, USA

    John T. Romeo

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Gu, ZM., Zhao, GX., Oberlies, N.H., Zeng, L., McLaughlin, J.L. (1995). Annonaceous Acetogenins. In: Arnason, J.T., Mata, R., Romeo, J.T. (eds) Phytochemistry of Medicinal Plants. Recent Advances in Phytochemistry, vol 29. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1778-2_11

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