Bioactive annonaceous acetogenins

Studies in Natural Products Chemistry

Volumn 41, Issue , 2014, Pages 95-117

  Smith, Robert E ^a,b   Tran, Kevin ^a   Richards, Kristy M ^a  

^a CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^b PARK UNIVERSITY   (United States)

Author keywords

Acetogenin; Annonacin; Cancer; Graviola; Parkinsonism; Pawpaw; Squamocin

Indexed keywords

EID: 84892430411     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-444-63294-4.00004-8     Document Type: Chapter

References (94)

1. F.Q. Alali, X.X. Liu, and J.L. McLaughlin J. Nat. Prod. 62 1999 504 540
2. G.R. Pettit et al. J. Nat. Prod. 71 2008 130 133
3. M. Ojika, T. Nemoto, and K. Yamada Tetrahedron Lett. 34 1993 3461 3462
4. Y. Kashman, I. Neeman, and A. Lifshitz Tetrahedron 25 1969 4617 4631
5. C. Rodriguez-Saona, and J.T. Trumble Curr. Org. Chem. 4 2000 1249 1260
6. C. Silva-Platas et al. J. Bioenerg. Biomembr. 44 2012 461 471
7. N. Kojima, and T. Tanaka Molecules 14 2009 3621 3661
8. Y. Chen et al. J. Ethnopharmacol. 142 2012 462 466
9. M. Höllerhage et al. Exp. Neurol. 220 2009 133 142
10. K.W. Pomper, J.D. Lowe, S.B. Crabtree, and W. Keller J. Agric. Food Chem. 57 2009 8339 8343
11. A. Grzybowski et al. Braz. J. Pharmacog. 22 2012 549 557
12. S. Hamizah, A.H. Roslida, O. Fezah, K.L. Tan, Y.S. Tor, and C.I. Tan Asian Pac. J. Cancer Prev. 13 2012 2533 2539
13. Y. Chen et al. Bioorg. Med. Chem. Lett. 22 2012 2217 2219
14. F.K.N. Arthur, E. Woode, E.O. Terlabi, and C.J. Larbie Nat. Pharm. 3 2012 25 30
15. A.R. González-Esquinca et al. Interciencia 37 2012 284 289
16. J.B. Arun, K. Venkatesh, P. Chakrapani, and A.R. Rani Int. J. Phytomed. 3 2011 439 441
17. Y. Dai et al. J. Nat. Prod. 75 2012 479 483
18. C.P. Foong, and R.A. Hamid Rev. Bras. Farmacog. 22 2012 1301 1307
19. C.-C. Liaw, T.-Y. Wu, F.-R. Chang, and Y.-C. Wu Planta Med. 76 2010 1390 1404
20. Y. Chen, J.-W. Chen, Y. Wang, S.-S. Xu, and X. Li Food Chem. 135 2012 960 966
21. Y.-J. Dang, H.-Z. Feng, L. Zhang, C.-H. Hu, and C.-Y. Zhu Food Chem. 2012 2012 1 9
22. J.L. McLaughlin, G.B. Benson, J.W. Forsythe, A Novel Mechanism for the Control of Clinical Cancer: Inhibition of the Production of ATP with a Standardized Extract of Paw Paw (Asiniina triloba), Annonaceae, http://www.pawpawresearch.com/pawpaw-trials1.pdf (accessed July 30, 2012).
23. X.-H. Li et al. J. Nat. Prod. 53 1990 81 86
24. D. Caparros-Lefebvre, and A. Elbaz Lancet 354 1999 281 285
25. M. Escobar-Khondiker et al. J. Neurosci. 27 2007 7827 7837
26. A. Lannuzel Brain 130 2007 816 827
27. A. Lannuzel, M. Ruberg, and P.P. Michel Movement Disorders 23 2008 2122 2128
28. L.F. Potts et al. NeuroToxicology 33 2012 53 58
29. P. Champy et al. J. Neurochem. 88 2004 63 69
30. H. Makabe, H. Konno, and H. Miyoshi Curr. Drug Discov. Technol. 5 2008 213 229
31. M. Abe et al. Biochemistry 47 2008 6260 6266
32. C. Mao, B. Han, L.-S. Wang, and Z.-J. Yao Med. Chem. Commun. 2 2011 918 922
33. Q. Xiao et al. J. Med. Chem. 54 2011 525 533
34. N.H. Oberlies, C.-J. Chang, and J.L. McLaughlin J. Med. Chem. 40 1997 2102 2106
35. H. Fujioka et al. Org. Lett. 14 2012 1054 1057
36. L.W. Chatrou et al. Bot. J. Linn. Soc. 169 2012 5 40
37. M.C. Zafra-Polo, M.C. González, E. Estornell, S. Shapaz, and D. Cortes Phytochemistry 42 1996 253 271
38. J. Kim, and E.J. Park Curr. Med. Chem. Anticancer Agents 2 2002 485 537
39. P. Champy et al. Movement Disorders 20 2005 1629 1633
40. A. Sinz, R. Matusch, T. Kämpchen, W. Fiedler, J. Schmidt, S. Wangcharoentrakul, S. Chaichana, and V. Reutrakul Helv. Chim. Acta 81 1998 1608 161615
41. N. Badrie, and A.G. Schauss R.R. Watson, V.R. Preddy, Bioactive Foods in Promoting Health: Fruits and Vegetables 2009 Academic Press Oxford 621 643
42. J.L. McLaughlin J. Nat. Prod. 71 2008 1311 1321
43. A. Février et al. Planta Med. 65 1999 47 49
44. Z.-M. Gu et al. Phytochem. Anal. 10 1999 32 38
45. S. Mohanty et al. Nat. Prod. Commun. 3 2008 31 33
46. H. Yang, X. Li, Y. Tang, N. Zhang, J. Chen, and B. Cai J. Pharm. Biomed. Anal. 49 2009 140 144
47. T. Gallardo et al. Phytochemistry 47 1998 811 816
48. D.C. Hopp, L. Zeng, Z.-M. Gu, and J.L. McLaughlin J. Nat. Prod. 59 1996 97 99
49. T. Colman-Saizarbitoria et al. J. Nat. Prod. 57 1994 486 493
50. A. Melot, D. Fall, C. Gleye, and P. Champy Molecules 14 2009 4387 4395
51. J. Allegrand et al. Rapid Commun. Mass Spectrom. 24 2010 3602 3608
52. A. Makarov et al. Anal. Chem. 78 2006 2113 2120
53. P. Champy, V. Guérineau, and O. Laprévote Molecules 14 2009 5235 5246
54. R.E. Smith Medicinal Chemistry - Fusion of Traditional and Western Medicine 2013 Bentham Science UAE 188 238
55. D.H. Kim, J.K. Son, and M.H. Woo Arch. Pharm. Res. 24 2001 300 306
56. B.E. Richter et al. Anal. Chem. 68 1996 1033 1039
57. V. Piccialli et al. J. Chem. Crystallogr. 42 2012 360 365 Conformation by NMR
58. J.-G. Yu, X.E. Hu, D.K. Ho, M.F. Bean, R.E. Stephens, and J.M. Cassady J. Org. Chem. 59 1994 1598 1599
59. L. Taylor, Technical Data Report for Graviola Annona muricata, Reprinted from Herbal Secrets of the Rainforest, second ed., Sage Press, Austin, TX, 2002, http://com-www.com/killcancernow.com/GRAVIOLA.pdf (accessed August 23, 2012).
60. Y.N. Gholse, and S.R. Yadav Int. J. Pharm. Technol. 4 2012 1950 1973
61. N.H. Oberlies, V.L. Croy, M.L. Harrison, and J.L. McLaughlin Cancer Lett. 115 1997 73 79
62. N.H. Oberlies, C.J. Chang, and J.L. McLaughlin J. Med. Chem. 20 1997 2102 2106
63. L. Feng et al. J. Nat. Prod. 59 1996 1035 1042
64. M.J. Rieser et al. J. Nat. Prod. 59 1996 100 108
65. F.E. Wu et al. J. Nat. Prod. 58 1995 1430 1437
66. F.E. Wu et al. J. Nat. Prod. 58 1995 902 908
67. F.E. Wu et al. J. Nat. Prod. 58 1995 830 836
68. M.J. Rieser et al. Planta Med. 59 1993 91 92
69. M.J. Rieser et al. Tetrahedron Lett. 32 1991 1137 1140
70. G.S. Kim et al. Phytochemistry 49 1998 565 571
71. P. Padma, N.P. Pramod, S.P. Thyagarajan, and R.L. Khosa J. Ethnopharmacol. 61 1998 81 83
72. C. Gleye, P. Duret, A. Laurens, R. Hocquemiller, and A. Cavé J. Nat. Prod. 61 1998 576 579
73. G.S. Kim et al. J. Nat. Prod. 61 1998 432 436
74. C.C. Liaw et al. J. Nat. Prod. 65 2002 470 475
75. F.R. Chang et al. J. Nat. Prod. 64 2001 925 931
76. M. Abe et al. Biochemistry 44 2005 14898 14906
77. S. Derbré et al. Bioorg. Med. Chem. Lett. 18 2008 5741 5744
78. C.-C. Lee, Y.-H. Lin, W.-H. Chang, P.-C. Lin, Y.-C. Wu, and J.-G. Chang BMC Cancer 11 2011 58
79. D. Alfonso, H.A. Johnson, T. Colman-Saizarbitoria, C.P. Presley, G.P. McCabe, and J.L. McLaughlin Nat. Toxins 4 1996 181 188
80. C.-C. Liaw et al. Angew. Chem. Int. Ed. 50 2011 7885 7891
81. M. Sharpe, S.E. Easthope, G.M. Keating, and H.M. Lamb Drugs 62 2002 2089 2126
82. B. Ifeoma, I.B. Enweani, J. Obroku, T. Enahoro, and C. Omoifo Food Agric. Environ. 2 2004 39 43
83. M.M. Lustosa, C.B. Barroso, T.F. Varêda, and N.P. Carvalho Nat. Prod. J. 2 2012 161 163
84. G.N.L. do Nascimento et al. Braz. J. Pharmacog. 22 2012 580 586
85. H. Shimada, J.B. Grutzner, J.F. Kozlowski, and J.L. McLaughlin Biochemistry 37 1998 854 866
86. H. Shimada, F. Kozlowski, and J.L. McLaughlin Pharmacol. Res. 37 1998 357 364
87. H. Miyoshi et al. Biochim. Biophys. Acta 1365 1998 443 452
88. T. Friedrich et al. Eur. J. Biochem. 219 1994 691 698
89. M. Degli Esposti, A. Ghelli, M. Ratta, D. Cortes, and E. Estornell Biochem. J. 301 1994 161 167
90. J.A. Bombasaro et al. J. Mol. Str. 1003 2012 87 91
91. A. Bermejo, B. Figadère, M.-C. Zafra-Polo, I. Barrachina, E. Estornell, and D. Cortes Nat. Prod. Rep. 22 2005 269 303
92. N. Ichimaru et al. Biochemistry 44 2005 816 825
93. Y.-Q. Liu et al. PLoS One 7 10 2012 e47049
94. Ampac 8.16 with Graphical User Interface, Version 9.0 2009 Semichem, Inc. Shawnee Mission, KS