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Paw Paw and Cancer: Annonaceous Acetogenins from Discovery to Commercial Products
Abstract
Extracts of paw paw ( Asimina triloba, Annonaceae) are among the most potent of the 3500 species of higher plants screened for bioactive compounds in our laboratories at Purdue University. The paw paw is a small tree native to eastern North America; its edible fruits (sometimes referred to as "Indiana Bananas") have nurtured mankind for centuries. Activity-directed fractionation of the paw paw extracts, using the brine shrimp lethality bioassay, led to the isolation and molecular characterization of over 50 unique annonaceous acetogenins. Fractionation of extracts from related species resulted in the identification of over 150 additional acetogenins. The annonaceous acetogenins are derivatives of long-chain (C32 or C34) fatty acids. They are potent inhibitors of mitochondrial (complex I) as well as cytoplasmic (anaerobic) production of adenosine triphosphate (ATP) and the related nucleotides. The powerful cytotoxicity, in vivo antitumor, pesticidal, antimalarial, anthelmintic, piscicidal, antiviral, and antimicrobial effects indicated a myriad of potentially useful applications. Commercial development of these compounds uses natural mixtures of active components, incorporated into pesticidal, topical, and dietary supplement products. Successful applications and commercial products include a shampoo, highly effective in treating infestations of head lice, fleas, and ticks; a series of pesticidal sprays, which protects host plants against a diversity of pests; and an ointment for treatment of oral herpes (HSV-1) and other skin afflictions. The extract (in capsule form) enhances a mixture of natural anthelmintics. In addition, an encapsulated extract has been effectively used by certain cancer patients as a botanical supplement product.
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Cites
Natural products as sources of new drugs over the last 25 years
Newman, D. J., & Cragg, G. M. (2007) · Journal of Natural Products · doi:10.1021/np068054v · Cited by 5,517
Brine Shrimp: A Convenient General Bioassay for Active Plant Constituents
Meyer, B., Ferrigni, N., Putnam, J., Jacobsen, L., Nichols, D., & McLaughlin, J. (1982) · Planta Medica · doi:10.1055/s-2007-971236 · Cited by 4,831
Self-citationChronic systemic pesticide exposure reproduces features of Parkinson's disease
Betarbet, R., Sherer, T. B., MacKenzie, G., Garcia-Osuna, M., Panov, A. V., & Greenamyre, J. T. (2000) · Nature Neuroscience · doi:10.1038/81834 · Cited by 3,683
BIOCHEMISTRY OF MULTIDRUG RESISTANCE MEDIATED BY THE MULTIDRUG TRANSPORTER
Gottesman, M. M., & Pastan, I. (1993) · Annual Review of Biochemistry · doi:10.1146/annurev.bi.62.070193.002125 · Cited by 3,568
DRAIZE, J. H., WOODARD, G., & CALVERY, H. O. (1944) · The Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)08751-8 · Cited by 2,602
Progress in the Chemistry of Organic Natural Products 109
(2019) · Progress in the Chemistry of Organic Natural Products · doi:10.1007/978-3-030-12858-6 · Cited by 2,052
(1993) · Methods in Plant Biochemistry · doi:10.1016/b978-0-12-461020-0.50001-9 · Cited by 1,757
Morton, J. F., & Dowling, C. F. (1987) · Cited by 1,352
Annonaceous Acetogenins: Recent Progress
Alali, F. Q., Liu, X.-X., & McLaughlin, J. L. (1999) · Journal of Natural Products · doi:10.1021/np980406d · Cited by 818
Self-citationThe Use of Biological Assays to Evaluate Botanicals
McLaughlin, J. L., Rogers, L. L., & Anderson, J. E. (1998) · Drug Information Journal · doi:10.1177/009286159803200223 · Cited by 704
Self-citationAcetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action
Bermejo, A., Figadère, B., Zafra-Polo, M.-C., Barrachina, I., Estornell, E., & Cortes, D. (2005) · Nat. Prod. Rep. · doi:10.1039/b500186m · Cited by 583
Annonaceous Acetogenins: A Review
Rupprecht, J. K., Hui, Y.-H., & McLaughlin, J. L. (1990) · Journal of Natural Products · doi:10.1021/np50068a001 · Cited by 508
Self-citationMitochondrial respiratory chain inhibitors induce apoptosis
Wolvetang, E. J., Johnson, K. L., Krauer, K., Ralph, S. J., & Linnane, A. W. (1994) · FEBS Letters · doi:10.1016/0014-5793(94)80380-3 · Cited by 398
(1989) · Chemical & Engineering News Archive · doi:10.1021/cen-v067n018.p047 · Cited by 383
The phytochemistry of the annonaceae
Leboeuf, M., Cavé, A., Bhaumik, P. K., Mukherjee, B., & Mukherjee, R. (1980) · Phytochemistry · doi:10.1016/0031-9422(80)85046-1 · Cited by 376
Human Medicinal Agents from Plants
(1993) · ACS Symposium Series · doi:10.1021/bk-1993-0534 · Cited by 367
Recent advances in annonaceous acetogenins
Zeng, L., Ye, Q., Oberlies, N. H., Shi, G., Gu, Z.-M., He, K., & McLaughlin, J. L. (1996) · Natural Product Reports · doi:10.1039/np9961300275 · Cited by 355
Self-citationElevated insulin receptor content in human breast cancer
Papa, V, Pezzino, V, Costantino, A., Belfiore, A., Giuffrida, D., Frittitta, L., Vannelli, G. B., Brand, R., Goldfine, I. D., & Vigneri, R. (1990) · Journal of Clinical Investigation · doi:10.1172/jci114868 · Cited by 338
Oliver, J. M., Burg, D. L., Wilson, B. S., McLaughlin, J. L., & Geahlen, R. L. (1994) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)43936-1 · Cited by 338
Self-citationChronic systemic complex I inhibition induces a hypokinetic multisystem degeneration in rats
Höglinger, G. U., Féger, J., Prigent, A., Michel, P. P., Parain, K., Champy, P., Ruberg, M., Oertel, W. H., & Hirsch, E. C. (2003) · Journal of Neurochemistry · doi:10.1046/j.1471-4159.2003.01533.x · Cited by 331
Insulin-like growth factor receptor expression and function in human breast cancer.
Cullen, K. J., Yee, D., Sly, W. S., Perdue, J. F., Hampton, B., Lippman, M. E., & Rosen, N. X. (1990) · PubMed · Cited by 319
Caparros-Lefebvre, D., & Elbaz, A. (1999) · The Lancet · doi:10.1016/s0140-6736(98)10166-6 · Cited by 255
Champy, P., Höglinger, G. U., Féger, J., Gleye, C., Hocquemiller, R., Laurens, A., Guérineau, V., Laprévote, O., Medja, F., Lombès, A., et al. (2004) · Journal of Neurochemistry · doi:10.1046/j.1471-4159.2003.02138.x · Cited by 254
Rieser, M. J., Hui, Y. H., Rupprecht, J. K., Kozlowski, J. F., Wood, K. V., McLaughlin, J. L., Hanson, P. R., Zhuang, Z., & Hoye, T. R. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00052a018 · Cited by 245
Self-citationDegli Esposti, M., Ghelli, A., Ratta, M., Cortes, D., & Estornell, E. (1994) · Biochemical Journal · doi:10.1042/bj3010161 · Cited by 239
Isoquinoline neurotoxins in the brain and Parkinson's disease
Nagatsu, T. (1997) · Neuroscience Research · doi:10.1016/s0168-0102(97)00083-7 · Cited by 229
Annonacin, a Natural Mitochondrial Complex I Inhibitor, Causes Tau Pathology in Cultured Neurons
Escobar-Khondiker, M., Höllerhage, M., Muriel, M.-P., Champy, P., Bach, A., Depienne, C., Respondek, G., Yamada, E. S., Lannuzel, A., Yagi, T., et al. (2007) · The Journal of Neuroscience · doi:10.1523/jneurosci.1644-07.2007 · Cited by 212
Mode of action of bullatacin: A potent antitumor and pesticidal Annonaceous acetogenin
Ahammadsahib, K. I., Hollingworth, R. M., McGovren, J. P., Hui, Y.-H., & McLaughlin, J. L. (1993) · Life Sciences · doi:10.1016/0024-3205(93)90547-g · Cited by 188
Self-citationOberlies, N. H., Chang, C.-J., & McLaughlin, J. L. (1997) · Journal of Medicinal Chemistry · doi:10.1021/jm9700169 · Cited by 178
Self-citationGuadeloupean parkinsonism: a cluster of progressive supranuclear palsy‐like tauopathy
Caparros‐Lefebvre, D., Sergeant, N., Lees, A., Camuzat, A., Daniel, S., Lannuzel, A., Brice, A., Tolosa, E., Delacourte, A., & Duyckaerts, C. (2002) · Brain · doi:10.1093/brain/awf086 · Cited by 170
Lannuzel, A., Michel, P. P., Höglinger, G. U., Champy, P., Jousset, A., Medja, F., Lombès, A., Darios, F., Gleye, C., Laurens, A., et al. (2003) · Neuroscience · doi:10.1016/s0306-4522(03)00441-x · Cited by 168
James Morré, D., de Cabo, R., Farley, C., Oberlies, N. H., & McLaughlin, J. L. (1994) · Life Sciences · doi:10.1016/0024-3205(94)00957-0 · Cited by 168
Self-citationZhao, G., Hui, Y., Rupprecht, J. K., McLaughlin, J. L., & Wood, K. V. (1992) · Journal of Natural Products · doi:10.1021/np50081a011 · Cited by 161
Self-citationSchuler, F., Yano, T., Di Bernardo, S., Yagi, T., Yankovskaya, V., Singer, T. P., & Casida, J. E. (1999) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.96.7.4149 · Cited by 160
Hollingworth, R. M., Ahammadsahib, K. I., Gadelhak, G., & McLaughlin, J. L. (1994) · Biochemical Society Transactions · doi:10.1042/bst0220230 · Cited by 160
Self-citationCragg, G. M. L., Newman, D. J., & Yang, S. S. (2006) · Journal of Natural Products · doi:10.1021/np0581216 · Cited by 142
Oberlies, N. H., Croy, V. L., Harrison, M. L., et al. (1997) · Cancer Letters · doi:10.1016/s0304-3835(97)04716-2 · Cited by 142
Biologically Active Natural Products: Pharmaceuticals
Cutler, S. J., & Cutler, H. G. (2018) · Medical Entomology and Zoology · Cited by 137
Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe
Champy, P., Melot, A., Guérineau, V., Gleye, C., Fall, D., Höglinger, G. U., Ruberg, M., Lannuzel, A., Laprévôte, O., Laurens, A., et al. (2005) · Movement Disorders · doi:10.1002/mds.20632 · Cited by 136
Lannuzel, A., Michel, P. P., Caparros-Lefebvre, D., Abaul, J., Hocquemiller, R., & Ruberg, M. (2002) · Movement Disorders · doi:10.1002/mds.1246 · Cited by 116
Lewis, M. A., Arnason, J. T., Philogène, B. J. R., Rupprecht, J. K., & McLaughlin, J. L. (1993) · Pesticide Biochemistry and Physiology · doi:10.1006/pest.1993.1003 · Cited by 111
Self-citationMiyoshi, H., Ohshima, M., Shimada, H., AKAGI, T., Iwamura, H., & McLaughlin, J. L. (1998) · Biochimica et Biophysica Acta (BBA) - Bioenergetics · doi:10.1016/s0005-2728(98)00097-8 · Cited by 108
Self-citationTumor cell growth inhibition by several Annonaceous acetogenins in an in vitro disk diffusion assay
Oberlies, N. H., Jones, J. L., Corbett, T. H., Fotopoulos, S. S., & McLaughlin, J. L. (1995) · Cancer Letters · doi:10.1016/0304-3835(95)92759-7 · Cited by 96
Self-citationLandolt, J. L., Ahammadsahib, K. I., Hollingworth, R. M., Barr, R., Crane, F. L., Buerckv, N. L., McCabe, G. P., & McLaughlin, J. L. (1995) · Chemico-Biological Interactions · doi:10.1016/0009-2797(95)03628-y · Cited by 79
Self-citationChih, H.-W., Chiu, H., Tang, K.-S., Chang, F., & Wu, Y. (2001) · Life Sciences · doi:10.1016/s0024-3205(01)01209-7 · Cited by 77
Total Synthesis of Asimicin and Bullatacin
Avedissian, H., Sinha, S. C., Yazbak, A., et al. (2000) · The Journal of Organic Chemistry · doi:10.1021/jo000500a · Cited by 76
Annonacin, a novel, biologically active polyketide fromAnnona densicoma
McCloud, T. G., SMITH, D. L., Chang, C. J., et al. (1987) · Cellular and Molecular Life Sciences · doi:10.1007/bf01951681 · Cited by 75
Phytochemicals in Human Health Protection, Nutrition, and Plant Defense
Romeo, J. T. (1999) · Springer eBooks · doi:10.1007/978-1-4615-4689-4 · Cited by 72
Asimin, Asiminacin, and Asiminecin: Novel Highly Cytotoxic Asimicin Isomers from Asimina triloba
Zhao, G., Miesbauer, L. R., Smith, D. L., & McLaughlin, J. L. (1994) · Journal of Medicinal Chemistry · doi:10.1021/jm00039a009 · Cited by 69
Self-citationInsecticidal and Mutagenic Evaluation of Two Annonaceous Acetogenins
Guadaño, A., Gutiérrez, C., de la Peña, E., Cortés, D., & González‐Coloma, A. (2000) · Journal of Natural Products · doi:10.1021/np990328+ · Cited by 67
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Jung, J. H., Pummangura, S., Chaichantipyuth, C., Patarapanich, C., Fanwick, P. E., Chang, C., & McLaughlin, J. L. (1990) · Tetrahedron · doi:10.1016/s0040-4020(01)87811-x · Cited by 66
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Murai, M., Ishihara, A., Nishioka, T., Yagi, T., & Miyoshi, H. (2007) · Biochemistry · doi:10.1021/bi7003697 · Cited by 62
Hopp, D. C., Zeng, L., Gu, Z.-M., et al. (1996) · Journal of Natural Products · doi:10.1021/np960124i · Cited by 61
Hopp, D. C., Zeng, L., Gu, Z.-M., et al. (1997) · Journal of Natural Products · doi:10.1021/np9701283 · Cited by 52
Ratnayake, S., Rupprecht, K. J., Potter, W. M., & McLaughlin, J. L. (1992) · Journal of Economic Entomology · doi:10.1093/jee/85.6.2353 · Cited by 49
Self-citationZhao, G., Gu, Z.-M., Zeng, L., Chao, J., Kozlowski, J. F., Wood, K. V., & McLaughlin, J. L. (1995) · Tetrahedron · doi:10.1016/0040-4020(95)00364-e · Cited by 47
Self-citationBiologically active acetogenins from stem bark of Asimina triloba
ZHAO, G. ‐., Rieser, M. J., Hui, Y. ‐., et al. (1993) · Phytochemistry · doi:10.1016/0031-9422(93)85024-l · Cited by 45
Rapid separation of triterpenoids from Neem seed extracts
Jarvis, A. P., Morgan, E. D., & Edwards, C. (1999) · Phytochemical Analysis · doi:10.1002/(sici)1099-1565(199901/02)10:1<32::aid-pca433>3.0.co;2-d · Cited by 43
Atypical parkinsonism and Annonaceae consumption in New Caledonia
Angibaud, G., Gaultier, C., & Rascol, O. (2004) · Movement Disorders · doi:10.1002/mds.20104 · Cited by 42
Friedrich, T., Ohnishi, T., Forche, E., Kunze, B., Jansen, R., Trowitzsch, W., Höfle, G., Reichenbach, H., & Weiss, H. (1994) · Biochemical Society Transactions · doi:10.1042/bst0220226 · Cited by 41
Woo, M. H., Cho, K. Y., Zhang, Y., Zeng, L., Gu, Z.-M., & McLaughlin, J. L. (1995) · Journal of Natural Products · doi:10.1021/np50124a009 · Cited by 33
Self-citationAtypical unclassifiable parkinsonism on Guadeloupe: An environmental toxic hypothesis
Caparros-Lefebvre, D., & Lees, A. J. (2005) · Movement Disorders · doi:10.1002/mds.20553 · Cited by 32
Bullatalicin, a novel bioactive acetogenin from Annona bullata (Annonaceae)
Hui, Y., Rupprecht, J. K., Anderson, J. E., et al. (1989) · Tetrahedron · doi:10.1016/s0040-4020(01)89160-2 · Cited by 27
Caparros-Lefebvre, D., & Steele, J. C. (2005) · Environmental Toxicology and Pharmacology · doi:10.1016/j.etap.2004.12.052 · Cited by 27
Insulin, chemotherapy, and the mechanisms of malignancy: the design and the demise of cancer
Ayre, S. G., y Bellon, D. P. G., & Jr, D. P. G. (2000) · Medical Hypotheses · doi:10.1054/mehy.2000.1063 · Cited by 22
Additional bioactive annonaceous acetogenins from Asimina triloba (Annonaceae)
He, K., Zhao, G., Shi, G., Zeng, L., Chao, J., & McLaughlin, J. L. (1997) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(96)00264-7 · Cited by 18
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Metadata
- Authors
- McLaughlin, J. L.
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-07-01
- Volume
- 71
- Issue
- 7
- Pages
- 1311-1321
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W2172164746
- Cited by
- 294
- References
- 66
- FWCI
- 8.12
- Type
- journal article
- Language
- en
- Open access
- closed
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