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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Agric. Food Chem. 2009, 57, 18, 8339-8343
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Identification of Annonaceous Acetogenins in the Ripe Fruit of the North American Pawpaw (Asimina triloba)

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† Land Grant Program, Atwood Research Facility, Kentucky State University, Frankfort, Kentucky 40601-2355
‡ Health Sciences and Educational Services, Nature’s Sunshine Products, Inc., 1655 North Main Street, Spanish Fork, Utah 84660
*Author to whom correspondence should be addressed [telephone (502) 597-5942; fax (502) 597-6381; e-mail [email protected]].
Cite this: J. Agric. Food Chem. 2009, 57, 18, 8339–8343
Publication Date (Web):August 27, 2009
https://doi.org/10.1021/jf9018239
Copyright © 2009 American Chemical Society
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Abstract

The North American pawpaw [Asimina triloba (L.) Dunal] is a tree fruit in the early stages of commercial production in the United States. This plant contains annonaceous acetogenins in the twigs, unripe fruit, seeds, roots, and bark tissues, which display antitumor, pesticidal, antimalarial, anthelmintic, piscicidal, antiviral, and antimicrobial effects, suggesting many potentially useful applications. However, commercial development of these compounds, based on twig extracts, has been problematic due to limited availability of biomass for extraction. Additionally, acetogenin compounds contained in fruit of pawpaw relatives (soursop or Annona muricata) and tea made from the leaves of these plants may lead to an increased risk of atypical Parkinsonism later in life with overconsumption of these compounds. Therefore, the objectives of this study were (1) to determine if extracts of ripe pawpaw fruit pulp displayed acetogenin activity, (2) to identify potential acetogenin compounds in the fruit tissue, and (3) to determine if the acetogenin activity varied in diverse pawpaw genotypes and closely related Annona species. Extracts of ripe fruit had total extract weights and bioactivity using the brine shrimp bioassay similar to those from ‘NC-1’ pawpaw twig tissue. Pulp from soursop, cherimoya, and several additional pawpaw cultivars (‘Mitchell’, ‘Overleese’, ‘NC-1’,‘Zimmerman’, ‘Wells’, and ‘Sunflower’) also displayed bioactivity, but peach or banana pulp did not. Ripe pawpaw pulp extract subjected to HPLC-MS analysis identified three prominent acetogenins: asimicin, bullatacin, and bullatalicin. This study points to pawpaw fruit pulp serving as a new biomass source for the extraction of acetogenin compounds for product development. An assessment of the potential human health risk of overconsumption of fruit and acetogenin bioavailability and degradation studies should be pursued.

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Cited By

This article is cited by 23 publications.

  1. Paige J. Monsen, Frederick A. Luzzio. Antiangiogenic Activity and Chemical Derivatization of the Neurotoxic Acetogenin Annonacin Isolated from Asimina triloba. Journal of Natural Products 2018, 81 (8) , 1905-1909. https://doi.org/10.1021/acs.jnatprod.8b00284
  2. Jessica Le Ven, Isabelle Schmitz-Afonso, Guy Lewin, Alain Brunelle, David Touboul, and Pierre Champy . Identification of the Environmental Neurotoxins Annonaceous Acetogenins in an Annona cherimolia Mill. Alcoholic Beverage Using HPLC-ESI-LTQ-Orbitrap. Journal of Agricultural and Food Chemistry 2014, 62 (34) , 8696-8704. https://doi.org/10.1021/jf501174j
  3. Juan Carlos Ramos, Margarita Brovetto, and Gustavo A. Seoane . Chemoenzymatic Synthesis of trans-Tetrahydrofuran Cores of Annonaceous Acetogenins from Bromobenzene. Organic Letters 2013, 15 (8) , 1982-1985. https://doi.org/10.1021/ol400650v
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  12. Jin-Sik Nam, Seo-Yeon Park, Hyo-Jeong Lee, Seon-Ok Lee, Hye-Lim Jang, Young Ha Rhee. Correlation Between Acetogenin Content and Antiproliferative Activity of Pawpaw ( Asimina triloba [L.] Dunal) Fruit Pulp Grown in Korea. Journal of Food Science 2018, 83 (5) , 1430-1435. https://doi.org/10.1111/1750-3841.14144
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  16. Chun-Wei Liu, Tze-Chiun Yeh, Chia-Hsiu Chen, Chia-Chun Yu, Cheng-Sheng Chen, Duen-Ren Hou, Jih-Hwa Guh. Total synthesis of 14,21-diepi-squamocin-K. Tetrahedron 2013, 69 (14) , 2971-2976. https://doi.org/10.1016/j.tet.2013.02.015
  17. Jessica Le Ven, Isabelle Schmitz-Afonso, Guy Lewin, Olivier Laprévote, Alain Brunelle, David Touboul, Pierre Champy. Comprehensive characterization of Annonaceous acetogenins within a complex extract by HPLC-ESI-LTQ-Orbitrap® using post-column lithium infusion. Journal of Mass Spectrometry 2012, 47 (11) , 1500-1509. https://doi.org/10.1002/jms.3092
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  19. R. Guillopé, M. Escobar-Khondiker, V. Guérineau, O. Laprévote, G. U. Höglinger, P. Champy. Kaurenoic Acid from Pulp of Annona cherimolia in regard to Annonaceae-induced Parkinsonism. Phytotherapy Research 2011, 25 (12) , 1861-1864. https://doi.org/10.1002/ptr.3508
  20. Julie Allegrand, David Touboul, Isabelle Schmitz-Afonso, Vincent Guérineau, Alexandre Giuliani, Jessica Le Ven, Pierre Champy, Olivier Laprévote. Structural study of acetogenins by tandem mass spectrometry under high and low collision energy. Rapid Communications in Mass Spectrometry 2010, 24 (24) , 3602-3608. https://doi.org/10.1002/rcm.4805
  21. John D. Sedlacek, Karen L. Friley, Jeremiah D. Lowe, Kirk W. Pomper. Potential of Ripe Pawpaw Fruit Extract as an Insecticide and Feeding Deterrent for Striped Cucumber Beetle (Coleoptera: Chrysomelidae) on Squash. Journal of Entomological Science 2010, 45 (4) , 378-384. https://doi.org/10.18474/0749-8004-45.4.378
  22. Chia-Hsiu Chen, Ting-Chun Kuan, Ke-Jhen Lu, Duen-Ren Hou. Asymmetric synthesis of bis-tetrahydrofuran cores in annonaceous acetogenins. Organic & Biomolecular Chemistry 2010, 8 (16) , 3624. https://doi.org/10.1039/c004672h
  23. Pierre Champy, Vincent Guérineau, Olivier Laprévote. MALDI-TOF MS Profiling of Annonaceous Acetogenins in Annona muricata Products for Human Consumption. Molecules 2009, 14 (12) , 5235-5246. https://doi.org/10.3390/molecules14125235

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