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Chemical Defense in the Zebra Swallowtail Butterfly, Eurytides marcellus, Involving Annonaceous Acetogenins

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Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, College of Arts and Sciences, Science Division, Widener University, One University Place, Chester, Pennsylvania 19013-5792, and Xenobiotic Laboratories, Inc., 107 Morgan Lane, Plainsboro New Jersey 08536
Cite this: J. Nat. Prod. 1999, 62, 1, 2–4
Publication Date (Web):October 21, 1998
https://doi.org/10.1021/np980308s
Copyright © 1999 American Chemical Society and American Society of Pharmacognosy

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    Abstract

    Few herbivores feed on the foliage of the North American paw paw tree, Asimina triloba; notable exceptions are the larvae of the zebra swallowtail butterfly, Eurytides marcellus. Toxic annonaceous acetogenins, produced by A. triloba, are responsible for the relative unpalatability of the leaves. Acetogenins found in A. triloba extracts are potent pesticidal and antineoplastic agents and have emetic activity in vertebrates. In this study, partitioned aqueous MeOH fractions of the bioactive CH2Cl2 extracts, of freeze-dried and pulverized larvae, and of mature butterflies revealed acetogenin content through the use of HPLC coupled to tandem MS (LC-MS/MS). This sensitive technique provides an uncomplicated method for the detection of trace compounds and, in this instance, has confirmed tissue presence of acetogenins that serve a probable role as chemical defense agents against bird predation in zebra swallowtail larvae and adults.

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     Purdue University.

     Widener University.

    §

     Xenobiotic Laboratories, Inc.

    *

     To whom correspondence should be addressed. Tel.:  765-494-1455. Fax:  765-494-1414. E-mail:  [email protected].

    Cited By

    This article is cited by 12 publications.

    1. Kirk W. Pomper, Jeremiah D. Lowe, Sheri B. Crabtree and William Keller . Identification of Annonaceous Acetogenins in the Ripe Fruit of the North American Pawpaw (Asimina triloba). Journal of Agricultural and Food Chemistry 2009, 57 (18) , 8339-8343. https://doi.org/10.1021/jf9018239
    2. Jerry L. McLaughlin. Paw Paw and Cancer: Annonaceous Acetogenins from Discovery to Commercial Products. Journal of Natural Products 2008, 71 (7) , 1311-1321. https://doi.org/10.1021/np800191t
    3. Feras Q. Alali,, Xiao-Xi Liu, and, Jerry L. McLaughlin. Annonaceous Acetogenins:  Recent Progress. Journal of Natural Products 1999, 62 (3) , 504-540. https://doi.org/10.1021/np980406d
    4. Ihtisham Ul Haq, Kashif Rahim, Muhammad Rafiq, Tayyaba Asif, Sifa Alvi, Kinza Yaseen. Polyketides and SARS-CoV-2. 2023, 423-444. https://doi.org/10.1016/B978-0-323-95047-3.00020-4
    5. Claudia Azucena Durán-Ruiz, Rocío Cruz-Ortega, Alejandro Zaldívar-Riverón, Hilda Araceli Zavaleta-Mancera, Iván De-la-Cruz-Chacón, Alma Rosa González-Esquinca. Ontogenic synchronization of Bephratelloides cubensis, Annona macroprophyllata seeds and acetogenins from Annonaceae. Journal of Plant Research 2019, 132 (1) , 81-91. https://doi.org/10.1007/s10265-018-01078-3
    6. R. Pradeep Kumar, K.V. Dinesh Babu, D.A. Evans. Isolation, characterization and mode of action of a larvicidal compound, 22-hydroxyhopane from Adiantum latifolium Lam. against Oryctes rhinoceros Linn.. Pesticide Biochemistry and Physiology 2019, 153 , 161-170. https://doi.org/10.1016/j.pestbp.2018.11.018
    7. Marilza Costa, Jamile Cossolin, Mônica Pereira, Antônio Sant'Ana, Milena Lima, José Zanuncio, José Serrão. Larvicidal and Cytotoxic Potential of Squamocin on the Midgut of Aedes aegypti (Diptera: Culicidae). Toxins 2014, 6 (4) , 1169-1176. https://doi.org/10.3390/toxins6041169
    8. 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
    9. 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
    10. Almudena Bermejo, Bruno Figadère, Maria-Carmen Zafra-Polo, Isabel Barrachina, Ernesto Estornell, Diego Cortes. Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action. Nat. Prod. Rep. 2005, 22 (2) , 269-303. https://doi.org/10.1039/B500186M
    11. Stephen R. Madigosky. Survival Strategies: A Matter of Life and Death. 2004, 423-450. https://doi.org/10.1016/B978-012457553-0/50028-9
    12. P. Rasoanaivo, M-T. Martin, E. Guittet, F. Frappier. New contributions to the structure elucidation and pharmacology of Strychnos alkaloids. 2002, 1029-1072. https://doi.org/10.1016/S1572-5995(02)80024-2

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