Chemical modification produces species-specific changes in cucurbitacin antifeedant effect

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 23, 2013, Pages 5534-5539

  Lang, Karen Luise ^a   Deagosto, Emilio ^b   Zimmermann, Lara Almida ^a   Machado, Vanessa Rocha ^a   Campos Bernardes, Lílian Sibelle ^a   Schenkel, Eloir Paulo ^a   Duran, Fernando Javier ^c   Palermo, Jorge ^c   Rossini, Carmen ^b  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

anti insect; antiherbivory; cucurbitacins; deterrent; semisynthesis; triterpenoid

Indexed keywords

ANTI-INSECT; ANTIHERBIVORY; CUCURBITACINS; DETERRENT; SEMISYNTHESIS; TRITERPENOIDS;

MUSCULOSKELETAL SYSTEM;

CHEMICAL MODIFICATION;

CUCURBITACIN; PLANT EXTRACT;

ANIMAL; ARTICLE; BEETLE; CHEMICAL STRUCTURE; CHEMISTRY; CUCURBITACEAE; DRUG EFFECT; FEEDING BEHAVIOR; LEPIDOPTERA; PHYSIOLOGY; SPECIES DIFFERENCE;

ANIMALS; BEETLES; CUCURBITACEAE; CUCURBITACINS; FEEDING BEHAVIOR; LEPIDOPTERA; MOLECULAR STRUCTURE; PLANT EXTRACTS; SPECIES SPECIFICITY;

COCCINELLIDAE; COLEOPTERA; CUCURBITACEAE; EPILACHNA PAENULATA; HEXAPODA; LEPIDOPTERA; MYTHIMNA; NOCTUIDAE;

EID: 84879014304     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4002457     Document Type: Article

References (38)

1. Dinan, L.; Harmatha, J.; Lafont, R. Chromatographic procedures for the isolation of plant steroids J. Chromatogr., A 2001, 935, 105-123 (Pubitemid 33044643)
2. Miro, M. Cucurbitacins and their pharmacological effects Phytother. Res. 1995, 9, 159-168
3. Koul, O. Phytochemicals and insect control: an antifeedant approach Crit. Rev. Plant Sci. 2008, 27, 1-24 (Pubitemid 351878168)
4. Tallamy, D. W.; Stull, J.; Ehresman, N. P.; Gorski, P. M.; Mason, C. E. Cucurbitacins as feeding and oviposition deterrents to insects Environ. Entomol. 1997, 26, 678-683 (Pubitemid 127481544)
5. Carroll, C. R.; Hoffman, C. A. Chemical feeding deterrent mobilized in response to insect herbivory and counteradaptation by Epilachna tredecimnotata Science 1980, 209, 414-416
6. Tallamy, D. W. Squash beetle Epilachna borealis feeding behavior: an adaptation against induced cucurbit defenses Ecology 1985, 66, 1574-1579 (Pubitemid 17249997)
7. Fraenkel, G. S. Raison d'eître of secondary plant substances Science 1959, 129, 1466-1470
8. Metcalf, R. L.; Metcalf, R. A.; Rhodes, A. M. Cucurbitacins as kairomones for Diabroticite beetles Proc. Natl. Acad. Sci. U. S. A. 1980, 77, 3769-3772 (Pubitemid 10015463)
9. Metcalf, R. L.; Lampman, R. L. The chemical ecology of Diabroticites and Cucurbitaceae Experientia 1989, 45, 240-247
10. Ferguson, J. E.; Metcalf, E. R.; Metcalf, R. L.; Rhodes, A. M. Influence of cucurbitacin content in cotyledons of cucurbitaceae cultivars upon feeding-behavior of Diabroticina beetles (Coleoptera, Chrysomelidae) J. Econ. Entomol. 1983, 76, 47-51
11. Ferguson, J. E.; Metcalf, R. L. Cucurbitacins. Plant derived defense compounds for Diabroticites (Coleoptera: Chrysomelidae) J. Chem. Ecol. 1985, 11, 311-318
12. Metcalf, R. L. Coevolutionary adaptations of rootworm beetles (Coleoptera: Chrysomelidae) to cucurbitacins J. Chem. Ecol. 1986, 12, 1109-1124
13. Dinan, L.; Savchenko, T.; Whiting, P.; Sarker, S. D. Plant natural products as insect steroid receptor agonists and antagonists Pestic. Sci. 1999, 55, 331-335 (Pubitemid 29131951)
14. Dinan, L.; Bourne, P. C.; Meng, Y.; Sarker, S. D.; Tolentino, R. B.; Whiting, P. Assessment of natural products in the Drosophila melanogaster B-II cell bioassay for ecdysteroid agonist and antagonist activities Cell. Mol. Life Sci. 2001, 58, 321-342 (Pubitemid 32217364)
15. Huang, R. C.; Renwick, J. A. A.; Sachdevgupta, K. Oviposition stimulants and deterrents regulating differential acceptance of Iberis amara by Pieris rapae and P. napi oleracea J. Chem. Ecol. 1993, 19, 1645-1663
16. Nielsen, J. K. Host plant discrimination within Cruciferae. Feeding responses of four leaf Beetles (Coleoptera: Chrysomelidae) to glucosinolates, cucurbitacins and cardenolides Entomol. Exp. Appl. 1978, 24, 41-54
17. Sachdevgupta, K.; Radke, C. D.; Renwick, J. A. A. Antifeedant activity of cucurbitacins from Iberis amara against larvae of Pieris rapae Phytochemistry 1993, 33, 1385-1388
18. Salom, S. M.; Carlson, J. A.; Ang, B. N.; Grosman, D. M.; Day, E. R. Laboratory evaluation of biologically-based compounds as antifeedants for the pales weevil, Hylobius pales Herbst (Coleoptera: Curculionidae) J. Entomol. Sci. 1994, 29, 407-419 (Pubitemid 2129986)
19. Salom, S. M.; Gray, J. A.; Alford, A. R.; Mulesky, M.; Fettig, C. J.; Woods, S. A. Evaluation of natural products as antifeedants for the pales weevil (Coleoptera: Curculionide) and as fungitoxins for Leptographium procerum J. Entomol. Sci. 1996, 31, 453-465 (Pubitemid 27086316)
20. Arruda, I. C.; Ventura, M. U.; Scarminio, I. S. Feeding and arrestment responses of Diabrotica speciosa to cucurbitacin-content formulations Pesqui. Agropecu. Bras. 2005, 40, 639-643 (Pubitemid 41336871)
21. Metcalf, R. L.; Ferguson, J. E.; Lampman, R. L.; Andersen, J. F. Dry cucurbitacin-containing baits for controlling Diabroticite beetles (Coleoptera: Chrysomelidae) J. Econ. Entomol. 1987, 80, 870-875
22. Lampman, R. L.; Metcalf, E. R. The comparative response of Diabrotica species (Coleoptera: Chrysomelidae) to volatile attractants Environ. Entomol. 1988, 17, 644-648 (Pubitemid 19326198)
23. Parimi, S.; Meinke, L. J.; Nowatzki, T. M.; Chandler, L. D.; French, B. W.; Siegfried, B. D. Toxicity of insecticide-bait mixtures to insecticide resistant and susceptible western corn rootworms (Coleoptera: Chrysomelidae) Crop Prot. 2003, 22, 781-786 (Pubitemid 36708071)
24. Chen, J. C.; Chiu, M. H.; Nie, R. L.; Cordell, G. A.; Qiu, S. X. Cucurbitacins and cucurbitane glycosides: structures and biological activities Nat. Prod. Rep. 2005, 22, 386-399
25. Ríos, J. L.; Escandell, J. M.; Recio, M. C. New Insights into the Bioactivity of Cucurbitacins. 5th ed.; Elsevier: Karachi, 2005; Vol. 32.
26. Lang, K. L. Obtenção de cucurbitacinas a partir de plantas nativas e modificações estruturais visando à síntese de compostos bioativos.. Ph.D. thesis. Universidade Federal de Santa Catarina, 2012; 304 pp.
27. Lang, K. L.; Silva, I. T.; Zimmermann, L. A.; Machado, V. R.; Teixeira, M. R.; Lapuh, M. I.; Galetti, M. A.; Palermo, J. A.; Cabrera, G. M.; Bernardes, L. S. C.; Simoes, C. M. O.; Schenkel, E. P.; Caro, M. S. B.; Durán, F. J. Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives Bioorg. Med. Chem. 2012, 20, 3016-3030
28. Scatoni, I. B.; Bentancourt, C. Guía de Insectos y ácaros de Importancia Agrícola y Forestal en El Uruguay. 3rd ed.; Hemisferio Sur: Montevideo, 2010; p 598.
29. Farias, M. R.; Schenkel, E. P.; Mayer, R.; Rucker, G. Cucurbitacins as constituents of Wilbrandia ebracteata Planta Med. 1993, 59, 272-275 (Pubitemid 23168780)
30. Lang, K. L.; Da Rosa Guimaraes, T.; Rocha Machado, V.; Zimmermann, L. A.; Silva, I. T.; Teixeira, M. R.; Durán, F. J.; Palermo, J. A.; Simoes, C. M. O.; Caro, M. S. B.; Schenkel, E. P. New cytotoxic cucurbitacins from Wilbrandia ebracteata Cogn Planta Med. 2011, 77, 1648-1651
31. Camarano, S.; González, A.; Rossini, C. Chemical defense of the ladybird beetle Epilachna paenulata Chemoecology 2006, 16, 179-184 (Pubitemid 44787896)
32. Poitout, S.; Bues, R. Rearing larvae of twentyeight species of Noctuidae and two species of Arctiidae (Lepidoptera) on a simple artificial diet breeding peculiarities according to the different species Ann. Zool. Ecol. Anim. 1974, 6, 431-441
33. Bellomo, A.; Camarano, S.; Rossini, C.; Gonzalez, D. Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols Carbohydr. Res. 2009, 344, 44-51
34. Diaz, M.; Castillo, L.; Diaz, C. E.; González-Coloma, A.; Rossini, C. Limonoids from Melia azedarach with deterrent activity against insects Nat. Prod. J. 2012, 2, 36-44
35. Mansson, E.; Schylter, F. Hylobius pine weevils adult host selection and antifeedants: feeding behaviour on host and non-host scandinavian plants Agric. For. Entomol. 2004, 6, 165-171
36. Lowry, R. VassarStats: Web Site for Statistical Computation; Vassar College: Poughkeepsie, NY, 1998-2013; http://vassarstats.net/ (Accessed December 20, 2012).
37. Bernays, E. A. When host choice is a problem for a generalist herbivore: experiments with the whitefly, Bemisia tabaci Ecol. Entomol. 1999, 24, 260-267 (Pubitemid 29411962)
38. Bernays, E. A.; Minkenberg, O. P. J. M. Insect herbivores: different reasons for being a generalist Ecology 1997, 78, 1157-1169