Insect growth regulatory effects of some extracts and sterols from Myrtillocactus geometrizans (Cactaceae) against Spodoptera frugiperda and Tenebrio molitor

Phytochemistry

Volumn 66, Issue 20, 2005, Pages 2481-2493

  Céspedes, Carlos L ^a   Salazar, J Rodrigo ^a   Martínez, Mariano ^a   Aranda, Eduardo ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MORELOS   (Mexico)

Author keywords

Cactaceae; Ecdysone mimics; Fall armyworm; Insect growth regulation; IPM; Myrtillocactus geometrizans; Phytoecdysteroids; Spodoptera frugiperda; Sterols; Tenebrio molitor

Indexed keywords

GEDUNIN; INSECTICIDE; JUVENILE HORMONE; LIMONOID; PLANT EXTRACT; STEROL;

ANIMAL; ARMYWORM; ARTICLE; CACTACEAE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; LARVA; TENEBRIO; TOXICITY TESTING;

ANIMALS; CACTACEAE; DOSE-RESPONSE RELATIONSHIP, DRUG; INSECTICIDES; JUVENILE HORMONES; LARVA; LIMONINS; PLANT EXTRACTS; SPODOPTERA; STEROLS; TENEBRIO; TOXICITY TESTS;

CACTACEAE; CEDRELA; CEDRELA SALVADORENSIS; COLEOPTERA; INSECTA; LEPIDOPTERA; MYRTILLOCACTUS GEOMETRIZANS; NOCTUIDAE; SPODOPTERA FRUGIPERDA; TENEBRIO; TENEBRIO MOLITOR; ZEA MAYS;

EID: 26444484530     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2005.07.010     Document Type: Article

References (77)

1. E. Aranda, J. Sánchez, M. Peferoen, L. Guereca, and A. Bravo Interactions of Bacillus thuringiensis crystal proteins with the midgut epithelial cells of Spodoptera frugiperda (Lepidoptera: Noctuidae) J. Invertebr. Pathol. 68 1996 203 212
2. J.T. Arnason, B.J.R. Philogène, N. Donskov, and I. Kubo Limonoids from the Meliaceae and Rutaceae reduce feeding, growth and development of Ostrinia nubilalis Entomol. Exp. Appl. 43 3 1987 221 226
3. Arias, S., Gamma, S., Guzmán, L. 1997. Flora del Valle de Tehuacán-Cuicatlán. Fascículo 14. Cactaceae A.L. Juss. Instituto de Biología, UNAM, México D.F., México.
4. S.K. Agarwal, V. Sushma, S.S. Singh, A.K. Tripathi, Z.K. Khan, and K. Sushil Antifeedant and antifungal activity of chromene compounds isolated from Blepharispermum subsessile J. Ethnopharmacol. 71 2000 231 234
5. U.H. Baltaev Phytoecdysteroids: structure, sources and biosynthetic pathways in plants Bioorg. Khim. (Russia) 26 12 2000 892 925
6. M. Berenbaum Allelochemicals in insect-microbe-plant interactions: agents provocateurs in the coevolutionary arms race P. Barbosa K. Letorneau Novel Aspects of Insect-Plant Interactions 1988 Wiley New York 97 124
7. H. Berghiche, G. Smagghe, and N. Soltani In vitro effects of RH-0345 and KK-42 on ecdysteroids level and cuticle synthesis by pupal integument of mealworms Commun. Agric. Appl. Biol. Sci. 68 1 2003 43 48
8. M.C. Carpinella, G.C. Ferrayoli, G. Valladares, M. Defagó, and S. Palacios Potent insect antifeedant limonoid from Melia azedarach Biosci. Biotechnol. Biochem. 66 2002 1731 1736
9. M.C. Carpinella, M. Defagó, G. Valladares, and S. Palacios Antifeedant and insecticidal properties of a limonoid from Melia azedarach (Meliaceae) with potential use for pest management J. Agric. Food Chem. 51 2003 369 374
10. J.S. Calderón, C.L. Céspedes, R. Rosas, F. Gómez-Garibay, J.R. Salazar, L. Lina, E. Aranda, and I. Kubo Acetylcholinesterase and insect growth inhibitory activities of Gutierrezia microcephala on fall armyworm Spodoptera frugiperda J. E. Smith Z. Naturforschung. c 56 2001 382 394
11. F.M. Camps Relaciones Planta-Insecto: Insecticidas de origen vegetal X. Bellés Insecticidas Bioracionales 1988 CSIC Madrid 69 86
12. F.R. Carrizo, M.E. Sosa, L.S. Favier, F. Penna, E. Guerreiro, O.S. Giordano, and C.E. Tonn Growth inhibitory activities of benzofuran and chromene derivatives toward Tenebrio molitor J. Nat. Prod. 61 1998 1209 1211
13. C.L. Céspedes, J.S. Calderón, L. Lina, and E. Aranda Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae) J. Agric. Food Chem. 48 2000 1903 1908
14. C.L. Céspedes, J. Alarcón, E. Aranda, J. Becerra, and M. Silva Insect growth regulatory and insecticidal activity of β- dihydroagarofurans from Maytenus spp. (Celastraceae) Z. Naturforsch. c 56 2001 603 613
15. C.L. Céspedes, M. Martínez-Vázquez, J.S. Calderón, J.R. Salazar, and E. Aranda Insect growth regulatory activity of some extracts and compounds from Parthenium argentatum on fall armyworm Spodoptera frugiperda Z. Naturforsch. c 56 2001 95 105
16. C.L. Céspedes, P. Torres, J.C. Marín, A. Arciniegas, A.L. Perez-Castorena, A. Romo de Vivar, and E. Aranda Insect growth inhibition by tocotrienols and hydroquinones from Roldana barba-johannis (Asteraceae) Phytochemistry 65 13 2004 1963 1975
17. Champagne, D.E., Isman, M.B., Towers, G.H.N. 1989. Insecticidal activity of phytochemicals and extracts of the Meliaceae. In: Arnason, J.T., Philogene, B.J.R., Morand, P. (Eds.), Insecticides of Plant Origin. ACS Symposium Series, vol. 387, pp. 95-109.
18. T.S. Dhadialla, G.R. Carlson, and D.P. Le New insecticides with ecdysteroidal and juvenile hormone activity Annu. Rev. Entomol. 43 1998 545 569
19. L. Dinan Phytoecdysteroids: biological aspects Phytochemistry 57 2001 325 339
20. L. Dinan, T. Savchenko, and P. Whiting On the distribution of phytoecdysteroids in plants Cell Mol. Life Sci. (Switzerland) 58 8 2001 1121 1132
21. C. Djerassi, S. Burstein, H. Estrada, A. Lemin, A.E. Lippman, A. Manjarrez, and H.G. Monsimer Terpenoids. XXVIII. The triterpene composition of the genus Myrtillocactus J. Am. Chem. Soc. 79 1957 3525 3528
22. 7-cholesten-3β-ol a link in sterol biogenesis J. Am. Chem. Soc. 80 1958 6284 6292
23. C. Djerassi, R.D. Murray, and R. Villotti The structure of the cactus sterol, peniocerol (cholest-8-ene-3β,6α-diol) J. Chem. Soc. 1965 1160 1165
24. S.S. Duffey, and M.J. Stout Antinutritive and toxic components of plant defense against insects Arch. Insect Biochem. 32 1996 3 37
25. P.P. Feeny Effect of oak leaf tannins on larval growth of the winter moth Operophtera brumata J. Insect Physiol. 14 1968 805 817
26. P.P. Feeny Plant apparency and chemical defense J.W. Wallace R.L. Mansell Biochemical Interactions between Plants and Insects 1976 Plenum Press New York 1 40
27. R.Y. Feng, W.K. Chen, and M.B. Isman Synergism of malathion and inhibition of midgut esterase activities by an extract from Melia toosendan (Meliaceae) Pestic. Biochem. Physiol. 53 1995 34 41
28. J.A. González, and A. Estevez-Braun Effect of E-chalcone on potato-cyst nematodes (Globodera pallida and G. rostochiensis) J. Agric. Food Chem. 46 1998 1163 1165
29. D.G. Hammond, and I. Kubo Structure-activity relationship of alkanols as mosquito larvicides with novel findings regarding their mode of action Bioorg. Med. Chem. 7 1999 271 278
30. P.A. Hedin, W.L. Parrott, and J.N. Jenkins Effects of cotton plant allelochemicals and nutrients on behaviour and development of tobacco budworm J. Chem. Ecol. 17 6 1991 1107 1121
31. S. Hesterlee, and D.B. Morton Insect physiology: the emerging story of ecdysis Curr. Biol. 6 6 1996 648 650
32. N. Ikekawa, M. Morisaki, and Y. Fujimoto Sterol metabolism in insects: dealkylation of phytosterol to cholesterol Acc. Chem. Res. 26 1993 139 146
33. R. Karban, and K.J. Baxter Induced resistance in wild tobacco with clipped sage brush neighbors: the role of herbivore behavior J. Insect Behav. 14 2001 147 156
34. A. Kessler, and I.T. Baldwin Plant responses to insect herbivory: the emerging molecular analysis Annu. Rev. Plant Biol. 53 2002 299 328
35. P.W. Khong, and K.G. Lewis New triterpenoids extractives from Lemaireocereus chichipe Austr. J. Chem. 28 1975 165 172
36. J.A. Klocke, and I. Kubo Citrus limonoids by-products as insect control agents Ent. Exp. Appl. 32 1982 299 301
37. Klocke, J.A., Balandrin, M.F., Barnby, M.A., Yamasaki, R.B., 1989. Limonoids, phenolics, and furanocoumarins as insect antifeedants, repellents and growth inhibitory compounds. In: Arnason, J.T., Philogène, B.J.R., Morand, P. (Eds.), Insecticides of Plant Origin. ACS Symposium Series, vol. 387, pp. 136-149.
38. J.C. Knight, D.I. Wilkinson, and C. Djerassi Structure of the cactus sterol macdougallin (14α-methyl-8-cholestene-3β,6α-diol). A novel link in sterol biogenesis J. Am. Chem. Soc. 88 4 1966 790 798
39. J.C. Knight, and G.R. Pettit Arizona flora: the sterols of Peniocereus greggii Phytochemistry 8 1969 477 482
40. K.L. Korth, and R.A. Dixon Evidence for chewing insect-specific molecular event distinct from a general wound response in leaves Plant Physiol. 115 1997 1299 1305
41. I. Kubo Tyrosinase inhibitors from plants Rev. Latinoamér. Quím. 28 2000 7 20
42. I. Kubo, J.A. Klocke, and S. Asano Insect ecdysis inhibitors from the East African medicinal plant, Ajuga remota (Labiatae) Agric. Biol. Chem. 45 1981 1925 1927
43. I. Kubo, and J.A. Klocke Azadirachtin, insect ecdysis inhibitor Agric. Biol. Chem. 46 1982 1951 1953
44. I. Kubo, and J.A. Klocke An insect growth inhibitor from Trichilia roka (Meliaceae) Experientia 38 1982 639 640
45. I. Kubo, J.A. Klocke, and S. Asano Effects of ingested phytoecdysones on the growth and development of two lepidopterous larvae J. Insect Physiol. 29 1983 307 316
46. I. Kubo, and J.A. Klocke Isolation of phytoecdysones as insect ecdysis inhibitors and feeding deterrents P.A. Hedin Plant Resistance to Insects. ACS Symposium Series vol. 208 1983 American Chemical Society Washington, DC 329 346
47. I. Kubo, A. Matsumoto, T. Matsumoto, and J.A. Klocke New insect ecdisis inhibitory limonoid deacetylazadirachtinol isolated from Azadirachta indica (Meliaceae) oil Tetrahedron 42 1986 489 496
48. I. Kubo, S. Komatsu, Y. Asaka, and G. De Boer Isolation and identification of apolar metabolites of ingested 20-hydroxyecdysone in frass of Heliothis virescens larvae J. Chem. Ecol. 13 1987 785 794
49. I. Kubo Tyrosinase inhibitors from plants P. Hedin R. Hollingworth E. Masler J. Miyamoto D. Thompson Phytochemicals for Pest Control ACS Symposium Series vol. 685 1997 American Chemical Society Washington, DC 311 326
50. I. Kubo, and I. Kinst-Hori Flavonols from saffron flowers: tyrosinase inhibitory activity and inhibition mechanism J. Agric. Food. Chem. 47 10 1999 4121 4125
51. I. Kubo, I. Kinst-Hori, S.K. Chauduri, Y. Kubo, Y. Sánchez, and T. Ogura Flavonols from Heterotheca inuloides: tyrosinase inhibitory activity and structural criteria Bioorg. Med. Chem. 8 2000 1749 1755
52. I. Kubo, Q.-X. Chen, K.I. Nihei, J.S. Calderon, and C.L. Céspedes Tyrosinase inhibition kinetics of anisic acid Z. Naturforsch. c 58 2003 713 718
53. I. Kubo, I. Kinst-Hori, K.I. Nihei, F. Soria, M. Takasaki, J.S. Calderón, and C.L. Céspedes Tyrosinase inhibitors from Galls of Rhus javanica leaves and their effects on insects Z. Naturforsch. c 58 2003 719 725
54. F. Marion-Poll, and C. Descoins Taste detection of phytoecdysteroids in larvae of Bombyx mori, Spodoptera littoralis and Ostrinia nubilalis J. Insect Physiol. 48 2002 467 476
55. E.P. Marks Insect tissue culture: an overview, 1971-1978 Annu. Rev. Entomol. 25 1980 73 101
56. W. Meyer, H. Jungnickel, M. Jandke, K. Dettner, and G. Spiteller On the cytotoxity of oxidized phytosterols isolated from photoautotrophic cell cultures of Chenopodium rubrum tested on meal-worms Tenebrio molitor Phytochemistry 47 5 1998 789 797
57. J.A. Mihm Mass rearing stem borers, fall armyworms and corn earworms at CIMMYT Toward Insect Resistant Maize for the Third World Proceedings of the International Symposium on Methodologies for Developing Host Plant Resistance to Maize 1987 CIMMYT Mexico 5 21
58. D.H. Miles, K. Tunsuwan, V. Chittawong, P.A. Hedin, and U. Kokpol Boll weevil antifeedants from Eleocharis dulcis Trin J. Agric. Food Chem. 42 7 1994 1561 1562
59. M. Panzuto, Y. Mauffette, and P.J. Albert Developmental, gustatory, and behavioral responses of leaf roller larvae, Choristoneura rosaceana, to tannic acid and glucose J. Chem. Ecol. 28 2002 145 160
60. D.F. Rhoades Evolution of plant chemical defense against herbivores G.A. Rosenthal D.H. Janzen Herbivores: Their Interactions with Secondary Plant Metabolites 1979 Academic Press New York 3 54
61. D.F. Rhoades, and R.G. Cates Toward a general theory of plant antiherbivore chemistry Recent Adv. Phytochem. 10 1976 168 213
62. E. Sáez, M.C. Nelson, B. Eshelman, E. Banayo, A. Koder, G.J. Cho, and R.M. Evans Proc. Natl. Acad. Sci. USA 97 26 2000 14512 14517
63. A. Sandoval, A. Manjarrez, P.R. Leeming, G.H. Thomas, and C. Djerassi Terpenoids. XXX. The structure of the cactus triterpene chichipegenin J. Am. Chem. Soc. 79 1957 4468 4472
64. T. Savchenko, P. Whiting, A. Germade, and L. Dinan Ecdysteroid agonist and antagonist activities in species of the Solanaceae Biochem. Syst. Ecol. 28 2000 403 419
65. E.A. Schmelz, R.J. Grebenok, D.W. Galbraith, and W.S. Bowers Insect-induced synthesis of phytoecdysteroids in spinach, Spinacia oleracea J. Chem. Ecol. 25 1999 1739 1757
66. P. Simon, and J. Koolman Ecdysteroids in vertebrates: pharmacological aspects J. Koolman Ecdysone: From Chemistry to Mode of Action 1989 George Thieme-Verlag Stuttgart 254 259
67. K. Sláma, and R. Lafont Insect-hormones - ecdysteroids: their presence and actions in vertebrates Eur. J. Entomol. 92 1995 355 377
68. T. Swain Tannins and lignins G.A. Rosenthal D.H. Janzen Herbivores: Their Interactions with Secondary Plant Metabolites 1979 Academic Press New York 657 682
69. M.C. Tamayo, M. Rufat, J.M. Bravo, and B. San Segundo Accumulation of a maize proteinase inhibitor in response to wounding and insect feeding, and characterization of its activity toward digestive proteinases of Spodoptera littoralis larvae Planta 211 2000 62 71
70. F. Taýbi, G. Smagghe, L. Amrani, and N. Soltani-Mazouni Effect of ecdysone agonist RH-0345 on reproduction of mealworm, Tenebrio molitor Comp. Biochem. Physiol. C 135c 3 2003 257 267
71. P. Torres, J.G. Avila, A. Romo de Vivar, A.M. GarcIÍa, J.C. MarIÍn, E. Aranda, and C.L. Céspedes Antioxidant and insect growth regulatory activities of stilbenes and extracts from Yucca periculosa Phytochemistry 64 2003 463 473
72. J.W. Truman, D.B. Rountree, S.E. Reiss, and L.M. Schwartz Ecdysteroids regulate the release and action of eclosion hormone in the tobacco hornworm, Manduca sexta (L.) J. Insect Physiol. 29 1983 895 900
73. J.W. Truman, and L.M. Riddiford Endocrine insights into the evolution of the metamorphosis in insects Annu. Rev. Entomol. 47 2002 467 500
74. M. Zhang, M.J. Stout, and I. Kubo Isolation of ecdysteroids from Vitex stricheri using RLCC and recycling HPLC Phytochemistry 31 1992 247 250
75. M. Zhang, S.K. Chaudhuri, and I. Kubo Quantification of insect growth and its use in screening of naturally occurring insect control agents J. Chem. Ecol. 19 1993 1109 1118
76. D. Zitnan, T.G. Kingan, J.L. Hermesman, and M.E. Adams Identification of ecdysistriggering hormone from an epitracheal endocrine system Science 271 1996 88 91
77. D. Zitnan, L.S. Ross, I. Zitnanova, J.L. Hermesmann, S.S. Gill, and M.E. Adams Steroid induction of a peptide hormone gene leads to orchestration of a defined behavioral sequence Neuron 23 1999 523 535