Allelochemical effects of eudesmane and eremophilane sesquiterpenes on Tribolium castaneum larvae

Journal of Chemical Ecology

Volumn 29, Issue 1, 2003, Pages 175-187

  García, Matías ^a   Sosa, Marta E ^a   Donadel, Osvaldo J ^a   Giordano, Oscar S ^a   Tonn, Carlos E ^a  

^a UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

Author keywords

3 oxo costic acid; Allelochemical effects; Eremophilanes; Eudesmanes; Ilicic acid; Sesquiterpenes; Tessaria absinthioides; Tessaric acid; Tribolium castaneum

Indexed keywords

EREMOPHILANE DERIVATIVE; EUDESMANE DERIVATIVE; SESQUITERPENE;

ALLELOCHEMICAL; CHEMICAL ECOLOGY; LARVA;

ARTICLE; CHEMICAL ANALYSIS; DEFORMITY; INSECTICIDAL ACTIVITY; LARVA; LARVAL DEVELOPMENT; NONHUMAN; PHYTOCHEMISTRY; TRIBOLIUM;

ADMINISTRATION, TOPICAL; ANIMALS; BIOLOGICAL ASSAY; CHEMORECEPTORS; LARVA; MOVEMENT; NAPHTHALENES; SESQUITERPENES; SESQUITERPENES, EUDESMANE; TRIBOLIUM;

COLEOPTERA; HEXAPODA; TENEBRIONIDAE; TRIBOLIUM CASTANEUM;

EID: 12244298926     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021988816329     Document Type: Article

References (31)

1. ALFATAFTA, A. A. and MULLIN, C. A. 1992. Epicuticular terpenoids and an aurone from flowers of Helianthus annuus. Phytochemistry 31:4109-4113.
2. ARNASON, J. T., PHILOGÉNE, B. J. R., BERG, C., MACEACHERN, A., KAMINSKI, J., LEITCH, L. C., MORAND, P., and LAM, J. 1986. Phototoxicity of naturally occurring and synthetic thiophene and acetylene analogues to mosquito larvae. Phytochemistry 25:1609-1611.
3. BOWERS, W. S. and THOMPSON, M. J. 1963. Juvenile hormone activity: effects of isoprenoid and straigth-chain alcohols on insects. Science 142:1469-1470.
4. BROWN, H. C. and KRISHNAMURTHY, S. 1979. Forty years of hydride reductions. Tetrahedron 35:567-607.
5. CARRIZO, F. R., SOSA, M. E., FAVIER, L. S., PENNA, F., GUERREIRO, E., GIORDANO, O. S., and TONN, C. E. 1998. Growth-inhibitory activities of benzofuran and chromene derivates toward Tenebrio molitor L. J. Nat. Prod. 61:1209-1211.
6. CHOU, J. and MULLIN, C. A. 1993. Distribution and antifeedant associations of sesquiterpene lactones in cultivated sunflower (Helianthus annus L.) on western corn rootworm (Diabrotica virgifera virgifera LeConte). J. Chem. Ecol. 19:1439-1452.
7. DONADEL, O. J., GARCíA, E. E., GUERREIRO, E., and TONN, C. E. 1998. Easy preparation of Bioactives eudesman-12(5β)-olide derivatives from ilicic acid. Anales Asoc. Quím. Argent. 86:90-93.
8. ENRIZ, R. D., BALDONI, H., JÁUREGUI, E., SOSA, M. E., TONN, C. E., and GIORDANO, O. 1994. Structure activity relationships of clerodane diterpenoids acting as antifeedant agents. J. Agric. Food. Chem. 42:2958-2963.
9. ENRIZ, R. D., BALDONI, H., ZAMORA, M. A., SOSA, M. E., TONN, C. E., LUCO, J. M., and GORDALIZA, M. J. 2000. Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin. J. Agric. Food. Chem. 48:1384-1392.
10. GERSHENZON, J. and CROTEAU, R. 1999. Terpenoids. pp. 165-170, in G. A. Rosenthal, and M. R. Berenbaum (eds.). Herbivores: Their Interactions with Secondary Plant Metabolites, Vol. 1. Academic Press, San Diego, California.
11. GUERREIRO, E., KAVKA, J., GIORDANO, O. S., and GROS, E. 1979. Sesquiterpenoids and flavonoids form Flourensia oolepis. Phytochemistry 18:1235-1237.
12. HARMATHA, J. and NAWROT, J. 1984. Comparison of the feeding deterrent activity of some sesquiterpene lactones and a lignan lactone towards selected insect storage pests. Biochem. Syst. Ecol. 12:95-98.
13. HENDERSON, C. F. and TILTON, F. 1985. Test with acaricides against the brown wheat mite. J. Econ. Entomol. 48:157-161.
14. ISMAN, M. B. 2000. Plant essential oils for pest and disease management. Crop Protect. 19:603-608.
15. ISMAN, M. B., and RODRIGUEZ, E. 1983. Larval growth inhibitors from species of Parthenium (Asteraceae). Phytochemistry 22:2709-2713.
16. KURINA SANZ, M. B., DONADEL, O. J., ROSSOMANDO, P. C., TONN, C. E., and GUERREIRO, E. 1997. Sesquiterpenes from Tessaria absinthioides. Phytochemistry 44:897-900.
17. LOW, P. F., DAVEY, B. G., LEE, K. W., and BAKER, D. E. 1968. Juvenile hormone: Activity of natural and synthetic synergists. Science 161:895-897.
18. LUCO, J. C., SOSA, M. E., CESCO, J. C., TONN, C. E., and GIORDANO, O. 1994. Molecular connectivity and hydrophobicity in the study of antifeedant activity of clerodane diterpenoids. Pestic. Sci. 41:1-6.
19. OBENG-OFORI, D. and REICHMUTH, C. H. 1997. Bioactivity of eugenol, a major component of essential oil of Ocimum suave (Wild.) against four species of stored-product Coleoptera. Int. J. Pest Manage. 43:89-94.
20. PASCUAL, N. MARCO, M. P., and BELLÉS, X. 1990. Azadirachtin induced imaginal moult deficiencies in Tenebrio molitor L. (Coleoptera: Tenebrionidae). J. Stored Prod. Res. 26:53-57.
21. PHILLIPS, T. W. 1994. Pheromones of stored-products insects: current status and future perspectives, pp. 479-486, in E. Highley, E. J. Wright, H. J. Banks and B. R. Champ (ed.). Stored Product Protection. Proceeding of the 6th International Working Conference on Stored-product Protection Volume 1. University Press. Cambridge.
22. PHILLIPS, T. W., JIANG, X. L., BURKHOLDER, W. E., PHILLIPS, J. K., and TRAN, H. Q. 1993. Behavioral responses to food volatiles by two species of stored-product coleoptera, Sitophilus oryzae (Curculionidae) and Tribolium castaneum (Tenebrionidae). J. Chem. Ecol. 19:723-733.
23. PICMAN, K. A. 1986. Biological activities of sesquiterpene lactones. Biochem. Syst. Ecol. 14:255-281.
24. QUENNEDEY, A. 1998. Insect epidermal glands cells: ultrastructure and morphogenesis, pp. 177-207 in F. W. Harrison and M. Locke (eds.). Microscopic Anatomy of Invertebrates. Section II. Vol. 11. A. John Wiley and Sons, Inc. New York.
25. SAKUMA, M. 1998. Probit analysis of preference data. Appl. Entomol. Zool. 33:339-347.
26. SCHOONHOVEN, L. M. and FU-SHUN, Y. 1989. Interference with normal chemoreceptor activity by some sesquiterpenoid antifeedants in an herbivorous insects Pieris brassicae. J. Insect Physiol. 35:725-728.
27. SOSA, M. E., TONN, C. E., and GIORDANO, O. S. 1994. Insect antifeedant activity of clerodanes diterpenoids. J. Nat. Prod. 57:1262-1265.
28. SRIVASTARA, R. P., PROKSCH, P., and WRAY, V. 1990. Toxicity and antifeedant activity of a sesquiterpene lactone from Encelia sp. against Spodoptera littoralis. Phytochemistry 29:3445-3448.
29. THOMPSON, M. J. and UEBEL, E. C. 1966. Juvenile hormone: identification of an active compound from balsam fir. Science 154:1020-1021.
30. TSAO, R., REUBER, M., JOHNSON, L., and COATS, J. R. 1996. Insecticidal toxicities of glucosinolate-containing extracts from crambe seeds. J. Agric. Entomol. 13:109-120.
31. WOOD, E., CASABÉ, N., MELGAR, F., and ZERBA, E. 1986. Distribution and properties of glutathione-S-trasnferase from Triatoma infestans. Comp. Biochem. Physiol. 84: 607-618.