Antifeedant and phytotoxic activity of the sesquiterpene p-benzoquinone perezone and some of its derivatives

Journal of Chemical Ecology

Volumn 34, Issue 6, 2008, Pages 766-771

  Burgueño Tapia, Eleuterio ^a   Castillo, Lucia ^b   González Coloma, Azucena ^b   Joseph Nathan, Pedro ^c  

^a INSTITUTO POLITÉCNICO NACIONAL   (Mexico)

^b INSTITUTO DE CIENCIAS AGRARIAS   (Spain)

^c DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

Antifeedant; Isoperezone; Perezone; Phytotoxicity

Indexed keywords

PEREZONE; SESQUITERPENE;

ANTIFEEDANT; GROWTH RESPONSE; HERB; HERBIVORE; INHIBITION; LEAFY VEGETABLE; PHYTOTOXICITY; TERPENE; TESTING METHOD;

ANIMAL; ARTICLE; BIOMASS; CHEMISTRY; DRUG EFFECT; EATING; GROWTH, DEVELOPMENT AND AGING; INSECT; ISOLATION AND PURIFICATION; LARVA; LETTUCE; PHYSIOLOGY;

ANIMALS; BIOMASS; EATING; INSECTS; LARVA; LETTUCE; SESQUITERPENES;

ASTERACEAE; HEXAPODA; LACTUCA; LACTUCA SATIVA; LEPTINOTARSA DECEMLINEATA; MYZUS PERSICAE; PEREZIA; SPODOPTERA LITTORALIS;

EID: 45849137822     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-008-9495-2     Document Type: Article

References (40)

1. Alarcón-Aguilar, F. J., Román-Ramos, R., Jiménez-Estrada, M., Reyes-Chilpa, R., González-Paredes, B., and Flores-Sáenz, J. L. 1997. Effects of three Mexican medicinal plants (Asteraceae) on blood glucose levels in healthy mice and rabbits. J. Ethnopharmacol 55:171-177.
2. Archer, D. A., and Thomson, R. H. 1965. The structure of perezone. Chem. Comm. 14: 354-355.
3. Barbosa, L. C. A., Ferreira, M. L., and Demuner, A. J. 2001. Preparation and phytotoxicity of sorgoleone analogues. Quím. Nova. 24:751-755.
4. Bates, R. B., Paknikar, S. K., and Thalacker, V. P. 1965. A 1,3-addition by a hydroxyquinone: The structure of perezone. Chem. & Ind.1793.
5. Burgueño-Tapia, E., and Joseph-Nathan, P. 1997. Detailed studies of perezone rearrangements. Monatsh. Chem. 128:651-658.
6. 13C NMR substituent chemical shifts in hydroxy-p-benzoquinones. Magn. Reson. Chem. 38:390-393.
7. Burgueño-Tapia, E., González-Coloma, A., Martín-Benito, D., and Joseph-Nathan, P. 2007. Antifeedant and phytotoxic activity of cacalolides and eremophilanolides. Z. Naturforsch. 6c2:362-366.
8. Burgueño-Tapia, E., González-Coloma, A., Castillo, L., and Joseph-Nathan, P 2008. Antifeedant and phytotoxic activity of hydroxyperezone and related molecules. Z. Naturforsch 63c:221-225.
9. Carabez, A., and Sandoval, F. 1988. The action of the sesquiterpenic benzoquinone perezone on electron-transport in biological membranes. Arch. Biochem. Biophys. 260:293-300.
10. 2+ releasing effects of perezone on adrenal cortex mitochondria. Life Sci. 41:2047-2054.
11. De la peña, A., Izaguirre, R., Baños, G., Viveros, M., Enríquez, R. G., and Fernández-g, J. M. 2001. Effect of perezone, aminoperezone and their corresponding isomers isoperezone and isoaminoperezone upon in vitro platelet aggregation. Phytomedicine. 8:465-468.
12. Enríquez, R., Ortega, J., and Lozoya, X. 1980. Active components in Perezia roots. J. Ethnopharmacol. 2:389-393.
13. García, X., Alcántara-Sarabia, G., Cartas-Heredia, L., and Gijón, E. 1995. Actions of perezone on rat smooth muscle. Gen. Pharmacol. 26:1741-1745.
14. González-Coloma, A., Gutiérrez, C., Hübner, H., Achenbach, H., Terrero, D., and Fraga, B. M. 1999. Selective insect antifeedant and toxic action of ryanoid diterpenes. J. Agric. Food Chem. 47:4419-4424.
15. González-Coloma, A., Guadaño, A., De inés, C., Martínez-Diaz, R., and Cortes, D. 2002a. Selective action of acetogenin mitochondrial Complex I inhibitors. Z. Naturforsch. 57c:1028-1034.
16. González-Coloma, A., Valencia, F., Martín, N., Hoffmann, J. J., Hutter, L., Marco, J. a., and Reina, m. 2002b. Silphinene sesquiterpenes as model insect antifeedants. J. Chem. Ecol. 28:117-129.
17. González-Coloma, A., Guadano, A., Tonn, C. E., and Sosa, M. E. 2005. Antifeedant/insecticidal terpenes from Asteraceae and Labiatae species native to Argentinean semi-arid lands. Z. Naturforsch. 60c:855-861.
18. Gutiérrez, C., Fereres, A., Reina, M., Cabrera, R., and González-coloma, A. 1997. Behavioral and sub-lethal effects of structurally-related lower terpenes on Myzus persicae. J. Chem. Ecol. 23:1641-1650.
19. Hausen, B. M., and Soriano-García, M. 1987. The sensitizing capacity of perezone. Contact Dermatitis. 17:259-260.
20. Hejl, A. M., Einhellig, F. A., and Rasmussen, J. A. 1993. Effects of juglone on growth, photosynthesis and respiration. J. Chem. Ecol. 19:559-568.
21. Hejl, A. M., and Koster, K. L. 2004. The allelochemicals sorgoleone inhibits root H+-ATPase and water uptake. J. Chem. Ecol. 30:2181-2191.
22. Horton, R. D., and Redak, R. A. 1993. Further comments on analysis of covariance in insect dietary studies. Entomol. Exp. Appl. 69:263-275.
23. Joseph-Nathan, P., and Santillan, R. L. 1989. The chemistry of perezone and its consequences, pp. 763-813, in Atta-ur-Rahman (ed.). Studies in Natural Products Chemistry, Vol. 5 Structural Elucidation (Part B)Elsevier, Amsterdam.
24. Lima, L. S., Barbosa, L. C. A., De alverenga, E. S., Demuner, A. J., and Da silva, A. A. 2003. Synthesis and phytotoxicity evaluation of substituted para-benzoquinones. Aust. J. Chem. 56:625-630.
25. Marimoto, M., Tanimoto, K., Sakatani, A., and Komai, K. 2002. Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F. Phytochemistry. 60:163-166.
26. Moiteiro, C., Marcelo-Curto, M. J., Mohamed, N., Bailén, M., Martínez-Díaz, R., and González-Coloma, A. 2006. Biovalorization of friedelane triterpenes derived from the cork processing industry byproducts. J. Agric. Food. Chem. 54:3566-3571.
27. Moreno-Osorio, L., Cortes, M., Armstrong, V., Bailén, M., and González-Coloma, A. 2008. Antifeedant activity of some polygodial derivatives. Z. Naturforsch. 63c: in press.
28. Motti, C. A., Bourguet-Kondrcki, M.-L., Longeon, L., Doyle, J. R., Lleweling, L. E., Tapioles, D. M., and Ying, P. 2007. Comparison of the biological properties of several marine sponge-derived sesquiterpenoid quinones. Molecules. 12:1376-1388.
29. Poitout, S., and Bues, R. 1974. Elevage de plusiereurs espèces de lépidoptères Noctuidae sur milieu artificiel riche et sur milieu artificiel simplifié. Ann. Zool. Ecol. Anim. 2:79-91.
30. Raubenheimer, D., and Simpson, S. J. 1992. Analysis of covariance: an alternative to nutritional indices. Entomol. Exp. Appl. 62:221-231.
31. Reina, M., González-Coloma, A., Gutiérrez, C., Cabrera, R., Rodríguez, M. L., Fajardo, V., and Villarroel, L. 2001. Defensive chemistry of Senecio miser. J. Nat. Prod. 64:6-11.
32. Reina, M., González-Coloma, A., Domínguez-Díaz, D., Cabrera, R., Jiménez, M. C., Rodríguez, M. L., and Villarroel, L. 2006. Bioactive eremophilanolides from Senecio poepigii. Nat. Prod. Res. 20:13-19.
33. Río de la loza, L. Discurso pronunciado por el catedrático de Química Médica de la Escuela de Medicina (November 23th, 1852), pp. 94-100, in Escritos de Leopoldo Río de la Loza, compiled by J. M. Noriega,. Imprenta de Ignacio Escalante, México (1911).
34. Rodríguez-Hernández, A., Barrios, H., Collera, O., Enríquez, R. G., Ortiz, B., Sánchez-Obregón, R., Walls, F., Yuste, F., Reynolds, W. F., and Yu, M. 1994. Isomerization of perezone into isoperezone and preparation of dihydroisoperezinone. Nat. Prod. Lett. 4:133-139.
35. Roura-Pérez, G., Quiroz, B., Aguilar-Martínez, M., Frontana, C., Solano, A., González, I., Bautista-Martínez, J. A., Jiménez-Barbero, J., and Cuevas, G. 2007. Remote position substituents as modulators of conformational and reactive properties of quinones. Relevance of the π/π intramolecular interaction. J. Org. Chem. 72:1883-1894.
36. Téllez, J. F., Carvajal, K., Cruz, D., Carabez, A., and Chávez, E. 1999. Effect of perezone on arrythmias and markers of cell injury during reperfusion in the anesthetized rat. Life Sci. 16:1615-1623.
37. Wagner, E. R., Moss, R. D., Brooker, R. M., Heeschen, J. P., Potts, W. J., and Dilling, M. 1965. A correction of the structure of perezone. Tetrahedron Lett 4233-4239.
38. Walls, F., Padilla, J., Joseph-Nathan, P., Giral, F., and Romo, J. 1965a. The structures of - and -pipitzols. Tetrahedron Lett. 1577-1582.
39. Walls, F., Salmón, M., Padilla, J., Joseph-Nathan, P., and Romo, J. 1965b. La estructura de la perezona. Bol. Inst. Quím. Univ. Nal. Autón. Méx. 17:3-15.
40. Wellsow, J., Grayer, R. J., Veitch, N. C., Kokubun, T., Lelli, R., Kite, G. C., and Simmonds, M. S. J. 2006. Insect-antifeedant and antibacterial activity of diterpenoids from species of Plectranthus. Phytochemistry. 67:1818-1825.