Mode of inhibition of acetylcholinesterase by monoterpenoids and implications for pest control

Industrial Crops and Products

Volumn 31, Issue 2, 2010, Pages 284-288

  Lopez M D ^a   Pascual Villalobos, M J ^a  

^a INSTITUTO MURCIANO DE INVESTIGACIÓN Y DESARROLLO AGRARIO Y ALIMENTARIO IMIDA   (Spain)

Author keywords

Acetylcholinesterase; Competitive inhibition; Cryptolestes pusillus; Fenchone; Linalool; Mixed inhibition; Monoterpenoids; Rhyzopertha dominica; S carvone; Sitophilus oryzae

Indexed keywords

ACETYLCHOLINESTERASE; CARVONE; COMPETITIVE INHIBITION; FENCHONE; MONOTERPENOIDS; RHYZOPERTHA DOMINICA; SITOPHILUS ORYZAE;

CHEMICAL REACTIONS; ENZYMES; INSECT CONTROL; SULFUR COMPOUNDS; UNSATURATED COMPOUNDS;

ENZYME INHIBITION;

BEETLE; COLORIMETRY; ENZYME ACTIVITY; ESTROGENIC COMPOUND; HYDROPHOBICITY; INHIBITION; INSECTICIDE; MORTALITY; PEST CONTROL; TERPENE;

BOSTRICHIDAE; COLEOPTERA; CRYPTOLESTES PUSILLUS; CUCUJIDAE; CURCULIONIDAE; DRYOBALANOPS; HEXAPODA; RHYZOPERTHA DOMINICA; SITOPHILUS ORYZAE;

ENZYME; HYDROPHOBIC PROPERTY; INHIBITOR; INSECT RESISTANCE; PEST CONTROL; SUBSTRATE;

EID: 76449093738     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2009.11.005     Document Type: Article

References (34)

1. Abdelgaleil S.A.M., Mohamed M.I.E., Badawy M.E.I., and El-arami S.A.A. Fumigant and contact toxicities of monoterpenes to Sitophilus oryzae (L.) and Tribolium castaneum (Herbst) and their inhibitory effects on acetylcholinesterase activity. J. Chem. Ecol. 35 (2009) 518-525
2. Alvarez-Castellanos P., Bishop C.D., and Pascual-Villalobos M.J. Antifungal activity of the essential oil of flowerheads of garland chrysanthemum (Chrysanthemum coronarium) against agricultural pathogens. Phytochemistry 57 (2001) 99-102
3. Cabezas-Herrera J., Campoy F.J., and Vidal C. Differential effects of ethanol on membrana-bound and soluble acetylcholinesterase from sarcoplasm reticulum membranes. Neurochem. Res. 17 (1992) 717-722
4. Don-Pedro K.N. Fumigant toxicity is the major route of insecticidal activity of citruspeel essential oils. Pestic. Sci. 46 (1996) 71-78
5. Ellman G.L., Courtney K.D., Valentino A.J., and Featherstone R.M. A new and rapid colorometric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7 (1961) 88-95
6. Fournier D., Cuany A., Bride J.M., and Berge J.B. Molecular polymorphism of head acetylcholinesterase from adult houseflies (Musca domestica L.). J. Neurochem. 49 (1987) 1455-1461
7. García M., Donadel O.J., Ardanaz C.E., Tonn C.E., and Sosa M.E. Toxic and repellent effects of Baccharis salicifolia essential oil on Tribulium castaneum. Pest Manag. Sci. 61 (2005) 612-618
8. Grundy D.L., and Still C.C. Inhibition of acetylcholinesterase by pulegone-1,2-epoxide. Pestic. Biochem. Physiol. 23 (1985) 383-388
9. Hideyuki T., and Mitsuo M. Inhibition of acetylcholinesterase activity by essential oil from Bergamot. Koryo Terupen oyobi Seiyu Kagaku ni Kansuru Toronkai Koen Yoshishu 45 (2001) 435-436
10. Houghton P.J., Ren Y., and Howes M.J. Acetylcholinesterase inhibitors from plants and fungi. Nat. Prod. Rep. 23 (2006) 186-199
11. Isman M.B. Plant essential oils for pest and disease management. Crop Protect. 19 (2000) 603-608
12. Jukic M., Politeo O., Maksimovic M., Milos M., and Milos M. In Vitro acetylcholinesterase inhibitory properties of thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone. Phytotherapy Res. 21 (2007) 259-261
13. Keane S., and Ryan M.F. Purification, characterisation, and inhibition by monoterpenes of acetylcholinesterase from the waxmoth, Galleria mellonella (L.). Insect Biochem. Mol. Biol. 29 (1999) 1097-1104
14. Kostyukovsky M., Rafaeli A., Gileadi C., Demchenko N., and Shaaya E. Activation of octopaminergic receptors by essential oil constituents isolated from aromatic plants: possible mode of action against insect pests. Pest Manag. Sci. 58 (2002) 1101-1106
15. Lee S.E., Lee B.H., Choi W.S., Park B.S., Kim J.G., and Campbell B.C. Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L). Pest Manag. Sci. 57 (2001) 548-553
16. Lee S., Peterson C.J., and Coats J.R. Fumigation toxicity of monoterpenoids to several stored product insects. J. Stored Prod. Res. 39 (2003) 77-85
17. López M.D., Jordan M.J., and Pascual-Villalobos M.J. Toxic compounds in essential oils of coriander, caraway and basil against stored rice pests. J. Stored Prod. Res. 44 (2008) 273-278
18. López, M.D., Pascual-Villalobos, M.J., 2008. Insecticidal activity of volatile monoterpenoids to Sitophilus oryzae L. (Coleoptera: Curculionidae), Rhyzopertha dominica Fabricius (Coleoptera: Bostrichidae) and Cryptolestes pusillus Schönherr (Coleoptera: Cucujidae). Bulletins Working Group "Integrated Protection of Stored Products". In: Shlomo, N., Cornel, A., Lise Stengard H., (Eds.), Proceedings of the Meeting at Poznan (Poland), 20-23 August, 2007. ISBN 978-92-9067-214-2. IOBC/wprs Bull., 40: 211-219.
19. Miyazawa M., Watanabe H., and Kameoka H. Inhibition of acetylchoinesterase activity by monoterpenoids with a p-menthane skeleton. J. Agric. Food Chem. 45 (1997) 677-679
20. Ngoh S.P., Choo L.E.W., Pang F.Y., Huang Y., Kini M.R., and Ho S.H. Insecticidal and repellent properties of nine volatile constituents of essential oils against the American cockroach, Periplaneta americana (L.). Pestic. Sci. 54 (1998) 261-268
21. Obeng-Ofori D., Reichmuth C.H., Bekele A.J., and Hassanali A. Toxicity and protectant potential of camphor, a major component of essential oil of Ocimum kilimandscharicum, against four stored product beetles. J. Pest Manag. 44 (1998) 203-209
22. Pascual-Villalobos M.J., and Ballesta-Acosta M.C. Chemical variation in an Ocimum basilicum germplasm collection and activity of the essential oils on Callosobruchus maculatus. Biochem. Systemat. Ecol. 31 (2003) 673-679
23. Pascual-Villalobos M.J., Ballesta-Acosta M.C., and Soler A. Toxicidad y repelencia de aceites esenciales en plagas de almacén del arroz. Bol. San. Veg. Plagas 30 (2004) 279-286
24. Picollo M.I., Toloza A.C., Mougabure Cueto G., Zygadlo J., and Zerba E. Anticholinesterase and pediculicidal activities of monoterpenoids. Fitoterapia 79 (2008) 271-278
25. Rajendran S., and Sriranjini V. Plant products as fumigants for stored-product insect control. J. Stored Prod. Res. 44 (2008) 126-135
26. Regnault-Roger C., and Hamraoui A. Inhibition of reproduction of Acanthoscelides obtectus Say (Coleoptera), a kidney bean (Phaseolu vulgaris) bruchid, by aromatic essential oils. Crop Protect. 13 (1994) 624-628
27. Regnault-Roger C., and Hamraoui A. Fumigant toxic activity and reproductive inhibition induced by monoterpenes on Acanthoscelides obtectus (Say)(Coleoptera), a bruchid of kidney bean (Phaseolus vulgaris L.). J. Stored Prod. Res. 31 (1995) 291-299
28. Ryan M.F., Awde J., and Moran S. Insect pheromones as reversible competitive inhibitors of acetylcholinesterase. Invertebrate Reprod. Develop. 22 (1992) 31-38
29. Ryan M.F., and Byrne O. Plant-insect coevolution and inhibition of acetylcholinesterase. J. Chem. Ecol. 14 (1988) 1965-1975
30. Savelev S., Okello E., Perry N.S.L., Wilkins R.M., and Perry E.K. Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil. Pharmacol. Biochem. Behav. 75 (2003) 661-668
31. Siegfried B.D., and Scott S.C. Biochemical characterization of hydrolytic and oxidative enzyme in insecticide resistant and susceptible strain of the German cockroach (Dictyoptera: Blattellidae). J. Econ. Entomol. 85 (1990) 1092-1098
32. Sima H., Greenberg-Levy M., Kostjukovsky U., Ravid E., and Shaaya E. Studies to elucidate the effect of monoterpenes on acetylcholinesterase in two stored-product insects. Act. Hortic. 344 (1993) 138-146
33. Zhu K.Y., and Brindley W.A. Molecular properties of acetylcholinesterase purified from Lygus hesperus Knight (Hemiptera: Miridae). Insect Biochem. Molec. Biol. 22 3 (1992) 253-260
34. Zhu K.Y., and Clark M. Purification and characterisation of acetylcholinesterase from the Colorado Potato Beetle Leptinotarsa decemlineata (Say). Insect Biochem. Molec. Biol. 24 5 (1994) 453-461