Quantitative structure-activity relationship of terpenoid aphid antifeedants

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 23, 2008, Pages 11361-11366

  Wang, Zongde ^a   Song, Jie ^b   Han, Zhaojiu ^c   Jiang, Zhikuan ^c   Zheng, Weiqing ^a   Chen, Jinzhu ^a   Song, Zhanqian ^d   Shang, Shibin ^d  

^a JIANGXI AGRICULTURAL UNIVERSITY   (China)

^b UNIVERSITY OF MICHIGAN FLINT   (United States)

^c Nanjing Military Medical Institute   (China)

^d RESEARCH INSTITUTE OF FORESTRY   (China)

Author keywords

Antifeedant activity; Best multilinear regression; Heuristic regression; Lipaphis erysimi; QSAR; Stepwise regression; Terpenoid compound

Indexed keywords

INSECT REPELLENT; TERPENE;

ANIMAL; APHID; ARTICLE; CHEMISTRY; DRUG EFFECT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; APHIDS; INSECT REPELLENTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TERPENES;

APHIDIDAE; LIPAPHIS ERYSIMI;

EID: 58949091435     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf802324v     Document Type: Article

References (44)

1. Isman, M. Insect antifeedants. Pestic. Outlook 2002, 13, 152-157.
2. Simmonds, M. S. J. Chemoecology. The legacy left by Tony Swain. Phytochemistry 1998, 49, 1183-190.
3. Isman, M. B.; Matsuura, H.; MacKinnon, S.; Durst, T.; Towers, G. H. N.; Arnason, J. T. Phytochemistry of the Meliaceae: So many terpenoids, so few insecticides. Recent Adv. Phytochem. 1996, 30, 155-178.
4. Zhang, W.; Lou, H. Natural antifeedants from plant species. Curr. Top. Phytochem. 2000, 4, 147-167.
5. Josep, C.; Yudelsy, T. Isolation and identification of neo-clerodane diterpenes from ajuga remota by high-performance liquid chromatography. Phytochem. Anal. 2005, 16, 61-67.
6. Satdive, R. K.; Fulzele, D. P.; Eapen, S. Enhanced production of azadirachtin.by hairy root cultures of Azadirachta indica A. Juss by elicitation and media optimization. J. Biotechnol. 2007, 128, 281-289.
7. Zhang, Z.; Liu, X.; Lou, Z.; Li, H.; Zhu, S.; Zou, F. The antifeedant activity of polygodial against aphids. Kunchong Xuebao 1993, 36, 172-176.
8. Neoliya, N. K.; Singh, D.; Sangwan, R. S. Azadirachtin-based insecticides induce alteration in Helicoverpa armigera Hub. head polypeptides. Curr. Sci. 2007, 92, 94-99.
9. Dhingra, S.; Sharma, D.; Walia, S.; Kumar, J.; Singh, G.; Singh, S.; Jayaraman, B.; Parmar, B. S. Field appraisal of stable neem pesticide tetrahydroazadirachtin-A against mustard aphid (Lipaphis erysimi). Ind. J. Agric. Sci 2006, 76, 111-113.
10. Kumar, S.; Singh, R. N. Effect of Omite and some other acaricides against the mites Tetranychus urticae Koch and T. neocaledonicus Andre on Okra and brinjal under field conditions in Varanasi, Uttar Pradesh. Pestology 2005, 29, 15-19.
11. Szczepanik, M.; Dams, I.; Wawrzenczyk, C. Feeding deterrent activity of terpenoid lactones with the p-methane system against the Colorado potato beetle (Coleoptera: Chrysomelidae). Environ. Entomol. 2005, 34, 1433-1440.
12. Paruch, E.; Ciunik, Z.; Nawrot, J.; Wawrzenczyk, C. Lactones. 9. Synthesis of terpenoid lactones-active insect antifeedants. J. Agric. Food Chem. 2000, 48, 4973-4977.
13. Wang, Z. Studies on synthesis and activity of terpenoid repellent compounds. Dissertation, Chinese Academy of Forestry, Beijing, 2005.
14. Mazoir, N.; Benharref, A.; Bailen, M.; Reina, M.; Gonzalez-Coloma, A. Bioactive triterpene derivatives from latex of two Euphorbia species. Phytochemistry 2008, 69, 1328-1338.
15. Roy, A.; Saraf, S. Limonoids: Overview of significant bioactive triterpenes distributed in plant kingdom. Biol. Pharm. Bull. 2006, 29, 191-201.
16. Sunnerheim, K.; Nordqvist, A.; Nordlander, G.; Borg-Karlson, A. K.; Unelius, C. R.; Bohman, B.; Nordenhem, H.; Hellqvist, C.; Karlen, A. Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach. J. Agric. Food Chem. 2007, 55, 9365-9372.
17. Enriz, R. D.; Baldoni, H. A.; Zamora, M. A.; Jáuregui, E. A.; Sosa, M. E.; Tonn, C. E.; Luco, J. M.; Gordaliza, M. Structure-antifeedant activity relationship of Clerodane Diterpenoids. Comparative study with Withanolides and Azadirachtin. J. Agric. Food Chem. 2000, 48, 1384-1392.
18. Schlyter, F.; Smitt, O.; Sjoedin, K.; Hoegberg, H.-E.; Loefqvist, J. Carvone and less volatile analogues as repellent and deterrent antifeedants against the pine weevi Hylobius abietis. J. Appl. Entomol. 2004, 128, 610-619.
19. Morimoto, M.; Fukumoto, H.; Nozoe, T.; Hagiwara, A.; Komai, K. Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae. J. Agric. Food Chem. 2007, 55, 700-705.
20. Baldoni, H. A.; Enriz, R. D.; Jauregui, E. A.; Csizmadia, I. G. A theoretical study on the conformations of azadirachtin. THEOCHEM 1996, 363, 167-178.
21. Oleiniczak, T.; Grabarczyk, M.; Nawrot, J.; Wawrzenczyk, C. Lactones 10. Hydroxy and acetoxy terpenoid lactones-synthetic insect feeding deterrents. Biotechnologia 2000, 3, 106-117.
22. Qian, X. Quantitative studies on structure-activity relationship of sulfonylurea and benzoylphenylurea type pesticides and their substituents' bioisosterism using synthons' activity contribution. J. Agric. Food Chem. 1999, 47, 4415-4418.
23. Katritsky A.;Karelson M.; Lobanov V. S.;Dennington R.; Keith T. CODESSA 2.7.10. Semichem, Inc., Shawnee, KS, 2004.
24. Wang, Z.; Chen, J.; Song, Z.; Jiang, Z.; Han, Z.; Chen, C. Studies on synthesis and repellent activity of 8-hydroxylcarveol and its derivatives. Chem. Ind. For. Prod. 2007, 27, 1-6.
25. Chen, J.; Xiao, Z.; Wang, Z. Synthesis of ester derivatives of 4-(1-methylethylene)-1-cyclohexenyl-1-ethanol. Jiangxi Nongye Daxue Xuebao 2006, 28, 953-955.
26. Wang, Z; Xiao, Z. Chen. Synthesis and identification of nopol and its derivative. Huaxue Shijie 2004, 45, 89-92.
27. Wang, Z.; Chen, J.; Song, Z.; Xiao, Z. 13C chemical shift analysis of nopyl formate and nopylmethyl ether. J. Fujian Agric. For. Univ. 2007, 36, 385-388.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao,O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev,O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski,V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.;Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision D.01, Gaussian, Inc.,Wallingford, CT, 2004.
29. SciFinder Scholar, American Chemical Society, Wahsington, DC, 2008.
30. Morrison, D. F. Applied linear statistical methods; Prentice-Hall: Englewood Cliffs, NJ, 1983; pp 485-487.
31. Katritzky, A. R.; Dobchev, D. A.; Tulp, I.; Karelson, M.; Carlson, D. A. QSAR study of mosquito repellents using Codessa Pro. Bioorg. Med. Chem. Lett. 2006, 16, 2306-2311.
32. Sodano, G.; Caprioli, V.; Cimino, G.; Colle, R.; Gavagnin, M.; Spinella, A. Insect antifeedant activity and hot taste for humans of selected natural and synthetic 1,4-dialdehydes. J. Nat. Prod. 1987, 50, 146-151.
33. Triller, A.; Boulden, E. A.; Churchill, A.; Hatt, H.; Englund, J.; Spehr, M.; Sell, C. S. Odorant-receptor interactions and odor percept: a chemical perspective. Chem. Biodivers. 2008, 5, 862-886.
34. Hawkinson, J. E.; Casida, J. E. Binding kinetics of gammaaminobutyric acidA receptor noncompetitive antagonists: Trioxabicyclooctane, dithiane, and cyclodiene insecticide-induced slow transition to blocked chloride channel conformation. Mol. Pharm. 1992, 42, 1069-1076.
35. Ma, W. C. Alterations of chemoreceptor function in armyworm larvae (Spodoptera exempta) by a plant derived sesquiterpenoid and by sulfhydryl reagents. Physiol. Entomol. 1977, 2, 199-207.
36. Sodano, G.; D'ischia, M.; Prota, G. Reaction of polygodiaI with primary amines: an alternative explanation to the antifeedant activity. Tetrahedron Lett. 1982, 23, 3295-3298.
37. Amit, R.; Shailendra, S. Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom. Biol. Pharm. Bull. 2006, 29, 191-201.
38. Messchendorp, L.; Van Loon, J. J. A.; Gols, G. J. Z. Behavioral and sensory responses to drimane antifeedants in Pieris brassicae larvae. Entomol. Exp. Appl. 1996, 79, 195-202.
39. Bravo, H. R.; Copaja, S. V.; Agrandona, V. H. Chemical basis for the andifeedant activity of natural hydroxamic acid and related compounds. J. Agric. Food Chem 2004, 52, 2598-2601.
40. Rugutt, J. K.; Rugutt, K. J.; Berner, D. K. Limonoids from Nigerian Harrisonia abyssinica and their stimulatory activity against Striga hermonthica seeds. J. Nat. Prod. 2001, 64, 1434-1438.
41. Debnath, A. K.; Debnath, G.; Shusterman, A. J.; Hansch, C. A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: 1. Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100. Environ. Mol. Mutagen. 1992, 19, 37-52.
42. Itoh, S.; Nagashima, U. Variation effect on the insecticide activity of DDT analogues. A chemometric approach. Comput. Phys. Commun. 2002, 147, 182-185.
43. Katritzky, A. R. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 1996, 96, 1027-1044.
44. + channels AM1/DFT electronic structure investigations and QSAR studies. Comput. Biol. Chem 2008, 32, 88-101.