Isoflavonoid feeding deterrents forCostelytra zealandica Structure — Activity relationships |
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Authors: | Geoffrey A Lane David R Biggs Graeme B Russell Oliver R W Sutherland E Maree Williams John H Maindonald Deborah J Donnell |
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Affiliation: | (1) Applied Biochemistry Division, DSIR, Palmerston North, New Zealand;(2) Entomology Division, DSIR, Auckland, New Zealand;(3) Applied Mathematics Division, DSIR, Auckland, New Zealand |
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Abstract: | A number of naturally occurring isoflavonoids of differing substitution patterns and oxidation states have been tested for feeding deterrent activity in a bioassay with larvae ofCostelytra zealandica White. The most active deterrents, which reduced feeding significantly at 0.2-1.0 g/g, are those compounds containing a ring B-fused cycloprenoid moiety. The least active compounds were highly oxidized coumestans and isoflavones. The ring B-fused cyclic isoprenoid moiety and the presence of a 2'-oxy function appear to be structural features important for high activity. It is suggested that the feeding deterrent activity of isoflavonoids relates to their stereochemistry and that the most active compounds have or can adopt a similar nonplanar molecular shape with a similar arrangement of polar and lipophilic groups. |
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Keywords: | Isoflavonoids structure-activity relationships insect feeding-deterrent activity Costelytra zealandica Coleoptera Scarabaeidae stereochemistry |
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