ISSN:
1573-1561
Keywords:
Isoflavonoids
;
structure-activity relationships
;
insect feeding-deterrent activity
;
Costelytra zealandica
;
Coleoptera
;
Scarabaeidae
;
stereochemistry
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
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 μg/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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01012122
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