Characterization and feeding deterrent effects on the aphid, Schizaphis graminum, of some derivatives of the sweet compounds, stevioside and rebaudioside A.
The intensely sweet compounds, stevioside [1] and rebaudioside A [2], and 15 of their derivatives, were tested for feeding deterrent activity against the aphid, Schizaphis graminum. Included with these compounds was steviol [4], the aglycone of stevioside and rebaudioside A that was one of the most active compounds in this investigation. Loss of feeding deterrent activity of steviol was observed on acetylation or glycosylation of the C-13 tertiary hydroxy group or on methylation of the C-19 carboxylic acid substituent. In contrast, the antifeedant activity of steviol was not greatly affected by modification of either the C-16 exomethylene group or the C/D-ring junction stereochemistry. 13C-nmr data have been obtained for 12 of the test compounds investigated.
Nanayakkara
N P
NP
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago 60612.
Klocke
J A
JA
Compadre
C M
CM
Hussain
R A
RA
Pezzuto
J M
JM
Kinghorn
A D
AD
D000818:Animals; D001042:Aphids / Q000502:physiology*; D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005247:Feeding Behavior / Q000187:drug effects*; D005960:Glucosides / Q000032:analysis / Q000494:pharmacology*; D006027:Glycosides / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013549:Sweetening Agents / Q000032:analysis / Q000494:pharmacology*; D013729:Terpenes / Q000032:analysis / Q000494:pharmacology*
D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005960:Glucosides; D006027:Glycosides; D013549:Sweetening Agents; D013729:Terpenes; C012043:stevioside; C025474:rebaudioside A