title: Characterization and feeding deterrent effects on the aphid, Schizaphis graminum, of some derivatives of the sweet compounds, stevioside and rebaudioside A.
abstract: 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.
authors: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago 60612.
authors: N P
authors: NP
authors: Nanayakkara
authors: J A
authors: JA
authors: Klocke
authors: C M
authors: CM
authors: Compadre
authors: R A
authors: RA
authors: Hussain
authors: J M
authors: JM
authors: Pezzuto
authors: A D
authors: AD
authors: Kinghorn
mesh_terms: 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*
chemical_list: D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005960:Glucosides; D006027:Glycosides; D013549:Sweetening Agents; D013729:Terpenes; C012043:stevioside; C025474:rebaudioside A