Nanayakkara N P, Klocke J A, Compadre C M, Hussain R A, Pezzuto J M, Kinghorn A D
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago 60612.
J Nat Prod. 1987 May-Jun;50(3):434-41. doi: 10.1021/np50051a015.
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.
对甜菊糖苷[1]、莱鲍迪苷A[2]这两种极甜的化合物及其15种衍生物进行了测试，以检测它们对麦二叉蚜的拒食活性。这些化合物中还包括甜菊醇[4]，它是甜菊糖苷和莱鲍迪苷A的苷元，是本研究中活性最强的化合物之一。当C-13叔羟基乙酰化或糖基化，或C-19羧酸取代基甲基化时，观察到甜菊醇的拒食活性丧失。相比之下，C-16亚甲基或C/D环连接立体化学的修饰对甜菊醇的拒食活性影响不大。已获得所研究的12种测试化合物的13C核磁共振数据。
