DuBois G E, Stephenson R A
J Med Chem. 1985 Jan;28(1):93-8. doi: 10.1021/jm00379a017.
Congeneric series of stevioside (1) and rebaudioside A (3) analogues have been prepared. It was found that the bitter-taste component endogenous in the natural compounds 1 and 3 may be eliminated by increase in molecular hydrophilic character. Through the series of compounds prepared, bitter-taste character was correlated with k', a chromatographic indicator of gross hydrophilicity. An analogue (11) of stevioside, shown chromatographically to be of increased hydrophilicity, was prepared and found to exhibit no bitter-taste character. Similarly an analogue (13) of rebaudioside A, having increased polarity, was prepared and found not to exhibit any bitter taste. The rebaudioside A analogue 13 was determined to have higher potency than 11 is suggested as a potential non-nutritive sweetener for food applications.
已制备了甜菊糖苷（1）和莱鲍迪苷A（3）类似物的同系物系列。发现天然化合物1和3中的内源性苦味成分可通过增加分子亲水性来消除。通过制备的一系列化合物，苦味特性与k'相关，k'是总体亲水性的色谱指标。制备了一种甜菊糖苷类似物（11），色谱显示其亲水性增加，发现其没有苦味特性。同样，制备了一种莱鲍迪苷A类似物（13），其极性增加，发现也没有任何苦味。莱鲍迪苷A类似物13被确定具有比11更高的效力，被认为是一种潜在的用于食品应用的非营养性甜味剂。
