title: Diterpenoid sweeteners. Synthesis and sensory evaluation of stevioside analogues with improved organoleptic properties.
abstract: 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.
mesh_terms: D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005960:Glucosides / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D006801:Humans; D013549:Sweetening Agents / Q000138:chemical synthesis*; D013649:Taste / Q000187:drug effects; D013729:Terpenes / Q000138:chemical synthesis*
chemical_list: D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005960:Glucosides; D006027:Glycosides; D013549:Sweetening Agents; D013729:Terpenes; C012043:stevioside