甜菊糖苷结构与甜味性质关系的合成研究。

Synthetic study on the relationship between structure and sweet taste properties of steviol glycosides.

机构信息

Organic Chemistry Department, Global Research and Development, the Coca-Cola Company, One Coca-Cola Plaza, Atlanta, GA 30313, USA.

出版信息

Molecules. 2012 Apr 5;17(4):4186-96. doi: 10.3390/molecules17044186.

DOI:10.3390/molecules17044186

PMID:22481539

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6268437/

Abstract

The structure activity relationship between the C₁₆-C₁₇ methylene double bond on the aglycone of steviol glycosides and the corresponding impact on their sweet taste has been reported here for the first time. It has been observed that converting stevioside and rebaudioside A to their corresponding ketones by switching the doubly bonded methylene on C-17 for a ketone group actually removes the sweet taste properties of these molecules completely. Regenerating the original molecules tends to restore the sweet taste of both the steviol glycosides. Thus this C₁₆-C₁₇ methylene double bond in rebaudioside A and stevioside can be regarded as a pharmacophore essential for the sweetness property of these molecules.

摘要

首次报道了甜菊糖苷苷元 C₁₆-C₁₇ 亚甲基双键与相应的甜度之间的构效关系。研究发现，通过将 C-17 上的亚甲基双键转换为酮基，将甜菊糖苷和瑞鲍迪苷 A 转化为相应的酮，实际上会完全去除这些分子的甜味特性。而使原始分子再生则往往会恢复这两种甜菊糖苷的甜味。因此，瑞鲍迪苷 A 和甜菊糖苷中的 C₁₆-C₁₇ 亚甲基双键可以被视为这些分子甜味特性的必需药效团。