Lost and found in sweeteners: forgotten molecules and unsolved problems in the chemistry of sweet compounds

Abstract

The chemistry of sweet compounds has been an ideal training ground for researchers in the field of taste for a very long time. Sweeteners have a huge importance in the food and pharmaceutical industries, but they have also attracted much interest in connection with their biological function and the general mechanism of action of sweet compounds. Several factors contributed to a large and varied production of scientific data in this field: among these the existence of several active compounds in the plant kingdom, the diversity of structural, stereochemical and conformational hallmarks, the intriguing aspects related to their modulation, inhibition and synergy. Among all molecules that have been isolated and synthesized, only a few have successfully reached the final goal of commercial development while some have been used to derive models and structure-activity relationships. Nevertheless, there is a number of very interesting compounds of natural or synthetic origin that -after a short period of popularity -were apparently lost or forgotten, without any further development. The article will give an overview on some of these compounds and discuss, in the light of current knowledge, the contribution that chemistry still could give in the sweeteners area.

Development of an analytical methodology using Fourier transform mass spectrometry to discover new structural analogs of wine natural sweeteners

“…Decreasing carbohydrate intake is a major public health issue so when a high-potency sweetener is identified, it is common to search for structural analogs with similar, or even more interesting, properties [19][20][21]. In general, chemical synthesis is involved in generating these analogs by making slight modifications to the stereochemistry or substituents of the sweetener [22][23][24][25].…”

Structure-Dependent Activity of Plant-Derived Sweeteners

“…Having already been isolated in 1929, (+)-phyllodulcin (17) served as lead compound for the development of new sweeteners and for models to describe their structure-activity relationships [47]. These studies focused on the isovanillyl group, which is responsible for the sweetening effect and resulted in the synthesis of several derivatives [48].…”

Taste Detection and Recognition Thresholds of The Modified Monellin Sweetener: MNEI

“…However, over the centuries, several hundred synthetic and natural molecules have been found to be sweet, such as sugars, amino acids, peptides, proteins, olefinic alcohols, nitroanilines, saccharin, chloroform and many other organic compounds . Indeed, some sweet compounds, after a short period of popularity, were apparently lost or forgotten, such as osladin, hernandulcin, phyllodulcin and other ones, as reported by Bassoli et al (2011). Sweet molecules can be grouped in terms of chemical characteristics, molecular weight and size.…”

“…Indeed, some sweet compounds, after a short period of popularity, were apparently lost or forgotten, such as osladin, hernandulcin, phyllodulcin and other ones, as reported by Bassoli et al . (). Sweet molecules can be grouped in terms of chemical characteristics, molecular weight and size.…”