Enzymatic Synthesis and Characterization of a Novel α-1→6-Glucosyl Rebaudioside C Derivative Sweetener

Abstract

Zero-calorie high-intensity sweeteners from natural sources perform very well in the market place. This has encouraged food scientists to continue the effort to search for novel natural ingredients to satisfy consumer demand. Rebaudioside C (reb C) is the third most prevalent steviol glycoside in the leaves of the Stevia rebaudiana Bertoni plant, but has limited applications in food and beverage products due to its low sweetness and high lingering bitterness compared to other major steviol glycosides, such as rebaudioside A (reb A). Here we present a new enzyme modification strategy to improve the taste profile of reb C by using Cargill’s propriety enzyme and sucrose as a glucose donor. A novel α-1→6-glucosyl reb C derivative was produced and its structure was elucidated by mass spectrometry and NMR spectroscopy. Sensory analysis demonstrated that this new reb C derivative has improved sweetness, reduced bitterness, and enhanced solubility in water.

RQ3, A Natural Rebaudioside D Isomer, Was Obtained from Glucosylation of Rebaudioside A Catalyzed by the CGTase Toruzyme 3.0 L

“…Prakash et al (used UGTs with UDP-glucose) ,, and Gerwig, te Poele, Devlamynck, and Yang et al ,− (used glucansucrase enzyme with sucrose as glucosyl donor) determined structures of the synthetic products using a full set of NMR and MS analyses. However, although most industrial manufacturers produce glucosyl steviol glycosides with CGTase Toruzyme 3.0 L (a commercial cyclodextrin glycosyl transferase), the linkage pattern of GSGs obtained from CGTase still remain unclear.…”

Integrated metabolite profiling and transcriptome analysis unraveling mechanism of RC catabolism in Paenarthrobacter ilicis CR5301

“…It has a low sweetness and a bitter aftertaste that affect the taste of food and beverages. Thus, its application is limited ( Yang et al, 2019 ). Previous studies have found that many glycosylation-modified products of all steviol glycosides have better sweetness and taste profiles ( Hellfritsch et al, 2012 ; Wan, 2012 ).…”

Formulating Bioactive Terpenes

“…Physicochemical characterization indicated the formation of inclusion complexes with cyclodextrin which were shown to be an effective and promising alternative to enhance the anti-inflammatory activity and safety of this triterpene. Bioactive diterpenes were also described in this Special Issue: a review and an antitumor study with cembranoids from tobacco [15,16], and glucoside derivative rebaudioside C, a sweetener [17].…”

“…Bioactive diterpenes were also described in this Special Issue: a review and an anti-tumor study with cembranoids from tobacco [ 15 , 16 ], and glucoside derivative rebaudioside C, a sweetener [ 17 ].…”

“…This wide biological property profile that turns terpenes into one of the most important classes of natural products is demonstrated in another paper published in this Special Issue. “Enzymatic Synthesis and Characterization of a Novel α-1→6-Glucosyl Rebaudioside C Derivative Sweetener” [ 17 ] brings forward this unusual sweetener characteristic from diterpenes, which are so important in food sciences in times of epidemic metabolic syndrome. In this paper, the authors present some enzymatic transformations on rebaudioside C, the third most prevalent steviol glycoside in Stevia rebaudiana leaves, to increase its applications in food and beverage products with improved sweetness, reduced bitterness and enhanced solubility in water.…”