Abstract
A minor product, rebaudioside M2 (2), from the bioconversion reaction of rebaudioside A (4) to rebaudioside D (3), was isolated and the complete structure of the novel steviol glycoside was determined. Rebaudioside M2 (2) is considered an isomer of rebaudioside M (1) and contains a relatively rare 1→6 sugar linkage. It was isolated and characterized with NMR (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D-TOCSY, and NOESY) and mass spectral data. Additionally, we emphasize the importance of 1D and 2D NMR techniques when identifying complex steviol glycosides. Numerous NMR spectroscopy studies of rebaudioside M (1), rebaudioside D (3), and mixture of 1 and 3 led to the discovery that SG17 which was previously reported in literature, is a mixture of rebaudioside D (3), rebaudioside M (1), and possibly other related steviol glycosides.
Highlights
Sweetness is universally regarded as pleasant and preferred taste for beverages, food, pharmaceuticals, and oral hygiene/cosmetic products
In the present study we report the isolation and characterization of a novel isomer of rebaudioside M, called rebaudioside M2 (2) from the bioconversion reaction of rebaudioside A (4) to rebaudioside D (3)
To our knowledge this is the first report of isolation and complete characterization using NMR (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D-TOCSY and NOESY) (Supplementary, Figure S1) and high resolution mass spectral data of rebaudioside M2 (2)
Summary
Sweetness is universally regarded as pleasant and preferred taste for beverages, food, pharmaceuticals, and oral hygiene/cosmetic products. To provide sweet taste to consumer products the most commonly used natural caloric sugars are sucrose, fructose, and glucose. Steviol glycosides isolated from Stevia rebaudiana Bertoni have been explored to produce an ideal sweetener (sweet, low to no calorie, and natural) [5,6,7,8,9,10,11,12]. The leaves of S. rebaudiana contain several naturally sweet steviol glycoside such as steviolbioside, stevioside, rebaudioside A–F, dulcoside A and rubusoside [15,16,17,18,19,20]. Most recently we reported the isolation (from S. rebaudiana Bertoni), characterization and sensory evaluation for sweetness properties of rebaudioside M ( known as rebaudioside X) (1) (Figure 1) [21,22]. S. rebaudiana Morita [24,25]
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