EP-3389403-B1 - STEVIOL GLYCOSIDE COMPOSITIONS

Inventors

• PURKAYASTHA, SIDDHARTHA
• MARTIN, JOHN
• PETIT, MARCIA
• MARKOSYAN, AVETIK
• CHKHAN, KRISTINA
• ADAMYAN, MARIAM

Dates

Publication Date

20260506

Application Date

20161215

Claims (2)

1. A steviol glycoside food additive composition or a steviol glycoside extract comprising less than 95% major steviol glycosides and further comprising minor steviol glycosides, wherein the sum of the major steviol glycosides and the minor steviol glycosides is not less than 95%; wherein a) the major steviol glycosides are Reb D, Reb M, Reb A, Reb B, Reb C, Reb E, Reb F, Stevioside, Steviolbioside, Rubusoside and Dulcoside A and the minor steviol glycosides are Reb O, Reb N, Reb J, Reb Hand Reb K; or b) the major steviol glycosides are Reb A, Stevioside, Reb C, Reb F, Reb D, Rubusoside, Dulcoside A, Reb B and Steviolbioside and the minor steviol glycosides are Reb M, Reb N, Reb O, Reb E, Stevioside A and Reb C2; and wherein each minor steviol glycoside is present in the steviol glycoside food additive composition or the steviol glycoside extract in an amount of less than 5%, preferably of less than 3%.
2. The steviol glycoside food additive composition of claim 1, comprising less than 75% of the major steviol glycosides.

Description

BACKGROUND OF THE INVENTION Sugar alternatives are receiving increasing attention due to awareness of many diseases in conjunction with consumption of high-sugar foods and beverages. However, many artificial sweeteners such as dulcin, sodium cyclamate and saccharin were banned or restricted in some countries due to concerns on their safety. Therefore non-caloric sweeteners of natural origin are becoming increasingly popular. The sweet herb Stevia rebaudiana produces a number of diterpene glycosides which feature high intensity sweetness and sensory properties superior to those of many other high potency sweeteners. Stevia rebaudiana is a plant species belonging to the Astracea family, and is native to South America and cultivated now in many parts of the world (Gardana et al., 2003; Koyama et al., 2003; Carakostas et al., 2008). Stevia leaves are naturally sweet, and have been used for sweetening food products for hundreds of years in South America (Soejarto et al., 1982). Extracts of Stevia rebaudiana have been used commercially to sweeten foods in Japan and other Southeast Asian countries for a number of years (Koyama et al., 2003). As a product of nature, the stevia plant leaves contain different sweet tasting components, called steviol glycosides. Reportedly, more than 40 steviol glycosides have been identified that are typically present in the stevia leaf extract (Ceunen and Geuns, 2013; Chaturvedula et al., 2011a,b,c; Chaturvedula and Prakash, 2011a,b; Ohta et al., 2010). Each of these steviol glycosides has its own unique taste profile and sweetness intensity, which can be up to 350 times sweeter than sugar, but all share a similar molecular structure where different sugar moieties are attached to aglycone steviol (an ent-kaurene-type diterpene). The generic structure of the steviol glycosides is presented in Figure 1. Rebaudioside A and stevioside have garnered the most commercial interest and have been extensively studied and characterized in terms of their suitability as commercial high intensity sweeteners. Stability studies in carbonated beverages confirmed their heat and pH stability (Chang S. S., Cook, J. M. (1983) Stability studies of stevioside and rebaudioside A in carbonated beverages. J. Agric. Food Chem. 31: 409-412.) Steviol glycosides differ from each other not only by molecular structure, but also by their taste properties. Usually stevioside is found to be 110-270 times sweeter than sucrose and rebaudioside A is between 150 and 320 times sweeter than sucrose. Rebaudioside A has the least astringent, the least bitter, and the least persistent aftertaste thus possessing the most favorable sensory attributes in major steviol glycosides (Tanaka O. (1987) Improvement of taste of natural sweeteners. Pure Appl. Chem.69:675-683; Phillips K. C. (1989) Stevia: steps in developing a new sweetener. In: Grenby T.H. ed. Developments in sweeteners, vol. 3. Elsevier Applied Science, London. 1-43.) By the early 21st century, only a limited number of the chemical structures of steviol glycosides in Stevia rebaudiana have been characterized including stevioside, rebaudioside A-F, dulcoside A, and steviolbioside (Ceunen and Geuns, 2013). In recent years, many minor steviol glycosides with diverse chemical structures, have been reported from the leaves of Stevia rebaudiana (Chaturvedula et al., 2011a,b,c; Chaturvedula and Prakash, 2011 a,b). These diverse steviol glycosides, which are ent-kaurene-type diterpenes, are connected to various sugars such as glucose, rhamnose, xylose, fructose and deoxy glucose at C-13 and C-19 positions via 1,2-; 1,3-; 1,4- or 1,6- α or β-glycosidic linkages. The identity and grouping of various steviol glycosides is summarized in Table 1. Due to the large number of steviol glycosides, Table 1 lists the steviol glycosides in 5 groups depending on the sugar moieties connected to the steviol backbone and identified with abbreviated compositional names. Glucosyl steviol family: comprising only steviol and glucose residues. This group can be presented by general formula "SvGn", wherein Sv is the steviol and G is glucose.Rhamnosyl steviol family: comprising steviol, rhamose and glucose residues. This group can be presented by general formula "SvR1Gn", wherein R is the Rhamnose.Xylosyl steviol family: comprising steviol, xylose and glucose residues. This group can be presented by general formula "SvX1Gn", wherein X is the Xylose.Fructosyl steviol family: comprising steviol, fructose and glucose residues. This group can be presented by general formula "SvF1Gn", wherein F is the Fructose.Deoxyglucose steviol family: comprising steviol, deoxyglucose and glucose residue. This group can be presented by general formula SvdG1Gn. Table 1#Common NameAbbr. FormulaR1R21) Steviol + Glucose (SvGn)1.1SteviolmonosideSvG1HGlcβ1-1.2Steviol-19-O-β-D-glucosideSvG1Glcβ1-H1.3RubusosideSvG2Glcβ1-Glcβ1-1.4SteviolbiosideSvG2HGlcβ(1-2)Glcβ1-1.5SteviosideSvG3Glcβ1-Glcβ(1-2)Glcβ1-1.6Stevioside ASvG3Glcβ(1-2)