WO2018106983A1 - Glucosyl stevia compositons - Google Patents
Glucosyl stevia compositons Download PDFInfo
- Publication number
- WO2018106983A1 WO2018106983A1 PCT/US2017/065235 US2017065235W WO2018106983A1 WO 2018106983 A1 WO2018106983 A1 WO 2018106983A1 US 2017065235 W US2017065235 W US 2017065235W WO 2018106983 A1 WO2018106983 A1 WO 2018106983A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- rebaudioside
- drinks
- steviol glycosides
- flavored
- salts
- Prior art date
Links
- 244000228451 Stevia rebaudiana Species 0.000 title claims abstract description 27
- -1 Glucosyl stevia Chemical compound 0.000 title claims description 4
- 235000019202 steviosides Nutrition 0.000 claims abstract description 49
- 239000004383 Steviol glycoside Substances 0.000 claims abstract description 39
- 235000019411 steviol glycoside Nutrition 0.000 claims abstract description 39
- 229930182488 steviol glycoside Natural products 0.000 claims abstract description 39
- 150000008144 steviol glycosides Chemical class 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 235000003599 food sweetener Nutrition 0.000 claims abstract description 19
- 239000003765 sweetening agent Substances 0.000 claims abstract description 19
- 235000013361 beverage Nutrition 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract description 3
- 229930188195 rebaudioside Natural products 0.000 claims description 46
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 claims description 27
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 239000001512 FEMA 4601 Substances 0.000 claims description 13
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- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 claims description 13
- 235000019203 rebaudioside A Nutrition 0.000 claims description 13
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- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- QFVOYBUQQBFCRH-VQSWZGCSSA-N steviol Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)CC1)C[C@H]2[C@@]2(C)[C@H]1[C@](C)(C(O)=O)CCC2 QFVOYBUQQBFCRH-VQSWZGCSSA-N 0.000 description 1
- 229940032084 steviol Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- 238000005918 transglycosylation reaction Methods 0.000 description 1
- 239000008371 vanilla flavor Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/36—Terpene glycosides
Definitions
- Patent Application No. 14/005,852 published as US 2014/0023750; U.S. Patent Application No. 14/005,850, published as US 2014/0010917; and U.S. Patent Application No. 14/494,322 , published as US 2015/0125571.
- the invention relates to a process for producing a sweetener from the extract of the Stevia rebaudiana plant and its use in various food products and beverages. Description of the Related Art
- 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 Bertoni produces a number of diterpene glycosides which feature high intensity sweetness and sensory properties superior to those of many other high potency sweeteners.
- the above-mentioned sweet glycosides have a common aglycon, steviol, and differ by the number and type of carbohydrate residues at the CI 3 and C19 positions.
- the leaves of Stevia are able to accumulate up to 10-20% (on dry weight basis) steviol glycosides.
- the major glycosides found in Stevia leaves are Rebaudioside A (2-10%), Stevioside (2-10%), and Rebaudioside C (1 -2%).
- Other glycosides such as Rebaudioside B, D, E, and F, Steviolbioside and Rubusoside are found at much lower levels (approx. 0- 0.2%).
- Steviol glycosides differ from each other not only by molecular structure, but also by their taste properties. Usually stevioside is found to be 1 10-270 times sweeter than sucrose, Rebaudioside A between 150 and 320 times, and Rebaudioside C between 40-60 times sweeter than sucrose. Dulcoside A is 30 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 sweetners. 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.)
- the present invention is aimed to overcome the disadvantages of existing steviol glycosides (SG) sweeteners.
- the invention describes a process for producing a high quality food ingredient from the extract of the Stevia rebaudiana plant and use thereof in various consumables, including food products and beverages, as sweetener.
- the invention in part, pertains to an ingredient comprising glucosylated derivatives of steviol glycosides of Stevia rebaudiana plant.
- the steviol glycosides are selected from the group consisting of stevioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana plant and combinations thereof.
- the invention in part, pertains to a process for producing an ingredient comprising glucosylated forms of stevioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana plant and combinations thereof.
- the process includes enzymatic transglucosylation step using CGTase.
- the process includes enzymatic transglucosylation step using CGTase produced by cultures of Bacillus stearothermophilus.
- the process may include the step of shortening glucosyl chains by ⁇ -amylase.
- the process may also include at least one step selected from the group including decolorizing, desalting, removing unreacted dextrins, concentrating, drying and combinations thereof.
- the decolorizing can be performed using activated carbon, ion-exchange resins, membrane filters, or any other method known to art for decolorizing solutions comprising organic molecules.
- the desalting can be performed by passing through ion-exchange resins, membrane filters any other method known to art for desalting solutions comprising organic molecules.
- Removing the unreacted dextrins can be performed by passing through macroporuos polymeric resin.
- Concentrating can be performed by evaporators, membrane filters any other method known to art for concentrating solutions comprising organic molecules. Drying may be performed by spray drier, flash drier, vacuum dryer, tray dryer, freeze dryer or any other method known to art for drying solutions comprising organic molecules.
- Stevia extract commercialized by PureCircle (JiangXi) Co., Ltd. (China), containing stevioside (28-30%), Rebaudioside A (50-55%), Rebaudioside C (9-12%o), Rebaudioside F (l -3%>) and other glycosides was used as a starting material.
- stevia extracts with different ratio of steviol glycosides as well as highly purified steviol glycosides such as Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana plant, may be used as starting materials.
- the starting material steviol glycosides were obtained via fermentation of recombinant microorganism.
- the starting material steviol glycosides were obtained via biotransformation of steviol glycosides extracted from Stevia plant.
- the starting material steviol glycosides were obtained via via chemical synthesis.
- the starting material was subjected to the enzymatic transglucosylation by action of cyclodextrin glycosyltransferase (CGTase) in the presence of starch as a glucose donor.
- CGTase cyclodextrin glycosyltransferase
- starch as a glucose donor.
- CGTase cyclodextrin glycosyltransferase
- «-l,4-glucosyl derivatives were formed with different degree of polymerization.
- glucose donors selected from the group including but not limited to maltodextrins, hydrolyzed starch, maltooligosaccharides, corn syrup solids, cyclodextrins, may be used.
- the unreacted dextrins from obtained reaction mixture were removed by macroporous adsorption resin.
- reaction mixture was decolorized.
- reaction mixture was desalted.
- reaction mixture was concentrated.
- reaction mixture was spray dried.
- the obtained products were applied in various consumables including foods and beverages as sweeteners.
- FIG. 1 shows an exemplary HPLC chromatogram of glucosylated steviol glycosides (GSG).
- Stevia extract commercialized by PureCircle (JiangXi) Co., Ltd. (China), containing stevioside (28-30%), Rebaudioside A (50-55%), Rebaudioside C (9-12%), Rebaudioside F (1 -3%) and other glycosides (hereinafter collectively, "steviol glycosides”) amounting to total steviol glycosides content of at least 95%, was used as a starting material.
- stevia extracts with different ratio of steviol glycosides as well as highly purified steviol glycosides such as Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana plant, may be used as starting materials.
- the HPLC analysis of the raw materials and products was performed on Agilent Technologies 1200 Series (USA) liquid chromarograph, equipped with Zorbax-NH 2 (4.6X250mm) column.
- the mobile phase was acetonitrile-water gradient from 80:20, v/v (0-2 min) to 50:50, v/v (2-70 min).
- a diode array detector set at 210 nm was used as the detector.
- the transglucosylation was accomplished by cyclomaltodextrin glucanotransferases (CGTases; EC 2.4.1.19) produced by Bacillus stear other mophilus St- 88 (PureCircle Sdn Bhd Collection of Industrial Microorganisms - Malaysia).
- CGTases cyclomaltodextrin glucanotransferases
- Bacillus stear other mophilus St- 88 Purillus stear other mophilus St- 88 (PureCircle Sdn Bhd Collection of Industrial Microorganisms - Malaysia).
- any other CGTase or enzyme possessing intermolecular transglucosylation activity may be applied as well.
- the enzyme can be in a form of cell-free culture broth, concentrated liquid cell-free culture broth, spray dried or freeze dried cell-free culture broth, or high purity protein. Free and immobilized enzyme preparations can be used.
- CGTase preparations The activity of CGTase preparations was determined according to the procedure described in Hale W.S., Rawlins L.C. (1951) Amylase of Bacillus macerans. Cereal Chem. 28, 49-58.
- Starches of different origin may be used as donors of glucosyl units such as, derived from wheat, corn, potato, tapioca, and sago.
- Other glucose donors selected from the group including but not limited to maltodextrins, hydrolyzed starch, cyclodextrins, corn syrup solids may be used.
- the starch was subjected to partial hydrolysis (liquefaction) prior to the transglycosylation reaction.
- the dextrose equivalent of the partially hydrolyzed starch can be in the range of about 10-25, preferably about 12-16.
- Any enzyme capable of starch hydrolysis may be used for liquefaction, such as a-amylases, ⁇ -amylases, CGTases etc.
- the liquefaction was conducted at about 70-90°C during about 0.5-10 hours, preferably about 1-5 hours. After liquefaction the steviol glycosides were added to the mixture and dissolved.
- the preferred ratio of steviol glycosides to starch (kg of steviol glycosides per 1 kg of starch) is about 0.5-1.5, preferably about 0.8-1.2.
- a second portion of CGTase preparation is added and the transglucosylation reaction is conducted at about 65-70°C for about 24-48 hours.
- the reaction was stopped by heating at about 95 °C for about 15 minutes to inactivate the enzymes, and the solution was treated with activated carbon, to obtain decolorized reaction mixture.
- the amount of activated carbon was about 0.02-0.4 grams per gram of solids, preferably about 0.05-0.2 grams per gram of solids.
- cartridges and/or columns packed with granulated activated carbon may be used.
- the decolorized reaction mixture was further concentrated by vacuum evaporator and dried by means of a spray dryer.
- the GSG compositions of present invention can be used as sweeteners in various consumables including food and beverage products.
- food and beverage products include carbonated soft drinks, ready to drink beverages, energy drinks, isotonic drinks, low-calorie drinks, zero-calorie drinks, sports drinks, cola flavored carbonated soft drinks, fruit flavored carbonated soft drinks, berry flavored carbonated soft drinks, flavored teas, fruit and vegetable juices, juice drinks, dairy drinks, yoghurt drinks, alcohol beverages, powdered beverages, bakery products, cookies, biscuits, baking mixes, cereals, confectioneries, candies, toffees, chewing gum, dairy products, flavored milk, yoghurts, flavored yoghurts, cultured milk, soy sauce and other soy base products, salad dressings, mayonnaise, vinegar, frozen-desserts, meat products, fish-meat products, bottled and canned foods, tabletop sweeteners, fruits and vegetables.
- compositions can be used in drug or pharmaceutical preparations and cosmetics, including but not limited to toothpaste, mouthwash, cough syrup, chewable tablets, lozenges, vitamin preparations, and the like.
- compositions can be used "as-is” or in combination with other sweeteners, flavors and food ingredients.
- Non-limiting examples of sweeteners include sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, allulose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, turanose, sialose, inulin, inulooligosaccharides, fructooligosaccharides, high fructose corn syrup (HFCS), maltodextrin, coupling sugar, honey, erythritol, xylitol, mannitol, sorbi
- Non-limiting examples of flavors include lemon, orange, fruity, banana, grape, pear, pineapple, bitter almond, lemon, lime, cola, cinnamon, sugar, cotton candy, vanilla flavors.
- Non-limiting examples of other food ingredients include flavors, acidulants, organic and amino acids, coloring agents, polyols, fibers, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilisers, thickeners, gelling agents.
- a strain of Bacillus stearothermophilus St-88 was inoculated in 2,000 liters of sterilized culture medium containing 1.0% starch, 0.25% corn extract, 0.5% (NH ⁇ SC ⁇ , and 0.2% CaC0 3 (pH 7.0-7.5) at 56°C for 24 hrs with continuous aeration (2,000 L/min) and agitation (150rpm).
- the obtained culture broth was filtered using Kerasep 0.1 ⁇ ceramic membrane (Novasep, France) to separate the cells.
- the cell-free permeate was further concentrated 5-fold on Persep lOkDa ultrafilters (Orelis, France).
- the trace sediment in the filtrate was removed using a self de-sludging centrifuge (Alfa -Laval MPRX31456V-34C 1/4271-6) and a dead end filter (Eaton, ACCUGAF, AGFE-51-R02H0O-15L, pore size 1 ⁇ ).
- the decolorised solution was concentrated at 70°C under vacuum, using NIRO thin falling film evaporator (running in MVR mode) until 60 % (w/w) total solids content.
- the concentrated solution was dried into powder form using NIRO250 multistage spray dryer operating at an inlet temperature of 198°C and outlet temperature of 77°C. 9,000 kg of glucosyl steviol glycosides (GSG) composition was obtained (FIG 1).
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Abstract
Glucosyl steviol glycosides (GSG) compositions are prepared from steviol glycosides of Stevia rebaudiana. The GSG compositions can be used as sweeteners in various consumables including foods, beverages, cosmetics and pharmaceuticals.
Description
GLUCOSYL STEVIA COMPOSITIONS
Related applications
This patent application claims priority to U.S. Provisional Patent Application No. 62/432, 172, filed on December 9, 2016, which is incorporated by reference herein in its entirety.
For purposes of the United States of America, this patent application is also a continuation-in-part of the following applications, each of which is incorporated by reference herein in its entirety: U.S. Patent Application No. 15/646,629, filed on July 1 1,
2017; U.S. Patent Application No. 15/470,388, filed on March 27, 2017; U.S. Patent
Application No. 14/273,056, filed on May 8, 2014; U.S. Patent Application No.
15/437,208, filed on February 20, 2017; U.S. Patent Application No. 15/550,075, filed on August 10, 2017; U.S. Patent Application No. 15/213,013, filed on July 18, 2016; U.S.
Patent Application No. 15/243,504, filed on August 22, 2016; U.S. Patent Application No.
15/332,760, filed on October 24, 2016; and U.S. Patent Application No. 14/494,322, filed on September 23, 2014. This patent application also incorporates by reference each of the following patents in its entirety: U.S. Patent Nos. 7,807,206, 7,838,044, 8,257,948, 8,318,459, 8,647,844, 8,669,077, 8,318,232, 8,323,716, 8,735, 101, 8,911,971, 8,993,269, 9,055,761, 9, 107,436, 9,386,797, 9,392,799, 9,420,815, 9,474,296, 9,585,420, 9,603,373, and 9,706,792. This patent application also incorporates each of the following patent applications in its entirety: U.S. Patent Application No. 14/005,852, published as US 2014/0023750; U.S. Patent Application No. 14/005,850, published as US 2014/0010917; and U.S. Patent Application No. 14/494,322 , published as US 2015/0125571.
Field of the Invention
The invention relates to a process for producing a sweetener from the extract of the Stevia rebaudiana plant and its use in various food products and beverages.
Description of the Related Art
Nowadays 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 Bertoni, produces a number of diterpene glycosides which feature high intensity sweetness and sensory properties superior to those of many other high potency sweeteners.
The above-mentioned sweet glycosides, have a common aglycon, steviol, and differ by the number and type of carbohydrate residues at the CI 3 and C19 positions. The leaves of Stevia are able to accumulate up to 10-20% (on dry weight basis) steviol glycosides. The major glycosides found in Stevia leaves are Rebaudioside A (2-10%), Stevioside (2-10%), and Rebaudioside C (1 -2%). Other glycosides such as Rebaudioside B, D, E, and F, Steviolbioside and Rubusoside are found at much lower levels (approx. 0- 0.2%).
Two major glycosides - Stevioside and Rebaudioside A, were 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 1 10-270 times sweeter than sucrose, Rebaudioside A between 150 and 320 times, and Rebaudioside C between 40-60 times sweeter than sucrose. Dulcoside A is 30 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 sweetners. 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.)
Methods for the extraction and purification of sweet glycosides from the Stevia rebaudiana plant using water or organic solvents are described in, for example, U.S.
Patent Numbers 4,361,697; 4,082,858; 4,892,938; 5,972, 120; 5,962,678; 7,838,044 and 7,862,845.
However, even in a highly purified state, steviol glycosides still possess undesirable taste attributes such as bitterness, sweet aftertaste, licorice flavor, etc. One of the main obstacles for the successful commercialization of stevia sweeteners are these undesirable taste attributes. It was shown that these flavor notes become more prominent as the concentration of steviol glycosides increases (Prakash I., DuBois G.E., Clos J.F., Wilkens K.L., Fosdick L.E. (2008) Development of rebiana, a natural, non-caloric sweetener. Food Chem. Toxicol., 46, S75-S82.)
On the other hand, replacing large amounts of sugar in the formulations brings up such problems as reduced mouthfeel, incomplete flavor profile etc. Therefore the application of high intensity low calorie sweeteners has to provide solutions to address these problems.
Thus, if a single composition will be able to deliver not only sweetness, but also possess flavor enhancing properties and correct the incomplete mouthfeel associated with the elimination of sucrose from food and beverage formulations, it will certainly be advantageous compared to other high intensity sweeteners known in the art.
Therefore it is necessary to develop new generation of stevia sweeteners which will possess improved organoleptic properties.
SUMMARY OF THE INVENTION
The present invention is aimed to overcome the disadvantages of existing steviol glycosides (SG) sweeteners. The invention describes a process for producing a high quality food ingredient from the extract of the Stevia rebaudiana plant and use thereof in various consumables, including food products and beverages, as sweetener.
The invention, in part, pertains to an ingredient comprising glucosylated derivatives of steviol glycosides of Stevia rebaudiana plant. The steviol glycosides are selected from the group consisting of stevioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana
plant and combinations thereof.
The invention, in part, pertains to a process for producing an ingredient comprising glucosylated forms of stevioside, Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana plant and combinations thereof.
In one embodiment the process includes enzymatic transglucosylation step using CGTase.
In another embodiment the process includes enzymatic transglucosylation step using CGTase produced by cultures of Bacillus stearothermophilus.
The process may include the step of shortening glucosyl chains by ^-amylase.
The process may also include at least one step selected from the group including decolorizing, desalting, removing unreacted dextrins, concentrating, drying and combinations thereof.
The decolorizing can be performed using activated carbon, ion-exchange resins, membrane filters, or any other method known to art for decolorizing solutions comprising organic molecules. The desalting can be performed by passing through ion-exchange resins, membrane filters any other method known to art for desalting solutions comprising organic molecules. Removing the unreacted dextrins can be performed by passing through macroporuos polymeric resin. Concentrating can be performed by evaporators, membrane filters any other method known to art for concentrating solutions comprising organic molecules. Drying may be performed by spray drier, flash drier, vacuum dryer, tray dryer, freeze dryer or any other method known to art for drying solutions comprising organic molecules.
In one embodiment, Stevia extract commercialized by PureCircle (JiangXi) Co., Ltd. (China), containing stevioside (28-30%), Rebaudioside A (50-55%), Rebaudioside C (9-12%o), Rebaudioside F (l -3%>) and other glycosides was used as a starting material. Alternatively stevia extracts with different ratio of steviol glycosides as well as highly purified steviol glycosides such as Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H,
Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana plant, may be used as starting materials.
In one embodiment the starting material steviol glycosides were obtained via fermentation of recombinant microorganism.
In another embodiment the starting material steviol glycosides were obtained via biotransformation of steviol glycosides extracted from Stevia plant.
In yet another embodiment the starting material steviol glycosides were obtained via via chemical synthesis.
The starting material was subjected to the enzymatic transglucosylation by action of cyclodextrin glycosyltransferase (CGTase) in the presence of starch as a glucose donor. As a result «-l,4-glucosyl derivatives were formed with different degree of polymerization. Alternatively other glucose donors selected from the group including but not limited to maltodextrins, hydrolyzed starch, maltooligosaccharides, corn syrup solids, cyclodextrins, may be used.
In one embodiment, the unreacted dextrins from obtained reaction mixture were removed by macroporous adsorption resin.
In yet another embodiment the reaction mixture was decolorized.
In one embodiment the reaction mixture was desalted.
In another embodiment the reaction mixture was concentrated.
In yet another embodiment the reaction mixture was spray dried.
The obtained products were applied in various consumables including foods and beverages as sweeteners.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed.
BRIEF DESCRIPTION OF THE DRAWINGS
The accompanying drawings are included to provide a further understanding of the invention. The drawings illustrate embodiments of the invention and together with the description serve to explain the principles of the embodiments of the invention.
FIG. 1 shows an exemplary HPLC chromatogram of glucosylated steviol glycosides (GSG).
DETAILED DESCRIPTION OF THE INVENTION
Advantages of the present invention will become more apparent from the detailed description given hereinafter. However, it should be understood that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
In one embodiment, Stevia extract commercialized by PureCircle (JiangXi) Co., Ltd. (China), containing stevioside (28-30%), Rebaudioside A (50-55%), Rebaudioside C (9-12%), Rebaudioside F (1 -3%) and other glycosides (hereinafter collectively, "steviol glycosides") amounting to total steviol glycosides content of at least 95%, was used as a starting material. Alternatively stevia extracts with different ratio of steviol glycosides as well as highly purified steviol glycosides such as Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E, Rebaudioside F, Rebaudioside G, Rebaudioside H, Rebaudioside I, Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M, Rebaudioside N, Rebaudioside O, Rebaudioside Q, dulcoside A, steviolbioside, rubusoside, as well as other steviol glycosides found in Stevia rebaudiana plant, may be used as starting materials.
The HPLC analysis of the raw materials and products was performed on Agilent Technologies 1200 Series (USA) liquid chromarograph, equipped with Zorbax-NH2 (4.6X250mm) column. The mobile phase was acetonitrile-water gradient from 80:20, v/v (0-2 min) to 50:50, v/v (2-70 min). A diode array detector set at 210 nm was used as the detector.
The transglucosylation was accomplished by cyclomaltodextrin glucanotransferases (CGTases; EC 2.4.1.19) produced by Bacillus stear other mophilus St- 88 (PureCircle Sdn Bhd Collection of Industrial Microorganisms - Malaysia). However, any other CGTase or enzyme possessing intermolecular transglucosylation activity may be applied as well. The enzyme can be in a form of cell-free culture broth, concentrated liquid
cell-free culture broth, spray dried or freeze dried cell-free culture broth, or high purity protein. Free and immobilized enzyme preparations can be used.
The activity of CGTase preparations was determined according to the procedure described in Hale W.S., Rawlins L.C. (1951) Amylase of Bacillus macerans. Cereal Chem. 28, 49-58.
Starches of different origin may be used as donors of glucosyl units such as, derived from wheat, corn, potato, tapioca, and sago. Alternatively other glucose donors selected from the group including but not limited to maltodextrins, hydrolyzed starch, cyclodextrins, corn syrup solids may be used.
In one embodiment the starch was subjected to partial hydrolysis (liquefaction) prior to the transglycosylation reaction. The dextrose equivalent of the partially hydrolyzed starch can be in the range of about 10-25, preferably about 12-16. Any enzyme capable of starch hydrolysis may be used for liquefaction, such as a-amylases, ^-amylases, CGTases etc.
In one embodiment the concentration of starch in liquefaction mixture was about
15-40% (wt/wt), preferably about 20-30%.
In one embodiment the liquefaction was conducted at about 70-90°C during about 0.5-10 hours, preferably about 1-5 hours. After liquefaction the steviol glycosides were added to the mixture and dissolved. The preferred ratio of steviol glycosides to starch (kg of steviol glycosides per 1 kg of starch) is about 0.5-1.5, preferably about 0.8-1.2.
In one embodiment a second portion of CGTase preparation is added and the transglucosylation reaction is conducted at about 65-70°C for about 24-48 hours.
In one embodiment The reaction was stopped by heating at about 95 °C for about 15 minutes to inactivate the enzymes, and the solution was treated with activated carbon, to obtain decolorized reaction mixture. The amount of activated carbon was about 0.02-0.4 grams per gram of solids, preferably about 0.05-0.2 grams per gram of solids. Alternatively cartridges and/or columns packed with granulated activated carbon, may be used.
The decolorized reaction mixture was further concentrated by vacuum evaporator and dried by means of a spray dryer.
The GSG compositions of present invention can be used as sweeteners in various consumables including food and beverage products. Non-limiting examples of food and
beverage products include carbonated soft drinks, ready to drink beverages, energy drinks, isotonic drinks, low-calorie drinks, zero-calorie drinks, sports drinks, cola flavored carbonated soft drinks, fruit flavored carbonated soft drinks, berry flavored carbonated soft drinks, flavored teas, fruit and vegetable juices, juice drinks, dairy drinks, yoghurt drinks, alcohol beverages, powdered beverages, bakery products, cookies, biscuits, baking mixes, cereals, confectioneries, candies, toffees, chewing gum, dairy products, flavored milk, yoghurts, flavored yoghurts, cultured milk, soy sauce and other soy base products, salad dressings, mayonnaise, vinegar, frozen-desserts, meat products, fish-meat products, bottled and canned foods, tabletop sweeteners, fruits and vegetables.
Additionally the compositions can be used in drug or pharmaceutical preparations and cosmetics, including but not limited to toothpaste, mouthwash, cough syrup, chewable tablets, lozenges, vitamin preparations, and the like.
The compositions can be used "as-is" or in combination with other sweeteners, flavors and food ingredients.
Non-limiting examples of sweeteners include sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, allulose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, turanose, sialose, inulin, inulooligosaccharides, fructooligosaccharides, high fructose corn syrup (HFCS), maltodextrin, coupling sugar, honey, erythritol, xylitol, mannitol, sorbitol, inositol, stevia, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside I, rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, dulcoside B, rubusoside, steviolbioside, stevioside, other steviol glycosides occurring in Stevia rebaudiana plant, biosynthetic steviol glycosides, glycosylated steviol glycosides, glucosylated steviol glycosides (GSGs), mogroside IV, mogroside V, mogroside VI, Luo han guo, siamenoside, other mogrosides occurring in Siraitia grosvenorii fruits, monatin and its salts, curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, and cyclocarioside I, sugar alcohols, sucralose, potassium
acesulfame, acesulfame acid and salts thereof, aspartame, alitame, saccharin and salts thereof, neohesperidin dihydrochalcone, naringin dihydrochalcone, cyclamate, cyclamic acid and salts thereof, neotame, advantame, and combinations thereof.
Non-limiting examples of flavors include lemon, orange, fruity, banana, grape, pear, pineapple, bitter almond, lemon, lime, cola, cinnamon, sugar, cotton candy, vanilla flavors.
Non-limiting examples of other food ingredients include flavors, acidulants, organic and amino acids, coloring agents, polyols, fibers, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilisers, thickeners, gelling agents.
The following examples illustrate various embodiments of the invention. It will be understood that the invention is not limited to the materials, proportions, conditions and procedures set forth in the examples, which are only illustrative.
EXAMPLE 1
Preparation of CGTase
A strain of Bacillus stearothermophilus St-88 was inoculated in 2,000 liters of sterilized culture medium containing 1.0% starch, 0.25% corn extract, 0.5% (NH^SC^, and 0.2% CaC03 (pH 7.0-7.5) at 56°C for 24 hrs with continuous aeration (2,000 L/min) and agitation (150rpm). The obtained culture broth was filtered using Kerasep 0.1 μιη ceramic membrane (Novasep, France) to separate the cells. The cell-free permeate was further concentrated 5-fold on Persep lOkDa ultrafilters (Orelis, France).
EXAMPLE 2
Preparation of glucosyl steviol glycosides (GSG) composition
5,000 kg of tapioca starch was suspended in 13,600 L of water (pH 6) then 71 kg of CGTase, prepared according to Example 1, was added, and the liquefaction of starch was carried out at 83°C for about 4 hours. Then 5,000 kg of stevia extract was added to liquefied starch and the mixture was heated in a heat exchanger to 105°C until a homogeneous solution was obtained. 704 kg of CGTase, prepared according to Example 1, was added to the solution and the mixture was held at a temperature of 68°C for 48 hours under continuous agitation. The mixture was passed through two 2m3 columns packed with Norit GAC1240 PLUS granulated activated carbon (connected in in series) for decolorisation. The trace sediment in the filtrate (including residues the active carbon) was
removed using a self de-sludging centrifuge (Alfa -Laval MPRX31456V-34C 1/4271-6) and a dead end filter (Eaton, ACCUGAF, AGFE-51-R02H0O-15L, pore size 1 μηι). The decolorised solution was concentrated at 70°C under vacuum, using NIRO thin falling film evaporator (running in MVR mode) until 60 % (w/w) total solids content. The concentrated solution was dried into powder form using NIRO250 multistage spray dryer operating at an inlet temperature of 198°C and outlet temperature of 77°C. 9,000 kg of glucosyl steviol glycosides (GSG) composition was obtained (FIG 1).
Claims
1. A sweetener composition comprising a-l,4-glucosyl derivatives of steviol glycosides.
2. A sweetener composition of claim 1 comprising at least one sweetener selected from the group consisting of sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, allulose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, turanose, sialose, inulin, inulooligosaccharides, fructooligosaccharides, high fructose corn syrup (HFCS), maltodextrin, coupling sugar, honey, erythritol, xylitol, mannitol, sorbitol, inositol, stevia, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside I, rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, dulcoside B, rubusoside, steviolbioside, stevioside, other steviol glycosides occurring in Stevia rebaudiana plant, biosynthetic steviol glycosides, glycosylated steviol glycosides, mogroside IV, mogroside V, mogroside VI, Luo han guo, siamenoside, other mogrosides occurring in Siraitia grosvenorii fruits, monatin and its salts, curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin, phloridzin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, and cyclocarioside I, sugar alcohols, sucralose, potassium acesulfame, acesulfame acid and salts thereof, aspartame, alitame, saccharin and salts thereof, neohesperidin dihydrochalcone, naringin dihydrochalcone, cyclamate, cyclamic acid and salts thereof, neotame, advantame, and combinations thereof.
3. A consumable comprising sweetener composition of claim 1, selected from the group including carbonated soft drinks, ready to drink beverages, energy drinks, isotonic drinks, low-calorie drinks, zero-calorie drinks, sports drinks, cola flavored carbonated soft drinks, fruit flavored carbonated soft drinks, berry flavored carbonated soft drinks, flavored teas, fruit and vegetable juices, juice drinks, dairy drinks, yoghurt drinks, alcohol beverages, powdered beverages, bakery products, cookies, biscuits, baking mixes, cereals, confectioneries, candies, chocolates, toffees, chewing gum, dairy products, flavored milk,
yoghurts, flavored yoghurts, cultured milk, soy sauce and other soy base products, salad dressings, mayonnaise, vinegar, frozen-desserts, meat products, fish-meat products, bottled and canned foods, tabletop sweeteners, fruits and vegetables, drug or pharmaceutical preparations, cosmetics, toothpaste, mouthwash, cough syrup, chewable tablets, lozenges, vitamin preparations.
4. A consumable of claim 3, further comprising at least one food ingredient selected from the group consisting of: acidulants, organic and amino acids, coloring agents, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilisers, thickeners, gelling agents, and a combination thereof.
A method of sweetening a consumable by adding a composition of claim 1.
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| US16/467,805 US20210368839A1 (en) | 2005-10-11 | 2017-12-08 | Glucosyl stevia compositions |
| US17/991,991 US20230085655A1 (en) | 2014-05-08 | 2022-11-22 | Glucosyl stevia compositions |
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| US201662432172P | 2016-12-09 | 2016-12-09 | |
| US62/432,172 | 2016-12-09 |
Related Parent Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2016/017236 Continuation-In-Part WO2016130609A1 (en) | 2005-10-11 | 2016-02-10 | Rebaudioside m biosynthetic production and recovery methods |
| US15/550,075 Continuation-In-Part US20180020709A1 (en) | 2014-04-16 | 2016-02-10 | Rebaudioside m biosynthetic production and recovery methods |
| US15/213,013 Continuation-In-Part US10729163B2 (en) | 2005-10-11 | 2016-07-18 | Glucosyl stevia composition |
| US15/243,504 Continuation-In-Part US10130116B2 (en) | 2005-10-11 | 2016-08-22 | Glucosylated steviol glycoside as a flavor modifier |
| US15/332,760 Continuation-In-Part US11678685B2 (en) | 2005-10-11 | 2016-10-24 | Glucosyl stevia composition |
| US15/437,208 Continuation-In-Part US10398160B2 (en) | 2005-10-11 | 2017-02-20 | Glucosylated steviol glycoside as a flavor modifier |
| US15/646,629 Continuation-In-Part US20170303572A1 (en) | 2005-10-11 | 2017-07-11 | Glucosyl stevia composition |
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| US16/467,805 A-371-Of-International US20210368839A1 (en) | 2005-10-11 | 2017-12-08 | Glucosyl stevia compositions |
| US17/991,991 Continuation US20230085655A1 (en) | 2014-05-08 | 2022-11-22 | Glucosyl stevia compositions |
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| CN109022625A (en) * | 2018-09-18 | 2018-12-18 | 上海立足生物科技有限公司 | A method of producing the D-Psicose of concentration |
| WO2020205978A1 (en) * | 2019-04-01 | 2020-10-08 | The Coca-Cola Company | Compositions containing brazzein |
| CN115250612A (en) * | 2020-06-03 | 2022-10-28 | 弗门尼舍有限公司 | Compositions for reducing off-flavors and uses thereof |
| US11918675B2 (en) | 2019-12-16 | 2024-03-05 | Colgate-Palmolive Company | Oral care compositions |
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| US7267835B2 (en) * | 2001-09-21 | 2007-09-11 | Dainippon Ink And Chemicals, Inc. | Sweetener and process for producing the same |
| US20120214752A1 (en) * | 2011-02-17 | 2012-08-23 | Avetik Markosyan | Glucosyl Stevia Composition |
| US20150141632A1 (en) * | 2010-03-12 | 2015-05-21 | Purecircle Usa Inc. | High-purity steviol glycosides |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7267835B2 (en) * | 2001-09-21 | 2007-09-11 | Dainippon Ink And Chemicals, Inc. | Sweetener and process for producing the same |
| US20150141632A1 (en) * | 2010-03-12 | 2015-05-21 | Purecircle Usa Inc. | High-purity steviol glycosides |
| US20120214752A1 (en) * | 2011-02-17 | 2012-08-23 | Avetik Markosyan | Glucosyl Stevia Composition |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109022625A (en) * | 2018-09-18 | 2018-12-18 | 上海立足生物科技有限公司 | A method of producing the D-Psicose of concentration |
| WO2020205978A1 (en) * | 2019-04-01 | 2020-10-08 | The Coca-Cola Company | Compositions containing brazzein |
| CN113939197A (en) * | 2019-04-01 | 2022-01-14 | 可口可乐公司 | Composition containing Blazidine |
| US11918675B2 (en) | 2019-12-16 | 2024-03-05 | Colgate-Palmolive Company | Oral care compositions |
| CN115250612A (en) * | 2020-06-03 | 2022-10-28 | 弗门尼舍有限公司 | Compositions for reducing off-flavors and uses thereof |
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