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WO2018106983A1 - Compositions de stevia glucosylé - Google Patents

Compositions de stevia glucosylé Download PDF

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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
Application number
PCT/US2017/065235
Other languages
English (en)
Inventor
Avetik Markosyan
Original Assignee
Purecircle Usa Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Purecircle Usa Inc. filed Critical Purecircle Usa Inc.
Priority to US16/467,805 priority Critical patent/US20210368839A1/en
Publication of WO2018106983A1 publication Critical patent/WO2018106983A1/fr
Priority to US17/991,991 priority patent/US20230085655A1/en

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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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  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

La présente invention concerne des compositions de glucosides de stéviol glucosylés (GSG) préparées à partir de glycosides de stéviol de Stevia rebaudiana. Les compositions GSG peuvent être utilisées comme édulcorants dans divers produits consommables, notamment des aliments, des boissons, des produits cosmétiques et des produits pharmaceutiques.
PCT/US2017/065235 2005-10-11 2017-12-08 Compositions de stevia glucosylé WO2018106983A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
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

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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 (fr) 2005-10-11 2016-02-10 Production biosynthétique de rébaudioside m et procédés de récupération
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

Related Child Applications (2)

Application Number Title Priority Date Filing Date
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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WO2018106983A1 true WO2018106983A1 (fr) 2018-06-14

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109022625A (zh) * 2018-09-18 2018-12-18 上海立足生物科技有限公司 一种生产浓缩的d-阿洛酮糖的方法
WO2020205978A1 (fr) * 2019-04-01 2020-10-08 The Coca-Cola Company Compositions contenant de la brazzéine
CN115250612A (zh) * 2020-06-03 2022-10-28 弗门尼舍有限公司 用于减少异味的组合物及其用途
US11918675B2 (en) 2019-12-16 2024-03-05 Colgate-Palmolive Company Oral care compositions

Citations (3)

* Cited by examiner, † Cited by third party
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
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109022625A (zh) * 2018-09-18 2018-12-18 上海立足生物科技有限公司 一种生产浓缩的d-阿洛酮糖的方法
WO2020205978A1 (fr) * 2019-04-01 2020-10-08 The Coca-Cola Company Compositions contenant de la brazzéine
CN113939197A (zh) * 2019-04-01 2022-01-14 可口可乐公司 含有布拉齐因的组合物
US11918675B2 (en) 2019-12-16 2024-03-05 Colgate-Palmolive Company Oral care compositions
CN115250612A (zh) * 2020-06-03 2022-10-28 弗门尼舍有限公司 用于减少异味的组合物及其用途

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