WO2016130609A1 - Production biosynthétique de rébaudioside m et procédés de récupération - Google Patents

Production biosynthétique de rébaudioside m et procédés de récupération Download PDF

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Publication number
WO2016130609A1
WO2016130609A1 PCT/US2016/017236 US2016017236W WO2016130609A1 WO 2016130609 A1 WO2016130609 A1 WO 2016130609A1 US 2016017236 W US2016017236 W US 2016017236W WO 2016130609 A1 WO2016130609 A1 WO 2016130609A1
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WIPO (PCT)
Prior art keywords
rebaudioside
mogroside
glycoside
terpenoid glycoside
terpenoid
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PCT/US2016/017236
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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 BR112017017207-0A priority Critical patent/BR112017017207B1/pt
Priority to EP16749758.5A priority patent/EP3256008A4/fr
Priority to CN201680017221.7A priority patent/CN107404911A/zh
Priority to US15/550,075 priority patent/US20180020709A1/en
Priority to MX2017010311A priority patent/MX2017010311A/es
Publication of WO2016130609A1 publication Critical patent/WO2016130609A1/fr
Priority to US16/467,805 priority patent/US20210368839A1/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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/54—Mixing with gases
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1048—Glycosyltransferases (2.4)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1048—Glycosyltransferases (2.4)
    • C12N9/1051—Hexosyltransferases (2.4.1)
    • C12N9/1074—Cyclomaltodextrin glucanotransferase (2.4.1.19)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/24—Hydrolases (3) acting on glycosyl compounds (3.2)
    • C12N9/2402—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/24—Hydrolases (3) acting on glycosyl compounds (3.2)
    • C12N9/2402—Hydrolases (3) acting on glycosyl compounds (3.2) hydrolysing O- and S- glycosyl compounds (3.2.1)
    • C12N9/2405—Glucanases
    • C12N9/2408—Glucanases acting on alpha -1,4-glucosidic bonds
    • C12N9/2411—Amylases
    • C12N9/2428—Glucan 1,4-alpha-glucosidase (3.2.1.3), i.e. glucoamylase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin

Definitions

  • 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 CI 9 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, F, G, H, I, J K, L, M, N, and O, Steviolbioside, Dulcoside A and Rubusoside are found at lower levels (approx. 0-0.5%).
  • Rebaudioside M (also known as Rebaudioside X; CAS No: 1220616-44-3) is one of minor steviol glycosides found in Stevia rebaudicma plant. It was found to have superior taste properties and is a highly desirable natural high intensity sweetener (WO2013/096420 007748 incorporated herein as a reference, in its entirety).
  • FIG. 1 shows a high-performance liquid chromatographic (HPLC) chromatogram of Rebaudioside M
  • FIG. 3 shows a HPLC chromatogram of glucoamylase treated -l ,4-glucosyl- derivatives of Rebaudioside M.
  • the present invention is aimed to overcome the disadvantages of existing processes for producing steviol glycoside(s) found in Stevia rebaudiana plant by recombinant microorganism(s).
  • the invention relates to a process for producing steviol glycoside(s) found in Stevia rebaudiana plant by recombinant microorganism(s) and recovering the produced glycoside(s) for use in various food products and beverages as sweetener, sweetness enhancer, flavor, flavor modifier/enhancer.
  • the invention in part, pertains to a process of producing steviol glycosides found in Stevia rebaudiana plant by fermentation of recombinant microorganism(s).
  • the process of invention may include a step of adding solvent comprising alcohol to any media obtainable from downstream processing of fermentation media of recombinant host(s).
  • said media comprises separated recombinant microorganism(s) cells (cell debris) and crystalline steviol glycosides.
  • the alcohol may be selected from the group including but not limited to methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, and combinations thereof.
  • the alcohol may be in a form of aqueous solution or anhydrous.
  • the process of invention may include a step of producing -glycosylated derivatives of steviol glycosides found in Stevia rebaudiana plant wherein said a- glycosylated derivatives contain at least one -glycosyl residue in their molecule.
  • the process of invention may include a further step of selective hydrolysis of a- glycosydic bond(s) to convert -glycosylated derivatives of steviol glycosides to steviol glycosides found in Stevia rebaudiana plant.
  • the invention in part, pertains to a composition comprising a-glycosylated derivatives of steviol glycosides found in Stevia rebaudiana plant.
  • the process comprises an enzymatic a-glycosylation step.
  • the a-glycosylation step can occur within the recombinant host cell, on the surface of the recombinant host cell, or outside the recombinant host cell.
  • the ⁇ -glycosylation is achieved by a-glycosyltransferase(s) and nucleotide glycosyl donor.
  • the ⁇ -glycosylation is achieved by a- glycosyltransferase(s) and non-nucleotide glycosyl donor.
  • cyclomaltodextrin glucanotransferase (CGTase; EC 2.4.1.19) enzyme(s) and starch (as glucose donor) were used to produce a-l ,4-glucosyl-derivatives of steviol glycosides containing at least one a-l ,4-glucosyl residue in their molecules.
  • the enzyme(s) for -glycosyl-derivatives synthesis may be also incorporated into any recombinant host capable of producing steviol glycosides molecules found in Stevia rebaudiana plant.
  • the obtained a-glycosyl-derivatives have higher water solubility and hence do not precipitate.
  • the microbial cells (cell debris) removal results in no or minimal loss of product.
  • the a- 1 ,4-glucosyl-derivatives dissolved in supernatant are hydrolyzed by glucoamylase for selective hydrolysis of a-l ,4-glucosidic bonds and conversion of a-l ,4-glucosylated derivatives of steviol glycosides to steviol glycosides molecules found in Stevia rebaudiana plant.
  • transglucosylation was accomplished by CGTase of Bacillus stearothermophilus St- 100 (PureCircle Sdn Bhd Collection of Industrial Microorganisms - Malaysia).
  • 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.
  • donors of glucosyl residues such as maltodextrins, cyclodextrins etc may be used as well.
  • One unit of glucoamylase activity is defined as the amount of glucoamylase that will liberate 0.1 ⁇ / min of /j-nitrophenol from the PNPG Solution under the conditions of the assay described in Food Chemicals Codex 5 th ed., p. 907.
  • the reaction mixture may be further concentrated by vacuum evaporator and/or dried by means of a spray dryer.
  • Other appropriate concentrating and drying methods such as membrane filtration, freeze drying, or other methods known to art can be used.
  • the steviol glycosides from obtained reaction mixture may be recovered by any method or combination of methods known to art for extraction, separation, purification, isolation and production of steviol glycosides found in Stevia rebaudiana plant.
  • Non limiting examples of such methods include extraction by water and or organic solvents, treatment with flocculants, coagulants, treatment with macroporous adsorption resins, ion- exchange resin treatment, activated carbon treatment, membrane filtration, RO-membrane filtration, microfiltration, nanofiltration, ultrafiltration, chromatography, HPLC, SMB- chromatography, supercritical fluid (SF) chromatography, adsorption resin chromatography, multicolumn adsorption chromatography, ion-exchange chromatography, continuous chromatography, supercritical fluid extraction, ultrasound assisted extraction, microwave assisted extraction, enzyme assisted extraction, solid-liquid extraction, liquid- liquid extraction, crystallization, ultrasound assisted crystallization, gradient crystallization, solvent-antisolvent crystallization, co-crystallization, centrifugation,
  • the obtained purified steviol glycoside(s) can be used as sweeteners, sweetness enhancers, flavor enhancers and flavor modifiers in various 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, 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.
  • the obtained purified steviol glycoside(s) 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 obtained purified steviol glycoside(s) can be used "as-is” or in combination with other sweeteners, flavors, flavor ingredients and food ingredients.
  • Non-limiting examples of sweeteners include steviol glycosides, 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, dulcoside A, steviolbioside, rubusoside, steviolmonoside as well as any other steviol glycoside(s) found in Stevia rebaudiana plant and mixtures thereof, stevia extract, glycosylated steviol glycosides, Luo Han Guo extract, mogrosides, high-fructose corn syrup, corn syrup, invert sugar, fructooligosaccharides, inulin, inulooligosaccharides, coupling sugar, maltooligosaccharides, maltodextrins, corn syrup solids, glucose, maltose, sucrose, lac
  • Non-limiting examples of other food ingredients include flavors, acidulants, organic and amino acids, coloring agents, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilisers, thickeners, gelling agents.
  • flavors, acidulants, organic and amino acids coloring agents, bulking agents, modified starches, gums, texturizers, preservatives, antioxidants, emulsifiers, stabilisers, thickeners, gelling agents.
  • a strain of Bacillus stearothermophiliis St-100 was inoculated in 2,000 liters of sterilized culture medium containing 1.0% starch, 0.25% corn extract, 0.5% (NH 4 ) 2 S0 4 , 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 2-fold on Persep l OkDa ultrafilters (Orelis, France).
  • the activity of the enzyme was determined according to Hale, Rawlins (1951 ). A crude enzyme preparation with activity of about 2 unit/mL was obtained.
  • Bhd. (Malaysia), having water solubility of 0.5g/L (at 25°C) and containing 96.97% Reb M and 3.03% Reb D, was dissolved by boiling in 9,000 mL of water (pH was adjusted to pH 6.0) and was added to liquefied starch and stirred until a homogeneous solution was obtained. 200 units of CGTase was added to the solution and the mixture was held at a temperature of 65°C for 24 hours under continuous agitation. The obtained reaction mixture was heated at 95°C for 15 minutes to inactivate the enzyme. 20 grams of activated carbon was added and the mixture was heated to 75°C and held during 30 min.
  • the same method can be used to prepare juices and juice drinks from other fruits, such as apples, lemons, apricots, cherries, pineapples, mangoes, etc.
  • a carbonated beverage according to formula presented below was prepared.
  • the sensory properties were evaluated by 20 panelists. The best results were obtained in samples prepared with Reb M. The panelists noted rounded and complete flavor profile and mouthfeel in cookies prepared with Reb M.

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Abstract

La présente invention concerne divers procédés de récupération pour la récupération complète de glycosides de stéviol peu solubles obtenus dans des micro-organismes de recombinaison. Des glycosides de stéviol α-glycosyl solubles ont été entièrement récupérés dans un traitement en aval puis convertis en glycosides de stéviol par des hydrolases. Les glycosides de stéviol obtenus ont été purifiés et utilisés en tant qu'édulcorants, exhausteurs de goût sucré, exhausteurs de goût et modificateurs de goût dans des aliments, des boissons, des produits cosmétiques et des produits pharmaceutiques.
PCT/US2016/017236 2005-10-11 2016-02-10 Production biosynthétique de rébaudioside m et procédés de récupération WO2016130609A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BR112017017207-0A BR112017017207B1 (pt) 2015-02-10 2016-02-10 Processo para produzir um glicosídeo terpenoide, composição de sabor, ingrediente alimentício, alimento, bebida ou outro produto consumível, cosmético e produto farmacêutico que compreende o dito glicosídeo terpenoide
EP16749758.5A EP3256008A4 (fr) 2015-02-10 2016-02-10 Production biosynthétique de rébaudioside m et procédés de récupération
CN201680017221.7A CN107404911A (zh) 2015-02-10 2016-02-10 莱鲍迪苷m生物合成生产和回收方法
US15/550,075 US20180020709A1 (en) 2014-04-16 2016-02-10 Rebaudioside m biosynthetic production and recovery methods
MX2017010311A MX2017010311A (es) 2015-02-10 2016-02-10 Metodos de produccion y recuperacion de rebaudiosido m biosintetico.
US16/467,805 US20210368839A1 (en) 2005-10-11 2017-12-08 Glucosyl stevia compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562114134P 2015-02-10 2015-02-10
US62/114,134 2015-02-10

Related Parent Applications (1)

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US14/254,653 Continuation-In-Part US9386797B2 (en) 2005-10-11 2014-04-16 Glucosyl stevia composition

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US15/550,075 A-371-Of-International US20180020709A1 (en) 2014-04-16 2016-02-10 Rebaudioside m biosynthetic production and recovery methods
PCT/US2017/065235 Continuation-In-Part WO2018106983A1 (fr) 2005-10-11 2017-12-08 Compositions de stevia glucosylé

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EP (1) EP3256008A4 (fr)
CN (1) CN107404911A (fr)
BR (1) BR112017017207B1 (fr)
MX (1) MX2017010311A (fr)
WO (1) WO2016130609A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
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CN106554983A (zh) * 2016-10-28 2017-04-05 江南大学 甜菊糖杜克苷a的制备方法
WO2017171023A1 (fr) * 2016-03-31 2017-10-05 サントリーホールディングス株式会社 Boisson dans laquelle la précipitation de l'hespéridine a été inhibée
WO2018044588A1 (fr) * 2016-08-29 2018-03-08 Pepsico, Inc. Compositions contenant du rébaudioside j
WO2018165330A1 (fr) * 2017-03-08 2018-09-13 Purecircle Usa Inc. Cultivars de plantes de stévia à teneur élevée en rébaudioside m et leurs procédés de production
EP3597656A4 (fr) * 2017-03-16 2020-12-09 Zhucheng Haotian Pharm Co., Ltd. Forme cristalline m de stévioside, son procédé de préparation et son utilisation
US11060124B2 (en) 2017-05-03 2021-07-13 Firmenich Incorporated Methods for making high intensity sweeteners
US11066688B2 (en) 2015-07-10 2021-07-20 Dsm Ip Assets B.V. Method for preparing a steviol glycoside composition
US11357246B2 (en) 2015-10-29 2022-06-14 Firmenich Incorporated High intensity sweeteners
US11571011B2 (en) 2015-07-10 2023-02-07 Sweet Green Fields International Co., Limited Compositions of steviol multiglycosylated derivatives and stevia components

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021514607A (ja) * 2018-02-26 2021-06-17 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ グルコシル化テルペングリコシド、テルペングリコシドおよびシクロデキストリンを含む組成物
CN108707163B (zh) * 2018-06-11 2020-08-14 江西师范大学 一种甜菊醇甙元的制备方法
CA3171399A1 (fr) * 2020-03-13 2021-09-16 Stanley W. HERRMANN Compositions d'edulcorant a base de rebaudioside m

Citations (6)

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US4219571A (en) 1978-06-15 1980-08-26 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Process for producing a sweetener
US20090162487A1 (en) * 2007-12-21 2009-06-25 The Concentrate Manufacturing Company Of Ireland Beverage products and flavor systems having a non-sweetening amount of rebaudioside a
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BR112017017207B1 (pt) 2022-10-18
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