WO2008129457A1 - Processus de préparation d'extrait de jus sucré - Google Patents

Processus de préparation d'extrait de jus sucré Download PDF

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Publication number
WO2008129457A1
WO2008129457A1 PCT/IB2008/051430 IB2008051430W WO2008129457A1 WO 2008129457 A1 WO2008129457 A1 WO 2008129457A1 IB 2008051430 W IB2008051430 W IB 2008051430W WO 2008129457 A1 WO2008129457 A1 WO 2008129457A1
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WO
WIPO (PCT)
Prior art keywords
extract
filter
retentate
permeate
molecular weight
Prior art date
Application number
PCT/IB2008/051430
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English (en)
Inventor
Eric Frerot
Original Assignee
Firmenich Sa
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 Firmenich Sa filed Critical Firmenich Sa
Publication of WO2008129457A1 publication Critical patent/WO2008129457A1/fr

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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
    • A23L2/70—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter
    • A23L2/72—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter by filtration
    • A23L2/74—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter by filtration using membranes, e.g. osmosis, ultrafiltration
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/156—Flavoured milk preparations ; Addition of fruits, vegetables, sugars, sugar alcohols or 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
    • 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

Definitions

  • the present invention relates to a process for preparing a very sweet extract from the juice of one or more plants in the Cucurbitaceae family and to an extract prepared according to this process.
  • terpene glycosides are natural materials, which provide a level of sweetness often many times more powerful than that of natural sugar but with the added distinction of negligible calories.
  • a further advantage is that they are natural and so avoid the need for artificial sweeteners.
  • mogrosides IV and V 11-oxo-mogroside V, and siamenoside I have been identified and characterized chemically as the very sweet components. See for example, Matsumoto, et al, Chem. Pharm. Bull, 38 (7), 2030-2032 (1990).
  • Luo Han Guo The best known, and most common fruit from the Cucurbitaceae family is Luo Han Guo, which is produced by the plant S. grosvenorii found in southern China.
  • the fresh fruit can be used for sweetening many kinds of foodstuffs and beverages but it is prone to decomposition if stored. To address this, it is typically treated by being slowly dried in an oven prior to be added to the product to be sweetened. Even so, the dried fruit still has an earthy, beany, vegetable flavour and a tendency to form off flavours, particularly bitter, astringent and browned flavours.
  • the undesirable flavours have often been described as liquorice, vegetal and/or caramelic. Such flavours restrict the use of the dried fruits and dried fruit extracts to the preparation of dilute teas and soups and products to which sugar, honey and the like are added.
  • the juices can simply be extracted from the fruit and used as such.
  • such juice has a slightly acidic pH and contains sugars, which can brown and ferment creating an aesthetically displeasing product.
  • the juice is often concentrated by evaporation processes which involve heating the juice, usually under vacuum. Nevertheless, this creates the same off- flavours as when the fruit itself is dried.
  • the loss of certain desirable components, and, in particular, certain mogrosides is also inevitable. It would be desirable to provide an extract that avoids some or all of these disadvantages.
  • US 5,433,965 (Procter and Gamble) relates to beverages that are sweetened using Luo Han Guo juice and discloses, in example 5, a process for preparing the juice.
  • the steps include mashing the pulp by hand, passing through a strainer, acidifying the permeate, passing through a 20 mesh screen and evaporating the juice.
  • the last step is performed in order to remove volatile off-flavour precursors.
  • the section relating to removal of off- flavour precursors states that evaporation; addition of a fining agent, adsorbent or precipitating agent to the juice fo llowed by removal of the resulting agent/precipitate preferably by filtration or centrifugation; and use of activated charcoal are all to be used to remove off- flavour materials and precursors thereof.
  • US 5,411,755 similarly relates to a process wherein the Luo Han Guo juice is treated by removal of pulp solids and use of ion exchange resins, fining agents, adsorbents, enzymes and precipitating agents to remove off-note precursors.
  • the process is complicated in that it requires volatilisation of certain ingredients using expensive vacuum evaporation technology.
  • mechanical filtration is used to remove the agents which have been previously added in order to remove off-flavours and their precursors. Mechanical filtration is not considered as the means directly to remove the off-flavours and their precursors. It would be desirable to provide an effective process which avoids the very complicated systems disclosed in these documents.
  • US 6,124,442 (Zhou et al) relates to a multiple step process for extracting triterpene glycosides from juices in general, using macroporous resins combined with washing with ethanol.
  • WO-A-94/18855 (Procter and Gamble) relates to the use of Luo Han Guo (and some other species) as sweetening agents.
  • the present invention provides a process for preparing a sweet juice extract comprising the steps of: (a) preparing a liquid comprising the extract of the fruit of one or more plants from the
  • step (b) passing the liquid extract through a first filter having a molecular weight cut off equal to or greater than 1 '5OO Da, and optionally repeating step (b) to obtain a first permeate and a first retentate,
  • the invention further provides a liquid or solid, preferably powdered extract prepared according to the process above.
  • the invention also provides a food or beverage product comprising a liquid or solid, preferably powdered extract prepared according to the process.
  • MWCO Molecular weight cut off
  • Da Daltons
  • a liquid is prepared comprising the extract of the fruit of one or more plants in the Cucurbitaceae family.
  • the process is carried out on the extract of the fruit of one or more plants in the Cucurbitaceae family, tribe Jollifieae, subtribe Thladianthinae, genus Siraitia.
  • the genus/species S. grosvenorii S. siamensis, S. silomaradjae, S. sikkimensis, S. africana, S. borneensis, and S. taiwaniana.
  • the most preferred fruit is derived from the genus/species S. grosvenorii, which is often called Luo Hah Guo fruit.
  • the process is applicable to other sweet fruit juices of Cucurbitaceae family which contain at least 0.01% sweet triterpene glycosides or mogrosides.
  • the juices will contain from 0.1% to about 15% mogrosides, preferably mogroside V, mogroside IV, (11-oxo-mogroside V) siamenoside and mixtures thereof.
  • mogroside V is the key active ingredient for providing the sweet flavour and has the formula:
  • powdered instant Luo Han Guo is commercially available from suppliers such as Guilin Layn or the Yongfu Company, both of which are based in China.
  • the liquid extract is simply prepared by addition of a suitable solvent, typically a water/ethanol mixture in a 5:1 to 15:1 ratio, followed by stirring until the powder has dissolved.
  • a first filtration is carried out using a filter that has an MWCO point equal to or greater 1 '5OO Da, more preferably equal to or greater than 2'500 Da, most preferably equal to or greater than 3'00O Da. That is, materials having a molecular weight of 1 '500 Da or more, more preferably 2'500 or more, most preferably 3'00O or more will be retained as retentate and particles having a molecular weight inferior thereto will pass into the permeate.
  • the filter is preferably a membrane filter, also known as assize exclusion membrane filter.
  • the first filtration removes various proteinacious and high molecular weight materials. Most importantly, this simple yet surprisingly effective step removes a significant proportion of the off-flavours and colours without substantially reducing the level of mogrosides.
  • the proteinacious and high molecular weight materials are also responsible for generating further off-odours during any subsequent drying process.
  • Step (b) may be performed more than once. In this case, additional aliquots of solvent are passed through the filter to collect more permeate and to allow a greater proportion of desirable mogrosides to pass through the filter.
  • step (b) can be repeated from 2 to 20 times, more preferably from 3 to 10 times, most preferably from 4 to 9 times in order to obtain the first permeate and first retentate. It has been found that step (b) gives improved yields when performed under diafiltration conditions.
  • step (b) is performed at elevated pressure, so that the liquid to be filtered passes more readily through the filter. For instance, a pressure of 1.2 to 8 bar, more preferably 1.3 to 6 bar, most preferably 1.8 to 3 bar is applied during this step.
  • step (b) comprises ultrafiltration.
  • Ultrafiltration (UF) comprises membrane filtration in which hydrostatic pressure forces a liquid against a semipermeable membrane and advantageously allows for a very precise separation of desirable materials from undesirable materials based on their respective molecular weights.
  • the first filtration preferably removes substantially all of the proteinacious materials, it allows a significant amount of mogrosides to pass into the permeate. Thus, it is preferred that at least 85%, more preferably 90% of the mogrosides pass through the filter into the permeate.
  • step (b) of the present invention The use of a first filter having a cut-off below 1 '5OO Da is not suitable for use in step (b) of the present invention since it has been found that the loss of mogrosides into the retentate is increased dramatically, thereby reducing unacceptably the sweetening effect of the final product.
  • a second different filtration step is required. This step is performed on the permeate obtained in step (b).
  • the filter has an MWCO equal to or less than 1 '0OO Da. That is, materials having a molecular weight of greater than 1 OOO Da will be retained as retentate and particles having a molecular weight inferior thereto will pass into the permeate.
  • the filter is preferably a membrane filter.
  • the small molecular weight components, and in particular, the free volatile components, are not retained by the filter but pass through into the permeate. It has been found that with an MWCO of 1 OOO Da, the components that are significantly responsible for the off-odour are not retained with the mogrosides, which are held in the retentate.
  • the second filtration step preferably removes at least 90% by weight of sotolone, methyl mercaptan, dimethyl sulphide and dimethyl disulphide that was present in the extract obtained in step (a).
  • the retentate comprises the concentrated mogrosides but is substantially free of components which adversely affect flavour and storage stability.
  • Step (c) has been found to increase the level of total mogrosides in the final retentate to 30% or more, more preferably 35% or more, even more preferably 50% or more, most preferably 60% or more, based on the total dry weight of the extract.
  • the level of mogroside V in the final retentate is preferably 20% or more, more preferably 25% or more, even more preferably 30% or more, most preferably 40% or more, based on the total dry weight of the extract.
  • the mogroside V content in the retentate is preferably more than 50%, more preferably more than 60%, most preferably more than 70% by weight, based on the total weight of all mogrosides present in the retentate.
  • liquorice off- flavour usually associated with this type of extract is substantially avoided.
  • step (c) is performed at elevated pressure, so that the liquid to be filtered passes more readily through the filter.
  • a pressure of 1.2 to 8 bar, more preferably 1.3 to 6 bar, most preferably 1.8 to 3 bar is applied during this step.
  • step (c) comprises ultrafiltration Whilst, in theory, step (c) could be performed prior to step (b), it has surprisingly been found that this is not suitable in the context of the present invention since the removal of sufficient off-note compounds from the extract is not achieved and the end product has an unacceptable aroma profile.
  • the extract, in the form of the second retentate obtained according to step (c) can be used without additional treatment. In this case, it is limited in its use to the sweetening of final products that are liquid or pasty. Nevertheless, it is typically desirable to dry the retentate so that it can be stored and transported more easily. Additionally, it can then be used to sweeten foods which require ingredients in a solid form.
  • the drying step preferably provides a solid product, more preferably a powdered product.
  • the drying step does not generate the off-odours typically associated with prior art drying processes that are carried out on the extract directly obtained from the plant without the intervening steps.
  • Any suitable process for drying can be used such as heating gently subjecting the retentate to reduced pressure (e.g. a vacuum), spray-drying and the like.
  • a particularly preferred process involves the step of freeze-drying.
  • the sweet juice extract prepared according to the process of the present invention can be used to provide natural sweetness for many purposes.
  • beverages such as tea, coffee, fruit juice and fruit- flavoured beverages
  • foods such as jams and jellies, peanut butter, pies, puddings, cereals, candies, ice creams, yogurts, bakery products
  • health care products such as toothpastes, mouthwashes, cough drops, cough syrups; chewing gums; and sugar substitutes.
  • the extract may be present in an amount of from 0.0001% to 0.1%, more preferably from 0.001 to 0.05%, most preferably from 0.003 to 0.03%, e.g. from 0.004 to 0.015%, by weight of dry extract based on the total weight of the food.
  • sample 1 Preparation of sweetness-enhancing extracts 5O g of powdered Luo Han Guo extract (ex Guilin Layn Natural Ingredients Corporation, China), herein referred to as "sample 1", were dissolved in 270 ml of deionized water and 30 ml of ethanol. The solution was poured into a 400 ml Amicon filtration cell containing a YM-3 modified cellulose filter with an MWCO of 3'00O Da. Ultrafiltration was performed under 2.5 bar of nitrogen. After 300ml of the solution had passed through the filter, a further 300 ml of solvent (water and ethanol at a 9:1 ratio) was added and ultrafiltration under nitrogen carried out. The batchwise filtration process was repeated until 2.1 litres of permeate had been recovered. In order to assess the quantity of dissolved material present in the permeate, The permeate was freeze-dried to yield 38.4 g (77%) of solid product (referred to herein as "sample 2").
  • sample 2 20 g of sample 2 were dissolved in 180 ml of deionised water and 20 ml of ethanol. The solution was poured into a 400 ml Amicon filtration cell containing a YM-I modified cellulose filter having an MWCO of 1 '0OO Da. Ultrafiltration was performed under 2.5 bar of nitrogen. In this step, 2 litres of solvent (1800ml deionised water and 200ml ethanol) was transferred in a continuous process from a reservoir into the filtration cell and through the filter. The transfer rate was monitored to ensure that a constant volume was present in the cell. After the 2 litres of solution had passed through the filter, the retentate remaining in the cell was collected and freeze-dried to yield a light brown powder (7.7 g, 38.6%), herein referred to as "sample 3".
  • solvent 1800ml deionised water and 200ml ethanol
  • the total yield from sample 1 to sample 3 was 29.7% yield w/w.
  • Trial 7 had a round sweetness and strongest off-notes described as mushroom, nutty, woody and slightly liquorice. Trial 8 was found sweeter than trial 7 but still with significant detectable off-notes. Trial 9 was found to deliver the most significant sweetness both in terms of intensity and "clean" sucrose-like sweet taste.
  • a sweetened yoghurt base was prepared by stirring sucrose into an unflavoured yoghurt (3.8wt% fat) to provide a sucrose level of 7wt%.
  • the base was kept at 5°C overnight.
  • the various solutions were then incorporated into the yoghurt base with stirring in the amounts given in the table below.
  • the yoghurt products were kept at 5°C for 5 days prior to evaluation by a panel of 3 expert flavourists.
  • Samples 1 and 3 were each dissolved in warm propylene glycol (45°C) to provide a l%w/w solution.
  • a low- fat (0.5wt% fat) UHT milk mixture was prepared by mixing fat-free UHT milk with semi-skimmed milk and 3.5wt% sucrose in a weight ratio of7:13:l.
  • Sweetening compounds were then mixed into the low-fat dairy drink in the amounts shown to provide sweetened drinks.
  • Each drink was divided into a first sample, which was stored at 5°C and a second sample, which underwent a pasteurisation step.
  • Pasteurisation was carried out using a pilot scale UHT indirect 4 section plate exchanger at constant flow-rate (20 litre/hour with following parameters: preheating 70 0 C; UHT temperature 135°C; precooling 70 0 C; cooling 5°C).
  • the pasteurised product was then filled into sterile PET bottles and stored at 5°C. All drinks were evaluated at room temperature by a panel of 4 expert flavourists.
  • a regular Cola syrup was prepared by admixing the following ingredients: Table 4
  • the syrup was then divided into two portions. Into one portion, lOOppm of sample 3 was added with stirring. The other portion was left unchanged. Carbonated water was then added with mixing to each portion in a weight ratio of 1 part syrup to 5 parts carbonated water.
  • a diet Cola syrup was prepared by admixing the following ingredients:
  • the syrup was then divided into two portions. Into one portion, lOOppm of sample 3 was added with mixing. The other portion was left unchanged. Carbonated water was then added with mixing to each portion in a weight ratio of 1 part syrup to 5 parts carbonated water.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Water Supply & Treatment (AREA)
  • Microbiology (AREA)
  • Seasonings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention concerne un extrait de jus sucré fabriqué (a) en préparant un liquide comprenant l'extrait de fruit d'une ou plusieurs plantes de la famille des curcubitacées, (b) en passant l'extrait de liquide à travers un premier filtre présentant un seuil de coupure de poids moléculaire supérieur ou égal à 1 500 Da de manière à obtenir un premier perméat et un premier retentat, (c) en passant le premier perméat à travers un second filtre présentant un seuil de coupure de poids moléculaire inférieur ou égal à 1 000 Da de manière à obtenir un second perméat et un second retentat, et (d) en séchant de manière optionnelle le second retentat de manière à obtenir un solide, de préférence un extrait sucré en poudre.
PCT/IB2008/051430 2007-04-18 2008-04-15 Processus de préparation d'extrait de jus sucré WO2008129457A1 (fr)

Applications Claiming Priority (2)

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EP07106367.1 2007-04-18
EP07106367 2007-04-18

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008149253A2 (fr) 2007-06-07 2008-12-11 Firmenich Sa Composition édulcorante naturelle
EP2090181A1 (fr) * 2008-02-04 2009-08-19 Kraft Foods Global Brands LLC Matériaux thermoplastiques comportant des agents de transfert de charge et agents de génération de photo-acide
US11464247B2 (en) 2006-09-07 2022-10-11 Guilin Gfs Monk Fruit Corp. Sweetening compositions and processes for preparing them
US11576412B2 (en) 2016-10-24 2023-02-14 Guilin Gfs Monk Fruit Corporation Extracts from fruits of the Cucurbitaceae family, and methods of preparing thereof

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US4511559A (en) * 1982-03-04 1985-04-16 Kozponti Valto-es Hitelbank Rt. InnovacioAlap Biologically active polysaccharide concentrates and process for production of preparates containing such substances
WO1994018854A2 (fr) * 1993-02-16 1994-09-01 The Procter & Gamble Company Procede et composition s'appliquant a la preparation de jus de fruits obtenus a partir de fruits de la famille cucurbitacees
WO1994018855A1 (fr) * 1993-02-16 1994-09-01 The Procter & Gamble Company Boissons sucrees et compositions edulcorantes
US6103240A (en) * 1999-02-05 2000-08-15 Zhou; James H. Herbal sweetening and preservative composition comprising licorice extract and mogrosides obtained from plants belonging to cucurbitaceae and/or momordica
US6124442A (en) * 1999-03-24 2000-09-26 Zhou; James H. Process for extracting triterpene glycosides from botanical sources
US20030157229A1 (en) * 1997-12-01 2003-08-21 Blumenstein-Stahl Gabriele Annemarie Beverage comprising an effective amount of flavanols as sweetness cutting composition
US20060003053A1 (en) * 2004-06-30 2006-01-05 The Procter & Gamble Company Method for extracting juice from plant material containing terpene glycosides and compositions containing the same

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US4511559A (en) * 1982-03-04 1985-04-16 Kozponti Valto-es Hitelbank Rt. InnovacioAlap Biologically active polysaccharide concentrates and process for production of preparates containing such substances
WO1994018854A2 (fr) * 1993-02-16 1994-09-01 The Procter & Gamble Company Procede et composition s'appliquant a la preparation de jus de fruits obtenus a partir de fruits de la famille cucurbitacees
WO1994018855A1 (fr) * 1993-02-16 1994-09-01 The Procter & Gamble Company Boissons sucrees et compositions edulcorantes
US5411755A (en) * 1993-02-16 1995-05-02 The Procter & Gamble Company Process and composition for sweet juice from cucurbitaceae fruit
US5433965A (en) * 1993-02-16 1995-07-18 The Procter & Gamble Company Beverage compositions and sweetening compositions which contain juice derived from botanical subfamily Cucurbitaceae
US20030157229A1 (en) * 1997-12-01 2003-08-21 Blumenstein-Stahl Gabriele Annemarie Beverage comprising an effective amount of flavanols as sweetness cutting composition
US6103240A (en) * 1999-02-05 2000-08-15 Zhou; James H. Herbal sweetening and preservative composition comprising licorice extract and mogrosides obtained from plants belonging to cucurbitaceae and/or momordica
US6124442A (en) * 1999-03-24 2000-09-26 Zhou; James H. Process for extracting triterpene glycosides from botanical sources
US20060003053A1 (en) * 2004-06-30 2006-01-05 The Procter & Gamble Company Method for extracting juice from plant material containing terpene glycosides and compositions containing the same

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KATSUHIRO MATSUMOTO ET AL: "Minor Cucurbitane-Glycosides from fruits of Siraitia grosvenori (Cucurbitaceae)", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, TOKYO, JP, vol. 38, no. 7, 1990, pages 2030 - 2032, XP002122307, ISSN: 0009-2363 *
KINGHORN, A.D. ET AL: "Discovery of terpenoid and phenolic sweeteners from plants", PURE APPL.CHEM., vol. 74, no. 7, 2002, pages 1169 - 1179, XP002455090 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11464247B2 (en) 2006-09-07 2022-10-11 Guilin Gfs Monk Fruit Corp. Sweetening compositions and processes for preparing them
WO2008149253A2 (fr) 2007-06-07 2008-12-11 Firmenich Sa Composition édulcorante naturelle
EP2090181A1 (fr) * 2008-02-04 2009-08-19 Kraft Foods Global Brands LLC Matériaux thermoplastiques comportant des agents de transfert de charge et agents de génération de photo-acide
US8263162B2 (en) 2008-02-04 2012-09-11 Kraft Foods Global Brands Llc Natural sweetener and methods of manufacturing thereof
US11576412B2 (en) 2016-10-24 2023-02-14 Guilin Gfs Monk Fruit Corporation Extracts from fruits of the Cucurbitaceae family, and methods of preparing thereof

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