WO2006108626A1 - Sustained energy release compositions - Google Patents
Sustained energy release compositions Download PDFInfo
- Publication number
- WO2006108626A1 WO2006108626A1 PCT/EP2006/003357 EP2006003357W WO2006108626A1 WO 2006108626 A1 WO2006108626 A1 WO 2006108626A1 EP 2006003357 W EP2006003357 W EP 2006003357W WO 2006108626 A1 WO2006108626 A1 WO 2006108626A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- glucopyranosyl
- tetritol
- energy release
- erythritol
- feed
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/163—Sugars; Polysaccharides
-
- 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
- A23L27/34—Sugar alcohols
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
- A23L29/37—Sugar alcohols
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to the use of certain specified carbohydrate materials in the preparation of sustained glucose and energy release food, feed and drink compositions and to compositions containing such materials.
- Carbohydrates are formed of monomer units such as glucose, fructose and galactose. Many carbohydrates are linked to each other by ⁇ -l,4-glucosidic bonds that are easily hydrolysed during the early stages of digestion in both humans and animals (i.e. in the mouth, stomach and small intestine). Examples of such carbohydrates include the commercially available hydrolysis products of starch, such as maltose and maltodextrins. It is common knowledge that oral ingestion of such carbohydrates leads to a rapid increase in blood glucose concentration and therefore to an elevated insulin response. This is typically followed by a sharp decrease in blood glucose and, because insulin levels remain high, can result in so called "rebound hypoglycaemia". Symptoms of hypoglycaemia include nausea, weakness, hallucinations, headaches, hypothermia and fainting.
- hypoglycaemia blood glucose
- tissue insulin sensitivity tissue insulin sensitivity
- Such prolonged hyperglycaemia induces undesired effects on metabolism in the body often referred to as metabolic syndrome, a combination of several disease risk factors such as elevated blood pressure, impaired glucose tolerance, elevated fasting blood glucose and impaired blood lipid levels, often together with weight gain. Being exposed to these risk factors is known to lead to a significant increase in morbidity and mortality.
- carbohydrate compounds that can be safely ingested whilst retaining the desirable properties (such as sweetness) of more conventional carbohydrates (e.g. glucose, maltose, maltodextrins and sucrose).
- a number of high intensity sweeteners have been proposed for helping to reduce the increase in blood glucose, when being substituted for absorbable glucose sources, including, for example, aspartame, saccharin, sucralose or cyclamate.
- these sweeteners cannot be used as effective sources of glucose and energy required for maintenance of a normal cellular function of the central nervous system and red blood cells.
- a consistent supply of glucose is an important characteristic, e.g. in nutritional compositions used by highly active people (such as sports men and women) or by certain categories of patients that have a particularly high energy turnover (burn patients, for example).
- the problem to be solved by the present invention is therefore the provision of a carbohydrate material that does not cause rebound hypoglycaemia whilst nevertheless having high sweetness and being a consistent source of glucose and energy.
- Proposed solutions include carbohydrates such as isomaltulose, certain dextrans and pullulan. All of these carbohydrates, however, have a number of drawbacks. Taking isomaltulose by way of example, although its digestion results in a slow release of glucose into the blood it only has a relatively low sweetness (42% the sweetness of sucrose), it is not very heat or acid stable (stability being a particularly desirable characteristic for compounds used in food compositions) and it has a relatively high Maillard reactivity (meaning that it can lead to undesirable browning).
- the present invention therefore aims to provide an alternative to these known, slow- release carbohydrates which does not suffer from the drawbacks associated with the prior art.
- a glucopyranosyl tetritol in the preparation of a sustained energy release food, feed or drink composition.
- a sustained energy release food, feed or drink composition characterised in that it comprises a glucopyranosyl tetritol.
- a process for the preparation of a sustained energy release food, feed or drink composition characterised in that it comprises the step of adding a glucopyranosyl tetritol to said composition.
- Figure 1 shows the in-vitro digestibility of O- ⁇ -D-Glucopyranosyl erythritol obtained according to Example 3.
- the present invention provides, in a first aspect, the use of a glucopyranosyl tetritol in the preparation of a sustained energy release food, feed or drink composition.
- Glucopyranosyl tetritols are carbohydrate compounds composed of a glucose unit and C4 sugar alcohol unit.
- Sugar alcohols also known as polyols
- They have the general formula C n H 2n+2 O n . - A -
- the glucopyranosyl tetritol of the present invention will preferably be selected from the group consisting of glucopyranosyl erythritol, glucopyranosyl D-threitol, glucopyranosyl L-threitol and mixtures of two or more thereof. Most preferably, the glucopyranosyl tetritol will be glucopyranosyl erythritol, preferably in the form O- ⁇ - D-glucopyranosyl erythritol.
- O- ⁇ - D-glucopyranosyl erythritol can exist as 1-O- ⁇ -D-glucopyranosyl erythritol (when the glucose unit is linked to the primary alcohol group of erythritol) or as 2-0- ⁇ -D- glucopyranosyl erythritol (when the glucose unit is linked to the secondary alcohol group of erythritol).
- the glucopyranosyl tetritols of the present invention will be in their primary form (i.e.
- the glucopyranosyl tetritol of the present invention will be 1-O- ⁇ -D-glucopyranosyl erythritol.
- Glucopyranosyl sugar alcohols such as glucopyranosyl erythritol
- Glucopyranosyl sugar alcohols are known in the art. They were thought, however, to be indigestible or only very slightly digestible. They were therefore characterised as being low calorie compounds (see EP0404964, for instance) with only a small proportion of the glucose units ingested being released into the blood-stream.
- glucopyranosyl tetritols, and glucopyranosyl erythritol undergo a slow but total or near- total hydrolysis in the small intestine resulting, for several hours after ingestion, in a continuous low-level release of glucose into the blood. This effect is referred to herein as "sustained energy release”.
- the present invention further provides a sustained energy release food, feed or drink composition characterised in that it comprises a glucopyranosyl tetritol.
- a sustained energy release food, feed or drink composition characterised in that it comprises a glucopyranosyl tetritol.
- compositions could be used, for example, to deliver carbohydrates to diabetic patients without causing clinically significant hyperglycaemia. They could also be added to the diet of overweight or elderly people suffering from reduced glucose tolerance. In the domain of sports nutrition, glucopyranosyl tetritols could be used to supply athletes with a steady and constant carbohydrate supply during physical exercise. They could also be used in foods or supplements for growing children and in so-called “energy drinks” or “energy bars”. This is, of course, a non-exhaustive list and many other potential embodiments of the present invention will be apparent to the skilled person.
- the present invention provides a process for the preparation of a sustained energy release food, feed or drink composition characterised in that it comprises the step of adding a glucopyranosyl tetritol to said composition.
- the glucopyranosyl tetritol will typically be added in an amount of at least 5% by weight. Preferably, it will be added in an amount of at least 15%, even more preferably in an amount of at least 20% by weight based on the total weight of the composition.
- the exact amount to be added will of course depend on various factors - such as type of application (food, feed or drink), target consumer (sports people, young children, diabetics, etc.), desired level of sweetness and caloric value of the final composition, etc. - and will easily be calculated by the skilled person.
- the glucopyranosyl tetritol may be added to the food, feed or drink composition at any stage during its production.
- glucopyranosyl tetritols have been found to have a good level of sweetness.
- the glucopyranosyl tetritol will be added in lieu of or in combination with other carbohydrate materials or sweeteners.
- glucopyranosyl tetritols can nonetheless be used as a sustained energy release ingredient. Such sustained supply of energy is known to result in hormonal patterns that favour the feeling of fullness (satiation) and induce less hunger.
- glucopyranosyl tetritols have been found to have good sweetness and low cariogenicity when compared to sucrose. Their ingestion leads to only low glycemic and insulinemic responses and therefore presents a significantly reduced risk, if any, of causing either rebound hypoglycaemia or persistent strong hyperglycaemia.
- a low insulinemic response is also known to promote a high rate of fatty acid mobilisation from adipose (fat) tissue resulting in a high rate of fatty acid oxidation in energy metabolism (Newsholme E.A., Leech A.R. (eds): Integration of carbohydrate and lipid metabolism. In: Biochemistry for the medical sciences. John Wiley & Sons, Chichester 1983, pp 336-35, Newsholme E. A., Start C. (eds): Adipose tissue and the regulation of fat metabolism. In: Regulation in Metabolism. John Wiley & Sons, Chichester 1973a, pp 195-246).
- - food, feed and drink compositions aimed at supporting physical and mental performance (e.g. in fitness/sports nutrition, infant nutrition, nutrition for the elderly, in so-called "brain foods” directed, for example, at students or people whose jobs require consistently high levels of concentration and/or alertness such as pilots);
- - food, feed and drink compositions aimed at individuals requiring slow but continuous carbohydrate energy delivery, for example in conditions that require medical nutrition and/or enteral feeding (e.g. for cachexia patients, burn patients), or for post-operative nutrition;
- - food, feed and drink compositions aimed at inducing satiety, reducing overall energy intake and/or increasing fat metabolism (e.g. slimming products, drinks for children, etc.); and - food, feed and drink compositions aimed at individuals suffering from particular metabolic disorders (such as diabetes, low glucose tolerance and metabolic syndrome (syndrome X) patients).
- metabolic disorders such as diabetes, low glucose tolerance and metabolic syndrome (syndrome X) patients.
- a mixture of 58 g water, 40 g erythritol, 100 g maltose and 2 g of transglucosidase (AMANO) was prepared.
- the pH was adjusted to 4.6 with hydrochloric acid.
- the mixture was then heated to 50°C for 24h. After filtration and passing through a strong cation exchanger followed by a weak anion exchanger (elution with demi-water), the syrup was vacuum concentrated to 35% dry substance.
- the total yield of O- ⁇ -D-glucopyranosyl erythritol was 18% as compared to the starting materials (using HPLC analysis).
- Example 2 5ml of the mixture obtained in Example 1 was diluted to 25% Brix and loaded on 1.51 Bio-Gel Polyacrylamide P2-fine (BIORAD) resin and eluted with demineralised water at 1.5ml/min at room temperature. 170mg O- ⁇ -D-glucopyranosyl erythritol was obtained at a purity of 86%.
- the enriched O- ⁇ -D-glucopyranosyl erythritol of Example 2 was used as substrate in in-vitro digestibility studies.
- 1% substrate solutions (w/w) of maltose (from Merck), isomaltulose (from ICN) and O- ⁇ -D-glucopyranosyl erythritol were prepared in a 0.05 M phosphate buffer at pH 6 and equilibrated at 37°C for 10 minutes.
- a suspension of 30% rat intestinal acetone powder (supplied by Sigma) was prepared in 0.05M phosphate buffer (from Merck) at pH 6 and equilibrated at 37°C for 10 minutes.
- 0.6 ml rat intestinal acetone powder suspension was added to 6 ml of each of the substrate solutions and mixed. The mixtures were incubated at 37°C and a 1 ml sample was taken (0 hours incubation time). Further samples were taken after 2, 4 and 6 hours of incubation. The samples were diluted with 4 ml of demineralised water and boiled for 5 minutes. After the denaturation step, each sample was filtered through a 0.45 ⁇ m filter.
- the filtrate was send through a Dionex OnGuard-ATM filter. Glucose content was determined by HPLC.
- O- ⁇ -D-glucopyranosyl erythritol is digested, in-vitro, at a substantially lower rated than maltose.
- the digestion rate is in fact close to that of isomaltulose which is known in the art as being a sustained energy release carbohydrate.
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Hematology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Molecular Biology (AREA)
- Mycology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL06761896T PL1868450T3 (pl) | 2005-04-15 | 2006-04-12 | Kompozycje o przedłużonym uwalnianiu energii |
| US11/911,649 US20080206423A1 (en) | 2005-04-15 | 2006-04-12 | Sustained Energy Release Compositions |
| BRPI0608174-6A BRPI0608174A2 (pt) | 2005-04-15 | 2006-04-12 | uso de um glicopiranosil tetritol, composição de alimento, ração ou bebida de liberação de energia prolongada, e, processo para a preparação da mesma |
| EP06761896A EP1868450B1 (en) | 2005-04-15 | 2006-04-12 | Sustained energy release compositions |
| DE602006007969T DE602006007969D1 (de) | 2005-04-15 | 2006-04-12 | Zusammensetzungen zur verzögerten energiefreisetzung |
| JP2008505802A JP2008545620A (ja) | 2005-04-15 | 2006-04-12 | 持続性エネルギー放出組成物 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05252368.5 | 2005-04-15 | ||
| EP05252368A EP1712139A1 (en) | 2005-04-15 | 2005-04-15 | Sustained energy release compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2006108626A1 true WO2006108626A1 (en) | 2006-10-19 |
Family
ID=34940858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2006/003357 Ceased WO2006108626A1 (en) | 2005-04-15 | 2006-04-12 | Sustained energy release compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20080206423A1 (enExample) |
| EP (2) | EP1712139A1 (enExample) |
| JP (1) | JP2008545620A (enExample) |
| BR (1) | BRPI0608174A2 (enExample) |
| DE (1) | DE602006007969D1 (enExample) |
| ES (1) | ES2326691T3 (enExample) |
| PL (1) | PL1868450T3 (enExample) |
| WO (1) | WO2006108626A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2098124A1 (en) | 2008-03-03 | 2009-09-09 | Nestec S.A. | Carbohydrate gel |
| EP2332426A1 (en) * | 2009-12-11 | 2011-06-15 | Technische Universität Graz | Prebiotic |
| EP2366292A1 (en) * | 2010-03-15 | 2011-09-21 | Nestec S.A. | Artificial sweeteners and performance |
| WO2019201430A1 (en) | 2018-04-17 | 2019-10-24 | Protea Biopharma N.V. | Sustained energy providing and free radical protective composition |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2264394A1 (de) * | 1972-04-12 | 1973-10-31 | Sueddeutsche Zucker Ag | Kalorienarmes suessungsmittel |
| EP0404964A1 (en) * | 1988-12-16 | 1991-01-02 | Showa Denko Kabushiki Kaisha | Production of sugar compounds |
| US20040086615A1 (en) * | 2002-11-04 | 2004-05-06 | Cargill, Inc. & Cerestar Holding Bv | Reduced calorie confectionery compositions |
| JP2004331576A (ja) * | 2003-05-08 | 2004-11-25 | Noevir Co Ltd | 急激な血糖値の上昇を抑制する血糖値上昇抑制剤及び食品 |
| US20050008678A1 (en) * | 1996-05-31 | 2005-01-13 | Howard Alan N. | Food compositions containing creatine |
| US20050095350A1 (en) * | 2003-09-22 | 2005-05-05 | Grain Processing Corporation | Nutritive food source including controlled energy release carbohydrate |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856775A (en) * | 1969-07-14 | 1974-12-24 | Ajinomoto Kk | {62 -(1{43 3)-glucans |
| ATE198259T1 (de) * | 1994-07-01 | 2001-01-15 | Quaker Oats Co | Nahrungsmittel mit zeitverzögerter energiefreisetzung |
| DE19818842C1 (de) * | 1998-04-28 | 2000-01-05 | Suedzucker Ag | Erkältungsmittel |
| US6455096B1 (en) * | 1998-04-28 | 2002-09-24 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Hard candy with a relatively-high moisture and hardness, and process of the same |
| EP1605782A1 (en) * | 2003-03-24 | 2005-12-21 | Cerestar Holding B.V. | Comestibles containing isomaltulose and trehalose for sustained carbohydrate energy release and reduced glycemic/insulinemic responses, and for preserving osmolality |
| JP3732501B2 (ja) * | 2004-03-30 | 2006-01-05 | 辰馬本家酒造株式会社 | α−D−グルコピラノシルグリセロール類及びその製造方法及びその用途 |
-
2005
- 2005-04-15 EP EP05252368A patent/EP1712139A1/en not_active Withdrawn
-
2006
- 2006-04-12 US US11/911,649 patent/US20080206423A1/en not_active Abandoned
- 2006-04-12 BR BRPI0608174-6A patent/BRPI0608174A2/pt not_active IP Right Cessation
- 2006-04-12 WO PCT/EP2006/003357 patent/WO2006108626A1/en not_active Ceased
- 2006-04-12 ES ES06761896T patent/ES2326691T3/es active Active
- 2006-04-12 DE DE602006007969T patent/DE602006007969D1/de active Active
- 2006-04-12 PL PL06761896T patent/PL1868450T3/pl unknown
- 2006-04-12 EP EP06761896A patent/EP1868450B1/en not_active Not-in-force
- 2006-04-12 JP JP2008505802A patent/JP2008545620A/ja active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2264394A1 (de) * | 1972-04-12 | 1973-10-31 | Sueddeutsche Zucker Ag | Kalorienarmes suessungsmittel |
| EP0404964A1 (en) * | 1988-12-16 | 1991-01-02 | Showa Denko Kabushiki Kaisha | Production of sugar compounds |
| US20050008678A1 (en) * | 1996-05-31 | 2005-01-13 | Howard Alan N. | Food compositions containing creatine |
| US20040086615A1 (en) * | 2002-11-04 | 2004-05-06 | Cargill, Inc. & Cerestar Holding Bv | Reduced calorie confectionery compositions |
| JP2004331576A (ja) * | 2003-05-08 | 2004-11-25 | Noevir Co Ltd | 急激な血糖値の上昇を抑制する血糖値上昇抑制剤及び食品 |
| US20050095350A1 (en) * | 2003-09-22 | 2005-05-05 | Grain Processing Corporation | Nutritive food source including controlled energy release carbohydrate |
Non-Patent Citations (1)
| Title |
|---|
| DATABASE WPI Section Ch Week 200501, Derwent World Patents Index; Class B03, AN 2005-002844, XP002337315 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE602006007969D1 (de) | 2009-09-03 |
| JP2008545620A (ja) | 2008-12-18 |
| EP1712139A1 (en) | 2006-10-18 |
| EP1868450B1 (en) | 2009-07-22 |
| ES2326691T3 (es) | 2009-10-16 |
| US20080206423A1 (en) | 2008-08-28 |
| EP1868450A1 (en) | 2007-12-26 |
| BRPI0608174A2 (pt) | 2010-11-09 |
| PL1868450T3 (pl) | 2010-01-29 |
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