WO2004014159A1 - Procede de reduction de l'indice glycemique des aliments - Google Patents

Procede de reduction de l'indice glycemique des aliments Download PDF

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Publication number
WO2004014159A1
WO2004014159A1 PCT/AU2003/001001 AU0301001W WO2004014159A1 WO 2004014159 A1 WO2004014159 A1 WO 2004014159A1 AU 0301001 W AU0301001 W AU 0301001W WO 2004014159 A1 WO2004014159 A1 WO 2004014159A1
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WIPO (PCT)
Prior art keywords
tricin
flavonoids
meal
food
derivatives
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PCT/AU2003/001001
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English (en)
Inventor
Timothy Ralston Lang
Michael O'shea
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Queen Bioactives Pty Ltd
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Priority to AU2003249773A priority Critical patent/AU2003249773C1/en
Publication of WO2004014159A1 publication Critical patent/WO2004014159A1/fr
Priority to US11/042,831 priority patent/US8129350B2/en
Priority to US13/359,583 priority patent/US8865661B2/en
Priority to US14/447,076 priority patent/US20140342042A1/en
Priority to US14/447,175 priority patent/US9545120B2/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • 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 a method for lowering the Glycaemic Index (Gl) of foods.
  • Glycaemic Index is a measure of how a given food affects postprandial blood sugar levels. It relates principally to foods that are high in carbohydrates, since proteins and fats have relatively little effect on blood sugar. Gl values indicate how quickly the carbohydrates in a given food are broken down in the intestine and converted to blood sugar. Surprisingly, the complex carbohydrates in some foods such as baked potatoes have a higher Gl than refined white sugar. Gl values are calculated in comparison with the assimilation of either glucose or white bread, which are given arbitrary Gls of 100. Note that the Gl of white bread on the glucose scale is 70.
  • Glycaemic Load is an extension of the concept of Gl. GL is calculated by multiplying Gl by the carbohydrate content of a food, expressed in grams, and divided by 100.
  • the Gl, (and hence the GL) of foods may be reduced by slowing the conversion of carbohydrates into blood sugar.
  • One way of doing this is to increase the viscosity of stomach fluids to slow the rate at which carbohydrates are digested.
  • controlling constriction of the pylorus can reduce the rate at which the stomach empties.
  • the viscosity of stomach fluids may be increased by increasing the consumption of dietary fibre, whilst constriction of the pylorus is achieved by the addition of low molecular weight organic acids, such as acetic acid (vinegar) or citric acid (lemon juice), to the diet.
  • Another means to lower Gl is to inhibit the enzymes catalysing the break down of carbohydrate in the intestine.
  • Two enzymes principally responsible for this are -glucosidase and ⁇ -amylase. The activity of these enzymes determines the rate at which glucose is produced from dietary polysaccharides and therefore the rate at which the glucose is absorbed into the blood.
  • Hyperglycemia is treated by lowering the Gl of foods using the drug Acarbose.
  • This drug is a complex oligosaccharide which delays digestion of ingested carbohydrates, by inhibiting intestinal enzymes ( -glucosidases).
  • Acarbose has maximal inhibitory activity against sucrase.
  • Acarbose is also known to inhibit - amylases.
  • Flavonoids are naturally occurring compounds found in plants. According to the present invention, some flavonoids have been found to exhibit inhibitory activity against ⁇ -glucosidases and ⁇ -amylases. Surprisingly, tests have shown that flavonoids and flavonoid analogues and derivatives isolated from the sugar cane plant exhibit inhibitory activity that exceeds that of Acarbose. Typically, flavonoid derivatives obtained from vegetable sources such as sugar cane are flavonoid glycosides. As used herein the term "flavonoid” is taken to include both flavonoids per se and flavonoid analogues and derivatives.
  • Luteolin, apigenin and tricin are all flavonoids that occur naturally in plants such as wheat, alfalfa and sugar cane.
  • the present invention relates to both these compounds and to their analogues and derivatives.
  • the present invention provides a method of delaying digestion by an animal or a human of carbohydrates in food, comprising administering an effective amount of one or more flavonoids to the animal or human in conjunction with the food, wherein the flavonoids are selected from the group consisting of luteolin, apigenin, tricin and their pharmaceutically acceptable analogues and derivatives.
  • the one or more flavonoids are administered together with a nutritional fibre supplement.
  • Preferably at least 7 mg of flavonoid is administered for each 50.0g of carbohydrate in the food.
  • a pharmaceutical formulation suitable for oral administration comprising an effective amount of one or more flavonoids selected from the group consisting of luteolin, apigenin, tricin and their pharmaceutically acceptable analogues and derivatives, and one or more pharmaceutically acceptable excipients.
  • the pharmaceutical formulation may contain other active ingredients, in addition to lubricants, colouring and flavouring agents, anti-caking agents and fillers and excipients known to the art.
  • the pharmaceutical formulation may be in the form of a tablet, dragee, pill or capsule provided with an enteric coating.
  • the pharmaceutical formulation contains a nutritional fibre supplement.
  • a method of producing an oral pharmaceutical formulation for inhibiting intestinal enzymes comprising combining an effective amount of one or more flavonoids selected from the group consisting of luteolin, apigenin, tricin and their pharmaceutically acceptable analogues and derivatives, with one or more pharmaceutically acceptable excipients.
  • the one or more flavonoids may also be combined with other active ingredients.
  • the one or more flavonoids are combined with a nutritional fibre supplement.
  • a food product containing sufficient added amount of one or more flavonoids selected from luteolin, apigenin, tricin and their nutritionally acceptable analogues and derivatives to reduce the glycaemic index of the food product.
  • the amount of added flavonoids contained in the food product is at least 7 mg per 50.0 g of carbohydrate in the food.
  • the food product also contains a nutritional fibre supplement.
  • a method for lowering the glycaemic index of a carbohydrate-containing meal comprising including as part of the meal an effective amount of an extract of sugar cane containing tricin or its nutritionally acceptable analogues and derivatives.
  • the extract contains 5% tricin or tricin diglycoside.
  • the amount of extract ranges from 0.3g to 2.0g per 50.0g carbohydrate in the meal; more preferably the amount of extract is about 1.0g per 50.0 g carbohydrate.
  • the extract is added to the meal during preparation.
  • a nutritional fibre supplement is also added to the meal.
  • a method for lowering the glycaemic index of a carbohydrate-containing meal comprising including as part of the meal an effective amount tricin or its nutritionally acceptable analogues and derivatives.
  • the amount of tricin or its analogues or derivatives is at least 7 mg per 50.0 g of carbohydrate in the meal; more preferably it ranges from 15mg to 100mg per 50. Og carbohydrate in the meal; still more preferably the amount is about 50mg per 50.0 g carbohydrate.
  • the tricin or its analogues or derivatives is added to the meal during preparation.
  • a nutritional fibre supplement is also added to the meal.
  • Example A In Vitro Assays.
  • Alpha-glucosidase Type 1 from bakers yeast, substrate (p-nitrophenyl-alpha-D- glucopyranoside) and a control inhibitor, castanospermine were purchased from Sigma.
  • enzyme dissolved in 50 mM acetate buffer, pH 4.5 was incubated for 30 min, at 37°C in the presence of substrate and in the presence vs. absence of inhibitors (flavonoids or castanospermine at various concentrations). The reaction was carried out in 50 mM acetate buffer, pH 4.5. Final concentration of alpha glucosidase was 0.2 U/ml; final concentration of the substrate was 2 mM.
  • Flavonoids concentrations ranged from 7.8 to 500 ⁇ g/ml and castanospermine was used at final concentration 1 ⁇ g/ml.
  • the reaction was stopped by addition of 0.2 M Na 2 CU3 and absorbance was measured at 405 nm. Background absorbance (without enzyme) was subtracted for every flavonoid concentration used. The inhibitory activity was expressed as 100 minus relative absorbance difference between tested samples and controls.
  • Alpha-amylase from porcine pancreas, alpha-glucosidase, glucoamylase and substrate were purchased from Sigma.
  • alpha-amylase endo-type enzyme
  • auxiliary enzymes exo-type enzymes
  • chromophore p-nitrophenol
  • alpha-amylase 7.5 U/ml was added to a substrate solution containing 1 mM p-nitrophenyl-alpha-maltopentaoside, 15 U/ml of alpha-glucosidase and 25 U/ml of glucoamylase in 50 mM HEPES buffer (pH 7.3) containing 3 mM CaCI 2 and 40 mM NaCI.
  • the reaction was carried out for 15 min at 37°C in the presence vs. absence of flavonoids at concentrations ranged from 11.7 to 750 ⁇ g/ml.
  • flavonoids were the only inhibitors used since they could reduce activity of both alpha-amylase and alpha-glucosidase (the control inhibitor would act only on alpha-amylase). As demonstrated in Figure 2 and in Table 2, all three flavonoids were effective in reducing the activity of alpha- amylase. Luteolin was the most active, inhibiting the enzyme completely even at the lowest concentration tested. The remaining two flavonoids inhibited alpha-amylase dose-dependently, with tricin being more active than apigenin at lower doses.
  • IC 50 values concentration of flavonoids required to inhibit alpha- amylase by 50% were 5.8 ⁇ g/ml, 9.9 ⁇ g/ml and 16.2 ⁇ g/ml for luteolin, tricin and apigenin, respectively (Table 3). At concentration 1.6 mM, all three flavonoids inhibited alpha-amylase completely (Table 3).
  • the assays show dose-dependent inhibition of alpha-glucosidase and alpha- amylase by flavonoids tested in the study.
  • the data additionally show that for all three flavonoids, concentrations lower than 1.6 mM (lower than 454 ⁇ g/ml) were sufficient to produce a substantial inhibition of alpha-glucosidase (70- 100% inhibition achieved for concentrations 125-250 ⁇ g/ml) and that tricin had much greater inhibitory potential than the other two flavonoids tested.
  • the BMI score is a measure of a person's weight in relation to their height. BMI values between 19-25 kg/m 2 are within the healthy weight range.
  • a bioactive extract containing tricin diglycoside was used in the In Vivo study.
  • the extract was obtained by:
  • the permeate was evaporated to approximately 5 litres and allowed to settle for 24 hours at 4 °C. The permeate was then refiltered in preparation for chromatography. 5. Approximately 0.1% acetic acid by volume was added to the permeate before passing the solution over column chromatography (XAD resin). The column was then washed with one bed volume water (plus 0.1% acetic acid) and then eluted in order with 20%, 30% and 40% EtOH/water containing 0.1 % acetic acid. 6. The 40% fraction was evaporated dry at low temperature. The fraction contained 68.95 grams total solids, of which 3.75g (5.4%) was analysed as an unidentified diglycoside of tricin.
  • Test Foods Pure glucose sugar (Glucodin® powder, Boots Health Care Company, North Ryde, NSW, Australia) dissolved in 250 ml of water was used as the reference food, and was consumed by each of the 10 subjects on two separate occasions.
  • the four test meals were consumed by each of the 10 subjects on one occasion only.
  • the four test meals and the reference food were fed to the subjects in portions containing 50 grams of available carbohydrate.
  • the weights and nutrient contents of the test portions of the reference food and the four test meals are listed in Table 4.
  • the bioactive extract was assumed not to provide any macronutrients.
  • the extract contained 5 mg of tricin diglycoside per 100 mg extract.
  • each portion of the reference food was prepared the day before required by fully dissolving 50 grams of pure glucose sugar in 250 ml of hot water in a heatproof plastic glass, which was then covered with airtight plastic wrap and stored overnight in a fridge. The next morning, each portion of the reference food was taken from the fridge shortly before being served to a subject together with 250 ml of plain water. The required portions of the four test meals were prepared shortly before being served to the subjects.
  • the wheat-based cereal was weighed into a large china bowl and served to the subjects together with a glass of 185.1 grams of reduced-fat milk, a glass of 250 ml of water, and a small plastic container of the bioactive extract.
  • the subjects were also given a spoon and were instructed to consume everything that was served to them at a comfortable pace within 12 minutes. The subjects were free to decide how they would consume the bioactive extract. Some subjects added the extract to the cereal and milk, whereas others poured some water into the extract's container and consumed it like a drink.
  • Gl values for foods are relative measures (ie. they indicate how high blood sugar levels rise after eating a particular food compared to the very high blood sugar response produced by the same amount of carbohydrate in the form of glucose sugar).
  • each subject consumed the reference food on two separate occasions and each of the four test meals on one occasion only. Therefore, each subject completed six separate test sessions for this study. For each subject, the reference food was consumed at both the first and last test sessions, and the four test meals were consumed in random order in between.
  • the day before each test session the subjects were required to refrain from consuming alcohol the whole day and to abstain from unusual levels of physical activity or food consumption.
  • the night before each test session the subjects ate a regular evening meal based on a carbohydrate-rich food (other than legumes) and then fasted for 10 hours overnight.
  • a fasting finger-prick blood sample (0.5 ml) was first collected from each subject using a sterile automatic lancet device (Safe-T-Pro®, Boehringer Mannheim GmbH, Mannheim, Germany). After the fasting blood sample was obtained, the subjects were given a fixed portion of the reference food or a test meal, which they consumed together with 250 ml of plain water at a comfortable pace within 12 minutes. A stopwatch was started for each subject as soon as they started eating. The subjects were required to consume everything that was served to them, after which they were required to remain seated at the research centre and refrain from any additional eating or drinking during the next two hours. Additional finger-prick blood samples were taken 15, 30, 45, 60, 90 and 120 minutes after eating had commenced. Therefore, a total of seven blood samples were collected from each subject during each two-hour test session. Measurement of blood glucose responses
  • the concentration of glucose in the plasma component of each of the seven blood samples collected during each two-hour test session was analysed in duplicate using a glucose hexokinase enzymatic assay (Roche Diagnostic Systems, Sydney, Australia) and an automatic centrifugal spectrophotomet c analyser (Roche/Hitachi 912®, Boehringer Mannheim GmbH, Mannheim, Germany).
  • a glucose hexokinase enzymatic assay Roche Diagnostic Systems, Sydney, Australia
  • an automatic centrifugal spectrophotomet c analyser Roche/Hitachi 912®, Boehringer Mannheim GmbH, Mannheim, Germany.
  • AUC area under this two-hour blood plasma glucose response curve
  • a glycaemic index (Gl) value for this test meal was then calculated for that person by dividing the two-hour blood glucose AUC value for the test meal by their average two-hour blood glucose AUC value for the reference food and multiplying by 100 to obtain a percentage score.
  • a Gl value for each test meal was calculated for each of the 10 subjects in the study.
  • the final reported Gl value for each test food is the average of the 10 individual subjects' Gl values. Due to differences in body weight and metabolism, blood glucose responses to the same food vary between different people. The use of the reference food to calculate Gl values reduces the variation between the subjects' blood glucose results to the same food arising from these natural differences. Therefore, the Gl value for the same food varies less between the subjects than their glucose AUC values for this food.
  • the average two-hour blood glucose values for the 50 gram carbohydrate portions of the reference food (glucose sugar) and the four test meals shown as the change in blood glucose from the fasting baseline level are set out in Table 4 (excluding outliers' results).
  • the reference food produced the largest blood sugar glucose response, followed by the control meal (cereal + (Og bioactive extract tricin diglycoside)).
  • cereal + Og bioactive extract tricin diglycoside
  • the Gl value for each test meal varied among the 10 people who participated in the study. This variation in Gl values for the same meal between people is normal and is due to a number of factors, such as the different rates at which the subjects ingested the foods, different physical activity and dietary habits, and genetic differences in carbohydrate metabolism. It is standard scientific practice that if any individual subject's Gl value for a test food is either greater than the group mean (average) value plus two standard deviations (StDev) or less than the group mean value minus two StDev then that value is classified as an outlier value or unusual observation and removed from the datasheet. One outlier value was found among the 10 subjects' Gl values for the test meals with 50 and 100 mg of the bioactive compound. Therefore, the final Gl values for these two test meals is the average of nine subjects' Gl values.
  • the mean ⁇ standard error of the mean (SEM) Gl values for the reference food and the four test meals are listed in Table 6.
  • the wheat-based cereal meal with 15 mg of added bioactive extract was found to have a medium Gl value, and meals with 50 and 100 mg of added bioactive extract were found to have low Gl values.
  • the results of this study suggest that the tricin diglycoside in the extract added to the test meals can effectively reduce the glycaemic response to a high-GI meal.
  • the addition of just 0.3 grams of the bioactive extract (containing approximately 15 mg of tricin diglycoside) reduced the Gl value of the control meal by 15 units (21 %), causing the meal's average Gl value to drop from the high to the medium Gl category.
  • bioactive extract 50 mg of tricin diglycoside
  • the addition of one gram of bioactive extract reduced the Gl value to the control meal by 26 units (37%), making it a low-GI meal, on average.
  • the largest dose of bioactive extract 100 mg tricin diglycoside
  • the largest dose of bioactive extract reduced the Gl value to the control meal by an average of 18 units (25%). Therefore, increasing the dose of bioactive compound from 50 to 100 mg did not result in a further reduction of glycaemia.
  • Table 6 The mean SEM Gl values for the four test meals and the reference food.

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Abstract

L'invention concerne un procédé permettant de retarder, chez l'animal ou chez l'homme, la digestion des glucides des aliments. Ce procédé consiste à administrer à l'animal ou à l'homme une quantité efficace d'au moins un flavonoïde en liaison avec les aliments. Les flavonoïdes sont sélectionnés parmi la lutéoline, l'apigénine, la tricine et leurs analogues et dérivés pharmaceutiquement compatibles.
PCT/AU2003/001001 2002-08-07 2003-08-07 Procede de reduction de l'indice glycemique des aliments WO2004014159A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2003249773A AU2003249773C1 (en) 2002-08-07 2003-08-07 Method of lowering glycaemic index of foods
US11/042,831 US8129350B2 (en) 2002-08-07 2005-01-25 Method of lowering Glycaemic Index of foods
US13/359,583 US8865661B2 (en) 2002-08-07 2012-01-27 Method of lowering glycemic index of foods
US14/447,076 US20140342042A1 (en) 2002-08-07 2014-07-30 Method of lowering glycemic index of foods
US14/447,175 US9545120B2 (en) 2002-08-07 2014-07-30 Method of lowering glycemic index of foods

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Application Number Priority Date Filing Date Title
AU2002950627 2002-08-07
AU2002950627A AU2002950627A0 (en) 2002-08-07 2002-08-07 Method of lowering glycemic index of foods

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EP1781116A1 (fr) * 2004-06-04 2007-05-09 Horizon Science Pty. Ltd. Edulcorant naturel
WO2009049428A1 (fr) * 2007-10-16 2009-04-23 The University Of British Columbia Inhibiteurs d'alpha-amylase : montbrétines et utilisations de ceux-ci
EP2064352A1 (fr) 2006-09-19 2009-06-03 Horizon Science Pty Ltd Extraits dérivés du sucre de canne et procédé de production de ceux-ci
WO2014032100A1 (fr) 2012-08-28 2014-03-06 Phytolin Pty Ltd Procédé d'extraction
US9572852B2 (en) 2011-02-08 2017-02-21 The Product Makers (Australia) Pty Ltd Sugar extracts
WO2018018090A1 (fr) * 2016-07-27 2018-02-01 Nutrition Science Design Pte. Ltd Composition contenant du sucre
US10350259B2 (en) 2013-08-16 2019-07-16 The Product Makers (Australia) Pty Ltd Sugar cane derived extracts and methods of treatment
WO2021167012A1 (fr) * 2020-02-18 2021-08-26 国立大学法人筑波大学 Composition pour la régulation de la fonction neuronale
US11339449B2 (en) 2016-07-27 2022-05-24 Nutrition Science Design Pte. Ltd Process for sugar production

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EP1781116A4 (fr) * 2004-06-04 2009-07-29 Horizon Science Pty Ltd Edulcorant naturel
US8138162B2 (en) 2004-06-04 2012-03-20 Horizon Science Pty Ltd. Natural sweetener
CN102696941A (zh) * 2004-06-04 2012-10-03 视界科技有限公司 天然甜味剂
EP1781116A1 (fr) * 2004-06-04 2007-05-09 Horizon Science Pty. Ltd. Edulcorant naturel
EP2064352A1 (fr) 2006-09-19 2009-06-03 Horizon Science Pty Ltd Extraits dérivés du sucre de canne et procédé de production de ceux-ci
WO2009049428A1 (fr) * 2007-10-16 2009-04-23 The University Of British Columbia Inhibiteurs d'alpha-amylase : montbrétines et utilisations de ceux-ci
US8431541B2 (en) 2007-10-16 2013-04-30 The University Of British Columbia Alpha-amylase inhibitors: the montbretins and uses thereof
US10226502B2 (en) 2011-02-08 2019-03-12 The Product Makers (Australia) Pty Ltd Sugar extract
US9572852B2 (en) 2011-02-08 2017-02-21 The Product Makers (Australia) Pty Ltd Sugar extracts
US9717771B2 (en) 2011-02-08 2017-08-01 The Product Makers (Australia) Pty Ltd Sugar extract
EA031427B1 (ru) * 2012-08-28 2018-12-28 Дзе Продакт Мэйкерз (Острэйлиа) Пти Лтд Способ получения экстракта, извлекаемого из сахарного тростника, и экстракт
EP3569298A1 (fr) 2012-08-28 2019-11-20 The Product Makers (Australia) Pty Ltd Extrait dérivé de sucre de canne
EP2890467A4 (fr) * 2012-08-28 2016-05-25 Product Makers Australia Pty Lot Procédé d'extraction
US20150201660A1 (en) * 2012-08-28 2015-07-23 The Product Makers (Austrilia) Pty Ltd Extraction Method
US11730178B2 (en) 2012-08-28 2023-08-22 Poly Gain Pte Ltd Extraction method
AU2013308395C1 (en) * 2012-08-28 2018-03-15 Poly Gain Pte Ltd Extraction method
JP2015528448A (ja) * 2012-08-28 2015-09-28 ザ プロダクト メーカーズ （オーストラリア） プロプライエタリー リミテッド 抽出方法
WO2014032100A1 (fr) 2012-08-28 2014-03-06 Phytolin Pty Ltd Procédé d'extraction
AU2013308395B2 (en) * 2012-08-28 2016-11-10 Poly Gain Pte Ltd Extraction method
US10350259B2 (en) 2013-08-16 2019-07-16 The Product Makers (Australia) Pty Ltd Sugar cane derived extracts and methods of treatment
JP2019523006A (ja) * 2016-07-27 2019-08-22 ニュートリション サイエンス デザイン ピーティーイー． エルティーディー 糖組成物
US11339449B2 (en) 2016-07-27 2022-05-24 Nutrition Science Design Pte. Ltd Process for sugar production
WO2018018090A1 (fr) * 2016-07-27 2018-02-01 Nutrition Science Design Pte. Ltd Composition contenant du sucre
WO2021167012A1 (fr) * 2020-02-18 2021-08-26 国立大学法人筑波大学 Composition pour la régulation de la fonction neuronale

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