EP2701536A1 - Extrait d'algues brunes alimentaires à faible teneur en iode - Google Patents
Extrait d'algues brunes alimentaires à faible teneur en iodeInfo
- Publication number
- EP2701536A1 EP2701536A1 EP12724684.1A EP12724684A EP2701536A1 EP 2701536 A1 EP2701536 A1 EP 2701536A1 EP 12724684 A EP12724684 A EP 12724684A EP 2701536 A1 EP2701536 A1 EP 2701536A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- extract
- algae
- algae extract
- polyphenols
- composition according
- 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.)
- Withdrawn
Links
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Classifications
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- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- 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
- A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
- A23L17/60—Edible seaweed
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- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/734—Alginic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/18—Iodine; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/42—Phosphorus; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/02—Algae
- A61K36/03—Phaeophycota or phaeophyta (brown algae), e.g. Fucus
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation or decoction
Definitions
- the present invention generally relates to an extract of brown algae, especially food and its preparation process, this extract having a very low iodine content, a high content of polyphenols (or polyphenol compounds) and high levels of alginates, polysaccharides and minerals.
- the present invention also relates to an oral absorption composition comprising such an extract.
- the enriched human being seeks, whatever his culture, greater comfort (in the sense of a physically less demanding life) and a more varied and richer diet (especially increased consumption of meat or more sophisticated manufactured products).
- the conjunction of these two phenomena favors the development of a set of risk factors affecting his health.
- the human being decreases his energy consumption, but by feeding in a profusion and in a richer way, he consumes much more than his nutritional needs. This results in the appearance of a syndrome, which is described as metabolic.
- metabolic syndrome in the sense of the present invention a set of metabolic disturbances, which although not falling within the strict definition of the disease, strongly predisposes the development and progression of true chronic diseases such as hypertension , arteriosclerosis, or diabetes.
- a pre-diabetic is six times more likely to develop diabetes than a normal individual.
- medical care does not occur more often than when the disease is declared.
- Hygiene and dietary rules are then in place (more balanced meals and maintenance of physical activity) but are insufficient at this stage of the disease, which makes it necessary to use drugs (eg cholesterol-lowering drugs, antidiabetic drugs. ..).
- Certain food products have been specifically developed to limit the development of these pathologies. These include products based on polyunsaturated fatty acids or fat adsorbers, but which are not always of real interest in the long term. Indeed, the endogenous component of these pathologies is preponderant (it is estimated at 20% the influence of dietary intakes on hypercholesterolemia).
- the present invention therefore relates to the manufacture of food products (extracts and oral absorption compositions comprising these extracts) for the management of individuals with metabolic syndrome, and in particular pre-diabetics.
- oral absorption composition means a product obtained by transformation of a food which is ingested in addition to the diet, around the meals, this product having only one strictly digestive action (no absorption is necessary for the digestive activity of the product and the action is done in the food bowl).
- brown algae food extracts One known solution for the sustainable and effective management of individuals with metabolic syndrome or pre-diabetic individuals is the use of brown algae food extracts. Indeed, the inhibitory power of brown algae extracts, known to be rich in phlorotannins, on certain enzymes present in the digestive system has already been demonstrated in several publications [1] to [3] and few other food plants have such activity. These enzymes degrade complex nutrients into assimilable nutrients (especially sugars) and are therefore one of the important players influencing postprandial blood levels. By inhibiting the activity of these enzymes, the nutrients in the food bolus are more slowly digested and absorbed when taking a meal. The glycemic, insulinemic and triglyceric responses are diminished.
- the brown algae extracts help to reduce the negative impact of excessive food intake compared to the needs, while providing certain elements necessary for the organism such as:
- alginates which form a calcium gel in the stomach, contributing to the enzymatic inhibition activity of polyphenols (congestion of the nutrient attack sites by the enzymes) and causing a satiety effect [5];
- fucans which inhibit the binding of Helicobacter pilori digestive walls limiting the risk of ulcers [6] or that limit enzymatic hydrolysis of starch by inhibitory effects [7].
- the known brown algae extracts are certainly rich in phlorotannins, and thus have an inhibitory activity on certain enzymes of the digestive system.
- they have a high iodine content, even when the extracts are subjected to deiodization. Indeed, during this desiodization, the iodine is only partially eliminated, and the residual content (300 ppm for the less rich) limits the maximum daily usable dose (500mg), and thus the clinical interest of the product.
- the extract marketed by the applicant company itself under the brand InSea 2 ® which is a brown seaweed extract acting as an inhibitor of carbohydrate digestive enzymes, the DC-amylase and cc-glucosidase
- the brown seaweed extract marketed by the company under the brand Bioserae Id-AIG TM the brown seaweed extract marketed by the company under the brand Bioserae Id-AIG TM
- the white kidney bean extract marketed by Ingredia Nutritional branded Phase 2 ® or the brown algae extract manufactured by the company Diana Naturals and subject of the French patent application FR2914190.
- the latter product is intended to combat inflammation, arthritis and allergies, it departs from the scope of the present invention.
- Acarbose DCI (marketed by BAYER under the tradename Glucor® ND) and Orlistat DCI (marketed by the ROCHE and Glaxo SmithKline laboratories under the trade names Xenical® ND and Alli TM ND, respectively).
- the active pharmaceutical ingredient Acarbose DCI has the disadvantage of causing flatulence, and therefore the nonobservance of the treatment
- the pharmaceutical active ingredient Orlistat DCI presents the disadvantage of blocking the absorption of lipids, and thus to cause a very strong acceleration of the transit, and thus finally the nonobservance of the treatment.
- the alginates are necessarily eliminated, whether by acidification (manufacture of the InSea 2 ® product), or by precipitation with calcium chloride, for example (process described in FR2914190), these additional steps entail not only the elimination of alginates (biological interest) but also additional costs;
- iodine removal is by diafiltration (FR2914190): some of the iodine is entrained in the permeate, but also some of the minerals and dry matter; the more one wants to eliminate the iodine, the more it is necessary to diafilter, and the more the extract will be poor in molecules whose molecular mass is lower than the threshold of cutoff (InSea 2 ®: tangential ultrafiltration). In addition, certain contaminants present in the native extract and whose molecular mass is greater than the cut-off point of the membrane will concentrate in the retentate;
- the purpose of the present invention is therefore the development of a brown algae extract with a reduced iodine content, but retaining the initial level of minerals, alginates, fucans and phlorotannins (polyphenols), such as to be as close as possible to the native extract.
- the subject of the present invention is an algae extract, characterized in that it comprises less than 50 ppm of iodine and between 5 and 15%, and preferably between 8 and 10% of polyphenols, said percentage of polyphenols being expressed in chlorogenic acid equivalent relative to the dry weight of the extract.
- polyphenols means the phlorotannins (or phenolic antioxidants) generally present in brown algae: these are chemical structures found very largely in the terrestrial plants and algae.
- the special feature of algae polyphenols is that they are very large molecules whose major monomer is phloroglucinol (hence the name phlorotannins).
- the algae extract according to the invention has an inhibitory activity on -amylase, -glucosidase and lipase.
- the reduced iodine content of the algae extract according to the invention allows a daily intake of up to 3 g of extract according to the invention, thus conforming to the daily iodine intake recommended by the European Union. in Regulation 2006/352 fixing the maximum daily quantity of iodine at 150 mg / day (see also the corresponding French regulation as published in JORF 123 of 9 May 2006).
- the algae extract according to the invention can advantageously be obtained from brown algae, preferably food.
- the algae extract according to the invention may advantageously be obtained from algae (which may in particular be microalgae or macroalgae) belonging to at least one of the species selected from the species Ascophyllum sp. , Fucus sp. , Himanthalia sp. , Undaria sp. , and Laminaria sp ..
- algae of the species Ascophyllum nodosum are preferably used.
- the algae extract according to the invention may contain between 5 and 9% of alginates, percentage expressed as glucuronic acid equivalent relative to the dry weight of the extract.
- alginates in the algae extract according to the invention allows the formation of a calcium gel which contributes to the enzymatic inhibition of phlorotannins and causes an effect of satiety.
- alginates also commonly used in the treatment of gastroesophageal reflux esophageal ⁇ , would, through their power chelator, detoxify the body.
- the algae extract according to the invention may also advantageously contain the majority of minerals (except iodine) contained in said algae before their transformation, and more particularly calcium, magnesium, potassium and phosphorus.
- the presence of these minerals is essential to the proper functioning of the body of the human being (multiple actions).
- the algae extract according to the invention may also advantageously comprise fucans, the properties of which are numerous and affect many areas (prevention of gastric ulcers, relief of stomach disorders, etc.). Fucans in particular exhibit inhibitory effects on the enzymatic hydrolysis of starch.
- the present invention also relates to an oral absorption composition comprising an extract of algae according to the invention.
- the oral absorption composition according to the invention is vehicle-free, the algae extract being incorporated into said composition without any addition.
- the oral absorption composition according to the invention, it comprises an orally acceptable carrier present in said composition in a proportion of 0.5 by weight relative to the total weight of said composition.
- compositions according to the invention may be in any ingestible oral dosage form, and especially in the form of capsules, lozenges, tablets, ampoules, capsules, herbal teas, oral solutions or suspensions, and powders. , flakes or granules.
- the present invention further relates to a process for preparing an algae extract according to the invention, which comprises the following steps:
- said method being characterized in that it comprises between the step of purifying the liquid phase and the step of drying said aqueous extract, a specific deiodification step of said purified aqueous extract which is carried out by passing on a resin exchange resin. ions.
- the process according to the invention makes it possible, without using an organic solvent, to eliminate colloids such as alginates, obtaining a brown algae extract with a decrease in the iodine content (equal to or less than 50 ppm) which is more important than with a method of the prior art, while having a standardized polyphenol content.
- the extract thus obtained is closer to the native extract (no loss of alginates and fucans, no loss of inhibitory activity, little loss of minerals essential substances such as calcium, potassium, magnesium and phosphorus).
- the drying step may advantageously be carried out by atomization, lyophilization, vacuum oven or fluidized bed.
- the drying is carried out by atomization.
- the drying step is preceded by a step of concentration and / or standardization of said aqueous extract by adding soluble dietary fiber (in particular wheat, corn, etc.). to obtain a polyphenol content of between 5 and 15% and preferably between 8 and 10%.
- soluble dietary fiber in particular wheat, corn, etc.
- standardization means a step intended to adjust the polyphenol content in the extract whatever the nature or origin of the algae used to obtain the extract.
- soluble dietary fibers examples include the soluble dietary fibers marketed by Roquette under the trademark Nutriose®.
- the subject of the present invention is also the use of the composition according to the invention for the management of weight, the management of the metabolic syndrome, the glycemic regulation (prediabetes), the limitation of overweight, the lipidemic regulation (cholesterolemia high or subnormal), minor dyspeptic disorders, digestive acidity or mineral supplementation in humans or animals.
- the disease is not yet declared.
- the present invention also relates to an oral absorption composition comprising an algae extract according to the invention for its use as a medicament.
- composition according to the invention can be used as a medicament in the treatment of diabetes, hypercholesterolemia, arterial hypertension, stroke, cardiovascular diseases, obesity, dyspepsia (digestive disorders), gastroesophageal reflux disease (GERD), gastric ulcers and mineral deficiencies in humans or animals.
- diabetes hypercholesterolemia
- arterial hypertension stroke
- cardiovascular diseases obesity
- dyspepsia digestive disorders
- gastroesophageal reflux disease GABA
- gastric ulcers gastric ulcers and mineral deficiencies in humans or animals.
- Example 1 Preparation of a brown algae extract according to the present invention.
- Fresh or dried brown seaweed Ascophyllum nodosum is harvested and then crushed.
- An aqueous maceration is then carried out, the main objective of which is to extract the main constituents of the alga, namely polyphenols, fucans, alginates and minerals.
- the extraction temperature is between 40 ° C and 95 ° C, and the extraction time is at least six hours.
- a solid-liquid separation is carried out on a vibrating screen or centrifugal separator.
- the aqueous extract thus obtained is then clarified so as to eliminate a maximum of microparticles in suspension and thus prevent clogging of the resin in the next step, this operation being carried out on filter press, filter plate or centrifugal decanter.
- An iodine removal step of the extract is then carried out to reach a final content of less than 50 ppm. Removal of iodine from the aqueous extract is by passage over an ion exchange resin at room temperature (between 15 ° C and 25 ° C).
- the extract is then concentrated under vacuum at low temperature to reach between 10 and 15% of dry matter, then it is standardized by adding soluble dietary fiber to obtain a final content of polyphenols between 8 and 10%.
- the extracted liquid thus obtained is then spray-dried to obtain a fine brown powder rich in polyphenols.
- Example 2 Determination of iodine, polyphenols, fucans and alginates of the extract of Example 1
- this assay is performed by sodium thiosulfate titrimetry (ppm) according to the Codex Method of Nutrition and Dietary Foods, ESPA / CN 109/84.
- this assay is carried out according to the FOLIN method and a content expressed in chlorogenic acid is obtained.
- this assay is carried out according to the method of BLUMENKRANTZ and GA-HANSEN to metahydroxydiphenyl and a content expressed as glucuronic acid is obtained.
- dosage is performed according to the DUBOIS method, the principle of which consists in determining the glucose content.
- alginate content 5 to 9%, based on the dry matter
- total sugar content about 30%;
- the extract obtained in Example 1 has the following characteristics:
- starch is incubated with an enzyme (human salivary amylase for example). This incubation leads to the digestion of starch and the production of maltose; a colored product is added and is intended to stop the enzymatic reaction and to reveal the presence of maltose;
- an enzyme human salivary amylase for example
- a colorimetric assay makes it possible to quantify, at a precise wavelength, the residual maltose; the addition of an "inhibitor" to the solution before incubation leads to the reduction of maltose and thus of its colorimetric dosage.
- control solution makes it possible to calculate a percentage of inhibition.
- Table 1 of results shows that at the level of the inhibition of digestive enzymes, the in vitro results obtained for the extracts of algae according to the invention (whatever the batch from which it is derived) are equivalent to those obtained with the algae extract of the prior art InSea 2 ® and the pharmaceutical active Glucor® ND.
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Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1153581A FR2974479B1 (fr) | 2011-04-27 | 2011-04-27 | Extrait d'algues brunes alimentaires a faible teneur en iode |
PCT/FR2012/050887 WO2012146863A1 (fr) | 2011-04-27 | 2012-04-23 | Extrait d'algues brunes alimentaires à faible teneur en iode |
Publications (1)
Publication Number | Publication Date |
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EP2701536A1 true EP2701536A1 (fr) | 2014-03-05 |
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ID=44533245
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP12724684.1A Withdrawn EP2701536A1 (fr) | 2011-04-27 | 2012-04-23 | Extrait d'algues brunes alimentaires à faible teneur en iode |
Country Status (4)
Country | Link |
---|---|
US (1) | US20140199410A1 (fr) |
EP (1) | EP2701536A1 (fr) |
FR (1) | FR2974479B1 (fr) |
WO (1) | WO2012146863A1 (fr) |
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CN106290686B (zh) * | 2016-09-14 | 2018-08-10 | 广州王老吉药业股份有限公司 | Hplc-ms-ms测定王老吉凉茶成分含量的方法 |
WO2019211442A1 (fr) * | 2018-05-04 | 2019-11-07 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Fucoïdanes à partir de diatomées |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5624567A (en) | 1996-02-12 | 1997-04-29 | Umpqua Research Company | Process for removing iodine/iodide from aqueous solutions |
CA2547381A1 (fr) * | 2003-12-10 | 2005-06-23 | Riken Vitamin Co., Ltd. | Extrait d'algue marine et inhibiteur de la glycosidase renfermant cet extrait |
CA2548899A1 (fr) * | 2003-12-10 | 2005-06-23 | Riken Vitamin Co., Ltd. | Extrait d'algues marines et inhibiteur de lipases contenant cet extrait |
WO2006017943A1 (fr) * | 2004-08-17 | 2006-02-23 | Ocean Nutrition Canada Ltd. | Compositions d'ascophyllum et procedes |
EP1977756A1 (fr) | 2007-03-28 | 2008-10-08 | Diana Naturals | Extrait d'algues à base de polyphénols |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2697409B1 (fr) * | 1992-11-03 | 1995-01-20 | Nature Algues | Procédé d'élimination sélective de l'iode dans les algues brunes et extrait d'algues ainsi obtenu. |
JP3425412B2 (ja) * | 2000-07-03 | 2003-07-14 | 株式会社シマヤ | 清涼飲料の製造方法 |
CN100425526C (zh) * | 2005-08-18 | 2008-10-15 | 山东寻山水产集团有限公司 | 一种从海带中提取碘的方法 |
-
2011
- 2011-04-27 FR FR1153581A patent/FR2974479B1/fr not_active Expired - Fee Related
-
2012
- 2012-04-23 US US14/114,319 patent/US20140199410A1/en not_active Abandoned
- 2012-04-23 WO PCT/FR2012/050887 patent/WO2012146863A1/fr active Application Filing
- 2012-04-23 EP EP12724684.1A patent/EP2701536A1/fr not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5624567A (en) | 1996-02-12 | 1997-04-29 | Umpqua Research Company | Process for removing iodine/iodide from aqueous solutions |
CA2547381A1 (fr) * | 2003-12-10 | 2005-06-23 | Riken Vitamin Co., Ltd. | Extrait d'algue marine et inhibiteur de la glycosidase renfermant cet extrait |
CA2548899A1 (fr) * | 2003-12-10 | 2005-06-23 | Riken Vitamin Co., Ltd. | Extrait d'algues marines et inhibiteur de lipases contenant cet extrait |
WO2006017943A1 (fr) * | 2004-08-17 | 2006-02-23 | Ocean Nutrition Canada Ltd. | Compositions d'ascophyllum et procedes |
EP1977756A1 (fr) | 2007-03-28 | 2008-10-08 | Diana Naturals | Extrait d'algues à base de polyphénols |
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Also Published As
Publication number | Publication date |
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FR2974479A1 (fr) | 2012-11-02 |
WO2012146863A1 (fr) | 2012-11-01 |
FR2974479B1 (fr) | 2014-01-10 |
US20140199410A1 (en) | 2014-07-17 |
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