WO2006132586A1 - Use of plant cell membrane for the for the treatment of obesity - Google Patents
Use of plant cell membrane for the for the treatment of obesity Download PDFInfo
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- WO2006132586A1 WO2006132586A1 PCT/SE2006/000676 SE2006000676W WO2006132586A1 WO 2006132586 A1 WO2006132586 A1 WO 2006132586A1 SE 2006000676 W SE2006000676 W SE 2006000676W WO 2006132586 A1 WO2006132586 A1 WO 2006132586A1
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- A—HUMAN NECESSITIES
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- A61K38/00—Medicinal preparations containing peptides
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- A61K36/02—Algae
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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
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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
- A23L33/17—Amino acids, peptides or proteins
- A23L33/18—Peptides; Protein hydrolysates
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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
- A23L33/30—Dietetic or nutritional methods, e.g. for losing weight
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Definitions
- the present invention relates to the use of a composition comprising at least one cell membrane or parts thereof, for the reduction of lipolytic activity and/or to retard fat digestion, suppress appetite, body weight and/or lower blood lipids.
- the invention also relates to the use of said hydrophobic peptide in a pharmaceutical as well as a food composition and methods of treating a mammal with said composition.
- the key enzyme during intestinal fat digestion is pancreatic lipase.
- lipase inhibitor Xenical
- the lipase inhibitor not only reduces body weight but also improves insulin resistance.
- Such findings hence provide strong evidence for a role of intestinal fat digestion on satiety for fat and insulin sensitivity.
- the drawback with this lipase inhibitor is that it inhibits all types of Upases and produces steatorrea due to a strongly impaired fat digestion. It is therefore of utmost importance to develop a natural compound that retards fat digestion in a milder way without causing steatorrea as side effect.
- the present invention relates to the use of a composition, for the reduction of lipolytic activity and/or to retard fat digestion, suppress appetite, body weight and/or lower blood lipids.
- a composition for the reduction of lipolytic activity and/or to retard fat digestion, suppress appetite, body weight and/or lower blood lipids.
- the invention relates to the use of a composition comprising at least one cell membrane or parts thereof, for the reduction of lipolytic activity and/or to retard fat digestion, suppress appetite, body weight and/or lower blood lipids.
- the invention relates to the use of said composition as a pharmaceutical composition.
- the invention relates to the use of said composition as a food composition.
- the invented composition may be used to regulate the appetite, such as for the treatment of the metabolic syndrome either as a disease or a disorder.
- Fig 1 shows the inhibition of pancreatic lipase by biological membranes from leaves. Chloroplast membranes from spinach (filled circles); clover (black squares); Arabidopsis thaliana (triangles); rape (circles) and sugar beet (crosses).
- Fig. 2 shows the inhibition of pancreatic lipase by biological membranes: Mitochondria from potato tuber (squares), mitochondria from chicken heart (filled circles), plasma membrane from spinach leaf (diamonds), membranes from Synechocystis (crosses) and chromatophores of Rhodospirillum rubrum
- Fig. 3 shows the inhibition of pancreatic lipase by isolated membrane proteins.
- Fig 4 shows the effect of treatment with chloroplast membranes, (thylakoids) during high-fat diet for eleven days in Sprague-Dawley rat.
- Food intake with chloroplast membranes squares and without (triangles).
- Data on body weight gain, serum triglycerides and plasma cholecystokinin after onset of thylakoid treatment are shown in Table 1.
- cell membrane is intended to mean a modified or unmodified natural or synthetically made biological cell membrane, of animal, plant, or microbial origin, wherein the cell membrane comprises intact cell membranes or fractions thereof as well as parts thereof or mixtures of parts and intact cell membranes, such as the hydrophobic peptides or hydrophobic proteins of said cell membrane.
- Part of the cell membrane may be between 0.1 to 0.5 ⁇ m and may solely comprise one or more membrane spanning peptides.
- hydrophobic peptide is intended to mean a peptide having at least 85 % hydrophobic amino acid residues selected from the group consisting of alanine, valine, leucine, isoleucine, proline, phenylanaline, tryptophane, methionine, glycine, cysteine together with a few amino acids with charged residues such as arginine and glutamic acid.
- lipolytic activity is intended to mean the rate of hydrolysis of lipids by lipases.
- membrane spanning peptide is intended to mean at least the amino acid residues, which form the membrane spanning part of the protein.
- the peptide may be one or more membrane spanning parts of one membrane spanning proteins, such as a stretch comprising between 15 to 25 amino acid residues and multiples thereof.
- the invention relates to the use of a composition comprising at least one cell membrane or parts thereof, for the reduction of lipolytic activity and/or to retard fat digestion, suppress appetite, body weight and/or lower blood lipids.
- a composition comprising at least one cell membrane or parts thereof, for the reduction of lipolytic activity and/or to retard fat digestion, suppress appetite, body weight and/or lower blood lipids.
- the composition may comprise at least the membrane spanning part of a biological protein, wherein said membrane spanning part comprises hydrophobic amino acid residues. Accordingly the composition comprises a biological membrane or parts thereof, wherein said biological membrane comprises at least said hydrophobic peptide.
- the composition may comprises at least one cell membrane hydrophobic peptide having from about 15 to about 25 amino acid residues, such as 2, 3, 4 or 5 hydrophobic peptides being derived from one and the same protein or different proteins and the composition may comprise Biological cell membranes for example occur in all living cells and constitute a large part of the cell mass.
- Examples of cell membrane fractions according to the invention are cell membrane fractions obtained from animals, plants, algaes, microorganisms or cell membrane fractions of parts thereof, which are synthetic or a mixture thereof.
- the membranes include the plasma membrane, the endoplasmic reticulum, the Golgi membrane, the nuclear membrane, the lysosomal membrane, the mitochondrial membranes and for the green algae and plants also the chloroplast membranes which include the two envelope membranes and the photosynthetic membrane, the thylakoids.
- Biological membranes are composed of proteins and lipids. All biological membranes contain intrinsic membrane proteins with one or several membrane spanning polypeptide chains composed of hydrophobic amino acids.
- lipids such as phospholipids and galactolipids
- phospholipids and galactolipids form bilayers in which the intrinsic membrane/membrane spanning proteins are embedded.
- extrinsic proteins are attached to the surface of the membrane.
- the thylakoids are responsible for photosynthesis in plants, green algae, and in the photosynthetic bacteria such as blue-green and purple bacteria.
- the thylakoid membrane consists of proteins and lipids in about 70/30 per cent ratio. There are more than 100 different proteins in the membrane; the lipid fraction is dominated by galactolipids with the main fatty acids being of the omega-3 type.
- the thylakoid membrane contains several different pigments, chlorophyll a, chlorophyll b, plastoquinones, the carotenoids ⁇ - carotene, luteine, violaxanthin and neoxanthin.
- the thylakoids have a composition of high nutrition value and the same applies to synthetic membranes having the same or substantially the same composition as the thylakoids, i.e., chloroplasts as well as the thylakoids may be used in the food additive as well as in the food product of the invention.
- biological membranes are the chloroplasts or the thylakoid membranes and the membranes may be obtained from clover, rape, sugar beet, dandelion, Arabidopsis thaliana, maize, tobacco, sun flower, salad, Chenopodium, Atriplex, spinach and grasses or a mixture thereof.
- the composition comprises at least one hydrophobic peptide
- said peptide may have a length of 16, 17, 18, 19, 20, 21, 22, 23 or 24 amino acid residues.
- Examples of peptides are shown in SEQ ID NO: 1, SEQ ID NO:2 or SEQ ID NO:3 or mixtures thereof as well as the peptides may be operably linked to each other.
- the amino acid residues may be selected from the group consisting of alanine, valine, leucine, isoleucine, proline, phenylanaline, tryptophane, methionine, glycine, cysteine together with a few amino acids with charged residues such as arginine and glutamic acid.
- the amino acid residues and the peptide may be synthetic or naturally occurring and the same applies for the amino acid residues, i.e., they may be natural or synthetic ones as long as they are hydrophobic or carries a charged residue.
- the membrane fraction may be a cell membrane fraction, which has been treated with one or more enzymes to provide smaller pieces of the cell membranes.
- Said biological membrane or part thereof of the invention may have a size distribution of 0.1 ⁇ m to about 5 ⁇ m, such as 0.1, 0.2, 0.3, 0.4, 0.5 or 1.0 ⁇ m.
- hydrophobic peptide may have from about 1 to about 50 additional amino acid residues and may also be modified by amidation, esterification, acylation, acetylation, PEGylation or alkylation.
- the photosynthetic membranes are the most abundant, with respect to mass, of all biological membranes on earth. Green leaves from plants constitute a convenient and abundant source for isolation and preparation in large quantity of chloroplast membranes for the purpose of this invention. Biological membranes can be isolated in many different ways, such as those mentioned in the examples. The most common being to first disintegrate the cells mechanically which yields membrane vesicles with different size and composition.
- Heating the vesicle suspension such as between 40-100 degree Celsius.
- hydrophobic peptides may be synthesised by standard chemical methods, including synthesis by automated procedure.
- peptide analogues are synthesised based on the standard solid-phase Fmoc protection strategy with HATU (N-[DIMETHYLAMINO- IH- 1.2.3.
- Peptides may alternatively be synthesised by recombinant production (see e.g., U.S. Pat. No. 5,593,866).
- a variety of host systems are suitable for production of the peptide analogues, including bacteria, such as E. coli, yeast, such as Saccharomyces cerevisiae or pichia, insects, such as Sf9, and mammalian cells, such as CHO or COS-7.
- bacteria such as E. coli
- yeast such as Saccharomyces cerevisiae or pichia
- insects such as Sf9
- mammalian cells such as CHO or COS-7.
- Vectors and procedures for cloning and expression in E. coli can be found in for example Sambrook et al.
- the invented composition may be in any form, such as a natural extract obtained by a conventional method such as one of those mentioned below, as well as being dried, freezed or freeze dried.
- the invented composition may be used as a food additive and may be admixed with other components such as fat, butter, margarine, oils, cream, milk, cheese, brie, flour, juices, soft drinks, teas either prior to being added to a food product or during the addition to the food product.
- other components such as fat, butter, margarine, oils, cream, milk, cheese, brie, flour, juices, soft drinks, teas either prior to being added to a food product or during the addition to the food product.
- Said food additive or food composition comprising said composition may be solid, semisolid or in a liquid form. Further it may be freeze dried, spray dried or lyophilised.
- the invented food additive may be used in any kind of food product as well as being used alone. Examples of food products are fat, butter, margarine, oils, cream, milk, cheese, brie, flour, juices, soft drinks, teas. Other examples are yoghurt, ice cream, cakes, bread and dressing.
- the invented composition may also be used as a pharmaceutical composition.
- the pharmaceutical composition comprises the invented composition as well as a pharmaceutically acceptable buffer, excipient, carrier or diluent.
- diseases to be treated are the metabolic syndrome either as a disease or a disorder such as hypertension, arteriosclerosis, gout, diabetes type one and two, cancers and dyslipidemia.
- “Pharmaceutically acceptable” means a non-toxic material that does not decrease the effectiveness of the biological activity of the active ingredients, i.e., the antimicrobial peptide(s).
- Such pharmaceutically acceptable buffers, carriers or excipients are well-known in the art (see Remington's Pharmaceutical Sciences, 18th edition, A.R Gennaro, Ed., Mack Publishing Company (1990) and handbook of Pharmaceutical Excipients, 3rd edition, A. Kibbe, Ed ., Pharmaceutical Press (2000).
- buffer is intended to mean an aqueous solution containing an acid-base mixture with the purpose of stabilising pH.
- buffers are Trizma, Bicine, Tricine, MOPS, MOPSO, MOBS, Tris, Hepes, HEPBS, MES, phosphate, carbonate, acetate, citrate, glycolate, lactate, borate, ACES, ADA, tartrate, AMP, AMPD, AMPSO, BES, CABS, cacodylate, CHES, DIPSO, EPPS, ethanolamine, glycine, HEPPSO, imidazole, imidazolelactic acid, PIPES, SSC, SSPE, POPSO, TAPS, TABS, TAPSO and TES.
- diluent is intended to mean an aqueous or non-aqueous solution with the purpose of diluting the peptide in the pharmaceutical preparation.
- the diluent may be one or more of saline, water, polyethylene glycol, propylene glycol, ethanol or oils (such as safflower oil, corn oil, peanut oil, cottonseed oil or sesame oil).
- the term "adjuvant" is intended to mean any compound added to the formulation to increase the biological effect of the peptide.
- the adjuvant may be one or more of zinc, copper or silver salts with different anions, for example, but not limited to fluoride, chloride, bromide, iodide, tiocyanate, sulfite, hydroxide, phosphate, carbonate, lactate, glycolate, citrate, borate, tartrate, and acetates of different acyl composition.
- the excipient may be one or more of carbohydrates, polymers, lipids and minerals.
- carbohydrates include lactose, sucrose, mannitol, and cyclodextrines, which are added to the composition, e.g., for facilitating lyophilisation.
- polymers are starch, cellulose ethers, cellulose carboxymethylcellulose, hydroxypropylmethyl cellulose, hydroxyethyl cellulose, ethylhydroxyethyl cellulose, alginates, carageenans, hyaluronic acid and derivatives thereof, polyacrylic acid, polysulphonate, polyethylenglycol/polyethylene oxide, polyethyleneoxide/polypropylene oxide copolymers, polyvinylalcohol/polyvinylacetate of different degree of hydrolysis, and polyvinylpyrrolidone, all of different molecular weight, which are added to the composition, e.g., for viscosity control, for achieving bioadhesion, or for protecting the lipid from chemical and proteolytic degradation.
- lipids are fatty acids, phospholipids, mono-, di-, and triglycerides, ceramides, sphingolipids and glycolipids, all of different acyl chain length and saturation, egg lecithin, soy lecithin, hydrogenated egg and soy lecithin, which are added to the composition for reasons similar to those for polymers.
- minerals are talc, magnesium oxide, zinc oxide and titanium oxide, which are added to the composition to obtain benefits such as reduction of liquid accumulation or advantageous pigment properties.
- compositions of the invention may also be in the form of polymer gels, where polymers such as starch, cellulose ethers, cellulose carboxymethylcellulose, hydroxypropylmethyl cellulose, hydroxyethyl cellulose, ethylhydroxyethyl cellulose, alginates, carageenans, hyaluronic acid and derivatives thereof, polyacrylic acid, polysulphonate, polyethylenglycol/polyethylene oxide, polyethyleneoxide/polypropylene oxide copolymers, polyvinylalcohol/polyvinylacetate of different degree of hydrolysis, and polyvinylpyrrolidone are used for thickening of the solution containing the peptide.
- polymers such as starch, cellulose ethers, cellulose carboxymethylcellulose, hydroxypropylmethyl cellulose, hydroxyethyl cellulose, ethylhydroxyethyl cellulose, alginates, carageenans, hyaluronic acid and derivatives thereof, polyacryl
- compositions may be subjected to conventional pharmaceutical operations such as sterilisation and/or may contain conventional adjuvants such as preservatives, stabilisers, wetting agents, emulsifiers, buffers, fillers, etc., e.g., as disclosed elsewhere herein.
- adjuvants such as preservatives, stabilisers, wetting agents, emulsifiers, buffers, fillers, etc., e.g., as disclosed elsewhere herein.
- Suitable preparation forms are, for example granules, powders, tablets, coated tablets, (micro) capsules, syrups, emulsions, microemulsions, defined as optically isotropic thermodynamically stable systems consisting of water, oil and surfactant, liquid crystalline phases, defined as systems characterised by long- range order but short-range disorder (examples include lamellar, hexagonal and cubic phases, either water- or oil continuous), or their dispersed counterparts, gels, ointments, dispersions, suspensions, creams, aerosols, droplets or injectable solution in ampoule form and also preparations with protracted release of active compounds, in whose preparation excipients, diluents, adjuvants or carriers are customarily used as described above.
- compositions will be administered to a patient in a pharmaceutically effective dose.
- pharmaceutically effective dose is meant a dose that is sufficient to produce the desired effects in relation to the condition for which it is administered.
- the exact dose is dependent on the, activity of the compound, manner of administration, nature and severity of the disorder, age and body weight of the patient different doses may be needed.
- the administration of the dose can be carried out both by single administration in the form of an individual dose unit or else several smaller dose units and also by multiple administration of subdivided doses at specific intervals.
- the present invention concerns both humans and other mammal such as horses, dogs, cats, cows, pigs, camels, among others.
- the methods are applicable to both human therapy and veterinary applications.
- the objects, suitable for such a treatment may be identified by well-established hallmarks.
- a description of the isolation of chloroplast membranes, the thylakoids, from spinach and their application in inhibition of the pancreatic lipase activity and reduction of food intake are intended to illustrate, but not to limit, the invention in any manner, shape, or form, either explicitly or implicitly.
- Thylakoids were isolated as described in Danielsson et al. Biochim Biophys Acta 1608, 53-61 (2004) for use in the lipase assay.
- the thylakoids were isolated as follows: Leaves were homogenised in a blender and filtered through four layers of nylon mesh (20 ⁇ m). The filtrate was centrifuged at 5000 g for 10 min to collect the thylakoids. These were washed by resuspension in water and recentrifuged as before. Lipid extraction: 4 ml thylakoid suspension (3.8 mg chlorophyll/mL) mixed with 40 mL chloroform/methanol was incubated for 1 hr on ice.
- the pellet was extracted for a second time and centrifuged as before.
- the pellet was dried in air and extracted with 10 mL of the buffer solution used for thylakoid isolation on ice to remove water soluble proteins.
- the mixture was centrifuged at 400Og for 10 min and the pellet collected. This is named "membrane protein fraction" (Fig 1).
- Trypsin treatment was carried out by incubating the thylakoids with 300 ⁇ g trypsin (Sigma type III) /mg chlorophyll, in 20 mM phosphate buffert (pH 7,4), for 45 min at 37 0 C.
- Rhodospirillum rubrum prepared according to (Wang, H., Franke, C. C, Nordlund, S. & Noren, A. FEMS Microbiol Lett 253: 273-279 (2005)). Before use, extrinsic water soluble proteins were removed by washing with 0.5 M NaCl, 25 mM Tris-HCl, pH 7.8 followed by two washings with the Tris buffer only according to (Wang, H., Franke, C. C, Nordlund, S. & Noren, A. FEMS Microbiol Lett 253: 273-279 (2005)). Before use, extrinsic water soluble proteins were removed by washing with 0.5 M NaCl, 25 mM Tris-HCl, pH 7.8 followed by two washings with the Tris buffer only according to (Wang, H., Franke, C. C, Nordlund, S. & Noren, A. FEMS
- the lipase activity was measured according to the following (Borgstr ⁇ m B. and Erlanson C. European J. of Biochemistry 37: 60-68, 1973): 15 ml of an aqueous solution containing ImM Tris buffer pH 7.0, 1 mM calcium chloride, 150 mM sodium chloride, 4 mM sodiumtaurodeoxycholate, 0,5 ⁇ g lipase, 1 ⁇ g of colipase.
- Gelatine 20 g (dissolved in 200 ml water and heated in water bath to 60-70° C)
- Chloroplast membranes (Thylakoids, containing 1000 mg chlorophyll) suspended in 30 g water Procedure:
- mice Female Sprague-Dawley rats (200 g) from B&K, Sollentuna, Sweden were housed in a temperature-controlled room (22 ⁇ I 0 C) under a 12-h light (6:00 —
- the high-fat diet consisted of a diet, containing by energy 42.1 % fat, 23.9 % protein and 34.0 % carbohydrate with a caloric density of 4.7 kcal/g as described (Lindquist et al. Regul. Pept. 130: 123-132 (2005).
- the high-fat diet containing thylakoids were prepared as for the high-fat diet with the addition of purified thylakoids at a concentration of 2 mg chlorophyll per gram of food. Food intake was measured daily and body weight at the start and end of the feeding period. Cages were carefully monitored for evidence of food spillage.
- the vegetables (300 g) were allowed to thaw at room temperature for 0.5 hours before they were thoroughly processes in a household mixer. Vegetable juice was obtained by feeding the finely cut pieces of vegetable into a household juice centrifuge.
- a smooth well-tasting emulsion was obtained by homogenizing the vegetable juice (60 g) and triglyceride oil (30 g) with a handhelds mixer equipped with stainless steal cutting blades. Emulsions made from broccoli and spinach juice were visually inspected for free oil and/or water phase after 0,5 hours (storage at room temperature) and 10 hours (storage in refrigerator).
Abstract
Description
Claims
Priority Applications (14)
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CN200680020558.XA CN101193649B (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membrane for the for the treatment of obesity |
CA2609208A CA2609208C (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membrane for the treatment of obesity |
ES06747869.3T ES2681894T3 (en) | 2005-06-10 | 2006-06-09 | Use of a plant cell membrane for the treatment of obesity |
KR1020087000639A KR101360801B1 (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membrane for the treatment of obesity |
US11/916,945 US20100047270A1 (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membrane for the treatment of obesity |
AU2006255805A AU2006255805B2 (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membrane for the for the treatment of obesity |
EP06747869.3A EP1893224B1 (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membrane for the treatment of obesity |
PL06747869T PL1893224T3 (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membrane for the treatment of obesity |
JP2008515656A JP5628477B2 (en) | 2005-06-10 | 2006-06-09 | Use of plant cell membranes for the treatment of obesity |
DK06747869.3T DK1893224T3 (en) | 2005-06-10 | 2006-06-09 | APPLICATION OF PLANT CELL MEMBRANE TO TREAT OBESITAS |
EP18170111.1A EP3417868A1 (en) | 2005-06-10 | 2006-06-09 | Composition |
US13/033,871 US8642098B2 (en) | 2005-06-10 | 2011-02-24 | Use of plant cell membrane for the treatment of obesity |
US14/138,471 US9186384B2 (en) | 2005-06-10 | 2013-12-23 | Use of plant cell membrane treatment of obesity |
US14/138,448 US9333226B2 (en) | 2005-06-10 | 2013-12-23 | Use of plant cell membrane treatment of obesity |
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US13/033,871 Division US8642098B2 (en) | 2005-06-10 | 2011-02-24 | Use of plant cell membrane for the treatment of obesity |
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Cited By (8)
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EP1998853A1 (en) * | 2006-03-24 | 2008-12-10 | Unilever N.V. | Healthy food product |
WO2010008333A1 (en) * | 2008-07-14 | 2010-01-21 | Charlotte Erlanson-Albertsson | Large-scale process for the preparation of thylakoids |
WO2011149416A1 (en) | 2010-05-24 | 2011-12-01 | Swedish Oat Fiber Ab | Aqueous dispersion comprising galactolipids and method for production thereof |
WO2012113918A1 (en) * | 2011-02-25 | 2012-08-30 | Thylabisco Ab | Composition comprising thylakoids for delaying the uptake of molecules |
WO2014040962A1 (en) | 2012-09-11 | 2014-03-20 | Thylabisco Ab | Prebiotic thylakoid composition |
WO2015091739A3 (en) * | 2013-12-18 | 2015-10-22 | Thylabisco Ab | Use of thylakoids to reduce the urge for palatable food |
WO2019148250A1 (en) * | 2018-02-02 | 2019-08-08 | Commonwealth Scientific And Industrial Research Organisation | Protecting a bioactive and/or precursor thereof |
US11071767B2 (en) | 2014-04-13 | 2021-07-27 | Marmar Investment Sp. Z O.O. | Dietary compositions for reducing blood glucose levels and for weight management |
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KR101524696B1 (en) * | 2013-09-27 | 2015-06-03 | 한국식품연구원 | Composition for anti-obesity containing extract of spinach |
US20180362921A1 (en) * | 2015-12-14 | 2018-12-20 | Groupe Santé Devonian Inc. | Extraction and process for active thylakoid membranes |
CN108186608B (en) * | 2018-02-28 | 2020-09-01 | 中南大学 | Application of nano thylakoids |
JP2021519273A (en) * | 2018-03-27 | 2021-08-10 | ミノヴィア セラピューティクス リミテッド | Methods for Elevating Lipid and Cholesterol Metabolism |
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WO2020237383A1 (en) * | 2019-05-31 | 2020-12-03 | Groupe Santé Devonian Inc. | Thylakoids as delivery system for cannabinoïds and other molecules and formulations thereof |
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1998853A1 (en) * | 2006-03-24 | 2008-12-10 | Unilever N.V. | Healthy food product |
WO2010008333A1 (en) * | 2008-07-14 | 2010-01-21 | Charlotte Erlanson-Albertsson | Large-scale process for the preparation of thylakoids |
WO2011149416A1 (en) | 2010-05-24 | 2011-12-01 | Swedish Oat Fiber Ab | Aqueous dispersion comprising galactolipids and method for production thereof |
US9237762B2 (en) | 2010-05-24 | 2016-01-19 | Swedish Oat Fiber Ab | Aqueous dispersion comprising galactolipids and method for production thereof |
WO2012113918A1 (en) * | 2011-02-25 | 2012-08-30 | Thylabisco Ab | Composition comprising thylakoids for delaying the uptake of molecules |
WO2014040962A1 (en) | 2012-09-11 | 2014-03-20 | Thylabisco Ab | Prebiotic thylakoid composition |
WO2015091739A3 (en) * | 2013-12-18 | 2015-10-22 | Thylabisco Ab | Use of thylakoids to reduce the urge for palatable food |
US11071767B2 (en) | 2014-04-13 | 2021-07-27 | Marmar Investment Sp. Z O.O. | Dietary compositions for reducing blood glucose levels and for weight management |
WO2019148250A1 (en) * | 2018-02-02 | 2019-08-08 | Commonwealth Scientific And Industrial Research Organisation | Protecting a bioactive and/or precursor thereof |
Also Published As
Publication number | Publication date |
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KR101360801B1 (en) | 2014-02-11 |
ES2681894T3 (en) | 2018-09-17 |
DK1893224T3 (en) | 2018-08-06 |
EP1893224A4 (en) | 2012-05-30 |
HUE040501T2 (en) | 2019-03-28 |
US20100047270A1 (en) | 2010-02-25 |
US9333226B2 (en) | 2016-05-10 |
US20140220084A1 (en) | 2014-08-07 |
EP3417868A1 (en) | 2018-12-26 |
CN101193649B (en) | 2014-06-11 |
US9186384B2 (en) | 2015-11-17 |
JP5628477B2 (en) | 2014-11-19 |
JP2008545779A (en) | 2008-12-18 |
KR20080021127A (en) | 2008-03-06 |
US8642098B2 (en) | 2014-02-04 |
JP2014237646A (en) | 2014-12-18 |
CN101193649A (en) | 2008-06-04 |
JP5924787B2 (en) | 2016-05-25 |
PL1893224T3 (en) | 2018-10-31 |
US20140220070A1 (en) | 2014-08-07 |
EP1893224A1 (en) | 2008-03-05 |
AU2006255805A1 (en) | 2006-12-14 |
AU2006255805B2 (en) | 2013-02-14 |
CA2609208A1 (en) | 2006-12-14 |
CA2609208C (en) | 2016-10-18 |
EP1893224B1 (en) | 2018-05-02 |
US20110206723A1 (en) | 2011-08-25 |
PT1893224T (en) | 2018-07-30 |
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