EP1986509A2 - Arabinogalactan-protein mit der eigenschaft, fette zu absorbieren, und verfahren zur gewinnung dieses arabinogalactan-proteins - Google Patents
Arabinogalactan-protein mit der eigenschaft, fette zu absorbieren, und verfahren zur gewinnung dieses arabinogalactan-proteinsInfo
- Publication number
- EP1986509A2 EP1986509A2 EP06849571A EP06849571A EP1986509A2 EP 1986509 A2 EP1986509 A2 EP 1986509A2 EP 06849571 A EP06849571 A EP 06849571A EP 06849571 A EP06849571 A EP 06849571A EP 1986509 A2 EP1986509 A2 EP 1986509A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- arabinogalactan protein
- protein
- water
- agp
- cactus
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims abstract description 28
- 108010054251 arabinogalactan proteins Proteins 0.000 title claims description 13
- 239000003925 fat Substances 0.000 title claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 241000219357 Cactaceae Species 0.000 claims abstract description 19
- 229920000715 Mucilage Polymers 0.000 claims abstract description 11
- 239000000853 adhesive Substances 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 11
- 235000013367 dietary fats Nutrition 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002803 maceration Methods 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 4
- 238000000889 atomisation Methods 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 229930182830 galactose Natural products 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000000502 dialysis Methods 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 235000012054 meals Nutrition 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 5
- 239000007787 solid Substances 0.000 abstract description 4
- 239000000843 powder Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 150000004676 glycans Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- BLKPFVWYBFDTPX-UHFFFAOYSA-N 2-(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)acetaldehyde Chemical compound C1C2C(C)(C)C1CC=C2CC=O BLKPFVWYBFDTPX-UHFFFAOYSA-N 0.000 description 4
- 229920000189 Arabinogalactan Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920001661 Chitosan Polymers 0.000 description 4
- 240000008607 Opuntia megacantha Species 0.000 description 4
- 235000002840 Opuntia megacantha Nutrition 0.000 description 4
- 235000006538 Opuntia tuna Nutrition 0.000 description 4
- 235000019312 arabinogalactan Nutrition 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- 239000001904 Arabinogalactan Substances 0.000 description 2
- 241000272194 Ciconiiformes Species 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 240000009297 Opuntia ficus-indica Species 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- 235000019577 caloric intake Nutrition 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004260 weight control Methods 0.000 description 2
- 101150116940 AGPS gene Proteins 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 101000587430 Homo sapiens Serine/arginine-rich splicing factor 2 Proteins 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 235000004727 Opuntia ficus indica Nutrition 0.000 description 1
- 102100029666 Serine/arginine-rich splicing factor 2 Human genes 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000002879 macerating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical group C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229940002552 xenical Drugs 0.000 description 1
Classifications
-
- 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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/33—Cactaceae (Cactus family), e.g. pricklypear or Cereus
-
- 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
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/25—Exudates, e.g. gum arabic, gum acacia, gum karaya or tragacanth
-
- 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
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
-
- 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
- A61P3/06—Antihyperlipidemics
Definitions
- AGP Arabinogalactan (s) protein (s)
- AG Arabinogalactan (s)
- the present invention is related to methods of weight control and cholesterol reduction without the need for restriction of dietary energy intake.
- the former even with added fiber, has a limited capacity for fixation under physiological conditions.
- the change in pH in the intestines there is a phenomenon of lipid re-release, which frees them from chitosan fixation. The result is that the lipids can be assimilated by the body.
- the nopal powder As for the nopal powder, it is a heterogeneous material, of natural origin, therefore of variable composition over time, but having proved a capacity of attachment of fat equivalent or even superior to that of chitosan.
- the problem is to find an active ingredient that is:
- AGPs are very common in the plant world. This combination of polysaccharides and proteins seems to have important physiological functions for plants.
- the saccharine part (AG) is also of great commercial importance, hence a scientific interest marked by the number of publications and patents that concern them.
- the structure of AGs has been extensively studied. See, for example, E.G., Timell, Adv. Carbohydrate Chem., Vol. 20, pp. 409-483 (1965).
- Arabinogalactans are polysaccharides whose backbones consist of beta (1,3) -galactan chains, densely branched by side chains consisting of arabinose, galactose and often other minor residues.
- AGs are gum arabic, exuding Acacia Senegal.
- a more recent source of relatively pure GAs is the extract of Larex Occidentalis wood.
- These AGs are used in the food and cosmetics industry as a texturizing agent, gelling agent and as an emulsifier facilitating the water - oil mixture.
- the said AGP may be in any galenical or commercial form, solid or dissolved in water.
- the invention aims to propose a method based on a product, and a process for obtaining such a product, having the property of fixing fats. It aims to provide a product that can be safely ingested (that is to say not harmful) and has the property of fixing fats in vivo to remove them from digestion.
- the invention aims at first, a method for absorbing, fixing and then eliminating dietary fat ingested before assimilation by the body using an AGP extracted from the cactus mucilage.
- AGP extracted from cacti mucilage behaves similarly, given the structure of the polysaccharide that constitutes it.
- the AGP extracted from the cactus, object of this invention can be in any galenic or commercial form, solid or dissolved in water. It can be packaged alone, in the form of tablets, capsules, soft or rigid capsules or just powder to dissolve in a drink (water or other soda, fruit juice, etc.) or to sprinkle on a food. It is then preferably ingested during a meal.
- the invention is therefore extended to any preparation, containing AGP extracted from cactus mucilage, having the property of fixing ingested dietary fats, so as to minimize their assimilation. It is also the mode of extraction of this AGP from the mucilage of a cactus genus platyopuntia, by a process to preserve the association polysaccharide-protein association responsible for the activity observed.
- the maceration must take place quickly enough, and at low temperature.
- the maceration is immediately followed by a solid liquid separation.
- the separation is advantageously carried out by centrifugation and filtration.
- the resulting AGP solution is then purified.
- This purification is advantageously obtained according to the invention, by subjecting it to dialysis against distilled water, to eliminate salts, and molecules of small molecular weight.
- the purified AGP solution is then concentrated.
- the concentration is advantageously obtained according to the invention, in an enclosure under partial vacuum and at low temperature.
- the concentrated solution of AGP is then dried.
- the elimination of water can be done in two advantageous ways according to the invention. Either by lyophilization or by atomization.
- the AGP produced according to the invention is compared with commercial products having the property of fixing fats.
- test tubes each containing 7.5 ml of 0.1N HCl and 6 g (mass M) of sunflower oil are prepared.
- 100 mg (mass M1) of the test preparation (Neopuntia ® type cactus powder, Absorbitol ® type chitosan, commercial Larex UF ® type ag or Acacia gum type AGP or prepared according to the invention are placed in each tube. ).
- the solutions obtained are mixed vigorously, shaking the tube by hand for 30s, and placed in an oven at 37 ° C for an incubation of 2 hours.
- 0.5 ml of a pH 7.3 buffer solution are then added to each of the tubes.
- the tubes are returned to the oven at 37 ° C. for 3 hours. They are then centrifuged for 5 minutes at 2000 rpm.
- the supernatant fat is then removed and weighed (mass M2), and the ratio of the mass of fatty substance fixed by the preparation (M-M2) to the preparation mass used (Ml), called the attachment ratio, is calculated.
- the extraction method disclosed by this invention aims to prepare a high molecular weight arabinogalactan protein without causing breakdown of the bonds between the polysaccharide moiety and the protein moiety.
- the resulting brilliant juice is then dialyzed against purified water, on 10,000 Dalton cutoff membrane, and then concentrated in the falling film evaporator ADF for 90 minutes. 1 liter of concentrate is taken to make it freeze-dried. The remainder is passed on the atomization tower working at a hot air temperature of 190 ° C. In both cases (lyophilization or atomization), the AGP powder obtained is light yellow in color.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medical Informatics (AREA)
- Dispersion Chemistry (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MA28668A MA28714B1 (fr) | 2005-12-15 | 2005-12-15 | Une arabinogalactane proteine ayant la propriete d'absorber les graisses et le procede d'obtention de cette arabinogalactane proteine |
| PCT/MA2006/000005 WO2007100236A2 (fr) | 2005-12-15 | 2006-12-13 | Une arabinogalactane proteine ayant la propriete d’absorber les graisses et le procede d’obtention de cette arabinogalactane proteine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1986509A2 true EP1986509A2 (de) | 2008-11-05 |
Family
ID=38459451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP06849571A Withdrawn EP1986509A2 (de) | 2005-12-15 | 2006-12-13 | Arabinogalactan-protein mit der eigenschaft, fette zu absorbieren, und verfahren zur gewinnung dieses arabinogalactan-proteins |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090253621A1 (de) |
| EP (1) | EP1986509A2 (de) |
| JP (1) | JP2009519327A (de) |
| CA (1) | CA2632713A1 (de) |
| MA (1) | MA28714B1 (de) |
| WO (1) | WO2007100236A2 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1051560C (zh) * | 1990-03-07 | 2000-04-19 | 普利瓦药物、化学、食品、化妆品工业公司 | 抗菌素与络合金属盐的螯合物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4223023A (en) * | 1978-10-12 | 1980-09-16 | Ivan Furda | Nonabsorbable lipid binder |
| FR2823423B1 (fr) * | 2001-04-11 | 2004-08-27 | Bio Serae Laboratoires | Preparation a base de cactaceae ayant la propriete de fixer les graisses, et procede d'obtention d'une telle preparation |
| CA2519969C (en) * | 2003-04-07 | 2013-03-19 | Phillips Hydrocolloids Research Limited | Modified gum arabic |
| EP1612225A4 (de) * | 2003-04-09 | 2008-01-02 | Phillips Hydrocolloids Res Ltd | Modifiziertes akaziengummi und verwendung davon |
-
2005
- 2005-12-15 MA MA28668A patent/MA28714B1/fr unknown
-
2006
- 2006-12-13 EP EP06849571A patent/EP1986509A2/de not_active Withdrawn
- 2006-12-13 US US12/097,363 patent/US20090253621A1/en not_active Abandoned
- 2006-12-13 CA CA002632713A patent/CA2632713A1/fr not_active Abandoned
- 2006-12-13 JP JP2008545512A patent/JP2009519327A/ja active Pending
- 2006-12-13 WO PCT/MA2006/000005 patent/WO2007100236A2/fr not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2007100236A2 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1051560C (zh) * | 1990-03-07 | 2000-04-19 | 普利瓦药物、化学、食品、化妆品工业公司 | 抗菌素与络合金属盐的螯合物的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| MA28714B1 (fr) | 2007-07-02 |
| JP2009519327A (ja) | 2009-05-14 |
| WO2007100236A3 (fr) | 2007-12-21 |
| US20090253621A1 (en) | 2009-10-08 |
| WO2007100236A2 (fr) | 2007-09-07 |
| CA2632713A1 (fr) | 2007-09-07 |
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