EP2046838A2 - Chitins and chitosans in an activated form and their slimming, hypoglycaemic, hypolipidaemic properties - Google Patents
Chitins and chitosans in an activated form and their slimming, hypoglycaemic, hypolipidaemic propertiesInfo
- Publication number
- EP2046838A2 EP2046838A2 EP07805146A EP07805146A EP2046838A2 EP 2046838 A2 EP2046838 A2 EP 2046838A2 EP 07805146 A EP07805146 A EP 07805146A EP 07805146 A EP07805146 A EP 07805146A EP 2046838 A2 EP2046838 A2 EP 2046838A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- polymers
- chitosans
- crosslinked
- activated
- solution
- 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- Withdrawn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
- 229920001661 Chitosan Polymers 0.000 title claims abstract description 87
- 229920002101 Chitin Polymers 0.000 title claims abstract description 32
- 230000000055 hyoplipidemic effect Effects 0.000 title description 2
- 230000002218 hypoglycaemic effect Effects 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 84
- 239000000725 suspension Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 24
- 235000005911 diet Nutrition 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 230000037213 diet Effects 0.000 claims abstract description 16
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 235000016709 nutrition Nutrition 0.000 claims abstract description 11
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims abstract description 9
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 claims abstract description 9
- 239000013589 supplement Substances 0.000 claims abstract description 9
- 201000001421 hyperglycemia Diseases 0.000 claims abstract description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 208000008589 Obesity Diseases 0.000 claims abstract 2
- 230000003213 activating effect Effects 0.000 claims abstract 2
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract 2
- 235000020824 obesity Nutrition 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 25
- 238000004132 cross linking Methods 0.000 claims description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 13
- 230000004913 activation Effects 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- -1 aliphatic aldehyde Chemical class 0.000 claims description 9
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 5
- 239000012062 aqueous buffer Substances 0.000 claims description 5
- 230000006196 deacetylation Effects 0.000 claims description 5
- 238000003381 deacetylation reaction Methods 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000001994 activation Methods 0.000 abstract description 11
- 239000003925 fat Substances 0.000 description 16
- 235000000346 sugar Nutrition 0.000 description 16
- 238000009835 boiling Methods 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 150000008163 sugars Chemical class 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 229930006000 Sucrose Natural products 0.000 description 11
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 11
- 235000013681 dietary sucrose Nutrition 0.000 description 11
- 229960004793 sucrose Drugs 0.000 description 11
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 239000007853 buffer solution Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 235000013305 food Nutrition 0.000 description 7
- 239000004006 olive oil Substances 0.000 description 7
- 235000008390 olive oil Nutrition 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 230000000378 dietary effect Effects 0.000 description 5
- 235000012054 meals Nutrition 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 238000010521 absorption reaction Methods 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
- 229920005615 natural polymer Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- 102000007330 LDL Lipoproteins Human genes 0.000 description 3
- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
- 229920001222 biopolymer Polymers 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 235000013367 dietary fats Nutrition 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 229910000397 disodium phosphate Inorganic materials 0.000 description 3
- 235000019800 disodium phosphate Nutrition 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 235000020845 low-calorie diet Nutrition 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 239000008055 phosphate buffer solution Substances 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000020940 control diet Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 229950006780 n-acetylglucosamine Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IORISFYTXJVNFE-UHFFFAOYSA-N 2,3-dinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O IORISFYTXJVNFE-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920001268 Cholestyramine Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 206010014476 Elevated cholesterol Diseases 0.000 description 1
- 241000593508 Garcinia Species 0.000 description 1
- 235000000885 Garcinia xanthochymus Nutrition 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- ZMJBYMUCKBYSCP-UHFFFAOYSA-N Hydroxycitric acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 235000009200 high fat diet Nutrition 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 235000019313 oat gum Nutrition 0.000 description 1
- 239000001912 oat gum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019980 sodium acid phosphate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
-
- 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
- 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
- A23L29/275—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of animal origin, e.g. chitin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
-
- 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
- This invention relates to D-glucosamine polymers and the corresponding acetylated glucosamine homopolymers, namely N-acetyl-D-glucosamine; it relates in particular to chitosans, optionally in crosslinked form, and chitins, both in activated form. It also relates to the process for producing chitosans and chitins in activated form, and to nutritional preparations that include one or both of said compounds as a basic element, and the use of said nutritional preparations to reduce and control the cholesterol and sugar levels, mainly in the blood.
- LDLs low-density lipoproteins
- Chitin and chitosan biopolymers have an action mechanism which is attributable to their ability to trap (adsorb) fats and sugars from food, thus preventing their enteric absorption.
- the chitins and chitosans in the preparations currently on the market require a daily dose, for the treatment of excess body weight or hyperlipidaemia, of up to six grams a day for a minimum period ranging between 30 and 60 days.
- said polymers would therefore need to be capable of adsorbing a larger amount of fats and sugars.
- chitosans and chitins are poly( ⁇ -1 ,4-glucosamine) and poly( ⁇ -1 ,4-N-acetylglucosamine) respectively.
- the. weight-average molecular weight of said biopolymers is generally between 80,000 and 2,000,000, or even higher.
- chitins and chitosans the latter optionally in crosslinked form, when pretreated with boiling strong bases for a few minutes, considerably increase their ability to sequester dietary fats and sugars per unit of weight of chitin or chitosan polymer.
- said treatment produces "activated" chitins and chitosans which are capable of: a. trapping dietary fats weighing around two/three times as much as the activated polymer, namely approx. four/five times as much as the natural polymer; unlike the natural polymer, the adsorbed fats are not released, even by extraction with organic solvents such as acetone; b.
- a first advantage obtained with the use of activated chitins and chitosans, optionally crosslinked, is therefore the administration of considerably lower doses of said active constituents, while achieving the same effect.
- Another considerable advantage of using activated chitins and chitosans is that the dietary/slimming effect of said polymers is not strictly dependent on a concomitant low-calorie diet. The patient therefore does not necessarily need to follow a low-calorie diet in order to obtain the desired effects to the desired extent.
- This invention therefore relates to D-glucosamine polymers in activated form, said polymers being chosen from among chitins, chitosans and crosslinked chitosans, and the activation being obtained with a process that involves treating the polymers with a strong base and subsequent heating of the polymers.
- Said D-glucosamine polymers used in this invention in both crosslinked and non-crosslinked form, have an apparent density that ranges between approximately 0.3 and 0.80 g/ml, and preferably between 0.5 and 0.7 g/ml.
- the particle size of these polymers typically ranges between 80 and 400 mesh, and preferably between 80 and 200 mesh.
- the chitosans have a degree of deacetylation which typically ranges between 89 and 95%, but those with a degree of deacetylation exceeding 90% are preferred.
- the strong base is preferably a hydroxide of an alkaline or alkaline earth metal, and the hydroxide is more preferably selected from among NaOH and KOH.
- the preferred hydroxide is NaOH.
- Said hydroxide is preferably used in the form of a solution, typically an aqueous solution; the solution of said alkaline or alkaline earth metal hydroxide ranges between approximately 0.5 and 3 N, and more preferably between 1.5 and 2.5 N.
- the polymer is treated with said alkaline solution, and the ratio between polymer and alkaline solution ranges between 1 :2.5 and 1 :5, and preferably between 1 :2.5 and 1 :3.5, the ratio being expressed in weight (g):volume (ml).
- the polymer forms a suspension in said alkaline solution.
- the suspension is heated to approximately the boiling point of the suspension ⁇ 15°, namely between approximately 80 and 110 0 C, and preferably to around the boiling point of the suspension, namely the boiling point of the suspension ⁇ 5°C.
- the suspension is maintained at said temperature for between approximately two and ten minutes, and preferably between four and six minutes.
- the suspension is cooled to ambient temperature.
- the suspension is preferably cooled rapidly; said cooling time is approximately between 30 m and 6 h, and preferably between 30 m and 90 m, for a batch of between 5,000 and 10,000 kg.
- the product of reaction thus obtained is separated from the reaction liquid and rinsed with a washing liquid until the washing liquid has a pH of between 6 and 9, and preferably between 7 and 9.
- the washing liquid is preferably selected from water and an aqueous buffer solution, such as a buffer solution at an acid pH formed by acetic acid and sodium or potassium acid phosphate.
- the product of reaction is dried; drying is conducted, for example, in a stove at a temperature of between approximately 40 and 60 0 C until the dried product reaches a constant weight. [0025] If the activation conditions are extended beyond the soda time and concentration parameters indicated, a decline in adsorbent properties will be observed, probably correlated with an alteration in the polymer structure.
- activated crosslinked chitosans present a considerable increase in their ability to sequester dietary fats and sugars per unit of weight of polymer compared with activated but not crosslinked chitosans.
- the aliphatic aldehyde is preferably a hydrocarbon with a C1-C10 alkyl chain.
- the aldehyde is preferably chosen from among the monoaldehydes and dialdehydes.
- the preferred example of monoaldehyde is formaldehyde.
- the particularly preferred example of dialdehydes is glutaraldehyde ((OHC-(CH2)3-CHO)).
- the crosslinked chitosans according to the invention have a degree of crosslinking which ranges between approximately 1:50 and 1:130, and in particular between 1:60 and 1:120.
- Crosslinking is obtained by reaction of the chitosans with said cross-linking agent.
- the chitosans can be also be crosslinked on either activated or non- activated polymers.
- the chitosan crosslinking process involves reacting the chitosans with a cross-linking agent chosen from among the group of aliphatic aldehydes, preferably with a C1-C10 alkyl chain.
- the aldehyde is preferably chosen from among the monoaldehydes and dialdehydes.
- the preferred example of monoaldehyde is formaldehyde.
- the particularly preferred example of dialdehydes is glutaraldehyde (OHC-(CH2)3-CHO).
- the crosslinking process comprises the following stages: [0034] 1) suspend chitosan in a buffer solution having a pH ranging between 7.5 and 9.5, preferably between 8.0 and 9.0, and more preferably between 8.1 and 8.3 (suspension 1);
- Said buffer solution is obtained by adding acid salts of alkaline metals to the water, preferably a pair of sodium acid phosphates, namely Na2HPO4 and NaH2PO4, or the sodium carbonate/bicarbonate pair.
- Said buffer solution has a salt molarity of between approximately 0.01 and 0.5, and preferably between 0.05 and 0.1.
- the quantity of aliphatic aldehyde reacted with the polymer to be crosslinked is chosen on the basis of the degree of crosslinking to be obtained and the number of functional aldehyde groups in the molecule.
- the ratio between chitosan and cross-linking agent, expressed as moles of glucose contained in the polymer compared with the moles of cross- linking agent, typically ranges between 1 :1 -10-1 and 1 :1 -10-3.
- the cross-linking agent can be added, for example, in the form of an aqueous solution.
- the molarity of the cross-linking agent namely the aldehyde, can range, for example, between 0.1 and 10, and preferably between 0.5 and 2.
- Said organic amine compound is preferably an aminoacid, such as glycine or lysine. Said amine compound is added greatly in excess of the aldehyde functions which have not yet reacted; it is generally a solution which has approximately the same molarity as the solution containing the aldehyde.
- the suspension is preferably stirred at stages (2) and (3).
- lonisation of the hydroxyl functions is believed to give the preactivated polymers the ability to adsorb large amounts of fats and sugars, with a strong, physical bond that is not reversible, even by extraction with organic solvents and/or adequate buffer solutions.
- Said polymers in activated form, optionally crosslinked, are dispensed as diet supplements, preferably in the form of powder, capsules, sachets or tablets.
- the dose of said diet supplements is between approximately 0.5 and 8 g/day, with a posology of approximately 1 to 4 tablets a day.
- a further subject of this invention is therefore a nutritional preparation containing activated chitins and activated, optionally crosslinked, chitosans, obtained by the processes described above.
- Nutritional preparation means any edible, non-pharmaceutical composition; examples of said preparations are meal substitutes, sports foods and functional foods.
- the diet supplements and food preparations according to the invention are to be taken close to meals, preferably immediately after a meal including fatty and sugary foods. They significantly inhibit the absorption of edible fats and sugars eaten in a normal meal, thus performing a considerable slimming effect or correcting hyperlipidaemia and hyperglycaemia.
- the diet supplements and nutritional preparations according to the invention can include any other natural or artificial component known according to the state of the art and commonly used to formulate nutritional preparations, such as additives, excipients, preservatives, sweeteners, essences, colorants and optionally other active substances.
- any other natural or artificial component known according to the state of the art and commonly used to formulate nutritional preparations such as additives, excipients, preservatives, sweeteners, essences, colorants and optionally other active substances.
- - degree of crosslinking expressed as the ratio between the number of amine functions (-NH2) that reacted with an aldehyde function of the cross-linking agent and the total number of amine functions present in the polymer.
- the -NH2 functions still free are titrated by Habeeb's dinitrobenzene sulphonate (DNBS) method (reference A.G.S.A. Anal. Biochim., 1966, 14, 328-336).
- DNBS dinitrobenzene sulphonate
- Vl read the volume occupied by the powder on the graduated cylinder; and [0058] V. calculate the apparent density of the powder under test with the following formula:
- Non-crosslinked chitosans apparent density 0.6 g/ml, particle size 100 mesh and degree of acetylation 95%, and
- Chitosan activation stage Suspend 10 kg of powdered chitosan in 100 I of soda in an apparatus with a capacity of 200 I, fitted with a moving stirrer.
- Example D The chitosan crosslinked at the preceding stage is then activated. Activation is performed by repeating the conditions and procedures described in Example A, but only using a 2 N soda solution and a reaction time from the boiling point of 5 minutes. [0075] Example D
- Chitosan crosslinking stage [0082] Introduce the 20 kg of chitosan activated at the preceding stage into an apparatus fitted with a stirrer, and pour onto it 200 I of an 0.07 M aqueous buffer solution of Na2HPO4/NaH2PO4 at pH 8.2, to which 2 I of a 1 M aqueous solution of formaldehyde is added. [0083] Heat the suspension thus obtained to 37°C for 18 hours, stirring occasionally. Stop the reaction by adding excess glycine (1 I) and filter the suspension through a B ⁇ ckner filter to separate the activated, crosslinked chitosan from the reaction liquid.
- Tables 1 and 2 show the types of polymers used and the data obtained relating to the grams of olive oil adsorbed using the polymers activated under said different conditions described in examples A and B according to the invention.
- D% represents the percentage difference between the fats trapped by the activated chitosan or chitin and the control chitosan or chitin.
- Table 3 shows the types of polymers used and the data obtained using the activated polymers under different conditions according to this invention, said data being compared with those obtained using untreated polymers.
- the item “D%” indicates the percentage of oil removed by extraction.
- Table 4 shows the types of polymers used and the data obtained using polymers activated under different conditions according to the invention.
- D% represents the percentage difference between the saccharose trapped by the activated chitosan or chitin and by the control chitosan or chitin.
- the non-activated chitosan and chitin adsorb 0.9 g and 0.7 g of saccharose respectively.
- the data show that the polymers according to the invention adsorb more saccharose than the non-activated control polymers.
- Example 5 Place 5 g of activated, crosslinked chitosan produced in example D in a pre- calibrated low-pressure chromatography column (diameter and length of column 1 cm and 25 cm respectively); the chitosan constitutes the chromatography bed.
- Table 7 shows the treatment regimen.
- the dose administered was decided on the basis of the amount of excess weight and the blood dysfunction.
- the patients followed a normal diet throughout the treatment period.
- a significant reduction in excess body weight was observed, together with a tendency by the initial functional dysmetabolisms, namely hyperglycaemia and hypercholesterolaemia, to return to normal.
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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IT001373A ITMI20061373A1 (it) | 2006-07-14 | 2006-07-14 | Chitine e chitosani in forma attivata e loro proprieta' dimagranti ipoglicemizzanti e ipolipemizzanti |
PCT/IB2007/052803 WO2008010172A2 (en) | 2006-07-14 | 2007-07-13 | Chitins and chitosans in an activated form and their slimming, hypoglycaemic, hypolipidaemic properties |
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EP2046838A2 true EP2046838A2 (en) | 2009-04-15 |
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EP07805146A Withdrawn EP2046838A2 (en) | 2006-07-14 | 2007-07-13 | Chitins and chitosans in an activated form and their slimming, hypoglycaemic, hypolipidaemic properties |
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AU2011290550B2 (en) * | 2010-08-17 | 2016-04-07 | Mucovax Inc. | Nutritional compositions comprising chitin microparticles |
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US4125708A (en) * | 1977-02-15 | 1978-11-14 | The United States Of America As Represented By The Secretary Of Agriculture | Chitosan modified with anionic agent and glutaraldehyde |
US5993661A (en) * | 1997-04-14 | 1999-11-30 | The Research Foundation Of State University Of New York | Macroporous or microporous filtration membrane, method of preparation and use |
US20030069206A1 (en) * | 1998-07-10 | 2003-04-10 | Nichols Everett J. | Methods and kits for absorbing fat |
US6255085B1 (en) * | 1999-07-08 | 2001-07-03 | Food Industry Research & Development Institute | Production of chitosan and chitin |
ES2169681B1 (es) * | 2000-08-10 | 2003-10-01 | Osfarma S L | Metodo de produccion de filmes de quitosan con una alta capacidad de adherencia celular, producto obrenido y aplicaciones. |
NO20015986D0 (no) * | 2001-08-02 | 2001-12-06 | Einar J Mustaparta | Produktet chitosan, samt fremstillingsmetode og anvendelse av chitosan |
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