JPH06228181A - New oligosaccharide comprising glucuronic acid, its production and utilization - Google Patents
New oligosaccharide comprising glucuronic acid, its production and utilizationInfo
- Publication number
- JPH06228181A JPH06228181A JP5202587A JP20258793A JPH06228181A JP H06228181 A JPH06228181 A JP H06228181A JP 5202587 A JP5202587 A JP 5202587A JP 20258793 A JP20258793 A JP 20258793A JP H06228181 A JPH06228181 A JP H06228181A
- Authority
- JP
- Japan
- Prior art keywords
- glucuronic acid
- glcua
- gal
- oligosaccharide
- containing oligosaccharide
- 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.)
- Granted
Links
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 229940097043 glucuronic acid Drugs 0.000 title claims abstract description 66
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 56
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 56
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 31
- 239000011707 mineral Substances 0.000 claims abstract description 31
- 229930182830 galactose Natural products 0.000 claims abstract description 16
- 235000013305 food Nutrition 0.000 claims abstract description 12
- 102000005936 beta-Galactosidase Human genes 0.000 claims abstract description 9
- 108010005774 beta-Galactosidase Proteins 0.000 claims abstract description 9
- 102000006995 beta-Glucosidase Human genes 0.000 claims abstract description 9
- 108010047754 beta-Glucosidase Proteins 0.000 claims abstract description 9
- 238000006276 transfer reaction Methods 0.000 claims abstract description 5
- 238000010521 absorption reaction Methods 0.000 claims description 15
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 12
- 239000008101 lactose Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 3
- 235000013361 beverage Nutrition 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- 239000003623 enhancer Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 abstract description 54
- 241001465754 Metazoa Species 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 208000020084 Bone disease Diseases 0.000 abstract description 2
- 208000001132 Osteoporosis Diseases 0.000 abstract description 2
- 230000002708 enhancing effect Effects 0.000 abstract description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 235000000346 sugar Nutrition 0.000 description 14
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 12
- 239000011575 calcium Substances 0.000 description 12
- 229910052791 calcium Inorganic materials 0.000 description 12
- 239000000843 powder Substances 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 230000001737 promoting effect Effects 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- -1 chromatography Chemical class 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000006911 enzymatic reaction Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- FNEHAOQZWPHONV-UHFFFAOYSA-N 9h-carbazole;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C3=CC=CC=C3NC2=C1 FNEHAOQZWPHONV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 229940124532 absorption promoter Drugs 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000015203 fruit juice Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000020183 skimmed milk Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000193752 Bacillus circulans Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- UYUXSRADSPPKRZ-UHFFFAOYSA-N D-glucuronic acid gamma-lactone Natural products O=CC(O)C1OC(=O)C(O)C1O UYUXSRADSPPKRZ-UHFFFAOYSA-N 0.000 description 2
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical compound O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 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 2
- 239000005862 Whey Substances 0.000 description 2
- 102000007544 Whey Proteins Human genes 0.000 description 2
- 108010046377 Whey Proteins Proteins 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 229950002441 glucurolactone Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- 235000008939 whole milk Nutrition 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- RBCOYOYDYNXAFA-UHFFFAOYSA-L (5-hydroxy-4,6-dimethylpyridin-3-yl)methyl phosphate Chemical compound CC1=NC=C(COP([O-])([O-])=O)C(C)=C1O RBCOYOYDYNXAFA-UHFFFAOYSA-L 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000186000 Bifidobacterium Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 102000002464 Galactosidases Human genes 0.000 description 1
- 108010093031 Galactosidases Proteins 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-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
- 240000002129 Malva sylvestris Species 0.000 description 1
- 235000006770 Malva sylvestris Nutrition 0.000 description 1
- 101100513612 Microdochium nivale MnCO gene Proteins 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- WNFHGZLVUQBPMA-JSCKKFHOSA-M Sodium glucuronate Chemical compound [Na+].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O WNFHGZLVUQBPMA-JSCKKFHOSA-M 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 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 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- FDJOLVPMNUYSCM-UVKKECPRSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7, Chemical compound [Co+3].N#[C-].C1([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)[N-]\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O FDJOLVPMNUYSCM-UVKKECPRSA-L 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-OUBTZVSYSA-N deuterium atom Chemical compound [2H][H] UFHFLCQGNIYNRP-OUBTZVSYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229940036630 folic acid 0.2 mg Drugs 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規なグルクロン酸含
有オリゴ糖及びその製造法に関する。また、本発明は、
このような新規なグルクロン酸含有オリゴ糖を利用し
て、これを有効成分とするミネラル吸収促進剤あるいは
このようなオリゴ糖を配合してミネラルの吸収性を高め
た飲食品及び飼料に関する。TECHNICAL FIELD The present invention relates to a novel glucuronic acid-containing oligosaccharide and a method for producing the same. Further, the present invention is
The present invention relates to a mineral absorption promoter containing such a novel glucuronic acid-containing oligosaccharide as an active ingredient, or a food or drink and a feed in which such an oligosaccharide is mixed to enhance the absorbability of minerals.
【０００２】[0002]
【従来の技術】従来より、日本人のカルシウム摂取量
は、栄養必要量を下回っている現状にあり、カルシウム
の摂取が求められている。しかしながら、日本人の平均
的な食習慣では、十分な量のカルシウムを含む献立を継
続するのに相当の努力を要する。また、カルシウム以外
に亜鉛、鉄、銅、マグネシウムなどのミネラルについて
も不足しがちであり、ミネラルの吸収性が高い食品と共
に、ミネラルの吸収を促進する物質に対しても関心が高
まっている。一方、近年、酵素による糖転移反応を利用
して種々のオリゴ糖類が合成されており、腸内の有用菌
であるビフィズス菌の増殖促進物質など食品の機能性を
高める素材として利用されるようになっている。2. Description of the Related Art Conventionally, the intake of calcium has been demanded in Japan, and the intake of calcium has been required. However, the average dietary habits of the Japanese people require considerable effort to continue the menu with a sufficient amount of calcium. In addition to calcium, minerals such as zinc, iron, copper, and magnesium tend to be deficient, and there is growing interest in substances that promote absorption of minerals as well as foods that have high mineral absorption. On the other hand, in recent years, various oligosaccharides have been synthesized by utilizing a glycosyl transfer reaction by an enzyme, and are used as a material for enhancing the functionality of foods such as a growth promoting substance for Bifidobacterium which is a useful bacterium in the intestine. Has become.
【０００３】[0003]
【発明が解決しようとする課題】本発明者等は、上述の
問題点に鑑み、ミネラルの吸収性を向上させる物質につ
いて鋭意検討を進めたところ、β−ガラクトシダーゼあ
るいはβ−グルコシダーゼによるガラクトース転移反応
によって乳糖とグルクロン酸とから合成した新規なグル
クロン酸含有オリゴ糖がミネラルの吸収性を向上させる
ことを見出し、本発明を完成するに至った。したがっ
て、本発明は、新規なグルクロン酸含有オリゴ糖を提供
することを課題とする。また、本発明は、新規なグルク
ロン酸含有オリゴ糖を製造する方法を提供することを課
題とする。さらに、本発明は、新規なグルクロン酸含有
オリゴ糖を有効成分とするミネラル吸収促進剤及び新規
なグルクロン酸含有オリゴ糖を配合してミネラルの吸収
性を高めた飲食品及び飼料を提供することを課題とす
る。In view of the above-mentioned problems, the inventors of the present invention have made earnest studies on substances that improve the absorbability of minerals, and found that β-galactosidase or β-glucosidase causes a galactose transfer reaction. The present inventors have found that a novel glucuronic acid-containing oligosaccharide synthesized from lactose and glucuronic acid improves the absorbability of minerals, and completed the present invention. Therefore, an object of the present invention is to provide a novel glucuronic acid-containing oligosaccharide. Another object of the present invention is to provide a method for producing a novel glucuronic acid-containing oligosaccharide. Furthermore, the present invention provides a mineral absorption promoter containing a novel glucuronic acid-containing oligosaccharide as an active ingredient and a novel glucuronic acid-containing oligosaccharide to provide a food or drink and a feed with enhanced mineral absorption. It is an issue.
【０００４】[0004]
【課題を解決するための手段】本発明の化合物は、ガラ
クトースとグルクロン酸が結合した次の一般式で示され
る新規なグルクロン酸含有オリゴ糖であって、ミネラル
の吸収性を向上させる性質を有する。この新規なグルク
ロン酸含有オリゴ糖は、乳糖とグルクロン酸とに、β−
ガラクトシダーゼあるいはβ−グルコシダーゼを作用さ
せてガラクトース転移反応を行わせ、これを単離するこ
とによって得ることができる。 （Ｇａｌ）ｎ−ＧｌｃＵＡ （ただし、式中、Ｇａｌはガラクトースを、ＧｌｃＵＡ
はグルクロン酸をそれぞれ示し、ｎは１〜３の整数であ
る。）The compound of the present invention is a novel glucuronic acid-containing oligosaccharide represented by the following general formula in which galactose and glucuronic acid are bound to each other, and has a property of improving the absorbability of minerals. . This novel glucuronic acid-containing oligosaccharide contains β-
It can be obtained by allowing galactosidase or β-glucosidase to act to cause a galactose transfer reaction and isolating this. (Gal) n-GlcUA (In the formula, Gal represents galactose and GlcUA
Represent glucuronic acid, and n is an integer of 1 to 3. )
【０００５】本発明で用いる乳糖は、一般に市販されて
いる乳糖でもよく、また、乳糖を成分中に含有する全
乳、脱脂乳、ホエーなどでもよい。なお、乳糖を成分中
に含有する全乳、脱脂乳、ホエーなどを用いる場合は、
必要に応じて濃縮し、乳糖の含量を高めて用いるとよ
い。一方、本発明で用いるグルクロン酸は、代表的なウ
ロン酸であり、動物のムコ多糖や植物のアラビアゴム、
ヘミセルロース、サポニンなどの構成糖として知られて
いるものである。グルクロン酸は、市販されているグル
クロン酸やその塩でよい。The lactose used in the present invention may be a commercially available lactose, or may be whole milk, skim milk, whey or the like containing lactose as a component. When whole milk containing lactose in the ingredients, skim milk, whey, etc. is used,
If necessary, it may be concentrated to increase the content of lactose before use. On the other hand, the glucuronic acid used in the present invention is a typical uronic acid, which includes mucopolysaccharides of animals and gum arabic of plants,
It is known as a constituent sugar such as hemicellulose and saponin. The glucuronic acid may be a commercially available glucuronic acid or a salt thereof.
【０００６】また、本発明で用いることのできるβ−ガ
ラクトシダーゼは、微生物あるいは動物由来のものが知
られており、一般的に用いられているアスペルギルス・
オリゼ、バチルス・サーキュランス、大腸菌などを起源
とするものを例示することができる。さらに、本発明で
用いることのできるβ−グルコシダーゼは、β−グルコ
シド結合を加水分解すると共にβ−ガラクトシダーゼ活
性を示すものであればよい。このようなβ−グルコシダ
ーゼは、微生物や高等動植物など広く自然界に存在する
ことが知られているものである。これらのβ−ガラクト
シダーゼやβ−グルコシダーゼは、精製酵素であっても
よいし、粗酵素であっても構わない。The β-galactosidase that can be used in the present invention is known to be of microbial or animal origin, and the commonly used Aspergillus
Examples thereof include those originating from Orise, Bacillus circulans, Escherichia coli and the like. Furthermore, the β-glucosidase that can be used in the present invention may be one that hydrolyzes the β-glucoside bond and exhibits β-galactosidase activity. Such β-glucosidase is known to exist widely in nature such as microorganisms and higher animals and plants. These β-galactosidase and β-glucosidase may be purified enzymes or crude enzymes.
【０００７】本発明のグルクロン酸含有オリゴ糖の製造
は、次のようにして行なわれる。乳糖が５〜６０重量
％、グルクロン酸が５〜６０重量％となるように反応液
を調製し、そのｐＨを３〜８とした後、β−ガラクトシ
ダーゼあるいはβ−グルコシダーゼを０．１〜２００単
位／ｍｌの濃度で作用させる。酵素反応の温度は、２０
〜７０℃が好ましい。また、酵素反応の時間は、生成す
るグルクロン酸含有オリゴ糖の収率に大きく影響を及ぼ
すので、それぞれの条件における最適の酵素反応時間に
ついて、実験的に確認しておくことが好ましい。なお、
反応液を９０℃、１分間加熱することにより、酵素反応
を停止することができる。このようにして得られたグル
クロン酸含有オリゴ糖は、適宜、濃縮、乾燥し、グルク
ロン酸含有オリゴ糖を含む組成物として用いることもで
きるが、通常行われているクロマトグラフ処理、例え
ば、活性炭クロマトグラフィー、イオン交換クロマトグ
ラフィー、ゲル濾過カラムクロマトグラフィー、あるい
は電気透析など一般的なオリゴ糖類の分離、精製方法に
従って純度を高めることもできる。The glucuronic acid-containing oligosaccharide of the present invention is produced as follows. The reaction solution was prepared so that lactose was 5 to 60% by weight and glucuronic acid was 5 to 60% by weight, and the pH was adjusted to 3 to 8, and then β-galactosidase or β-glucosidase was added in an amount of 0.1 to 200 units. Act at a concentration of / ml. The temperature of the enzyme reaction is 20
~ 70 ° C is preferred. In addition, since the time of the enzymatic reaction greatly affects the yield of the glucuronic acid-containing oligosaccharide to be produced, it is preferable to experimentally confirm the optimum enzymatic reaction time under each condition. In addition,
The enzyme reaction can be stopped by heating the reaction solution at 90 ° C. for 1 minute. The glucuronic acid-containing oligosaccharide obtained in this manner can be appropriately concentrated and dried and used as a composition containing the glucuronic acid-containing oligosaccharide, but it is generally used for chromatographic treatment, for example, activated carbon chromatography. The purity can also be increased according to a general method for separating and purifying oligosaccharides such as chromatography, ion exchange chromatography, gel filtration column chromatography, or electrodialysis.
【０００８】上記のようにして得られたグルクロン酸含
有オリゴ糖について、ＨＰＬＣでカルボニル基を分析
（検出器：ＵＶ ２０６ｎｍ）したところ、図１に示し
たように、ピーク１〜３が確認された。そこで、ピーク
１〜３を分取し、１Ｎのトリフルオロ酢酸で加水分解し
て構成糖を確認した。その結果を表１に示す。When the glucuronic acid-containing oligosaccharide obtained as described above was analyzed for carbonyl group by HPLC (detector: UV 206 nm), peaks 1 to 3 were confirmed as shown in FIG. . Therefore, peaks 1 to 3 were collected and hydrolyzed with 1N trifluoroacetic acid to confirm the constituent sugars. The results are shown in Table 1.
【０００９】[0009]
【表１】 ────────────────────────────────── Ｇａｌ ＧｌｃＵＡ＋ＧｌｃＵＡ−ｌａｃｔｏｎｅ（モル比） ────────────────────────────────── ピーク１ ３ １ ピーク２ ２ １ ピーク３ １ １ ──────────────────────────────────[Table 1] ────────────────────────────────── Gal GlcUA + GlcUA-lactone (molar ratio) ──── ────────────────────────────── Peak 1 3 1 Peak 2 2 1 Peak 3 1 1 ───────── ──────────────────────────
【００１０】したがって、本発明のグルクロン酸含有オ
リゴ糖は、ガラクトース１分子の単糖あるいはガラクト
ース２〜３分子よりなるオリゴ糖がグルクロン酸１分子
と結合したものであって、次の一般式で表わすことがで
きる。 （Ｇａｌ）ｎ−ＧｌｃＵＡ （ただし、式中、Ｇａｌはガラクトースを、ＧｌｃＵＡ
はグルクロン酸をそれぞれ示し、ｎは１〜３の整数を示
す。）そして、このピークのそれぞれの構成糖について
検索したところ、後述するようにピーク３がＯ−β−Ｄ
−ガラクトピラノシル−（１→３）−Ｄ−グルクロン酸
であり、またピーク２が、Ｏ−β−Ｄ−ガラクトピラノ
シル−（１→４）−Ｏ−β−Ｄ−ガラクトピラノシル−
（１→３）−Ｄ−グルクロン酸であることが確認され
た。Therefore, the glucuronic acid-containing oligosaccharide of the present invention is a monosaccharide of one molecule of galactose or an oligosaccharide consisting of two to three molecules of galactose bound to one molecule of glucuronic acid and represented by the following general formula. be able to. (Gal) n-GlcUA (In the formula, Gal represents galactose and GlcUA
Represents glucuronic acid, and n represents an integer of 1 to 3. ) Then, when the constituent sugars of this peak were searched, peak 3 was O-β-D as described later.
-Galactopyranosyl- (1 → 3) -D-glucuronic acid, and peak 2 is O-β-D-galactopyranosyl- (1 → 4) -O-β-D-galactopyrano. Sill
It was confirmed to be (1 → 3) -D-glucuronic acid.
【００１１】次に、このいずれのピークのグルクロン酸
含有オリゴ糖にも共通する理化学的性質について列挙す
る。 （１）色調： 乾燥粉末状態で白色 （２）溶解性： 水に可溶 （３）呈色反応： アニリン、ジフェニルアミン反応 ＋ カルバゾール硫酸反応 ＋ ニンヒドリン反応 − ビューレット反応 −Next, the physicochemical properties common to the oligosaccharides containing glucuronic acid at any of these peaks will be listed. (1) Color tone: White in a dry powder state (2) Solubility: Soluble in water (3) Color reaction: aniline, diphenylamine reaction + carbazole sulfate reaction + ninhydrin reaction − Burett reaction −
【００１２】ピーク３のグルクロン酸含有オリゴ糖を次
のようにして同定した。 （イ）分子量 Ｎｅｇａｔｉｖｅイオンモードで質量
分析計（ＦＡＢ−ＭＳ）を行った結果、ｍ／ｅ ３５５
( Ｍ−Ｈ )- であった。 （ロ）核磁気共鳴（ＮＭＲ）吸収 ５００ＭＨｚの分
光計を用いて重水中で測定した 1Ｈ−ＮＭＲスペクトル
を図２に示した。 （ハ）色調 凍結乾燥した粉末は白色を呈する。 （ニ）酸性、塩基性及び中性の区別 酸性を示すが、
塩は中性を示す。 （ホ）呈色反応 アニリン、ジフェニルアミン反応 ＋ カルバゾール硫酸反応 ＋ ニンヒドリン反応 − ビューレット反応 − （ヘ）構成糖 １．０Ｎ−ＴＦＡ（トリフルオロ酢
酸）で１００℃、３時間加水分解した結果、ガラクトー
スとグルクロン酸（グルクロノラクトン）が１：１のモ
ル比で生成した。 （ト）糖の結合様式 ＨＰＬＣによって分離精製し、
グルクロン酸のカルボニル基を重水素化ホウ素ナトリウ
ムであらかじめ還元した後、常法に従ってメチル化分析
を行い、ガスクロマトグラフィー質量分析計で同定した
結果、表２の通り、部分メチル化アルジトールアセテー
トを確認した。The glucuronic acid-containing oligosaccharide of peak 3 was identified as follows. (A) Molecular weight As a result of performing a mass spectrometer (FAB-MS) in Negative ion mode, m / e 355
(M−H) − . (B) Nuclear magnetic resonance (NMR) absorption 1 H-NMR spectrum measured in heavy water using a 500 MHz spectrometer is shown in FIG. (C) Color tone The freeze-dried powder appears white. (D) Distinction between acidic, basic and neutral
The salt is neutral. (E) Color reaction Aniline, diphenylamine reaction + carbazole sulfate reaction + ninhydrin reaction-Bullet reaction- (f) Constituent sugar 1.0 As a result of hydrolysis with N-TFA (trifluoroacetic acid) for 3 hours, galactose was obtained. Glucuronic acid (glucuronolactone) was produced in a 1: 1 molar ratio. (G) Sugar binding mode Separation and purification by HPLC,
After reducing the carbonyl group of glucuronic acid with sodium deuterium hydride in advance, methylation analysis was performed according to a conventional method, and the result was identified by gas chromatography-mass spectrometry. As a result, as shown in Table 2, partially methylated alditol acetate was confirmed. did.
【００１３】[0013]
【表２】 ────────────────────────────────── メチル化糖 モル比 ────────────────────────────────── ２，３，４，６−Ｏ−Ｍｅ−Ｇａｌｏｌ １ １，２，４，５，６−Ｏ−Ｍｅ−Ｇｌｃｏｌ* １ ────────────────────────────────── * ６位がＤ置換されたメチル化糖[Table 2] ────────────────────────────────── Methylated sugar molar ratio ─────── ─────────────────────────── 2,3,4,6-O-Me-Galol 1 1,2,4,5,6 -O-Me-Glcol * 1 ─────────────────────────────────── * 6th position was D-substituted Methylated sugar
【００１４】上記（イ）、（ロ）、（ヘ）及び（ト）に
示した性質により、ピーク３の化合物を、Ｏ−β−Ｄ−
ガラクトピラノシル−（１→３）−Ｄ−グルクロン酸で
あると同定した。Owing to the properties shown in (a), (b), (f) and (g) above, the compound of peak 3 was converted into O-β-D-
It was identified as galactopyranosyl- (1 → 3) -D-glucuronic acid.
【００１５】また、ピーク２のグルクロン酸含有オリゴ
糖を次のようにして同定した。 （イ）分子量 Ｎｅｇａｔｉｖｅイオンモードで質量
分析計（ＦＡＢ−ＭＳ）を行った結果、ｍ／ｅ ５１７
( Ｍ−Ｈ )- であった。 （ロ）核磁気共鳴（ＮＭＲ）吸収 ５００ＭＨｚの分
光計を用いて重水中で測定した 1Ｈ−ＮＭＲのスペクト
ルを図３に示した。 （ハ）色調 凍結乾燥した粉末は白色を呈する。 （ニ）酸性、塩基性及び中性の区別 酸性を示すが、
塩は中性を示す。 （ホ）呈色反応 アニリン、ジフェニルアミン反応 ＋ カルバゾール硫酸反応 ＋ ニンヒドリン反応 − ビューレット反応 − （ヘ）構成糖 １．０Ｎ−ＴＦＡ（トリフルオロ酢
酸）で１００℃、３時間加水分解した結果、ガラクトー
スとグルクロン酸（グルクロノラクトン）が２：１のモ
ル比で生成した。 （ト）糖の結合様式 ＨＰＬＣによって分離精製し、
グルクロン酸のカルボニル基を重水素化ホウ素ナトリウ
ムであらかじめ還元した後、常法に従ってメチル化分析
を行い、ガスクロマトグラフィー質量分析計で同定した
結果、表３の通り、部分メチル化アルジトールアセテー
トを確認した。The glucuronic acid-containing oligosaccharide of peak 2 was identified as follows. (A) Molecular weight As a result of performing a mass spectrometer (FAB-MS) in Negative ion mode, m / e 517
(M−H) − . (B) Nuclear magnetic resonance (NMR) absorption A 1 H-NMR spectrum measured in heavy water using a 500 MHz spectrometer is shown in FIG. (C) Color tone The freeze-dried powder appears white. (D) Distinction between acidic, basic and neutral
The salt is neutral. (E) Color reaction Aniline, diphenylamine reaction + carbazole sulfate reaction + ninhydrin reaction-Bullet reaction- (f) Constituent sugar 1.0 As a result of hydrolysis with N-TFA (trifluoroacetic acid) for 3 hours, galactose was obtained. Glucuronic acid (glucuronolactone) was produced in a 2: 1 molar ratio. (G) Sugar binding mode Separation and purification by HPLC,
After reducing the carbonyl group of glucuronic acid with sodium deuteride in advance, methylation analysis was performed according to a conventional method, and the result was identified by a gas chromatography mass spectrometer. As shown in Table 3, partially methylated alditol acetate was confirmed. did.
【００１６】[0016]
【表３】 ────────────────────────────────── メチル化糖 モル比 ────────────────────────────────── ２，３，４，６−Ｏ−Ｍｅ−Ｇａｌｏｌ １ ２，３，６−Ｏ−Ｍｅ−Ｇａｌｏｌ １ １，２，４，５，６−Ｏ−Ｍｅ−Ｇｌｃｏｌ* １ ────────────────────────────────── * ６位がＤ置換されたメチル化糖[Table 3] ────────────────────────────────── Methylated sugar molar ratio ─────── ─────────────────────────── 2,3,4,6-O-Me-Galol 1 2,3,6-O-Me -Galol 1, 1, 2, 4, 5, 6-O-Me-Glcol * 1 ─────────────────────────────── ──── * 6-position D-substituted methylated sugar
【００１７】上記の（イ）、（ロ）、（ヘ）及び（ト）
に示した性質により、ピーク２の化合物をＯ−β−Ｄ−
ガラクトピラノシル−（１→４）−Ｏ−β−Ｄ−ガラク
トピラノシル−（１→３）−Ｄ−グルクロン酸であると
同定した。The above (a), (b), (f) and (g)
Owing to the property shown in,
It was identified as galactopyranosyl- (1 → 4) -O-β-D-galactopyranosyl- (1 → 3) -D-glucuronic acid.
【００１８】本発明のグルクロン酸含有オリゴ糖は、カ
ルシウム、マグネシウム、鉄、銅、亜鉛などミネラルの
吸収性を向上する性質を有するので、糖衣錠やタブレッ
トなどの錠剤、顆粒剤、液剤、もしくはカプセルなどと
して経口的に投与できるミネラル吸収促進効果のある医
薬として用いることができる。また、各種飲食品、例え
ば飲料、スープ、チーズ、ゼリー、パン、麺類、ソーセ
ージなど、あるいはガムやキャンディーなどの菓子類に
添加することにより、ミネラル吸収促進食品素材として
用いることもできる。さらには、ミネラルの吸収を促進
する飼料添加物として用いることもできる。（本発明で
はこのような飼料添加物も含めて飼料と称する。）The glucuronic acid-containing oligosaccharide of the present invention has the property of improving the absorbability of minerals such as calcium, magnesium, iron, copper and zinc, and therefore, it is a tablet such as a sugar-coated tablet or a tablet, a granule, a liquid or a capsule. Can be used orally as a pharmaceutical having a mineral absorption promoting effect. Further, it can be used as a mineral absorption promoting food material by adding it to various foods and drinks, such as beverages, soups, cheeses, jellies, breads, noodles, sausages, and confectionery such as gums and candies. Further, it can be used as a feed additive that promotes absorption of minerals. (In the present invention, such feed additives are also referred to as feed.)
【００１９】本発明のグルクロン酸含有オリゴ糖の摂取
量については特に制限はないが、成人男子の場合、１０
ｍｇ／ｋｇ体重／日以上、望ましくは３０〜１００ｍｇ
／ｋｇ体重／日が適当である。１０ｍｇ／ｋｇ体重／日
未満では効果が殆ど認められず、１００ｍｇ／ｋｇ体重
／日以上を超えると何ら障害は無いが、効果の顕著な上
昇は見られない。従って、本発明における有効量は、こ
の程度の投与量となるように医薬、飲食品、飼料等に添
加してミネラル吸収促進作用を生じせしめるものをい
う。The intake of the glucuronic acid-containing oligosaccharide of the present invention is not particularly limited, but in the case of an adult male, it is 10
mg / kg body weight / day or more, preferably 30 to 100 mg
/ Kg body weight / day is appropriate. If the dose is less than 10 mg / kg body weight / day, almost no effect is observed, and if it exceeds 100 mg / kg body weight / day, there is no disorder, but the effect is not significantly increased. Therefore, the effective amount in the present invention refers to that which is added to medicines, foods and drinks, feeds and the like so as to give a dose of this level and which causes a mineral absorption promoting action.
【００２０】次に本発明を実施例を挙げて具体的に説明
する。Next, the present invention will be specifically described with reference to examples.
【実施例１】乳糖４００ｇとグルクロン酸ナトリウム１
１２ｇとを温水５００ｇに溶解した後、バチルス・サー
キュランス（Ｂａｃｉｌｌｕｓ ｃｉｒｃｕｌａｎｓ）
由来のβ−ガラクトシダーゼ（大和化成（株）製）５０
０ｍｇ（５０００単位）を加え、４０℃、８時間反応さ
せた。反応液を１００℃、１分間加熱して酵素反応を停
止した後、この反応液を直径１５ｃｍ×高さ３０ｃｍの
アニオン交換樹脂（Ｄｏｗ−１、酢酸型）を充填したカ
ラムに通液し、生成したグルクロン酸含有オリゴ糖を樹
脂に吸着させた。次に、十分量の水をカラムに通液して
中性糖を除去した後、０．５Ｍの酢酸ナトリウムを通液
してグルクロン酸含有オリゴ糖を含む画分を溶出した。
さらに、この溶出画分について、電気透析装置（ＴＳ−
２４型、膜面積：カチオン膜、アニオン膜共に９６０ｄ
ｍ2 、徳山曹達（株）製）で処理し、塩類及び未反応の
グルクロン酸を濃縮槽側に除去して、脱塩槽側に高純度
のグルクロン酸含有オリゴ糖を回収した。そして、減圧
濃縮後、凍結乾燥してグルクロン酸含有オリゴ糖の白色
粉末４７ｇを得た。この白色粉末についてＨＰＬＣで分
析したところ（Ｇａｌ）ｎ−ＧｌｃＵＡ（ｎ＝１〜３）
であることが確認さた。Example 1 Lactose 400 g and sodium glucuronate 1
After dissolving 12 g and 500 g of warm water, Bacillus circulans
Derived β-galactosidase (manufactured by Daiwa Kasei Co., Ltd.) 50
0 mg (5000 units) was added and reacted at 40 ° C. for 8 hours. After the reaction solution was heated at 100 ° C. for 1 minute to stop the enzymatic reaction, the reaction solution was passed through a column packed with an anion exchange resin (Dow-1, acetic acid type) having a diameter of 15 cm and a height of 30 cm to generate the reaction product. The glucuronic acid-containing oligosaccharide was adsorbed on the resin. Next, a sufficient amount of water was passed through the column to remove the neutral sugar, and then 0.5 M sodium acetate was passed through to elute the fraction containing the glucuronic acid-containing oligosaccharide.
Furthermore, this elution fraction was electrodialyzed (TS-
24 type, membrane area: both cation membrane and anion membrane 960d
m 2, was treated with Tokuyama Soda Co., Ltd.), to remove the glucuronic acid salts and unreacted concentration tank side to recover high-purity glucuronic acid containing oligosaccharides in desalination tank side. After concentration under reduced pressure and freeze-drying, 47 g of a white powder of glucuronic acid-containing oligosaccharide was obtained. When this white powder was analyzed by HPLC, (Gal) n-GlcUA (n = 1 to 3)
Was confirmed.
【００２１】このグルコン酸含有オリゴ糖のミネラル吸
収促進効果について、ラットの出納実験で検討した。実
験は、８週令のＳＤ系雄ラットを用い、１群６匹で行っ
た。実験食は表４に示したように各糖質を５％配合して
用いた。ミネラル吸収率の評価は実験食投与１週目に糞
便と尿を採取し***されたカルシウムおよびマグネシウ
ムを測定した。 ミネラル吸収率（％）＝〔（飼料摂取ミネラル量−糞便
***ミネラル量）／（飼料採取ミネラル量）〕×１００ その結果を図４に示す。本発明のグルコン酸含有オリゴ
糖は、カルシウム吸収促進物質として知られている乳糖
に比べて、有意にカルシウムやマグネシウムなどのミネ
ラル吸収を促進させた。The effect of this oligosaccharide containing gluconic acid on the mineral absorption was examined in a balance experiment in rats. The experiment was conducted using 8 week-old SD male rats, and 6 rats per group. As the experimental food, as shown in Table 4, 5% of each sugar was blended and used. To evaluate the mineral absorption rate, feces and urine were collected one week after the administration of the experimental diet, and excreted calcium and magnesium were measured. Mineral absorption rate (%) = [(feed intake mineral amount-fecal excretion mineral amount) / (feed collected mineral amount)] × 100 The results are shown in FIG. The gluconic acid-containing oligosaccharide of the present invention significantly promoted the absorption of minerals such as calcium and magnesium as compared with lactose known as a calcium absorption promoter.
【００２２】[0022]
【表４】 [Table 4]
【００２３】乳糖４００ｇとグルクロン酸ナトリウム１
００ｇとを温水５００ｇに溶解した後、アスペルギルス
・オリゼ（Ａｓｐｅｒｇｉｌｕｓ ｏｒｙｚａｅ）由来
のβ−ガラクトシダーゼ（新日本化学（株）製）１００
ｍｇ（６０００単位）を加え、４０℃、８時間反応させ
た。以下の操作は実施例１と同様に行い、グルクロン酸
含有オリゴ糖の白色粉末１２ｇを得た。400 g lactose and 1 glucuronate
After dissolving 100 g and 500 g of warm water, β-galactosidase (manufactured by Shin Nippon Kagaku Co., Ltd.) 100 derived from Aspergillus oryzae
mg (6000 units) was added and reacted at 40 ° C. for 8 hours. The following operations were performed in the same manner as in Example 1 to obtain 12 g of a white powder of glucuronic acid-containing oligosaccharide.
【００２４】[0024]
【実施例３】乳糖２００ｇとグルクロン酸１００ｇとを
温水７００ｇに溶解し、２０％水酸化ナトリウムでｐＨ
を6.0 に調整後、アーモンドのβ−グルコシダーゼ（シ
グマ社製）220 ｍｇ（3000単位）を加え、４０℃、１６
時間反応させた。以下の操作は実施例１と同様に行い、
グルクロン酸含有オリゴ糖の白色粉末１１ｇを得た。Example 3 200 g of lactose and 100 g of glucuronic acid were dissolved in 700 g of warm water, and the pH was adjusted with 20% sodium hydroxide.
After adjusting to 6.0, 220 mg (3000 units) of almond β-glucosidase (manufactured by Sigma) was added, and the mixture was placed at 40 ° C. and 16
Reacted for hours. The following operations are performed in the same manner as in Example 1,
11 g of white powder of glucuronic acid-containing oligosaccharide was obtained.
【００２５】[0025]
【実施例４】本発明のグルクロン酸含有オリゴ糖を配合
して吸収性を高めたカルシウム剤を調製した。カルシウ
ム２２００ｇ、コーンスターチ１２３２ｇ、結晶セルロ
ース１００ｇ、カルボキシメチルセルロースカルシウム
６８ｇ及びグルクロン酸含有オリゴ糖４００ｇをニーダ
ーで混合した後、水５００ｍｌを噴霧滴下しながら混練
した。次に、この混練物を２０メッシュのスクリーンを
セットした単軸オシレーターで造粒し、流動槽型乾燥機
で乾燥した。そして、この乾燥品をフラッシュミルで粉
砕し、整粒して打錠用粉体を得た。この打錠用粉体に滑
沢剤としてショ糖脂肪酸エステル８０ｇをＶ型混合機で
混合した後、直径１１ｍｍの杵をセットした錠剤機で打
錠し、平均重量０．３５ｇのタブレットを得た。Example 4 A calcium agent having enhanced absorbability was prepared by blending the glucuronic acid-containing oligosaccharide of the present invention. 2200 g of calcium, 1232 g of corn starch, 100 g of crystalline cellulose, 68 g of calcium carboxymethyl cellulose and 400 g of oligosaccharide containing glucuronic acid were mixed with a kneader, and then kneaded while spray-dripping 500 ml of water. Next, this kneaded product was granulated with a uniaxial oscillator equipped with a 20-mesh screen and dried with a fluidized-bed dryer. Then, this dried product was crushed by a flash mill and sized to obtain a tableting powder. 80 g of sucrose fatty acid ester as a lubricant was mixed with this tableting powder with a V-type mixer, and then tableted with a tablet machine in which a punch having a diameter of 11 mm was set to obtain tablets having an average weight of 0.35 g. .
【００２６】[0026]
【実施例５】常法に従い、表５の配合比によって果汁飲
料を製造した。Example 5 A fruit juice beverage was produced according to the compounding ratio shown in Table 5 according to a conventional method.
【表５】 ─────────────────────────────── 混合異性化糖 １５．０（重量％） 果汁 １０．０ クエン酸 １．０ グルクロン酸含有オリゴ糖 ０．１ 香料 ０．１ 水 ７３．８ ───────────────────────────────[Table 5] ─────────────────────────────── Mixed isomerized sugar 15.0 (% by weight) Fruit juice 10.0 Citric acid 1.0 Oligosaccharide containing glucuronic acid 0.1 Perfume 0.1 Water 73.8 ────────────────────────────── ──
【００２７】[0027]
【実施例６】常法に従い、表６の配合比によってゼリー
を製造した。Example 6 Jelly was produced according to the compounding ratio shown in Table 6 according to a conventional method.
【表６】 ─────────────────────────────── 果汁 ２０．０（重量％） グラニュー糖 １５．０ 水飴 ５．０ 寒天 １．０ グルクロン酸含有オリゴ糖 ０．５ 香料 ０．１ 水 ５８．４ ───────────────────────────────[Table 6] ─────────────────────────────── Fruit juice 20.0 (% by weight) Granulated sugar 15.0 Syringe 5 .0 Agar 1.0 Oligosaccharide containing glucuronic acid 0.5 Perfume 0.1 Water 58.4 ───────────────────────────── ───
【００２８】[0028]
【実施例７】表７の配合比によって犬飼育用飼料（ドッ
グフード）を製造した。[Example 7] A feed for dog breeding (dog food) was produced according to the mixing ratio shown in Table 7.
【表７】 ─────────────────────────────── 大豆粕 １３．７（重量％） 脱脂粉乳 １４．０ 大豆油 ４．０ コーン油 ２．０ パーム油 ２．０ トウモロコシ澱粉 ２３．０ 小麦粉 １５．０ 麩 ８．０ ビタミン混合物 ２．０ ミネラル混合物 ９．０ セルロース ２．３ グルクロン酸含有オリゴ糖 ５．０ ───────────────────────────────[Table 7] ─────────────────────────────── Soybean meal 13.7 (% by weight) Skim milk powder 14.0 Large Soybean oil 4.0 Corn oil 2.0 Palm oil 2.0 Corn starch 23.0 Wheat flour 15.0 Fuso 8.0 Vitamin mixture 2.0 Mineral mixture 9.0 Cellulose 2.3 Glucuronic acid-containing oligosaccharides 5.0 ─ ──────────────────────────────
【００２９】ビタミン混合物の組成は、表８に記載し
た。ミネラル混合物の組成は、表９に記載した。The composition of the vitamin mixture is set forth in Table 8. The composition of the mineral mixture is set forth in Table 9.
【表８】 ─────────────────────────────── ビタミンＡ １，５００ＩＵ ビタミンＤ3 ３００ＩＵ ビタミンＥ ６．８ｍｇ ビタミンＢ1 ０．９ｍｇ ビタミンＢ2 ０．４ｍｇ ビタミンＢ6 ０．５ｍｇ ビタミンＢ12 ３．４ｍｇ ビタミンＣ ５０．０ｍｇ パントテン酸 ４．０ｍｇ 葉酸 ０．２ｍｇ コリン ２００．０ｍｇ ビオチン ２４．４μｇ イノシトール ５０．０ｍｇ ナイアシン １０．５ｍｇ ─────────────────────────────── ショ糖を加えて全量を２ｇとした。[Table 8] ─────────────────────────────── Vitamin A 1,500 IU Vitamin D 3 300 IU Vitamin E 6.8 mg Vitamin B 1 0.9 mg Vitamin B 2 0.4 mg Vitamin B 6 0.5 mg Vitamin B 12 3.4 mg Vitamin C 50.0 mg Pantothenic acid 4.0 mg Folic acid 0.2 mg Choline 200.0 mg Biotin 24.4 μg Inositol 50.0 mg Niacin 10.5 mg ──────────────────────────────── Sucrose was added to make the total amount 2 g.
【００３０】[0030]
【表９】 ─────────────────────────────── ＣａＣＯ3 ３．０ｇ ＫＨ2 ＰＯ4 ２．０ｇ ＮａＨ2 ＰＯ4 １．５ｇ ＭｇＯ ０．５ｇ ＭｎＣＯ3 ４０．０ｍｇ ＦｅＣ6 Ｈ5 Ｏ7 ３０．０ｍｇ ７０％Ｚｎ０ １０．０ｍｇ ５５％ＣａＣＯ3 ４．５ｍｇ ＫｌＯ3 ０．６５ｍｇ Ｎａ2 ＳｅＯ3 ・５Ｈ2 Ｏ ０．０５ｍｇ ＣｒＫ（ＳＯ4 ）・１２Ｈ2 Ｏ ５．０ｍｇ ─────────────────────────────── ショ糖を加えて全量を９ｇとした。[Table 9] ─────────────────────────────── CaCO 3 3.0 g KH 2 PO 4 2.0 g NaH 2 PO 4 1.5 g MgO 0.5 g MnCO 3 40.0 mg FeC 6 H 5 O 7 30.0 mg 70% Zn0 10.0 mg 55% CaCO 3 4.5 mg KlO 3 0.65 mg Na 2 SeO 3 .5H 2 O 0. 05mg CrK (SO 4 ) ・ 12H 2 O 5.0mg ─────────────────────────────── Total amount including sucrose Was 9 g.
【００３１】[0031]
【発明の効果】本発明のグルクロン酸含有オリゴ糖は、
ミネラルの吸収性を促進する作用があり、このグルクロ
ン酸含有オリゴ糖を配合した医薬、飲食品及び飼料は、
ミネラルの補給に有用である。従って、骨粗鬆症やその
他の骨疾患の予防または治療あるいは動物の健康の維持
管理に用いられる。The glucuronic acid-containing oligosaccharide of the present invention is
It has the effect of promoting the absorbability of minerals, and pharmaceuticals, foods and drinks and feeds containing this glucuronic acid-containing oligosaccharide,
Useful for mineral supplementation. Therefore, it is used for the prevention or treatment of osteoporosis and other bone diseases or maintenance of animal health.
【図面の簡単な説明】[Brief description of drawings]
【図１】本発明のグルクロン酸含有オリゴ糖のＨＰＬＣ
による分析結果を示す。FIG. 1 HPLC of glucuronic acid-containing oligosaccharide of the present invention
The results of analysis by are shown.
【図２】図１Ｐ３のグルクロン酸含有オリゴ糖の核磁気
共鳴吸収スペクトルを示す。FIG. 2 shows a nuclear magnetic resonance absorption spectrum of the glucuronic acid-containing oligosaccharide shown in FIG. 1P3.
【図３】図１Ｐ２のグルクロン酸含有オリゴ糖の核磁気
共鳴スペクトルを示す。FIG. 3 shows a nuclear magnetic resonance spectrum of the glucuronic acid-containing oligosaccharide of FIG. 1P2.
【図４】実施例１のカルシウム吸収促進効果についての
実験結果を示す。FIG. 4 shows the experimental results on the calcium absorption promoting effect of Example 1.
Claims (6)
れるグルクロン酸含有オリゴ糖。（ただし、式中、Ｇａ
ｌはガラクトースを、ＧｌｃＵＡはグルクロン酸をそれ
ぞれ示し、ｎは１〜３の整数を示す。）1. A glucuronic acid-containing oligosaccharide represented by the general formula (Gal) n-GlcUA. (However, in the formula, Ga
1 represents galactose, GlcUA represents glucuronic acid, and n represents an integer of 1 to 3. )
れるグルクロン酸含有オリゴ糖が、Ｏ−β−Ｄ−ガラク
トピラノシル−（１→３）−Ｄ−グルクロン酸である請
求項１記載のオリゴ糖。2. The glucuronic acid-containing oligosaccharide represented by the general formula (Gal) n-GlcUA is O-β-D-galactopyranosyl- (1 → 3) -D-glucuronic acid. The described oligosaccharide.
れるグルクロン酸含有オリゴ糖が、Ｏ−β−Ｄ−ガラク
トピラノシル−（１→４）−Ｏ−β−Ｄ−ガラクトピラ
ノシル−（１→３）−Ｄ−グルクロン酸である請求項１
記載のオリゴ糖。3. A glucuronic acid-containing oligosaccharide represented by the general formula (Gal) n-GlcUA is O-β-D-galactopyranosyl- (1 → 4) -O-β-D-galactopyrano. Sil- (1 → 3) -D-glucuronic acid.
The described oligosaccharide.
β−ガラクトシダーゼ、あるいはβ−グルコシダーゼを
作用させてガラクトース転移反応を行わせて一般式（Ｇ
ａｌ）ｎ−ＧｌｃＵＡで表されるグルクロン酸含有オリ
ゴ糖を生成させ、これを採取することを特徴とする一般
式（Ｇａｌ）ｎ−ＧｌｃＵＡで表されるグルクロン酸含
有オリゴ糖の製造法。（ただし、式中、Ｇａｌはガラク
トースを、ＧｌｃＵＡはグルクロン酸をそれぞれ示し、
ｎは１〜３の整数を示す。）4. Lactose and glucuronic acid as starting materials,
The β-galactosidase or β-glucosidase is allowed to act to cause a galactose transfer reaction, and then the general formula (G
al) A method for producing a glucuronic acid-containing oligosaccharide represented by the general formula (Gal) n-GlcUA, which comprises producing a glucuronic acid-containing oligosaccharide represented by n-GlcUA and collecting the oligosaccharide. (However, in the formula, Gal represents galactose, GlcUA represents glucuronic acid,
n shows the integer of 1-3. )
れるグルクロン酸含有オリゴ糖を有効成分とするミネラ
ル吸収促進剤。（ただし、式中、Ｇａｌはガラクトース
を、ＧｌｃＵＡはグルクロン酸をそれぞれ示し、ｎは１
〜３の整数を示す。）5. A mineral absorption enhancer comprising a glucuronic acid-containing oligosaccharide represented by the general formula (Gal) n-GlcUA as an active ingredient. (However, in the formula, Gal represents galactose, GlcUA represents glucuronic acid, and n represents 1
Indicates an integer of ˜3. )
れる新規なグルクロン酸含有オリゴ糖を配合してミネラ
ル吸収性を高めたことを特徴とするミネラル吸収性の高
い飲食品及び飼料。（ただし、式中、Ｇａｌはガラクト
ースを、ＧｌｃＵＡはグルクロン酸をそれぞれ示し、ｎ
は１〜３の整数を示す。）6. A food / beverage product and a feed having high mineral absorbability, which is characterized in that a novel glucuronic acid-containing oligosaccharide represented by the general formula (Gal) n-GlcUA is blended to enhance mineral absorbability. (In the formula, Gal represents galactose, GlcUA represents glucuronic acid, and n
Represents an integer of 1 to 3. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5202587A JP2596509B2 (en) | 1992-12-11 | 1993-07-23 | Novel glucuronic acid-containing oligosaccharide, production method thereof and use thereof |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4-353409 | 1992-12-11 | ||
| JP35340992 | 1992-12-11 | ||
| JP5202587A JP2596509B2 (en) | 1992-12-11 | 1993-07-23 | Novel glucuronic acid-containing oligosaccharide, production method thereof and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06228181A true JPH06228181A (en) | 1994-08-16 |
| JP2596509B2 JP2596509B2 (en) | 1997-04-02 |
Family
ID=26513469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5202587A Expired - Fee Related JP2596509B2 (en) | 1992-12-11 | 1993-07-23 | Novel glucuronic acid-containing oligosaccharide, production method thereof and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2596509B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995024909A1 (en) * | 1994-03-15 | 1995-09-21 | Meiji Seika Kaisha, Ltd. | Osteoporosis preventing or treating agent |
| EP0988797A1 (en) * | 1996-10-08 | 2000-03-29 | Meiji Seika Kabushiki Kaisha | Compositions for postgastrectomic mineral supply |
| JP2001245690A (en) * | 2000-03-03 | 2001-09-11 | Yakult Honsha Co Ltd | Method for producing glycoside or oligosaccharide |
| JP2006089437A (en) * | 2004-09-27 | 2006-04-06 | Sanwa Denpun Kogyo Kk | Acidic oligosaccharide |
| JP2011132156A (en) * | 2009-12-24 | 2011-07-07 | Lion Corp | Oral liquid composition |
| JP2011136949A (en) * | 2009-12-28 | 2011-07-14 | Lion Corp | Liquid composition for oral administration |
-
1993
- 1993-07-23 JP JP5202587A patent/JP2596509B2/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995024909A1 (en) * | 1994-03-15 | 1995-09-21 | Meiji Seika Kaisha, Ltd. | Osteoporosis preventing or treating agent |
| US5900255A (en) * | 1994-03-15 | 1999-05-04 | Meiji Seika Kaisha, Ltd. | Material for prevention and treatment of osteoporosis |
| EP0988797A1 (en) * | 1996-10-08 | 2000-03-29 | Meiji Seika Kabushiki Kaisha | Compositions for postgastrectomic mineral supply |
| EP0988797A4 (en) * | 1996-10-08 | 2001-10-04 | Meiji Seika Co | Compositions for postgastrectomic mineral supply |
| JP2001245690A (en) * | 2000-03-03 | 2001-09-11 | Yakult Honsha Co Ltd | Method for producing glycoside or oligosaccharide |
| JP2006089437A (en) * | 2004-09-27 | 2006-04-06 | Sanwa Denpun Kogyo Kk | Acidic oligosaccharide |
| JP4741824B2 (en) * | 2004-09-27 | 2011-08-10 | 三和澱粉工業株式会社 | Acidic oligosaccharide |
| JP2011132156A (en) * | 2009-12-24 | 2011-07-07 | Lion Corp | Oral liquid composition |
| JP2011136949A (en) * | 2009-12-28 | 2011-07-14 | Lion Corp | Liquid composition for oral administration |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2596509B2 (en) | 1997-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0382355B1 (en) | Growth promoting agent for bacteria containing pullulan with or without dextran | |
| JPH0678367B2 (en) | Dietary fiber, method for producing the same, and bioactive agent containing the dietary fiber | |
| KR20040103914A (en) | Stimulation of the immune system with polydextrose | |
| JP2003522822A (en) | Inulin products with improved nutrition | |
| JP3514955B2 (en) | Calcium absorption enhancing composition | |
| JP5282932B2 (en) | Production method of polyphenol extract, osteoporosis preventive agent, carbohydrate digestive enzyme inhibitor, functional composition using these, and food composition, food composition for specified health use, quasi-drug containing this functional composition Product composition, pharmaceutical composition | |
| JP2011205913A (en) | Complex crystalline sugar of functional isomerized sugar and method for producing the same | |
| KR101300336B1 (en) | Composition having effect of lowering blood pressure and/or inhibiting increase in blood pressure and food and drink containing the same | |
| JPH11335285A (en) | Intestinal controlling and constipation improving medicine and food and drink, and animal feed containing the same | |
| JP2023073244A (en) | Intestinal environment improvement composition and method for manufacturing the same | |
| JPWO2007138905A1 (en) | Intestinal Eosinophil Inhibitory Composition | |
| JP3043888B2 (en) | Colorectal cancer prophylactic agent containing glucomannan partial hydrolyzate as active ingredient | |
| JP2019043867A (en) | Composition for promoting increase of Akkermansia muciniphila | |
| JP2596509B2 (en) | Novel glucuronic acid-containing oligosaccharide, production method thereof and use thereof | |
| JP3279694B2 (en) | Mineral absorption enhancer containing lactulose oligosaccharide as active ingredient | |
| EP1964855B1 (en) | Mineral absorption enhancer, food and feeding stuff | |
| JPS6316118B2 (en) | ||
| JP5340528B2 (en) | Lipid reducing agent in internal organs | |
| JP3279695B2 (en) | Mineral absorption enhancer containing branched galactooligosaccharide as active ingredient | |
| JPH0640922A (en) | Calcium preparation | |
| JP3559063B2 (en) | Bifidobacterium growth promoter | |
| JPH11155520A (en) | Use of sweetener or the like, or for imparting sweetness or the like; and drink, food or pharmaceutical to which sweetness is imparted or the like | |
| JPH1029945A (en) | Enteric metabolism-improving agent | |
| JPH0131487B2 (en) | ||
| JPH07316177A (en) | New oligosaccharide, production and use thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |