JPH07316177A - New oligosaccharide, production and use thereof - Google Patents
New oligosaccharide, production and use thereofInfo
- Publication number
- JPH07316177A JPH07316177A JP6326525A JP32652594A JPH07316177A JP H07316177 A JPH07316177 A JP H07316177A JP 6326525 A JP6326525 A JP 6326525A JP 32652594 A JP32652594 A JP 32652594A JP H07316177 A JPH07316177 A JP H07316177A
- Authority
- JP
- Japan
- Prior art keywords
- acetylneuraminic acid
- neu5ac
- gal
- oligosaccharide
- acid
- 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.)
- Pending
Links
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 53
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims abstract description 53
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical group CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims abstract description 51
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 30
- 239000011707 mineral Substances 0.000 claims abstract description 30
- 238000010521 absorption reaction Methods 0.000 claims abstract description 16
- 229930182830 galactose Natural products 0.000 claims abstract description 14
- 102000005936 beta-Galactosidase Human genes 0.000 claims abstract description 12
- 108010005774 beta-Galactosidase Proteins 0.000 claims abstract description 12
- 235000013305 food Nutrition 0.000 claims abstract description 11
- SQVRNKJHWKZAKO-LUWBGTNYSA-N N-acetylneuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-LUWBGTNYSA-N 0.000 claims abstract 5
- 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
- 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 claims description 6
- 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 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 238000006276 transfer reaction Methods 0.000 abstract description 6
- 235000013361 beverage Nutrition 0.000 abstract description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- 208000020084 Bone disease Diseases 0.000 abstract 1
- 208000001132 Osteoporosis Diseases 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 description 25
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 235000000346 sugar Nutrition 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 229910052742 iron Inorganic materials 0.000 description 7
- 230000001737 promoting effect Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006911 enzymatic reaction Methods 0.000 description 6
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- 239000011790 ferrous sulphate Substances 0.000 description 5
- 235000003891 ferrous sulphate Nutrition 0.000 description 5
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000193752 Bacillus circulans Species 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000007502 anemia Diseases 0.000 description 3
- 235000013351 cheese Nutrition 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 102000001554 Hemoglobins Human genes 0.000 description 2
- 108010054147 Hemoglobins Proteins 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 206010028813 Nausea Diseases 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
- 229940124532 absorption promoter Drugs 0.000 description 2
- KBGAYAKRZNYFFG-BOHATCBPSA-N aceneuramic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](NC(=O)C)[C@@H](O)[C@H](O)[C@H](O)CO KBGAYAKRZNYFFG-BOHATCBPSA-N 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- -1 etc. Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008693 nausea Effects 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 2
- 125000005630 sialyl group Chemical group 0.000 description 2
- 235000020183 skimmed milk Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 235000008939 whole milk Nutrition 0.000 description 2
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 206010022971 Iron Deficiencies Diseases 0.000 description 1
- 240000002129 Malva sylvestris Species 0.000 description 1
- 235000006770 Malva sylvestris Nutrition 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 102000005348 Neuraminidase Human genes 0.000 description 1
- 108010006232 Neuraminidase Proteins 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JDGPQNJYYADFKP-UHFFFAOYSA-N aniline;n-phenylaniline Chemical compound NC1=CC=CC=C1.C=1C=CC=CC=1NC1=CC=CC=C1 JDGPQNJYYADFKP-UHFFFAOYSA-N 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- CADNYOZXMIKYPR-UHFFFAOYSA-B ferric pyrophosphate Chemical compound [Fe+3].[Fe+3].[Fe+3].[Fe+3].[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O CADNYOZXMIKYPR-UHFFFAOYSA-B 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 235000021255 galacto-oligosaccharides Nutrition 0.000 description 1
- 150000003271 galactooligosaccharides Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction 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
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QKFTYFYIYXTFBX-BKSOAOGQSA-M sodium;(2s,4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylate Chemical compound [Na+].CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C([O-])=O)O[C@H]1[C@H](O)[C@H](O)CO QKFTYFYIYXTFBX-BKSOAOGQSA-M 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 235000021195 test diet Nutrition 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規なＮ−アセチルノ
イラミン酸結合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Ｎ−アセチルノイラミ
ン酸結合オリゴ糖を有効成分とするミネラル吸収促進
剤、あるいは、このような新規なＮ−アセチルノイラミ
ン酸結合オリゴ糖を配合してミネラルの吸収性を高めた
飲食品または飼料に関する。TECHNICAL FIELD The present invention relates to a novel N-acetylneuraminic acid-linked oligosaccharide and a method for producing the same. The present invention also comprises a mineral absorption promoter containing such a novel N-acetylneuraminic acid-bonded oligosaccharide as an active ingredient, or a novel N-acetylneuraminic acid-bonded oligosaccharide. The present invention relates to foods and drinks or feeds with enhanced absorption of minerals.
【０００２】[0002]
【従来の技術】近年、糖加水分解酵素の糖転移反応によ
り合成された種々のオリゴ糖は、食品の機能性素材とし
て盛んに利用されている。そして、これらのオリゴ糖に
ついては、そのほとんどがビフィズス菌増殖作用を目的
としており、ミネラルの吸収促進作用を目的とするもの
は、非常に少ない現状にある。2. Description of the Related Art In recent years, various oligosaccharides synthesized by sugar transfer reaction of sugar hydrolase have been widely used as functional materials for foods. Most of these oligosaccharides are aimed at the bifidobacteria-proliferating action, and very few are aimed at the mineral absorption-promoting action.
【０００３】ところで、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であり、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、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、ミネラルの含量が高い食品と共
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。さらには、出血や鉄欠乏による貧血の治療
や改善には、クエン酸鉄、ピロリン酸鉄、塩化鉄、硫酸
鉄などの鉄剤やビタミンＢ12製剤などが用いられている
が、これらの製剤は体内での吸収率が非常に低いため比
較的多量に投与しなければならない。しかし、これらの
製剤を経口投与する場合、多量に投与すると消化管壁の
出血や様々な副作用（吐気、むかつき、便秘など）を引
き起こすという問題があった。[0003] By the way, the calcium intake of the Japanese has been conventionally lower than the nutritional requirement, and the intake of calcium is 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, copper, and magnesium tend to be deficient, and there is growing interest in substances that promote absorption of minerals as well as foods with high mineral contents. Furthermore, iron agents such as iron citrate, iron pyrophosphate, iron chloride, and iron sulfate, and vitamin B 12 preparations are used to treat and improve anemia due to bleeding and iron deficiency. It has to be given in relatively large doses due to its very low absorption rate. However, when these preparations are orally administered, there is a problem in that a large amount causes bleeding of the gastrointestinal wall and various side effects (nausea, nausea, constipation, etc.).
【０００４】一方、シアル酸を構成要素とする糖鎖の製
造に関しては、シアリル基供与体とシアリル基受容体と
をシアリダーゼの存在下で転移反応を行わせることによ
り合成する方法が知られている（特開平6- 38784号公
報）。しかし、β−ガラクトシダーゼの転移反応により
シアル酸を構成要素とする糖鎖を合成した例は報告され
ていない。On the other hand, regarding the production of sugar chains having sialic acid as a constituent element, a method is known in which a sialyl group donor and a sialyl group acceptor are synthesized by carrying out a transfer reaction in the presence of sialidase. (JP-A-6-38784). However, no example has been reported in which a sugar chain having sialic acid as a constituent element was synthesized by a β-galactosidase transfer reaction.
【０００５】[0005]
【発明が解決しようとする課題】本発明者らは、上述の
状況を鑑み、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−ガラクトシダーゼのガ
ラクトース転移反応によって乳糖とＮ−アセチルノイラ
ミン酸とから合成した新規なＮ−アセチルノイラミン酸
結合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Ｎ−アセチルノイラミン酸結合オリゴ糖を提
供することを課題とする。また、本発明は、新規なＮ−
アセチルノイラミン酸結合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Ｎ
−アセチルノイラミン酸結合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Ｎ−アセチルノイラミン
酸結合オリゴ糖を配合してミネラルの吸収性を高めた飲
食品または飼料を提供することを課題とする。DISCLOSURE OF THE INVENTION In view of the above situation, the present inventors have made earnest studies on substances that improve the absorbability of minerals, and found that lactose and N-acetyl are transferred by the galactose transfer reaction of β-galactosidase. The present inventors have found that a novel N-acetylneuraminic acid-bonded oligosaccharide synthesized from neuraminic acid improves the absorbability of minerals, and completed the present invention. Therefore, an object of the present invention is to provide a novel N-acetylneuraminic acid-linked oligosaccharide. The present invention also provides a novel N-
It is an object to provide a method for producing an acetylneuraminic acid-linked oligosaccharide. Furthermore, the present invention provides a novel N
-Providing a food / beverage product or feed in which mineral absorption is enhanced by incorporating a mineral absorption promoter containing acetylneuraminic acid-bound oligosaccharide as an active ingredient and a novel N-acetylneuraminic acid-bound oligosaccharide And
【０００６】[0006]
【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Ｎ−アセチルノイラミン酸が結合した次の一
般式で示される新規なＮ−アセチルノイラミン酸含有オ
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Ｎ−アセチルノイラミン酸含有オリ
ゴ糖は、乳糖とＮ−アセチルノイラミン酸とにβ−ガラ
クトシダーゼを作用させてガラクトース転移反応を行な
わせ、これを単離することによって得ることができる。The compound of the present invention is a novel N-acetylneuraminic acid-containing oligosaccharide represented by the following general formula in which galactose and N-acetylneuraminic acid are bound to each other. It has the property of improving absorbency. This novel N-acetylneuraminic acid-containing oligosaccharide can be obtained by allowing β-galactosidase to act on lactose and N-acetylneuraminic acid to cause a galactose transfer reaction, and isolating this.
【０００７】（Ｇａｌ）ｎ−Ｎｅｕ５Ａｃ （ただし、式中、Ｇａｌはガラクトースを、Ｎｅｕ５Ａ
ｃはＮ−アセチルノイラミン酸をそれぞれ示し、ｎは１
〜２の整数を示す。）(Gal) n-Neu5Ac (where Gal represents galactose and Neu5A
c represents N-acetylneuraminic acid, and n is 1
Indicates an integer of ˜2. )
【０００８】本発明の化合物を得るためには、乳糖とし
て、一般に市販されている乳糖をそのまま用いても良い
し、また、乳糖を成分中に含有する全乳、脱脂乳、チー
ズホエーなどを用いても良い。なお、全乳、脱脂乳、チ
ーズホエーなどを用いる場合は、必要に応じて濃縮し、
乳糖含量を高めて用いると良い。In order to obtain the compound of the present invention, as lactose, lactose which is generally commercially available may be used as it is, or whole milk, skim milk, cheese whey containing lactose in its components may be used. May be. When using whole milk, skim milk, cheese whey, etc., concentrate as necessary,
It is recommended to increase the lactose content before use.
【０００９】一方、Ｎ−アセチルノイラミン酸として、
一般に市販されているＮ−アセチルノイラミン酸あるい
はその塩類を用いると良い。なお、このＮ−アセチルノ
イラミン酸あるいはその塩類は、高度に精製されたもの
でなくても用いることができる。On the other hand, as N-acetylneuraminic acid,
Generally, commercially available N-acetylneuraminic acid or salts thereof may be used. The N-acetylneuraminic acid or its salts can be used even if it is not highly purified.
【００１０】また、本発明では、β−ガラクトシダーゼ
として、好ましくは微生物あるいは動物由来のもの、例
えば、アスペルギルス・オリゼ(Aspergillus oryzae)、
バチルス・サーキュランス(Bacillus circulans)、大腸
菌(Escherichia coli)などの微生物が生産する酵素、あ
るいは、ウシ肝臓やウシ睾丸などから抽出される酵素を
用いることができる。なお、このβ−ガラクトシダーゼ
は、高度に精製されたものでなくても良く、粗酵素とし
て用いることもできる。In the present invention, the β-galactosidase is preferably of microbial or animal origin, such as Aspergillus oryzae,
An enzyme produced by a microorganism such as Bacillus circulans or Escherichia coli, or an enzyme extracted from bovine liver, bovine testis or the like can be used. The β-galactosidase does not have to be highly purified and can be used as a crude enzyme.
【００１１】本発明のＮ−アセチルノイラミン酸結合オ
リゴ糖の製造条件は、次の通りである。乳糖が５〜60重
量％、Ｎ−アセチルノイラミン酸が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−
ガラクトシダーゼを 0.1〜 200単位／mlの濃度で作用さ
せる。酵素反応の温度は、５〜60℃が好ましい。また、
酵素反応の時間は、生成するＮ−アセチルノイラミン酸
結合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、反応液について
は、90℃以上の温度で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。The production conditions of the N-acetylneuraminic acid-linked oligosaccharide of the present invention are as follows. A reaction solution was prepared such that lactose was 5 to 60% by weight and N-acetylneuraminic acid was 5 to 60% by weight, and the pH was adjusted to 3 to 8 and then β-
Galactosidase is allowed to act at a concentration of 0.1-200 units / ml. The temperature of the enzyme reaction is preferably 5 to 60 ° C. Also,
Since the time of the enzymatic reaction has a great influence on the yield of the N-acetylneuraminic acid-linked oligosaccharide produced, it is preferable to experimentally confirm the optimal enzymatic reaction time under each condition. The enzyme reaction can be stopped by heating the reaction solution at a temperature of 90 ° C. or higher for 1 minute.
【００１２】このようにして得られたＮ−アセチルノイ
ラミン酸結合オリゴ糖は、適宜、濃縮、乾燥し、Ｎ−ア
セチルノイラミン酸結合オリゴ糖含有組成物として用い
ることもできるが、通常行われているオリゴ糖類の分
離、精製方法、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を行うことにより、
純度を高めることもできる。The N-acetylneuraminic acid-bonded oligosaccharide thus obtained can be concentrated and dried appropriately and used as a composition containing N-acetylneuraminic acid-bonded oligosaccharide. Isolation of the oligosaccharides, purification method, for example, activated carbon chromatography, ion exchange chromatography, gel filtration column chromatography, or by performing electrodialysis,
Purity can also be increased.
【００１３】上記のようにして得られたＮ−アセチルノ
イラミン酸結合オリゴ糖について、ＨＰＬＣでカルボニ
ル基を分析（検出器：UV 206nm、カラム：バイオラッド
ＨＰＸ−87Ｈ）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。その中、ピーク３はＮ−アセチ
ルノイラミン酸であるので、ピーク１及びピーク２を分
取し、β−ガラクトシダーゼで加水分解してその構成糖
を確認した。その結果を表１に示す。The N-acetylneuraminic acid-bonded oligosaccharide obtained as described above was analyzed for carbonyl group by HPLC (detector: UV 206 nm, column: Bio-Rad HPX-87H). As described above, peaks 1 to 3 were confirmed. Among them, since peak 3 is N-acetylneuraminic acid, peak 1 and peak 2 were fractionated and hydrolyzed with β-galactosidase to confirm its constituent sugars. The results are shown in Table 1.
【００１４】[0014]
【表１】 [Table 1]
【００１５】したがって、本発明のＮ−アセチルノイラ
ミン酸結合オリゴ糖は、ガラクトース１分子の単糖ある
いはガラクトース２分子よりなるオリゴ糖がＮ−アセチ
ルノイラミン酸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。Therefore, the N-acetylneuraminic acid-linked oligosaccharide of the present invention is a monosaccharide of one molecule of galactose or an oligosaccharide composed of two molecules of galactose bound to one molecule of N-acetylneuraminic acid. It can be expressed by the following general formula.
【００１６】（Ｇａｌ）ｎ−Ｎｅｕ５Ａｃ （ただし、式中、Ｇａｌはガラクトースを、Ｎｅｕ５Ａ
ｃはＮ−アセチルノイラミン酸をそれぞれ示し、ｎは１
〜２の整数を示す。）(Gal) n-Neu5Ac (where Gal represents galactose and Neu5A
c represents N-acetylneuraminic acid, and n is 1
Indicates an integer of ˜2. )
【００１７】そして、このピーク２のＮ−アセチルノイ
ラミン酸結合オリゴ糖について検索したところ、後述す
るように、Ｏ−β−Ｄ−ガラクトピラノシル−（１→
８）−Ｎ−アセチルノイラミン酸及びＯ−β−Ｄ−ガラ
クトピラノシル−（１→９）−Ｎ−アセチルノイラミン
酸であることが確認された。When the N-acetylneuraminic acid-bonded oligosaccharide of peak 2 was searched, as described later, O-β-D-galactopyranosyl- (1 →
8) -N-acetylneuraminic acid and O-β-D-galactopyranosyl- (1 → 9) -N-acetylneuraminic acid were confirmed.
【００１８】次に、この両方のピークのＮ−アセチルノ
イラミン酸結合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 ＋ レゾルシノール−硫酸銅−塩酸反応 ＋ チオバルビツール酸反応 ＋ ニンヒドリン反応 − ビューレット反応 −Next, the physicochemical properties common to the N-acetylneuraminic acid-linked oligosaccharides of both peaks will be listed. (1) Color tone White in dry powder state (2) Solubility Soluble in water (3) Color reaction aniline-diphenylamine reaction + resorcinol-sulfate-hydrochloric acid reaction + thiobarbituric acid reaction + ninhydrin reaction − buretet reaction −
【００１９】また、ピーク２に含まれるＯ−β−Ｄ−ガ
ラクトピラノシル−（１→８）−Ｎ−アセチルノイラミ
ン酸及びＯ−β−Ｄ−ガラクトピラノシル−（１→９）
−Ｎ−アセチルノイラミン酸を次のようにして同定し
た。Further, O-β-D-galactopyranosyl- (1 → 8) -N-acetylneuraminic acid and O-β-D-galactopyranosyl- (1 → 9) contained in peak 2 are contained.
-N-acetylneuraminic acid was identified as follows.
【００２０】（イ）分子量 Negativeイオンモードで
質量分析(FAB-MS)を行った結果、それぞれm/e 470(M-H)
- であった。 （ロ）核磁気共鳴（ＮＭＲ）吸収 500MHzの分光計を
用い重水中で測定したＯ−β−Ｄ−ガラクトピラノシル
−（１→８）−Ｎ−アセチルノイラミン酸の 1Ｈ−ＮＭ
Ｒスペクトルを図２に、13Ｃ−ＮＭＲスペクトルを図３
に示す。また、Ｏ−β−Ｄ−ガラクトピラノシル−（１
→９）−Ｎ−アセチルノイラミン酸の 1Ｈ−ＮＭＲスペ
クトルを図４に、13Ｃ−ＮＭＲスペクトルを図５に示
す。 （ハ）色調 凍結乾燥した粉末はそれぞれ白色を呈す
る。 （ニ）酸性、塩基性及び中性の区別 それぞれ酸性を
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 ＋ レゾルシノール−硫酸銅−塩酸反応 ＋ エーリッヒ反応 ＋ ニンヒドリン反応 − ビューレット反応 − （ヘ）構成糖 β−ガラクトシダーゼで40℃、24時間
加水分解した結果、ガラクトースとＮ−アセチルノイラ
ミン酸がそれぞれ１：１のモル比で生成した。 （ト）糖の結合様式 ピーク２のＮ−アセチルノイラミン酸結合オリゴ糖を活
性炭で分離、精製した後、常法に従ってメチル化分析を
行った。次に、メチル化糖を0.3N塩酸−メタノールで75
℃、18時間メタノリシスした。さらに、アセチル化した
後、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、部分メチル化糖を確認した。(B) Molecular weight As a result of mass spectrometry (FAB-MS) in Negative ion mode, m / e 470 (MH) was obtained.
- it was. (B) Nuclear magnetic resonance (NMR) absorption 1 H-NM of O-β-D-galactopyranosyl- (1 → 8) -N-acetylneuraminic acid measured in a heavy water using a 500 MHz spectrometer.
The R spectrum is shown in FIG. 2 and the 13 C-NMR spectrum is shown in FIG.
Shown in. In addition, O-β-D-galactopyranosyl- (1
→ 9) The 1 H-NMR spectrum and the 13 C-NMR spectrum of -N-acetylneuraminic acid are shown in Fig. 4 and Fig. 5, respectively. (C) Color tone Each of the freeze-dried powders has a white color. (D) Distinction between acidity, basicity and neutrality Each shows acidity, but a salt shows neutrality. (E) Color reaction aniline, diphenylamine reaction + resorcinol-copper sulfate-hydrochloric acid reaction + Erich reaction + ninhydrin reaction-Burelet reaction- (f) Constituent sugar As a result of hydrolysis with β-galactosidase for 24 hours at 40 ° C, galactose and N-acetylneuraminic acid was produced at a molar ratio of 1: 1 respectively. (G) Binding mode of sugar After the N-acetylneuraminic acid-bound oligosaccharide of peak 2 was separated and purified with activated carbon, methylation analysis was performed according to a conventional method. Next, the methylated sugar is treated with 0.3N hydrochloric acid-methanol to 75%.
It was subjected to methanolysis at 18 ° C for 18 hours. Furthermore, after acetylation, as a result of identification by a gas chromatography mass spectrometer, as shown in Table 2, partially methylated sugars were confirmed.
【００２１】[0021]
【表２】 [Table 2]
【００２２】上記（イ）、（ロ）、（ヘ）及び（ト）に
示した性質により、ピーク２に含まれる化合物をＯ−β
−Ｄ−ガラクトピラノシル−（１→８）−Ｎ−アセチル
ノイラミン酸及びＯ−β−Ｄ−ガラクトピラノシル−
（１→９）−Ｎ−アセチルノイラミン酸と同定した。Owing to the properties shown in (a), (b), (f) and (g) above, the compound contained in peak 2 can be converted into O-β.
-D-galactopyranosyl- (1 → 8) -N-acetylneuraminic acid and O-β-D-galactopyranosyl-
It was identified as (1 → 9) -N-acetylneuraminic acid.
【００２３】本発明のＮ−アセチルノイラミン酸結合オ
リゴ糖は、ミネラルの吸収性を促進させる性質を有する
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。The N-acetylneuraminic acid-bonded oligosaccharide of the present invention has the property of promoting the absorbability of minerals, and therefore, it is a tablet such as a sugar-coated tablet or a tablet, a granule, a liquid preparation,
Alternatively, it can be used as a capsule or the like as a pharmaceutical having an effect of promoting mineral absorption that can be orally administered.
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.
【００２４】本発明のＮ−アセチルノイラミン酸結合オ
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、10mg／kg体重／日以上、望ましくは30〜100
mg／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。したがって、本発明における有効量は、上記の範囲
の投与量となるように医薬、飲食品、飼料などに添加し
てミネラル吸収促進作用を生じさせる量をいう。The amount of the N-acetylneuraminic acid-linked oligosaccharide of the present invention to be taken 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. At less than 10 mg / kg body weight / day, almost no effect was observed, and at more than 100 mg / kg body weight / day, there was no disorder, but no marked increase in effect was observed. Therefore, the effective amount in the present invention refers to an amount which is added to a drug, a food or drink, a feed or the like so as to give a dose within the above range and which causes a mineral absorption promoting action.
【００２５】次に実施例及び試験例を挙げて本発明を具
体的に説明する。Next, the present invention will be specifically described with reference to examples and test examples.
【００２６】[0026]
【実施例１】乳糖400gとＮ−アセチルノイラミン酸ナト
リウム112gとを温水500gに溶解し、酢酸でpHを 6.0に調
整した後、バチルス・サーキュランス(Bacillus circul
ans)由来のβ−ガラクトシダーゼ（大和化成株式会社）
100mgを加え、40℃で48時間反応させた。そして、この
反応液を 100℃で１分間加熱して酵素反応を停止させた
後、アニオン交換樹脂（Dow-１、酢酸型、室町化学株式
会社）を充填した直径15cm×長さ30cmのカラムに通液
し、生成したＮ−アセチルノイラミン酸結合オリゴ糖と
未反応のＮ−アセチルノイラミン酸を樹脂に吸着させ
た。次に、このカラムに充分量の脱イオン水を通液して
酵素反応で生成したガラクトオリゴ糖及びその他の中性
糖を除去した後、０〜0.3Mで酢酸ナトリウム溶液を用い
たグラジェント溶出により、樹脂に吸着したＮ−アセチ
ルノイラミン酸結合オリゴ糖とＮ−アセチルノイラミン
酸を溶出した。なお、この溶出条件によってＮ−アセチ
ルノイラミン酸結合オリゴ糖とＮ−アセチルノイラミン
酸とを完全に分離することが可能となった。さらに、Ｎ
−アセチルノイラミン酸結合オリゴ糖を含む溶出画分を
電気透析（モデルTS−24型、膜面積：カチオン膜、アニ
オン膜共に960dm2、トクヤマ株式会社）により脱塩し、
減圧濃縮した後、凍結乾燥して純度95％のＮ−アセチル
ノイラミン酸結合オリゴ糖の白色粉末 40gを得た。Example 1 400 g of lactose and 112 g of sodium N-acetylneuraminate were dissolved in 500 g of warm water, the pH was adjusted to 6.0 with acetic acid, and then Bacillus circul
ans) -derived β-galactosidase (Daiwa Kasei Co., Ltd.)
100 mg was added and reacted at 40 ° C. for 48 hours. Then, after heating this reaction solution at 100 ° C for 1 minute to stop the enzymatic reaction, it was placed in a column with a diameter of 15 cm and a length of 30 cm packed with anion exchange resin (Dow-1, acetic acid type, Muromachi Chemical Co., Ltd.). After passing through the liquid, the produced N-acetylneuraminic acid-bound oligosaccharide and unreacted N-acetylneuraminic acid were adsorbed on the resin. Next, a sufficient amount of deionized water was passed through this column to remove galactooligosaccharides and other neutral sugars produced by the enzymatic reaction, and then by gradient elution with a sodium acetate solution at 0 to 0.3M. The N-acetylneuraminic acid-bound oligosaccharide and N-acetylneuraminic acid adsorbed on the resin were eluted. The elution conditions made it possible to completely separate N-acetylneuraminic acid-bonded oligosaccharide and N-acetylneuraminic acid. Furthermore, N
-The elution fraction containing the acetylneuraminic acid-bonded oligosaccharide was desalted by electrodialysis (model TS-24 type, membrane area: 960 dm 2 for both cation membrane and anion membrane, Tokuyama Corporation),
After concentration under reduced pressure, the residue was freeze-dried to obtain 40 g of white powder of N-acetylneuraminic acid-linked oligosaccharide having a purity of 95%.
【００２７】[0027]
【実施例２】乳糖200gとＮ−アセチルノイラミン酸 50g
とを温水250gに溶解し、水酸化ナトリウムでpHを 6.0に
調整した後、バチルス・サーキュランス(Bacillus circ
ulans)由来のβ−ガラクトシダーゼ（大和化成株式会
社）50mgを加え、40℃で72時間反応させた。そして、以
下実施例１に記載したと同様の操作を行い、純度95％の
Ｎ−アセチルノイラミン酸結合オリゴ糖の白色粉末を 2
0g得た。Example 2 200 g of lactose and 50 g of N-acetylneuraminic acid
Was dissolved in 250 g of warm water, the pH was adjusted to 6.0 with sodium hydroxide, and then Bacillus circulans
ulans) -derived β-galactosidase (Daiwa Kasei Co., Ltd.) (50 mg) was added, and the mixture was reacted at 40 ° C. for 72 hours. Then, the same operation as described in Example 1 was performed to obtain a white powder of N-acetylneuraminic acid-linked oligosaccharide having a purity of 95%.
I got 0g.
【００２８】[0028]
【試験例１】実施例２に記載した方法で得られたＮ−ア
セチルノイラミン酸結合オリゴ糖について、ラットを用
いた動物実験でミネラルの吸収促進効果を検討した。TEST EXAMPLE 1 Regarding the N-acetylneuraminic acid-bound oligosaccharide obtained by the method described in Example 2, the effect of promoting absorption of minerals was examined in animal experiments using rats.
【００２９】動物実験は８週齢のＳＤ系雄ラットを用
い、１群６匹で行なった。実験食は表３に示したように
各糖質を５重量％配合したものを用いた。Animal experiments were carried out using 8-week-old male SD rats, each group consisting of 6 rats. As the experimental food, as shown in Table 3, a mixture containing 5% by weight of each sugar was used.
【００３０】[0030]
【表３】 [Table 3]
【００３１】また、各実験食の栄養成分値を表４に、ミ
ネラル成分値を表５に示した。Table 4 shows the nutritional component values and Table 5 the mineral component values of each experimental diet.
【００３２】[0032]
【表４】 [Table 4]
【００３３】[0033]
【表５】 [Table 5]
【００３４】また、ミネラル吸収率の評価については、
実験食投与１週目に糞便と尿を採取し、排泄されたカル
シウムとマグネシウムを測定し、以下の式により算出し
た。Regarding the evaluation of 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 and calculated by the following formula.
【００３５】ミネラル吸収率（％）＝〔（摂取ミネラル
量−排泄ミネラル量）／（摂取ミネラル量）〕×100Mineral absorption rate (%) = [(intake mineral amount-excreted mineral amount) / (intake mineral amount)] × 100
【００３６】その結果を図６に示す。それによると、本
発明のＮ−アセチルノイラミン酸結合オリゴ糖投与群
は、カルシウム吸収物質として知られている乳糖投与群
に比べて、カルシウムやマグネシウムなどのミネラル吸
収を促進させることが判った。The results are shown in FIG. According to this, it was found that the N-acetylneuraminic acid-bonded oligosaccharide administration group of the present invention promotes absorption of minerals such as calcium and magnesium as compared with the lactose administration group known as a calcium absorbing substance.
【００３７】[0037]
【試験例２】21日齢のウィスター系ラット (体重が45〜
50g)に、鉄含量を0.25mg／100g飼料とした除鉄食（オリ
エンタル酵母社製）を３週間与え、血中ヘモグロビン値
が7g／100ml 以下の貧血ラットを作成した。そして、１
群５匹とし、その後も除鉄食を与え続けながら、下記に
示した試験飼料を１ml／日、６週間強制経口投与した。 試験群１：除鉄食のみ 試験群２：硫酸第一鉄を鉄として 0.2mg／ml 試験群３：硫酸第一鉄を鉄として 0.2mg／ml＋Ｎ−アセ
チルノイラミン酸結合オリゴ糖を 200mg／ml 試験群４：硫酸第一鉄を鉄として 0.2mg／ml＋Ｎ−アセ
チルノイラミン酸を 200mg／ml 試験群５：硫酸第一鉄を鉄として 0.2mg／ml＋乳糖を 2
00mg／ml[Test Example 2] 21-day-old Wistar rats (body weight 45-
An iron-free diet (manufactured by Oriental Yeast Co., Ltd.) containing 50 g) as an iron content of 0.25 mg / 100 g was fed for 3 weeks to prepare anemia rats having a blood hemoglobin value of 7 g / 100 ml or less. And 1
The test diets shown below were forcibly orally administered at 1 ml / day for 6 weeks, while the group was made up of 5 animals and the iron-free diet was continued thereafter. Test group 1: Only iron-free diet Test group 2: Ferrous sulfate as iron 0.2 mg / ml Test group 3: Ferrous sulfate as iron 0.2 mg / ml + N-acetylneuraminic acid-linked oligosaccharide 200 mg / ml Test group 4: 0.2 mg / ml of ferrous sulfate as iron + 200 mg / ml of N-acetylneuraminic acid Test group 5: 0.2 mg / ml of ferrous sulfate as iron + 2 of lactose 2
00mg / ml
【００３８】試験飼料投与後６週間目に、尾静脈より採
血し自動血球計測装置（東亜医用電子株式会社）でヘモ
グロビン値を測定した。その結果を表６に示した。Six weeks after the administration of the test feed, blood was collected from the tail vein and the hemoglobin value was measured with an automatic blood cell counter (Toa Medical Electronics Co., Ltd.). The results are shown in Table 6.
【００３９】[0039]
【表６】 [Table 6]
【００４０】このように、本発明のＮ−アセチルノイラ
ミン酸結合オリゴ糖投与群は貧血治療効果を示し、無機
鉄である硫酸第一鉄を単独投与群及びＮ−アセチルノイ
ラミン酸投与群よりも優れた効果を示すことが判った。As described above, the N-acetylneuraminic acid-linked oligosaccharide administration group of the present invention shows an anemia treatment effect, and is superior to the inorganic iron ferrous sulfate alone administration group and the N-acetylneuraminic acid administration group. Was also found to show excellent effects.
【００４１】[0041]
【発明の効果】本発明により、新規なＮ−アセチルノイ
ラミン酸結合オリゴ糖が提供される。本発明のＮ−アセ
チルノイラミン酸結合オリゴ糖は、ミネラルの吸収性を
促進する作用を有するので、このＮ−アセチルノイラミ
ン酸結合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。The present invention provides a novel N-acetylneuraminic acid-linked oligosaccharide. Since the N-acetylneuraminic acid-bonded oligosaccharide of the present invention has the action of promoting the absorbability of minerals, the drug, the food and drink and the feed containing the N-acetylneuraminic acid-bonded oligosaccharide,
Useful for mineral supplementation.
【図１】は、Ｎ−アセチルノイラミン酸結合オリゴ糖の
ＨＰＬＣによる分析結果を示す。FIG. 1 shows the results of HPLC analysis of N-acetylneuraminic acid-linked oligosaccharides.
【図２】は、Ｏ−β−Ｄ−ガラクトピラノシル−（１→
８）−Ｎ−アセチルノイラミン酸の 1Ｈ−ＮＭＲスペク
トルを示す。FIG. 2 shows O-β-D-galactopyranosyl- (1 →
8) 1 H-NMR spectrum of -N-acetylneuraminic acid is shown.
【図３】は、Ｏ−β−Ｄ−ガラクトピラノシル−（１→
８）−Ｎ−アセチルノイラミン酸の13Ｃ−ＮＭＲスペク
トルを示す。FIG. 3 shows O-β-D-galactopyranosyl- (1 →
8) shows the 13 C-NMR spectrum of -N-acetylneuraminic acid.
【図４】は、Ｏ−β−Ｄ−ガラクトピラノシル−（１→
９）−Ｎ−アセチルノイラミン酸の 1Ｈ−ＮＭＲスペク
トルを示す。FIG. 4 shows O-β-D-galactopyranosyl- (1 →
9) 1 H-NMR spectrum of -N-acetylneuraminic acid is shown.
【図５】は、Ｏ−β−Ｄ−ガラクトピラノシル−（１→
９）−Ｎ−アセチルノイラミン酸の13Ｃ−ＮＭＲスペク
トルを示す。FIG. 5 shows O-β-D-galactopyranosyl- (1 →
9) shows the 13 C-NMR spectrum of -N-acetylneuraminic acid.
【図６】は、試験例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. 6 shows the experimental results for the calcium absorption promoting effect of Test Example 1.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｈ 13/04 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical indication C07H 13/04
Claims (6)
されるＮ−アセチルノイラミン酸結合オリゴ糖。（ただ
し、式中、Ｇａｌはガラクトースを、Ｎｅｕ５ＡｃはＮ
−アセチルノイラミン酸をそれぞれ示し、ｎは１〜２の
整数を示す。）1. An N-acetylneuraminic acid-linked oligosaccharide represented by the general formula (Gal) n-Neu5Ac. (However, in the formula, Gal is galactose and Neu5Ac is N.
-Acetylneuraminic acid is shown, and n is an integer of 1-2. )
されるＮ−アセチルノイラミン酸結合オリゴ糖が、Ｏ−
β−Ｄ−ガラクトピラノシル−（１→８）−Ｎ−アセチ
ルノイラミン酸である請求項１記載のオリゴ糖。2. The N-acetylneuraminic acid-linked oligosaccharide represented by the general formula (Gal) n-Neu5Ac is O-
The oligosaccharide according to claim 1, which is β-D-galactopyranosyl- (1 → 8) -N-acetylneuraminic acid.
されるＮ−アセチルノイラミン酸結合オリゴ糖が、Ｏ−
β−Ｄ−ガラクトピラノシル−（１→９）−Ｎ−アセチ
ルノイラミン酸である請求項１記載のオリゴ糖。3. An N-acetylneuraminic acid-linked oligosaccharide represented by the general formula (Gal) n-Neu5Ac is O-
The oligosaccharide according to claim 1, which is β-D-galactopyranosyl- (1 → 9) -N-acetylneuraminic acid.
とし、β−ガラクトシダーゼを作用させて一般式（Ｇａ
ｌ）ｎ−Ｎｅｕ５Ａｃで表されるＮ−アセチルノイラミ
ン酸結合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−Ｎｅｕ５Ａｃで表される
Ｎ−アセチルノイラミン酸結合オリゴ糖の製造法。（た
だし、式中、Ｇａｌはガラクトースを、Ｎｅｕ５Ａｃは
Ｎ−アセチルノイラミン酸をそれぞれ示し、ｎは１〜２
の整数を示す。）4. Lactose and N-acetylneuraminic acid are used as raw materials, and β-galactosidase is allowed to act on them to give a compound of the general formula (Ga
l) N-Acetylneuraminic acid-bonded oligosaccharide represented by n-Neu5Ac is produced and collected, and N-acetylneuraminic acid-bonded represented by the general formula (Gal) n-Neu5Ac is characterized. Method for producing oligosaccharides. (In the formula, Gal represents galactose, Neu5Ac represents N-acetylneuraminic acid, and n represents 1 to 2).
Indicates an integer. )
されるＮ−アセチルノイラミン酸結合オリゴ糖を有効成
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、Ｎｅｕ５ＡｃはＮ−アセチルノイラ
ミン酸をそれぞれ示し、ｎは１〜２の整数を示す。）5. A mineral absorption enhancer comprising an N-acetylneuraminic acid-linked oligosaccharide represented by the general formula (Gal) n-Neu5Ac as an active ingredient. (However, in the formula, Gal
Represents galactose, Neu5Ac represents N-acetylneuraminic acid, and n represents an integer of 1 to 2. )
されるＮ−アセチルノイラミン酸結合オリゴ糖を配合し
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
収性の高い飲食品または飼料。（ただし、式中、Ｇａｌ
はガラクトースを、Ｎｅｕ５ＡｃはＮ−アセチルノイラ
ミン酸をそれぞれ示し、ｎは１〜２の整数を示す。）6. A food or drink or a feed having high mineral absorbability, characterized in that N-acetylneuraminic acid-bound oligosaccharide represented by the general formula (Gal) n-Neu5Ac is blended to enhance mineral absorbability. . (However, in the formula, Gal
Represents galactose, Neu5Ac represents N-acetylneuraminic acid, and n represents an integer of 1 to 2. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6326525A JPH07316177A (en) | 1994-03-31 | 1994-12-28 | New oligosaccharide, production and use thereof |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8570794 | 1994-03-31 | ||
| JP6-85707 | 1994-03-31 | ||
| JP6326525A JPH07316177A (en) | 1994-03-31 | 1994-12-28 | New oligosaccharide, production and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07316177A true JPH07316177A (en) | 1995-12-05 |
Family
ID=26426713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6326525A Pending JPH07316177A (en) | 1994-03-31 | 1994-12-28 | New oligosaccharide, production and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07316177A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09301874A (en) * | 1996-05-16 | 1997-11-25 | Snow Brand Milk Prod Co Ltd | Improving agent for cerebral function |
| CN116098201A (en) * | 2023-04-11 | 2023-05-12 | 黑龙江飞鹤乳业有限公司北京分公司 | Use of nutritional compositions for improving bone density and bone metabolism |
-
1994
- 1994-12-28 JP JP6326525A patent/JPH07316177A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09301874A (en) * | 1996-05-16 | 1997-11-25 | Snow Brand Milk Prod Co Ltd | Improving agent for cerebral function |
| CN116098201A (en) * | 2023-04-11 | 2023-05-12 | 黑龙江飞鹤乳业有限公司北京分公司 | Use of nutritional compositions for improving bone density and bone metabolism |
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