JPH026761B2 - - Google Patents
Info
- Publication number
- JPH026761B2 JPH026761B2 JP57157058A JP15705882A JPH026761B2 JP H026761 B2 JPH026761 B2 JP H026761B2 JP 57157058 A JP57157058 A JP 57157058A JP 15705882 A JP15705882 A JP 15705882A JP H026761 B2 JPH026761 B2 JP H026761B2
- Authority
- JP
- Japan
- Prior art keywords
- methylglucose
- polysaccharide
- tri
- repeating unit
- repeating units
- 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.)
- Expired - Lifetime
Links
- 150000004676 glycans Chemical class 0.000 claims description 59
- 229920001282 polysaccharide Polymers 0.000 claims description 59
- 239000005017 polysaccharide Substances 0.000 claims description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000000605 extraction Methods 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- LMWNQPUYOLOJQP-UTINFBMNSA-N (2r,3s,4r,5r)-5-hydroxy-2,3,4,6-tetramethoxyhexanal Chemical compound COC[C@@H](O)[C@@H](OC)[C@H](OC)[C@@H](OC)C=O LMWNQPUYOLOJQP-UTINFBMNSA-N 0.000 claims description 8
- LMWNQPUYOLOJQP-UHFFFAOYSA-N 2,3,4,6-Me4-Glc Natural products COCC(O)C(OC)C(OC)C(OC)C=O LMWNQPUYOLOJQP-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012670 alkaline solution Substances 0.000 claims description 7
- 238000004458 analytical method Methods 0.000 claims description 7
- LMHKDVPFDHNVFB-BZNPZCIMSA-N (2r,3s,4r,5r)-3,5-dihydroxy-2,4,6-trimethoxyhexanal Chemical compound COC[C@@H](O)[C@@H](OC)[C@H](O)[C@@H](OC)C=O LMHKDVPFDHNVFB-BZNPZCIMSA-N 0.000 claims description 6
- UTLUVTKMAWSZKV-UHFFFAOYSA-N 5-amino-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione Natural products COCC1OC(O)C(OC)C(O)C1OC UTLUVTKMAWSZKV-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- UITMJPZVJJKFBV-ULAWRXDQSA-N (2r,3s,4r,5r)-3,5,6-trihydroxy-2,4-dimethoxyhexanal Chemical compound CO[C@@H](C=O)[C@@H](O)[C@H](OC)[C@H](O)CO UITMJPZVJJKFBV-ULAWRXDQSA-N 0.000 claims description 5
- LOODZAPIPITKBN-BZNPZCIMSA-N (2r,3s,4r,5r)-5,6-dihydroxy-2,3,4-trimethoxyhexanal Chemical compound CO[C@@H](C=O)[C@@H](OC)[C@H](OC)[C@H](O)CO LOODZAPIPITKBN-BZNPZCIMSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 230000011987 methylation Effects 0.000 claims description 4
- 238000007069 methylation reaction Methods 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000005640 glucopyranosyl group Chemical group 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- QRAXLHLYZJCAKB-XZBKPIIZSA-N (2r,3s,4r,5r)-3,4,5,6-tetrahydroxy-2-methoxyhexanal Chemical compound CO[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO QRAXLHLYZJCAKB-XZBKPIIZSA-N 0.000 claims 1
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 6
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 241000221198 Basidiomycota Species 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229920002498 Beta-glucan Polymers 0.000 description 4
- 101000763602 Manilkara zapota Thaumatin-like protein 1 Proteins 0.000 description 4
- 101000763586 Manilkara zapota Thaumatin-like protein 1a Proteins 0.000 description 4
- 101000966653 Musa acuminata Glucan endo-1,3-beta-glucosidase Proteins 0.000 description 4
- 229920002305 Schizophyllan Polymers 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- AYRXSINWFIIFAE-UHFFFAOYSA-N O6-alpha-D-Galactopyranosyl-D-galactose Natural products OCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O AYRXSINWFIIFAE-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- -1 alditol acetate Chemical class 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- DLRVVLDZNNYCBX-CQUJWQHSSA-N gentiobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-CQUJWQHSSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229920001503 Glucan Polymers 0.000 description 2
- 241000893212 Pestalotia Species 0.000 description 2
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001507667 Volvariella Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003308 immunostimulating effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 235000000023 Auricularia auricula Nutrition 0.000 description 1
- 240000005710 Auricularia polytricha Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 229920001491 Lentinan Polymers 0.000 description 1
- 240000000599 Lentinula edodes Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 230000003627 anti-cholesterol Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000385 dialysis solution Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010571 fourier transform-infrared absorption spectrum Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 210000004013 groin Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940115286 lentinan Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57157058A JPS5945301A (ja) | 1982-09-09 | 1982-09-09 | 多糖類及びその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57157058A JPS5945301A (ja) | 1982-09-09 | 1982-09-09 | 多糖類及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5945301A JPS5945301A (ja) | 1984-03-14 |
| JPH026761B2 true JPH026761B2 (fr) | 1990-02-13 |
Family
ID=15641286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57157058A Granted JPS5945301A (ja) | 1982-09-09 | 1982-09-09 | 多糖類及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5945301A (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0692441B2 (ja) * | 1986-03-03 | 1994-11-16 | 株式会社林原生物化学研究所 | β−Ｄ−グルカンとその製造方法及び用途 |
| US5811542A (en) * | 1989-09-08 | 1998-09-22 | Alpha-Beta Technology, Inc. | Method for producing soluble glucans |
| US5622939A (en) * | 1992-08-21 | 1997-04-22 | Alpha-Beta Technology, Inc. | Glucan preparation |
| WO1991003495A1 (fr) * | 1989-09-08 | 1991-03-21 | Alpha Beta Technology, Inc. | Procede de production de glucans solubles |
| US5488040A (en) * | 1989-09-08 | 1996-01-30 | Alpha-Beta Technology, Inc. | Use of neutral soluble glucan preparations to stimulate platelet production |
| JPH05502018A (ja) * | 1989-09-08 | 1993-04-15 | アルファ ベータ テクノロジー，インコーポレイティッド | 免疫系活性化方法 |
| US5622940A (en) * | 1994-07-14 | 1997-04-22 | Alpha-Beta Technology | Inhibition of infection-stimulated oral tissue destruction by β(1,3)-glucan |
| US6046323A (en) * | 1997-07-29 | 2000-04-04 | The Collaborative Group, Ltd. | Conformations of PPG-glucan |
| AU6261999A (en) | 1998-09-25 | 2000-04-17 | Collaborative Group, Ltd., The | Very high molecular weight beta-glucans |
| US6369216B1 (en) | 1998-09-25 | 2002-04-09 | Biopolymer Engineering Pharmaceutical, Inc. | Very high molecular weight β-glucans |
| JP4812157B2 (ja) * | 2000-05-16 | 2011-11-09 | 株式会社Ａｄｅｋａ | 免疫増強作用を有する低分子化βグルカンを含有する医薬品素材 |
-
1982
- 1982-09-09 JP JP57157058A patent/JPS5945301A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5945301A (ja) | 1984-03-14 |
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