CA1183530A - Polysaccharides having anticarcinogenic activity and method for producing same - Google Patents
Polysaccharides having anticarcinogenic activity and method for producing sameInfo
- Publication number
- CA1183530A CA1183530A CA000397674A CA397674A CA1183530A CA 1183530 A CA1183530 A CA 1183530A CA 000397674 A CA000397674 A CA 000397674A CA 397674 A CA397674 A CA 397674A CA 1183530 A CA1183530 A CA 1183530A
- Authority
- CA
- Canada
- Prior art keywords
- glucan
- beta
- mycelium
- strain
- glu
- 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
Links
- 230000003217 anti-cancerogenic effect Effects 0.000 title abstract description 20
- 150000004676 glycans Chemical class 0.000 title abstract description 20
- 239000005017 polysaccharide Substances 0.000 title abstract description 20
- 229920001282 polysaccharide Polymers 0.000 title abstract description 15
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920001503 Glucan Polymers 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 23
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 22
- 239000000284 extract Substances 0.000 claims abstract description 17
- 239000001963 growth medium Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 241000383860 Pseudoplectania Species 0.000 claims abstract description 4
- 239000008103 glucose Substances 0.000 claims description 8
- 241000383853 Pseudoplectania nigrella Species 0.000 claims 1
- 150000004804 polysaccharides Polymers 0.000 abstract description 5
- 206010028980 Neoplasm Diseases 0.000 description 24
- 239000000126 substance Substances 0.000 description 22
- 238000000605 extraction Methods 0.000 description 11
- 238000009630 liquid culture Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 208000006268 Sarcoma 180 Diseases 0.000 description 8
- 238000002054 transplantation Methods 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000735 allogeneic effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 238000002523 gelfiltration Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004255 ion exchange chromatography Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 201000008808 Fibrosarcoma Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- -1 af~etone Chemical compound 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000221700 Pezizales Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 235000019764 Soybean Meal Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 238000004816 paper chromatography Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004455 soybean meal Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001233887 Ania Species 0.000 description 1
- 238000011725 BALB/c mouse Methods 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 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 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 101150007148 THI5 gene Proteins 0.000 description 1
- 241000051818 Timarcha intricata Species 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012364 cultivation method Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 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
- 239000012454 non-polar solvent Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 108010080511 serum sodium transport inhibitor Proteins 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32797/81 | 1981-03-06 | ||
| JP56032797A JPS57146719A (en) | 1981-03-06 | 1981-03-06 | Preparation of antitumor substance |
| JP139039/81 | 1981-09-03 | ||
| JP13903981A JPS5840301A (ja) | 1981-09-03 | 1981-09-03 | 抗腫瘍活性を有するβ−１，３−グルカン |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1183530A true CA1183530A (en) | 1985-03-05 |
Family
ID=26371382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000397674A Expired CA1183530A (en) | 1981-03-06 | 1982-03-05 | Polysaccharides having anticarcinogenic activity and method for producing same |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4454289A (enExample) |
| KR (1) | KR870001814B1 (enExample) |
| AU (1) | AU549553B2 (enExample) |
| CA (1) | CA1183530A (enExample) |
| CH (1) | CH660026A5 (enExample) |
| DE (1) | DE3208057C2 (enExample) |
| ES (1) | ES8302776A1 (enExample) |
| FR (1) | FR2501232A1 (enExample) |
| GB (1) | GB2094324B (enExample) |
| IT (1) | IT1150622B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023401A (ja) * | 1983-03-09 | 1985-02-06 | Toyo Soda Mfg Co Ltd | 多糖類およびその製造法 |
| 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 |
| FI885955A7 (fi) * | 1987-12-23 | 1989-06-24 | Weston George Ltd | Ny b-1,3-glukanexopolysackarid och foerfarande foer framstaellning av densamma. |
| JP2681653B2 (ja) * | 1988-05-13 | 1997-11-26 | 台糖株式会社 | 抗エイズウィルス剤 |
| US5189028A (en) * | 1989-02-20 | 1993-02-23 | Taito Co., Ltd. | Composition and method to enhance the efficacy of a fish vaccine and to stimulate the immune system of fish |
| GB9007730D0 (en) * | 1990-04-05 | 1990-06-06 | Cerestar Holding Bv | Therapeutic compound and composition |
| CA2081025A1 (en) * | 1991-02-21 | 1992-08-22 | Kazuhiro Inoue | Carboxymethylmannoglucans and derivatives thereof |
| JP3167649B2 (ja) * | 1997-07-25 | 2001-05-21 | 株式会社資生堂 | タンパク質を除去したβ−１，３グルカン及びこれを主成分とするゲルからなる超音波診断装置のプローブ用接触媒体 |
| US6251877B1 (en) * | 1998-03-24 | 2001-06-26 | Pacific Corporation | Composition for external application containing a β-1,6-branched-β-1,3-glucan |
| US7507724B2 (en) | 2001-01-16 | 2009-03-24 | Sloan-Kettering Institute For Cancer Research | Therapy-enhancing glucan |
| EP1357919B1 (en) * | 2001-01-16 | 2017-04-05 | Sloan-Kettering Institute For Cancer Research | Therapy-enhancing glucan |
| US7906492B2 (en) * | 2001-01-16 | 2011-03-15 | Sloan-Kettering Institute For Cancer Research | Therapy-enhancing glucan |
| NO20014256D0 (no) | 2001-09-03 | 2001-09-03 | Bjoern Kristiansen | Fremstilling av immunstimulerende forbindelse |
| US7514085B2 (en) * | 2004-07-16 | 2009-04-07 | Medimush A/S | Immune modulating compounds from fungi |
| MX2007014219A (es) * | 2005-05-13 | 2008-04-08 | Medimush As | Productos alimenticios o forrajeros que comprenden material fungico. |
| US9072776B2 (en) * | 2005-06-15 | 2015-07-07 | Glycanova As | Anti-cancer combination treatment and kit-of-parts |
| US20090005340A1 (en) * | 2005-06-15 | 2009-01-01 | Medimush A/S | Bioactive Agents Produced By Submerged Cultivation of a Basidiomycete Cell |
| US8323644B2 (en) * | 2006-01-17 | 2012-12-04 | Sloan-Kettering Institute For Cancer Research | Therapy-enhancing glucan |
| US20090053221A1 (en) * | 2006-01-17 | 2009-02-26 | Cheung Nai-Kong V | Immune response enhancing glucan |
| US8075839B2 (en) | 2006-09-15 | 2011-12-13 | Haynes International, Inc. | Cobalt-chromium-iron-nickel alloys amenable to nitride strengthening |
| DE102015224162B4 (de) * | 2015-12-03 | 2017-11-30 | Siemens Healthcare Gmbh | Verfahren zur Ermittlung einer eine Bewegung in einem zumindest teilweise bewegten Untersuchungsbereich beschreibenden Bewegungsinformation und Magnetresonanzeinrichtung |
| CN112076209A (zh) * | 2019-06-14 | 2020-12-15 | 青岛海洋生物医药研究院股份有限公司 | 一种β-葡聚糖组合物及其用途 |
| CN111593034B (zh) * | 2020-06-24 | 2022-07-05 | 江南大学 | 利用β-1,6-葡聚糖酶制备低聚龙胆糖的方法及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3301848A (en) * | 1962-10-30 | 1967-01-31 | Pillsbury Co | Polysaccharides and methods for production thereof |
| JPS5339519B1 (enExample) * | 1970-07-31 | 1978-10-21 | ||
| JPS5461112A (en) * | 1977-10-24 | 1979-05-17 | Ono Pharmaceut Co Ltd | Oncostatic polysaccharide* its preparation* and oncostatic drugs containing it as an effective component |
-
1982
- 1982-02-23 US US06/351,364 patent/US4454289A/en not_active Expired - Lifetime
- 1982-03-01 GB GB8205928A patent/GB2094324B/en not_active Expired
- 1982-03-05 ES ES510184A patent/ES8302776A1/es not_active Expired
- 1982-03-05 AU AU81148/82A patent/AU549553B2/en not_active Ceased
- 1982-03-05 KR KR8200949A patent/KR870001814B1/ko not_active Expired
- 1982-03-05 CA CA000397674A patent/CA1183530A/en not_active Expired
- 1982-03-05 IT IT19987/82A patent/IT1150622B/it active
- 1982-03-05 FR FR8203720A patent/FR2501232A1/fr active Granted
- 1982-03-05 DE DE3208057A patent/DE3208057C2/de not_active Expired
- 1982-03-05 CH CH1376/82A patent/CH660026A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3208057A1 (de) | 1982-09-16 |
| GB2094324B (en) | 1984-09-19 |
| GB2094324A (en) | 1982-09-15 |
| DE3208057C2 (de) | 1987-02-19 |
| AU549553B2 (en) | 1986-01-30 |
| KR870001814B1 (ko) | 1987-10-13 |
| AU8114882A (en) | 1982-09-09 |
| US4454289A (en) | 1984-06-12 |
| CH660026A5 (de) | 1987-03-13 |
| ES510184A0 (es) | 1983-01-16 |
| ES8302776A1 (es) | 1983-01-16 |
| KR830009224A (ko) | 1983-12-19 |
| FR2501232A1 (fr) | 1982-09-10 |
| FR2501232B1 (enExample) | 1985-03-15 |
| IT8219987A0 (it) | 1982-03-05 |
| IT1150622B (it) | 1986-12-17 |
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