CS270103B1 - Wall (1,6)-beta-d-gluco-(1,3)-beta-d-glucan of yeast - Google Patents
Wall (1,6)-beta-d-gluco-(1,3)-beta-d-glucan of yeast Download PDFInfo
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- CS270103B1 CS270103B1 CS863944A CS394486A CS270103B1 CS 270103 B1 CS270103 B1 CS 270103B1 CS 863944 A CS863944 A CS 863944A CS 394486 A CS394486 A CS 394486A CS 270103 B1 CS270103 B1 CS 270103B1
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- beta
- glucan
- wall
- gluco
- yeast
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- 240000004808 Saccharomyces cerevisiae Species 0.000 title claims abstract description 8
- 229920002498 Beta-glucan Polymers 0.000 title abstract description 7
- 125000005640 glucopyranosyl group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002671 adjuvant Substances 0.000 abstract description 2
- 238000002329 infrared spectrum Methods 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 3
- 230000008076 immune mechanism Effects 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229940124856 vaccine component Drugs 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000013049 sediment Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 230000000242 pagocytic effect Effects 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 210000003024 peritoneal macrophage Anatomy 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000616862 Belliella Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 230000007813 immunodeficiency Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 108700005457 microfibrillar Proteins 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000004223 radioprotective effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
stěnový /l«*6/-beta-D-glukó- (l-»-3/-beta-D-glukén kvasiniek a /06/20 + 5,0 až 8,8 0 /c«0,50 v DMSO/ molekulové hmotnosl 4xl05 až 2x10®, obaah dusíka o až 0,2 % hmot. stanovený podlá Dumasa/, obsah popola 0,3 až 0,6 % hmot., Ič-spektrum v KBr 892, 1045, 1080, 1160, 1205, 1252, 1315, 1375, 1640, 2922, 3434 CID“1, 13CNMR spektrum v DMSO-dfi so signálom 86,21 ppm. Ůčelom rieSenia je stěnový /l-*6/- -beta-D-gluko-/l-»3/-beta-D-glukán s biologicky účinnou Struktúrou, chemicky a fyzikálno chemicky definovaný, ktorý má použitie ako adjuvantná zložka vakcin a ako základna látka pre přípravu vo voda rozpustných stimulátorov nespecifických imunitných mechanizmov.wall / l «* 6 / -beta-D-glucose (1 -? - 3 / -beta-D-glucan yeast a / 06/20 + 5.0 to 8.8 0 / c «0.50 in DMSO / molecular weight 4x10 5 up to 2x10®, nitrogen up to 0.2% wt. set by Dumasa /, an ash content of 0.3 to 0.6% by weight, IR spectrum in KBr 892, 1045, 1080, 1160, 1205, 1252, 1315, 1375, 1640, 2922, 3434 CID "1, 13 CNMR spectrum in DMSO-d1 with a signal of 86.21 ppm. The purpose of the solution is wall / l- * 6 / - -beta-D-gluco- [1- [3] -beta-D-glucan with a biologically active structure chemically and physically chemically defined, which has use as adjuvant vaccine component and as a base substance for the preparation of water-soluble stimulators non-specific immune mechanisms.
Description
Vynález ea týká stěnového /l-*6/-beta-D-gluko-/l-»3/-beta-D-glukánu kvasiniek.The invention relates to a yeast wall (1-) 6 -beta-D-gluco- [1- (3H) -beta-D-glucan.
Stěnové /l->6/-beta-D-gluko-/l-»»3/-beta-D-glukány tvoria skeletálnu mikrofibrilárnu část buňkových stien húb. Sú nerozpustné v organických rozpúétadlách, voda a v zriedených alkáliách, z farmakologického hlediska aú to látky netoxické, ktoré nešpecificky zvyšujú rezistenciu hostitele, voči r8znym chorobným procesom najma bakteriálnym, virusovým a hubovým infekciám, imunodeficientným atavom a neoplastickým procesorom. 3avla výrazný rádioprotektívny efekt a poeobia ako adjuvanty pri imunizácii a výrobě vakcín /G. Chihara, Y. Y. Maeda, 0. Hamuro, int. 3. Tise, Reac., 4, 207, 1982: N. R. Diluzio, Trends Pharm. Sel., 4, 344, 1983/.Wall [1-> 6] -beta-D-gluco- [1-> β-beta-D-glucans form the skeletal microfibrillar part of the cell walls of fungi. They are insoluble in organic solvents, water and dilute alkalis, from a pharmacological point of view and are non-toxic substances which non-specifically increase the resistance of the host to various disease processes, in particular bacterial, viral and fungal infections, immunodeficiency and neoplastic processors. 3avla significant radioprotective effect and poeobia as adjuvants in immunization and vaccine production / G. Chihara, Y. Y. Maeda, 0. Hamuro, int. 3. Tise, Reac., 4, 207, 1982: N. R. Diluzio, Trends Pharm. Sel., 4, 344, 1983 /.
Podstatou vynálezu je stěnový /l->6/-beta-D-gluko-/l->3/-beta-D-glukán kvasiniek s biologicky účinnou Struktúrou obecného vzorce beta-D-GlcpThe subject of the invention is a wall (1-> 6) -beta-D-gluco- (1-> 3) -beta-D-glucan of yeast with a biologically active structure of the general formula beta-D-Glcp
A-*3/-beta-D-Glcp/ /l-»3/-beta-D-Glcp)^7jQA- * 3 / -beta-D-Glcp / / l- »3 / -beta-D-Glcp) ^ 7jQ
220-1100 kde Glcp je glukopyrenozylová jednotka.220-1100 where Glcp is a glucopyrenosyl unit.
Stěnový /i-»6/-beta-D-gluko-/l~*3/-beta-D-glukán kvasiniek sa získá frakcionáciou buňkových stíén postupem podlá 0. 0. Bella a 0. H. Northcota, 3. chem. Soc. 1950, 1944 a jeho modifikáclami A. L.Houwink, 0. R. Kreger, Antonie van Leeuwenhoek 19, 1, 1953) S. Peat, W. 3. Whelan, T. E. Edwards, 3. Chem. Soc. 1958, 3862) 3. S. D. Bacon, W. C. Farmer, D. 3ones, 3. F. T. Taylor, Biochem. 3. 114, 557, 1969) D. 3. Manners, A. 3. Masson, 3. C. Patterson, 3. Gen. Microbiol. 80, 411, 1974) 3. Jelsma, D. R. Kreger, carbohyd. Res. 43, 200, 1975.Yeast wall (i-> 6) -beta-D-gluco- (1 * 3) -beta-D-glucan is obtained by fractionating cell shadows according to the procedure of 0. Bella and 0. H. Northcota, 3. chem. Soc. 1950, 1944 and its modifications A. L. Howink, 0. R. Kreger, Antonie van Leeuwenhoek 19, 1, 1953) S. Peat, W. 3. Whelan, T. E. Edwards, 3. Chem. Soc. 1958, 3862) 3. S. D. Bacon, W. C. Farmer, D. 3ones, 3. F. T. Taylor, Biochem. 3. 114, 557, 1969) D. 3. Manners, A. 3. Masson, 3. C. Patterson, 3. Gen. Microbiol. 80, 411, 1974) 3. Jelsma, D. R. Kreger, carbohyd. Res. 43, 200, 1975.
Příklad 1Example 1
100 g pekárenského droždla Saccharomyces cerevisiae sa suspenduje v 150 ml 6 % hmot, hydroxidu sodného a pri 60 °C sa mleša 4 h. suspenzia sa zriedi 100 ml 60 °C teplej vody a odstředí, sediment sa suspenduje v 150 ml 3 % hmot, hydroxidu sodného, mieša pri 80 až 100 °C 2 h a odstředí, sediment sa třikrát premyje vodou a extrahuje třikrát 20 ml 4 % hmot, kyselinou chlorovodíkovou alebo kyselinou fosforečnou za miešania pri teplote mieatnosti 2 h a odstředí, sediment sa premýva vodou dovtedy až supernatant je číry a reaguje neutrálně. Výtažok 4,5 až 5,4 % hmot, počítané na suéinu kvasiniek. Mol. hmotnost: 4 x 10S až 2 x 1O6. Glukán neobsahuje dusík a obsah popola je 0,5 % hmot. Infračervené spektrum: 892, 1045, 1080, 1160, 1205, 1252, 1315, 1375, 1640, 2922, 3434 cm1.100 g of baker's yeast Saccharomyces cerevisiae are suspended in 150 ml of 6% by weight sodium hydroxide and stirred at 60 ° C for 4 hours. The suspension is diluted with 100 ml of 60 ° C warm water and centrifuged, the sediment is suspended in 150 ml of 3% by weight. sodium hydroxide, stirred at 80-100 ° C for 2 h and centrifuged, the sediment was washed three times with water and extracted three times with 20 ml of 4% w / w, hydrochloric acid or phosphoric acid with stirring at room temperature for 2 h and centrifuged, the sediment was washed with water until the supernatant was clear and reacts neutrally. Yield 4.5 to 5.4% by weight, based on the yeast dry matter. Moth. weight: 4 x 10 S to 2 x 10 6 . Glucan does not contain nitrogen and the ash content is 0.5% by weight. Infrared Spectrum: 892, 1045, 1080, 1160, 1205, 1252, 1315, 1375, 1640, 2922, 3434 cm -1 .
Modifikovaný spdsob příkladu 1 s použitím org* kyselin a enzýmov sa uskutočni podlá známého’postupu D. 3. Manners, A. 3. Masson, 3. C. Patterson, Biochem. 3. 135, 19, 1973. .The modified method of Example 1 using org * acids and enzymes was performed according to the known procedure D. 3. Manners, A. 3. Masson, 3. C. Patterson, Biochem. 3. 135, 19, 1973.
příklad 2 ' .Example 2 '.
Perítoneálne makrofágy kontrolných morčiat /namieato stenového/l->6/-beta-D-gluko-/l-*3/-beta-D-glukánu dostali fyziologický roztok/ malí stupeň metabolickej aktivity 8,1 femtomSlov redukovaného formazánu, fagocitárnu aktivitu 64,8 % a za hodinu bolí schopné usmrtit 35,9 % přítomných patogénnych kandíd. Naproti tomu perítoneálne makrofágy morčiat, ktoré dostali 3 dávky stěnového /l->6/-beta-D-gluko-/l-*>3/-beta-D-glukánu v dňoch 12, 7, 3 dni před odberom makrofágov v množatve 10 mg/kg žívej váhy,Peritoneal macrophages of control guinea pigs (wall> /> 6) -beta-D-gluco- (1- * 3) -beta-D-glucan received saline / low metabolic activity 8.1 femtomSlov reduced formazan, phagocytic activity 64 .8% and per hour were able to kill 35.9% of the pathogenic candidates present. In contrast, peritoneal macrophages of guinea pigs that received 3 doses of wall / l-> 6 / -beta-D-gluco- / 1 - *> 3 / -beta-D-glucan on days 12, 7, 3 days before collection of macrophages in the amount 10 mg / kg body weight,
CS 270103 Bl tieto makrofágy mail stupeň metabolickej aktivity stimulovaný na 13,5 fentomólu redukovaného formazánu, rovnako bola zvýšená fagocitárna aktivita priemerne na 72,9 % a schopnost usmrcovat patogénne kandidy na 58,2CS 270103 B1 these macrophages mail the degree of metabolic activity stimulated to 13.5 phentomole of reduced formazan, as well as increased phagocytic activity increased on average to 72.9% and the ability to kill pathogenic candidiasis to 58.2
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863944A CS270103B1 (en) | 1986-05-29 | 1986-05-29 | Wall (1,6)-beta-d-gluco-(1,3)-beta-d-glucan of yeast |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863944A CS270103B1 (en) | 1986-05-29 | 1986-05-29 | Wall (1,6)-beta-d-gluco-(1,3)-beta-d-glucan of yeast |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS394486A1 CS394486A1 (en) | 1989-11-14 |
| CS270103B1 true CS270103B1 (en) | 1990-06-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS863944A CS270103B1 (en) | 1986-05-29 | 1986-05-29 | Wall (1,6)-beta-d-gluco-(1,3)-beta-d-glucan of yeast |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS270103B1 (en) |
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1986
- 1986-05-29 CS CS863944A patent/CS270103B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS394486A1 (en) | 1989-11-14 |
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