NO126529B - - Google Patents
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- Publication number
- NO126529B NO126529B NO2702/70A NO270270A NO126529B NO 126529 B NO126529 B NO 126529B NO 2702/70 A NO2702/70 A NO 2702/70A NO 270270 A NO270270 A NO 270270A NO 126529 B NO126529 B NO 126529B
- Authority
- NO
- Norway
- Prior art keywords
- glucosides
- solutions
- glucoside
- podophyllotoxin
- solution
- Prior art date
Links
- 229930182478 glucoside Natural products 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 241001495452 Podophyllum Species 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- -1 podophyllum glucosides Chemical class 0.000 claims description 3
- 239000007853 buffer solution Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 230000011278 mitosis Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000008131 glucosides Chemical class 0.000 description 13
- 239000008103 glucose Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- NXVJTGLCCSFGAT-QNDDJFOYSA-N (5r,5ar,8ar,9r)-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NXVJTGLCCSFGAT-QNDDJFOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920001864 tannin Polymers 0.000 description 3
- 239000001648 tannin Substances 0.000 description 3
- 235000018553 tannin Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DRWJHJXCAJKBBG-UHFFFAOYSA-L C(C(O)C(O)C(=O)O)(=O)O.P(=O)([O-])([O-])O.[Na+].[Na+] Chemical compound C(C(O)C(O)C(=O)O)(=O)O.P(=O)([O-])([O-])O.[Na+].[Na+] DRWJHJXCAJKBBG-UHFFFAOYSA-L 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000221860 Podophyllum emodi Species 0.000 description 1
- 235000010169 Podophyllum emodi Nutrition 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- CBMPTFJVXNIWHP-UHFFFAOYSA-L disodium;hydrogen phosphate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].OP([O-])([O-])=O.OC(=O)CC(O)(C(O)=O)CC(O)=O CBMPTFJVXNIWHP-UHFFFAOYSA-L 0.000 description 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
- 229960001237 podophyllotoxin Drugs 0.000 description 1
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- AKYUZBFQLWFNOB-UHFFFAOYSA-K trisodium 2-hydroxypropane-1,2,3-tricarboxylate hydrochloride Chemical compound [Na+].[Na+].[Na+].Cl.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O AKYUZBFQLWFNOB-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Fremgangsmåte for fremstilling av holdbare vannholdige oppløsninger av podofyllumglukosider. Process for the preparation of stable aqueous solutions of podophyllum glucosides.
Det har vist seg at det kan fremstilles holdbare, vannholdige oppløsninger av de It has been shown that durable, aqueous solutions can be produced from them
fri mitose-hemmende podofyllumglukosider med formelen free mitosis-inhibiting podophyllum glucosides with the formula
ved at oppløsninger av glukosidene ved til-setting av pufferoppløsninger innstilles på den pH-verdi som er den optimale for hold-barheten av glukosidene. in that solutions of the glucosides are adjusted to the pH value that is optimal for the durability of the glucosides by adding buffer solutions.
Risomene av forskjellige podofyllum-arter inneholder glukosider sammen med garvestoffer. Disse glukosider kan oppnås i ren tilstand, fri for garvestoffer ved at de tørkede risomer som er befridd for har-piksfraksjonen ved hjelp av kloroform ek-straheres med en lavere alifatisk alkohol, at garvestoffene i ekstrakten felles f. eks. ved behandling med blysalter og glukosidene oppnås fra oppløsningen ved inn-damping og renses og skilles fra hverandre ved fordeling mellom to oppløsningsmidler eller blandinger av oppløsningsmidler som ikke lar seg blande med hverandre, eller ved kromatografi Således ble det av Podo-fyllum emodi Wall oppnådd podofyllotoksin-p-D-glukosid (formel I med R, = CH..S, R2 = H,R,, = O-glukose) og 4'-demetyi-podofyllotoksin-|3-D-glukosid (formel I med R, = R2 = H,R,, = O-glukose), mens Po-dophyllum peltatum L foruten de nevnte glukosider også gav a-peltatin-fj-D-glukosid (formel I med R, = H, R., == O-glukose, R,, = H) og [3-peltatin-(3-D-gliikosid (formel I med R, = CH,,, R2 = O-glukose, R;.. = H). Disse fire naturlige glukosider utmerker seg ved sterk antimitotisk virk-ning ved liten toksitet og kan anvendes terapeutisk ved visse tumorer. Fremstillingen av passende påførings-former for disse glukosider, spesielt steri-liserbare oppløsninger for parenteral ap-plikasjon byr på store vanskeligheter på grunn av den overordentlig store ømfint- The rhizomes of various podophyllum species contain glucosides together with tannins. These glucosides can be obtained in a pure state, free of tannins, by extracting the dried rice that has been freed from the resin fraction using chloroform with a lower aliphatic alcohol, that the tannins in the extract combine e.g. by treatment with lead salts and the glucosides are obtained from the solution by evaporation and purified and separated from each other by partitioning between two solvents or mixtures of solvents that do not allow mixing with each other, or by chromatography Thus podophyllotoxin was obtained from Podophyllum emodi Wall -p-D-glucoside (formula I with R, = CH..S, R2 = H,R,, = O-glucose) and 4'-demethyl-podophyllotoxin-|3-D-glucoside (formula I with R, = R2 = H,R,, = O-glucose), while Po-dophyllum peltatum L, in addition to the mentioned glucosides, also gave a-peltatin-fj-D-glucoside (formula I with R, = H, R., == O-glucose , R,, = H) and [3-peltatin-(3-D-glycoside (formula I with R, = CH,,, R2 = O-glucose, R;.. = H). These four natural glucosides are distinguished by strong antimitotic effect with little toxicity and can be used therapeutically in certain tumors. The production of suitable application forms for these glucosides, especially sterilizable solutions for parenteral application, presents great difficulties ether due to the extremely large delicate
lighet disse stoffer har i vannholdig miljø. similarity these substances have in an aqueous environment.
I det alkaliske område (pH > 7,0) åpner In the alkaline range (pH > 7.0) opens
laktonringen seg, i det svakt sure område the lactone ring itself, in the slightly acidic region
omlagrer de naturlige glukosider seg irre-versibelt i de tungt oppløselige og uvirk-somme pikroderivater. Disse er karaktéri-sert ved at laktonringen i dem er cis-stil^the natural glucosides are irreversibly re-stored in the poorly soluble and inactive picroderivatives. These are characterized by the fact that the lactone ring in them is cis-style^
let sammenknyttet med cykloheksenringén, readily linked to the cyclohexene ring,
mens de naturlige glukosider har trans-sammenknytninger av disse molekyldeler while the natural glucosides have trans linkages of these molecular parts
slik som det fremgår av formelen. I det as appears from the formula. In that
sterkt sure område begynner den hydro-lytiske spalting av glukosidene i glukose strongly acidic region, the hydrolytic cleavage of the glucosides into glucose begins
og i det tungt oppløselige og sterkt toksiske and in the poorly soluble and highly toxic
aglukoner. Det har nu overraskende vist aglucones. It has now surprisingly shown
seg at det foreligger et forholdsvis smalt that there is a relatively narrow
pH-område hvor de naturlige glukosider er pH range where the natural glucosides are
så stabile i vandig miljø at oppløsningene so stable in an aqueous environment that the solutions
praktisk talt ikke forandrer seg ved opp-bevaring og endog kan steriliseres ved oppvarming uten påviselig skade, hvilket byr practically does not change during storage and can even be sterilized by heating without detectable damage, which offers
på spesielle fordeler da disse forholdsvis on special benefits then these comparatively
høyt konsentrerte glukosidoppløsninger highly concentrated glucose solutions
bare meget vanskelig lar seg filtrere sterilt. can only be sterile filtered with great difficulty.
Dette pH-område ligger ikke på samme This pH range is not the same
verdi for de forskjellige glukosider. For podofyllotoksin-p-D-glukosid ligger det f. eks. value for the different glucosides. For podophyllotoxin-p-D-glucoside, there is e.g.
på 3,0 ± 1,0. For den praktiske utførelse av of 3.0 ± 1.0. For the practical execution of
fremgangsmåten er det f. eks. mulig å gå the procedure is, e.g. possible to go
frem slik at oppløsningen av podofyllotoksin-p-D-glukosid i en alifatisk alkohol som forward so that the solution of podophyllotoxin-p-D-glucoside in an aliphatic alcohol which
lar seg blande med vann innstilles på en can be mixed with water set to one
pH-verdi på 3,0 ± 1,0 ved tilsetning av en pH value of 3.0 ± 1.0 when adding a
vandig pufferoppløsning. Denne oppløsning aqueous buffer solution. This resolution
blir fylt over i ampuller og sterilisert ved is filled into ampoules and sterilized with wood
oppvarming. heating.
De oppløsninger som er fremstillet i The solutions prepared in
henhold til oppfinnelsen skal anvendes i according to the invention must be used in
terapien. De følgende eksempler skal for-klare fremgangsmåten nærmere. the therapy. The following examples will explain the procedure in more detail.
Eksempel 1: Example 1:
100 g podofyllotoksin-p-D-glukosid ble 100 g of podophyllotoxin-β-D-glucoside were
oppløst i 100 g 96 pst. etanol og 100 g glyserin og oppløsningen fyllt opp til 2000 cm;! med( 1/30-molar dinatriumfosfat-ci-tronsyre-puffer med pH = 3,0 pH-verdien for den ferdige oppløsning var 3,2. Oppløs-ningen ble fyllt over i ampuller på 2 ems dissolved in 100 g 96 per cent ethanol and 100 g glycerin and the solution filled up to 2000 cm;! with (1/30-molar disodium phosphate-citric acid buffer with pH = 3.0 The pH value of the finished solution was 3.2. The solution was filled into ampoules of 2 ems
som ble sterilisert på kjent måte ved oppvarming. which was sterilized in a known manner by heating.
Eksempel 2: Example 2:
50 g podofyllotoksin-p-D-glukosid ble oppløst i 50 g 96 pst. etanol og oppløsnin-gen fyllt opp til 2000 ems med 1/20- molar dinatriumfosfatvinsyre-puffer med pH = 3,5. pH-verdien for den ferdige oppløsning var 3,6. Den ble bearbeidet videre slik som i Eksempel I. 50 g of podophyllotoxin β-D-glucoside were dissolved in 50 g of 96% ethanol and the solution filled up to 2000 ems with 1/20 molar disodium phosphate tartaric acid buffer with pH = 3.5. The pH value of the finished solution was 3.6. It was processed further as in Example I.
Eksempel 3: Example 3:
100 g podofyllotoksin-p-D-glukosid ble oppløst i 50 g propanol og 50 g glyserin og oppløsningen fyllt opp til 2000 ems med 1/40-molar saltsyre-natriumcitrat-puffer med pH = 2,5. pH-verdien for den ferdige oppløsning var 2,6. Den ble bearbeidet videre slik som angitt i Eksempel 1. 100 g podophyllotoxin β-D-glucoside was dissolved in 50 g propanol and 50 g glycerin and the solution filled up to 2000 ems with 1/40-molar hydrochloric acid-sodium citrate buffer with pH = 2.5. The pH value of the finished solution was 2.6. It was processed further as indicated in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691934902 DE1934902C (en) | 1969-07-10 | Stabilized molding compounds made from polyolefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126529B true NO126529B (en) | 1973-02-19 |
Family
ID=5739352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2702/70A NO126529B (en) | 1969-07-10 | 1970-07-09 |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4928658B1 (en) |
| AT (1) | AT301172B (en) |
| BE (1) | BE753285A (en) |
| CH (1) | CH536862A (en) |
| CS (1) | CS163217B2 (en) |
| DK (1) | DK126506B (en) |
| ES (1) | ES381570A1 (en) |
| FI (1) | FI49623C (en) |
| FR (1) | FR2051671B1 (en) |
| GB (1) | GB1281956A (en) |
| NL (1) | NL161484C (en) |
| NO (1) | NO126529B (en) |
| SE (1) | SE355370B (en) |
| ZA (1) | ZA704657B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8262976B2 (en) | 2004-10-07 | 2012-09-11 | Biomet Manufacturing Corp. | Solid state deformation processing of crosslinked high molecular weight polymeric materials |
| US7462318B2 (en) | 2004-10-07 | 2008-12-09 | Biomet Manufacturing Corp. | Crosslinked polymeric material with enhanced strength and process for manufacturing |
| US7344672B2 (en) | 2004-10-07 | 2008-03-18 | Biomet Manufacturing Corp. | Solid state deformation processing of crosslinked high molecular weight polymeric materials |
| US8641959B2 (en) | 2007-07-27 | 2014-02-04 | Biomet Manufacturing, Llc | Antioxidant doping of crosslinked polymers to form non-eluting bearing components |
| US9586370B2 (en) | 2013-08-15 | 2017-03-07 | Biomet Manufacturing, Llc | Method for making ultra high molecular weight polyethylene |
| CN115819238A (en) * | 2020-03-26 | 2023-03-21 | 优禘股份有限公司 | Low-migration hindered phenol antioxidant compound, preparation method and composition |
-
1970
- 1970-07-03 NL NL7009880.A patent/NL161484C/en not_active IP Right Cessation
- 1970-07-06 ZA ZA704657A patent/ZA704657B/en unknown
- 1970-07-08 FI FI701931A patent/FI49623C/en active
- 1970-07-08 CH CH1034670A patent/CH536862A/en not_active IP Right Cessation
- 1970-07-08 ES ES381570A patent/ES381570A1/en not_active Expired
- 1970-07-09 SE SE09545/70A patent/SE355370B/xx unknown
- 1970-07-09 DK DK359770AA patent/DK126506B/en unknown
- 1970-07-09 NO NO2702/70A patent/NO126529B/no unknown
- 1970-07-10 JP JP45059991A patent/JPS4928658B1/ja active Pending
- 1970-07-10 AT AT629870A patent/AT301172B/en not_active IP Right Cessation
- 1970-07-10 BE BE753285D patent/BE753285A/en not_active IP Right Cessation
- 1970-07-10 CS CS4875A patent/CS163217B2/cs unknown
- 1970-07-10 GB GB33663/70A patent/GB1281956A/en not_active Expired
- 1970-07-10 FR FR707025745A patent/FR2051671B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2051671B1 (en) | 1973-04-27 |
| CS163217B2 (en) | 1975-08-29 |
| FR2051671A1 (en) | 1971-04-09 |
| AT301172B (en) | 1972-08-25 |
| JPS4928658B1 (en) | 1974-07-29 |
| DE1934902A1 (en) | 1971-01-28 |
| BE753285A (en) | 1971-01-11 |
| DE1934902B2 (en) | 1972-07-20 |
| ES381570A1 (en) | 1972-11-16 |
| SE355370B (en) | 1973-04-16 |
| CH536862A (en) | 1973-05-15 |
| DK126506B (en) | 1973-07-23 |
| NL161484B (en) | 1979-09-17 |
| NL7009880A (en) | 1971-01-12 |
| NL161484C (en) | 1980-02-15 |
| ZA704657B (en) | 1971-05-27 |
| GB1281956A (en) | 1972-07-19 |
| FI49623B (en) | 1975-04-30 |
| FI49623C (en) | 1975-08-11 |
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