DE2416979C3 - Verfahren zur Gewinnung des in den Wurzeln und Rhizomen von Helleborus-Arten enthaltenen Hauptsapogenins - Google Patents
Verfahren zur Gewinnung des in den Wurzeln und Rhizomen von Helleborus-Arten enthaltenen HauptsapogeninsInfo
- Publication number
- DE2416979C3 DE2416979C3 DE2416979A DE2416979A DE2416979C3 DE 2416979 C3 DE2416979 C3 DE 2416979C3 DE 2416979 A DE2416979 A DE 2416979A DE 2416979 A DE2416979 A DE 2416979A DE 2416979 C3 DE2416979 C3 DE 2416979C3
- Authority
- DE
- Germany
- Prior art keywords
- rhizomes
- roots
- helleborus
- cellulase
- water
- 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
- 241000206389 Helleborus Species 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 12
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 title description 11
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 title description 11
- 108010059892 Cellulase Proteins 0.000 claims description 23
- 229940106157 cellulase Drugs 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 7
- 229930183217 Genin Natural products 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- -1 aliphatic halogenated hydrocarbons Chemical class 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- 229930182490 saponin Natural products 0.000 description 4
- 150000007949 saponins Chemical class 0.000 description 4
- 235000017709 saponins Nutrition 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- HNNFRQFXBWSJBX-UHFFFAOYSA-N 5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde Chemical compound OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C5=COC(=O)C=C5)C4(C)CCC3C2(C=O)CC1 HNNFRQFXBWSJBX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 108010084185 Cellulases Proteins 0.000 description 2
- 102000005575 Cellulases Human genes 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000693937 Helleborus viridis Species 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 230000000026 anti-ulcerogenic effect Effects 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 108010093305 exopolygalacturonase Proteins 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- DCSLTSSPIJWEJN-UHFFFAOYSA-N (3beta,5beta)-3-[(6-deoxy-4-O-beta-D-glucopyranosyl-alpha-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxo-bufa-20,22-dienolide Natural products OC1C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(C)OC1OC(CC1(O)CCC2C3(O)CC4)CCC1(C=O)C2CCC3(C)C4C=1C=CC(=O)OC=1 DCSLTSSPIJWEJN-UHFFFAOYSA-N 0.000 description 1
- DCSLTSSPIJWEJN-YRFFWODSSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,3r,4s,5r,6s)-3,4-dihydroxy-6-methyl-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[ Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@@]5(O)CC[C@H]4[C@@]3(O)CC2)O[C@@H]2O[C@H]([C@@H]([C@@H](O)[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C)C=CC(=O)OC=1 DCSLTSSPIJWEJN-YRFFWODSSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 108091005508 Acid proteases Proteins 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 241000228197 Aspergillus flavus Species 0.000 description 1
- 241001225321 Aspergillus fumigatus Species 0.000 description 1
- 241000351920 Aspergillus nidulans Species 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 208000035404 Autolysis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 description 1
- 206010057248 Cell death Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101710121765 Endo-1,4-beta-xylanase Proteins 0.000 description 1
- 102000005593 Endopeptidases Human genes 0.000 description 1
- 108010059378 Endopeptidases Proteins 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 1
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 1
- 241000206417 Helleborus foetidus Species 0.000 description 1
- 241000693825 Helleborus multifidus Species 0.000 description 1
- 241000693827 Helleborus niger Species 0.000 description 1
- 241000693829 Helleborus odorus Species 0.000 description 1
- 241000693817 Helleborus orientalis Species 0.000 description 1
- 241000693818 Helleborus purpurascens Species 0.000 description 1
- FUTYDOSGHYCQGU-UHFFFAOYSA-N Hellebrin Natural products CC1OC(OC2CCC3(C=O)C4CCC5(C)C(CCC5(O)C4CCC3(O)C2)C6=COC(=O)C=C6)C(OC7OC(CO)C(O)C(O)C7O)C(O)C1O FUTYDOSGHYCQGU-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108010059820 Polygalacturonase Proteins 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 108010047754 beta-Glucosidase Proteins 0.000 description 1
- 102000006995 beta-Glucosidase Human genes 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960000530 carbenoxolone Drugs 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003640 drug residue Substances 0.000 description 1
- 206010013864 duodenitis Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- MPTVOJQMOKMTNP-UHFFFAOYSA-N ethylbenzene;toluene Chemical compound CC1=CC=CC=C1.CCC1=CC=CC=C1 MPTVOJQMOKMTNP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 108010002430 hemicellulase Proteins 0.000 description 1
- 229940059442 hemicellulase Drugs 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000028043 self proteolysis Effects 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002408 ulcerprotective effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2416979A DE2416979C3 (de) | 1974-04-08 | 1974-04-08 | Verfahren zur Gewinnung des in den Wurzeln und Rhizomen von Helleborus-Arten enthaltenen Hauptsapogenins |
| JP4213875A JPS5728558B2 (OSRAM) | 1974-04-08 | 1975-04-07 | |
| GB14092/75A GB1502874A (en) | 1974-04-08 | 1975-04-07 | Recovery of the main sapogenin from helleborus species |
| BE6044980A BE827658A (fr) | 1974-04-08 | 1975-04-07 | Procede pour obtenir la sapogenine principale contenue dans les racines et les rhizomes du genre hellebore et produits obtenus |
| FR7510728A FR2266703B1 (OSRAM) | 1974-04-08 | 1975-04-07 | |
| NL7504109A NL7504109A (nl) | 1974-04-08 | 1975-04-07 | Werkwijze voor het winnen van het in de wortels en rizomen van helleborus-soorten voorkomende hoofdsapogenine. |
| US05/565,698 US4004976A (en) | 1974-04-08 | 1975-04-07 | Process for recovering the main sapogenins from the roots of rhizomes of helleborus |
| AT266875A AT344316B (de) | 1974-04-08 | 1975-04-08 | Verfahren zur gewinnung des in den wurzeln und rhizomen von helleborus-arten enthaltenen hauptsapogenins |
| CA224,029A CA1050427A (en) | 1974-04-08 | 1975-04-08 | Pharmaceutical preparation containing the principal helleborus sapogenin |
| CH445975A CH596239A5 (OSRAM) | 1974-04-08 | 1975-04-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2416979A DE2416979C3 (de) | 1974-04-08 | 1974-04-08 | Verfahren zur Gewinnung des in den Wurzeln und Rhizomen von Helleborus-Arten enthaltenen Hauptsapogenins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2416979A1 DE2416979A1 (de) | 1975-10-09 |
| DE2416979B2 DE2416979B2 (de) | 1978-02-02 |
| DE2416979C3 true DE2416979C3 (de) | 1978-10-12 |
Family
ID=5912426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2416979A Expired DE2416979C3 (de) | 1974-04-08 | 1974-04-08 | Verfahren zur Gewinnung des in den Wurzeln und Rhizomen von Helleborus-Arten enthaltenen Hauptsapogenins |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4004976A (OSRAM) |
| JP (1) | JPS5728558B2 (OSRAM) |
| AT (1) | AT344316B (OSRAM) |
| BE (1) | BE827658A (OSRAM) |
| CH (1) | CH596239A5 (OSRAM) |
| DE (1) | DE2416979C3 (OSRAM) |
| FR (1) | FR2266703B1 (OSRAM) |
| GB (1) | GB1502874A (OSRAM) |
| NL (1) | NL7504109A (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0585988T3 (da) * | 1992-07-27 | 1996-06-24 | Gist Brocades Nv | Enzymprodukt og fremgangsmåde til forbedning af brødkvalitet |
| US5990283A (en) * | 1994-05-12 | 1999-11-23 | The Penn State Research Foundation | Proteins catalyzing the extension of plant cell walls |
| US5959082A (en) * | 1993-05-12 | 1999-09-28 | The Penn State Research Foundation | Proteins catalyzing the extension of plant cell walls |
| US7226756B2 (en) * | 1993-05-12 | 2007-06-05 | The Penn State Research Foundation | Purified plant expansin proteins and DNA encoding same |
| US6326470B1 (en) | 1997-04-15 | 2001-12-04 | The Penn State Research Foundation | Enhancement of accessibility of cellulose by expansins |
| WO1994026878A1 (en) * | 1993-05-12 | 1994-11-24 | The Penn State Research Foundation | Expansins, proteins that catalyze plant cell wall expansion and weakening of paper fiber connections |
| AU3589899A (en) | 1998-04-17 | 1999-11-08 | Her Majesty The Queen In Right Of Canada As Represented By The Department Of Agriculture And Agri-Food Canada | Process for recovery and purification of saponins and sapogenins from quinoa ((chenopodium quinoa)) |
| AU2002256276A1 (en) * | 2001-04-19 | 2002-11-05 | Penn State Research Foundation | Novel expansin polynucleotides, related polypeptides and methods of use |
| RU2207141C2 (ru) * | 2001-08-10 | 2003-06-27 | Паршичев Герман Владимирович | Биологически активный препарат - масло морозника |
| EP2224939B1 (de) * | 2007-12-21 | 2015-03-18 | Finzelberg GmbH & Co. KG | Zubereitungen mit hagebuttenextrakten sowie verfahren zur herstellung von hagebuttenextrakten |
| EP2288361B1 (de) * | 2008-05-06 | 2013-08-21 | Finzelberg GmbH & Co. KG | Zistrosenextrakt mit angereicherten sekundären pflanzeninhaltsstoffen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1492130B1 (de) * | 1963-05-30 | 1971-08-26 | Shionogi & Co | Verfahren zur Herstellung von Saponin-Tetraglycosiden aus Blaettern von Digitalis-Pflanzen |
-
1974
- 1974-04-08 DE DE2416979A patent/DE2416979C3/de not_active Expired
-
1975
- 1975-04-07 FR FR7510728A patent/FR2266703B1/fr not_active Expired
- 1975-04-07 NL NL7504109A patent/NL7504109A/xx not_active Application Discontinuation
- 1975-04-07 BE BE6044980A patent/BE827658A/xx unknown
- 1975-04-07 JP JP4213875A patent/JPS5728558B2/ja not_active Expired
- 1975-04-07 US US05/565,698 patent/US4004976A/en not_active Expired - Lifetime
- 1975-04-07 GB GB14092/75A patent/GB1502874A/en not_active Expired
- 1975-04-08 AT AT266875A patent/AT344316B/de not_active IP Right Cessation
- 1975-04-08 CH CH445975A patent/CH596239A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7504109A (nl) | 1975-10-10 |
| JPS50148516A (OSRAM) | 1975-11-28 |
| FR2266703B1 (OSRAM) | 1977-07-22 |
| DE2416979B2 (de) | 1978-02-02 |
| AT344316B (de) | 1978-07-10 |
| GB1502874A (en) | 1978-03-08 |
| JPS5728558B2 (OSRAM) | 1982-06-17 |
| ATA266875A (de) | 1977-11-15 |
| DE2416979A1 (de) | 1975-10-09 |
| FR2266703A1 (OSRAM) | 1975-10-31 |
| CH596239A5 (OSRAM) | 1978-03-15 |
| US4004976A (en) | 1977-01-25 |
| BE827658A (fr) | 1975-10-07 |
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| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |