CA1148936A - Triterpenic saponin having pharmacological potency - Google Patents
Triterpenic saponin having pharmacological potencyInfo
- Publication number
- CA1148936A CA1148936A CA000351653A CA351653A CA1148936A CA 1148936 A CA1148936 A CA 1148936A CA 000351653 A CA000351653 A CA 000351653A CA 351653 A CA351653 A CA 351653A CA 1148936 A CA1148936 A CA 1148936A
- Authority
- CA
- Canada
- Prior art keywords
- saponin
- units
- beta
- caulophyllogenin
- methanol
- 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
- 150000007949 saponins Chemical class 0.000 title claims abstract description 35
- 239000001397 quillaja saponaria molina bark Substances 0.000 title claims abstract description 34
- 229930182490 saponin Natural products 0.000 title claims abstract description 34
- 230000000144 pharmacologic effect Effects 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 13
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims abstract description 10
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims abstract description 10
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 10
- 241000020085 Chrysanthellum Species 0.000 claims abstract description 8
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical group C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 claims abstract description 8
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 8
- 125000000214 D-xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 7
- 235000013311 vegetables Nutrition 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 241000368571 Opsanus beta Species 0.000 claims abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 238000004237 preparative chromatography Methods 0.000 claims description 4
- 239000003925 fat Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 11
- FABOBEOYNMHSHB-UHFFFAOYSA-N 15R,16-dihydroxy-3-oxoisopimar-9(11)-ene Natural products C1CC(O)C(C)(CO)C2CCC3(C)C4(C)CC(O)C5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C FABOBEOYNMHSHB-UHFFFAOYSA-N 0.000 abstract description 8
- CSJDAUVLWGFTHJ-UHFFFAOYSA-N Caulophyllogenin Natural products CC(O)C(O)C(O)C(OC1OC(C(O)C(O)C1O)C(=O)O)C=O CSJDAUVLWGFTHJ-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004587 chromatography analysis Methods 0.000 abstract description 8
- FABOBEOYNMHSHB-UAWZMHPWSA-N Caulophyllogenin Chemical compound C1C[C@H](O)[C@@](C)(CO)[C@@H]2CC[C@@]3(C)[C@]4(C)C[C@@H](O)[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C FABOBEOYNMHSHB-UAWZMHPWSA-N 0.000 abstract description 7
- 230000001225 therapeutic effect Effects 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 150000008163 sugars Chemical class 0.000 description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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 4
- -1 alditol acetates Chemical class 0.000 description 4
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229930182478 glucoside Natural products 0.000 description 4
- 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 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 230000018109 developmental process Effects 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 150000008131 glucosides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000007792 gaseous phase Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000004816 paper chromatography Methods 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- 241000269350 Anura Species 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- YKOPWPOFWMYZJZ-UHFFFAOYSA-N Echinocystsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CC(O)C5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C YKOPWPOFWMYZJZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- UEHILKCNLIKLEV-UHFFFAOYSA-N UNPD48414 Natural products OC1C(O)C(O)C(C)OC1OC1C(CO)OC(OCC2C(C(O)C(O)C(OC(=O)C34C(CC(C)(C)CC3)C=3C(C5(C)CCC6C(C)(CO)C(OC7C(C(O)C(O)CO7)O)CCC6(C)C5CC=3)(C)CC4)O2)O)C(O)C1O UEHILKCNLIKLEV-UHFFFAOYSA-N 0.000 description 1
- 206010046996 Varicose vein Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008209 arabinosides Chemical class 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- FIMZGFIFLNCCOR-UHFFFAOYSA-N cauloside Natural products CC1(C)C(O)CCC2(C)C(COc3ccc4C=CC(=O)Oc4c3)C(=C)CC(OC5OC(COC6OC(CO)C(O)C(O)C6O)C(O)C(O)C5O)C12 FIMZGFIFLNCCOR-UHFFFAOYSA-N 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 239000000399 hydroalcoholic extract Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- PXUQTDZNOHRWLI-OXUVVOBNSA-O malvidin 3-O-beta-D-glucoside Chemical compound COC1=C(O)C(OC)=CC(C=2C(=CC=3C(O)=CC(O)=CC=3[O+]=2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 PXUQTDZNOHRWLI-OXUVVOBNSA-O 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000003981 vehicle Substances 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
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7911964A FR2456116A1 (fr) | 1979-05-11 | 1979-05-11 | Nouvelle saponine triterpenique derivee de la caulophyllogenine et ses applications therapeutiques |
| FR79.11964 | 1979-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1148936A true CA1148936A (en) | 1983-06-28 |
Family
ID=9225333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000351653A Expired CA1148936A (en) | 1979-05-11 | 1980-05-09 | Triterpenic saponin having pharmacological potency |
Country Status (13)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501734A (en) * | 1981-03-06 | 1985-02-26 | Wakunaga Yakuhin Kabushiki Kaisha | Promotion of absorption of drugs administered through the alimentary system |
| JPS59118053A (ja) * | 1982-12-24 | 1984-07-07 | Hayashibara Biochem Lab Inc | 飲食物とその製造方法 |
| FR2540707A1 (fr) * | 1983-02-16 | 1984-08-17 | Hugues Coffinet | Gomme a macher contenant du ginseng |
| FR2579907A1 (en) * | 1985-04-09 | 1986-10-10 | Couderc Pierre | Method for enriching chrysantellum with active ingredients by physical processes |
| IT1207504B (it) * | 1985-09-26 | 1989-05-25 | Crinos Industria Farmaco | Composizione moderatrice dell'appetito ed antigastrica. |
| US5352449A (en) * | 1986-05-30 | 1994-10-04 | Cambridge Biotech Corporation | Vaccine comprising recombinant feline leukemia antigen and saponin adjuvant |
| US5166139A (en) * | 1987-02-26 | 1992-11-24 | Indena, S.P.A. | Complexes of saponins and their aglycons with phospholipids and pharmaceutical and cosmetic compositions containing them |
| US5057540A (en) * | 1987-05-29 | 1991-10-15 | Cambridge Biotech Corporation | Saponin adjuvant |
| US5583112A (en) * | 1987-05-29 | 1996-12-10 | Cambridge Biotech Corporation | Saponin-antigen conjugates and the use thereof |
| CA1331443C (en) | 1987-05-29 | 1994-08-16 | Charlotte A. Kensil | Saponin adjuvant |
| FR2618071B1 (fr) * | 1987-07-17 | 1991-05-24 | Guillot Bernard | Compositions cosmetiques et dermatologiques a base d'extraits de chrysanthellum |
| US5273965A (en) * | 1992-07-02 | 1993-12-28 | Cambridge Biotech Corporation | Methods for enhancing drug delivery with modified saponins |
| US5650398A (en) * | 1992-07-02 | 1997-07-22 | Cambridge Biotech Corporation | Drug delivery enhancement via modified saponins |
| FR2755609B1 (fr) * | 1996-11-14 | 1998-12-24 | Lanatech | Composition pour la prevention du vieillissement cutane |
| FR2758085B1 (fr) * | 1997-01-09 | 2004-11-19 | Lanatech | Composition amincissante incluant un extrait de chrysanthellum indicum |
| US6172106B1 (en) | 1998-02-09 | 2001-01-09 | R. Armour Forse | Sesamol inhibition of Δ-5-desaturase activity and uses therefor |
| CA2328946C (en) | 1998-04-17 | 2008-02-12 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Agriculture And Agri-Food Canada | Process for recovery and purification of saponins and sapogenins from quinoa (chenopodium quinoa) |
| FR2842109B1 (fr) * | 2002-07-11 | 2007-06-08 | Sicobel Lab | Utilisation d'un extrait de chrysanthellum |
| WO2004078105A2 (fr) * | 2003-02-27 | 2004-09-16 | Sanofi-Synthelabo | Composition de fondaparinux sodique de haute purete |
| US7618946B2 (en) * | 2003-11-27 | 2009-11-17 | Griffith University | Analgesic compounds, extracts containing same and methods of preparation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH410283A (de) * | 1960-06-14 | 1966-03-31 | Klinge Co Chem Pharm Fab | Verfahren zur Gewinnung von genuinem Aescin aus Extrakten der Rosskastanie |
| US3238190A (en) * | 1963-10-23 | 1966-03-01 | Madaus & Co K G Fa Dr | Aescin recovery |
| US3713980A (en) * | 1969-11-25 | 1973-01-30 | Merck Patent Gmbh | Process for the preparation of peruvoside |
| US3723410A (en) * | 1970-12-01 | 1973-03-27 | Amazon Natural Drug Co | Method of producing stevioside |
| IT1064709B (it) * | 1976-07-02 | 1985-02-25 | Snam Progetti | Processo di estrazione di composti glucosidici indesiderabili e.o tossici presenti nei vegetali |
| JPS5338669A (en) * | 1976-09-16 | 1978-04-08 | Toyo Soda Mfg Co Ltd | Separation of natural sweetening agent |
| FR2378044A1 (fr) * | 1977-01-20 | 1978-08-18 | Sarget Lab | Nouvel extrait vegetal a partir de varietes de chrysanthellum |
-
1979
- 1979-05-11 FR FR7911964A patent/FR2456116A1/fr active Granted
-
1980
- 1980-04-22 DE DE19803015363 patent/DE3015363A1/de active Granted
- 1980-04-29 IT IT21712/80A patent/IT1141945B/it active
- 1980-04-29 PT PT71167A patent/PT71167A/pt unknown
- 1980-05-05 MA MA19028A patent/MA18832A1/fr unknown
- 1980-05-07 BE BE0/200502A patent/BE883152A/fr not_active IP Right Cessation
- 1980-05-09 ES ES491354A patent/ES491354A0/es active Granted
- 1980-05-09 CH CH367280A patent/CH645386A5/fr not_active IP Right Cessation
- 1980-05-09 NL NL8002673A patent/NL8002673A/nl not_active Application Discontinuation
- 1980-05-09 CA CA000351653A patent/CA1148936A/en not_active Expired
- 1980-05-10 OA OA57111A patent/OA06531A/xx unknown
- 1980-05-12 ZA ZA00802829A patent/ZA802829B/xx unknown
- 1980-05-12 US US06/148,932 patent/US4335113A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CH645386A5 (fr) | 1984-09-28 |
| MA18832A1 (fr) | 1980-12-31 |
| DE3015363A1 (de) | 1980-11-27 |
| FR2456116B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-05-28 |
| US4335113A (en) | 1982-06-15 |
| ES8101626A1 (es) | 1980-12-16 |
| ES491354A0 (es) | 1980-12-16 |
| DE3015363C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-22 |
| NL8002673A (nl) | 1980-11-13 |
| IT1141945B (it) | 1986-10-08 |
| PT71167A (pt) | 1980-05-01 |
| BE883152A (fr) | 1980-09-01 |
| OA06531A (fr) | 1981-07-31 |
| ZA802829B (en) | 1981-05-27 |
| IT8021712A0 (it) | 1980-04-29 |
| FR2456116A1 (fr) | 1980-12-05 |
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