CS227627B1 - Method of isolating beta-escine - Google Patents
Method of isolating beta-escine Download PDFInfo
- Publication number
- CS227627B1 CS227627B1 CS504882A CS504882A CS227627B1 CS 227627 B1 CS227627 B1 CS 227627B1 CS 504882 A CS504882 A CS 504882A CS 504882 A CS504882 A CS 504882A CS 227627 B1 CS227627 B1 CS 227627B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- extract
- escin
- seeds
- pat
- concentrated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 235000010181 horse chestnut Nutrition 0.000 claims description 6
- 241000157282 Aesculus Species 0.000 claims description 5
- 229940011399 escin Drugs 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- AXNVHPCVMSNXNP-IVKVKCDBSA-N (2s,3s,4s,5r,6r)-6-[[(3s,4s,4ar,6ar,6bs,8r,8ar,9r,10r,12as,14ar,14br)-9-acetyloxy-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(e)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3, Chemical compound O([C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2[C@]1(CO)C)C)(C)C[C@@H](O)[C@@]1(CO)[C@@H](OC(C)=O)[C@@H](C(C[C@H]14)(C)C)OC(=O)C(/C)=C/C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O AXNVHPCVMSNXNP-IVKVKCDBSA-N 0.000 claims description 4
- AXNVHPCVMSNXNP-GKTCLTPXSA-N Aescin Natural products O=C(O[C@H]1[C@@H](OC(=O)C)[C@]2(CO)[C@@H](O)C[C@@]3(C)[C@@]4(C)[C@@H]([C@]5(C)[C@H]([C@](CO)(C)[C@@H](O[C@@H]6[C@@H](O[C@H]7[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)[C@@H](O)[C@H](O[C@H]7[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O7)[C@@H](C(=O)O)O6)CC5)CC4)CC=C3[C@@H]2CC1(C)C)/C(=C/C)/C AXNVHPCVMSNXNP-GKTCLTPXSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229940093314 beta-escin Drugs 0.000 claims description 4
- AXNVHPCVMSNXNP-BEJCRFBNSA-N beta-escin Natural products CC=C(/C)C(=O)O[C@H]1[C@H](OC(=O)C)[C@]2(CO)[C@H](O)C[C@@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@H]6O[C@@H]([C@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@@H]6O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)C(=O)O)[C@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2CC1(C)C AXNVHPCVMSNXNP-BEJCRFBNSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 description 6
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 241000157280 Aesculus hippocastanum Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález sa týká spósobu izolácie ft-escínu zo semien pagaštana koňského (Aesculus hippocastanum)·FIELD OF THE INVENTION The present invention relates to a method for the isolation of ft-escin from the seeds of the horse-chestnut (Aesculus hippocastanum).
Zo semien pagaštana koňského sa izoluje ft-escín extrakciou alkoholmi, alebo ich zmesou s vodou, napr· metanol - voda 80 : 20 (pat· NDR 11 178) až 65 : 35 (pat· NSR 25 30 941); z extraktu sa fc-escín vyzráža cholesterolom (pat· NSR 11 25 117), alebo sa extrakt preleje cez ionomenič v H-cykle (pat· NSR 25 30 941), alebo okyslí organickou připadne minerálnou kyselinou do pHFrom horse-chestnut seeds, ft-escin is isolated by extraction with alcohols or a mixture thereof with water, e.g., methanol-water 80: 20 (pat. GDR 11 178) to 65: 35 (pat. NS 30 25 30 941); from the extract, the β-escin is precipitated with cholesterol (pat · NSR 11 25 117), or the extract is passed through an ion exchanger in the H-cycle (pat · NSR 25 30 941), or acidified with an organic or mineral acid to pH
1,5 až 2,0 (pat. NDR 11 178), zahustí a ft-escín sa vyzráža prídavkom vody (pat. NDR 11 178). Ďalšie postupy využívajú extrakciu pomletých semien vyššími alifatickými alkoholmi (pat. francúzsky 77 24 689, pat. španielsky 455 693) alebo ternámymi zmesami ako metanol - chloroform - voda (pat. NSR 23 39 760). Je známy aj postup extrakcie semien pagaštana koňského vodným amoniakom a následnou úpravou pH a extrakciou izopropanolom (pat. ZSSR 483 982).1.5 to 2.0 (U.S. Pat. No. 11,178), concentrated, and ft-escin precipitated by the addition of water (U.S. Pat. No. 11,178). Other processes utilize the extraction of ground seeds with higher aliphatic alcohols (pat. French 77 24 689, pat. Spanish 455 693) or with known mixtures such as methanol-chloroform-water (pat. Germany 23 39 760). It is also known to extract equine grapevine seeds with aqueous ammonia followed by pH adjustment and isopropanol extraction (U.S. Pat. No. 483,982).
Pri spósobe izolácie ft-escínu zo semien pagaštana koňského podlá vynálezu sa postupuje tak, že rozdrvené semená sa extrahujú zmesou metanol - voda v pomere 1:1, extrakt sa pri teplote 20 až 40°C, s výhodou pri 35°C zahustí na 1/5 až 1/4 póvodného objemu, k zahuštěnému extraktu sa pri teplote 10 až 25°C s výhodou pri teplote 18°C přidá silná minerálna kyselina, s výhodou kyselina sírová alebo fosforečná do pH 1,0, okyslený roztok sa zahřeje na teplotu 40 až 60°C, s výhodou na teplotu 45° C a vylíčený fc-escín sa izoluje.The process for isolating ft-escin from horse chestnut seeds according to the invention is carried out by extracting the crushed seeds with a 1: 1 methanol-water mixture, concentrating the extract at 20 to 40 ° C, preferably at 35 ° C to 1: 1. 5 to 1/4 of the original volume, a strong mineral acid, preferably sulfuric or phosphoric acid is added to the concentrated extract at a temperature of 10 to 25 ° C, preferably at 18 ° C, to a pH of 1.0, and the acidified solution is heated to a temperature 40 to 60 ° C, preferably to 45 ° C and the depicted β-escin is isolated.
227 627227 627
Výhodou postupu podlá vynálezu oproti známým postupom je, že oDtimálnym zložením extrakčnej zmesi sa odstránia nežiadúce příměsi zo semien, zahušťováním extraktu pri teplote 20 až 40°C a až nasledovným okyslením zvyšku sa zvýši výťažok extrakcie a zamedzí sa rozkladu (b-escínu a zahriatim okyslenáho sa vylúči /b-escín vo vhodnéj mikrokryštalickej formě.The advantage of the process according to the invention is that the optimum composition of the extraction mixture removes undesirable impurities from the seeds, by concentrating the extract at a temperature of 20 to 40 ° C, and only by subsequent acidification of the residue increases the extraction yield and avoids decomposition. the β-escin is precipitated in a suitable microcrystalline form.
Bližšie podrobnosti postupu podlá vynálezu sú zřejmé z příkladu prevedenia.Further details of the process according to the invention are apparent from an exemplary embodiment.
Příklad 1Example 1
100 g vysušených, neodmastených, neodšupováných, jemno pomletých semien pagaštana koňského sa po čiastkách přidává za intenzívneho miešania k 950 ml zmesi metanol - voda (1 : 1). Suspenzia sa pri laboratorněj teplote mieša 30 minut, přefiltruje sa, zvyšok na filtri sa premyje 50 ml extrakčnej zmesi, filtrát sa vákuovo zahustí pri teplote 35°C na objem 250 ml. Vzniknutý žltohnedý roztok sa prídavkom 5M H^SO^ na pH 1,0, okyslený roztok sa zahřeje na teplotu 45°C a nechá sa kryštalizovať. Vyl účelná tuhá látky sa odfiltruje. Po rekryštalizácii z metanolu sa získá produkt o t.t. 229-231°C (rozkl.) (VJ ρθ -27±2° (c= 5 v metanole), obsah vody 11,8%, číslo kyslosti v sušině 50,7, číslo zmydelnenia v sušině 153,1, obsah fo-escínu v sušině spektrofotometrichy (Schlemmer W.: Dtsch. Apoth. Ztg. 106, 1315, 1966) 99,8%.100 g of dried, non-degreased, non-peeled, finely ground horse chestnut seeds are added in portions to 950 ml of methanol-water (1: 1) with vigorous stirring. The suspension is stirred at room temperature for 30 minutes, filtered, the filter residue is washed with 50 ml of extraction mixture, the filtrate is concentrated under vacuum at 35 ° C to a volume of 250 ml. The resulting yellow-brown solution was added a 5 M vkom H ^ SO ^ to pH 1.0. The acidified solution was heated to 45 DEG C. and allowed to crystallize. The useful solid is filtered off. After recrystallization from methanol, the product is obtained at mp 229-231 ° C (dec.) (VJ ρθ -27 ± 2 ° (c = 5 in methanol), water content 11.8%, acid value in dry matter 50.7, number saponification in dry matter 153.1, foscin content in dry matter spectrophotometry (Schlemmer W .: Dtsch. Apoth. Ztg. 106, 1315, 1966) 99.8%.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS504882A CS227627B1 (en) | 1982-07-02 | 1982-07-02 | Method of isolating beta-escine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS504882A CS227627B1 (en) | 1982-07-02 | 1982-07-02 | Method of isolating beta-escine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS227627B1 true CS227627B1 (en) | 1984-04-16 |
Family
ID=5394585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS504882A CS227627B1 (en) | 1982-07-02 | 1982-07-02 | Method of isolating beta-escine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS227627B1 (en) |
-
1982
- 1982-07-02 CS CS504882A patent/CS227627B1/en unknown
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