CN101343305B - The preparation method of astragaloside IV - Google Patents
The preparation method of astragaloside IV Download PDFInfo
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- CN101343305B CN101343305B CN2007100436788A CN200710043678A CN101343305B CN 101343305 B CN101343305 B CN 101343305B CN 2007100436788 A CN2007100436788 A CN 2007100436788A CN 200710043678 A CN200710043678 A CN 200710043678A CN 101343305 B CN101343305 B CN 101343305B
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- cyclosiversioside
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- alkaline purification
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- QMNWISYXSJWHRY-YLNUDOOFSA-N astragaloside IV Chemical compound O1[C@H](C(C)(O)C)CC[C@]1(C)[C@@H]1[C@@]2(C)CC[C@]34C[C@]4(CC[C@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O)CO4)O)C4(C)C)[C@H]4[C@@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C[C@H]3[C@]2(C)C[C@@H]1O QMNWISYXSJWHRY-YLNUDOOFSA-N 0.000 title claims abstract description 67
- PFKIBRPYVNVMRU-UHFFFAOYSA-N cyclosieversioside F Natural products CC(C)(O)C1COC(C)(C1)C2C(O)CC3(C)C4CC(OC5OC(CO)C(O)C(O)C5O)C6C(C)(C)C(CCC67CC47CCC23C)OC8OCC(O)C(O)C8O PFKIBRPYVNVMRU-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- QMNWISYXSJWHRY-BCBPIKMJSA-N astragaloside IV Natural products CC(C)(O)[C@@H]1CC[C@@](C)(O1)[C@H]2[C@@H](O)C[C@@]3(C)[C@@H]4C[C@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@@H](O)[C@H]5O)[C@H]6C(C)(C)[C@H](CC[C@@]67C[C@@]47CC[C@]23C)O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O QMNWISYXSJWHRY-BCBPIKMJSA-N 0.000 title abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000011347 resin Substances 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003513 alkali Substances 0.000 claims abstract description 14
- 229940107666 astragalus root Drugs 0.000 claims abstract description 6
- IWUMQCYNYDYUKR-UHFFFAOYSA-N cyclosiversioside F Natural products CC(C)(O)C1CCC(C)(O1)C2C(O)CC3C4CC(OC5OC(CO)C(O)C(O)C5O)C6C(C)(C)C(CCC67CC47CCC23C)OC8OCC(O)C(O)C8O IWUMQCYNYDYUKR-UHFFFAOYSA-N 0.000 claims description 54
- 238000000746 purification Methods 0.000 claims description 21
- 239000003463 adsorbent Substances 0.000 claims description 11
- 230000000274 adsorptive effect Effects 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 235000006533 astragalus Nutrition 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 238000003809 water extraction Methods 0.000 claims description 8
- 241001061264 Astragalus Species 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000006286 aqueous extract Substances 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000006228 supernatant Substances 0.000 claims description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 210000004233 talus Anatomy 0.000 claims description 5
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000920 calcium hydroxide Substances 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- 230000008021 deposition Effects 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 235000012204 lemonade/lime carbonate Nutrition 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000005406 washing Methods 0.000 abstract description 4
- SMDOOINVMJSDPS-UHFFFAOYSA-N Astragaloside Natural products C1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)=C1 SMDOOINVMJSDPS-UHFFFAOYSA-N 0.000 abstract description 3
- QMNWISYXSJWHRY-XWJCTJPOSA-N astragaloside Chemical compound O1[C@H](C(C)(O)C)CC[C@]1(C)[C@@H]1[C@@]2(C)CC[C@]34C[C@]4(CC[C@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O)CO4)O)C4(C)C)C4[C@@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)CC3[C@]2(C)C[C@@H]1O QMNWISYXSJWHRY-XWJCTJPOSA-N 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 description 17
- 239000009636 Huang Qi Substances 0.000 description 7
- 239000011575 calcium Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000007949 saponins Chemical class 0.000 description 6
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 5
- 229930182490 saponin Natural products 0.000 description 5
- JLKGXASMCRAVAK-UHFFFAOYSA-N Astragaloside-II Natural products CC(=O)OC1C(O)C(O)COC1OC2CCC34CC35CCC6(C)C(C)(CCC6(O)C7(C)CCC(O7)C(C)(C)O)C5CC(OC8OC(CO)C(O)C(O)C8O)C4C2(C)C JLKGXASMCRAVAK-UHFFFAOYSA-N 0.000 description 4
- LVBLYMQWWGLBRE-UHFFFAOYSA-N Astragaloside-II Chemical compound CC(=O)OC1C(C(COC1OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2)OC7C(C(C(C(O7)CO)O)O)O)C)O)C8(CCC(O8)C(C)(C)O)C)C)O)O LVBLYMQWWGLBRE-UHFFFAOYSA-N 0.000 description 4
- DJHCVWLJAINILQ-UHFFFAOYSA-N Cyclosieversioside D Natural products CC(=O)OC1C(O)C(O)COC1OC2CCC34CC35CCC6(C)C(C(O)CC6(C)C5CC(OC7OC(CO)C(O)C(O)C7O)C4C2(C)C)C8(C)CC(CO8)C(C)(C)O DJHCVWLJAINILQ-UHFFFAOYSA-N 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000010110 Astragalus glycyphyllos Nutrition 0.000 description 2
- 241000045403 Astragalus propinquus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- -1 triterpene glucoside Chemical class 0.000 description 2
- GBPDDYORNLOZID-UHFFFAOYSA-N 84680-75-1 Chemical compound CC(=O)OC1C(OC(=O)C)C(O)COC1OC1CC2C(OC3C(C(O)C(O)C(CO)O3)O)CC3C4(C)CC(O)C(C5(C)OC(CC5)C(C)(C)O)C4(C)CCC43CC42CC1 GBPDDYORNLOZID-UHFFFAOYSA-N 0.000 description 1
- KWZSMZJAHIHRRT-UHFFFAOYSA-N Acetyl astragaloside I Natural products CC(=O)OC1C(OC(C)=O)C(OC(=O)C)COC1OC1C(C)(C)C2C(OC3C(C(O)C(O)C(CO)O3)O)CC3C4(C)CC(O)C(C5(C)OC(CC5)C(C)(C)O)C4(C)CCC43CC42CC1 KWZSMZJAHIHRRT-UHFFFAOYSA-N 0.000 description 1
- LAWPHHZXTUPSDG-UHFFFAOYSA-N Astragaloside I Natural products CC(=O)OC1C(O)COC(OC2CCC34CC35CCC6(C)C(C)(CCC6(O)C7(C)CCC(O7)C(C)(C)O)C5CC(OC8OC(CO)C(O)C(O)C8O)C4C2(C)C)C1OC(=O)C LAWPHHZXTUPSDG-UHFFFAOYSA-N 0.000 description 1
- KXHCYYSIAXMSPA-UHFFFAOYSA-N Astragaloside-I Chemical compound CC(=O)OC1C(OC(=O)C)C(O)COC1OC1C(C)(C)C2C(OC3C(C(O)C(O)C(CO)O3)O)CC3C4(C)CC(O)C(C5(C)OC(CC5)C(C)(C)O)C4(C)CCC43CC42CC1 KXHCYYSIAXMSPA-UHFFFAOYSA-N 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HJCCJZGOBHFQSX-UHFFFAOYSA-N cyclosieversioside B Natural products CC(CCC(O)C(C)(C)OC1OC(CO)C(O)C(O)C1O)C2C(CC3(C)C4CC(O)C5C(C)(C)C(CCC56CC46CCC23C)OC7OCC(O)C(O)C7O)OC8OC(CO)C(O)C(O)C8O HJCCJZGOBHFQSX-UHFFFAOYSA-N 0.000 description 1
- 229930192874 cyclosiversioside Natural products 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
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- 230000035772 mutation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000002997 osteoclast Anatomy 0.000 description 1
- 235000020245 plant milk Nutrition 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
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- Saccharide Compounds (AREA)
Abstract
The invention aims to provide a method for preparing astragaloside IV, which is simple and convenient to operate, high in yield and high in purity. In order to achieve the purpose of the invention, the adopted specific technical scheme is as follows: a process for preparing astragaloside IV from astragalus root includes such steps as extracting in water, alkali treating, adsorbing by macroreticular resin, water washing, washing with diluted alcohol solution, eluting with higher-concentration alcohol solution, concentrating and crystallizing. The astragaloside prepared by the method has the characteristics of light color and high purity, and the preparation method has the characteristics of high yield, low production cost and simple, convenient and standard process.
Description
Technical field
The present invention relates to a kind of preparation method of medicine, being specifically related to a kind of is the method for the high yield high-purity astragaloside of feedstock production with the Chinese medicine astragalus.
Background technology
The Radix Astragali is the dry root of leguminous plants Radix Astagali Astragalus membranaceus (Fisch.) Bge.var.mongholicus (Bge.) Hsiao or Radix Astragali Astragalusmembranaceus (Fisch.) Bge.; Be traditional tonic medicine commonly used, tool invigorating QI to consolidate the body surface resistance, diuresis detoxification; The effect of expelling pus and promoting granulation; Beginning is stated from Shennong's Herbal, is Chinese medicine extremely common in the tcm prescription, and the frequency of using in the Chinese patent medicine is also very high.
Radix Astragali extract is the yellow powder shape.Have strengthening immunity, antifatigue, mutation protects the liver, and suppresses the effect of osteoclast.
A large amount of pharmaceutical research report Radix Astragali saponin constituents are main effective constituent in the Radix Astragali, comprise Cyclosiversioside F (total Astragloside), triterpene glucoside (triterpene glycosides), astragalus polysaccharides (polysaccharides).Wherein, representative composition is Cyclosiversioside F (astragaloside IV), have raise immunity, anti-inflammatory, ease pain, protect the liver, anti-oxidant, anti-ageing, antitumor, cardiac stimulant, hypoglycemic, improve multiple pharmacologically actives such as hemorheology.
The content of Cyclosiversioside F in Milkvetch Root is extremely low, is about 0.04%, and extraction separation is difficulty very, and this has restricted the deep development of Cyclosiversioside F; Can only prepare (surplus blast .RP-HPLC preparative chromatography is separated Cyclosiversioside F for Zhang Jian, Zhang Zhen sea) in a small amount with RP-HPLC, production cost is very high, is not suitable for suitability for industrialized production.
One Chinese patent application numbers 200310108915.6 discloses a kind of preparation method of Cyclosiversioside F, through preparation Cyclosiversioside Fs such as extraction, desugar, decolourings.One Chinese patent application numbers 200510020977.0 discloses a kind of preparation method of Cyclosiversioside F, behind the extraction using alcohol, enrichment, decon, basic hydrolysis, extraction and purifying.But this method step is more, preparing method's trouble.One Chinese patent application numbers 200610012687.6 discloses a kind of preparation method of Cyclosiversioside F, adopts and extracts, and steps such as ethanol decolorization, basic hydrolysis obtain Cyclosiversioside F, have simplified intermediate steps, but yield is not high.
Summary of the invention
The purpose of this invention is to provide a kind of easy and simple to handle, productive rate is high, purity is high Cyclosiversioside F preparation method.
In order to reach the object of the invention; The concrete technical scheme that is adopted is following: the preparation method of Cyclosiversioside F; It is characterized in that; With the Chinese medicine astragalus is raw material, comprises that water extraction, alkaline purification, absorption with macroporous adsorbent resin, washing impurity, rare pure liquid washes impurity, higher concentration alcohol liquid wash-out Cyclosiversioside F, concentrates and crystallisation step.
The preparation method of Cyclosiversioside F specifically comprises the steps: astragalus root is pulverized, and uses water extraction; Merge each several part water extract, use alkaline purification, filtration or centrifugal, filtrating or supernatant directly add on the macroporous adsorptive resins, with deionized water flush away carbohydrate, salt, liposoluble ingredient, are 20%～50% ethanol flush away part water-soluble impurity with concentration again; Be 70%～90% ethanol elution Cyclosiversioside F composition with concentration at last, 70%～90% ethanol eluate is concentrated to small volume, and centrifugal must the deposition with rare lower alcohol recrystallization, gets Cyclosiversioside F.
It is 2～24 hours that the water extract uses the alkaline purification time, transfers pH to 7.5～12.0 then, goes up macroporous adsorptive resins again.The best alkaline purification time is 10～24 hours, transfers pH to 7.5～8.0 then, goes up macroporous adsorptive resins again.Its used alkali is one or more the mixing in calcium hydroxide, sodium hydroxide, Pottasium Hydroxide, yellow soda ash, salt of wormwood, sodium hydrogencarbonate, saleratus, lime carbonate or the ammoniacal liquor.The best approach is preferably in aqueous extract and adds calcium hydroxide and make into saturated solution.
Alkali treatment method in aqueous extract, add alkali or alkaline solution make the pH value of solution value be 8～14 or 14, be preferably the pH value>10.
Used macroporous adsorbent resin is D101 or HPD100 or AB-8 or HP20 or HPD300 or HPD100A or XAD-2 or XAD-4 or HPD400 or HPD400A or ZTC-1 or Didaion HP20.
A kind of as in decocting method or the heating reflux method of the method for wherein using water extraction.
The carbon number of the lower alcohol that the present invention adopts is C1～C3, as is one or more the mixing in methyl alcohol, ethanol, the propyl alcohol.Be preferably ethanol.
Among the present invention, the structure of the Cyclosiversioside F of indication is following:
(1)Astragaloside?IV
Removing Cyclosiversioside F (Astragaloside IV) in the Radix Astragali is main saponin(e, also has the structure following saponin constituent similarly of very small amount:
Difference on these saponin(es and the Cyclosiversioside F comparative structure is the having or not or what branch of ethanoyl on sugar chain only.In the saponin(e of (2)～(5), the content of Astragaloside II compares other more than three.Astragaloside II sample (Chem.Pharm.Bull. with the confession of Wang Hui Kandy; 1983; 31 (2): 698～708) with WITH AMMONIA TREATMENT after thin-layer chromatography inspection; Its converted product is Astragaloside IV, and along with the prolongation Astragaloside II of alkaline purification time can progressively be converted into Astragaloside IV fully.Converted product is differentiated through thin-layer chromatography, Vanillin sulfuric acid test solution coupling reaction, fusing point test, ir spectra and is Astragaloside IV.Moreover the HPLC collection of illustrative plates of comparison alkaline purification front and back sample; There is the peak height of several chromatographic peaks to reduce; And the content of Astragaloside IV increases, and possibly be that these constituents such as Astragaloside II in the Milkvetch Root, Astragaloside I, IsoastragalosideII, Acetylastragaloside I are converted into due to the Astragaloside IV.Explain that alkaline purification helps the increase of Astragaloside IV amount, this also is that Pharmacopoeia of People's Republic of China nineteen ninety-five version (an one) Radix Astragali adopts alkali treatment method to carry out the reason that Astragaloside content is measured.
Macroporous adsorbent resin has the good adsorption selectivity to organism, in the absorption Cyclosiversioside F, carbohydrate content is removed.The physico-chemical property of macroporous adsorbent resin is stable, and is better to organic selectivity, do not receive the influence of inorganic salts and strong ion low molecular compound.Generally speaking, acidic cpd in basic soln by desorption, basic cpd in acidic solution by desorption.And mostly the pigment composition in the plant milk extract is acidic cpd, so uses the alkaline purification aqueous extract before the upper prop, is convenient to water flush away pigment and liposoluble ingredient from the macroporous adsorptive resins.And Cyclosiversioside F is a neutral compound; And as stated,, help the increase of Astragaloside IV amount through alkaline purification; Help removing impurity Cyclosiversioside F is attracted on the resin column to greatest extent, improved the rate of transform and the product yield of Cyclosiversioside F greatly.
Cyclosiversioside F is at 70-90% alcohol wash-out position of macroporous adsorptive resins, and after concentrating, Cyclosiversioside F is separated out owing to solubleness is less in the lower concentration alcoholic solution.
The Cyclosiversioside F of the inventive method preparation is of light color, purity is high, and the preparation method has that yield height, production cost are low, the characteristics of the easy standard of technology.
Embodiment
For technique means, creation characteristic that the present invention is realized, reach purpose and effect and be easy to understand and understand, below in conjunction with embodiment, further set forth the present invention.
The method that from Chinese medicine astragalus, prepares Cyclosiversioside F of the present invention; Comprise that water extraction, alkaline purification, absorption with macroporous adsorbent resin, washing, rare pure liquid are washed, higher concentration alcohol liquid wash-out Cyclosiversioside F, concentrate, all steps of crystallization; Its concrete technology is following: astragalus root is pulverized, used water extraction; Merge each several part water extract; Use alkaline purification, filtration or centrifugal, filtrating or supernatant directly add on the macroporous adsorptive resins; With deionized water flush away carbohydrate, salt, the liposoluble ingredient of 8～10 times of column volumes, again with a part of water-soluble impurity of 20%～50% ethanol flush away of 5～8 column volumes; Be 80%～90% ethanol elution Cyclosiversioside F composition with concentration at last, concentration is that 70%～90% ethanol eluate is concentrated to small volume, centrifugal must the deposition, and this deposition is used the Diluted Alcohol recrystallization, gets Cyclosiversioside F, and purity is 95～98%.
The present invention has compared multiple extraction purifying Astragaloside IV method; As alcohol extracting, water carry, alkaline purification be divided into join on macroporous adsorptive resins pre-treatment and the post handle, the concentration and the treatment time of various alkali, and with patent CN1669566 and CN1544458 in the preparation method of Cyclosiversioside F compare.
The amount such as the following table of concrete experimental technique and Cyclosiversioside F:
Remarks:
1. above-mentioned 14 groups of experiments are all used the corresponding solvent refluxing extraction 3 times, and each 8 times of amounts were extracted 1 hour.
2. macroporous adsorbent resin amount used when going up appearance is all consistent with the eluent elution volume.
3. after going up appearance, the amount of the aqueous solution of used alkali is 5 times of column volumes when on macroporous adsorbent resin, carrying out alkaline purification.
Above-mentioned 14 groups of experimental datas show:
The process for extracting of Cyclosiversioside F with water extraction than good with 80% extraction using alcohol.
2. better than carrying out alkaline purification on the post with the alkaline purification aqueous extract before the post.
3. the kind of alkali is best with saturated calcium hydroxide, and 1% Pottasium Hydroxide takes second place.
The alkaline purification time with 16 hours better, overlong time or too short all bad.
All methods are compared and drawn as drawing a conclusion: the best extraction process of Cyclosiversioside F is the water heating and refluxing extraction, and the water extract adds Ca (OH)
2Pressed powder makes it become Ca (OH) in right amount
2Saturated solution, room temperature was placed 16 hours, and is centrifugal, and supernatant is regulated pH to 8 with dilute hydrochloric acid solution, joins on the macroporous adsorbent resin, in succession with deionized water and 40% ethanol flush away impurity; At last with 80%-90% ethanol elution Cyclosiversioside F composition.
Embodiment 1:
After astragalus root 1kg pulverized, water heating and refluxing extraction 3 times added 10 times of water refluxing extraction 1 hour for the first time, adds 8 times of water refluxing extraction 0.5 hour for the second time, for the third time.United extraction liquid adds Ca (OH)
2Pressed powder makes it become Ca (OH) in right amount
2Saturated solution, room temperature were placed 16 hours, and be centrifugal, and supernatant is regulated pH to 8 with dilute hydrochloric acid solution, joins on the HPD100 macroporous adsorbent resin, with 10 liters deionized-distilled water flush away carbohydrate, salt, again with 5 liter 40% alcohol flush away impurity.With 3 liter 80% alcohol wash-out Cyclosiversioside F, elutriant is concentrated to small volume again, and the centrifugal Cyclosiversioside F that obtains gets Cyclosiversioside F 1.9 grams through the Diluted Alcohol recrystallization, and content is 98%.
Embodiment 2:
After astragalus root 1kg pulverized, water heating and refluxing extraction 3 times added 12 times of water refluxing extraction 1.5 hours for the first time, adds 10 times of water refluxing extraction 1 hour for the second time, for the third time.United extraction liquid adds Ca (OH)
2Pressed powder makes it become Ca (OH) in right amount
2Saturated solution, room temperature were placed 20 hours, and be centrifugal, and supernatant is regulated pH to 8 with dilute hydrochloric acid solution, joins on the D101 macroporous adsorbent resin, with 14 liters deionized-distilled water flush away carbohydrate, salt, again with 5 liter 40% alcohol flush away impurity.With 3 liter 80% alcohol wash-out Cyclosiversioside F, elutriant is concentrated to small volume again, and the centrifugal Cyclosiversioside F that obtains gets Cyclosiversioside F 2.1 grams through the Diluted Alcohol recrystallization, and content is 95%.
More than show and described ultimate principle of the present invention, principal character and advantage of the present invention.The technician of the industry should understand; The present invention is not restricted to the described embodiments; That describes in the foregoing description and the specification sheets just explains principle of the present invention; The present invention also has various changes and modifications under the prerequisite that does not break away from spirit and scope of the invention, and these variations and improvement all fall in the scope of the invention that requires protection.The present invention requires protection domain to be defined by appending claims and equivalent thereof.
Claims (11)
1. the preparation method of Cyclosiversioside F is characterized in that, is raw material with the Chinese medicine astragalus, comprises the steps: astragalus root is pulverized, and uses water extraction; Merge the water extract, use alkaline purification, filtration or centrifugal, filtrating or supernatant directly add on the macroporous adsorptive resins, with deionized water flush away carbohydrate, salt, liposoluble ingredient, are 20%～50% ethanol flush away part water-soluble impurity with concentration again; Be 70%～90% ethanol elution Cyclosiversioside F composition with concentration at last, 70%～90% ethanol eluate is concentrated to small volume, places, and centrifugal must the deposition with rare lower alcohol recrystallization, gets Cyclosiversioside F.
2. the preparation method of Cyclosiversioside F as claimed in claim 1 is characterized in that, a kind of as in decocting method or the heating reflux method of the method for wherein using water extraction.
3. the preparation method of Cyclosiversioside F as claimed in claim 1 is characterized in that, the carbon number of said lower alcohol is C1～C3, in methyl alcohol, ethanol, the propyl alcohol one or more.
4. the preparation method of Cyclosiversioside F as claimed in claim 1 is characterized in that, said lower alcohol is an ethanol.
5. the preparation method of Cyclosiversioside F as claimed in claim 1 is characterized in that, it is 2～24 hours that described water extract uses the alkaline purification time, transfers pH to 7.5～12.0 then, goes up macroporous adsorptive resins again.
6. the preparation method of Cyclosiversioside F as claimed in claim 1 is characterized in that, it is 10～24 hours that described water extract uses the alkaline purification time, transfers pH to 7.5～8.0 then, goes up macroporous adsorptive resins again.
7. the preparation method of Cyclosiversioside F as claimed in claim 1; It is characterized in that; The used alkali of said alkaline purification is following reagent, the mixing of one or more in calcium hydroxide, sodium hydroxide, Pottasium Hydroxide, yellow soda ash, salt of wormwood, sodium hydrogencarbonate, saleratus, lime carbonate or the ammoniacal liquor.
8. the preparation method of Cyclosiversioside F as claimed in claim 1 is characterized in that, the used alkali of said alkaline purification is calcium hydroxide.
9. like the preparation method of the described Cyclosiversioside F of each claim of claim 1, it is characterized in that, said alkali treatment method in aqueous extract, add alkali or alkaline solution make the pH value of solution value be 8～14 or＞14.
10. like the preparation method of the described Cyclosiversioside F of each claim of claim 1, it is characterized in that said alkali treatment method makes pH value of solution value＞10 for adding alkali or alkaline solution in aqueous extract.
11. preparation method like the described Cyclosiversioside F of each claim of claim 1; It is characterized in that; Used macroporous adsorbent resin; Be following resin, D101 or HPD100 or AB-8 or HP20 or HPD300 or HPD100A or XAD-2 or XAD-4 or HPD400 or HPD400A or ZTC-1 or Didaion HP20.
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| CN101781354B (en) * | 2009-01-16 | 2012-01-04 | 劲牌有限公司 | Production method for preparing astragaloside A |
| CN101817861B (en) * | 2009-12-09 | 2015-03-04 | 江苏省中国科学院植物研究所 | Method for preparing high-purity astragaloside for treating diabetes nephropathy and peripheral neuritis of diabetes complications |
| CN101775056B (en) * | 2010-01-28 | 2012-07-04 | 东北林业大学 | Method for extracting, separating and purifying Astragaloside IV from Astragalus mongholicus |
| CN101940610B (en) * | 2010-08-19 | 2012-05-30 | 药都制药集团股份有限公司 | Preparation method of astragalus extract |
| CN102993261B (en) * | 2012-12-15 | 2015-03-25 | 武汉欧尼思化工有限公司 | Technology for preparing high-purity astragaloside based on flocculant and defoamer |
| CN103655600B (en) * | 2013-12-18 | 2016-01-27 | 成都中医药大学 | A kind of pharmaceutical composition of Therapeutic cancer and preparation method and purposes |
| CN105481934A (en) * | 2015-12-02 | 2016-04-13 | 上海景峰制药有限公司 | Astragaloside bulk drug and preparation method thereof |
| CN105541954A (en) * | 2015-12-02 | 2016-05-04 | 上海景峰制药有限公司 | Radix astragali extract with high purity astragaloside |
| CN106083979A (en) * | 2016-06-17 | 2016-11-09 | 浙江工业大学 | Cycloastragenol extract and preparation method and application thereof |
| RU2706697C1 (en) * | 2018-12-28 | 2019-11-20 | Федеральное государственное бюджетное учреждение науки Федеральный исследовательский центр "КОМИ научный центр Уральского отделения Российской академии наук" | Extract of astragalus roots |
| CN110423262A (en) * | 2019-05-23 | 2019-11-08 | 齐齐哈尔医学院 | A kind of Astragalus Root P.E preparation method rich in Astragaloside IV |
| CN110204588B (en) * | 2019-06-12 | 2021-03-30 | 劲牌有限公司 | Method for preparing astragaloside |
| CN111777656B (en) * | 2020-07-21 | 2023-04-18 | 山西大学 | Method for extracting astragaloside from fresh astragalus |
| CN113637046B (en) * | 2021-07-13 | 2024-04-19 | 安徽康信制药有限公司 | Astragaloside IV extraction method with high extraction rate |
| CN117298052A (en) * | 2023-10-16 | 2023-12-29 | 广东医科大学 | Preparation method and application of oral astragaloside IV nano preparation |
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| CN1669566A (en) * | 2004-03-19 | 2005-09-21 | 天津药物研究院 | Preparation method of Astragaloside material medicine, the material medicine and preparation |
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| CN1669566A (en) * | 2004-03-19 | 2005-09-21 | 天津药物研究院 | Preparation method of Astragaloside material medicine, the material medicine and preparation |
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