CN107903292B - Method for extracting stilbene glucoside from polygonum multiflorum - Google Patents
Method for extracting stilbene glucoside from polygonum multiflorum Download PDFInfo
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- CN107903292B CN107903292B CN201711427879.8A CN201711427879A CN107903292B CN 107903292 B CN107903292 B CN 107903292B CN 201711427879 A CN201711427879 A CN 201711427879A CN 107903292 B CN107903292 B CN 107903292B
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- -1 stilbene glucoside Chemical class 0.000 title claims abstract description 54
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 title claims abstract description 52
- 229930182478 glucoside Natural products 0.000 title claims abstract description 51
- 235000021286 stilbenes Nutrition 0.000 title claims abstract description 51
- 241001289529 Fallopia multiflora Species 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000000605 extraction Methods 0.000 claims abstract description 142
- 238000000926 separation method Methods 0.000 claims abstract description 76
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000000047 product Substances 0.000 claims abstract description 39
- 239000000843 powder Substances 0.000 claims abstract description 32
- 238000001914 filtration Methods 0.000 claims abstract description 18
- 239000000706 filtrate Substances 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 16
- 229910021642 ultra pure water Inorganic materials 0.000 claims abstract description 16
- 239000012498 ultrapure water Substances 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- 238000010298 pulverizing process Methods 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 description 19
- 238000000194 supercritical-fluid extraction Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 235000018167 Reynoutria japonica Nutrition 0.000 description 5
- 240000001341 Reynoutria japonica Species 0.000 description 5
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- JAYVHSBYKLLDJC-DSNJPTTOSA-N (E)-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(O)C=C(O)C=C1\C=C\C1=CC=C(O)C=C1 JAYVHSBYKLLDJC-DSNJPTTOSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- VWDXGKUTGQJJHJ-UHFFFAOYSA-N Catenarin Natural products C1=C(O)C=C2C(=O)C3=C(O)C(C)=CC(O)=C3C(=O)C2=C1O VWDXGKUTGQJJHJ-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-QXMHVHEDSA-N Cistacarpin Natural products C=1C=CC=CC=1/C=C\C1=CC=CC=C1 PJANXHGTPQOBST-QXMHVHEDSA-N 0.000 description 1
- 230000033616 DNA repair Effects 0.000 description 1
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- 239000010282 Emodin Substances 0.000 description 1
- RBLJKYCRSCQLRP-UHFFFAOYSA-N Emodin-dianthron Natural products O=C1C2=CC(C)=CC(O)=C2C(=O)C2=C1CC(=O)C=C2O RBLJKYCRSCQLRP-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 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 1
- YOOXNSPYGCZLAX-UHFFFAOYSA-N Helminthosporin Natural products C1=CC(O)=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O YOOXNSPYGCZLAX-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- NTGIIKCGBNGQAR-UHFFFAOYSA-N Rheoemodin Natural products C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1O NTGIIKCGBNGQAR-UHFFFAOYSA-N 0.000 description 1
- 240000004980 Rheum officinale Species 0.000 description 1
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- 238000005411 Van der Waals force Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 150000004777 chromones Chemical class 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- VASFLQKDXBAWEL-UHFFFAOYSA-N emodin Natural products OC1=C(OC2=C(C=CC(=C2C1=O)O)O)C1=CC=C(C=C1)O VASFLQKDXBAWEL-UHFFFAOYSA-N 0.000 description 1
- RHMXXJGYXNZAPX-UHFFFAOYSA-N emodin Chemical compound C1=C(O)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O RHMXXJGYXNZAPX-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- 150000004338 hydroxy anthraquinones Chemical class 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
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- PKUBGLYEOAJPEG-UHFFFAOYSA-N physcion Natural products C1=C(C)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O PKUBGLYEOAJPEG-UHFFFAOYSA-N 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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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
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention discloses a method for extracting stilbene glucoside in polygonum multiflorum, which comprises the following steps: 1) providing polygonum multiflorum powder; 2) adding an entrainer into the polygonum multiflorum powder, wherein the entrainer is ultrapure water; 3) subjecting Polygoni Multiflori radix powder to supercritical CO2Extracting to obtain an extraction product, wherein the extraction temperature is 48-52 ℃, and the extraction pressure is 36-40 Mpa; the extraction product sequentially passes through a separation kettle I and a separation kettle II to obtain a crude stilbene glucoside product, wherein the temperature of the separation kettle I is 43-47 ℃, the pressure of the separation kettle I is 11-13Mpa, the temperature of the separation kettle II is 28-32 ℃, and the pressure of the separation kettle II is 7-9 Mpa; 4) and dissolving the crude stilbene glucoside product by using absolute ethyl alcohol, filtering to obtain filtrate, and drying the filtrate to obtain a stilbene glucoside finished product. The extraction method provided by the invention is convenient to operate, simple in post-treatment, environment-friendly and pollution-free, the extraction rate can reach 5.25%, and the purity can reach 98%.
Description
Technical Field
The invention relates to the field of traditional Chinese medicine extraction, in particular to a method for extracting stilbene glucoside in polygonum multiflorum.
Background
The Polygoni Multiflori radix is root tuber of plant of Polygonaceae, and Li Shizhen is black-colored and white. The Chinese pharmacopoeia uses the root tuber of Polygonaceae plant as the certified product, namely the red fleece-flower root. The compendium of materia Medica records: fleece-flower root has the functions of relieving heart pain, replenishing qi and blood, blackening beard and hair, nourishing the color, growing muscles and bones after long-term use, benefiting marrow and essence and prolonging life. Stilbene glucoside contained in the polygonum multiflorum is a main effective component with the functions of reducing blood fat, benefiting intelligence and resisting aging, and is widely applied to functional foods.
Since the last 90 s, research on the development and application of polygonum multiflorum has been conducted in the united states, japan, etc., and the development of functional foods using polygonum multiflorum as a raw material has entered the international market. In recent years, extraction of stilbene glucoside from polygonum multiflorum as a main chemical component, development of new drugs and functional foods also attract great attention of scientific and technological workers at home and abroad.
CO2The supercritical extraction technology is a technology which is developed rapidly in recent years and is widely applied in the technical field of extraction of effective components of Chinese herbal medicines. The technique has the following advantages: the process has low extraction temperature, and can prevent the effective components in the spice or Chinese herbal medicine from being damaged and maintain the effective componentsBiological activity; in the extraction process, the mass transfer speed is high, the extraction speed is high, and the extraction rate is high; CO22No toxicity, no residual organic solvent, pure natural product, saving a great amount of organic solvent, reducing environmental pollution and easy separation.
At present, in the prior art, the preparation process of the active ingredient stilbene glucoside in polygonum multiflorum is reported to be carried out by using ethanol as a entrainer for CO2Supercritical extraction, however, the method still can not completely extract all the stilbene glucoside in the polygonum multiflorum. In the prior art, no report exists that water is used as a carrying agent to extract stilbene glucoside in polygonum multiflorum and higher extraction rate can be obtained.
Disclosure of Invention
The invention provides an extraction method of stilbene glucoside in polygonum multiflorum, which has the advantages of simple post-treatment, high purity and good extraction yield, and is beneficial to industrial production of stilbene glucoside and mechanism research of stilbene glucoside as medicine.
In order to solve the problems, the invention provides a method for extracting stilbene glucoside in polygonum multiflorum, which comprises the following steps:
1) providing polygonum multiflorum powder;
2) adding an entrainer into the polygonum multiflorum powder, wherein the entrainer is ultrapure water;
3) subjecting Polygoni Multiflori radix powder to supercritical CO2Extracting to obtain an extraction product, wherein the extraction temperature is 48-52 ℃, and the extraction pressure is 36-40 Mpa; the extraction product sequentially passes through a separation kettle I and a separation kettle II to obtain a crude stilbene glucoside product, wherein the temperature of the separation kettle I is 43-47 ℃, the pressure of the separation kettle I is 11-13Mpa, the temperature of the separation kettle II is 28-32 ℃, and the pressure of the separation kettle II is 7-9 Mpa;
4) and dissolving the crude stilbene glucoside product by using ethanol, filtering to obtain a filtrate, and drying the filtrate to obtain a stilbene glucoside finished product.
Preferably, the preparation method of the polygonum multiflorum powder in the step 1) is drying polygonum multiflorum in the shade and crushing into powder of 6-9 meshes.
Preferably, the polygonum multiflorum of step 1) is selected from any one of production places of Wanyuan of Sichuan, Enshi of Hubei, Ankang of Shaanxi and copper kernel of Guizhou.
Preferably, the weight ratio of the entrainer to the polygonum multiflorum in the step 2) is (1.5-2.2): 5.
Preferably, the weight ratio of the entrainer to the polygonum multiflorum in the step 2) is 2: 5.
Preferably, the extraction temperature in the step 3) is 50 ℃ and the pressure is 38 MPa.
Preferably, the step 3) is a circulating extraction, and the extraction time is 1.8-2.2 h.
Preferably, the extraction time of step 3) is 2 h.
Preferably, the temperature of the separation kettle I in the step 3) is 45 ℃, and the pressure is 12 Mpa.
Preferably, the temperature of the separation kettle II in the step 3) is 30 ℃, and the pressure is 8Mpa.
Preferably, CO is present in step 3)2The flow rate is 10-11 l/h.
Preferably, CO is present in step 3)2The flow rate was 10.5 l/h.
Preferably, the filtration in the step 4) is a macroporous resin filtration.
More preferably, the macroporous resin is one or more of D101, DM130, S-8, D600, HPD500, II, ZTC-1.
Supercritical CO2Extraction (SC-CO)2) In, CO2Is a non-polar substance, has the characteristic of selective dissolution, SC-CO2Has excellent solubility for low molecular, low polarity, lipophilic, low boiling point components such as volatile oil, hydrocarbon, ester, lactone, ether, epoxy compound, etc. The effective component of most Chinese medicinal materials is SC-CO with more polar groups and larger molecular weight2The extraction of the material with large molecular weight and polar group content is relatively difficult, and a entrainer is needed to change the solubility of the material. Common entrainers are methanol, ethanol, acetone, ethyl acetate, and the like.
The extract is in SC-CO2The dissolving process in (1) is determined by molecular weight, molecular structure, molecular polarity, amount of hydrophilic/hydrophobic functional groups, and CO2Affinity of the molecule, and the like. After the addition of the entrainer, SC-CO is formed2New body of entrainerFirstly, the solubility of the system is changed; second also to change SC-CO2The critical point of (a); in addition, the entrainer and the solute molecule can form interaction force-Van der Waals force; hydrogen bond complexation and other forces can also be formed between the carrying agent capable of forming hydrogen bonds and the specific functional groups of the solute. The greater the molecular polarity of the entrainer, the solute is in supercritical CO2The greater the solubility of (a); increase in relative molecular mass or molecular volume of entrainer in supercritical CO2The solubility in the solvent is reduced, and the extraction rate is reduced; the entrainer molecules which are easy to form hydrogen bonds can obviously improve the extraction rate; the multi-component entrainer can improve the extraction efficiency more obviously.
The invention adopts water as a carrying agent, the molecular weight of water molecules is less than that of ethanol molecules, and the reduction of the molecular weight and the molecular volume increases the content of stilbene glucoside in polygonum multiflorum in supercritical CO2The solubility in the fluid is closer to the polarity of the stilbene glucoside in the polarity of water molecules, and hydroxyl contained in the water molecules and a plurality of hydroxyl in the stilbene glucoside can form intermolecular hydrogen bonds, so that the supercritical CO is further increased2The extraction efficiency of the fluid is high, the water molecules are free from toxic pollution, and a stilbene glucoside pure product which does not contain an organic solvent, has few impurities and is high in purity is obtained after the stilbene glucoside is filtered by macroporous resin.
The red polygonum multiflorum is dried in the shade, added into a crusher and crushed into powder, the red polygonum multiflorum is produced in any place of the Sichuan Wanyuan, the Hubei Enshi, the Shaanxi Ankang and the Guizhou copper kernel, and the Sichuan Wanyuan and/or the Hubei Enshi are preferred. Accurately weighing a certain amount of powder, loading into an extraction barrel, directly adding entrainer into the extraction barrel, starting a supercritical extraction device, respectively heating an extraction kettle, a separation kettle I and a separation kettle II until the extraction kettle and the separation kettle reach a certain temperature, and opening CO2Gas cylinder, opening a certain amount of CO2And flow rate, when the extraction kettle and the two separation kettles are pressurized to a certain pressure, the circular extraction is started, and the pressure balance of each kettle is kept. After extracting for a certain time, obtaining a separated product. Dissolving with anhydrous ethanol, filtering, and vacuum drying the filtrate for 3 hr to obtain the final product. Comparing with standard substance, measuring content by high performance liquid chromatography, and calculating extraction yield。
The invention overcomes the problem of difficult post-treatment of pure water as a carrying agent. The post-treatment of the extracted substance needs to be dissolved by absolute ethyl alcohol and then filtered by macroporous resin, in the prior art, the solvent which is the same as the entrainer is usually selected for dissolution, and ultrapure water is used as the solvent, so that the fluidity of the macroporous resin is not strong, and the extraction rate of the ultrapure water as the entrainer is low. The post-treatment of the invention firstly adopts absolute ethyl alcohol for dissolution, thus solving the defect of difficult post-treatment and improving the extraction rate.
The invention defines the supercritical CO2The best condition for extracting stilbene glucoside in Polygoni Multiflori radix is that the weight ratio of entrainer ultrapure water to Polygoni Multiflori radix is 2:5, the extraction pressure is 38MPa, and the temperature is 50 ℃; the pressure of the separation kettle I is 12Mpa, and the temperature is 45 ℃; the pressure of the separation kettle II is 8Mpa, and the temperature is 30 ℃; CO22The flow rate is 10.5l/h, the final extraction rate can reach 5.25%, and the purity reaches 98%.
Since the total stilbene glucoside content in polygonum multiflorum is not high, 5.62%, this data comes from article "determination of stilbene glucoside content in different parts of polygonum multiflorum", published by zhao rong hua and zhao yun in 2008 on page 12 of 31 st of the college of traditional Chinese medicine in Yunnan. The extraction method provided by the invention can completely extract the stilbene glucoside component in the polygonum multiflorum, is simple and convenient to operate, has quick post-treatment, is non-toxic and pollution-free, and also defines the best production area of the raw materials as the Wanyuan source in Sichuan and the Enshi in Hubei, thereby being beneficial to the industrial production of the stilbene glucoside and the mechanism research of the stilbene glucoside as the medicine.
Detailed Description
In order that those skilled in the art will better understand the technical solutions of the present invention, the present invention will be further described in detail with reference to the following embodiments.
Polygonum multiflorum, also called Polygonum multiflorum and Polygonum multiflorum, is the dried root tuber of Polygonum multiflorum (Polygonum multiflorum Thunb) of Polygonaceae. Modern medicine shows that the fleece-flower root has multiple functions of enhancing immunity, resisting oxidation, delaying brain aging, improving DNA repair function, prolonging life, reducing cholesterol, improving fat metabolism and the like. The main components of Polygoni Multiflori radix include hydroxyanthraquinone compounds (mainly including emodin, rheum officinale atmosphere, rhein and other glucoside, all stilbene compounds), quinone compounds, stilbene glycoside compounds, amide compounds, chromone compounds, lecithin, and trace elements such as calcium, iron, zinc, manganese, copper, etc.
Stilbene glucoside is a specific bioactive component in Polygoni Multiflori radix, has a chemical name of 2,3,5,4' -tetrahydroxystilbene-2-O-beta-D-glucoside, and has a molecular formula of C20H22O9Molecular weight is 406.39, and chemical structural formula is shown in the following formula.
The product is white amorphous powder, is easy to dissolve in water, methanol, ethanol, acetone, etc., soluble in ethyl acetate and insoluble in lipophilic organic solvent, and can be converted into cis-stilbene glucoside by trans-stilbene glucoside under illumination condition, and is unstable in acidic solution at high temperature (more than 60 deg.C), and can be hydrolyzed into glucose, aglycone or quinone compounds under strong acid and strong base conditions. Studies show that stilbene glucoside has the functions of delaying senility, protecting liver, regulating blood fat, protecting nerve, resisting tumor, etc.
Stilbene glucoside belongs to polyhydroxy compound, has stronger molecular polarity, is easy to dissolve in low molecular alcohol solvent, acetone and the like, and is difficult to dissolve in lipophilic organic solvent. At present, the extraction solvent of stilbene glucoside is ethanol solution which is selected for multiple times, and the extraction process mainly adopts a room temperature cold leaching method, an alkaline leaching acid precipitation method, a heating reflux method, a microwave radiation method, an ultrasonic extraction method and the like. Wherein, the room temperature cold soaking method and the heating reflux method are common large-scale extraction methods.
In the prior art, a supercritical extraction method is also reported to extract stilbene glucoside, ethanol is mostly adopted as a carrying agent, and the extraction rate is improved. But still cannot completely extract the stilbene glucoside component in the polygonum multiflorum. The prior art shows that if the entrainer is replaced by water from ethanol, the extraction rate is lower than that of ethanol, and the industrialization requirement cannot be met.
The invention provides a method for extracting stilbene glucoside from polygonum multiflorum, which comprises the following steps:
1) providing polygonum multiflorum powder; the Polygoni Multiflori radix powder is prepared by drying Polygoni Multiflori radix in the shade, and pulverizing into 6-9 mesh powder.
2) Adding an entrainer into the polygonum multiflorum powder, wherein the entrainer is ultrapure water; the weight ratio of the entrainer to the fleece-flower root is (1.5-2.2) to 5; preferably, the weight ratio of the entrainer to the fleece-flower root is 2: 5.
3) Subjecting Polygoni Multiflori radix powder to supercritical CO2Extracting to obtain an extraction product, wherein the extraction temperature is 48-52 ℃, and the preferred temperature is 50 ℃; the extraction pressure is 36-40 Mpa; the preferred pressure is 38 Mpa; the extraction product sequentially passes through a separation kettle I and a separation kettle II to obtain a crude stilbene glucoside product, wherein the temperature of the separation kettle I is 43-47 ℃, the preferred temperature is 45 ℃, the pressure is 11-13Mpa, and the preferred pressure is 12 Mpa; the temperature of the separation kettle II is 28-32 ℃, the preferred temperature is 30 ℃, the pressure is 7-9Mpa, and the preferred pressure is 8Mpa.
The extraction is a circulating extraction, the extraction time is 1.8-2.2h, and the preferable time is 2 h; CO22The flow rate is 10-11 l/h, preferably 10.5 l/h.
4) And dissolving the crude stilbene glucoside product by using absolute ethyl alcohol, filtering to obtain filtrate, and drying the filtrate to obtain a stilbene glucoside finished product. The filtration is carried out by adopting macroporous resin, and the macroporous resin is preferably one or more of 101, DM130, S-8, D600, HPD500, II and ZTC-1.
The following are examples of the present invention and comparative examples selected from the prior art and closest to the present invention, all using ethanol as a carrier and supercritical CO2The extraction technology is used for extracting stilbene glucoside in the polygonum multiflorum. Wherein comparative example 1 provided only an extraction step and no separation step, the extraction rate was very low, less than < 1%. The comparative example 2 used ethanol as a entrainer, and the extraction conditions were different from the present invention, and the extraction rate obtained was 4.6%. However, in the prior art, almost no ultrapure water is reported as a carrying agent, and even if some researchers tried, the extraction rate is very low and is far lower than that of the extraction using ethanol as a carrying agentAnd (4) rate.
The extraction method provided by the invention utilizes ultrapure water as the entrainer, the amount of the entrainer is far less than that of the prior art, the extraction rate is higher than that of ethanol used as the entrainer in the prior art, the optimal extraction rate can reach more than 5.25 percent, and the purity can reach 98 percent. According to the report of the prior art, the total content of stilbene glucoside in the polygonum multiflorum is 5.62%, the stilbene glucoside in the polygonum multiflorum cannot be completely extracted in a large amount of prior art, the highest extraction rate is 4.6% in the comparison example 2, the invention overcomes the bias of the prior art, improves the extraction rate to 5.25% on the basis of reducing the dosage of the entrainer, improves the extraction rate by nearly one percentage point, approaches the complete extraction of stilbene glucoside in the polygonum multiflorum, and obtains unexpected beneficial technical effects.
The producing area of the polygonum multiflorum is determined by screening, and in a plurality of genuine medicinal materials, the raw material sources of the polygonum multiflorum are finally determined to be the source of the starfish in the invention, namely the source of the starfish in Sichuan, the source of the Hunbei Enshi, the Shaanxi Ankang and the copper kernel in Guizhou, wherein the source of the starfish in Sichuan and the source of the Hunbei Enshi are the preferred producing areas, and the source of the starfish in the Sichuan is the.
The foregoing is a detailed description of the invention and the following is an example of the invention.
Example 1
Taking 500g radix Polygoni Multiflori Preparata powder (produced in WANCHANG) and directly adding 100ml ultrapure water with entrainer into the extraction barrel, starting supercritical extraction device, heating the extraction kettle and two separation kettles respectively to 48 deg.C of the extraction kettle, 43 deg.C of the separation kettle I, and 28 deg.C of the separation kettle II, and opening CO2And (3) opening a gas cylinder with a certain CO2 flow rate of 10 l/h, pressurizing the extraction kettle and the two separation kettles to 36Mpa, 11Mpa and 7Mpa, starting circular extraction, and extracting for 1.8h to obtain a separation product. Dissolving with anhydrous ethanol, filtering with macroporous resin D101, and drying the filtrate to obtain product with purity of 97% and extraction rate of 4.86%.
Example 2
Taking 500g of radix Polygoni Multiflori Preparata powder (Enshi in Hubei of the producing area), directly adding 150ml of ultrapure water with entrainer into an extraction barrel, starting a supercritical extraction device, and subjecting an extraction kettle toAnd heating the two separation kettles respectively to 52 ℃ of the extraction kettle, 47 ℃ of the separation kettle I and 32 ℃ of the separation kettle II, and opening CO2Gas cylinder, opening a certain amount of CO2The flow rate is 11 l/h, when the extraction kettle and the two separation kettles are pressurized to 40Mpa, 13Mpa and 9Mpa, the circulation extraction is started, and the separation product is obtained after 2.2h of extraction. Dissolving with anhydrous ethanol, filtering with macroporous resin DM130, and drying the filtrate to obtain product with purity of 98% and extraction rate of 5.14%.
Example 3
Taking 500g powder of radix Polygoni Multiflori Preparata (produced in Wan Chuan of China), directly adding 220ml ultrapure water with entrainer into extraction barrel, starting supercritical extraction device, heating extraction kettle and two separation kettles respectively to 50 deg.C of extraction kettle, 45 deg.C of separation kettle I, and 30 deg.C of separation kettle II, opening CO2Gas cylinder, opening a certain amount of CO2The flow rate is 10.5l/h, when the extraction kettle and the two separation kettles are pressurized to 38Mpa, 12Mpa and 8Mpa, the circular extraction is started, and the separation product is obtained after 2h of extraction. Dissolving with anhydrous ethanol, filtering with macroporous resin S-8, and drying the filtrate to obtain product with purity of 98% and extraction rate of 5.18%.
Example 4
Taking 500g radix Polygoni Multiflori Preparata powder (produced in WANCHANG) and directly adding 200ml ultrapure water with entrainer into extraction barrel, starting supercritical extraction device, heating extraction kettle and two separation kettles respectively to 50 deg.C of extraction kettle, 45 deg.C of separation kettle I, and 30 deg.C of separation kettle II, opening CO2Gas cylinder, opening a certain amount of CO2The flow rate is 10.5l/h, when the extraction kettle and the two separation kettles are pressurized to 38Mpa, 12Mpa and 8Mpa, the circular extraction is started, and the separation product is obtained after 2h of extraction. Dissolving with anhydrous ethanol, filtering with macroporous resin HPD500, and drying the filtrate to obtain product with purity of 98% and extraction rate of 5.25%.
Example 5
Taking 500g powder of radix Polygoni Multiflori (Enshi in Hubei of producing area), directly adding 200ml ultrapure water with entrainer into the extraction barrel, starting supercritical extraction device, heating the extraction kettle and two separation kettles respectively to 50 deg.C of the extraction kettle, 45 deg.C of the separation kettle I, and 30 deg.C of the separation kettle II, opening CO2Gas cylinder, open to a certain degreeCO2The flow rate is 10.5l/h, when the extraction kettle and the two separation kettles are pressurized to 38Mpa, 12Mpa and 8Mpa, the circular extraction is started, and the separation product is obtained after 2h of extraction. Dissolving with anhydrous ethanol, filtering with macroporous resin ZTC-1, and drying the filtrate to obtain product with purity of 98% and extraction rate of 5.13%.
Example 6
Taking 500g powder of radix Polygoni Multiflori (Shaanxi Ankang in producing area), directly adding 200ml ultrapure water with entrainer into an extraction barrel, starting a supercritical extraction device, respectively heating an extraction kettle and two separation kettles to 50 ℃ of the extraction kettle, 45 ℃ of the separation kettle I and 30 ℃ of the separation kettle II, and opening CO2Gas cylinder, opening a certain amount of CO2The flow rate is 10.5l/h, when the extraction kettle and the two separation kettles are pressurized to 38Mpa, 12Mpa and 8Mpa, the circular extraction is started, and the separation product is obtained after 2h of extraction. Dissolving with anhydrous ethanol, filtering with macroporous resin II, and drying the filtrate to obtain product with purity of 98% and extraction rate of 4.86%.
Example 7
Taking 500g powder of radix Polygoni Multiflori (copper seed of Guizhou province of origin), directly adding 200ml ultrapure water with entrainer into an extraction barrel, starting a supercritical extraction device, respectively heating an extraction kettle and two separation kettles to 50 ℃ of the extraction kettle, 45 ℃ of the separation kettle I and 30 ℃ of the separation kettle II, opening CO2Gas cylinder, opening a certain amount of CO2The flow rate is 10.5l/h, when the extraction kettle and the two separation kettles are pressurized to 38Mpa, 12Mpa and 8Mpa, the circular extraction is started, and the separation product is obtained after a certain period of extraction for 2 h. Dissolving with anhydrous ethanol, filtering with macroporous resin D101, and drying the filtrate to obtain product with purity of 98% and extraction rate of 4.97%.
Comparative example 1
In the prior art, supercritical CO is used2The extraction technology, which takes ethanol as a entrainer, comprises the following steps of:
taking 400g of dried and pulverized Polygoni Multiflori radix coarse powder, extracting at 60 deg.C under 40Mpa for 2 hr with 95% ethanol as 20% of crude drug, drying the extract, and determining with high performance liquid chromatography to obtain stilbene glycoside with purity of 6.192mg.g-1。
The above document does not carry out a separation step and the extraction rate is < 1%.
Comparative example 2
In the prior art, supercritical CO is used2The extraction technology, which takes ethanol as a entrainer, comprises the following steps of:
adding the polygonum multiflorum into a grinder to be ground into powder, accurately weighing 200g of the powder, filling the powder into an extraction barrel, and directly adding 150mL of ethanol as a carrying agent into the extraction barrel. Starting the supercritical extraction device, respectively heating the extraction kettle and the two separation kettles, when the temperature of the extraction kettle reaches 45 ℃, the temperature of the separation kettle I reaches 45 ℃, and the temperature of the separation kettle II reaches 30 ℃, opening CO2The gas cylinder, the extraction kettle is pressurized to 35MPa, the pressure of the separation kettle I is 15MPa, the pressure of the analysis kettle II is 5MPa, the cyclic extraction is started, and CO is introduced2When the flow rate is 12.5L/h, the pressure balance of each kettle can be kept. After extraction for 2.5h, pressure is released, extraction is stopped, and bottom valves of the extraction kettle and the separation kettle are opened to obtain a separation product. Dissolving with ethanol, filtering with macroporous resin, and drying the filtrate in vacuum drying oven at room temperature for 3 hr to obtain the product with extraction rate of 4.64%.
The above is only a preferred embodiment of the present invention, and it should be noted that the above preferred embodiment should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.
Claims (10)
1. A method for extracting stilbene glucoside from Polygoni Multiflori radix comprises the following steps:
1) providing polygonum multiflorum powder;
2) adding an entrainer into the polygonum multiflorum powder, wherein the entrainer is ultrapure water;
3) extracting Polygoni Multiflori radix powder with supercritical CO2 at 48-52 deg.C under 36-40 MPa to obtain extract; the extraction product sequentially passes through a separation kettle I and a separation kettle II to obtain a crude stilbene glucoside product, wherein the temperature of the separation kettle I is 43-47 ℃, the pressure of the separation kettle I is 11-13Mpa, the temperature of the separation kettle II is 28-32 ℃, and the pressure of the separation kettle II is 7-9 Mpa;
4) and dissolving the crude stilbene glucoside product by using absolute ethyl alcohol, filtering to obtain filtrate, and drying the filtrate to obtain a stilbene glucoside finished product.
2. The extraction method according to claim 1, wherein the Polygoni Multiflori radix powder of step 1) is prepared by drying Polygoni Multiflori radix in the shade, and pulverizing into 6-9 mesh powder.
3. The extraction method according to claim 1, wherein the polygonum multiflorum of step 1) is selected from any one of producing areas of Wanyuan of Sichuan, Enshi of Hubei, Ankang of Shaanxi and cuprum of Guizhou.
4. The extraction method according to claim 1, wherein the weight ratio of the entrainer to polygonum multiflorum of step 2) is (1.5-2.2): 5.
5. The extraction process according to claim 1, wherein the extraction temperature in step 3) is 50 ℃ and the pressure is 38 MPa.
6. The extraction method as claimed in claim 1, wherein the step 3) is a circulation extraction, and the extraction time is 1.8-2.2 h.
7. The extraction method according to claim 1, wherein the temperature of the separation vessel I in the step 3) is 45 ℃ and the pressure is 12 MPa.
8. The extraction method according to claim 1, wherein the temperature of the separation vessel II in the step 3) is 30 ℃ and the pressure is 8MPa.
9. The extraction method according to claim 1, wherein the flow rate of CO2 in step 3) is 10-11L/h.
10. The extraction method according to claim 1, wherein the filtration in the step 4) is a filtration using a macroporous resin.
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