CN109593034B - Method for preparing shikimic acid from ginkgo leaf extraction waste liquid - Google Patents
Method for preparing shikimic acid from ginkgo leaf extraction waste liquid Download PDFInfo
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- CN109593034B CN109593034B CN201811397363.8A CN201811397363A CN109593034B CN 109593034 B CN109593034 B CN 109593034B CN 201811397363 A CN201811397363 A CN 201811397363A CN 109593034 B CN109593034 B CN 109593034B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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Abstract
The invention relates to the field of extraction and purification of plant effective ingredients, and particularly provides a method for preparing shikimic acid from ginkgo leaf extraction waste liquid. The method is simple and convenient to operate, economical and practical, is suitable for popularization, does not need to use an organic solvent, and the obtained shikimic acid has high purity, the mass content of more than 99 percent and good appearance.
Description
Technical Field
The invention relates to the field of extraction and purification of plant effective ingredients, and particularly provides a method for preparing shikimic acid from ginkgo leaf extraction waste liquid.
Background
The molecular formula of shikimic acid is C7H10O5, the scientific name is 3,4, 5-trihydroxy-1-cyclohexene-1-carboxylic acid, which is a hydroxy acid. Shikimic acid is an intermediate for synthesizing in vivo and metabolic compounds, and is also a raw material for synthesizing a plurality of alkaloids, aromatic amino acids, indole derivatives and chiral drugs (such as antiviral drugs).
The 2015 edition of Chinese pharmacopoeia stipulates that the folium Ginkgo extract is prepared by subjecting folium Ginkgo extract to macroporous adsorbent resin column chromatography, sequentially washing and eluting with water and ethanol water solution, collecting eluate, concentrating, and drying. The chromatography flow-through or wash liquid in the process is generally treated as waste liquid. Because the adsorption capacity of the industrial common macroporous resin to the shikimic acid in the ginkgo leaf extracting solution is weak, the shikimic acid is lost in the waste liquid of the chromatography process. If shikimic acid can be recovered from the chromatography waste liquid of the ginkgo biloba extract, on one hand, the total organic carbon content in the waste water can be reduced, and the difficulty of waste water treatment is reduced; on the other hand, the ginkgo leaf resource can be more fully utilized, and more valuable products are produced. The shikimic acid extracted from the ginkgo waste liquid is usually extracted by a solvent extraction method, a silica gel column chromatography method and an anion exchange resin adsorption method, but the method has the disadvantages of complex operation, low yield of the extracted shikimic acid, low content and poor product quality.
Disclosure of Invention
In order to solve the defects of the prior art, the method for extracting shikimic acid from the waste liquid left by extracting ginkgo leaves is provided, the method is simple and convenient to operate, the process is economic and environment-friendly, the popularization is suitable, and the obtained shikimic acid has high purity and good appearance and appearance.
The purpose of the invention is realized by the following technical scheme:
a method for preparing shikimic acid from folium Ginkgo extraction waste liquid comprises performing enzymolysis on folium Ginkgo extraction waste liquid, collecting enzymolysis liquid, filtering with organic membrane, adsorbing and eluting with anion exchange resin column, concentrating, crystallizing and drying;
the ginkgo leaf extraction waste liquid is an effluent liquid of a ginkgo leaf extracting solution subjected to macroporous adsorption resin column chromatography, and the ginkgo leaf extracting solution is generated in the process of preparing a ginkgo leaf extract according to 2015 edition Chinese pharmacopoeia;
the biological enzyme used in the enzymolysis process is at least one selected from pectinase, cellulase, papain or amylase.
Preferably, the enzymolysis temperature is 45-60 ℃, and the enzymolysis time is 1-3 hours.
Preferably, the adding amount of the biological enzyme is one thousandth to eight thousandth of the weight of the ginkgo leaf extraction waste liquid.
Preferably, the organic membrane filtration step comprises a first filtration and a second filtration, wherein the first filtration uses an organic membrane with a molecular weight cut-off of 8000, and the filtration pressure is 0.45-0.5 MPa; and the second filtration uses an organic membrane with the molecular weight of 800, and the filtration pressure is 1.8-2.0 MPa.
Preferably, the eluent used for eluting the anion exchange resin column is 0.1-1.5 mol/L of inorganic acid solution, the inorganic acid solution is one of hydrochloric acid, formic acid, acetic acid or sulfuric acid solution, and the dosage of the eluent is 3-6 times of the volume of the anion exchange resin column.
Preferably, the collection is initiated when the pH of the effluent from the anion exchange resin column elution is less than 7.
Preferably, the solid content of the concentrated solution obtained in the concentrating step is more than 50% brix, and the pH of the concentrated solution is 1.0-1.5.
Preferably, the crystallization temperature in the crystallization step is 4-10 ℃, and the crystallization time is more than 4 hours.
Preferably, the ion exchange resin adsorption elution further comprises a yeast fermentation treatment step before.
Preferably, the yeast fermentation is aerobic fermentation, the fermentation temperature is 30-35 ℃, the fermentation time is 36-48 hours, and the mass ratio of the ginkgo leaf extraction waste liquid to the yeast is 1: 0.003-1: 0.03.
The extraction method has the following beneficial effects:
1. the extraction method has reasonable process design, and the shikimic acid extracted from the ginkgo leaf extract waste liquid has high purity and the shikimic acid content is more than 99 percent.
2. The method utilizes biological enzyme enzymolysis to decompose impurities in the ginkgo leaf extract waste liquid, thereby facilitating the next purification.
3. The method utilizes an organic membrane to concentrate and decolor the collected enzymolysis liquid, so that the finally obtained product has pure color.
4. The shikimic acid content in the effluent collected after purification by ion exchange resin is improved by more than 20 percent compared with the prior art.
5. The filtrate obtained before the purification of the ion exchange resin and after the filtration of the organic membrane is fermented by yeast, so that impurities such as saccharides and the like generated in the enzymolysis process and which cannot be completely removed by membrane filtration can be further removed, and the purity of the shikimic acid is further improved; before fermentation, biological enzyme is utilized to decompose substances such as polysaccharide, protein and the like in shikimic acid into organic substances such as micromolecular monosaccharide, amino acid and the like, and yeast can directly use the micromolecular substances, so that the time required by the fermentation link is greatly shortened. The yeast fermentation is carried out under aerobic condition, the products of the yeast aerobic fermentation are carbon dioxide and water, no new impurities are introduced, and after the fermentation is finished, the yeast is not required to be specially sterilized, so that the preparation process is simpler.
6. The aim of crystallization and separation can be achieved at one time by adjusting the optimal PH value required by shikimic acid crystallization, and the product crystallized can fully meet the purity requirement.
7. The product prepared by the preparation method has uniform size and good quality and meets the market requirement.
8. The method only uses the hydrosolvent in the whole process, does not use toxic organic reagent, has environment-friendly production process and simple operation, and is very suitable for industrial large-scale production.
9. The product prepared by the preparation method is snow white, has no bitter taste, no solvent residue, no pesticide residue and stable product quality.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the embodiments of the present invention are not limited to the scope of the examples. These examples are intended to illustrate the invention only and are not intended to limit the scope of the invention. In addition, various modifications may occur to those skilled in the art upon reading the present disclosure, and such equivalent variations are within the scope of the present invention as defined in the appended claims.
In the following examples, the raw materials used for preparing shikimic acid are all ginkgo leaf extraction waste liquid, which is the effluent of a ginkgo leaf extract by macroporous adsorbent resin column chromatography, and the ginkgo leaf extract is generated in the process of preparing a ginkgo leaf extract according to 2015 edition of Chinese pharmacopoeia.
Example 1
Adding cellulase into 100g of ginkgo leaf extraction waste liquid, wherein the dosage of the cellulase is 0.1g, carrying out enzymolysis for 3 hours at the temperature of 45 ℃ to obtain an enzymolysis liquid, enabling the enzymolysis liquid to pass through an organic membrane, firstly passing through the organic membrane with the molecular weight of 8000, then passing through the organic membrane with the molecular weight of 800, and then passing through the organic membrane with the molecular weight of 800, wherein the membrane pressure is 2.0MPa to obtain a decolored membrane passing liquid, directly passing through the membrane liquid into strongly alkaline anion resin D290 (Tianjin south China resin factory), eluting and separating by using hydrochloric acid solution with the volume of 4 times of the column volume of 0.5mol/L after the membrane passing is finished, and collecting the solution from the beginning when the pH of an effluent liquid is less than 7. Concentrating the effluent under reduced pressure to obtain a concentrate containing 55% brix, adjusting pH to 1.0 with 4% hydrochloric acid solution, and crystallizing at 4 deg.C for 8 hr. And (3) carrying out suction filtration on the crystals, separating the crystals from the mother liquor, dissolving the crystals in 3 times of hot water, and carrying out spray drying to obtain the shikimic acid product with the content detected by HPLC: 99.1 percent.
Example 2
Adding pectinase and papain into 100g of the ginkgo leaf extraction waste liquid, wherein the total dosage of the pectinase and the papain is 0.2g, and carrying out enzymolysis at the temperature of 50 ℃ for 1 hour to obtain an enzymolysis liquid; passing the enzymolysis solution through an organic membrane, firstly passing through an organic membrane with a molecular weight of 8000, and then passing through an organic membrane with a molecular weight of 800, and then passing through the organic membrane with a molecular weight of 800, and obtaining decolorized membrane passing liquid, wherein the membrane entering pressure is 1.9 MPa; directly feeding the membrane passing solution into strongly basic anion resin D296 (Tianjin Ministry resin works), eluting and separating with 3 times of column volume of 0.8mol/L formic acid solution, and collecting the eluate when the pH of the eluate is less than 7. The resulting effluent was concentrated under reduced pressure to a solid content of 58% brix in the concentrate, adjusted to PH 1.5 with 4% volume fraction formic acid, and crystallized at 8 ℃ for 10 hours. And (3) carrying out suction filtration on the crystals, separating the crystals from the mother liquor, dissolving the crystals in 4 times of hot water, and carrying out spray drying to obtain the shikimic acid product, wherein the content of the shikimic acid is detected by HPLC: 99.2 percent.
Example 3
Adding pectinase, cellulase and papain into 100g of ginkgo leaf extraction waste liquid, wherein the total dosage of the three enzymes is 0.8g, carrying out enzymolysis for 2 hours at the temperature of 60 ℃ to obtain an enzymolysis liquid, enabling the enzymolysis liquid to pass through an organic membrane, firstly passing through an organic membrane with the molecular weight of 8000, then passing through an organic membrane with the molecular weight of 800, and then passing through the membrane, wherein the membrane pressure is 0.45MPa, so as to obtain a decolorized membrane passing liquid, directly passing through a strongly basic anion resin D201 (Tianjin Ministry resin factory), eluting and separating the membrane passing liquid by using an acetic acid solution with the volume of 6 times of the column volume of 0.1mol/L after the membrane passing liquid is finished, and collecting the solution when the pH of an effluent liquid is less than 7. The resulting effluent was concentrated under reduced pressure to a solid content of 60% brix in the concentrate, adjusted to PH 1.2 with 4% volume fraction acetic acid and crystallized at 10 ℃ for 10 hours. And (3) carrying out suction filtration on the crystals, separating the crystals from the mother liquor, dissolving the crystals in 3 times of hot water, and carrying out spray drying to obtain shikimic acid products with the content of 99.3% by HPLC detection.
Example 4
Adding pectinase, cellulase, papain and amylase into 100g of ginkgo leaf extraction waste liquid, wherein the total amount of the four enzymes is 0.5g, carrying out enzymolysis for 2.5 hours at the temperature of 55 ℃ to obtain an enzymolysis liquid, passing the enzymolysis liquid through an organic membrane, passing through an organic membrane with the molecular weight of 8000, the pressure of the membrane entering is 0.46MPa, passing through an organic membrane with the molecular weight of 800, the pressure of the membrane entering is 2.0MPa, obtaining a decolorized membrane passing liquid, directly passing the membrane passing liquid through strongly basic anion resin D201 (Tianjin Ministry resin factory), eluting and separating by using sulfuric acid solution with the volume of 5 times of the column volume of 1.5mol/L after the membrane passing liquid is finished, and collecting the solution from the pH effluent liquid of less than 7. Concentrating the effluent under reduced pressure until the solid content in the concentrated solution is 70% brix, adjusting the pH value to 1.3 with 4% volume fraction sulfuric acid, and crystallizing at 6 ℃ for 8 hours. And (3) carrying out suction filtration on the crystals, separating the crystals from the mother liquor, dissolving the crystals in 4 times of hot water, and carrying out spray drying, wherein the content of shikimic acid products is 99.4% by HPLC detection.
Example 5
On the basis of the preparation method and the process parameters of the embodiment 1, the step of yeast fermentation is added under the aerobic condition, 0.3g of yeast (purchased from Angel yeast (Chong left) Co., Ltd.) is added to process the filtrate obtained by filtering the organic membrane, the yeast fermentation temperature is 30 ℃, the fermentation time is 36 hours, the obtained fermentation liquor is processed according to the rest steps described in the embodiment 1, and the content of the shikimic acid product is finally 99.6 percent.
Example 6
Adding yeast fermentation step under aerobic condition on the basis of preparation method and process parameters of example 2, adding 1g of yeast (purchased from Angel yeast (Chong left) Co., Ltd.) to process filtrate obtained by organic membrane filtration, wherein the yeast fermentation temperature is 32 ℃, the fermentation time is 40 hours, and treating the obtained fermentation liquor according to the rest steps described in example 2 to finally obtain shikimic acid product with the content of 99.8%.
Example 7
Adding a yeast fermentation step under an aerobic condition on the basis of the preparation method and the process parameters of the embodiment 3, adding 3g of yeast (purchased from Angel yeast (Chong left) Co., Ltd.) to process the filtrate obtained by filtering the organic membrane, wherein the yeast fermentation temperature is 35 ℃, the fermentation time is 48 hours, and treating the obtained fermentation liquor according to the rest steps described in the embodiment 3 to finally obtain the shikimic acid product with the content of 99.9 percent.
The method is simple and convenient to operate, economical and practical, is suitable for popularization, does not need to use an organic solvent, and the obtained shikimic acid has high purity, the mass content of more than 99 percent, snow white appearance and no bitter taste.
Claims (10)
1. A method for preparing shikimic acid from ginkgo leaf extraction waste liquid is characterized by comprising the steps of carrying out enzymolysis on the ginkgo leaf extraction waste liquid, collecting enzymolysis liquid, carrying out organic membrane filtration, anion exchange resin column adsorption elution, concentration, crystallization and drying;
the ginkgo leaf extraction waste liquid is an effluent liquid of a ginkgo leaf extracting solution subjected to macroporous adsorption resin column chromatography, and the ginkgo leaf extracting solution is generated in the process of preparing a ginkgo leaf extract according to 2015 edition Chinese pharmacopoeia;
the biological enzyme used in the enzymolysis process is at least one selected from pectinase, cellulase, papain or amylase.
2. The method for preparing shikimic acid from ginkgo leaf extraction waste liquid according to claim 1, wherein the enzymolysis temperature is 45-60 ℃, and the enzymolysis time is 1-3 hours.
3. The method of claim 2, wherein the amount of the biological enzyme added is one thousandth to eight thousandth of the weight of the waste liquid.
4. The method for preparing shikimic acid from ginkgo leaf extraction waste liquid according to claim 1, wherein the organic membrane filtration step comprises a first filtration and a second filtration, the first filtration uses an organic membrane with a molecular weight cut-off of 8000, and the filtration pressure is 0.45-0.5 MPa; and the second filtration uses an organic membrane with the molecular weight of 800, and the filtration pressure is 1.8-2.0 MPa.
5. The method for preparing shikimic acid from ginkgo leaf extraction waste liquid according to claim 1, wherein the elution solution used in the elution of the anion exchange resin column is 0.1-1.5 mol/L acid solution, the acid solution is one of hydrochloric acid, formic acid, acetic acid or sulfuric acid solution, and the dosage of the elution solution is 3-6 times of the volume of the anion exchange resin column.
6. The method of claim 5, wherein the collection of the eluate is started when the pH of the eluate eluted from the anion exchange resin column is less than 7.
7. The method for preparing shikimic acid from ginkgo leaf extraction waste liquid according to claim 1, wherein the solid content of the concentrated solution obtained in the concentration step is more than 50% brix, and the pH of the concentrated solution is 1.0-1.5.
8. The method for preparing shikimic acid from ginkgo leaf extraction waste liquid according to claim 1, wherein the crystallization temperature in the crystallization step is 4-10 ℃, and the crystallization time is more than 4 hours.
9. The method of claim 1, further comprising a yeast fermentation step before the ion exchange resin adsorption elution step.
10. The method for preparing shikimic acid from the ginkgo leaf extraction waste liquid according to claim 9, wherein the yeast fermentation is aerobic fermentation, the fermentation temperature is 30-35 ℃, the fermentation time is 36-48 hours, and the mass ratio of the ginkgo leaf extraction waste liquid to the yeast is 1: 0.003-1: 0.03.
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112094184B (en) * | 2019-06-17 | 2021-07-13 | 江苏得乐康生物科技有限公司 | Method for extracting shikimic acid from ginkgo leaf extract chromatographic wastewater |
| CN110835297A (en) * | 2019-10-29 | 2020-02-25 | 贵州贝因特生物技术有限公司 | Method for extracting multiple active substances from waste liquid of ginkgo leaf extract production |
| CN111072468A (en) * | 2019-12-25 | 2020-04-28 | 东莞市东阳光生物合成药有限公司 | Method for extracting shikimic acid and shikimic acid extract |
| CN113698289B (en) * | 2020-05-21 | 2024-04-26 | 晨光生物科技集团股份有限公司 | Method for preparing shikimic acid from ginkgo leaf extraction waste liquid |
| CN112390715B (en) * | 2020-11-13 | 2022-10-28 | 晨光生物科技集团股份有限公司 | Method for extracting shikimic acid and quinic acid from ginkgo leaf extract adsorbed lower column water |
| CN112877373B (en) * | 2021-01-26 | 2023-03-21 | 桂林莱茵生物科技股份有限公司 | Preparation method for obtaining gallic acid with content of more than 99% |
| CN113135822B (en) * | 2021-03-15 | 2023-01-31 | 中国林业科学研究院林产化学工业研究所 | Method for efficiently separating shikimic acid from ginkgo leaf extract processing wastewater |
| CN113480420A (en) * | 2021-06-25 | 2021-10-08 | 江苏得乐康生物科技有限公司 | Method for converting organic acid salt in ginkgo leaf extract chromatographic wastewater into organic acid |
| CN113801134B (en) * | 2021-10-28 | 2023-10-03 | 南京久安源环保科技有限公司 | Production process for simultaneously producing bilobalide, ginkgetin, ginkgolic polysaccharide and shikimic acid |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584571A (en) * | 2011-11-21 | 2012-07-18 | 河南孟成生物药业股份有限公司 | Extraction process for shikimic acid in fermentation liquor |
| CN102826994A (en) * | 2012-09-17 | 2012-12-19 | 广西中医药大学 | Preparation method of shikimic acid |
| CN106906251A (en) * | 2017-05-02 | 2017-06-30 | 苏州笃美生物科技有限公司 | A kind of synthetic method of shikimic acid |
| CN107353201A (en) * | 2016-05-09 | 2017-11-17 | 云南希康生物科技有限公司 | A kind of natural shikimic acid extract of high content and preparation method thereof |
-
2018
- 2018-11-22 CN CN201811397363.8A patent/CN109593034B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584571A (en) * | 2011-11-21 | 2012-07-18 | 河南孟成生物药业股份有限公司 | Extraction process for shikimic acid in fermentation liquor |
| CN102826994A (en) * | 2012-09-17 | 2012-12-19 | 广西中医药大学 | Preparation method of shikimic acid |
| CN107353201A (en) * | 2016-05-09 | 2017-11-17 | 云南希康生物科技有限公司 | A kind of natural shikimic acid extract of high content and preparation method thereof |
| CN106906251A (en) * | 2017-05-02 | 2017-06-30 | 苏州笃美生物科技有限公司 | A kind of synthetic method of shikimic acid |
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