CN110818585A - Separation method for simultaneously preparing five dopamine compounds from aspongopus - Google Patents
Separation method for simultaneously preparing five dopamine compounds from aspongopus Download PDFInfo
- Publication number
- CN110818585A CN110818585A CN201911098424.5A CN201911098424A CN110818585A CN 110818585 A CN110818585 A CN 110818585A CN 201911098424 A CN201911098424 A CN 201911098424A CN 110818585 A CN110818585 A CN 110818585A
- Authority
- CN
- China
- Prior art keywords
- aspongopus
- solution
- dihydroxyphenyl
- methanol
- dopamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
A separation method for simultaneously preparing five dopamine compounds from aspongopus belongs to the technical field of separation and purification of compound monomers. The method takes dry aspongopus as a raw material, and obtains five dopamine compound monomers simultaneously through the steps of ethanol extraction, vacuum concentration, step-by-step extraction, silica gel column enrichment and elution, high performance preparative liquid chromatography separation and product recovery; lays a foundation for further researching the medicinal value of the aspongopus medicinal material and the synthesis and development of new medicines, and is also beneficial to the development and utilization of traditional aspongopus resources.
Description
Technical Field
The invention relates to a method for separating and purifying animal compound monomers, in particular to a separation method for simultaneously preparing five dopamine compounds from aspongopus, and belongs to the technical field of traditional Chinese medicines.
Background
The product is Aspongopus of OrchidaceaeCotidius chinensisThe dried bodies of Dallas, also known as flatus, etc., are distributed in most areas and parts of south Asia countries in south China. Aspongopus, a medicinal and edible insect, was first recorded in Bencao gang mu (compendium of materia Medica), is a traditional Chinese medicine recorded in 2015 edition Chinese pharmacopoeia, has the effects of regulating qi-flowing, relieving pain, warming middle-jiao and tonifying yang, and can be drunk after being soaked in wineTreat deficiency of spleen and kidney and deficiency of primordial yang. The national researchers think that the aspongopus has the effects of resisting bacteria, resisting blood coagulation and dissolving thrombus and has a certain inhibiting effect on cancer cells, but the effective components of the aspongopus are definitely identified, and most of the effective components are reported about fatty acids, nucleosides, proteins, polypeptides and other substances. Many active ingredients remain to be identified.
The national intellectual property office 2014 4/16 discloses a dopamine compound monomer named aspongopus amide A with the publication number of CN 103724318A and the patent name of 'aspongopus amide A and a composition thereof and application thereof in pharmacy and food', and the dopamine compound monomer is prepared and has good curative effect in the aspect of medicines for treating nephropathy and chronic nephropathy. The aspongopus is also used as a raw material, but only one dopamine compound monomer is obtained, so that the technical scheme is complex, the types of related solvents are too many, the yield is low, and further intensive research cannot be carried out.
Disclosure of Invention
The invention aims to provide a separation method for simultaneously preparing five dopamine compounds from aspongopus, lays a foundation for further researching the relation between an active substance of the aspongopus and a treatment effect, and is also beneficial to development and utilization of a traditional Chinese medicinal material resource of the aspongopus. The invention separates five high-purity compound monomer components from aspongopus simultaneously through reasonable process routes and parameter conditions, and the purity of the monomer components reaches more than 98.0 percent.
In order to achieve the technical purpose, the following technical scheme is proposed:
a separation method for simultaneously preparing five dopamine compounds from aspongopus comprises the following steps:
the method comprises the following steps: pulverizing dried Aspongopus into 1-5mm coarse powder, adding 2-10 times of 70% ethanol solution according to weight ratio, ultrasonic extracting for 3 times for 60min, 45min, and 30min respectively, mixing extractive solutions, filtering, and vacuum concentrating at 60 deg.C to no alcohol degree to obtain Aspongopus extract concentrate;
step two: sequentially adding petroleum ether, ethyl acetate and n-butanol into the concentrated solution obtained in the first step for extraction, extracting with each solvent for 3 times, wherein the volume of each solvent is 1/3-2/3 of the volume of the solution, collecting and combining n-butanol extract, and vacuum concentrating at 60 ℃ to 1/10 volumes;
step three: adding 1-3 times of 100-mesh silica gel into the concentrated solution obtained in the second step according to the weight ratio, mixing the mixture with a sample, performing silica gel column chromatography, performing gradient elution by using chloroform-methanol, collecting 1/5-1/1 elution fraction, and performing vacuum concentration at 60 ℃ to 1/10-1/5 volume to obtain a solution to be prepared;
step four: filtering the solution to be prepared obtained in the step three by using a 0.45-micrometer organic membrane, collecting filtrate, then injecting the filtrate, preparing and separating 5 types of monomeric compounds of the aspongopus, and pertinently collecting the preparation fraction solution of each monomer with the purity of more than 98.0%; in the process, the wavelength of the ultraviolet detector is set to be 280nm, and online detection is carried out;
step five: respectively concentrating the 5 prepared fraction solutions obtained by the high performance preparative liquid chromatography in the step (4) at 60 ℃ in vacuum to dryness, recovering the methanol solvent, and drying the solid in a drying oven at 65 ℃ for 12 hours to obtain the final product
（1）N-[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]acetamide；
（2）N-[(E)-2-(3,4-Dihydroxyphenyl)vinyl]acetamide；
（3）trans-2-(3',4'-Dihydroxyphenyl)-3-acetylamino-7-hydroxyethyl-1,4-benzodioxane；
（4）trans-2-(3',4'-Dihydroxyphenyl)-3-acetylamino-6-hydroxyethyl-1,4-benzodioxane；
(5) trans-2- (3',4' -Dihydroxyphenyl) -3-acetylamino-7- (N-acetyl-2' -aminoethyl-ene)1, 4-benzodioxane; five high-purity compound monomers.
In the fourth step, the conditions of the preparative liquid chromatography are as follows: the diameter of the chromatographic column is: 50mm, the chromatographic column filler is C18 filler, the particle size is 10 μm, the column temperature is room temperature, the mobile phase is methanol-0.1% acetic acid water solution, and the volume ratio of the two is 40: 60, the flow rate is 60ml/min, and the detection wavelength is 280 nm.
The purity rechecking of the five monomer compound products adopts reversed-phase analysis type high performance liquid chromatography, and the chromatographic conditions are as follows: c18 is used as a filler, the particle size is 5 mu m, methanol-0.1% acetic acid aqueous solution is used as a mobile phase, and the volume ratio of the two is 40: 60, the flow rate is 1.0ml/min, and the detection wavelength is 280 nm.
The purity of the five monomer compound products obtained by simultaneous separation respectively reaches 98.0%.
The beneficial effect of adopting above-mentioned technical scheme is:
1. according to the invention, through reasonable process steps and parameter conditions, five compound monomers are obtained at one time, the obtained compound quantity is large, and the effective ingredients of the aspongopus are fully explored;
2. the method has the advantages of simple and convenient process route, strong operability and high separation efficiency, and the obtained monomer compounds have high purity which is more than 98.0 percent and can be used for other subsequent experiments;
3. aiming at the physicochemical properties of various components in the aspongopus, the technical scheme effectively provides the components containing dopamine components through proper sequence collocation and proper parameter combination, and removes a large amount of impurities, so that a sample solution which can enter a preparative high performance liquid chromatography system is obtained, the high performance liquid chromatograph is not greatly influenced, the service cycle of the instrument is prolonged as much as possible, and the production cost is saved;
4. in the second step of the invention, petroleum ether and ethyl acetate are used for extraction to remove a large amount of medium and small polar impurities, so that the total amount of the sample and the interference of the impurities are less during preparation;
5. according to the invention, the silica gel column chromatography is subjected to gradient elution by using chloroform-methanol, so that the dopamine compound component can be enriched, unnecessary impurity components can be further removed, and the sample loading amount of the prepared liquid chromatography is reduced;
6. the organic reagents used in each step of the invention can be recycled, the solvent consumption is low, the cost is saved, and the environmental pollution is reduced.
Drawings
FIG. 1 shows the structures of dopamine compounds I to V of the present invention.
Detailed Description
In the following, the technical solutions in the embodiments of the present invention are clearly and completely described, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
1. pulverizing dried Aspongopus 1Kg into 1-5mm coarse powder, adding 70% ethanol solution 5L, ultrasonic extracting for 3 times with ultrasonic frequency for 60min, 45min, 30min, mixing extractive solutions 15L, filtering, and vacuum concentrating at 60 deg.C to obtain 2L solution with no purity. Sequentially adding petroleum ether, ethyl acetate and n-butanol 800ml respectively, extracting with each solvent for 3 times, mixing n-butanol solutions, vacuum concentrating to 200ml at 60 deg.C, adding 200g of 200 mesh silica gel, mixing, performing silica gel column chromatography, performing chloroform-methanol gradient elution, collecting 1/5-1/1 eluate fraction, concentrating to 100ml, adding 50ml of methanol, and filtering with 0.45 μm organic membrane; injecting a sample into the filtrate, preparing and separating compound monomers, collecting components with the concentration of more than 98.0% in a targeted manner, combining the same fractions, and setting the detection wavelength of an ultraviolet detector to be 280nm in the process to obtain compounds I to V:
2. structural identification of compounds one to five;
by means of mass spectrometry,1H-NMR、13C-NMR and other spectrum means determine the chemical structures of the compounds from one to five.
（1）N-[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]acetamide；
Light yellow powder; c10H13NO4，ESI-MS：[M+H]+=212,[M+Na]+=234,[2M+H]+=445;[M-H]-=210,[2M-H]-=421, molecular weight is 211;1H NMR (400 MHz, Methanol-d 4) δ 6.93 – 6.46 (m, 3H),4.56 (dd,J= 7.9, 4.9 Hz, 1H), 3.38 – 3.33 (m, 1H), 3.26 (d,J= 5.5 Hz,1H), 1.91 (s, 3H).13C NMR (101 MHz, Methanol-d 4) δ 173.61 , 146.24 , 145.89 ,132.10 , 118.68 , 116.09 , 114.34 , 73.31 , 48.20 , 22.52 。
（2）O-[(E)-2-(3,4-Dihydroxyphenyl)vinyl]acetamide；
light yellow powder; c10H11NO3，ESI-MS：[M+H]+=194,[M+Na]+=216;[M-H]-=192,[2M-H]-=385, molecular weight 193;1H NMR (400 MHz, Methanol-d 4) δ 7.19 (d,J= 14.7 Hz, 1H), 6.76(d,J= 1.9 Hz, 1H), 6.66 (d,J= 8.2 Hz, 1H), 6.60 (dd,J= 8.2, 1.9 Hz,1H), 6.04 (d,J= 14.7 Hz, 1H), 2.00 (s, 3H).
13C NMR (101 MHz, Methanol-d 4) δ 170.63 , 146.64 , 145.77 , 129.95 ,121.64 , 119.07 , 116.65 , 115.07 , 113.17 , 22.69。
（3）trans-2-(3',4'-Dihydroxyphenyl)-3-acetylamino-7-hydroxyethyl-1,4-benzodioxane；
light yellow powder; c20H22N2O6，ESI-MS：[M+H]+=387,[M+Na]+=409,[M+K]+=425,[2M+H]+=773;[M-H]-=385,[2M-H]-=771, molecular weight 386;
1H NMR (400 MHz, Methanol-d 4) δ 6.86 – 6.67 (m, 6H), 5.65 (d,J= 7.1 Hz,1H), 4.67 (d,J= 7.1 Hz, 1H), 3.36 – 3.31 (m, 2H), 2.68 (d,J= 7.3 Hz, 2H),1.88 (s, 3H), 1.85 (3, 1H).13C NMR (101 MHz, Methanol-d 4) δ 173.21 , 147.13 ,146.45 , 144.30 , 142.17 , 134.14 , 128.79 , 123.20 , 120.58 , 118.07 ,117.94 , 116.11 , 115.56 , 78.29 , 78.25 , 42.15 , 35.78 , 22.58 , 22.53。
（4）trans-2-(3',4'-Dihydroxyphenyl)-3-acetylamino-6-hydroxyethyl-1,4-benzodioxane；
light yellow powder; c20H22N2O6，ESI-MS：[M+H]+=387,[M+Na]+=409,[M+K]+=425,[2M+H]+=773,[2M+Na]+=795;[M-H]-=385,[2M-H]-=771, molecular weight 386;1H NMR (400 MHz, Methanol-d 4)δ 7.03 – 6.53 (m, 6H), 5.69 (d,J= 7.2 Hz, 1H), 4.68 (d,J= 7.2 Hz, 1H),3.42 – 3.34 (m, 2H), 2.70 (t,J= 7.3 Hz, 2H), 1.91 (s, 3H), 1.88 (s, 3H).
13C NMR (101 MHz, Methanol-d 4) δ 173.21 , 147.12 , 146.44 ,143.52 , 142.98, 134.28 , 128.80 , 123.04 , 120.60 , 118.16 , 117.85 , 116.10 , 115.56 ,78.32 , 78.22 , 42.14 , 35.76 , 22.59 , 22.53 。
（5）trans-2-(3',4'-Dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2''-aminoethyl-ene)1,4-benzodioxane；
light yellow powder; c20H20N2O6，ESI-MS：[M+H]+=385,[M+Na]+=407,[2M+H]+=769,[2M+Na]+=791;[M-H]-=383,[2M-H]-=767
1H NMR (400 MHz, Methanol-d 4) δ 7.27 (d,J= 14.7 Hz, 1H), 6.94 – 6.57(m, 6H), 6.07 (d,J= 14.7 Hz, 1H), 5.65 (d,J= 7.2 Hz, 1H), 4.67 (d,J=7.2 Hz, 1H), 2.00 (s, 3H), 1.91 (s, 3H).
13C NMR (101 MHz, Methanol-d 4) δ 173.37 , 170.78 , 147.32 , 146.62 ,144.72 , 142.74 , 132.04 , 128.86 , 123.04 , 120.74 , 120.45 , 118.39 ,116.30 , 115.74 , 114.83 , 114.10 , 78.53 , 78.48 , 22.75 , 22.73。
Claims (4)
1. A separation method for simultaneously preparing five dopamine compounds from aspongopus is characterized in that: it comprises the following steps:
the method comprises the following steps: pulverizing dried Aspongopus into 1-5mm coarse powder, adding 2-10 times of 70% ethanol solution according to weight ratio, ultrasonic extracting for 3 times for 60min, 45min, and 30min respectively, mixing extractive solutions, filtering, and vacuum concentrating at 60 deg.C to no alcohol degree to obtain Aspongopus extract concentrate;
step two: sequentially adding petroleum ether, ethyl acetate and n-butanol into the concentrated solution obtained in the first step for extraction, extracting with each solvent for 3 times, wherein the volume of each solvent is 1/3-2/3 of the volume of the solution, collecting and combining n-butanol extract, and vacuum concentrating at 60 ℃ to 1/10 volumes;
step three: adding 1-3 times of 100-mesh silica gel into the concentrated solution obtained in the second step according to the weight ratio, mixing the mixture with a sample, performing silica gel column chromatography, performing gradient elution by using chloroform-methanol, collecting 1/5-1/1 elution fraction, and performing vacuum concentration at 60 ℃ to 1/10-1/5 volume to obtain a solution to be prepared;
step four: filtering the solution to be prepared obtained in the step three by using a 0.45-micrometer organic membrane, collecting filtrate, then injecting the filtrate, preparing and separating 5 types of monomeric compounds of the aspongopus, and pertinently collecting the preparation fraction solution of each monomer with the purity of more than 98.0%; in the process, the wavelength of the ultraviolet detector is set to be 280nm, and online detection is carried out;
step five: respectively concentrating the 5 prepared fraction solutions obtained by the high performance preparative liquid chromatography in the step (4) at 60 ℃ in vacuum to dryness, recovering the methanol solvent, and drying the solid in a drying oven at 65 ℃ for 12 hours to obtain the final product
（1）N-[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]acetamide；
（2）N-[(E)-2-(3,4-Dihydroxyphenyl)vinyl]acetamide；
（3）trans-2-(3',4'-Dihydroxyphenyl)-3-acetylamino-7-hydroxyethyl-1,4-benzodioxane；
（4）trans-2-(3',4'-Dihydroxyphenyl)-3-acetylamino-6-hydroxyethyl-1,4-benzodioxane；
(5) trans-2- (3',4' -Dihydroxyphenyl) -3-acetylamino-7- (N-acetyl-2' -aminoethyl-ene)1, 4-benzodioxane; five high-purity compound monomers.
2. The separation method for simultaneously preparing five dopamine compounds from aspongopus according to claim 1, characterized in that: in the fourth step, the conditions of the preparative liquid chromatography are as follows: the diameter of the chromatographic column is: 50mm, the chromatographic column filler is C18 filler, the particle size is 10 μm, the column temperature is room temperature, the mobile phase is methanol-0.1% acetic acid water solution, and the volume ratio of the two is 40: 60, the flow rate is 60ml/min, and the detection wavelength is 280 nm.
3. The separation method for simultaneously preparing five dopamine compounds from aspongopus according to claim 1, characterized in that: the purity rechecking of the five monomer compound products adopts reversed-phase analysis type high performance liquid chromatography, and the chromatographic conditions are as follows: c18 is used as a filler, the particle size is 5 mu m, methanol-0.1% acetic acid aqueous solution is used as a mobile phase, and the volume ratio of the two is 40: 60, the flow rate is 1.0ml/min, and the detection wavelength is 280 nm.
4. The isolation method for simultaneously preparing 5 dopamine compounds from aspongopus according to claim 1, wherein: the purity of the five monomer compound products obtained by simultaneous separation respectively reaches 98.0%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911098424.5A CN110818585B (en) | 2019-11-12 | 2019-11-12 | Separation method for simultaneously preparing five dopamine compounds from aspongopus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911098424.5A CN110818585B (en) | 2019-11-12 | 2019-11-12 | Separation method for simultaneously preparing five dopamine compounds from aspongopus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110818585A true CN110818585A (en) | 2020-02-21 |
| CN110818585B CN110818585B (en) | 2023-05-30 |
Family
ID=69554142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911098424.5A Active CN110818585B (en) | 2019-11-12 | 2019-11-12 | Separation method for simultaneously preparing five dopamine compounds from aspongopus |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110818585B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111320602A (en) * | 2020-03-23 | 2020-06-23 | 遵义医科大学 | Preparation method of aspongopus dopamine novel compound and application of aspongopus dopamine compound in preventing testicular cell damage |
| CN115078588A (en) * | 2022-07-14 | 2022-09-20 | 江阴天江药业有限公司 | Aspongopus and quality evaluation method of processed product thereof |
| CN115403550A (en) * | 2022-08-12 | 2022-11-29 | 暨南大学 | Preparation and analysis method of honeycomb active ingredient |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102285958A (en) * | 2011-04-21 | 2011-12-21 | 李国玉 | Dopamine polymer as well as derivative, preparation method and medicinal purpose thereof |
-
2019
- 2019-11-12 CN CN201911098424.5A patent/CN110818585B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102285958A (en) * | 2011-04-21 | 2011-12-21 | 李国玉 | Dopamine polymer as well as derivative, preparation method and medicinal purpose thereof |
Non-Patent Citations (2)
| Title |
|---|
| MANICKAM SUGUMARAN等: "Compounds from the insect Blaps japanensis with COX-1 and COX-2 inhibitory activities", 《INSECT BIOCHEMISTRY AND MOLECULAR BIOLOGY》 * |
| YONG-MING YAN: "Compounds from the insect Blaps japanensis with COX-1 and COX-2 inhibitory activities", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111320602A (en) * | 2020-03-23 | 2020-06-23 | 遵义医科大学 | Preparation method of aspongopus dopamine novel compound and application of aspongopus dopamine compound in preventing testicular cell damage |
| CN111320602B (en) * | 2020-03-23 | 2023-07-07 | 遵义医科大学 | Preparation method of aspongopus dopamine compound and application of aspongopus dopamine compound in resisting testis cell injury |
| CN115078588A (en) * | 2022-07-14 | 2022-09-20 | 江阴天江药业有限公司 | Aspongopus and quality evaluation method of processed product thereof |
| CN115403550A (en) * | 2022-08-12 | 2022-11-29 | 暨南大学 | Preparation and analysis method of honeycomb active ingredient |
| CN115403550B (en) * | 2022-08-12 | 2024-01-23 | 暨南大学 | Preparation and analysis method of active ingredients of nidus Vespae |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110818585B (en) | 2023-05-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102976909B (en) | Method for extracting and purifying 6-gingerol from ginger | |
| CN110818585B (en) | Separation method for simultaneously preparing five dopamine compounds from aspongopus | |
| CN102040520B (en) | Method for separating and purifying chlorogenic acid from eucommia bark leaves | |
| CN105294628A (en) | Method for preparing flavonoid component by separating wild chrysanthemum flower | |
| CN106083985A (en) | A kind of method that membrance separation is combined isolated and purified tea saponin with macroporous resin | |
| WO2021042922A1 (en) | Preparation method for tetragalloylglucose | |
| CN105131062B (en) | A kind of preparation method of Baical Skullcap root P.E | |
| CN102228515B (en) | Separation and enrichment method of total flavones and total alkaloids of Lotus Plumule | |
| CN113773184A (en) | Method for extracting curcumin compound | |
| CN112266399B (en) | High-purity separation and extraction method of epimedium extract | |
| WO2012061984A1 (en) | Method for preparing albiflorin and paeoniflorin | |
| CN104193758B (en) | A kind of preparation method who extracts wedelolactone class monomeric compound from eclipta | |
| CN115010618A (en) | Separation and purification method of aureoyl amide alcohol ester capable of reducing uric acid and application thereof | |
| CN108794551A (en) | A method of preparing high-purity gardenoside from gardenia yellow pigment waste liquor | |
| CN107353296B (en) | A method of extracting activated protein and eurycomanone from Tongkat Ali | |
| CN102399252A (en) | Preparation method for cowherb seed flavonoid glycoside monomer | |
| CN112043738A (en) | Preparation method of radix angelicae pubescentis active ingredient extract | |
| CN110772549A (en) | Preparation method of brucea javanica total antitumor new component | |
| CN112661799B (en) | Method for separating and purifying protopteridoside in pteridophyte | |
| CN108383884B (en) | Separation and purification method of unstable crocin | |
| CN107812021A (en) | A kind of method that saikoside is extracted from radix bupleuri | |
| CN104945462A (en) | Purification method of maytenfolic acid | |
| CN102429965A (en) | Method for preparing active ingredients in tree peony bark | |
| CN108329367A (en) | A method of preparing Specnuezhenide from the fruit of glossy privet | |
| CN102531881A (en) | Separating and purifying method for roburic acid monomer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |