CN112538081A - Palmatine derived from cortex Phellodendri salt-roasted product, and its separation and preparation method and application - Google Patents
Palmatine derived from cortex Phellodendri salt-roasted product, and its separation and preparation method and application Download PDFInfo
- Publication number
- CN112538081A CN112538081A CN202011473438.3A CN202011473438A CN112538081A CN 112538081 A CN112538081 A CN 112538081A CN 202011473438 A CN202011473438 A CN 202011473438A CN 112538081 A CN112538081 A CN 112538081A
- Authority
- CN
- China
- Prior art keywords
- palmatine
- preparation
- reference substance
- cortex phellodendri
- mobile phase
- 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.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
A palmatine derived from cortex Phellodendri salt processed product has molecular formula of C20H20NO4Named as palmatine, has the following chemical structural formula:the separation preparation method of the compound comprises the following steps: (1) accurately weighing the palmatine reference substance, putting the palmatine reference substance into an evaporating dish, drying the palmatine reference substance in an oven, taking out the palmatine reference substance, cooling the palmatine reference substance, adding chromatographic grade acetonitrile, and filtering the mixture by using a microporous filter membrane to obtain a dried palmatine sample solution. (2) Separating the baked palmatine sample solution by using a prepared liquid phase, collecting eluent of a target chromatographic peak, and purifying by using a sephadex column; blowing purified eluent with nitrogen, freeze drying to obtain pink powderThe prepared palmatine crystal. The palmatine provided by the invention is a new compound found in phellodendron salt-roasted product decoction pieces for the first time, the separation preparation method has the characteristics of convenience in operation, high efficiency in preparation and the like, the high-purity separation preparation of a large number of palmatine monomers can be realized, and the palmatine compound has a good anti-inflammatory effect on RAW264.7 cells under stimulation of LPS.
Description
Technical Field
The invention relates to the technical field of traditional Chinese medicines, in particular to a compound-palmatine derived from cortex phellodendri salt roasted products, a separation preparation method and application thereof.
Background
The Phellodendron bark is the dry bark of Phellodendron chinense Schneid of Rutaceae, and is a common traditional Chinese medicine for clearing heat and eliminating dampness in clinical practice of traditional Chinese medicine. The processing of phellodendron bark can be traced back to the file method of jin's backup acute prescription' at the earliest time, and then the processing methods of phellodendron bark in ancient medical book include honey-roasting, wine-washing, black-frying, human milk-roasting, salt water-frying and plug skin-removing roasting. The processed products commonly used in pharmacopoeia at present are salt-roasted products and charcoal products.
The main active component of cortex Phellodendri is alkaloid component, which comprises phellodendrine, magnoflorine, berberine, palmatine, jateorhizine, etc. These components have definite activities of anti-inflammation, anticancer, blood sugar reducing, anti-arrhythmia, etc. Because the phellodendron amurense is heated in a certain heating process in the processing process, after part of alkaloid components are heated, because of the unstable heat property, the alkaloid components can be decomposed to generate other components after being heated.
The inventor finds that berberine components of phellodendron amurense can be converted into berberberrubine and jatrorrhizine can be converted into jatrorrhizine in the salt roasting process, and the specific structural change is that methoxyl on 9-bit carbon is removed by heating and is connected with hydroxyl, so that the corresponding erythrosine is generated. The literature reports that the chemical components contained in the phellodendron amurense decoction pieces are isoquinoline berberine type alkaloids, and the isoquinoline berberine type alkaloids with similar structures contained in the phellodendron amurense contain palmatine besides berberine and jateorhizine, so that similar thermal decomposition reactions of the palmatine, the berberine and the jateorhizine are presumed to exist. Therefore, the invention carries out the heating treatment of the simulated processing on the palmatine monomer, and observes the high-performance liquid color of the simulated heated palmatine sampleThe spectrogram discovers that a new chromatographic peak is generated, and the palmatine is supposed to generate decomposition reaction through heating, so that other components are generated. In view of this, the present invention provides palmatine (C)21H22NO4) Separation and preparation method, identification and pharmacodynamic activity research of new components after heating.
Disclosure of Invention
Aiming at the problems, the invention provides the palmatine derived from the cortex phellodendri salt roasted product, and the separation preparation method and the application thereof, the method for separating and preparing the palmatine from the cortex phellodendri salt roasted product has the advantages of high separation efficiency, stable process, simple and convenient operation and low cost, and can realize the separation preparation of a large amount of palmatine monomers with high content and high purity (more than 98%).
In order to achieve the purpose, the invention adopts the following technical scheme.
A palmatine derived from cortex Phellodendri salt processed product has molecular formula of C20H20NO4Named as palmatine, and is separated from the plant for the first time, and has the following chemical structural formula
Further, the method for separating and preparing the palmatine derived from the cortex phellodendri salt roasted product comprises the following steps.
And step 2, separating and preparing the new processed ingredients by simulating the palmatine monomer.
Preparation of liquid chromatography conditions: the mobile phase A is water, wherein each 100mL of water contains 0.3mL of triethylamine, and the mobile phase B is acetonitrile; the volume ratio of the mobile phase A to the mobile phase B is 60-80: 40-20 parts of; the flow rate of the mobile phase is 1 mL/min-1(ii) a By inverting C18The silica gel bonded stationary phase is chromatographic column filler; the column temperature is 35 ℃; the ultraviolet detection wavelength is 220-345 nm; the sample size was 100. mu.L.
Separating the baked palmatine simulated processed sample solution with a preparation liquid phase, collecting the eluate of a target chromatographic peak, and purifying with a sephadex column; and blowing the purified eluent with nitrogen for 20min, and freeze-drying at-80 ℃ to obtain pink powder, namely the separated and prepared palmatine crystals.
Further, the pore size of the filter membrane in the step 1 is 0.22 μm.
Further, the drying temperature in the step 1 is 150-210 ℃, and the drying time is 10-30 min.
Further, the purity of the separated and prepared palmatine is more than 98%.
The palmatine derived from cortex Phellodendri salt preparata product can be used for preparing antiinflammatory medicine.
Compared with the prior art, the invention has the beneficial effects.
The invention provides a palmatine derived from cortex phellodendri salt-roasted products, a separation preparation method and application thereof, the prepared palmatine is a new compound found in cortex phellodendri salt-roasted decoction pieces, the separation method has the characteristics of simple and convenient operation, stable process, low cost and high preparation efficiency, the high-purity (more than 98%) separation preparation of a large amount of palmatine monomers can be realized, and the palmatine compound is proved to have a certain anti-inflammatory effect in an LPS stimulation RAW264.7 cell inflammation model research experiment.
Drawings
FIG. 1 is a chromatogram of the preparative liquid phase of palmatine, wherein peak A is palmatine and peak B is palmatine.
Figure 2 shows the enriched eluate of the compound palmatine after passing through a sephadex column.
FIG. 3 is a representation of palmatine1H-NMR spectrum.
FIG. 4 is a representation of palmatine13C-NMR spectrum.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but it should not be construed that the scope of the above-described subject matter of the present invention is limited to the examples described below, and that all the technologies realized based on the above-described contents of the present invention are within the scope of the present invention.
Example 1.
1. Instruments and materials.
1.1 Instrument: semi-preparative liquid chromatography (Shimadzu LC-10 AT); METTLER TOLEDO switzerland precision analytical balance; AS1610420 tianjin ottesens ultrasonic cleaner; WGL-125B electric heating drying oven; nitrogen blowing instrument (Hengoshu technology development Co., Ltd., Tianjin); vacuum freeze dryer (CHRIST, germany).
1.2 reagent: cortex Phellodendri is purchased from Sichuan New flos Nelumbinis Chinese medicinal decoction pieces GmbH; palmatine reference substance (China pharmaceutical and biological product institute, batch No. 110732-200506; palmatine is self-made by laboratories, HPLC is more than 98%; Sephadex LH-20; methanol analytically pure; acetonitrile, methanol mass spectrometry grade; triethylamine analytically pure; and water purified).
2. A method.
The embodiment provides a method for separating and preparing palmatine from cortex phellodendri salt-roasted products, which comprises the following steps.
And 2, simulating the separation and preparation of the processed product after baking the palmatine monomer, as shown in figure 1.
Preparation of liquid chromatography conditions: the mobile phase A is water, wherein each 100mL of water contains 0.3mL of diethylamine, and B is acetonitrile; the ratio of mobile phase of A to B is (60: 40); the flow rate of the mobile phase is 1 mL/min-1(ii) a By inverting C18The silica gel bonded stationary phase is chromatographic column filler; the column temperature is 35 ℃; the ultraviolet detection wavelength is 345 nm; the sample size was 100. mu.L.
Separating the baked palmatine simulated processed sample solution with a preparation liquid phase, collecting the eluate of a target chromatographic peak, and purifying with a sephadex column; the purified eluate, i.e. palmatine preparation solution, is shown in fig. 2, and is subjected to nitrogen blowing for 20min, and then is subjected to freeze drying at-80 ℃ to obtain pink powder, i.e. separated and prepared palmatine crystals.
3. The identification of the isolated and prepared palmatine compounds is shown in fig. 3 and fig. 4.
Separating the resulting fraction by1H-NMR、13C-NMR analysis identifies the following information:1H-NMR(600MHz,CDCl13-d4)δ:H:7.25(1H,s,H-1),6.76(1H,s,H-4),9.33(1H,s,H-8),6.58(1H,d,J=6.32Hz),7.30(1H,d,J=6.32Hz),7.67(1H,s);13C-NMR(150MHz,CDCl13-d4) Delta. C103.7 (C-1),150.7(C-2),150.8(C-3),110.9(C-4),131.6(C-4a),28.2(C-5),53.6(C-6),146.2(C-8),126.8(C-8a),163.1(C-9),149.2(C-10),117.3(C-11),107.4(C-12),120.3(C-12a),121.3(C-13),133.3(C-13a),120.8(C-1 a). The new ingredient was named palmatine, formula C, because it was structurally characterized and converted from palmatine and was pink in appearance according to the above data and literature20H20NO4. The conversion pathway of palmatine is as follows:
4. pharmacological activity research of palmatine.
In order to further verify the pharmacodynamic action of the novel component palmatine prepared by the invention, the following test for detecting the anti-inflammatory action of the activity of palmatine on RAW264.7 cells stimulated by LPS is provided.
4.1 RAW264.7 proliferation rate determination method under LPS stimulation by palmatine.
After RAW264.7 cells in logarithmic growth phase are digested, scraped and blown, the qualified cell density is adjusted to 2.0 x 10 by using culture solution5A blank control group was prepared by inoculating 100. mu.L/well of each well in a 96-well plate, and leaving 1 well without cell suspension. 37 ℃ and 5% CO2After culturing for 24h under the conditions, the original culture solution is discarded, the serum-free culture solution is replaced, and the cells are starved for 24h to synchronize the cell cycle. Remove serum-free medium, according toThe previous experiment plan added 7 different concentrations of drug-containing culture solution of palmatine, with blank culture solution as control, and each group was set with 3 multiple wells. Each well was 100. mu.L. 4h after drug action, LPS was added to each well at a final concentration of 1. mu.g/mL, except for blank wells. At 37 deg.C, 5% CO2Culturing in an incubator for 20h under the condition, adding 10 μ L of CCK-8 solution into each well, culturing at 37 ℃ for 1h, and measuring OD value at the wavelength of 450nm by using an enzyme-labeling instrument. And calculating the cell proliferation rate.
Cell proliferation rate (%) ═ (OD)Experimental group-ODBlank group)/(ODControl group-ODBlank group)×100%。
4.2 Effect of palmatine on phagocytic Activity of RAW264.7 cells under LPS stimulation.
RAW264.7 cells in logarithmic growth phase are digested, scraped and blown, and the cell density is adjusted to 1 × 106one/mL, and seeded in 96-well culture plates in a volume of 100. mu.L per well. Standing at 37 deg.C for 5% CO2After incubation in the incubator for 24h, the supernatant was discarded. Grouping, blank control group: adding 200 μ L of blank culture solution; model control group: adding 100 mu L of LPS with 2 mu g/mL, and diluting with blank culture solution to obtain a final volume of 200 mu L; administration group: 7 different concentrations of the medicated medium containing palmatine (100. mu.L) and 2. mu.g/mL of LPS (100. mu.L, 1. mu.g/mL final LPS) were added to a final volume of 200. mu.L, each concentration being 3 duplicate wells. 37 ℃ and 5% CO2Culturing for 24 hr in incubator, discarding culture supernatant, adding 0.1% neutral red solution 200 μ L, 37 deg.C, 5% CO2Incubate for 60min, discard neutral red, wash 3 times with pre-warmed PBS, 200 μ L each time, and spin dry. Adding acetic acid-ethanol (1: 1) cell lysis solution 200 μ L/well, standing at 4 deg.C overnight, and measuring OD value at 570nm with microplate reader. And calculating the relative phagocytosis ratio (RSR) of the cells.
Relative cell phagocytosis (%) ═ ODExperimental group-ODBlank group)/(ODControl group-ODBlank group)×100%。
SPSS 16.0 software is adopted for statistical processing, the measured data is expressed by mean plus or minus standard deviation, and t test is adopted for comparison among groups, and P is less than 0.05, so that the statistical significance is achieved.
4.3 the results of the measurements are shown in Table 1.
Table 1. effect of palmatine on proliferation and phagocytosis of RAW264.7 cells under LPS stimulation.
Note: compared with the control group*P<0.05,**P<0.01。
The result shows that the palmatine has a certain anti-inflammatory effect on RAW264.7 cells stimulated by LPS, and the significant difference exists between partial concentration doses and a control group, so that the anti-inflammatory effect of the prepared new component palmatine is significant.
5. And (3) measuring the content of the palmatine and the palmatine in the salted cortex phellodendri.
5.1 preparation of reference solutions of palmatine and palmatine.
Precisely weighing appropriate amount of palmatine and palmatine, placing in a 50mL volumetric flask, dissolving with methanol, and diluting to scale to obtain 0.001275, 0.0029 mg/mL-1And (4) standard solution.
5.2 preparing the test sample.
Taking 50g of clean phellodendron bark decoction pieces from raw phellodendron bark, crushing, and sieving by a 60-mesh sieve.
Taking 50g of clean phellodendron amurense decoction pieces, adding salt water (2 g of salt is used for every 100g of phellodendron amurense), uniformly stirring, covering, moistening, frying in a frying container at 150-160 ℃ for 5min, taking out, cooling, crushing, and sieving with a 60-mesh sieve.
Crushing raw phellodendron and salted phellodendron, sieving with a 60-mesh sieve, precisely weighing 0.2g of the crushed phellodendron and the salted phellodendron respectively, placing the obtained product in a 50mL conical flask with a plug, adding 1% acetic acid methanol solution to a scale mark, weighing the obtained product, carrying out ultrasonic treatment (250W and 40kHz) for 30min, taking out the obtained product, cooling the obtained product, complementing the obtained product with 1% acetic acid-methanol solution for weight loss, shaking up the obtained product, filtering the obtained product, taking a subsequent filtrate, and filtering the obtained product through a 0.22 mu m microporous filter membrane to obtain a.
5.3 results of the experiment.
The results of measurement of an appropriate amount of each sample solution under the following chromatographic conditions are shown in Table 3, wherein,/indicates that the component was not detected.
ACQUITY UPLC BEH C18Chromatography column (2.1 mm. times.100 mm, 1.7 μm); flow rate: 0.25mL min-1; sample introduction amount: 1 mu L of the solution; column temperature: 35 ℃; the mobile phase system is shown in table 2.
Table 2. mobile phase procedure elution table.
Mass spectrum conditions: an electrospray ion source (ESI source) and a positive ion mode scanning mode are adopted; the ion scanning range is m/z 50-1000; capillary ionization voltage: 3.5 kV; source temperature: 150 ℃; desolventizing temperature: 250 ℃; flow rate of desolventizing gas: 800L/h; the assay was performed in multiple reaction monitoring mode (MRM).
TABLE 3 the palmatine and palmatine contents in raw phellodendron bark and salt phellodendron bark.
The result shows that when the raw phellodendron amurense is detected in a UPLC-MSMS mode, only the palmatine component is detected, and the palmatine component is not detected, but both the palmatine component and the palmatine component can be detected in a phellodendron amurense salt-roasted product, and through earlier researches, the palmatine is considered to be converted into the palmatine by heating, and the conversion rate is 25.6% according to experimental data.
Example 2.
The embodiment provides a method for separating and preparing palmatine from cortex phellodendri salt-roasted products, which comprises the following steps.
And 2, separating and preparing a new component of the palmatine monomer baked product.
Preparation of liquid-phase coloursSpectral conditions: the mobile phase A is water, wherein each 100mL of water contains 0.3mL of diethylamine, and B is acetonitrile; the ratio of mobile phase of A to B is (70: 30); flow rate of mobile phase 1 mL/min-1(ii) a By inverting C18The silica gel bonded stationary phase is chromatographic column filler; the column temperature is 30 ℃; the ultraviolet detection wavelength is 210 nm; the sample size was 100. mu.L.
Separating the baked palmatine reference substance solution with a preparation liquid phase, collecting eluate of a target chromatographic peak, and purifying with a sephadex column; and blowing the purified eluent with nitrogen for 10min, and freeze-drying at-80 ℃ to obtain pink powder, namely the separated and prepared palmatine crystals.
Example 3.
The embodiment provides a method for separating and preparing palmatine from cortex phellodendri salt-roasted products, which comprises the following steps.
And 2, separating and preparing a new component of the palmatine monomer baked product.
Preparation of liquid chromatography conditions: the mobile phase A is water, wherein each 100mL of water contains 0.2mL of triethylamine, and the mobile phase B is acetonitrile; the ratio of mobile phase of A to B is (60: 40); the mobile phase flow rate is 1 mL/min-1(ii) a By inverting C18The silica gel bonded stationary phase is chromatographic column filler; the column temperature is 25 ℃; the ultraviolet detection wavelength is 310 nm; the sample size was 100. mu.L.
Separating the baked palmatine simulated processed sample solution with a preparation liquid phase, collecting the eluate of a target chromatographic peak, and purifying with a sephadex column; and blowing the purified eluent with nitrogen for 20min, and freeze-drying at-80 ℃ to obtain pink powder, namely the separated and prepared palmatine crystals.
Claims (6)
2. The method for separating and preparing palmatine derived from cortex Phellodendri and Sal preparata as claimed in claim 1, comprising the steps of:
step 1, simulation processing of palmatine: accurately weighing a palmatine reference substance, drying the palmatine reference substance in an evaporating dish, taking out and cooling, adding an appropriate amount of acetonitrile, and filtering with a microporous filter membrane to obtain a dried palmatine simulated processing sample solution;
step 2, separating and preparing new processed ingredients by simulating palmatine monomers:
preparation of liquid chromatography conditions: the mobile phase A is water, wherein each 100mL of water contains 0.3mL of triethylamine, and the mobile phase B is acetonitrile; the volume ratio of the mobile phase A to the mobile phase B is 60-80: 40-20 parts of; flow rate of mobile phase 1 mL/min-1(ii) a By inverting C18The silica gel bonded stationary phase is chromatographic column filler; the column temperature is 35 ℃; the ultraviolet detection wavelength is 220-345 nm; the sample injection amount is 100 mu L;
separating the baked palmatine simulated processed sample solution with a preparation liquid phase, collecting the eluate of a target chromatographic peak, and purifying with a sephadex column; and blowing the purified eluent with nitrogen for 20min, and freeze-drying at-80 ℃ to obtain pink powder, namely the separated and prepared palmatine crystals.
3. The separation preparation method of claim 2, wherein the pore size of the filter membrane in the step 1 is 0.22 μm.
4. The separation preparation method according to claim 2, wherein the baking temperature in step 1 is 150 to 210 ℃ and the baking time is 10 to 30 min.
5. The isolated preparation method according to claim 2, wherein the purity of the isolated and prepared palmatine is 98% or more.
6. The use of palmatine derived from cortex Phellodendri and Sal preparata as claimed in claim 1 in the preparation of antiinflammatory medicine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011473438.3A CN112538081A (en) | 2020-12-15 | 2020-12-15 | Palmatine derived from cortex Phellodendri salt-roasted product, and its separation and preparation method and application |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011473438.3A CN112538081A (en) | 2020-12-15 | 2020-12-15 | Palmatine derived from cortex Phellodendri salt-roasted product, and its separation and preparation method and application |
Publications (1)
Publication Number | Publication Date |
---|---|
CN112538081A true CN112538081A (en) | 2021-03-23 |
Family
ID=75018726
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202011473438.3A Pending CN112538081A (en) | 2020-12-15 | 2020-12-15 | Palmatine derived from cortex Phellodendri salt-roasted product, and its separation and preparation method and application |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN112538081A (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105418601A (en) * | 2014-09-17 | 2016-03-23 | 成都贝斯凯瑞生物科技有限公司 | Tetrahydrocoptisine derivative and applications thereof |
CN105503857A (en) * | 2015-12-30 | 2016-04-20 | 吉林农业大学 | Palmatine derivatives and application thereof to preparation of anti-alzheimer-disease medicament |
CN110191710A (en) * | 2017-01-19 | 2019-08-30 | 安成生物科技股份有限公司 | For preventing or treating the dermopathic method of immunoinflammatory and pharmaceutical composition |
-
2020
- 2020-12-15 CN CN202011473438.3A patent/CN112538081A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105418601A (en) * | 2014-09-17 | 2016-03-23 | 成都贝斯凯瑞生物科技有限公司 | Tetrahydrocoptisine derivative and applications thereof |
CN105503857A (en) * | 2015-12-30 | 2016-04-20 | 吉林农业大学 | Palmatine derivatives and application thereof to preparation of anti-alzheimer-disease medicament |
CN110191710A (en) * | 2017-01-19 | 2019-08-30 | 安成生物科技股份有限公司 | For preventing or treating the dermopathic method of immunoinflammatory and pharmaceutical composition |
Non-Patent Citations (2)
Title |
---|
吕子明等: ""9-O-烃基取代巴马亭衍生物的合成和结构表征"", 《中国中药杂志》 * |
周元瑶等: ""十五种原小檗碱型季按生物碱高效液相色谱条件的优选"", 《药学学报》 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109692131B (en) | Preparation method of ceramide extract in sapindaceae plant seeds and product | |
CN101843884B (en) | Method for testing quality of antiviral oral liquid for treating hand-foot-and-mouth disease | |
CN109655558B (en) | Method for detecting effective part group of periploca forrestii schltr | |
CN102641328A (en) | Malaytea scurfpea fruit extract, as well as preparation and application methods thereof | |
CN104958330A (en) | Oroxylum indicum general flavone extraction and purification method and application thereof | |
CN112538081A (en) | Palmatine derived from cortex Phellodendri salt-roasted product, and its separation and preparation method and application | |
CN114957497B (en) | Gentiana rigescens acidic polysaccharide and preparation method and application thereof | |
CN105541831B (en) | Medicine root berberrubine derived from amur cork-tree processed product and separation preparation method and application thereof | |
CN102772501A (en) | Rheum emodi Wall. extract and its preparing method | |
CN107589213A (en) | A kind of toad skin medicinal material or medicine materical crude slice or the method for quality control for including toad leather agent | |
CN110687219B (en) | Detection method of suhuang cough-relieving capsule fingerprint and application thereof | |
CN103405664B (en) | Daochi powder formula granule as well as preparation method, use and detection method thereof | |
CN108245561B (en) | Charred fructus crataegi, its preparation method and quality detection method | |
CN107050010A (en) | Application of the Cichoric acid in the medicine of anti respiratory syncytial virus is prepared | |
CN102204945A (en) | Extraction method of herba cirsii japonici carbonisatum general flavone liquid | |
Du et al. | UPLC-MS based metabolite profiles of two major bioactive components in herb pair scutellaria–coptis metabolized by intestinal bacteria derived from healthy rats and rats with type 2 diabetes | |
CN107260810A (en) | The Preparation method and use of high-purity clove leaf total iridoid glycoside extract and its preparation | |
CN102526561B (en) | Detection method for Sanjin preparation | |
CN110596263A (en) | Establishing method of moringa oleifera extract fingerprint and fingerprint thereof | |
CN113702520B (en) | Method for controlling quality of long pepper medicinal material | |
CN110613741B (en) | Anti-inflammatory active extract of achyranthes aspera and preparation method thereof | |
CN108685930B (en) | Application of aralia elata saponin IV | |
Li et al. | Thin-layer chromatographic quantification of three alkaloid compounds in Sophora alopecuroides and TLC—bioautography for screening antioxidant components | |
CN105687254A (en) | A method of extracting anti-lung-cancer active components from armillaria luteo-virens and applications of the active components | |
CN105601692A (en) | Extraction method and application of ergosterol monomer compound in Armillarialuteo-virens |
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 | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210323 |
|
RJ01 | Rejection of invention patent application after publication |