CN105693714B - The method of alkaloid compound in pH zone refining countercurrent separation leatherleaf mahonia - Google Patents
The method of alkaloid compound in pH zone refining countercurrent separation leatherleaf mahonia Download PDFInfo
- Publication number
- CN105693714B CN105693714B CN201610133908.9A CN201610133908A CN105693714B CN 105693714 B CN105693714 B CN 105693714B CN 201610133908 A CN201610133908 A CN 201610133908A CN 105693714 B CN105693714 B CN 105693714B
- Authority
- CN
- China
- Prior art keywords
- phase
- leatherleaf mahonia
- alkaloid
- zone refining
- separation
- 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.)
- Active
Links
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses the method for alkaloid compound in a kind of pH zone refining countercurrent separation leatherleaf mahonia, used condition is in described separation：Solvent system is chloroform：Methanol：Water=3.5 4.5:2.5‑3.5:2.5 3.5, pH zone refining countercurrent instrument column volume are 200 400, the 5g of applied sample amount 2, the 1000rpm of rotating speed 300, and upper phase is stationary phase, and lower phase is mobile phase, the mL/min of flow velocity 1.5 2.5, stationary phase retention rate 35.71%, the 260nm of Detection wavelength 250.The method of the present invention prepares cost and is less than prior art, it is easy to operate, efficiency high, can be compared with high-volume therefrom medicine leatherleaf mahonia, jateorrhizine of the purity more than 96%, jamaicin, palmatine, the method for separating and preparing of jateorrhizine monomeric compound are prepared in separation, and the present invention isolates jateorrhizine from Chinese medicine leatherleaf mahonia first.
Description
Technical field
The present invention relates to a kind of isolation and purification method of effective component of chinese medicine, specially application pH- zone refines adverse current color
The method of alkaloid compound (jateorrhizine, jamaicin, jateorrhizine, palmatine monomer) in spectrum separation leatherleaf mahonia.
Background technology
Leatherleaf mahonia is Berberidaceae plant mahonia bealei Mahoniabealei (Fort.) Carr or mahonia fortuneiFedde
Mahoniafortunei (Lindl.) Fedde drying stem, its is bitter in taste, trembles with fear, the effect of with heat-clearing and damp-drying drug, purging intense heat and detonicating.
Cure mainly damp-heat dysentery, jaundice, red eye, swell pain, gastropyretic toothache, boil carbuncle swells.Alkaloid compound is mainly in leatherleaf mahonia
Isoquinoline alkaloid, including jateorrhizine, palmatine and jamaicin, result of study show that isoquinoline alkaloid can suppress certainly
By base and lipoxygenase activity so as to reach the effect of anti-inflammatory.In addition, the oxidation resistance of alkaloid also with its disease resistance, degeneration-resistant
Property and anti-aging are relevant.Modern pharmacological research shows that leatherleaf mahonia also has the effect of certain reversing tumor cells resistance.
It is existing mainly to use silica gel repeatedly on the literature method that in leatherleaf mahonia prepared by the separation of alkaloids monomeric compound
Column chromatography and Sephadex LH-20 gel column chromatographies, its limitation be waste time and energy, to pollute environment, sample purity low, and
Column chromatography has irreversibility suction-operated to sample repeatedly, and isolated alkaloid monomer preparation efficiency is low, cost is higher, it is difficult to
Develop into the big isolation technics of preparation amount.
High speed adverse current chromatogram (High-speed Counter-current Chromatography, HSCCC) is nearly 30 years
A kind of efficient, the quick liquid liquid partition chromatography isolation technics continuously without any solid support grown up, it keeps away
Solid state adhesion body or the next sample of belt carrier are exempted from easily by various problems such as dead absorption, loss and denaturation.The refined adverse current of pH- zone
Chromatogram (pH-Zone-Refining Countercurrent Chromatography) is then in common high speed adverse current chromatogram
On the basis of instrument, by the allotment of the composition to the solvent system used in separation sample, using the means of chemistry, make sample sets
The chromatographic separation process divided adds the feature assembled by pH zone, meanwhile, the elution process of component is shown as similar displacement
The elution process of (replacement) chromatogram (Displacement Chromatography), therefore, its chromatogram are no longer Gausses point
The chromatographic peak profile series of cloth, and turn into by the precipitous rectangle region band series in the border of the big minispread of pH value, the result is that can handle
The separation preparation amount of the adverse current chromatogram instrument of same volume improves several times or even ten times.
Although having the report using alkaloid in pH- zone refining countercurrent separation Chinese medicine, this area in the prior art
Known, used solvent system is to influence one of key factor of separating resulting in the separation of pH- zone refining countercurrent, often
The solvent used has used in methanol, petroleum ether, ethyl acetate, n-hexane, acetone, chloroform, acetonitrile etc., each solvent system
Solvent be at least two kinds, the composition that different traditional Chinese medicine ingredients have, and the type and quantity of alkaloid are different, Chinese medicine warp
The composition difference for extracting obtained alkaloid gross sample is crossed, so how to select the solvent kind of solvent system for different Chinese medicine
Usage ratio between class, each solvent and the solvent system is coordinated to select what kind of flow velocity, applied sample amount, rotating speed etc. to obtain
It is without reference to value to the higher alkaloid monomer of purity.
Jateorrhizine has the effect in excited uterus, and the source being currently known is the Japanese barberry of Berberidaceae plant
Berberis thunbergii DC rhizomes, ranunculaceae plant coptis Coptis chinensis Franch rhizomes, Menispermaceae are planted
Thing herba fibraureae recisae Fibraurea tinetoria Lour roots, Africa palm leaf root of fangji Jatrorrhiza palmata (DC.) Miers
(J.columba.Miers), bloodroot Bock Nimu Bocconia frutesces Linn leaves, Annonaceae plant according to
Southern wood Enantia chlorantha Oliver roots.At present, the relevant report of jateorrhizine is not isolated from leatherleaf mahonia also
Road, does not also utilize the record of alkaloid in pH- zone refining countercurrent separation leatherleaf mahonia.
The content of the invention
The purpose of the present invention is exactly to separate contribution there is provided a kind of pH- zone refining countercurrent to solve the above problems
The method of alkaloid compound in wood.
To achieve these goals, the present invention is adopted the following technical scheme that：
A kind of method for separating alkaloid compound in leatherleaf mahonia, is separated using pH- zone refining countercurrent, described
Separation in used condition be：Solvent system is chloroform：Methanol：Water=3.5-4.5:2.5-3.5:2.5-3.5 (preferably 4:
3:3), pH- zone refining countercurrent instrument column volume is 200-400 (preferably 300mL), applied sample amount 2-5g (preferably 3g), rotating speed
300-1000rpm (preferably 800rpm), upper phase is stationary phase, and lower phase is mobile phase, and flow velocity 1.5-2.5mL/min is (preferably
2.0mL/min), stationary phase retention rate 35.71%, Detection wavelength 250-260nm (preferably 254nm).
It is described：The extracting method of alkaloid compound in leatherleaf mahonia：(1) leatherleaf mahonia medicinal material is carried using ethanol
Take, extract solution is concentrated in vacuo to no alcohol taste, total extract is obtained；(2) total extract is adjusted to acidity, petroleum ether extraction degreasing
Afterwards, adjust to alkalescence, as stirring precipitation, leatherleaf mahonia alkaloid crude extract.
Using comprising the following steps that pH- zone refining countercurrent is separated：
(1) by solvent system, it is placed in separatory funnel, shakes up rear stratification, ready to balance is for a period of time afterwards by up and down two
Mutually separate, upper phase be stationary phase, lower phase be mobile phase, be above added to 60mM hydrochloric acid, under be added to 7.5mM triethylamines；
(2) it is 1 to take leatherleaf mahonia alkaloid crude extract to be dissolved in volume ratio:It is stand-by in the mixed liquor of 1 upper and lower phase, institute
The use magnitude relation for stating leatherleaf mahonia alkaloid crude extract and mixed liquor is 3:10(g/mL)；
(3) make first semi-preparative high-speed counter-current chromatograph sampling valve be in sample introduction state, by stationary phase pump with
20mL·min-1Flow velocity fills chromatography column, and termination of pumping, opening speed controller makes the chromatographic chromatography column of high velocity stream just
Turn, when reaching setting speed, in the liquid storage tube that the sample dissolved is injected to counter-current chromatograph sampling valve with syringe, be rotated into
Sample valve makes sample enter chromatography column to connect column state, and setting flow rate of mobile phase is 1.5-2.5mL/min (preferably 2.0mL/
Min), start pump mobile phase, target component then received according to detector ultraviolet spectrogram (Fig. 3), rotated evaporation, freezing
Dry solid powder.
Beneficial effects of the present invention：
The method of the present invention prepares cost and is less than prior art, and easy to operate, efficiency high can relatively high-volume therefrom medicine work(
Point of jateorrhizine of the purity more than 96%, jamaicin, palmatine, jateorrhizine monomeric compound is prepared in Lao Muzhong, separation
From preparation method, the present invention isolates jateorrhizine from Chinese medicine leatherleaf mahonia first.
Brief description of the drawings
Fig. 1 is process chart of the invention；
Fig. 2 is the pH- zone refining countercurrent figures that leatherleaf mahonia alkaloid gross sample is separated；
Fig. 3 is the high-efficient liquid phase chromatogram of alkaloid gross sample；
Fig. 4 is the high-efficient liquid phase chromatogram of jateorrhizine monomer；
Fig. 5 is the high-efficient liquid phase chromatogram of jamaicin monomer；
Fig. 6 is the high-efficient liquid phase chromatogram of palmatine monomer；
Fig. 7 is the high-efficient liquid phase chromatogram of jateorrhizine monomer；
Fig. 8 is the pH- zone refining countercurrents that the leatherleaf mahonia alkaloid gross sample of comparative example 1 is separated；
Fig. 9 is the pH- zone refining countercurrents that the leatherleaf mahonia alkaloid gross sample of comparative example 2 is separated.
Embodiment
The invention will be further described with embodiment below in conjunction with the accompanying drawings.
Embodiment 1：
As shown in monomer preparation flow figure in Fig. 1 leatherleaf mahonias.
Leatherleaf mahonia medicinal material 2kg is taken to extract 3 times (each 2h), filtering, filtrate decompression concentration with 95% alcohol reflux after crushing
To without alcohol taste.
By the extract solution after above-mentioned concentration, plus hydrochloric acid regulation pH=3,3~5 removing liposoluble constituents of petroleum ether extraction,
Water layer ammonification water regulation pH=9 after extraction, 10.6g must be precipitated by filtering, alkaloid gross sample needed for being.
Leatherleaf mahonia alkaloid gross sample is isolated and purified using pH- zone refining countercurrents
Solvent system is chloroform：Chloroform：Methanol：Water=4:3:3, high-speed counter-current chromatograph column volume is 300mL, applied sample amount
3g, rotating speed 800rpm, upper phase are stationary phase, and lower phase is mobile phase, flow velocity 2.0mL/min, stationary phase retention rate 35.71%, inspection
Survey wavelength 254nm.
Specifically operating procedure is：Solvent system is prepared by above-mentioned solvent ratios, is placed in separatory funnel, is stood after shaking up
Layering, ready to balance for a period of time afterwards will up and down two-phase separate, be above added to 60mM hydrochloric acid, under be added to 7.5mM triethylamines, to add
As being used as mobile phase under stationary phase, plus alkali on acid.Take 3g leatherleaf mahonia alkaloid crude extracts be dissolved in 5mL acid addings mutually and
5mL is not added with stand-by in the mixture of phase under alkali.The semi-preparative high-speed counter-current chromatograph developed using Shanghai with field company, it is
By plunger pump, sampling valve, Ultraviolet Detector, recorder and the chromatography column (spiral shell formed by polyfluortetraethylene pipe multi-lay winding
Coil post, capacity is 300mL) etc. composition, make first sampling valve be in sample introduction state, by stationary phase pump with flow velocity 20mL
min-1Fill chromatography column, termination of pumping.Opening speed controller, rotates forward the chromatographic chromatography column of high velocity stream, turn up
During 800rpm, in the liquid storage tube that the sample dissolved is injected to counter-current chromatograph sampling valve with syringe, rotation sampling valve is to connect
Column state, makes sample enter chromatography column.Setting flow rate of mobile phase is 2.0mL/min, starts pump mobile phase, then according to inspection
Survey device ultraviolet spectrogram (Fig. 3) and receive target component.Obtain jamaicin (157.2mg), jateorrhizine (160.6mg), palmatine
(169.8mg), jateorrhizine (28.1mg) and non-principal component (53.7mg), HPLC purity assays are more than 96%.
Utilize efficient liquid phase chromatographic analysis isolate, such as Fig. 3-Fig. 7, liquid-phase condition：Kromasil 100-5C18Post (4.6
× 250mmmm), ultraviolet detection wavelength 265nm, column temperature：25 DEG C, flow velocity：1.0mL/min, sample size：10 μ L, mobile phase is used
Acetonitrile：Salting liquid (1% triethylamine solution adjusts pH=3 with phosphoric acid)=25:75.
Structural Identification：To isolated alkaloid application Agilent 5973N mass spectrographs and Varian 600MHz nuclear-magnetisms
Resonance spectrometer carries out MS respectively,1The measure of H H NMR spectroscopies, the data obtained is as follows：
Jateorrhizine：UV(λmax,MeOH):264,345nm.Positive ESI-MS m/z 338[M+H]+.1H NMR
(DMSO-d6,600MHz)δppm:9.86 (1H, s, H-8), 8.98 (1H, s, H-13), 8.19 (1H, d, J=9.0Hz, H-11),
8.01 (1H, d, J=9.0Hz, H-12), 7.69 (1H, s, H-1), 6.86 (1H, s, H-4), 4.91 (2H, t, J=6.0Hz, H-
6),4.09(3H,s,10-OCH3),4.07(3H,s,9-OCH3),3.94(3H,s,2-OCH3), 3.14 (2H, t, J=6.0Hz,
H-5).
Jamaicin：UV(λmax,MeOH):263and 346nm.Positive ESI-MS m/z 336[M+H]+.1H NMR
(DMSO-d6,600MHz)δppm:9.90 (1H, s, H-8), 8.96 (1H, s, H-13), 8.21 (1H, d, J=9.0Hz, H-11),
8.01 (1H, d, J=9.0Hz, H-12), 7.80 (1H, s, H-1), 7.09 (1H, s, H-4), 6.18 (2H, s, 2,3-OCH2O),
4.94 (2H, t, J=6.0Hz, H-6), 4.10 (3H, s, 10-OCH3),4.07(3H,s,9-OCH3), 3.21 (2H, t, J=
6.0Hz,H-5).
Jateorrhizine：UV(λmax,MeOH):263,345nm.Positive ESI-MS m/z 338[M+H]+.1H NMR
(DMSO-d6,600MHz)δppm:9.88 (1H, s, H-8), 8.82 (1H, s, H-13), 8.20 (1H, d, J=9.0Hz, H-11),
8.06 (1H, d, J=9.0Hz, H-12), 7.57 (1H, s, H-1), 7.06 (1H, s, H-4), 4.93 (2H, t, J=6.0Hz, H-
6),4.09(3H,s,10-OCH3),4.07(3H,s,9-OCH3),3.90(3H,s,3-OCH3), 3.19 (2H, t, J=6.0Hz,
H-5).
Palmatine：UV(λmax,MeOH):272,345nm.Positive ESI-MS m/z 352[M+H]+.1H NMR
(DMSO-d6,600MHz)δppm:9.90 (1H, s, H-8), 9.08 (1H, s, H-13), 8.20 (1H, d, J=9.0Hz, H-11),
8.04 (1H, d, J=9.0Hz, H-12), 7.73 (1H, s, H-1), 7.10 (1H, s, H-4), 4.96 (2H, t, J=6.0Hz, H-
6),4.10(3H,s,10-OCH3),4.08(3H,s,9-OCH3),3.94(3H,s,2-OCH3),3.88(3H,s,3-OCH3),
3.23 (2H, t, J=6.0Hz, H-5)
Comparative example 1
Condition：Chloroform：Methanol：Water=4:3:3, upper addition 10mM HCl, lower addition 20mM triethylamines, flow velocity：2.0mL/
Min, temperature：25 DEG C, sample size 3g, retention rate：25%, other conditions and operation be the same as Example 1.As shown in Figure 8：Separation knot
Really：Only separate jamaicin and jateorrhizine.The flourish embodiment 1 of others operation.
Comparative example 2
Condition：N-hexane：Ethyl acetate：Methanol：Water=5:5:3:7, upper addition 10mM HCl, the lower second of addition 20mM tri-
Amine, flow velocity：2.0mL/min, temperature：25 DEG C, sample size 3g, retention rate：58%, other conditions and operation be the same as Example 1.Such as
Shown in Fig. 9：Separating resulting：Single compound is not isolated.
Although above-mentioned the embodiment of the present invention is described with reference to accompanying drawing, not to present invention protection model
The limitation enclosed, one of ordinary skill in the art should be understood that on the basis of technical scheme those skilled in the art are not
Need to pay various modifications or deform still within protection scope of the present invention that creative work can make.
Claims (9)
1. a kind of method for separating alkaloid compound in leatherleaf mahonia, is separated using pH- zone refining countercurrent, described
Used condition is in separation：Solvent system is chloroform：Methanol：Water=3.5-4.5:2.5-3.5:2.5-3.5, pH- zone
Refining countercurrent instrument column volume is 200-400ml, applied sample amount 2-5g, rotating speed 300-1000rpm, and upper phase is stationary phase, lower phase
For mobile phase, flow velocity 1.5-2.5mL/min, stationary phase retention rate 35.71%, Detection wavelength 250-260nm, in the leatherleaf mahonia
The extracting method of alkaloid compound：(1) leatherleaf mahonia medicinal material is extracted using ethanol, extract solution is concentrated in vacuo to nothing
Alcohol taste, obtains total extract；(2) total extract is adjusted to acidity, after petroleum ether extraction degreasing, adjusted to alkalescence, stirring is precipitated, i.e.,
For leatherleaf mahonia alkaloid crude extract.
2. the method as described in claim 1, it is characterized in that：The solvent system is chloroform：Methanol：Water=4:3:3.
3. the method as described in claim 1, it is characterized in that：The pH- zone refining countercurrent instrument column volume is 300mL.
4. the method as described in claim 1, it is characterized in that：The applied sample amount 3g.
5. the method as described in claim 1, it is characterized in that：The rotating speed 800rpm.
6. the method as described in claim 1, it is characterized in that：The flow velocity 2.0mL/min.
7. the method as described in claim 1, it is characterized in that：The Detection wavelength 254nm.
8. the method as described in claim 1, it is characterized in that：The specific step of the application pH- zone refining countercurrent separation
It is rapid as follows：
(1) by solvent system, it is placed in separatory funnel, shakes up rear stratification, ready to balance two-phase will divides up and down afterwards for a period of time
Open, upper phase be stationary phase, lower phase be mobile phase, be above added to 60mM hydrochloric acid, under be added to 7.5mM triethylamines；
(2) it is 1 to take leatherleaf mahonia alkaloid crude extract to be dissolved in volume ratio:It is stand-by in the mixed liquor of 1 upper and lower phase, the work(
Labor wood alkaloid crude extract quality and mixed liquor volumetric usage relation be 3g:10ml；
(3) semi-preparative high-speed counter-current chromatograph sampling valve is made to be in sample introduction state first, by stationary phase pump with 20mL
Min-1 flow velocitys fill chromatography column, and termination of pumping, opening speed controller rotates forward the chromatographic chromatography column of high velocity stream, reached
During to setting speed, in the liquid storage tube that the sample dissolved is injected to counter-current chromatograph sampling valve with syringe, sampling valve is rotated
To connect column state, sample is set to enter chromatography column, setting flow rate of mobile phase is 1.5-2.5mL/min, starts pump mobile phase, so
Target component is received according to detector ultraviolet spectrogram afterwards, rotated evaporation is freeze-dried to obtain solid powder.
9. method as claimed in claim 8, it is characterized in that：It is 2mL/min that flow rate of mobile phase is set in the step (3).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610133908.9A CN105693714B (en) | 2016-03-09 | 2016-03-09 | The method of alkaloid compound in pH zone refining countercurrent separation leatherleaf mahonia |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610133908.9A CN105693714B (en) | 2016-03-09 | 2016-03-09 | The method of alkaloid compound in pH zone refining countercurrent separation leatherleaf mahonia |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105693714A CN105693714A (en) | 2016-06-22 |
| CN105693714B true CN105693714B (en) | 2017-08-25 |
Family
ID=56220344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610133908.9A Active CN105693714B (en) | 2016-03-09 | 2016-03-09 | The method of alkaloid compound in pH zone refining countercurrent separation leatherleaf mahonia |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105693714B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110384697B (en) * | 2019-08-22 | 2021-07-27 | 深圳市药品检验研究院（深圳市医疗器械检测中心） | Anti-acetylcholinesterase active composition in mahonia stem and screening method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994020850A1 (en) * | 1993-03-05 | 1994-09-15 | The Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | pH-ZONE-REFINING COUNTERCURRENT CHROMATOGRAPHY |
| CN101973990A (en) * | 2010-10-20 | 2011-02-16 | 浙江工业大学 | Method for separating dehydrocorydaline by pH-zone-refining countercurrent chromatography |
| CN102060853A (en) * | 2010-12-13 | 2011-05-18 | 中国药科大学 | Method for separating alkaloid by reversely two-way eluted pH-zone-refining counter-current chromatography |
| CN103933100A (en) * | 2013-01-17 | 2014-07-23 | 何欣 | Preparation method of total alkaloid of Chinese mahonia stem and applications of total alkaloid of Chinese mahonia stem in preparation of drugs for preventing and treating gastric ulcer |
-
2016
- 2016-03-09 CN CN201610133908.9A patent/CN105693714B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994020850A1 (en) * | 1993-03-05 | 1994-09-15 | The Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | pH-ZONE-REFINING COUNTERCURRENT CHROMATOGRAPHY |
| CN101973990A (en) * | 2010-10-20 | 2011-02-16 | 浙江工业大学 | Method for separating dehydrocorydaline by pH-zone-refining countercurrent chromatography |
| CN102060853A (en) * | 2010-12-13 | 2011-05-18 | 中国药科大学 | Method for separating alkaloid by reversely two-way eluted pH-zone-refining counter-current chromatography |
| CN103933100A (en) * | 2013-01-17 | 2014-07-23 | 何欣 | Preparation method of total alkaloid of Chinese mahonia stem and applications of total alkaloid of Chinese mahonia stem in preparation of drugs for preventing and treating gastric ulcer |
Non-Patent Citations (1)
| Title |
|---|
| pH区带精制逆流色谱在中药中的研究进展;黄娟等;《中草药》;20070228;第38卷(第2期);第308-309页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105693714A (en) | 2016-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110294673A (en) | Caffeoylquinic acids butyl ester class isomer and its preparation method and application | |
| CN105541601B (en) | The method for separating and preparing of organic acid monomer and application in a kind of sunglo | |
| CN1289470C (en) | Process for rapid preparation of high pure pharmaceutical matters from patrinia villosa juss | |
| CN105732611B (en) | Method for separating alkaloids compound in caulis mahoniae by high-speed countercurrent chromatography | |
| CN105693714B (en) | The method of alkaloid compound in pH zone refining countercurrent separation leatherleaf mahonia | |
| CN110194758A (en) | A method of the fast separating and purifying Aristolochic Acid compound from caulis aristologhiae manshuriensis | |
| CN106967136A (en) | A kind of method of separating high-purity oleuropein | |
| CN111560024B (en) | Method for separating gelsemium elegans alkaloid monomer from gelsemium elegans alkaloid by combining high-speed counter-current chromatography with preparative liquid chromatography | |
| Li et al. | Microwave-assisted extraction coupled with counter-current chromatography and preparative liquid chromatography for the preparation of six furocoumarins from Angelica Pubescentis Radix | |
| CN102108072B (en) | Method for preparing senkyunolide I from extract of Chinese angelica | |
| CN113831313B (en) | Preparation method and application of high-purity coumarin derivative | |
| CN109053433A (en) | A kind of method that combination prepares ginkgoic acid | |
| CN104788990B (en) | A kind of method extracted from laba garlic with separating yellow element | |
| Tang et al. | Preparative isolation and purification of chemical components from Aconitum coreanum by high‐speed counter‐current chromatography coupled with evaporative light scattering detection | |
| CN104447720B (en) | Method for separating vicenin-2 from linearstripe rabdosia herb | |
| CN109369382A (en) | A kind of preparation method of ginkgo acids ingredient | |
| CN108084241B (en) | The method that separation prepares fucosterol from sargassum fusifome | |
| CN112552150B (en) | Method for preparing asarone monomer based on coordination effect | |
| CN109180774A (en) | A kind of pharmaceutical composition and preparation method thereof containing Fructus Tribuli fruit total saponin | |
| CN114280201B (en) | Efficient separation method of polyphenol components in dandelion | |
| CN111948319B (en) | Efficient separation and analysis method for active ingredients in enteromorpha | |
| CN109053417A (en) | A kind of preparation method of high-purity ginkgoic acid | |
| CN114085258B (en) | Method for separating oleuropein from olive leaves by countercurrent chromatography continuous sampling | |
| CN104262354B (en) | A kind of method preparing 8-methoxypsoralen | |
| CN102127124A (en) | Method for preparing hydroxysafflor yellow A |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20160622 Assignee: Beijing Emilion Technology Co., Ltd. Assignor: Shandong Analysis Test Center Contract record no.: X2019370000028 Denomination of invention: Method for separating alkaloidal compounds from Chinese mahonia stems with pH-zone-refining countercurrent chromatography Granted publication date: 20170825 License type: Exclusive License Record date: 20191213 |
|
| EE01 | Entry into force of recordation of patent licensing contract |