CN108341845A - The method that cornel extractive prepares high-purity morroniside - Google Patents
The method that cornel extractive prepares high-purity morroniside Download PDFInfo
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- CN108341845A CN108341845A CN201810279482.7A CN201810279482A CN108341845A CN 108341845 A CN108341845 A CN 108341845A CN 201810279482 A CN201810279482 A CN 201810279482A CN 108341845 A CN108341845 A CN 108341845A
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- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
The present invention relates to a kind of methods that cornel extractive prepares high-purity morroniside.Cornel extractive is after macroporous adsorbing resin for purification and purification on normal-phase silica gel initial gross separation, then reverse phase silica gel chromatographic column is pressed in passing through, and mobile phase is second alcohol and water, carries out gradient elution, and the eluent that will be enriched in morroniside is concentrated under reduced pressure to give the morroniside crude product of pure degree≤90%；It is most purified through 20 gel column chromatographies of Sephadex LH, is eluted using chloroform and methanol mixed solvent afterwards, eluent evaporated under reduced pressure obtains the morroniside of pure degree≤98%.This method separating effect is notable, and speed is fast, efficient, while operation is simple, mild condition.
Description
Technical field
The present invention relates to a kind of methods of cornel extractive preparation high-purity morroniside more particularly to a kind of use to not
Promise glycosides has the middle pressure reversed-phase silica gel column chromatography for being significantly separated purification effect and (hydroxypropyl glucan is solidifying by combination Sephadex LH-20
Glue) gel column chromatography prepare high-purity target compound separation method.
Background technology
Fructus Corni is a kind of using very extensive conventional Chinese medicine, has anti-senile dementia, antitumor, protection angiocarpy etc.
Pharmacological action.Morroniside is that wherein one of main component, pharmacological research show that morroniside has anti-inflammatory, anti-oxidant, neuroprotection
The effects that.Recent study shows that morroniside has fabulous development and application potentiality in terms of anti-senile dementia activity.It finds simple
The method that high-purity morroniside is prepared in easy slave Fructus Corni, it is important using having to the further research and development of morroniside
Value.However, up to now, there are no the methods for preparing high-purity morroniside from Fructus Corni or its extract.
There are numerous patents to report the method for preparing morroniside from Fructus Corni：1569867 A of Chinese patent CN are using big
Hole resin cleans, then the morroniside of purity 95.81% is prepared with efficient liquid phase, and the method needs to use high performance liquid chromatography
Instrument, equipment and chromatographic column are of high cost, and a preparation amount is few, are not suitable for a large amount of prepare；In 101385735 A of Chinese patent CN
Report is recrystallized to give the morroniside that purity is 95%, but the first time of this patent report after the separation of macroreticular resin twice
Macroporous resin column needs extracting solution being acidified, this may result in the variation of morroniside structure, while the side of recrystallization purifying
Method, it is bothersome laborious, and the amount that can take high-purity target compound is also very limited；Chinese patent CN 101336927 A, CN
101974048 A and 104987354 A of CN are to purify to obtain morroniside by the way of recrystallization, it is evident that this method
A large amount of morronisides for preparing high-purity difficult to realize and time-consuming length；102127140 A of Chinese patent CN are removed using macroreticular resin
Miscellaneous, extracting n-butyl alcohol obtains morroniside, and purity is only 60%-70%, and purity is too low.
Invention content
It is an object of the invention to be directed in existing preparation method and technology to prepare insufficient existing for purifying morroniside, proposition
A kind of preparation method is simple, easy to operate, and yield is high and is suitble to the method for large-scale production and preparation high-purity morroniside.The present invention
Method is simple and practicable, and the high-purity morroniside of Chun Du≤98% (quality %, same as below) can largely be prepared.
A kind of method that cornel extractive prepares high-purity morroniside, cornel extractive is through macroporous adsorbing resin for purification
It is further comprising the steps of after purification on normal-phase silica gel initial gross separation：
(1) reverse phase silica gel post separation is pressed in：Contain what is obtained through macroporous adsorbing resin for purification and purification on normal-phase silica gel initial gross separation
Morroniside samples with water dissolves, and it is second alcohol and water that reverse phase silica gel chromatographic column, mobile phase are pressed in, carries out gradient elution, will be enriched in
The eluent of morroniside is concentrated under reduced pressure, and obtains the morroniside crude product of Chun Du≤90%；
(2) gel column purification：The morroniside crude product of Chun Du≤90% is through Sephadex LH-20 gel (hydroxypropyl glucans
Gel) column purified, eluted using chloroform and methanol mixed solvent, and eluent evaporated under reduced pressure obtains the Monot of high-purity
Glycosides.
In step (1), middle pressure reverse phase silica gel post separation uses instrument for middle pressure chromatograph, and pressure makes between 0-50MPa
Service pressure is between 5-25MPa；It is detached with middle pressure reversed-phase silica gel column chromatography, column chromatography is reverse phase silica gel column, reverse phase silicon used
Glue filler is C18 fillers.
When middle pressure reverse phase silica gel separation, reversed-phase silica gel column chromatography is medium pressure column chromatography, and using wet method loading, mobile phase is second
The volume ratio of the mixed solvent of alcohol and water, ethyl alcohol and water is 5:95~10:After 90 carry out gradient elution, according to silica gel thin-layer chromatography
Merge same composition with high performance liquid chromatography, is concentrated under reduced pressure to give the morroniside crude product of Chun Du≤90%.Middle pressure reverse phase silica gel column
(wet method loading) gained morroniside is chromatographed in addition to a small amount of Yang product Chun Du≤98%, most Chun Du≤90%.
Preferably, solvent elution flow rate is 10-50ml/min, 3-5 column volume of each gradient elution.Mobile phase according to
The volume ratio of ethyl alcohol and water is respectively 5:95、7:93、8:92、10:90 carry out gradient elution.
In step (2), when being purified using Sephadex LH-20 gel column chromatographies, mobile phase be chloroform and methanol,
The volume ratio of chloroform and methanol can be 0:1~2.5:Any ratio between 1, the i.e. volume ratio of chloroform and methanol are 0:1,0.5:
1,1:1,1.5:1,2:1,2.5:1 or any ratio between make solvent.Preferably, the volume ratio of chloroform and methanol is
1.5:1。
Sephadex LH-20 gel column chromatographies are according to pillar diameter and length, and flow control is in 2~20ml/min.
Same composition is merged according to silica gel thin-layer chromatography and high performance liquid chromatography after elution, evaporated under reduced pressure obtain Chun Du≤
98% morroniside.
In the present invention, the preparation method of cornel extractive can be：Dry cornus fruit is smashed it through into 20 mesh sieve,
50% ethyl alcohol, liquid ratio 10 are added in the powder of screening:1 (ml/g) carries out ultrasonic extraction, and three times, merging carries for continuous extraction
Cornel extractive powder is obtained after taking liquid, reduced pressure to be evaporated.The process conditions of ultrasonic extraction：It carries out at room temperature, ultrasonic wave
Power be 300W, extraction time be each 45min~60min.
Macroporous adsorbing resin for purification：By, through large pore resin absorption column, mobile phase is water after cornel extractive water dissolution
And/or ethyl alcohol, gradient elution is carried out, the eluent rich in morroniside is collected, is recovered under reduced pressure to obtain dry eluate.
Preferably, macroporous adsorbing resin for purification is by cornel extractive water dissolution, and filtering removes insoluble matter, liquid
Through HP-20 type large pore resin absorption columns, use respectively water, 10% ethyl alcohol (volume %, same as below), 40% ethyl alcohol, 70% ethyl alcohol,
95% ethanol gradient elution collects 40% ethanol eluate, is recovered under reduced pressure to obtain dry eluate.Preferably, solvent elution stream
Speed is 10-50ml/min, 3-5 column volume of each gradient elution.
Normal phase silicagel column initial gross separation：After gained eluate is dissolved, purification on normal-phase silica gel mixes sample, mixes sample silica gel dry method loading,
Mobile phase is chloroform and methanol, carries out gradient elution, collects the eluent rich in morroniside, sample containing morroniside is concentrated under reduced pressure to obtain
Product.
Preferably, normal phase silicagel column is initially separated into gained eluate is dissolved with methanol after, purification on normal-phase silica gel mixes sample, mixes sample
Silica gel dry method loading, mobile phase are chloroform：Methanol=15:1~8:1 carries out gradient elution, merges chloroform：Methanol=10:1~9:
1 same composition, is concentrated under reduced pressure to obtain sample containing morroniside, and purification on normal-phase silica gel used is 160~200 mesh.Preferably, solvent elution flow rate
For 10-50ml/min, 2-5 column volume of each gradient elution.Mobile phase is respectively 15 according to the volume ratio of chloroform and methanol:
1、12:1、10:1、9:1、8:1 gradient is eluted.
Obtained monomer morroniside is detected using efficient liquid phase, the final purity for determining morroniside.It is of the present invention
HPLC analysis methods, liquid chromatograph are 2545 types of Waters, 2998 detector, chromatographic column:Waters sunfire
C18Column (4.6*250mm, 5 μm), mobile phase：Methanol：Water=30:70, flow velocity：1mL/min, Detection wavelength：240nm.
Cornel extractive after purification, is still mixed with a large amount of analogs through macroreticular resin and purification on normal-phase silica gel, and reverse phase silicon is pressed in
Not only separating effect is notable for glue, and speed is fast, efficient.Mobile phase is chloroform and methanol used in gel Sephadex LH-20
Different proportion, eluant, eluent used are positive phase systems, that is, ensure that separating effect, ensure that quick separating and recycling.Chun Du≤
90% morroniside crude product, through gel filtration chromatography (wet method loading, wet method dress post, filler can be used for a long time repeatedly after once filling column)
Method, the high-purity morroniside of Han Liang≤98% can be obtained.Operation is simple for this method, mild condition, reverse phase silica gel column
It can Reusability with gel column.
The method of the present invention can obtain the morroniside of high-purity from cornel extractive.The present invention is tasted by repeatedly groping
Examination, finally selects a best purifying process route, and a kind of simple to operation, and efficiently a large amount of preparation contents are provided for market
The method of the morroniside of≤98% high-purity.
Description of the drawings
Fig. 1 is morroniside purity test HPLC chromatogram.
Specific implementation mode
The method that the present invention prepares high-purity morroniside from Fructus Corni, including step in detail below：
Step 1：Fructus Corni dry fruit be crushed into 20 mesh sieve, 50% ethyl alcohol of solvent, liquid ratio is with 10:1(ml/g)
Ultrasonic extraction is carried out, continuous extraction three times, merges extracting solution, and reduced pressure obtains Fructus Corni crude extract powder after being evaporated.
Step 2：Above-mentioned powder water dissolution, filtering remove insoluble matter, liquid through HP-20 type large pore resin absorption columns,
Mobile phase uses water, 10% ethyl alcohol, 40% ethyl alcohol, 70% ethyl alcohol, 95% ethanol gradient elution successively, collects 40% ethanol elution
Liquid, vacuum distillation drying recycle to obtain dry eluate.
Step 3：Above-mentioned eluate is dissolved with methanol, purification on normal-phase silica gel mixes sample, with normal pressure normal phase silica gel column chromatography, will mix
Sample silica gel dry method loading, dry method upper prop, mobile phase chloroform：Methanol=15:1~8:1 carries out gradient elution, collects and merges chlorine
It is imitative：Methanol=10:1~9:1 flow point merges same composition；Sample containing morroniside is concentrated under reduced pressure to obtain, purification on normal-phase silica gel used is 160
~200 mesh.
Step 4：Morroniside sample will be contained to be dissolved with pure water, by middle pressure reversed-phase silica gel column chromatography, i.e., upper middle pressure reverse phase
C18 chromatographic columns, mobile phase：Ethyl alcohol：Water=5:95~10:90 gradients are eluted, and same composition is merged；Obtain Chun Du≤90%
Morroniside crude product.
Step 5：The morroniside crude product of 90% purity, with Spehadex LH-20 gel-purifieds, mobile phase is chloroform：First
Alcohol=1.5:1 is eluted, and same composition is merged, and the morroniside for being evaporated get Dao≤98% high-purity is concentrated under reduced pressure.By what is obtained
Monomer is detected with efficient liquid phase, final to determine morroniside purity.
The concentration of ethyl alcohol refers both to volumetric concentration in the present invention, and the ratio between in the mixed solvent solvent refers both to volume ratio, not
The purity of promise glycosides is mass percent purity.
The extraction of 1 cornus fruit of embodiment
Dry cornus fruit 10kg be crushed into 20 mesh sieve, 50% ethyl alcohol of solvent, liquid ratio is with 10:1(ml/g)
Ultrasonic extraction is carried out, the power of ultrasonic wave is 300W, extraction time 60min, and continuous extraction three times, merges extracting solution, decompression
Concentrate drying obtains cornel extractive.
The preparation of 2 high-purity morroniside of embodiment
1) macroporous adsorbing resin for purification
It by cornel extractive, is dissolved in water, filters, obtain filtrate.Filtrate is crossed into HP-20 type large pore resin absorption columns, is made
After sample absorption completely, pure water, 10%, 40%, 70%, 95% ethanol gradient elution are used successively, collects eluent.Flow velocity is
40ml/min, 3 column volumes of each gradient elution.According to thin layer and high performance liquid chromatography detection, object is all enriched in
Drying is concentrated under reduced pressure in 40% alcohol elution by 40% alcohol elution.
2) purification on normal-phase silica gel post separation
Above-mentioned dried object 500g is taken, is dissolved with 5000ml methanol, purification on normal-phase silica gel (160-200 mesh) mixes sample；With normal pressure silica gel
Pillar layer separation will mix sample silica gel dry method loading, 5000g purification on normal-phase silica gel (160-200 mesh) dry method upper prop, mobile phase chloroform：
Methanol=15:1~8:1, the volume ratio according to chloroform and methanol is respectively 15:1、12:1、10:1、9:1、8:1, it carries out gradient and washes
It is de-, flow velocity 30ml/min, 3 column volumes of each gradient elution.Merge chloroform：Methanol=10:1~9:1 same composition；Decompression
Recycling obtains sample containing morroniside.
3) reverse phase silica gel post separation is pressed in
Take the 100g of sample containing morroniside in step 2) to be dissolved with pure water, filter, pressed during filtrate is upper (pressure 0-50MPa it
Between, make service pressure between 5-25MPa) reverse phase C18 columns (filler C18, amount of fill 1200g), mobile phase use：Ethyl alcohol：Water=
5:95~10:90, the volume ratio according to ethyl alcohol and water is respectively 5:95、7:93、8:92、10:90 carry out gradient elution, flow velocity：
30ml/min, 4 column volumes of each gradient elution；Merge same composition according to silica gel thin-layer chromatography and high performance liquid chromatography, subtracts
Pressure is concentrated and dried, and obtains the morroniside crude product of Chun Du≤90%.Middle pressure reverse phase silica gel column, it can be used repeatedly for primary dress column, and
Elution speed is fast, and the time is short, efficient.
4) gel column purification
The morroniside crude product for taking step 3) Zhong Chun Du≤90% is purified with Sephadex LH-20 gels, mobile phase
Use chloroform：Methanol=1.5:1 is eluted, flow velocity 6ml/min, merges phase according to silica gel thin-layer chromatography and high performance liquid chromatography
Same component, morronisides of the evaporated under reduced pressure get Dao≤98% high-content.It can be used repeatedly for gel column, and mobile phase used is positive body
System, each column chromatography time is short, and separation and organic efficiency are high.
Embodiment 3HPLC detection methods
Liquid chromatograph：2998 type UV detector of Waters2545 types
Chromatographic column:Waters sunfire C18Column (4.6 × 250mm, 5 μm)
Mobile phase：Methanol：Water=30:70
Flow velocity：1mL/min
Detection wavelength：240nm
Sample size:10μl
Appearance time：9.22min
Test sample and reference substance prepare solution：Hplc grade methanol dissolves.
Using above-mentioned instrument and method, the morroniside obtained to embodiment 2 is detected, morroniside purity test HPLC colors
Spectrum is determined as morroniside monomer, and Chun Du≤98% as shown in Figure 1, through being compared with reference substance collection of illustrative plates.
Cornel extractive through macroporous absorbent resin and purification on normal-phase silica gel initial gross separation, then is pressed reverse phase silica gel by the present invention in
Separation, mobile phase ethyl alcohol：Water=5:95~10:90 carry out gradient elutions, merge same composition, be concentrated under reduced pressure to give Chun Du≤
90% morroniside crude product；It is most purified afterwards through Sephadex LH-20 gel column chromatographies, mobile phase is used：Chloroform：Methanol=1.5:1
It is eluted, merges same composition, evaporated under reduced pressure obtains morroniside of the purity 98% or more.This method separating effect is notable,
Speed is fast, efficient, while operation is simple, mild condition.
Claims (8)
1. a kind of method that cornel extractive prepares high-purity morroniside, cornel extractive through macroporous adsorbing resin for purification and
After purification on normal-phase silica gel initial gross separation, it is characterised in that further comprising the steps of：
(1) pressure reverse phase silica gel separation in：Contain morroniside by what is obtained through macroporous adsorbing resin for purification and purification on normal-phase silica gel initial gross separation
Samples with water dissolves, and it is second alcohol and water that reverse phase silica gel chromatographic column, mobile phase are pressed in, carries out gradient elution, will be enriched in morroniside
Eluent be concentrated under reduced pressure to give morroniside crude product；
(2) gel column purification：Morroniside crude product is purified through Sephadex LH-20 gel columns, it is mixed using chloroform and methanol
Bonding solvent is eluted, the morroniside that eluent evaporated under reduced pressure obtains.
2. the method that cornel extractive according to claim 1 prepares high-purity morroniside, it is characterised in that：Middle pressure is anti-
The separation of phase silica gel uses instrument for middle pressure chromatograph, and reverse phase silica gel column uses reverse phase silica gel filler for C18 fillers.
3. the method that cornel extractive according to claim 2 prepares high-purity morroniside, it is characterised in that：Middle pressure is anti-
When phase silica gel detaches, using wet method loading, mobile phase is the mixed solvent of second alcohol and water, and the volume ratio of ethyl alcohol and water is 5:95~
10:90, after gradient elution, merges same composition, be concentrated under reduced pressure to give morroniside crude product.
4. the method that cornel extractive according to claim 3 prepares high-purity morroniside, it is characterised in that：Gained is not
The mass of purity Wei≤90 % of promise glycosides crude product.
5. the method that cornel extractive according to claim 1 prepares high-purity morroniside, it is characterised in that：Using
When Sephadex LH-20 gel column chromatographies are purified, mobile phase is chloroform and methanol, and the volume ratio of chloroform and methanol is 0:1
~2.5:1.
6. the method that cornel extractive according to claim 5 prepares high-purity morroniside, it is characterised in that：The stream
In dynamic phase, the volume ratio of chloroform and methanol is 1.5:1.
7. the method that cornel extractive according to claim 6 prepares high-purity morroniside, it is characterised in that：Using
When Sephadex LH-20 gel columns are purified, the flow velocity of elution is 2~20ml/min.
8. the method that cornel extractive according to claim 1 prepares high-purity morroniside, it is characterised in that：Gained is not
The mass of Chun Du≤98 % of promise glycosides.
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| CN201810079068 | 2018-01-26 | ||
| CN2018100790681 | 2018-01-26 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114213482A (en) * | 2022-01-11 | 2022-03-22 | 湖北民族大学 | Preparation method of high-purity morroniside |
| CN115785177A (en) * | 2022-12-16 | 2023-03-14 | 黄山学院 | High-purity morroniside and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1569867A (en) * | 2004-04-28 | 2005-01-26 | 江苏中康新药指纹图谱开发有限公司 | Preparation method and use of skunk bush extract morroniside |
| CN101974048A (en) * | 2010-06-28 | 2011-02-16 | 南京泽朗农业发展有限公司 | Method for extracting morroniside from dogwood |
| CN102127140A (en) * | 2010-11-25 | 2011-07-20 | 南京泽朗医药科技有限公司 | Method for combinedly extracting Morroniside, dogwood polysaccharide and ursolic acid from dogwood |
| CN104987354A (en) * | 2015-07-23 | 2015-10-21 | 北京市药品检验所 | Method for preparing morroniside |
-
2018
- 2018-03-30 CN CN201810279482.7A patent/CN108341845B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1569867A (en) * | 2004-04-28 | 2005-01-26 | 江苏中康新药指纹图谱开发有限公司 | Preparation method and use of skunk bush extract morroniside |
| CN101974048A (en) * | 2010-06-28 | 2011-02-16 | 南京泽朗农业发展有限公司 | Method for extracting morroniside from dogwood |
| CN102127140A (en) * | 2010-11-25 | 2011-07-20 | 南京泽朗医药科技有限公司 | Method for combinedly extracting Morroniside, dogwood polysaccharide and ursolic acid from dogwood |
| CN104987354A (en) * | 2015-07-23 | 2015-10-21 | 北京市药品检验所 | Method for preparing morroniside |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114213482A (en) * | 2022-01-11 | 2022-03-22 | 湖北民族大学 | Preparation method of high-purity morroniside |
| CN114213482B (en) * | 2022-01-11 | 2024-05-10 | 湖北民族大学 | Preparation method of high-purity morroniside |
| CN115785177A (en) * | 2022-12-16 | 2023-03-14 | 黄山学院 | High-purity morroniside and preparation method thereof |
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