CN104711301B - A kind of preparation method of icariine - Google Patents
A kind of preparation method of icariine Download PDFInfo
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- CN104711301B CN104711301B CN201510128987.XA CN201510128987A CN104711301B CN 104711301 B CN104711301 B CN 104711301B CN 201510128987 A CN201510128987 A CN 201510128987A CN 104711301 B CN104711301 B CN 104711301B
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Abstract
The present invention provides a kind of preparation method of icariine, and this approach includes the following steps：Shorthorned Epimedium P.E is subjected to enzyme digestion reaction under the action of β glycosidases first；Then enzyme digestion reaction product step a obtained filters；Again by filtered filter cake acetone solution；Water is added into acetone soln, reflux dissolving, by solution left standstill, crystal is collected in filtering, obtains the icariine.Icariine in the present invention reaches 20% relative to Shorthorned Epimedium P.E yield, and the purity of icariine reaches 99.8%.
Description
Technical field
The present invention relates to a kind of preparation methods of icariine, belong to field of medicaments.
Background technology
A Kelading also known as icariine, epimedium aglucone are that isolated excessive sheep is extracted from Chinese medicine Herba Epimedii
The new effective monomer that leaves of pulse plants extract is obtained through enzymatic conversion, shown in structure such as following formula (I)：
The preparation method of the compound is disclosed in CN101302548B.This method is using icariin as raw material, with β-grape
Glycosidase is hydrolyzed, and supernatant is obtained by filtration in the precipitation acetone solution that hydrolysate centrifuges.The supernatant is used again
Water is recrystallized, and icariine sterling is obtained.
Disclosed in the Chinese patent application No. is 201010517793.6 it is a kind of using naringinase from icariin
Icariin standard items are dissolved in alcohol solvent, are added under the conditions of 40-70 DEG C by the method for obtaining epimedium aglucone, this method
Naringinase is digested, and epimedium aglucone is obtained.
A kind of preparation method of epimedium aglucone is disclosed in the Chinese patent application No. is 200910184282.4, it should
Method is extracted using Herba Epimedii as raw material by methanol, snail enzyme hydrolysis and etc. obtain epimedium aglucone crude product.
However, with icariin in method made above, or by raw material of Herba Epimedii methanolic extract carry out enzymolysis preparation
Icariine.Icariine is prepared using Herba Epimedii methanolic extract as raw material, what is obtained is icariine crude product；With icariin
When preparing icariine for raw material, another ingredient epimedin C in Herba Epimedii cannot be converted to icariine.So above
It is low in the presence of enzymolysis conversion ratio in three kinds of methods, the defect more than finished product impurity.
Invention content
The object of the present invention is to provide a kind of preparation method of icariine, the icariine prepared by this method has
The advantage that high conversion rate, purity are high and impurity is few.
The present invention provides a kind of preparation methods of icariine, and this approach includes the following steps：
A. Shorthorned Epimedium P.E is subjected to enzyme digestion reaction under the action of beta -glycosidase first；
B. the enzyme digestion reaction product then obtained step a filters；
C. again by filtered filter cake acetone solution；
D. it is added water into acetone soln, reflux dissolving, by solution left standstill, crystal is collected in filtering, is obtained described excessive
Sheep leaves of pulse plants element.
Preferably, the mass content summation of icariin and epimedin C is at least in the Shorthorned Epimedium P.E in the step a
It is 5%.
Preferably, in the step a, Shorthorned Epimedium P.E is scattered in the buffer solution that pH value is 3.5-7.5,
And when temperature is increased to 35-65 DEG C, enzyme digestion reaction is carried out under the action of beta -glycosidase.
Preferably, the buffer solution is disodium hydrogen phosphate-potassium dihydrogen phosphate, the acetic acid-acetic acid of pH value 4.0-7.0
Sodium, phosphoric acid-sodium phosphate, citric acid-sodium citrate or disodium hydrogen phosphate-citric acid solution.
Most preferably, the quality of the volume of buffer solution/L and Shorthorned Epimedium P.E/Kg ratios are 5-30:1.
Preferably, the enzyme digestion reaction time described in step a is 8-48 hours, and enzyme digestion reaction temperature is 35-65 DEG C.
Preferably, the mass ratio of the Shorthorned Epimedium P.E in step a and beta -glycosidase is 1-50:1.
It is highly preferred that the mass ratio of Shorthorned Epimedium P.E and beta -glycosidase is 2-30 in step a:1.
Most preferably, the mass ratio of Shorthorned Epimedium P.E and beta -glycosidase is 5-20 in step a:1.
Preferably, it in the step c, first by filtered filtration cakes torrefaction, then crushes, then will be after crushing
Filter cake be scattered in acetone solvent and dissolve, volume/L of acetone solvent is equivalent to 2-20 times of crushing filter cake quality/Kg, obtains
Acetone soln.
Preferably, in the step d, volume/L that water is added in acetone soln is equivalent to the 2- of filter cake quality/Kg
20 times, and the solution is stood at room temperature.
Preferably, in the step a, Shorthorned Epimedium P.E passes through alcohol solvent using Herba Epimedii Chinese medicine as raw material
Extraction is made.
Preferably, the alcohol solvent is ethyl alcohol water mixed solvent, and ethyl alcohol water mixed solvent extracts Herba Epimedii Chinese medicine
Obtained extract first passes around concentration, is then adsorbed by macroporous resin column, then with water and volumetric concentration is respectively 30%-
100% ethanol water solvent is eluted, and the Shorthorned Epimedium P.E for enzyme digestion reaction is obtained.
Preferably, the volume ratio of the ethanol water in the mixed solvent, second alcohol and water is 40:10-160, mixed solvent
Volume/L is 4-20 times of Herba Epimedii Chinese medicine quality/Kg, is extracted 1-5 times altogether, every time reflux 1-5 hours.
Preferably, the macroporous resin column be HPD-300 type macroporous resin columns, macroporous resin column absorption in, first with
The elution flow rate of the 4-12 times of distillation water elution for measuring bed volume, distilled water is 1-2 times of column volume/hour, discards eluent；It connects
The ethanol water solvent column scrubber bed with the 20%-40% volumetric concentrations of 4-10 times of bed volume, ethanol water solvent flow velocity is
0.5-2 times of column volume/hour, discard eluent；It is water-soluble with the ethyl alcohol of 4-10 times of bed volume 45%-100% volumetric concentration again
Agent column scrubber bed, ethanol water solvent flow velocity are 0.5-2 times of column volume/hour, collect eluent, recycle ethyl alcohol and are concentrated into thick
Cream is dried to obtain the Shorthorned Epimedium P.E.
The beneficial effects of the present invention are：1. the present invention, not only will be excessive in extract using Shorthorned Epimedium P.E as raw material
Sheep leaves of pulse plants glycosides, which is converted into A Kela, to be determined, and the epimedin C in extract is also converted to A Kela and is determined, and takes full advantage of medicinal material money
Source.2. the Shorthorned Epimedium P.E of the present invention uses beta -glycosidase during enzyme digestion reaction, with existing naringinase, glusulase
It compares, beta -glycosidase hydrolyzes Shorthorned Epimedium P.E and generates the fixed conversion ratio highers of A Kela, up to 98% so that subsequent purifying
It is more prone to.And pectin enzyme hydrolysis Shorthorned Epimedium P.E generates the fixed conversion ratio highests only up to 90% of A Kela；Secondly, β-glucosides
Enzyme hydrolysis Shorthorned Epimedium P.E generates the fixed reaction speeds of A Kela faster, and reaction only needs 10-18 hours conversion ratio can be made to reach
To 98%.3. the present invention is in enzymolysis process, using buffer salt as solvent, it is Shorthorned Epimedium P.E matter to make the volume of reaction dissolvent
5-15 times of amount, substantially increases production efficiency.In addition, the present invention is other than with acetone solution filter cake, also by water come dilute
Acetone soln is released, it is not soluble in water since icariine itself is dissolved in acetone, while using the property dissolved each other between acetone and water,
The water-solubility impurity in icariine acetone soln can be effectively removed, improve the purity of icariine, icariine it is pure
Degree reaches 99.8%.Icariine after purification can reach 20% or more relative to the yield of Shorthorned Epimedium P.E.
Description of the drawings
Fig. 1 upper half figures indicate the high-efficient liquid phase chromatogram by the general flavone in 1 step 1.1 ethanol extract of embodiment.
Fig. 1 lower half figures indicate the high-efficient liquid phase color by general flavone in the ethanol extract of 1 step 1.2 of embodiment after purification
Spectrogram.
Fig. 2 indicates the preparation flow of Shorthorned Epimedium P.E of the present invention.
Fig. 3 indicates that A Kela determines the high-efficient liquid phase chromatogram of sterling.
Specific implementation mode
Unless otherwise stated, term herein " enzyme digestion reaction " refers to the hydrolysis under enzyme effect.
Unless otherwise stated, " Shorthorned Epimedium P.E " of the terms refers to extracting Herba Epimedii by ethanol water solvent
Obtained extract contains the flavones ingredient and other compositions including icariine in extract.
Unless otherwise stated, term herein " bed volume " refers to the total volume of macroporous resin column inner stuffing.
Unless otherwise stated, term herein " beta -glycosidase " is the beta -glycosidase of Tian Ye companies of Japan, trade name
For Aromase H2.
Embodiment 1
1. the preparation of Shorthorned Epimedium P.E
1.1 extraction
The present embodiment by several times extraction in addition to stem, Folium Epimedii amount to 490Kg, rubbed it is broken, respectively with 14 times, 10 times measure
(v/w) the ethanol water refluxing extraction of 40% volumetric concentration 2 times, 1 hour every time.Ethyl alcohol is recycled to extracting solution without alcohol taste, is led to
The general flavone in the high performance liquid chromatography detection extracting solution is crossed, sees 1 upper half figure of attached drawing；
1.2 macroporous resin purification
The ethanol extract that step 1.1 is obtained uses macroporous resin purification after concentration removes ethyl alcohol.First with macropore tree
The distillation water elution macroporous resin column of 8 times of fat bed volume, the flow velocity for distilling water elution is 1 times of column volume/hour, and elution terminates
Afterwards, eluent is discarded；
Macroporous resin column bed, elution knot are washed with 6 times of amount 25% ethanol water solvents of volumetric concentration of macroreticular resin bed volume
Shu Hou discards eluent；
The macroporous resin column in ethanol water solvent washing step 2 for being 70% with volumetric concentration, ethanol water solvent volume are
4 times of bed volume, adjusting ethanol water solvent flow velocity are 1 times of bed volume/hour, collect eluent at this time, are concentrated into thick
Cream, spray drying are ground into fine powder, and sieving obtains Shorthorned Epimedium P.E and amounts to 9.8Kg.The macroreticular resin that the above three-step approach obtains
Shorthorned Epimedium P.E after purification is shown in Fig. 1 lower half figures by high performance liquid chromatography detection flavone component therein.
Macroreticular resin in the present embodiment is purchased from Hebei Bao En sorbing materials Co., Ltd, model HPD-300 types.
High performance liquid chromatography (HPLC) condition：Chromatographic column：C18 columns；Mobile phase：Acetonitrile-water (is wherein containing volume fraction
0.0125% trifluoroacetic acid), gradient see the table below 1, elution time 60min, flow velocity：1.0mL/min, column temperature：35℃.It is purple
External detector Detection wavelength is respectively 254,272,320nm.
1 solvent gradient elution table of table
As a result it shows:In addition to the peak occurred when at 3 minutes is solvent peak, at 22 minutes, 24 minutes, 46 minutes and
52 minutes appearances are the peak of flavone component.
After macroporous resin purification, general flavone ingredient is effectively enriched in Shorthorned Epimedium P.E, wherein after purification excessive
The yield of general flavone reaches 2.0~10.0% in sheep leaves of pulse plants extract.
2. enzyme digestion reaction prepares icariine
The above-mentioned Shorthorned Epimedium P.E 9.8Kg by macroporous resin purification is weighed, 196L 0.5mol/L pH=are added to
In 4.7 acetic acid-sodium acetate buffer solution, mixing speed makes it dissolve in the case of being 100rpm.Wait for that system temperature is constant in 58-60
When DEG C condition, 2.0Kg beta -glycosidases are added and are stirred to react.After isothermal reaction 28 hours, stop stirring, reaction solution is cooled to 30
℃。
3. the purifying of icariine
After enzyme digestion reaction, reaction solution is centrifuged, and collects filter cake, weight is 7.59Kg after drying, is added after crushing
88.45Kg acetone, stirring are filtered after 1 hour, and being warming up to 60 DEG C after addition 64.80Kg purified waters into acetone soln keeps system molten
Agent is back to solution clarification.Solution slow cooling is filtered to keeping the temperature 2 hours after 4 DEG C, is collected filter cake and drying, is obtained Herba Epimedii
Plain crystallized product 1.96Kg, is shown in Fig. 3, is the peak of icariine in 20.403 minutes appearances.
Embodiment 2
1. enzyme digestion reaction prepares icariine
Shorthorned Epimedium P.E 10Kg purchased in market is weighed, 100L pH=5.5 disodium hydrogen phosphates-citric acid solution is added to
In, mixing speed makes it dissolve in the case of being 100rpm.When system temperature it is constant in 57 DEG C of conditions when, 1.5Kg β-glucosides is added
Enzyme is stirred to react.After isothermal reaction 16 hours, stop stirring, reaction solution is cooled to 25 DEG C.
2. the purifying of icariine
After enzyme digestion reaction, reaction solution is centrifuged, and collects filter cake, weight is 7.85Kg after drying, is added after crushing
88.11Kg acetone, stirring are filtered after 1 hour, and being warming up to 63 DEG C after addition 64.55Kg purified waters into acetone soln keeps system molten
Agent is back to solution clarification.2 hours are kept the temperature after solution slow cooling to room temperature, is filtered, filter cake and drying is collected, obtains Herba Epimedii
Plain crystallized product 1.17Kg.
Embodiment 3
1. enzyme digestion reaction prepares icariine
Shorthorned Epimedium P.E 8.7Kg purchased in market is weighed, 174L pH=4.8 citric acid-sodium citrate buffers are added to
In, mixing speed makes it dissolve in the case of being 100rpm.When system temperature it is constant in 45 DEG C of conditions when, 0.435Kg β-sugar is added
Glycosides enzyme is stirred to react.After isothermal reaction 20 hours, stop stirring, reaction solution is cooled to 30 DEG C.
2. the purifying of icariine
After enzyme digestion reaction, reaction solution is centrifuged, and collects filter cake, weight is 6.55Kg after drying, is added after crushing
76.34Kg acetone, stirring are filtered after 1 hour, and being warming up to 62 DEG C after 55.93Kg purified waters into acetone soln makes system solvent return
It flow to solution clarification.Solution slow cooling is filtered to keeping the temperature 2 hours after 25 DEG C, is collected filter cake and drying, is obtained icariine knot
Brilliant product 1.01Kg.
Embodiment 4
1. enzyme digestion reaction prepares icariine
Shorthorned Epimedium P.E 8.0Kg purchased in market is weighed, is added in 80L pH=6.0 phosphoric acid-buffer solution of sodium phosphate, is stirred
Speed makes it dissolve in the case of being 100rpm.When system temperature it is constant in 55 DEG C of conditions when, it is anti-that the stirring of 1.2Kg beta -glycosidases is added
It answers.After isothermal reaction 18 hours, stop stirring, reaction solution is cooled to 25 DEG C.
2. the purifying of icariine
After enzyme digestion reaction, reaction solution is centrifuged, and collects filter cake, weight is 6.23Kg after drying, is added after crushing
73.25Kg acetone, stirring are filtered after 1 hour, and being warming up to 64 DEG C after 53.66Kg purified waters into acetone soln makes system solvent return
It flow to solution clarification.Solution slow cooling is filtered to keeping the temperature 2 hours after 25 DEG C, is collected filter cake and drying, is obtained icariine knot
Brilliant product 1.12Kg.
Claims (12)
1. a kind of preparation method of icariine, this approach includes the following steps：
A. Shorthorned Epimedium P.E is scattered in the buffer solution that pH value is 3.5-7.5 first, and 35-65 is increased in temperature
DEG C when, carry out enzyme digestion reaction under the action of beta -glycosidase, the quality of icariin and epimedin C in the Shorthorned Epimedium P.E
Content summation is at least 5%, and quality/Kg ratios of the volume of buffer solution/L and Shorthorned Epimedium P.E are 5-30:1；
B. the enzyme digestion reaction product then obtained step a filters；
C. again by filtered filter cake acetone solution；
D. water is added into acetone soln, reflux dissolving, by solution left standstill, crystal is collected in filtering, obtains the Herba Epimedii
Element.
2. according to the method described in claim 1, it is characterized in that, in the step a, the buffer solution is pH value
Disodium hydrogen phosphate-potassium dihydrogen phosphate, acetic acid-sodium acetate buffer solution, phosphoric acid-sodium phosphate, the citric acid-citric acid of 4.0-7.0
Sodium or disodium hydrogen phosphate-citric acid solution.
3. according to the method described in claim 1, it is characterized in that, enzyme digestion reaction time described in step a is 8-48 hours,
Enzyme digestion reaction temperature is 35-65 DEG C.
4. according to the method described in claim 3, the mass ratio of the Shorthorned Epimedium P.E and beta -glycosidase in step a is 1-50：
1。
5. according to the method described in claim 4, the ratio of Shorthorned Epimedium P.E and beta -glycosidase is 2-30 in step a：1.
6. according to the method described in claim 5, the mass ratio of Shorthorned Epimedium P.E and beta -glycosidase is 5-20 in step a：1.
7. according to the method described in claim 1, it is characterized in that, in the step c, filtered filter cake is done first
It is dry, it then crushes, then the filter cake after crushing is scattered in acetone solvent and is dissolved, volume/L of acetone solvent is equivalent to powder
2-20 times of broken filter cake quality/Kg obtains acetone soln.
8. according to the method described in claim 1, it is characterized in that, in the step d, the body of water is added in acetone soln
Product/L is equivalent to 2-20 times of filter cake quality/Kg, and the solution is stood at room temperature.
9. according to the method described in claim 1, it is characterized in that, in the step a, Shorthorned Epimedium P.E is with Herba Epimedii
Chinese medicine is raw material, is made by ethonal extraction.
10. according to the method described in claim 9, it is characterized in that, the alcohol solvent be ethyl alcohol water mixed solvent, ethyl alcohol
The extract that water mixed solvent extraction Herba Epimedii Chinese medicine obtains first passes around concentration, is then adsorbed by macroporous resin column, then
The ethanol water solvent for being respectively 30%-100% with water and volumetric concentration is eluted, and obtains carrying for the Herba Epimedii of enzyme digestion reaction
Take object.
11. according to the method described in claim 10, the ethanol water in the mixed solvent, the volume ratio of second alcohol and water is 40:
10-160, volume/L of mixed solvent are 4-20 times of Herba Epimedii Chinese medicine quality/Kg, are extracted 1-5 times altogether, flow back 1-5 every time
Hour.
12. according to the method described in claim 10, the macroporous resin column is HPD-300 type macroporous resin columns, in macropore
In resin column absorption, the distillation water elution for first measuring bed volume with 4-12 times, the elution flow rate of distilled water be 1-2 times of column volume/
Hour, discard eluent；Then with the ethanol water solvent column scrubber bed of the 20%-40% volumetric concentrations of 4-10 times of bed volume,
Ethanol water solvent flow velocity is 0.5-2 times of column volume/hour, discards eluent；Again with 4-10 times of bed volume 45%-100% body
The ethanol water solvent column scrubber bed of product concentration, ethanol water solvent flow velocity are 0.5-2 times of column volume/hour, collect eluent, recycling
Ethyl alcohol is simultaneously concentrated into thick paste, is dried to obtain the Shorthorned Epimedium P.E.
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| CN108558812A (en) * | 2018-03-26 | 2018-09-21 | 北京珅奥基医药科技有限公司 | A kind of method that acidolysis prepares icariine |
| CN110699263B (en) * | 2019-10-29 | 2021-05-11 | 浙江工业大学 | Aspergillus niger YH-6 and application thereof in improving content of icaritin in epimedium |
| CN111575330B (en) * | 2020-05-21 | 2022-04-15 | 成都蓓乐康生物科技有限公司 | Method for hydrolyzing epimedium extract by plant-derived enzyme |
| CN113355373A (en) * | 2021-06-29 | 2021-09-07 | 劲牌持正堂药业有限公司 | Preparation method of low polycyclic aromatic hydrocarbon icaritin |
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| CN101302548B (en) * | 2007-05-09 | 2011-04-13 | 北京珅奥基医药科技有限公司 | Preparation of icaritin |
| CN102008533B (en) * | 2010-12-06 | 2014-02-26 | 吉林修正药业新药开发有限公司 | Medicinal application and preparation method of shorthorned epimedium P.E |
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Address after: 100085 A201 room, No. 5, Pioneer Road, Beijing, Haidian District Patentee after: Beijing shengnuoji Pharmaceutical Technology Co., Ltd Address before: 100085 A201 room, No. 5, Pioneer Road, Beijing, Haidian District Patentee before: Beijing Shengnuoji Medicine Technology Co., Ltd. |