CN109988137A - A kind of preparation method of epimedium aglucone - Google Patents
A kind of preparation method of epimedium aglucone Download PDFInfo
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- CN109988137A CN109988137A CN201711485889.7A CN201711485889A CN109988137A CN 109988137 A CN109988137 A CN 109988137A CN 201711485889 A CN201711485889 A CN 201711485889A CN 109988137 A CN109988137 A CN 109988137A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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Abstract
The invention discloses a kind of preparation methods of epimedium aglucone.The method is to be degraded using icariin as raw material by smith, and the epimedium aglucone of high-purity is prepared in purifying.The problem of present invention uses smith edman degradation Edman to prepare epimedium aglucone for the first time, and structure caused by effective solution sour water solution changes, this method is easy to operate, mild condition, product quality is high, at low cost, meets the needs of epimedium aglucone industrialized production.
Description
Technical field
The present invention relates to a kind of preparation methods of epimedium aglucone, belong to field of traditional Chinese medicine extraction.
Background technique
Herba Epimedii is Berberidaceae plant also known as Epimedium, HERBA EPIMEDII etc., is a kind of important Chinese medicine, in China
Have more than 2,000 years medicinal histories.Compendium of Material Medica is recorded, and Herba Epimedii has " mending waist and knee, hard muscles and bones, supporing yang strengthening the essence " and other effects.It is existing
For pharmaceutical test studies have shown that icariin is its main active, epimedium aglucone many aspects compared with icariin and
Icariside has stronger pharmacological activity.Epimedium aglucone mainly has estrogen-like, adjusts immune, anti-inflammatory, the promotion heart
Myocyte regenerates and breaks up, promotees sclerotin protection, promotes neural cellular differentiation, establishing-Yang, anti-liver injury and delay liver fibrosis, resist and swell
Tumor treatment for anemia and effect is obvious the effects of reduce blood glucose, and do not find that epimedium aglucone has apparent poison secondary normal cell
Effect, illustrates its safety with higher.Have wide as a kind of new, low toxicity and efficient drug, epimedium aglucone
Application space.With the discovery both at home and abroad to the new drug effect of epimedium aglucone, the international market demand of the following epimedium aglucone
It is very big.Therefore the method for preparing epimedium aglucone to high-efficiency environment friendly will widely be paid close attention to.
It so far, is mainly enzymatic isolation method, acid hydrolyzation, enzyme by the method that raw material prepares epimedium aglucone of icariin
Solution-acidolysis combines method.But yield is not high, enzymatic hydrolysis expense is again relatively high；Chemically synthesized method yield is relatively low, condition
It is more harsh, farther out away from industrialization distance.At present these preparation methods yield is small, yield is low, it is at high cost etc. due to limit
Its large-scale production and application industrially is made.
Summary of the invention
In order to overcome epimedium aglucone prepare present in disadvantage, the present invention provides a kind of simple process, environmental protection and is suitble to
The method for preparing epimedium aglucone of industrialized production.
In order to reach the goals above, main technical schemes of the invention are as follows: degraded by smith, macroporous resin adsorption is pure
Change, alcohol wash and etc. obtain the epimedium aglucone of high-purity.In Simth degradation reaction, it is contemplated that icariin structure contains
Carbon-carbon double bond and C=O bond, to avoid active double bond that the side reactions such as addition reaction occur, we avoid as far as possible occurs this
Required condition, selects suitable reagent and temperature when a little reaction, to reduce or even avoid the generation of side reaction, make reaction by
According to it is desirable that direction carry out, finally obtain high-purity epimedium aglucone.
A kind of preparation method of epimedium aglucone, which is characterized in that mainly comprise the steps that
(1) smith degrades
Solvent is added and prepares icariin solution, weak acid, which is added, makes solution acidity, then is added into icariin solution
Oxidant is protected from light at room temperature, and glycerol is added and terminates oxidation, neutralizes, be concentrated, oxidation product is obtained by extraction；It is added
Solvent dissolves oxidation product, and reducing agent is then added and terminates reaction after reaction 12-72 hours；It is added into reduction reaction liquid strong
Reaction is hydrolyzed in acid, obtains smith degradation solution；
(2) it isolates and purifies
To pH in gained smith degradation solution plus alkali, is adjusted in step (1) to neutrality, it is concentrated into no alcohol taste, then in equal volume
Ethyl acetate extraction, combining extraction liquid are concentrated and dried, obtain epimedium aglucone crude product；Epimedium aglucone crude product is used into macropore
Purifying resin, alcohol, which is washed, can be obtained epimedium aglucone.
Preferably, a kind of preparation method of epimedium aglucone, it is characterised in that mainly comprise the steps that
(1) smith degrades
Solvent is added and is configured to the solution that Icariin content is 0.001-0.1mol/L, weak acid tune PH to 3-5 is added, presses
The molar ratio of icariin and oxidant is that oxidant is added in 1:4-1:10, after being protected from light 12-72 hours at room temperature,
Glycerol is added and terminates oxidation, neutralizes, be concentrated, oxidation product is obtained by extraction；Being added with the mass ratio of icariin is 10:1-40:1
Solvent dissolve oxidation product, be then added reducing agent, the molar ratio of icariin and reducing agent is 1:4-1:10, reacts 12-
After 72 hours, reaction is terminated；Being added into reduction reaction liquid with the molar ratio of icariin is 1:2-6:1 strong acid, at 20-60 DEG C
Lower stirring 6-96 hours, obtains smith degradation solution.
(2) it isolates and purifies
To pH in gained smith degradation solution plus alkali, is adjusted in step (1) to neutrality, be concentrated into no alcohol taste use again it is isometric
Ethyl acetate extraction, combining extraction liquid are concentrated and dried, obtain epimedium aglucone crude product；Epimedium aglucone crude product is used into macropore
Purifying resin, alcohol, which is washed, can be obtained epimedium aglucone.
Preferably, the solvent that raw material is dissolved when oxidation reaction described in step (1) selects volume fraction 0-50% methanol-water
Solution or ethanol water.
Preferably, the concrete operations of extraction described in step (1) are: being added isometric with the reaction solution after being concentrated under reduced pressure
Ethyl acetate extraction；Combining extraction liquid, washing, then it is evaporated ethyl acetate.
Preferably, the solvent of dissolution oxidation product described in step (1) is the methanol aqueous solution that volume fraction is 50-95%
Or ethanol water.
Preferably, weak acid described in step (1) is acetic acid, and oxidant is sodium metaperiodate, any one in potassium metaperiodate
Kind, reducing agent is sodium borohydride, any one in potassium borohydride, and alkali is sodium hydroxide, sodium carbonate, any in sodium bicarbonate
One kind, strong acid are sulfuric acid, hydrochloric acid, any one in nitric acid.
Preferably, it is in D101, HPD200, AB-8 that middle big pore resin model is isolated and purified described in step (2)
Any one.
Beneficial achievement of the invention is as follows:
(1) effectively icariin can be reacted to obtain epimedium aglucone by smith degradation, and product is after processing
Purity successfully solves the problems, such as that structure caused by sour water solution changes up to 90% or more.
(2) whole preparation process mild condition, high income, operation is simple, environmental protection pressure is small, be suitble to industry metaplasia
It produces.
Specific embodiment
Further illustrate that the present invention, the scope of protection of present invention are not limited to below in conjunction with specific implementation case
Following implementation.
Embodiment 1
(1) 2g icariin is added 5% ethanol water solution and is configured to Icariin content and is by smith degradation
Acetic acid tune PH to 5.0 is added in 0.001mol/L solution, is that 1:4 is added into solution by the molar ratio of icariin and oxidant
Sodium metaperiodate after being protected from light 72 hours at room temperature, is added glycerol and terminates oxidation, sodium hydroxide solution tune PH is added extremely
Neutrality is extracted 3 times after being concentrated into no alcohol taste with isometric ethyl acetate, and combining extraction liquid is concentrated to dryness, and obtains oxidation product；
The dissolution of 50% ethanol water is added in oxidation product, 50% ethanol water of addition and the mass ratio of icariin are 40:
1, then it is added sodium borohydride, the molar ratio of sodium borohydride and icariin is that 4:1 terminates reaction after reaction 72 hours；To also
36% hydrochloric acid 1.2mL is added in former reaction solution, is stirred 6 hours at 60 DEG C, obtains smith degradation solution；
(2) it isolates and purifies
To adding sodium hydroxide aqueous solution, tune pH to neutrality are concentrated into no alcohol taste in gained smith degradation solution in step (1),
It is extracted 5 times with isometric ethyl acetate again, combining extraction liquid is concentrated to dryness, and obtains epimedium aglucone crude product；By excessive sheep
Leaves of pulse plants glycosides crude product uses HPD200 macroporous resin purification, collects 95% ethanol eluate, can be obtained after eluent is concentrated and dried
The epimedium aglucone of purity 90%.
Embodiment 2
(1) 2g icariin is added 20% ethanol water and is configured to Icariin content and is by smith degradation
Acetic acid tune PH to 4.0 is added in the solution of 0.02mol/L, is that 1:6 is added into solution by the molar ratio of icariin and oxidant
Potassium metaperiodate after being protected from light 48 hours at room temperature, is added glycerol and terminates oxidation, add sodium carbonate tune PH to neutrality, dense
It is extracted 3 times after being reduced to no alcohol taste with isometric ethyl acetate, combining extraction liquid is concentrated to dryness to obtain oxidation product；By oxidation product
70% ethanol water is added, 70% ethanol water of addition and the mass ratio of icariin are 20:1；Then boron hydrogen is added
The molar ratio of change potassium, potassium borohydride and icariin is that 6:1 terminates reduction reaction after reaction 48 hours；Into reduction reaction liquid
5% sulfuric acid 5.4mL is added, is stirred 24 hours at 40 DEG C, obtains smith degradation solution；
(2) it isolates and purifies
To pH in gained smith degradation solution plus sodium carbonate, is adjusted in step (1) to neutrality, be concentrated into no alcohol taste, then with etc. bodies
Long-pending ethyl acetate extracts 4 times, and combining extraction liquid is concentrated to dryness, and obtains epimedium aglucone crude product；By icariin crude product
Using D101 macroporous resin purification, water, 30% ethyl alcohol is successively used to rinse icariin crude product, then dissolved with dehydrated alcohol,
It filters, the epimedium aglucone of purity 93% can be obtained after filtrate is concentrated and dried.
Embodiment 3
(1) 2g icariin is added 50% ethanol water and is configured to Icariin content and is by smith degradation
Acetic acid tune PH to 3.9 is added in the solution of 0.08mol/L, is that 1:10 adds into solution by the molar ratio of icariin and oxidant
Enter sodium metaperiodate, after being protected from light 12 hours at room temperature, glycerol is added and terminates oxidation, adds sodium bicarbonate tune PH into
Property, it is extracted 3 times after being concentrated into no alcohol taste with isometric ethyl acetate, extract liquor merges, and is concentrated to dryness to obtain oxidation product；By oxygen
Change product and 90% ethanol water is added, 90% ethanol water of addition and the mass ratio of icariin are 10:1；Then plus
Enter sodium borohydride, the molar ratio of sodium borohydride and icariin is that 8:1 terminates reduction reaction after reaction 36 hours；It is anti-to reduction
It answers and 5% nitric acid 8mL is added in liquid, stirred 12 hours at 60 DEG C, obtain smith degradation solution；
(2) it isolates and purifies
To pH in gained smith degradation solution plus sodium bicarbonate, is adjusted in step (1) to neutrality, it is concentrated into no alcohol taste, then with etc.
The ethyl acetate of volume extracts 3 times, and combining extraction liquid is concentrated to dryness, and obtains epimedium aglucone crude product；Icariin is thick
Product use D101 macroporous resin purification, collect 95% ethanol eluate, purity 93% can be obtained after eluent is concentrated and dried
Epimedium aglucone.
Embodiment 4
(1) 2g icariin is added 30% methanol aqueous solution and is configured to Icariin content and is by smith degradation
The solution of 0.05mol/L, it is that 1:8 is added into solution that acetic acid tune PH to 3.0, which is added, by the molar ratio of icariin and oxidant
Sodium metaperiodate after being protected from light 36 hours at room temperature, is added glycerol and terminates oxidation, adding sodium hydroxide solution tune PH is into
Property, it is extracted 5 times after being concentrated into no alcohol taste with isometric ethyl acetate, combining extraction liquid is concentrated to dryness to obtain oxidation product；By oxygen
Change product and 70% ethanol water is added, 70% ethanol water of addition and the mass ratio of icariin are 20:1；Then plus
Enter sodium borohydride, the molar ratio of sodium borohydride and icariin is that 8:1 terminates reduction reaction after reaction 24 hours；It is anti-to reduction
It answers and 36% hydrochloric acid 3mL is added in liquid, stirred 96 hours under 40 DEG C of parts, obtain smith degradation solution；(2) it isolates and purifies
To adding sodium hydroxide in gained smith degradation solution in step (1), pH is adjusted to neutrality, is concentrated into no alcohol taste, then with etc.
The ethyl acetate of volume extracts 3 times, and combining extraction liquid is concentrated to dryness, and obtains epimedium aglucone crude product；Icariin is thick
Product use AB-8 macroporous resin purification, collect 95% ethanol eluate, purity 92% can be obtained after eluent is concentrated and dried
Epimedium aglucone.
Embodiment 5
(1) 2g icariin addition water is configured to the solution that Icariin content is 0.001mol/L by smith degradation, is added
Enter acetic acid tune PH to 3.8, is that potassium metaperiodate is added into solution by 1:5 by the molar ratio of icariin and oxidant, in room temperature item
After being protected from light 72 hours under part, glycerol is added and terminates oxidation, adds sodium carbonate tune PH to neutrality, be concentrated into after no alcohol taste with etc. bodies
Long-pending ethyl acetate extracts 3 times, and combining extraction liquid is concentrated to dryness to obtain oxidation product；It is water-soluble that 95% ethyl alcohol is added in oxidation product
Liquid, 95% ethanol water of addition and the mass ratio of icariin are 10:1；Then be added potassium borohydride, potassium borohydride with it is excessive
The molar ratio of sheep leaves of pulse plants glycosides is that 10:1 terminates reduction reaction after reaction 12 hours；36% hydrochloric acid is added into reduction reaction liquid
2.8mL and water 16.2ml stirs 24 hours at 60 DEG C, obtains smith degradation solution；
(2) it isolates and purifies
To pH in gained smith degradation solution plus sodium carbonate, is adjusted in step (1) to neutrality, be concentrated into no alcohol taste, then with etc. bodies
Long-pending ethyl acetate extracts 4 times, and combining extraction liquid is concentrated to dryness, and obtains epimedium aglucone crude product；By icariin crude product
Using D101 macroporous resin purification, 95% ethanol eluate is collected, purity 91% can be obtained after eluent is concentrated and dried
Epimedium aglucone.
Embodiment 6
(1) 2g icariin is added 40% methanol aqueous solution and is configured to Icariin content and is by smith degradation
Acetic acid tune PH to 4.0 is added in the solution of 0.06mol/L, is that 1:6 is added into solution by the molar ratio of icariin and oxidant
Sodium metaperiodate after being protected from light 48 hours at room temperature, is added glycerol and terminates oxidation, add sodium carbonate tune PH to neutrality, dense
It is extracted 3 times after being reduced to no alcohol taste with isometric ethyl acetate, combining extraction liquid is concentrated to dryness to obtain oxidation product；By oxidation product
80% methanol aqueous solution is added, 80% methanol aqueous solution of addition and the mass ratio of icariin are 15:1；Then boron hydrogen is added
The molar ratio of change sodium, sodium borohydride and icariin is that 10:1 terminates reduction reaction after reaction 12 hours；To reduction reaction liquid
5% sulfuric acid 6.0mL of middle addition, stirs 36 hours at 40 DEG C, obtains smith degradation solution；
(2) it isolates and purifies
To pH in gained smith degradation solution plus sodium carbonate, is adjusted in step (1) to neutrality, be concentrated into no alcohol taste, then with etc. bodies
Long-pending ethyl acetate extracts 3 times, and combining extraction liquid is concentrated to dryness, and obtains epimedium aglucone crude product；By icariin crude product
Using HPD200 macroporous resin purification, 95% ethanol eluate is collected, purity 92% can be obtained after eluent is concentrated and dried
Epimedium aglucone.
Claims (10)
1. a kind of method for preparing epimedium aglucone with smith degradation.
2. preparation method as described in claim 1, which is characterized in that mainly comprise the steps that
(1) smith degrades
Solvent is added and prepares icariin solution, weak acid, which is added, makes solution acidity, then oxidation is added into icariin solution
Agent is protected from light at room temperature, and glycerol is added and terminates oxidation, neutralizes, be concentrated, oxidation product is obtained by extraction；Solvent is added
Oxidation product is dissolved, reducing agent is then added and is reacted, after reaction terminating；Strong acid is added into reduction reaction liquid, carries out water
Solution reaction, obtains smith degradation solution；
(2) it isolates and purifies
Into smith degradation solution obtained in step (1) plus alkali, tune pH are concentrated into no alcohol taste and use isometric second again to neutrality
Acetoacetic ester extraction, combining extraction liquid are concentrated and dried, obtain epimedium aglucone crude product；Epimedium aglucone crude product is used into macroreticular resin
Purifying, alcohol, which is washed, can be obtained epimedium aglucone.
3. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that prepare excessive sheep in the step (1)
Leaves of pulse plants glycosides solution solvent for use selects 0-50% methanol aqueous solution or ethanol water.
4. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that icariin in the step (1)
The concentration of solution is 0.001-0.1mol/L, and the molar ratio of the oxidant of icariin and addition is 1:4-1:10, reaction time
It is 12-72 hours.
5. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that extraction oxidation in the step (1)
The concrete operations of product are: being added and extract with the isometric ethyl acetate of the reaction solution after reduced pressure；Combining extraction liquid, water
It washes, then is evaporated ethyl acetate.
6. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that dissolution oxidation in the step (1)
The solvent of product is the methanol aqueous solution or ethanol water that volume fraction is 50-95%, and the mass ratio with icariin is 10:
1-40:1。
7. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that reduction reaction in the step (1)
In, the molar ratio of icariin and reducing agent is 1:4-1:10.
8. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that hydrolysis in the step (1)
Concrete operations are as follows: be added with icariin molar ratio be 1:2-6:1 strong acid, be stirred to react at 20-60 DEG C 6-96 hours.
9. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that the weak acid is acetic acid, oxidation
Agent is sodium metaperiodate, any one in potassium metaperiodate, and reducing agent is sodium borohydride, any one in potassium borohydride, and alkali is
Sodium hydroxide, sodium carbonate, any one in sodium bicarbonate, strong acid are sulfuric acid, hydrochloric acid, any one in nitric acid.
10. the preparation method of epimedium aglucone as claimed in claim 2, which is characterized in that during the step (2) isolates and purifies
Big pore resin model is any one in D101, HPD200, AB-8.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101760487A (en) * | 2009-08-18 | 2010-06-30 | 江苏省中医药研究院 | Preparation method of epimedium aglycone |
| CN106831695A (en) * | 2017-01-22 | 2017-06-13 | 鲁南制药集团股份有限公司 | A kind of preparation method of Strychnos nux-vomica aglycon |
-
2017
- 2017-12-30 CN CN201711485889.7A patent/CN109988137A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101760487A (en) * | 2009-08-18 | 2010-06-30 | 江苏省中医药研究院 | Preparation method of epimedium aglycone |
| CN106831695A (en) * | 2017-01-22 | 2017-06-13 | 鲁南制药集团股份有限公司 | A kind of preparation method of Strychnos nux-vomica aglycon |
Non-Patent Citations (3)
| Title |
|---|
| 南敏伦等: "淫羊藿苷元制备方法及药理活性研究进展", 《中国实验方剂学杂志》 * |
| 贾东升等: "蜗牛酶转化淫羊藿苷制备淫羊藿苷元的研究", 《中国中药杂志》 * |
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