CN106632521A - Method for extracting high-purity loganin from cornus officinalis fruits - Google Patents
Method for extracting high-purity loganin from cornus officinalis fruits Download PDFInfo
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- CN106632521A CN106632521A CN201710053870.9A CN201710053870A CN106632521A CN 106632521 A CN106632521 A CN 106632521A CN 201710053870 A CN201710053870 A CN 201710053870A CN 106632521 A CN106632521 A CN 106632521A
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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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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
The invention relates to a method for extracting high-purity loganin from cornus officinalis fruits. The method includes: using traditional Chinese medicine cornus officinalis fruits as the raw material, and performing reflux extraction, acid-reaction impurity removing, organic-solvent purification, crystallization, recrystallization and the like to obtain the loganin with the purity being larger than 95%. The method has the advantages that acid reaction is used to remove impurities which affects the crystallization, and the method is simple in process, low in production cost and suitable for large-scale industrial production.
Description
Technical field
The present invention relates to field of traditional Chinese medicine extraction, and in particular to a kind of method that loganin is purified from cornus fruit.
Background technology
Fructus Corni is that the maturation of Cornaceae plant Fructus Corni is dried pulp, is that the rare medicinal material of China's tradition is famous and precious with conventional
Chinese medicine, there is the effects such as puckery essence, arrest sweating, filling liver kidney, be usually used in treat dizziness and tinnitus, soreness of waist and knee joint, impotence and seminal emission, enuresis frequent micturition,
The diseases such as uterine bleeding under band, Heat Diabetes, are one of parts of Liuwei Dihuang Wan.Iridoid glycoside is the main activity of Fructus Corni
One of composition, loganin with hypoglycemic, anti-platelet aggregation, is exempted from as the main component of iridoid glycosides in Fructus Corni
The effect such as epidemic disease regulation, Hemorrhagic shock, anti-oxidant, suppression PECTORAL LIMB SKELETON differentiation.At present the composition has become to Fructus Corni research
Focus, with wide DEVELOPMENT PROSPECT.
From Chinese medicine Fructus Corni extract separate loganin method it is less, be mostly laboratory method, using solvent toxicity compared with
Greatly, complex steps, and preparation amount is less.Chinese invention patent " method that loganin is prepared from Chinese medicine Fructus Corni ", application number
201310415843.3, mainly heating extraction by ethanol, prepared by the step such as macroporous resin adsorption, silica gel column chromatography, recrystallization
Loganin, the patent purifies loganin using mixed solvent gradient elution by silica gel column chromatography, and solvent usage amount is big, raw
High cost is produced, is not suitable for industrial scale production.Chinese invention patent is " a kind of that morroniside and loganin are extracted from Fructus Corni
Method ", application number 201010557777.X, by high speed adverse current chromatogram separate loganin, need to use special installation, cost compared with
Greatly, it is difficult to meet the needs of industrialized production.
The content of the invention
The shortcoming that loganin extraction process is present in order to overcome prior art, it is an object of the invention to provide a kind of technique
The method that loganin is extracted from Fructus Corni of simple and suitable industrialized production.
To reach object above, the main technical schemes of the present invention are：Refluxing extraction, acid reaction removal of impurities, organic solvent are carried
The step such as pure, crystallization and recrystallization obtains highly purified loganin.
A kind of method that loganin is purified from cornus fruit, it is characterised in that mainly include the following steps that：
(1) refluxing extraction：Cornel fruit practicality hydrous ethanol refluxing extraction, extract concentration.
(2) acid reaction removal of impurities：Extract concentrate and add ethanol, make reaction system become hydrous ethanol solution, the solution exists
Acid hydrolytic reaction is carried out under heating condition, reaction terminates, plus alkaline solution is neutralized to neutrality, the concentration of neutralization reaction liquid is dried
Dried object.
(3) organic solvent purification：Organic solvent, refluxing extraction, extract is added to concentrate in step (2) gained dried object,
Dry to obtain crude product.
(4) crystallization and recrystallization：Crude crystalline and recrystallization, obtain loganin, and purity is more than 95%.
Preferably, the volume fraction of the hydrous ethanol used in step (1) is 20%-80%.
Preferably, the determining alcohol of acid reaction system is 5%-95% in step (2), and the acid solution that sour water solution is used is selected from
Any one in hydrochloric acid, sulfuric acid, acetic acid, acid adding volume is the 1/10-1/100 of question response liquid product, and acid concentration is 0.1-
3mol/L, reaction temperature is 60-90 DEG C, and the reaction time is 1-4 hours.Alkaline solution is selected from NaOH, NaHCO3、Na2CO3In
Any one.
Preferably, purification organic solvent used is any one in methyl alcohol, ethanol, acetone, ethyl acetate in step (3)
Kind.
Preferably, crystallization and any one that the solvent that recrystallization is used is methyl alcohol, ethanol, acetone in step (4).
A kind of method that loganin is purified from cornus fruit, mainly comprises the steps：
(1) refluxing extraction：Cornus fruit adds the 6-10 times of ethanol for measuring volume fraction 20%-80%, heating and refluxing extraction 2
It is secondary, 1-3 hours are extracted every time, extract is concentrated into density 1.05-1.1；
(2) acid reaction removal of impurities：Extract concentrate and add ethanol, make reaction system concentration of alcohol in 5%-95%, add acid
Solution, carries out acid reaction, and reaction temperature 60-90 DEG C, time 1-4h, reaction terminates, plus alkaline solution is neutralized to neutrality, and neutralization is anti-
Answer liquid to concentrate, dry to obtain dried object；
(3) organic solvent purification：Add ethanol, refluxing extraction, extract concentration, drying in step (2) gained dried object
Obtain crude product；
(4) crystallization and recrystallization：Loganin crude product adds ethanol heating for dissolving, filters while hot, slow cooling, separates out white brilliant
Body, continues, with ethyl alcohol recrystallization 1-3 time, to obtain loganin.
Step of the present invention is simple, easily operation, and reappearance is high, and loganin purity reaches 95-98% as obtained by this method.
Compared with the method for purification of loganin in prior art, it is an advantage of the current invention that：
(1) the step for purification process of the present invention adds acid reaction, eliminates some impurity, with other patents and document report
The loganin purifying in road compares, and does not require the use of special installation, is not required to use various organic solvents, simple and feasible, shortens purifying
Step, substantially increases the yield and purity of loganin.
(2) present invention is few using solvent species, low cost, simple production process, it is easy to operate, and is more suitable for industrialization big
Large-scale production.
Specific embodiment
The present invention is further illustrated below in conjunction with case is embodied as, the scope of protection of present invention is not limited to
Implementation below.
Embodiment 1
Fructus Corni dry fruit 1kg, plus the ethanol of 7L volume fractions 50% are taken, heating and refluxing extraction extracts twice, every time 1
Hour, merge extract twice, concentration, plus ethanol to adjust determining alcohol is 30%, plus 1/20 volume 2mol/L acetic acid, 80 DEG C of reactions
2 hours, reaction terminated, plus NaOH solution is neutralized to neutrality, and neutralizer is concentrated to dryness, and obtains dried object, and the dried object adds 400mL second
Alcohol reflux is extracted twice, 2 hours every time, and extract merges concentration, obtains loganin crude product.The crude product is heated back with 100mL methyl alcohol
Stream dissolving, insoluble matter filters while hot, and filtrate is down to room temperature, stirring and crystallizing, filtration drying, continues, with recrystallizing methanol 2 times, to obtain horse
Money glycosides 3.8g, content is 96.3%.
Embodiment 2
Fructus Corni dry fruit 1kg, plus the ethanol of 10L volume fractions 20% are taken, heating and refluxing extraction twice, is extracted every time
2 hours, merge extract twice, concentration, plus ethanol to adjust determining alcohol was 5%, plus 1/10 volume 1mol/L hydrochloric acid, 70 DEG C of reactions
3 hours, reaction terminated, plus NaHCO3Solution is neutralized to neutrality, and neutralizer is concentrated to dryness, and obtains dried object, and the dried object adds 600mL
Acetone reflux is extracted twice, 2 hours every time, and extract merges concentration, obtains loganin crude product.Crude product 200mL absolute ethyl alcohols
Dissolving is heated to reflux, insoluble matter is filtered while hot, and filtrate is down to room temperature, and stirring and crystallizing, filtration drying, continuation absolute ethyl alcohol is tied again
It is brilliant 2 times, loganin 3.2g is obtained, content is 98.1%.
Embodiment 3
Fructus Corni dry fruit 4kg, plus the ethanol of 32L volume fractions 60% are taken, heating and refluxing extraction twice, is extracted every time
2 hours, merge extract twice, concentration, plus ethanol to adjust determining alcohol was 70%, plus 1/100 volume 3mol/L hydrochloric acid, and 60 DEG C anti-
Answer 4 hours, reaction terminates, plus NaHCO3Solution is neutralized to neutrality, and neutralizer is concentrated to dryness, and obtains dried object, and the dried object adds 1L
Methanol eddy is extracted twice, 2 hours every time, and extract merges concentration, obtains loganin crude product.The crude product is heated with 800mL ethanol
Backflow dissolving, insoluble matter filters while hot, and filtrate is down to room temperature, stirring and crystallizing, filtration drying, continues, with ethyl alcohol recrystallization 2 times, to obtain
Loganin 16.2g, content is 97.2%.
Embodiment 4
Fructus Corni dry fruit 10kg, plus the ethanol of 60L volume fractions 80% are taken, heating and refluxing extraction twice, is carried every time
Take 2 hours, merge extract twice, concentration, plus ethanol to adjust determining alcohol is 95%, plus 1/10 volume 0.1mol/L sulfuric acid, 90
DEG C reaction 1 hour, reaction terminates, plus Na2CO3Solution is neutralized to neutrality, and neutralizer is concentrated to dryness, and obtains dried object, and the dried object adds
8L ethyl acetate is extracted three times, and 2 hours every time, extract merged concentration, obtains loganin crude product.The crude product is heated back with 3L acetone
Stream dissolving, insoluble matter filters while hot, and filtrate is down to room temperature, stirring and crystallizing, filtration drying, continues, with acetone recrystallization 2 times, to obtain horse
Money glycosides 36.7g, content is 95.4%.
Claims (10)
1. a kind of method that loganin is purified from cornus fruit, mainly comprises the steps：
(1) refluxing extraction：Cornel fruit practicality hydrous ethanol refluxing extraction, extract concentration；
(2) acid reaction removal of impurities：Extract concentrate and add ethanol, make reaction system become hydrous ethanol solution, the solution is in heating
Under the conditions of carry out acid hydrolytic reaction, reaction terminates, plus alkaline solution is neutralized to neutrality, the concentration of neutralization reaction liquid, dries dry
Thing；
(3) organic solvent purification：Add organic solvent, refluxing extraction, extract concentration, drying in step (2) gained dried object
Obtain crude product；
(4) crystallization and recrystallization：Crude crystalline and recrystallization, obtain loganin.
2. the method for claim 1, it is characterised in that the volume fraction of the hydrous ethanol used in step (1) is
20%-80%, the amount of addition is 6-10 with the envelope-bulk to weight ratio of Fructus Corni:1.
3. the method for claim 1, it is characterised in that the determining alcohol of the acid reaction system described in step (2) is 5%-
95%.
4. the method for claim 1, it is characterised in that the acid solution that the sour water solution described in step (2) is used is selected from
Any one in hydrochloric acid, sulfuric acid, acetic acid.
5. method as claimed in claim 4, it is characterised in that the acid adding volume described in step (2) is question response liquid product
1:10-100, acid concentration is 0.1-3mol/L.
6. the method for claim 1, it is characterised in that the reaction temperature described in step (2) is 60-90 DEG C, during reaction
Between be 1-4 hours.
7. the method for claim 1, it is characterised in that the alkaline solution described in step (2) is selected from NaOH, NaHCO3、
Na2CO3In any one.
8. the method for claim 1, it is characterised in that in step (3) purification organic solvent used be methyl alcohol, ethanol,
Any one in acetone, ethyl acetate.
9. the method for claim 1, it is characterised in that it is methyl alcohol, second that step (4) crystallizes the solvent used with recrystallization
Any one of alcohol, acetone.
10. a kind of method that loganin is purified from cornus fruit, mainly comprises the steps：
(1) refluxing extraction：Cornus fruit adds the 6-10 times of ethanol for measuring volume fraction 20%-80%, heating and refluxing extraction 2 times,
1-3 hours are extracted every time, and extract is concentrated into density 1.05-1.1；
(2) acid reaction removal of impurities：Extract concentrate and add ethanol, make reaction system concentration of alcohol in 5%-95%, add acid solution,
Acid reaction is carried out, reaction temperature 60-90 DEG C, time 1-4h, reaction terminates, plus alkaline solution is neutralized to neutrality, neutralization reaction liquid
Concentration, dries to obtain dried object；
(3) organic solvent purification：Add ethanol, refluxing extraction, extract to concentrate in step (2) gained dried object, dry slightly
Product；
(4) crystallization and recrystallization：Loganin crude product adds ethanol heating for dissolving, filters while hot, slow cooling, separates out white crystal,
Continue, with ethyl alcohol recrystallization 1-3 time, to obtain loganin.
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| CN201710053870.9A CN106632521B (en) | 2017-01-22 | 2017-01-22 | A method of purifying loganin from cornus fruit |
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| CN201710053870.9A CN106632521B (en) | 2017-01-22 | 2017-01-22 | A method of purifying loganin from cornus fruit |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440619A (en) * | 2018-01-26 | 2018-08-24 | 北京联合大学 | The method that cornel extractive prepares high-purity horse loganin |
| CN108467416A (en) * | 2018-06-21 | 2018-08-31 | 长沙爱扬医药科技有限公司 | The method that Fructus Corni extracts morroniside, loganin and ursolic acid |
| CN110742228A (en) * | 2019-10-29 | 2020-02-04 | 河南省商业科学研究所有限责任公司 | Preparation method of dogwood aqueous extract |
Citations (3)
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| CN102477053A (en) * | 2010-11-25 | 2012-05-30 | 苏州宝泽堂医药科技有限公司 | Method for extracting morroniside and loganin from Macrocarpium officinalis |
| CN103360443A (en) * | 2013-07-30 | 2013-10-23 | 天津科丝美特生物科技有限公司 | Method for extraction and purification of four iridoid glycosides in cornus officinalis |
| CN104447910A (en) * | 2013-09-13 | 2015-03-25 | 中国科学院兰州化学物理研究所 | Method for preparation of loganin from traditional Chinese medicine Cornus officinalis |
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2017
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| CN102477053A (en) * | 2010-11-25 | 2012-05-30 | 苏州宝泽堂医药科技有限公司 | Method for extracting morroniside and loganin from Macrocarpium officinalis |
| CN103360443A (en) * | 2013-07-30 | 2013-10-23 | 天津科丝美特生物科技有限公司 | Method for extraction and purification of four iridoid glycosides in cornus officinalis |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440619A (en) * | 2018-01-26 | 2018-08-24 | 北京联合大学 | The method that cornel extractive prepares high-purity horse loganin |
| CN108440619B (en) * | 2018-01-26 | 2021-02-26 | 北京联合大学 | Method for preparing loganin from dogwood extract |
| CN108467416A (en) * | 2018-06-21 | 2018-08-31 | 长沙爱扬医药科技有限公司 | The method that Fructus Corni extracts morroniside, loganin and ursolic acid |
| CN110742228A (en) * | 2019-10-29 | 2020-02-04 | 河南省商业科学研究所有限责任公司 | Preparation method of dogwood aqueous extract |
| CN110742228B (en) * | 2019-10-29 | 2022-08-26 | 河南省商业科学研究所有限责任公司 | Preparation method of dogwood aqueous extract |
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