CN1865273A - Method for extracting multiple liquorice flavone form liquorice - Google Patents
Method for extracting multiple liquorice flavone form liquorice Download PDFInfo
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- CN1865273A CN1865273A CN 200510072472 CN200510072472A CN1865273A CN 1865273 A CN1865273 A CN 1865273A CN 200510072472 CN200510072472 CN 200510072472 CN 200510072472 A CN200510072472 A CN 200510072472A CN 1865273 A CN1865273 A CN 1865273A
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Abstract
The invention discloses a multi-flavone component extracting and purifying method from liquorice, which comprises the following steps: 1. extracting and condensing glycyrol liquid; 2. adsorbing through large-hole resin; eluting the water and alcohol gradient; 3. remaining eluent of different density alcohol to continue different technologies( freezing, adding concentrated sulfuric acid-carbinol to do reflux hydrolysis; adding 80-100 order polyamide column; eluting water and carbinol; passing Sephadex LH-20 column; eluting again to produce multi-flavone component within iquiritin, liquiritigenin, isoliquiritin and isoliquiritin glucose apiin).
Description
Technical field
The present invention relates to a kind ofly from Chinese medicinal materials, to extract, the method for purifying pharmacological component, especially a kind of novel method of from Radix Glycyrrhizae, extracting multiple flavone components such as purifying liquorice glucoside, Liquiritigenin, Isoliquiritin, isoliquiritigenin glucose apiin.
Background technology
Radix Glycyrrhizae is called " with middle agent ", " blender " by many traditional Chinese medical science medical books, almost be used in all Chinese medicine preparations, is used for cooperating with other Chinese medicinal materials of mediation playing a role.For Chinese materia medica is gone to the world, now various Chinese medicinal materialss are comprised the research of Radix Glycyrrhizae is more and more goed deep into careful, different with the conventional practice of using all herbal medicine, present trend is that the various Chinese medicinal materialss of research contain which activeconstituents and the independently pharmacological action separately of these compositions, so that targetedly this kind composition is extracted separately on this basis be used for clinical, the significant curative effect in the hope of obtaining more clear and definite.In recent years pharmacological testing shows, many compositions of Radix Glycyrrhizae have good anti-oxidant activity, and the modern biomedical result of study shows, the free-radical oxidn damage relates to or directly caused the generation of many important diseases.Pharmacological testing also shows, has biological activitys such as antiulcer agent, antitumor, antispastic, antiviral, anti-arrhythmia as the licoflavone of Radix Glycyrrhizae main active ingredient.Licoflavone is the general name of a big class active substance in the Radix Glycyrrhizae, and it is grouped into by many different one-tenth again, and the pharmacological action of every kind of composition is different separately again, extracts the various licoflavone composition of purifying in order to study with application need.
Publication number is 1477104 patent document in the prior art
Document 1" yellow Radix Glycyrrhizae The Chemical Constituents " (carries " Acta Pharmaceutica Sinica ", 1989,24 (7): 525-531)
Document 2(carry " Botany Gazette ", 1991,33 (4): 314-322) with " chemical ingredients of yellow Radix Glycyrrhizae (II) "
Document 32 pieces of articles, introduced the method for extracting the various different flavone components of purifying, but their method has all been used poisonous and hazardous organic solvent for example trichloromethane, methylene dichloride etc., pollutes the environment on the one hand, and residual in extract also can make the application of extract be restricted on the other hand.There is the method for document 1 to use expensive special-purpose ultrafiltration apparatus and mould material again, the method technical process complexity of document 2,3, the production cycle is long, and yield is low, need expend a large amount of organic solvents, makes their production cost all than higher.
Summary of the invention
At above-mentioned problems of the prior art, the purpose of this invention is to provide and do not use poisonous and hazardous trichloromethane, methylene dichloride in a kind of production process, technical process simultaneously is simple, the method of flavone components such as the extraction purifying liquorice glucoside of lower cost, Liquiritigenin, Isoliquiritin, isoliquiritigenin glucose apiin, this method not only can reduce the pollution of extract and environment but also can increase economic efficiency.
Technical scheme of the present invention following (referring to accompanying drawing " process flow sheet "):
1) pre-treatment
A) Radix Glycyrrhizae is pulverized; B) use 70-80% alcohol at normal temperature supersound extraction twice; C) with 200 order nylon filter cloth coarse filtration, 5, centrifugal about 10 minutes of 000rmp; D) centrifuged supernatant concentrating under reduced pressure (0.05MPa, 50 ℃) boils off ethanol to 1/10 volume.
2) crosslinked polystyrene macroporous adsorptive resins absorption, wash-out
A) cross-linked polystyrene resin (physical parameter: particle size range 0.3～1.25mm, specific surface 100～120m is filled in macroporous resin column absorption on the concentrated supernatant in the macroporous resin column
2/ g, mean pore size 280～300 , pore volume 0.78～0.82ml/g);
B) water, 10-50% ethanol gradient elution successively.
3) continue the different process process with flavone components such as difference purifying liquorice glucoside, Liquiritigenin, Isoliquiritin, isoliquiritigenin glucose apiins, wherein:
3A) get 30% ethanol eluate,, separate out Liquiritin through 4 ℃ of refrigerations.
3B) a) get 30% ethanol eluate,, separate out Liquiritin through 4 ℃ of refrigerations; B) adding contains 5% vitriol oil, 40% methanol in water back hydrolysis 1.5 hours; C) cross Sephadex LH-20 post; D) water successively, 10-50% methyl alcohol gradient elution; E) 50% meoh eluate is separated out Liquiritigenin through 4 ℃ of refrigerations.
3C) a) get 50% ethanol eluate, concentrate, boil off ethanol; B) 80-100 order polyamide column on the concentrated solution; C) water, 5-60% methyl alcohol gradient elution successively; D) get 60% meoh eluate, concentrating under reduced pressure; E) cross Sephadex LH-20 post; F) with 40-70% methyl alcohol gradient elution; G) on pillar, be divided into two xanchromatic colour bands from upper prop liquid, collect respectively and wash 70% meoh eluate of two colour bands off and, obtain Isoliquiritin, isoliquiritigenin glucose apiin respectively through concentrating under reduced pressure.
Beneficial effect
1, the present invention does not use methylene dichloride fully, and any poisonous and hazardous organic solvent such as trichloromethane can guarantee that extract and environment are not contaminated.
2, we use the present invention and the method for using document 1 and document 2,3 to do the extraction simultaneous test, the consumption of test-results organic solvent following respectively (calculating to extract 1 kilogram of Radix Glycyrrhizae):
Document 1 method: 95% ethanol (10L), trichloromethane (3000mL), methyl alcohol (300mL).
Document 2,3 methods: 95% ethanol (15L), sherwood oil (800mL), methylene dichloride (2000mL), ethyl acetate (1000mL), propyl carbinol (1000mL), methyl alcohol (2000mL).
The present invention: 95% ethanol (10L), methyl alcohol (2000mL).
The present invention can save a large amount of organic solvents as can be seen, thereby reduces production costs.
3, the relative document 1 of the present invention need not special-purpose ultrafiltration apparatus, can reduce production costs greatly
Description of drawings
Accompanying drawing is the process flow sheet that extracts the multiple licoflavone composition of purifying from Radix Glycyrrhizae.Method of the present invention can be extracted at least 4 kinds of licoflavone compositions of purifying, is respectively Liquiritin, Liquiritigenin, Isoliquiritin and isoliquiritigenin glucose apiin.The preceding part of their extraction and purification processes is a common, all will be through extracting and concentrate the glycyrol extract by Radix Glycyrrhizae, last crosslinked polystyrene macroporous adsorptive resins absorption, water, 10-50% ethanol gradient elution.A back part then is to get the Different concentrations of alcohol elutriant, continues different technological processs respectively again, obtains 4 kinds of different licoflavone compositions, methods then.
Embodiment
Embodiment one (referring to accompanying drawing " process flow sheet "):
Getting Glycyrrhiza uralensis Fisch. 1kg pulverizes, insert 10000mL 70% alcohol at normal temperature supersound extraction twice, each 30min is with 200 order nylon filter cloth coarse filtration, 5, centrifugal 10 minutes of 000rmp, centrifuged supernatant concentrating under reduced pressure (0.05MPa, 50 ℃), boil off ethanol to 1/10 volume, get on the concentrated supernatant macroporous resin column absorption (filling cross-linked polystyrene resin), water, 10-30% ethanol gradient elution successively, elution flow rate is 1.5BV/h.Use HPLC or TLC inspection to know effluent liquid, be washed till when in effluent liquid, can't check essential substance and end.Get 30% ethanol eluate through 4 ℃ of refrigerations, separate out Liquiritin 14g.
Embodiment two (referring to accompanying drawing " process flow sheet "):
The Liquiritin 1g that embodiment draws before getting, insert 50 milliliters and contain 5% vitriol oil, 40% methanol in water back hydrolysis 1.5 hours, concentrating under reduced pressure (0.05MPa, 50 ℃), boil off methyl alcohol to 1/10 volume, cross Sephadex LH-20 post, water successively, 10-50% methyl alcohol normal pressure wash-out, use HPLC or TLC inspection to know effluent liquid, be washed till when in effluent liquid, can't check essential substance and end.Get 50% meoh eluate through 4 ℃ of refrigerations, separate out white needle Liquiritigenin 0.25g.
Embodiment three (referring to accompanying drawing " process flow sheet "):
Getting Glycyrrhiza uralensis Fisch. 1kg pulverizes, insert 10000mL 80% alcohol at normal temperature supersound extraction twice, each 30min, with 200 order nylon filter cloth coarse filtration, 5, centrifugal 10 minutes of 000rmp, centrifuged supernatant concentrating under reduced pressure (0.05MPa, 50 ℃), boil off ethanol to 1/10 volume, get macroporous resin column absorption on the concentrated supernatant, water successively, the 10-50% ethanol gradient elution, get 50% ethanol eluate, concentrate and boil off ethanol, 80-100 order polyamide column on the concentrated solution, water successively, 5-60% methyl alcohol normal pressure gradient elution, get 60% meoh eluate concentrating under reduced pressure, cross Sephadex LH-20 post, with 40-70% methyl alcohol normal pressure gradient elution, on pillar, be divided into the beginning of two xanchromatic colour bands from upper prop liquid, collect 70% meoh eluate, the elutriant that washes out two yellow colour bands is collected respectively, obtain Isoliquiritin and isoliquiritigenin glucose apiin respectively through concentrating under reduced pressure.
Claims (7)
1. the method for extraction, purifying liquorice glucoside from a Radix Glycyrrhizae is characterized in that in turn including the following steps,
1) extraction and concentrated glycyrol extract: Radix Glycyrrhizae is pulverized, use ethanol ultrasonic extraction, coarse filtration, centrifugal, the centrifuged supernatant concentrating under reduced pressure;
2) macroporous adsorptive resins absorption, wash-out: the absorption of crosslinked polystyrene macroporous adsorptive resins, water, 10-50% ethanol gradient elution successively on the concentrated supernatant;
3) get 30% ethanol eluate,, separate out Liquiritin through 4 ℃ of refrigerations.
2. an extraction from Radix Glycyrrhizae, purifying, hydrolysis prepare the method for Liquiritigenin, it is characterized in that in turn including the following steps,
1) extraction and concentrated glycyrol extract: Radix Glycyrrhizae is pulverized, use ethanol ultrasonic extraction, coarse filtration, centrifugal, the centrifuged supernatant concentrating under reduced pressure;
2) macroporous adsorptive resins absorption, wash-out: the absorption of crosslinked polystyrene macroporous adsorptive resins, water, 10-50% ethanol gradient elution successively on the concentrated supernatant;
3) get 30% ethanol eluate, through 4 ℃ of refrigerations; 4) get precipitate and add the vitriol oil-methanol eddy hydrolysis; 5) cross the SephadexLH-20 post; 6) water successively, 10-50% methyl alcohol gradient elution; 7) get 50% meoh eluate through 4 ℃ of refrigerations, separate out Liquiritigenin.
3. the method for extraction, purifying Isoliquiritin and isoliquiritigenin glucose apiin from a Radix Glycyrrhizae is characterized in that in turn including the following steps,
1) extraction and concentrated glycyrol extract: Radix Glycyrrhizae is pulverized, use ethanol ultrasonic extraction, coarse filtration, centrifugal, the centrifuged supernatant concentrating under reduced pressure;
2) macroporous adsorptive resins absorption, wash-out: the absorption of crosslinked polystyrene macroporous adsorptive resins, water, 10-50% ethanol gradient elution successively on the concentrated supernatant;
3) get 50% ethanol eluate, concentrate, boil off ethanol; 4) 80-100 order polyamide column on the concentrated solution; 5) water, 5-60% methyl alcohol gradient elution successively; 6) get 60% meoh eluate, concentrating under reduced pressure; 7) cross Sephadex LH-20 post; 8) with 40-70% methyl alcohol gradient elution; 9) collect the specific part of 70% meoh eluate and concentrate respectively; 10) obtain Isoliquiritin, isoliquiritigenin glucose apiin respectively.
According to claim 1,2,3 describedly from Radix Glycyrrhizae, extract, the method for purifying liquorice flavone component, it is characterized in that the ethanol ultrasonic extraction in described step 1) is to use twice of 70-80% alcohol at normal temperature supersound extraction, each 30min, the centrifuged supernatant concentrating under reduced pressure is to boil off ethanol to the volume that is not more than original 1/10.
According to claim 1,2,3 describedly from Radix Glycyrrhizae, extract, the method for purifying liquorice flavone component, it is characterized in that in described step 2) in the macroporous resin column packed be cross-linked polystyrene resin (physical parameter: particle size range 0.3～1.25mm, specific surface 100～120m
2/ g, mean pore size 280～300 , pore volume 0.78～0.82ml/g).
6. the method that according to claim 2ly extract from Radix Glycyrrhizae, the purifying hydrolysis prepares Liquiritigenin, what it is characterized in that adding in described step 4) is to contain 5% vitriol oil, 40% methanol in water, back hydrolysis 1.5 hours.
7. according to claim 3ly from Radix Glycyrrhizae, extract, the method for purifying Isoliquiritin and isoliquiritigenin glucose apiin, it is characterized in that collecting the specific part of 70% meoh eluate in the described step 9) respectively and concentrating, be meant from upper prop liquid to be divided into two xanchromatic colour bands, begin to collect respectively that two portions 70% meoh eluate of washing two colour bands off and also concentrate at pillar.
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100447147C (en) * | 2006-12-20 | 2008-12-31 | 福州大学 | Aminoglycoside antibiotics enriching and purifying macroporous resin process |
| CN101982465A (en) * | 2010-09-17 | 2011-03-02 | 宁夏回族自治区药品检验所 | Flavonoid compound extracted from liquorice and preparation method and application thereof |
| CN101084985B (en) * | 2006-06-09 | 2011-05-18 | 北京未名宝生物科技有限公司 | separation and identification of highly effective antibiotic anti-oxidant active part of glycyrrhiza |
| CN102336791A (en) * | 2011-09-27 | 2012-02-01 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting isoliquiritin from licorice root |
| CN102391232A (en) * | 2011-09-26 | 2012-03-28 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting liquiritigenin from liquorice |
| CN102391330A (en) * | 2011-09-26 | 2012-03-28 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting liquiritin from liquorice |
| CN103833806A (en) * | 2012-11-22 | 2014-06-04 | 天津药物研究院 | Preparation method of traditional Chinese medicine chemical component |
| CN104722100A (en) * | 2015-03-18 | 2015-06-24 | 李�杰 | Process for dynamically adsorbing peanut shell flavonoid crude extract by AB-8 macroporous resin |
| CN105777521A (en) * | 2016-05-11 | 2016-07-20 | 西安兴博凯生物科技有限责任公司 | Industrial separating and purifying method for licoflavone series monomer |
| CN105918422A (en) * | 2016-04-22 | 2016-09-07 | 华南理工大学 | Glycyrrhiza glabra leaf extract for improving quality of cold-stored pork products and frozen-stored pork products and preparation method of glycyrrhiza glabra leaf extract |
| CN108176079A (en) * | 2017-12-29 | 2018-06-19 | 无限极（中国）有限公司 | A kind of discoloration method of licorice |
| CN111588745A (en) * | 2020-06-01 | 2020-08-28 | 安徽大学 | Purification process of liquorice overground part total flavonoids by HPD-100 macroporous resin |
| CN112094306A (en) * | 2020-11-18 | 2020-12-18 | 大湾汉唯(广州)医药科技集团有限公司 | An extract containing liquiritin and its preparation method |
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- 2005-05-16 CN CN 200510072472 patent/CN1865273A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101084985B (en) * | 2006-06-09 | 2011-05-18 | 北京未名宝生物科技有限公司 | separation and identification of highly effective antibiotic anti-oxidant active part of glycyrrhiza |
| CN100447147C (en) * | 2006-12-20 | 2008-12-31 | 福州大学 | Aminoglycoside antibiotics enriching and purifying macroporous resin process |
| CN101982465A (en) * | 2010-09-17 | 2011-03-02 | 宁夏回族自治区药品检验所 | Flavonoid compound extracted from liquorice and preparation method and application thereof |
| CN102391232B (en) * | 2011-09-26 | 2015-09-30 | 天津市尖峰天然产物研究开发有限公司 | The method of Liquiritigenin is extracted from Radix Glycyrrhizae |
| CN102391232A (en) * | 2011-09-26 | 2012-03-28 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting liquiritigenin from liquorice |
| CN102391330A (en) * | 2011-09-26 | 2012-03-28 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting liquiritin from liquorice |
| CN102336791A (en) * | 2011-09-27 | 2012-02-01 | 天津市尖峰天然产物研究开发有限公司 | Method for extracting isoliquiritin from licorice root |
| CN103833806A (en) * | 2012-11-22 | 2014-06-04 | 天津药物研究院 | Preparation method of traditional Chinese medicine chemical component |
| CN104722100A (en) * | 2015-03-18 | 2015-06-24 | 李�杰 | Process for dynamically adsorbing peanut shell flavonoid crude extract by AB-8 macroporous resin |
| CN104722100B (en) * | 2015-03-18 | 2017-03-08 | 南阳理工学院 | AB 8 macroporous resin is to peanut shell flavone crude extract Kinetic adsorption |
| CN105918422A (en) * | 2016-04-22 | 2016-09-07 | 华南理工大学 | Glycyrrhiza glabra leaf extract for improving quality of cold-stored pork products and frozen-stored pork products and preparation method of glycyrrhiza glabra leaf extract |
| CN105777521A (en) * | 2016-05-11 | 2016-07-20 | 西安兴博凯生物科技有限责任公司 | Industrial separating and purifying method for licoflavone series monomer |
| CN108176079A (en) * | 2017-12-29 | 2018-06-19 | 无限极（中国）有限公司 | A kind of discoloration method of licorice |
| CN108176079B (en) * | 2017-12-29 | 2021-04-27 | 无限极（中国）有限公司 | A method for decolorizing Glycyrrhrizae radix extract |
| CN111588745A (en) * | 2020-06-01 | 2020-08-28 | 安徽大学 | Purification process of liquorice overground part total flavonoids by HPD-100 macroporous resin |
| CN112094306A (en) * | 2020-11-18 | 2020-12-18 | 大湾汉唯(广州)医药科技集团有限公司 | An extract containing liquiritin and its preparation method |
| CN112094306B (en) * | 2020-11-18 | 2021-03-09 | 大湾汉唯(广州)医药科技集团有限公司 | An extract containing liquiritin and its preparation method |
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