CN101289480B - Method for separating and preparing liquiritin - Google Patents
Method for separating and preparing liquiritin Download PDFInfo
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- CN101289480B CN101289480B CN2007100110410A CN200710011041A CN101289480B CN 101289480 B CN101289480 B CN 101289480B CN 2007100110410 A CN2007100110410 A CN 2007100110410A CN 200710011041 A CN200710011041 A CN 200710011041A CN 101289480 B CN101289480 B CN 101289480B
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Abstract
The invention relates to the separation of natural medicines, in particular to a separation and preparation method of liquiritin; wherein, extracting solution is obtained by decocting the ground licorice plants with ten times of water, and then extract is obtained after the extracting solution is concentrated, and then ethanol is added for alcohol precipitation twice, and then a 6000Da molecular weight membrane separator is used for separating the extract, and then membrane separation permeation liquid is separated by X-5 macro-porous absorption resin and is eluted with the ethanol water, and the obtained macro-porous resin separation components are separated by an efficient industrial chromatographic column and eluted with gradients with the methanol water and then the liquiritin is obtained by collecting, concentrating, freezing and drying the eluting solution. The method is high in product purity, great in preparation amount and stable and reliable in process and especially suitable for separating and preparing great amount of highly purified liquiritin compounds from the traditional Chinese medicine licorice.
Description
Technical field
The present invention relates to the separation of natural drug, a kind of method for separating and preparing of liquirtin specifically separates the preparation method of liquirtin from the traditional Chinese medicine Radix Glycyrrhizae by industry chromatography technique.
Background technology
Radix Glycyrrhizae is the root and the root stock of pulse family (Leguminosae) Glycyrrhiza (Glycyrrhiza Linn.) plant Glycyrrhiza uralensis Fisch., glycyrrhiza glabra, glycyrrhiza inflate bat, distributes all over each continent, the whole world, and be many with the Eurasia.China mainly is distributed in each provinces and regions to the north of the Huanghe valley, and indivedual the kind sees northwestern Yunnan Province.Licorice is flat, flavor is sweet, the function of tool tonifying spleen, moistening lung, detoxifcation, coordinating the actions of various ingredients in a prescription.In recent years by having discovered many new pharmacological actions, that Radix Glycyrrhizae has is anti-oxidant, antiulcer agent, to the body two-ways regulation, antiviral, antitumor and protect the liver, biological medical action (HanLano T such as anti-arrhythmia, etal..ChemPharm Bull.1988,36 (6): 2090; Shibata S.Planla Med.1991,57 (3): 221; Ma Jing. cancer, 2001,20 (8): 806-811.) competitively develop, develop Radix Glycyrrhizae medicine and food in recent years both at home and abroad.
Liquirtin, English name liquiritin, systematic naming method is: 4 ', 7-dihydroxyl flavanone-4 '-O-β-D-glucopyranoside.The bibliographical information liquirtin be Radix Glycyrrhizae main component (Yan Yonghong etc. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2006,31 (12): 1019-1021).Liquirtin is a main active ingredient in the Radix Glycyrrhizae, have anti-oxidant, anti-arrhythmia, antiulcer agent, antiviral, etc. effect, be a kind of environmental adaptation unit medicine that DEVELOPMENT PROSPECT arranged very much (Xing Guoxiu etc. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2003,26 (7): 593-597; Fu Naiwu etc. Pharmacology and Clinics of Chinese Materia Medica, 1994 (5): 26-29).The report of the extraction separation of the relevant liquirtin of document preparation, all be basically take methods such as traditional solvent extraction, silica gel column chromatography (Zhu Xumin etc. herbal medicine, 2003,34 (3): 199-201; Liu Qin etc. Acta Pharmaceutica Sinica .1989,24 (7): 525-531; Nakanishi T et al.Phytochemistry, 1985,24 (2): 339), these methods exist that product purity is low, poor reproducibility, length consuming time, organic residual serious, can't scale operation etc. shortcoming.
Summary of the invention
The purpose of this invention is to provide a kind of product purity height, favorable reproducibility, liquirtin method for separating and preparing that can scale operation.To satisfy the needs of preparation of liquirtin compound standard substance and large-scale commercial production.
For achieving the above object, the technical solution used in the present invention is:
1) extract: take by weighing the Radix Glycyrrhizae crude drug, add its weight 8-12 water boiling and extraction doubly 2-3 time, each 1-3 hour, obtain extracting solution, extracting solution is concentrated into the medicinal extract that relative density is 1.10-1.15, obtain Radix Glycyrrhizae and extract component;
2) alcohol precipitation: make the ethanol volumetric concentration reach 50-70% with adding ethanol in the medicinal extract, 0-4 ℃ of refrigeration was left standstill 12-24 hour, filtered, and filter residue discards, and gets filtrate and is concentrated into relative density 1.05-1.10; Add ethanol again and make the ethanol volumetric concentration reach 75-80%, filtration in 12-24 hour is left standstill in 0-4 ℃ of refrigeration, gets the concentrated volatilization of filtrate and removes ethanol, and sample solution is centrifugal through 10000-25000 rev/min supercentrifuge, obtains Radix Glycyrrhizae alcohol precipitation component;
3) cross film: centrifugate is separated through molecular weight cut-off 3000-6000Da hollow-fibre membrane separometer, working pressure 0.05-0.3MPa, trapped fluid discards, and sees through liquid and is the membrane sepn component;
4) the X-5 macroporous adsorbent resin separates: the membrane sepn component is splined on the X-5 macroporous adsorptive resins, applied sample amount and parting material volume ratio are 1: 100-500, adopt water and volumetric concentration 30-50% ethanol to make the moving phase wash-out respectively, the volume of each wash-out is a 3-6 column volume, flow velocity be 1-3 column volume/hour; Recycling elution, elutriant concentrates, and being concentrated into concentration is the 0.15-0.6 grams per milliliter, crosses 0.2-0.4 micron filter membrane, is liquirtin macroporous resin separated portion;
5) industrial chromatography separates: the silica gel bonded stationary phase of C18 with particle diameter 5-40 micron is a chromatograph packing material, with the first alcohol and water is moving phase, gradient elution, the volumetric concentration of methyl alcohol changes from 0-100%, preferably change from 0-70%, collect target components, lyophilize is liquirtin, sample is carried out high-efficient liquid phase analysis determine product purity.
Described chromatogram column efficiency is 5000-20000 column plate/rice, and the chromatogram column length is 200 millimeters-600 millimeters, and the chromatographic column internal diameter is 20 millimeters-300 millimeters; Described resin column length is 40 centimetres-100 centimetres, and the resin column internal diameter is 10 centimetres-20 centimetres, and resin extender is the X-5 type macroporous adsorbent resin of 0.3-1.25 millimeter.
The present invention has the following advantages:
1. sample purity height.Because the present invention adopted state-of-the-art industrial chromatography separation and preparation technology, chromatograph packing material be high score from the ODS of ability (the strong stationary phase that closes of C18) parting material, the high score that utilizes industrial chromatography can guarantee that from ability the purity of product reaches more than 98%.
2. favorable reproducibility.The present invention utilizes industrial chromatography system and the stable performance of ODS, can guarantee that liquirtin separates the circulation ratio and the stability of preparation.
3. the cycle is short.The present invention extracts from the pulverizing of crude drug and prepares the liquirtin product, only needs 7 days time.
4. organic residual low.Because the present invention has abandoned technology such as solvent extraction, silica gel column chromatography in the traditional technology, has adopted the less industrial chromatography method of organic solvent usage quantity, and the finished product employing lyophilize processing, so the organic solvent residual of the finished product is especially little.
5. can realize large-scale commercial production.Institute of the present invention adopting process is very easy to realize stdn that automatization is suitable for carrying out industrialization scale operation.
Description of drawings
Fig. 1 prepares the preparative chromatography figure of liquirtin for the embodiment of the invention 1 industrial chromatography;
Fig. 2 is the high-efficient liquid phase analysis color atlas of the embodiment of the invention 1 liquirtin.
Embodiment
Embodiment 1
The Radix Glycyrrhizae crude drug is pulverized, quantitatively taken by weighing 1 kilogram, place 50 liters of extractors, add 10 premium on currency and decocted 2 hours, filter, the filtrate preservation is standby, adds 10 premium on currency in the filter residue again and decocts 2 hours, filter, and filtrate and merging for the first time, filter residue discards.The extracting solution rotary evaporation is concentrated, and obtaining 240 milliliters is 1.12 medicinal extract to relative density.Add 412 milliliter of 95% ethanol in medicinal extract, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into 160 milliliters, relative density 1.05 adds 854 milliliter of 95% ethanol in concentrated solution, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, concentrated solution is centrifugal through supercentrifuge (20000 rev/mins), obtains 250 milliliters of Radix Glycyrrhizae alcohol precipitation components.
Radix Glycyrrhizae alcohol precipitation component is joined in the charging stock tank of molecular weight cut-off 3000Da hollow-fibre membrane separometer, the adjustment working pressure is 0.1MPa, collects to see through liquid, and trapped fluid discards.Making and seeing through liquid concentration is 30 grams per liters.
Long 80 centimetres of macroporous adsorptive resins, 10 centimetres of column internal diameters, resin extender is the X-5 type macroporous adsorbent resin of 0.3-1.25 millimeter, last sample speed is 1BV/h, water and 40% ethanol elution are collected 40% ethanol elution position respectively, and it is 0.4 grams per milliliter that 40% ethanol elution position rotary evaporation is concentrated into concentration, cross 0.22 micron filter membrane, obtain 30 milliliters of Radix Glycyrrhizae resin isolation components.
The industrial chromatography preparation: the industrial chromatography system is made up of high pressure binary gradient pump, high pressure sampling valve, chromatographic column, UV-detector, chromatographic working station successively.400 millimeters of industrial chromatography post column lengths, 80 millimeters of internal diameters, chromatograph packing material is the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, and setting the ultraviolet detection wavelength is 254nm, set gradient (seeing Table 1), initial flow phase (20% methanol-water) balance chromatographic column 20 minutes, extracting liquorice resin isolation sample 10ml, sample introduction, by setting gradient elution, collect 24 minutes to 27 minutes and 5 seconds components.Wash-out finishes, balance pillar once more, and sample introduction is collected elution fraction.Be total to three (see figure 1)s of sample introduction, collect the elution fraction that obtains with three times, merge, rotary evaporation is concentrated into 10 milliliters, obtain liquirtin product 2.0 grams by lyophilize again, sample is carried out high-efficient liquid phase analysis determine product purity, get 20 milligrams of samples and carry out nmr analysis, structure is identified greater than 98% (see figure 2).Nuclear magnetic data:
1H NMR 400MHz (DMSO-d
6) δ (ppm): 10.599 (1H, s, OH), 7.65 (1H, d, H-5), 7.45 (2H, d, H-2 ', 6 '), 7.06 (2H, d, H-3 ', 5 '), 6.51 (1H, dd, H-6), 6.35 (1H, d, H-8), 5.53 (1H, dd, H-2), 4.89 (1H, d, Glc-H-1), 3.1～3.7 (m, proton and trans H-3 on the sugar), 2.67 (1H, dd, cis H-3).
13CNMR400MHz(DMSO-d
6)δ(ppm)：78.64(C-2)，43.16(C-3)，189.99(C-4)，128.39(C-5)，110.55(C-6)，164.62(C-7)，102.58(C-8)，163.03(C-9)，113.55(C-10)，132.35(C-1′)，127.97(C-2′，C-6′)，116.17(C-3′，C-5′)，157.44(C-4′)，100.30(Glc-C-1)，73.20(Glc-C-2)，77.03(Glc-C-3)，69.71(Glc-C-4)，76.61(Glc-C-5)，60.69(Glc-C-6)。
The structural formula of liquirtin:
Table 1 prepares the eluent gradient table of liquirtin for industrial chromatography.
Embodiment 2
The Radix Glycyrrhizae crude drug is pulverized, quantitatively taken by weighing 0.5 kilogram, place 20 liters of extractors, add 6 premium on currency and decocted 1 hour, filter, the filtrate preservation is standby, adds 5 premium on currency in the filter residue again and decocts 3 hours, filter, and filtrate and merging for the first time, filter residue discards.The extracting solution rotary evaporation is concentrated, and obtaining 140 milliliters is 1.10 medicinal extract to relative density.Add 240 milliliter of 95% ethanol in medicinal extract, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into 40 milliliters, relative density 1.07 adds 428 milliliter of 95% ethanol in concentrated solution, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, concentrated solution is centrifugal through supercentrifuge (20000 rev/mins), obtains 140 milliliters of Radix Glycyrrhizae alcohol precipitation components.
Radix Glycyrrhizae alcohol precipitation component is joined in the charging stock tank of molecular weight cut-off 6000Da hollow-fibre membrane separometer, the adjustment working pressure is 0.1MPa, collects to see through liquid, and trapped fluid discards.Making and seeing through liquid concentration is 25 grams per liters.
Long 40 centimetres of macroporous adsorptive resins, 10 centimetres of column internal diameters, resin extender is the X-5 type macroporous adsorbent resin of 0.3-1.25 millimeter, last sample speed is 0.5BV/h, water and 50% ethanol elution are collected 50% ethanol elution position respectively, and it is 0.2 grams per milliliter that 50% ethanol elution position rotary evaporation is concentrated into concentration, cross 0.22 micron filter membrane, obtain 18 milliliters of Radix Glycyrrhizae resin isolation components.
300 millimeters of industrial chromatography post column lengths, 80 millimeters of internal diameters, chromatograph packing material is the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, and setting the ultraviolet detection wavelength is 254nm, set gradient, balance each other chromatographic column 20 minutes of initial flow, extracting liquorice resin isolation sample 9ml, sample introduction, by setting gradient elution, collect target components.Wash-out finishes, balance pillar once more, and sample introduction is collected elution fraction.Be total to sample introduction twice, the elution fraction with twice collection obtains merges, and rotary evaporation is concentrated into 6 milliliters, obtains liquirtin product 0.6 gram by lyophilize again.
Embodiment 3
The Radix Glycyrrhizae crude drug is pulverized, quantitatively taken by weighing 5 kilograms, place 250 liters of extractors, add 60 premium on currency and decocted 2 hours, filter, the filtrate preservation is standby, adds 60 premium on currency in the filter residue again and decocts 2 hours, filter, and filtrate and merging for the first time, filter residue discards.The extracting solution rotary evaporation is concentrated, and obtaining 1.2, to rise to relative density be 1.13 medicinal extract.Add 2.1 liter of 95% ethanol in medicinal extract, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into 0.7 liter, relative density 1.08 adds 3.8 liter of 95% ethanol in concentrated solution, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, concentrated solution is centrifugal through supercentrifuge (20000 rev/mins), obtains 1.5 liters of Radix Glycyrrhizae alcohol precipitation components.
Radix Glycyrrhizae alcohol precipitation component is joined in the charging stock tank of molecular weight cut-off 6000Da hollow-fibre membrane separometer, the adjustment working pressure is 0.1MPa, collects to see through liquid, and trapped fluid discards.Making and seeing through liquid concentration is 30 grams per liters.
Long 50 centimetres of macroporous adsorptive resins, 20 centimetres of column internal diameters, resin extender is the X-5 type macroporous adsorbent resin of 0.3-1.25 millimeter, last sample speed is 2BV/h, water and 45% ethanol elution are collected 45% ethanol elution position respectively, and it is 0.5 grams per milliliter that 45% ethanol elution position rotary evaporation is concentrated into concentration, cross 0.22 micron filter membrane, obtain 160 milliliters of Radix Glycyrrhizae resin isolation components.
600 millimeters of industrial chromatography post column lengths, 100 millimeters of internal diameters, chromatograph packing material are the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, setting the ultraviolet detection wavelength is 254nm, set gradient, balance each other chromatographic column 20 minutes of initial flow, flow velocity 400 ml/min, extracting liquorice resin isolation sample 30ml, sample introduction by setting gradient elution, is collected 32 minutes 30 seconds to 36 minutes components.Wash-out finishes, balance pillar once more, and sample introduction is collected elution fraction.Be total to 6 (see figure 1)s of sample introduction, the elution fraction with 6 collections obtain merges, and rotary evaporation is concentrated into 100 milliliters, obtains liquirtin product 12.5 grams by lyophilize again.
Embodiment 4
The Radix Glycyrrhizae crude drug is pulverized, quantitatively taken by weighing 10 kilograms, place 250 liters of extractors, add 100 premium on currency and decocted 2 hours, filter, the filtrate preservation is standby, adds 100 premium on currency in the filter residue again and decocts 2 hours, filter, and filtrate and merging for the first time, filter residue discards.The extracting solution rotary evaporation is concentrated, and obtaining 2.2, to rise to relative density be 1.15 medicinal extract.Add 3.8 liter of 95% ethanol in medicinal extract, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into 1.5 liters, relative density 1.09 adds 8 liter of 95% ethanol in concentrated solution, fully stir, 0 ℃ of refrigeration was left standstill 24 hours, filter, filter residue discards, and filtrate is concentrated into does not have the alcohol flavor, concentrated solution is centrifugal through supercentrifuge (20000 rev/mins), obtains 2.7 liters of Radix Glycyrrhizae alcohol precipitation components.
Radix Glycyrrhizae alcohol precipitation component is joined in the charging stock tank of molecular weight cut-off 3000Da hollow-fibre membrane separometer, the adjustment working pressure is 0.1MPa, collects to see through liquid, and trapped fluid discards.Making and seeing through liquid concentration is 85 grams per liters.
Long 100 centimetres of macroporous adsorptive resins, 20 centimetres of column internal diameters, resin extender is the X-5 type macroporous adsorbent resin of 0.3-1.25 millimeter, last sample speed is 0.5BV/h, water and 40% ethanol elution are collected 40% ethanol elution position respectively, and it is 0.6 grams per milliliter that 40% ethanol elution position rotary evaporation is concentrated into concentration, cross 0.22 micron filter membrane, obtain 270 milliliters of Radix Glycyrrhizae resin isolation components.
500 millimeters of industrial chromatography post column lengths, 200 millimeters of internal diameters, chromatograph packing material are the C18 bonded stationary phase of 10-20 micron, and it is 15000 column plate/rice that post is imitated, setting the ultraviolet detection wavelength is 254nm, set gradient, balance each other chromatographic column 20 minutes of initial flow, flow velocity 800 ml/min, extracting liquorice resin isolation sample 60ml, sample introduction by setting gradient elution, is collected 32 minutes 30 seconds to 36 minutes components.Wash-out finishes, balance pillar once more, and sample introduction is collected elution fraction.Be total to 5 (see figure 1)s of sample introduction, the elution fraction with 5 collections obtain merges, and rotary evaporation is concentrated into 200 milliliters, obtains liquirtin product 28 grams by lyophilize again.
Claims (5)
1. the method for separating and preparing of a liquirtin is characterized in that:
1) extract: take by weighing the Radix Glycyrrhizae crude drug, add its weight 8-12 water boiling and extraction doubly 2-3 time, each 1-3 hour, obtain extracting solution, it is 1.10-1.15 that extracting solution is concentrated into relative density, gets medicinal extract;
2) alcohol precipitation: make the ethanol volumetric concentration reach 50-70% with adding ethanol in the medicinal extract, 0-4 ℃ of refrigeration was left standstill 12-24 hour, filtered, and got filtrate and was concentrated into relative density 1.05-1.10; Add ethanol again and make the ethanol volumetric concentration reach 75-80%, filtration in 12-24 hour is left standstill in 0-4 ℃ of refrigeration, gets the concentrated volatilization of filtrate and removes ethanol, and sample solution is centrifugal through 10000-25000 rev/min supercentrifuge;
3) cross film: centrifugate is separated through molecular weight cut-off 3000-6000Da hollow-fibre membrane separometer, working pressure 0.05-0.3MPa, trapped fluid discards, and sees through liquid and is the membrane sepn component;
4) the X-5 macroporous adsorbent resin separates: the membrane sepn component is splined on the X-5 macroporous adsorptive resins, applied sample amount and parting material volume ratio are 1: 100-500, adopt water and volumetric concentration 30-50% ethanol to make the moving phase wash-out respectively, the volume of each wash-out is a 3-6 column volume, flow velocity be 1-3 column volume/hour; Recycling elution, elutriant concentrates, and being concentrated into concentration is the 0.15-0.6 grams per milliliter, crosses 0.2-0.4 micron filter membrane, is liquirtin macroporous resin separated portion;
5) industrial chromatography separates: the silica gel bonded stationary phase of C18 with particle diameter 5-40 micron is a chromatograph packing material, is moving phase with the first alcohol and water, gradient elution, and the volumetric concentration of methyl alcohol changes from 0-100%, collects target components, and lyophilize is liquirtin.
2. according to the method for separating and preparing of the described liquirtin of claim 1, it is characterized in that: described resin column length is 40 centimetres-100 centimetres, and the resin column internal diameter is 10 centimetres-20 centimetres, and resin extender is the X-5 type macroporous adsorbent resin of 0.3-1.25 millimeter.
3. according to the method for separating and preparing of the described liquirtin of claim 1, it is characterized in that: described chromatogram column efficiency is 5000-20000 column plate/rice.
4. according to the method for separating and preparing of the described liquirtin of claim 1, it is characterized in that: described chromatogram column length is 200 millimeters-600 millimeters, and the chromatographic column internal diameter is 20 millimeters-300 millimeters.
5. according to the method for separating and preparing of the described liquirtin of claim 1, it is characterized in that: during described gradient elution, the volumetric concentration of methyl alcohol changes from 0-70%, collects target components.
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| CN102911221A (en) * | 2011-08-01 | 2013-02-06 | 江苏康缘药业股份有限公司 | Method for industrially preparing geniposide from gardenia |
| 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 |
| CN103570779A (en) * | 2012-08-04 | 2014-02-12 | 江苏汉邦科技有限公司 | Method for preparing glycyrrhizin by simulated moving bed separation |
| CN102911218B (en) * | 2012-10-30 | 2015-07-01 | 中国科学院烟台海岸带研究所 | Method for synchronously separating liquiritin and liquiritin apioside 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 |
| CN105753917B (en) * | 2016-04-14 | 2018-06-15 | 青海省青海湖药业有限公司 | A kind of isolation and purification method of liquiritin |
| 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 |
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| CN1477104A (en) * | 2003-07-11 | 2004-02-25 | 上海奥利实业有限公司 | Extraction and purification method of licoflavone |
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