CN101955504A - Method for preparing specnuezhenide, nuezhenoside and oleanolic acid by high-speed countercurrent chromatography - Google Patents
Method for preparing specnuezhenide, nuezhenoside and oleanolic acid by high-speed countercurrent chromatography Download PDFInfo
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- CN101955504A CN101955504A CN2010101827598A CN201010182759A CN101955504A CN 101955504 A CN101955504 A CN 101955504A CN 2010101827598 A CN2010101827598 A CN 2010101827598A CN 201010182759 A CN201010182759 A CN 201010182759A CN 101955504 A CN101955504 A CN 101955504A
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Abstract
The invention relates to a method for separating and preparing high-purity specnuezhenide, nuezhenoside and oleanolic acid from natural plant glossy privet fruit by applying a high-speed countercurrent chromatography, which has the characteristics of no existence of irreversible adsorption and prevention of sample loss and has the advantages of good separating effect, less solvent dosage, no pollution, high efficiency, high speed and great preparation amount separation. The method is suitable for preparing a high-purity monomer by using various natural products containing one or more specnuezhenide, nuezhenoside and oleanolic acid obtained by various approaches and extracts of the natural products as raw materials and is simple and convenient as well as easy to apply.
Description
Technical field:
The invention belongs to the extracted form natural plant preparation field, relate to a kind of method of from the natural phant Glossy Privet Fruit, separating the special Ligustrum lucidum Ait of preparation, the bitter glycosides of glossy privet and Oleanolic Acid with high speed adverse current chromatogram.
Background technology:
Glossy Privet Fruit is Oleaceae (Oleaceae) plant glossy privet Ligustrum lucidum Ait dry mature fruit, is the traditional medicine of strengthening the body resistance to consolidate the constitution of China.Have yin-nourishing gas arranged, flat irascibility, strong waist knee, strengthen the bone, effect such as nourishing liver and kidney, black beard and hair.In recent years chronic tracheitis, hepatitis, hyperlipidemia, diabetes, involution syndrome, Infertility, atherosclerosiss etc. of being used for the treatment of more.Contained chemical ingredients mainly contains organic acid, glycosides, terpene, steroid class, carbohydrate, amino acid and trace element, volatile oil.Oleanolic Acid is its main pentacyclic triterpene composition, and the bitter glycosides of special Ligustrum lucidum Ait and glossy privet is its water-soluble secoiridoid glycosides composition.Structure is as follows:
The bitter glycosides Oleanolic Acid of special Ligustrum lucidum Ait glossy privet
Modern pharmacological research shows, Glossy Privet Fruit have cardiac stimulant, hormone two-ways regulation, reducing blood sugar and blood fat, adjusting body's immunity, anti-inflammatory, antibacterial, anti-ageing, atherosclerosis, can be to the effect of chemotherapy or caused by radiation oligoleukocythemia by leukocyte increasing.Special Ligustrum lucidum Ait has the collaborative ConA that increases suboptimal dose stimulates LT effect, and the restraining effect of antagonism Dex is arranged to a certain extent.Oleanolic Acid have the liver of protecting enzyme, platelet aggregation-against, reducing blood-fat fall, to immunity system and II, III, IV allergic reaction type are had obvious restraining effect.For Glossy Privet Fruit triterpene and secoiridoid glycosides composition are carried out researchs such as more deep pharmacologically active and mechanism of action, need index compositions such as triterpene and secoiridoid that glossy privet class medicinal material and relevant Chinese medicine preparation are carried out quality control simultaneously, need a large amount of monomeric compounds.Therefore, provide a kind of special Ligustrum lucidum Ait of separation and purification, the bitter glycosides of glossy privet and Oleanolic Acid method from glossy privet fast and efficiently, have the modern Chinese herbal medicine preparation of special efficacy and make full use of China's herb resource etc. significant exploitation.
Adopt the effective monomer in traditional separation method separating plant such as common chromatogram column technique, recrystallization, not only waste time and energy, contaminate environment, and used stationary phase has the non-reversibility adsorption to sample, and this just needs a kind of new separation technology to solve the problems referred to above.High speed adverse current chromatogram (HSCCC) be a kind of successive that development in recent years is got up need not the solid support thing efficiently, liquid liquid distribution chromatography isolation technique fast, have characteristics such as fractional dose is big, sample free of losses, rate of recovery height, isolating environment mitigation, saving solvent, be widely used in the preparation separation and the purifying of field chemical substances such as biology, medicine, environmental protection.
Summary of the invention:
The purpose of this invention is to provide the method that high speed adverse current chromatogram prepares special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, to overcome the above-mentioned problems in the prior art.
The present invention is achieved through the following technical solutions:
High speed adverse current chromatogram prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, and it may further comprise the steps:
Be made up of the preparation of crude extract and separation and purification two portions of crude extract, it is characterized in that high speed adverse current chromatogram is used in the separation and purification of crude extract, its basic technology route is:
(1) with the Glossy Privet Fruit pulverizing medicinal materials, the boiling water heating in water bath extracts, the extracting solution filtered while hot, and cooling obtains water and gets thing and residue;
(2) enrichment of special Ligustrum lucidum Ait, the bitter glycosides of glossy privet: aqueous extract is added absorption with macroporous adsorbent resin, and the 10-50% ethanol gradient elution is collected elutriant, and decompression recycling ethanol obtains special Ligustrum lucidum Ait, the bitter glycosides mixing of glossy privet crude extract;
(3) extraction of Oleanolic Acid: water is carried residue added in the ethanol that boils refluxing extraction 1-1.5 hour, extracts 1-3 time, filter extracting solution, add the gac reflux decolour again, filtration, concentrated destainer gets the Oleanolic Acid fluid extract;
(4) purifying of special Ligustrum lucidum Ait, the bitter glycosides of glossy privet: the pure product that crude extract made special Ligustrum lucidum Ait of high purity and the bitter glycosides of glossy privet with the high speed adverse current chromatogram partition method.
(5) purifying of Oleanolic Acid: above-mentioned Oleanolic Acid fluid extract is made the pure product of high purity oleanolic acid with the high speed adverse current chromatogram partition method.
Water extract material ratio described in the step (1) is 1: 8-10 (kg/L), extraction time is 1.5-2 hour.
Optional nonpolar, low-pole of macroporous adsorbent resin described in the step (2) or Semi-polarity macroporous adsorbent resin are as macroporous adsorbent resins such as D101, AB-8, DM301, HPD100.
Elution requirement described in the step (2) is earlier with 3-4 times of column volume 10%-30% ethanol elution, again with 4-5 times of column volume 35%-50% ethanol elution.
The alcohol concn that boils described in the step (3) is 70%-95%, and consumption is 10-20 a times of residue quality; Described activated carbon dosage is 0.5%-1%, decolours 0.5-1 hour.
High-speed countercurrent chromatography carries out purifying to crude extract described in the step (4) (5), preparation earlier constitutes the solvent system of stationary phase, moving phase, make in the counter current chromatograph pillar and be full of stationary phase, pillar is rotated, moving phase being pumped in the post again, enter the crude extract for preparing by sampling valve, is stationary phase mutually more than the two phase solvent system, be moving phase mutually down, according to detecting spectrogram receiving target composition.
High-speed countercurrent chromatography described in the step (4) carries out purifying to special Ligustrum lucidum Ait, the bitter glycosides of glossy privet, solvent system is made of four components, the A component can be selected from halohydrocarbon such as chloroform, methylene dichloride, B, C component can be selected from Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketones such as methyl alcohol, ethanol, propyl alcohol, acetone, propyl carbinol, isopropylcarbinol, the D component is a water, preferred chloroform-methanol-n-butanol-water system, the volume ratio of A, B, C, D is 1-5: 2-10: 0.5-5: 2-10.
High-speed countercurrent chromatography described in the step (4) carries out purifying to special Ligustrum lucidum Ait, the bitter glycosides of glossy privet, solvent system is made of three components, the A component can be selected from fatty ester classes such as ethyl acetate, propyl acetate, n-butyl acetate, the B component can be selected from Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketones such as methyl alcohol, ethanol, propyl alcohol, acetone, propyl carbinol, isopropylcarbinol, the C component is a water, ethyl acetate-n-butanol-water system, the volume ratio of A, B, C are 1-4: 1-2: 2-5.
The described high-speed countercurrent chromatography of step (5) carries out purifying to Oleanolic Acid, solvent system is made of four components, the A component can be selected from ether, chloroform, acetone, normal hexane or heptane, the B component can be selected from fatty ester classes such as ethyl acetate, propyl acetate, isopropyl acetate, the C component can be selected from ethanol or methyl alcohol, the D component is a water, preferred chloroform-ethyl acetate-methanol-water system, and A, B, C, D volume ratio are 1-10: 1-20: 1-10: 1-10.
Described engine speed is 500-1000r/min, and the flow velocity of described moving phase is 1.0-5ml/min.
In sum, there is following advantage in the present invention:
(1) this separation process can be carried out continuously, and is easy and simple to handle, the efficient height;
Characteristics such as (2) there is not irreversible adsorption in the preparation of employing high-speed countercurrent chromatography, has avoided the loss of sample, has good separating effect, and solvent load is few, and is pollution-free, efficient, quick.
Embodiment:
The present invention is described further below in conjunction with embodiment.
Embodiment 1:
1. get 500g Glossy Privet Fruit pulverizing medicinal materials and become meal to drop in the extractor, add 8 times of amount boiling water heating in water bath and extract 2h, extract 3 times, filtered while hot, cooling obtains aqueous extract and residue.
2. with the saturated absorption of AB-8 macroporous resin column 1h on the aqueous extract,, use 4 times of column volume 50% ethanol elutions again, collect elutriant earlier with 4 times of column volume 20% ethanol elutions, decompression recycling ethanol, drying obtains special Ligustrum lucidum Ait and the bitter glycosides mixing of glossy privet crude extract; Water is carried residue add 95% of 15 times of amounts alcohol reflux 1h that boils, extracts 2 times, filtered while hot gets extracting solution, adds the 2.5g gac reflux 0.5h that decolours, filtered while hot, and concentrating under reduced pressure gets the Oleanolic Acid fluid extract.
3. use high speed adverse current chromatogram separation and purification crude extract.
A. adopt chloroform: methyl alcohol: propyl carbinol: water (2: 8: 1: solvent systems 7), rotating speed were 750r/min, on be stationary phase mutually, is moving phase mutually down, flow velocity 5ml/min.
The concrete operations step is: place separating funnel by above-mentioned volume ratio preparation solvent systems, after shaking up, standing demix, isoequilibrium separated mutually with upper and lower after for some time.Then, use earlier, be full of whole pillar, adjust main frame and just change, the head end of following phase moving phase from pillar pumped in the post as stationary phase; After treating that whole system is set up running balance, by the sampling valve sample introduction; Collect target component according to the spectrogram of detector then.
B. A is separated the certain applications high-speed counter-current chromatograph separation and purification once more that obtains.
Adopt ethyl acetate: propyl carbinol: the solvent systems of water (2: 1: 3), rotating speed are 750r/min, on be stationary phase mutually, be moving phase mutually down, flow velocity 5ml/min, the same A of concrete operations promptly gets special Ligustrum lucidum Ait and the bitter glycosides of glossy privet with recrystallizing methanol respectively with target component.
C. adopt chloroform: ethyl acetate: methyl alcohol: water (3: 15: 5: solvent systems 5), rotating speed were 750r/min, on be stationary phase mutually, be moving phase mutually down, flow velocity 5ml/min, the same A of concrete operations promptly obtains Oleanolic Acid with target component with the dehydrated alcohol recrystallization.
The purity that obtains special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid by above-mentioned condition detects with HPLC, and the result 〉=96%.
HPLC analysis condition: chromatographic column C18, moving phase is MeOH: H
2O (40: 60); Detect wavelength 224nm.
Embodiment 2:
1. get 200g Glossy Privet Fruit pulverizing medicinal materials and become meal to drop in the extractor, add 10 times of amount boiling water heating in water bath and extract 1.5h, extract 2 times, filtered while hot, cooling obtains aqueous extract and residue.
2. with the saturated absorption of AB-8 macroporous resin column 1.5h on the aqueous extract,, use 4 times of column volume 45% ethanol elutions again, collect elutriant earlier with 3 times of column volume 10% ethanol elutions, decompression recycling ethanol, drying obtains special Ligustrum lucidum Ait and the bitter glycosides mixing of glossy privet crude extract; Water is carried residue add 85% of 13 times of amounts alcohol reflux 1.5h that boils, extracts 3 times, filtered while hot gets extracting solution, adds the 2.5g gac reflux 1h that decolours, filtered while hot, and concentrating under reduced pressure gets the Oleanolic Acid fluid extract.
3. use high speed adverse current chromatogram separation and purification crude extract.
A. adopt chloroform: methyl alcohol: propyl carbinol: water (4: 8: 2: solvent systems 7), last as stationary phase, be moving phase mutually down, rotating speed is 560r/min, flow velocity 2.5ml/min.The concrete operations step is substantially with " embodiment 1 ".
B. A is separated the certain applications high-speed counter-current chromatograph separation and purification once more that obtains.
Adopt ethyl acetate: propyl carbinol: the solvent systems of water (3: 2: 4), rotating speed are 560r/min, on be stationary phase mutually, is moving phase mutually down, flow velocity 2.5ml/min, the concrete operations step is same " embodiment 1 " substantially.
Adopt chloroform: ethyl acetate: methyl alcohol: water (2: 17: 3: solvent systems 6), last as stationary phase, be moving phase mutually down, rotating speed is 560r/min, flow velocity 2.5ml/min.The concrete operations step is substantially with " embodiment 1 ".
Products obtained therefrom shows that through liquid-phase chromatographic analysis purity all 〉=97%.
Embodiment 3:
1. get 1000g Glossy Privet Fruit pulverizing medicinal materials and become meal to drop in the extractor, add 9 times of amount boiling water heating in water bath and extract 2h, extract 2 times, filtered while hot, cooling obtains aqueous extract and residue.
2. with the saturated absorption of DM301 macroporous resin column 2h on the aqueous extract,, use 5 times of column volume 40% ethanol elutions again, collect elutriant earlier with 4 times of column volume 10% ethanol elutions, decompression recycling ethanol, drying obtains special Ligustrum lucidum Ait and the bitter glycosides mixing of glossy privet crude extract; Water is carried residue add 80% of 16 times of amounts alcohol reflux 3h that boils, extracts 2 times, filtered while hot gets extracting solution, adds the 9g gac reflux 0.5h that decolours, filtered while hot, and concentrating under reduced pressure gets the Oleanolic Acid fluid extract.
3. use high speed adverse current chromatogram separation and purification crude extract.
A. adopt chloroform: methyl alcohol: propyl carbinol: water (5: 3: 0.5: solvent systems 8), last as stationary phase, be moving phase mutually down, rotating speed is 100r/min, flow velocity 2.5ml/min.The concrete operations step is substantially with " embodiment 1 ".
B. A is separated the certain applications high-speed counter-current chromatograph separation and purification once more that obtains.
Adopt ethyl acetate: propyl carbinol: the solvent systems of water (4: 1.5: 5), rotating speed are 560r/min, on be stationary phase mutually, is moving phase mutually down, flow velocity 4ml/min, the concrete operations step is same " embodiment 1 " substantially.
Adopt chloroform: ethyl acetate: methyl alcohol: water (2: 17: 3: solvent systems 6), last as stationary phase, be moving phase mutually down, rotating speed is 1000r/min, flow velocity 4ml/min.The concrete operations step is substantially with " embodiment 1 ".
Products obtained therefrom shows that through liquid-phase chromatographic analysis purity all 〉=96.5%.
Claims (10)
1. high speed adverse current chromatogram prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, is made up of the preparation of crude extract and separation and purification two portions of crude extract, it is characterized in that high speed adverse current chromatogram is used in the separation and purification of crude extract, and its basic technology route is:
(1) with the Glossy Privet Fruit pulverizing medicinal materials, the boiling water heating in water bath extracts, the extracting solution filtered while hot, and cooling obtains aqueous extract and residue;
(2) enrichment of special Ligustrum lucidum Ait, the bitter glycosides of glossy privet: aqueous extract is added absorption with macroporous adsorbent resin, and the 10-50% ethanol gradient elution is collected elutriant, and decompression recycling ethanol obtains special Ligustrum lucidum Ait, the bitter glycosides mixing of glossy privet crude extract;
(3) extraction of Oleanolic Acid: water is carried residue added in the ethanol that boils refluxing extraction 1-1.5 hour, extracts 1-3 time, filter extracting solution, add the gac reflux decolour again, filtration, concentrated destainer gets the Oleanolic Acid fluid extract;
(4) purifying of special Ligustrum lucidum Ait, the bitter glycosides of glossy privet: the pure product that crude extract made special Ligustrum lucidum Ait of high purity and the bitter glycosides of glossy privet with the high speed adverse current chromatogram partition method.
(5) purifying of Oleanolic Acid: above-mentioned Oleanolic Acid fluid extract is made the pure product of high purity oleanolic acid with the high speed adverse current chromatogram partition method.
2. high speed adverse current chromatogram according to claim 1 prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, and it is characterized in that: the water extract material ratio described in the step (1) is 1: 8-10 (kg/L), extraction time is 1.5-2 hour.
3. high speed adverse current chromatogram according to claim 1 prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, it is characterized in that: optional nonpolar, low-pole of macroporous adsorbent resin described in the step (2) or Semi-polarity macroporous adsorbent resin, as macroporous adsorbent resins such as D101, AB-8, DM301, HPD100.
4. high speed adverse current chromatogram according to claim 1 prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, it is characterized in that: elution requirement described in the step (2) is earlier with 3-4 times of column volume 10%-30% ethanol elution, again with 4-5 times of column volume 35%-50% ethanol elution.
5. high speed adverse current chromatogram according to claim 1 prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, and it is characterized in that: the alcohol concn that boils described in the step (3) is 70%-95%, and consumption is 10-20 a times of residue quality; Described activated carbon dosage is 0.5%-1%, decolours 0.5-1 hour.
6. high speed adverse current chromatogram according to claim 1 prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, it is characterized in that: high-speed countercurrent chromatography carries out purifying to crude extract described in the step (4) (5), preparation earlier constitutes the solvent system of stationary phase, moving phase, make in the counter current chromatograph pillar and be full of stationary phase, pillar is rotated, again moving phase is pumped in the post, enter the crude extract for preparing by sampling valve, be stationary phase mutually more than the two phase solvent system, be moving phase mutually down, according to detecting spectrogram receiving target composition.
7. high speed adverse current chromatogram according to claim 1 prepares special Ligustrum lucidum Ait, the method of bitter glycosides of glossy privet and Oleanolic Acid, it is characterized in that: high-speed countercurrent chromatography is to special Ligustrum lucidum Ait described in the step (4), the bitter glycosides of glossy privet carries out purifying, solvent system is made of four components, the A component can be selected from chloroform, halohydrocarbon such as methylene dichloride, B, the C component can be selected from methyl alcohol, ethanol, propyl alcohol, acetone, propyl carbinol, Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketones such as isopropylcarbinol, the D component is a water, preferred chloroform-methanol-n-butanol-water system, A, B, C, the volume ratio of D is 1-5: 2-10: 0.5-5: 2-10.
8. high speed adverse current chromatogram according to claim 1 prepares special Ligustrum lucidum Ait, the method of bitter glycosides of glossy privet and Oleanolic Acid, it is characterized in that: high-speed countercurrent chromatography is to special Ligustrum lucidum Ait described in the step (4), the bitter glycosides of glossy privet carries out purifying, solvent system is made of three components, the A component can be selected from ethyl acetate, propyl acetate, fatty ester classes such as n-butyl acetate, the B component can be selected from methyl alcohol, ethanol, propyl alcohol, acetone, propyl carbinol, Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketones such as isopropylcarbinol, the C component is a water, ethyl acetate-n-butanol-water system, A, B, the volume ratio of C is 1-4: 1-2: 2-5.
9. high speed adverse current chromatogram according to claim 1 prepares special Ligustrum lucidum Ait, the method of bitter glycosides of glossy privet and Oleanolic Acid, it is characterized in that: the described high-speed countercurrent chromatography of step (5) carries out purifying to Oleanolic Acid, solvent system is made of four components, the A component can be selected from ether, chloroform, acetone, normal hexane or heptane, the B component can be selected from ethyl acetate, propyl acetate, fatty ester classes such as isopropyl acetate, the C component can be selected from ethanol or methyl alcohol, the D component is a water, preferred chloroform-ethyl acetate-methanol-water system, A, B, C, the D volume ratio is 1-10: 1-20: 1-10: 1-10.
10. high speed adverse current chromatogram according to claim 1 prepares the method for special Ligustrum lucidum Ait, the bitter glycosides of glossy privet and Oleanolic Acid, and it is characterized in that: described engine speed is 500-1000r/min, and the flow velocity of described moving phase is 1.0-5ml/min.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102321127A (en) * | 2011-07-05 | 2012-01-18 | 石任兵 | Novel method for preparing salidroside from glossy privet fruit |
| CN102911243A (en) * | 2011-08-02 | 2013-02-06 | 苏州宝泽堂医药科技有限公司 | Preparation method of high-purity reinioside C |
| CN102911242A (en) * | 2011-08-02 | 2013-02-06 | 苏州宝泽堂医药科技有限公司 | Preparation method of akebia quinata acid |
| CN108329367A (en) * | 2018-04-23 | 2018-07-27 | 福建中医药大学 | A method of preparing Specnuezhenide from the fruit of glossy privet |
| CN114315922A (en) * | 2022-01-05 | 2022-04-12 | 湖北民族大学 | Method for separating ligustrin, oleuropein and 10-hydroxyligustrin reference substance from white leaf wax by HSCCC |
-
2010
- 2010-05-26 CN CN2010101827598A patent/CN101955504A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102321127A (en) * | 2011-07-05 | 2012-01-18 | 石任兵 | Novel method for preparing salidroside from glossy privet fruit |
| CN102911243A (en) * | 2011-08-02 | 2013-02-06 | 苏州宝泽堂医药科技有限公司 | Preparation method of high-purity reinioside C |
| CN102911242A (en) * | 2011-08-02 | 2013-02-06 | 苏州宝泽堂医药科技有限公司 | Preparation method of akebia quinata acid |
| CN108329367A (en) * | 2018-04-23 | 2018-07-27 | 福建中医药大学 | A method of preparing Specnuezhenide from the fruit of glossy privet |
| CN114315922A (en) * | 2022-01-05 | 2022-04-12 | 湖北民族大学 | Method for separating ligustrin, oleuropein and 10-hydroxyligustrin reference substance from white leaf wax by HSCCC |
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Application publication date: 20110126 |