CN105693714A - Method for separating alkaloidal compounds from Chinese mahonia stems with pH-zone-refining countercurrent chromatography - Google Patents
Method for separating alkaloidal compounds from Chinese mahonia stems with pH-zone-refining countercurrent chromatography Download PDFInfo
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- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
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Abstract
The invention discloses a method for separating alkaloidal compounds from Chinese mahonia stems with pH-zone-refining countercurrent chromatography. The conditions adopted for the separation are as follows: a solvent system is prepared from chloroform, methanol and water with the ratio of chloroform to methanol to water being (3.5-4.5):(2.5-3.5):(2.5-3.5), the pH-zone-refining countercurrent chromatograph column volume is 200-400, the loading quantity of samples is 2-5 g, the rotating speed is 300-1,000 rpm, an upper phase is a stationary phase, a lower phase is a moving phase, the flow velocity is 1.5-2.5 mL/min, the stationary phase retention rate is 35.71%, and the detection wavelength is 250-260 nm. The preparation cost of the method is lower than that of a method in the prior art, the operation is simple and convenient, and the efficiency is high; with the adoption of the preparation method, a larger quantity of monomeric compounds including jateorhizine, berberine, palmatine and columbamine with the purity of 96% or higher can be separated and prepared from the Chinese mahonia stems as traditional Chinese medicine, and columbamine is separated from the Chinese mahonia stems as the traditional Chinese medicine for the first time.
Description
Technical field
The present invention relates to the isolation and purification method of a kind of Effective Component of Chinese Medicine, be specially application pH-zone refining countercurrent and separate the method for alkaloid compound (jateorhizine, berberine, Columbamine, palmatine monomer) in Caulis Mahoniae。
Background technology
Caulis Mahoniae is the dry stem of Berberidaceae plant Mahonia bealei (Fort.) Carr. Mahoniabealei (Fort.) Carr or mahonia fortuneiFedde Mahoniafortunei (Lindl.) Fedde, its nature and flavor are bitter, cold, there is effect of heat clearing and damp drying, eliminating fire and detoxication。Cure mainly damp-heat dysentery, jaundice dark coloured urine, conjunctival congestion and swelling pain, toothache due to stomach-fire, furuncle carbuncle。In Caulis Mahoniae, alkaloid compound is mainly isoquinoline alkaloid, and including jateorhizine, palmatine and berberine, result of study shows that isoquinoline alkaloid can suppress free radical and lipoxygenase activity thus reaching the effect of antiinflammatory。Additionally, alkaloidal oxidation resistance is also relevant with its disease resistance, resistance and slow down aging。Modern pharmacological research shows, Caulis Mahoniae also has the effect of certain reversing tumor cells resistance。
The existing literature method prepared about alkaloids monomeric compound separation in Caulis Mahoniae mainly adopts repeatedly silica gel column chromatography and SephadexLH-20 gel column chromatography, its limitation be waste time and energy, contaminated environment, sample purity low, and sample is had irreversibility adsorption by column chromatography repeatedly, it is low, relatively costly that separation obtains alkaloid monomer preparation efficiency, it is difficult to develops into the isolation technics that preparation amount is big。
High speed adverse current chromatogram (High-speedCounter-currentChromatography, HSCCC) being a kind of continuous print of growing up for nearly 30 years liquid liquid partition chromatography isolation technics efficient, quick without any solid support, the sample that it avoids solid state adhesion body or carrier brings is easily by various problems such as dead absorption, loss and degeneration。PH-zone refining countercurrent (pH-Zone-RefiningCountercurrentChromatography) is then on the basis of common high-speed counter-current chromatograph device, allotment by the composition to the solvent system separated used by sample, adopt the hands section of chemistry, the chromatographic separation process making sample component adds the feature assembled by pH zone, simultaneously, the elution process making component shows as the elution process of similar displacement (replacement) chromatograph (DisplacementChromatography), therefore, its chromatogram is no longer the chromatographic peak profile series of Gauss distribution, and become the rectangle zone series precipitous by the border of the big minispread of pH value, its result is the separation preparation amount of the adverse current chromatogram instrument of same volume to be improved several times or even ten times。
Although prior art utilizes alkaloidal report in pH-zone refining countercurrent separation Chinese medicine, known in this field, during pH-zone refining countercurrent separates, used solvent system is one of key factor affecting separating resulting, the solvent commonly used has methanol, petroleum ether, ethyl acetate, normal hexane, acetone, chloroform, acetonitrile etc., the solvent used in each solvent system is at least two kinds, the composition that different Chinese medicine ingredients have, and alkaloidal kind and quantity different, Chinese medicine is different through the composition extracting the alkaloid gross sample obtained, so how to select the solvent species of solvent system for different Chinese medicine, usage ratio between each solvent and coordinate what kind of flow velocity this solvent system selects, applied sample amount, rotating speed etc. just can obtain the higher alkaloid monomer of purity without reference to being worth。
Columbamine has the effect in excited uterus, and the source being currently known is that Berberidaceae plant Japan Radix Berberidis Amurensis BerberisthunbergiiDC rhizome, ranunculaceae plant Rhizoma Coptidis CoptischinensisFranch rhizome, menispermaceous plants Caulis Fibraureae FibraureatinetoriaLour root, Africa palm leaf Radix Stephaniae Tetrandrae Jatrorrhizapalmata (DC.) Miers (J.columba.Miers), bloodroot Bock Nimu BocconiafrutescesLinn leaf, annonaceae plant are according to south wood EnantiachloranthaOliver root。At present, but without the relevant report isolating Columbamine from Caulis Mahoniae, separate alkaloidal record in Caulis Mahoniae also without utilizing pH-zone refining countercurrent。
Summary of the invention
The purpose of the present invention is contemplated to solve the problems referred to above, it is provided that a kind of pH-zone refining countercurrent separates the method for alkaloid compound in Caulis Mahoniae。
To achieve these goals, the present invention adopts the following technical scheme that
A kind of separate the method for alkaloid compound in Caulis Mahoniae, application pH-zone refining countercurrent separates, condition used in described separation is: solvent system is chloroform: methanol: water=3.5-4.5:2.5-3.5:2.5-3.5 (preferred 4:3:3), pH-zone refining countercurrent instrument column volume is 200-400 (preferred 300mL), applied sample amount 2-5g (preferred 3g), rotating speed 300-1000rpm (preferred 800rpm), upper phase is fixing phase, lower phase is mobile phase, flow velocity 1.5-2.5mL/min (preferred 2.0mL/min), fixing phase retention rate 35.71%, detection wavelength 250-260nm (preferred 254nm)。
Described: the extracting method of alkaloid compound in Caulis Mahoniae: (1) adopts ethanol that Caulis Mahoniae medical material is extracted, and is concentrated into extracting solution vacuum without alcohol taste, obtains total extract；(2) total extract is adjusted to acidity, after petroleum ether extraction defat, adjusts to alkalescence, stirring precipitation, be Caulis Mahoniae alkaloid crude extract。
What application pH-zone refining countercurrent separated specifically comprises the following steps that
(1) by solvent system, be placed in separatory funnel, shake up rear stratification, after ready to balance a period of time will biphase up and down separately upper phase is fixing phase, and lower phase is mobile phase, is above added to 60mM hydrochloric acid, under be added to 7.5mM triethylamine；
(2) taking Caulis Mahoniae alkaloid crude extract and be dissolved in the mixed liquor of the upper and lower phase that volume ratio is 1:1 stand-by, described Caulis Mahoniae alkaloid crude extract is 3:10 (g/mL) with mixed liquor with magnitude relation；
(3) first make semi-preparative high-speed counter-current chromatograph injection valve be in sample introduction state, pump fixing will be used mutually with 20mL min-1Flow velocity fills chromatography column, termination of pumping, opening speed controller, the chromatographic chromatography column of high velocity stream is made to rotate forward, when reaching setting speed, the sample syringe dissolved is injected in the liquid storage tube of counter-current chromatograph injection valve, rotate injection valve for connecing column state, making sample enter chromatography column, arranging flow rate of mobile phase is 1.5-2.5mL/min (preferred 2.0mL/min), starts pump mobile phase, then target component is received according to detector ultraviolet spectrogram (Fig. 3),, rotated evaporation, lyophilization obtains pressed powder。
Beneficial effects of the present invention:
The method preparation cost of the present invention is lower than prior art, easy and simple to handle, efficiency is high, can relatively in high volume from Chinese medicine Caulis Mahoniae, separating the method for separating and preparing preparing the purity jateorhizine more than 96%, berberine, palmatine, Columbamine monomeric compound, the present invention isolates Columbamine first from Chinese medicine Caulis Mahoniae。
Accompanying drawing explanation
Fig. 1 is the process chart of the present invention；
Fig. 2 is the pH-zone refining countercurrent figure that Caulis Mahoniae alkaloid gross sample separates；
Fig. 3 is the high-efficient liquid phase chromatogram of alkaloid gross sample；
Fig. 4 is the high-efficient liquid phase chromatogram of jateorhizine monomer；
Fig. 5 is the high-efficient liquid phase chromatogram of berberine monomer；
Fig. 6 is the high-efficient liquid phase chromatogram of palmatine monomer；
Fig. 7 is the high-efficient liquid phase chromatogram of Columbamine monomer；
Fig. 8 is the pH-zone refining countercurrent that comparative example 1 Caulis Mahoniae alkaloid gross sample separates；
Fig. 9 is the pH-zone refining countercurrent that comparative example 2 Caulis Mahoniae alkaloid gross sample separates。
Detailed description of the invention
Below in conjunction with accompanying drawing, the invention will be further described with embodiment。
Embodiment 1:
In Fig. 1 Caulis Mahoniae shown in monomer preparation flow figure。
Taking after Caulis Mahoniae medical material 2kg pulverizes with 95% alcohol reflux 3 times (each 2h), filter, filtrate reduced in volume is to without alcohol taste。
By the extracting solution after above-mentioned concentration, salt adding acid for adjusting pH=3, petroleum ether extraction removes liposoluble constituent 3～5 times, and the water layer after extraction adds ammonia and regulates pH=9, filters to obtain precipitation 10.6g, is required alkaloid gross sample。
Application pH-zone refining countercurrent separation purification Caulis Mahoniae alkaloid gross sample
Solvent system is chloroform: chloroform: methanol: water=4:3:3, and high-speed counter-current chromatograph column volume is 300mL, applied sample amount 3g, rotating speed 800rpm, and upper phase is fixing phase, and lower phase is mobile phase, flow velocity 2.0mL/min, and fixing phase retention rate 35.71% detects wavelength 254nm。
Concrete operating procedure is: prepare solvent system by above-mentioned solvent ratios, it is placed in separatory funnel, shake up rear stratification, to biphase up and down separate after ready to balance a period of time, on be added to 60mM hydrochloric acid, under be added to 7.5mM triethylamine, mutually as fixing phase in acid adding, add under alkali as mobile phase。Take in the mixture that 3g Caulis Mahoniae alkaloid crude extract is dissolved in 5mL acid adding mutually and 5mL is not added with under alkali phase stand-by。Adopt the semi-preparative high-speed counter-current chromatograph that Shanghai is developed with field company, it is by plunger displacement pump, injection valve, Ultraviolet Detector, monitor and the chromatography column (spiral tube formed by polyfluortetraethylene pipe multi-lay winding, capacity is 300mL) etc. composition, first make injection valve be in sample introduction state, pump fixing will be used mutually with flow velocity 20mL min-1Fill chromatography column, termination of pumping。Opening speed controller, makes the chromatographic chromatography column of high velocity stream rotate forward, and during turn up 800rpm, is injected by the sample syringe dissolved in the liquid storage tube of counter-current chromatograph injection valve, rotates injection valve for connecing column state, make sample enter chromatography column。Arranging flow rate of mobile phase is 2.0mL/min, starts pump mobile phase, then receives target component according to detector ultraviolet spectrogram (Fig. 3)。Obtaining berberine (157.2mg), jateorhizine (160.6mg), palmatine (169.8mg), Columbamine (28.1mg) and non-principal component (53.7mg), HPLC purity assay is more than 96%。
Utilize efficient liquid phase chromatographic analysis separator, such as Fig. 3-Fig. 7, liquid-phase condition: Kromasil100-5C18Post (4.6 × 250mmmm), ultraviolet detection wavelength 265nm, column temperature: 25 DEG C, flow velocity: 1.0mL/min, sample size: 10 μ L, mobile phase adopts acetonitrile: saline solution (1% triethylamine solution, adjust pH=3 with phosphoric acid)=25:75。
Structural Identification: the alkaloid application Agilent5973N mass spectrograph and the Varian600MHz nuclear magnetic resonance chemical analysers that obtain separation carry out MS respectively,1The mensuration of HNMR spectrum, the data obtained is as follows:
Jateorhizine: UV (λmax,MeOH):264,345nm.PositiveESI-MSm/z338[M+H]+.1HNMR(DMSO-d6,600MHz)δppm: 9.86 (1H, s, H-8), 8.98 (1H, s, H-13), 8.19 (1H, d, J=9.0Hz, H-11), 8.01 (1H, d, J=9.0Hz, H-12), 7.69 (1H, s, H-1), 6.86 (1H, s, H-4), 4.91 (2H, t, J=6.0Hz, H-6), 4.09 (3H, s, 10-OCH3),4.07(3H,s,9-OCH3),3.94(3H,s,2-OCH3), 3.14 (2H, t, J=6.0Hz, H-5).
Berberine: UV (λmax,MeOH):263and346nm.PositiveESI-MSm/z336[M+H]+.1HNMR(DMSO-d6,600MHz)δppm: 9.90 (1H, s, H-8), 8.96 (1H, s, H-13), 8.21 (1H, d, J=9.0Hz, H-11), 8.01 (1H, d, J=9.0Hz, H-12), 7.80 (1H, s, H-1), 7.09 (1H, s, H-4), 6.18 (2H, s, 2,3-OCH2O), 4.94 (2H, t, J=6.0Hz, H-6), 4.10 (3H, s, 10-OCH3),4.07(3H,s,9-OCH3), 3.21 (2H, t, J=6.0Hz, H-5).
Columbamine: UV (λmax,MeOH):263,345nm.PositiveESI-MSm/z338[M+H]+.1HNMR(DMSO-d6,600MHz)δppm: 9.88 (1H, s, H-8), 8.82 (1H, s, H-13), 8.20 (1H, d, J=9.0Hz, H-11), 8.06 (1H, d, J=9.0Hz, H-12), 7.57 (1H, s, H-1), 7.06 (1H, s, H-4), 4.93 (2H, t, J=6.0Hz, H-6), 4.09 (3H, s, 10-OCH3),4.07(3H,s,9-OCH3),3.90(3H,s,3-OCH3), 3.19 (2H, t, J=6.0Hz, H-5).
Palmatine: UV (λmax,MeOH):272,345nm.PositiveESI-MSm/z352[M+H]+.1HNMR(DMSO-d6,600MHz)δppm: 9.90 (1H, s, H-8), 9.08 (1H, s, H-13), 8.20 (1H, d, J=9.0Hz, H-11), 8.04 (1H, d, J=9.0Hz, H-12), 7.73 (1H, s, H-1), 7.10 (1H, s, H-4), 4.96 (2H, t, J=6.0Hz, H-6), 4.10 (3H, s, 10-OCH3),4.08(3H,s,9-OCH3),3.94(3H,s,2-OCH3),3.88(3H,s,3-OCH3), 3.23 (2H, t, J=6.0Hz, H-5).
Comparative example 1
Condition: chloroform: methanol: water=4:3:3, upper addition 10mMHCl, lower addition 20mM triethylamine, flow velocity: 2.0mL/min, temperature: 25 DEG C, sample size 3g, retention rate: 25%, other condition and operation are with embodiment 1。As shown in Figure 8: separating resulting: only separate berberine and Columbamine。Other operation honor embodiment 1。
Comparative example 2
Condition: normal hexane: ethyl acetate: methanol: water=5:5:3:7, upper addition 10mMHCl, lower addition 20mM triethylamine, flow velocity: 2.0mL/min, temperature: 25 DEG C, sample size 3g, retention rate: 58%, other condition and operation are with embodiment 1。As shown in Figure 9: separating resulting: do not isolate single compound。
The specific embodiment of the present invention is described in conjunction with accompanying drawing although above-mentioned; but not limiting the scope of the invention; one of ordinary skill in the art should be understood that; on the basis of technical scheme, those skilled in the art need not pay various amendments or deformation that creative work can make still within protection scope of the present invention。
Claims (10)
1. one kind separates the method for alkaloid compound in Caulis Mahoniae, application pH-zone refining countercurrent separates, condition used in described separation is: solvent system is chloroform: methanol: water=3.5-4.5:2.5-3.5:2.5-3.5, pH-zone refining countercurrent instrument column volume is 200-400, applied sample amount 2-5g, rotating speed 300-1000rpm, upper phase is fixing phase, and lower phase is mobile phase, flow velocity 1.5-2.5mL/min, fixing phase retention rate 35.71%, detects wavelength 250-260nm。
2. the method for claim 1, is characterized in that: described solvent system is chloroform: methanol: water=4:3:3。
3. the method for claim 1, is characterized in that: described pH-zone refining countercurrent instrument column volume is 300mL。
4. the method for claim 1, is characterized in that: described applied sample amount 3g。
5. the method for claim 1, is characterized in that: described rotating speed 800rpm。
6. the method for claim 1, is characterized in that: described flow velocity 2.0mL/min。
7. the method for claim 1, is characterized in that: described detection wavelength 254nm。
8. the method for claim 1, is characterized in that: the extracting method of alkaloid compound in described Caulis Mahoniae: (1) adopts ethanol that Caulis Mahoniae medical material is extracted, and is concentrated into extracting solution vacuum without alcohol taste, obtains total extract；(2) total extract is adjusted to acidity, after petroleum ether extraction defat, adjusts to alkalescence, stirring precipitation, be Caulis Mahoniae alkaloid crude extract。
9. the method for claim 1, is characterized in that: what described application pH-zone refining countercurrent separated specifically comprises the following steps that
(1) by solvent system, be placed in separatory funnel, shake up rear stratification, after ready to balance a period of time will biphase up and down separately upper phase is fixing phase, and lower phase is mobile phase, is above added to 60mM hydrochloric acid, under be added to 7.5mM triethylamine；
(2) taking Caulis Mahoniae alkaloid crude extract and be dissolved in the mixed liquor of the upper and lower phase that volume ratio is 1:1 stand-by, described Caulis Mahoniae alkaloid crude extract is 3:10(g/mL with mixed liquor with magnitude relation)；
(3) first make semi-preparative high-speed counter-current chromatograph injection valve be in sample introduction state, pump fixing will be used mutually with 20mL min-1Flow velocity fills chromatography column, termination of pumping, opening speed controller, the chromatographic chromatography column of high velocity stream is made to rotate forward, when reaching setting speed, the sample syringe dissolved is injected in the liquid storage tube of counter-current chromatograph injection valve, rotate injection valve for connecing column state, sample is made to enter chromatography column, arranging flow rate of mobile phase is 1.5-2.5mL/min, starts pump mobile phase, then receives target component according to detector ultraviolet spectrogram, rotated evaporation, lyophilization obtains pressed powder。
10. the method for claim 1, is characterized in that: arranging flow rate of mobile phase in described step (3) is 2mL/min。
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Cited By (1)
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| CN110384697A (en) * | 2019-08-22 | 2019-10-29 | 深圳市药品检验研究院（深圳市医疗器械检测中心） | Anti-acetylcholinesterase activity composition and its screening technique and application in leatherleaf mahonia |
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| CN110384697A (en) * | 2019-08-22 | 2019-10-29 | 深圳市药品检验研究院（深圳市医疗器械检测中心） | Anti-acetylcholinesterase activity composition and its screening technique and application in leatherleaf mahonia |
| WO2021031579A1 (en) * | 2019-08-22 | 2021-02-25 | 深圳市药品检验研究院（深圳市医疗器械检测中心） | Anti-acetylcholinesterase active composition in caulis mahoniae and screening method therefor and application thereof |
| CN110384697B (en) * | 2019-08-22 | 2021-07-27 | 深圳市药品检验研究院（深圳市医疗器械检测中心） | Anti-acetylcholinesterase active composition in mahonia stem and screening method and application thereof |
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Application publication date: 20160622 Assignee: Beijing Emilion Technology Co., Ltd. Assignor: Shandong Analysis Test Center Contract record no.: X2019370000028 Denomination of invention: Method for separating alkaloidal compounds from Chinese mahonia stems with pH-zone-refining countercurrent chromatography Granted publication date: 20170825 License type: Exclusive License Record date: 20191213 |
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