CN104415573B - Method for classifying and preparing tertiary amine alkaloid and quaternary ammonium alkaloid from corydalis extract - Google Patents
Method for classifying and preparing tertiary amine alkaloid and quaternary ammonium alkaloid from corydalis extract Download PDFInfo
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Abstract
The invention provides a method for classifying and preparing tertiary amine alkaloid and quaternary ammonium alkaloid from corydalis extract. The method comprises the following steps of eluting different solvents according to a like component preparation method by adopting a C18/WCX (Weak cation exchange) type separating material with the combination of the hydrophobic effect and a weak cation exchange function, removing impurities, and enriching tertiary amine alkaloid and quaternary ammonium alkaloid, which are completely different in functional activity, contained in the corydalis extract respectively, wherein the total alkali contents in two like components can reach more than 65% and more than 90% respectively through HPLC (High Performance Liquid Chromatography) analysis. The preparation method has simple process, and has high efficiency and high recovery rate, the used separating material can be used repeatedly, the production cost is low, and the method can provide a good technical scheme for developing safe, efficient and controllable Chinese herbal preparations with alkaloids components.
Description
Technical field:
The invention belongs to Alkaloid separation technical field of purification, and in particular to a kind of preparation side of Chinese traditional medicine biology bases component
Method.
Background technology:
Rhizoma Corydalis(Rhizoma Corydalis)It is for the tuber of papaveraceae plant corydalis Corydalis yanhusuo W.T.Wang, warm in nature
Bitter in the mouth, energy promoting blood circulation to remove blood stasis, promoting the circulation of QI pain relieving is one of famous " eight Zhe's ", and medical value is quite high.Modern Pharmaceutical Chemistry and pharmacology
Learn experiment to show, the main active in Rhizoma Corydalis is two Alkaloid of tertiary amine and quaternary ammonium type, and wherein tertiary amine alkali content is about
0.65%, quaternary ammonium alkali content is about 0.3%(He Kai, Gao Jianli, Zhao Guangshu. Rhizoma Corydalis chemical composition, pharmacological action and quality control
Progress, Chinese herbal medicine, 2007,38 (12):1909-1912).This two constituents is not only variant in structure, in dissolubility
With also have very big difference in pharmacological action.It is biological for the tertiary amine-type of representative with Corydaline, B prime, C prime, D prime etc.
Alkali is practically insoluble in water, often acts on good antalgic and sedative, is the chief active that Rhizoma Corydalis are used for traditional pain management
Composition(Zhao's Aeschna melanictera, Zhao Xiaoqin, Li Yonghe. the comparative study of Content determination of dl-tetrahydropalmatine and analgesic activity, Xinjiang in Rhizoma Corydalis (processed with vinegar)
Chinese medicine, 2007,25 (2):34-36);It is and Rhizoma Corydalis are in the remarkable effect of the aspects such as myocardium keto consumption that resists myocardial ischemia, reduces, main
If because of the preferable quaternary ammonium base of water solublity(Cheng Xingye. Rhizoma Corydalis activity against myocardial ischemia site material basic research, association of China
With medical university's master thesis, 2008).Once had document report, effect of Rhizoma Corydalis is relevant with its concocting method, health product with
The composition of the fried liquid of processed product is identical, but tertiary amine alkali content is raised in processed product, and analgesic effect strengthens, and is used for controlling with regard to Rhizoma Corydalis
For treating coronary heart disease, health product is then better than processed product, and after main cause is exactly processing, quaternary ammonium alkali content is substantially reduced(Wang Guangning, Lee
Bravely. processing impact of the Rhizoma Corydalis to tetrahydropalmatine and 13-Methylpalmatine content, food and medicine, 2007,9 (8):1-2).It is aobvious
So, in Rhizoma Corydalis, two Alkaloid compositions, when a certain disease or card is treated, are all not effective.If can by this two class into
Screening respectively is divided to be enriched with out, while other substantial amounts of invalid components or interference component is also rejected, when a certain disease or card is treated,
Drug action will more targetedly, and main pharmacodynamics effect is more significantly, is also easier to be controlled its quality.And it is current,
Although being in great demand to corydalis alkaloid effective parts formulation, all it is mainly that extractum piece or Jing acid carry alkali deposited, ion
Total alkali after exchanger resin etc. is refined, not yet has the composition totally different to this two classes effect to carry out the standby method of classification system.
In view of this, propose the present invention.
The content of the invention
The present invention for realizing that different type alkaloid component is used for treating the treatment of different type indication in Rhizoma Corydalis, and
There is provided the classification preparation method of tertiary amine base and quaternary ammonium base in a kind of Rhizoma Corydalis extract.
In the Rhizoma Corydalis extract of the present invention, the classification preparation method of tertiary amine base and quaternary ammonium base is:First, Rhizoma Corydalis are extracted
Thing alcohol content 0~20% ethanol water or methanol water dissolution;2nd, ethanol will be arrived on solution obtained above or methanol is activated
And the good C18/WCX mixed model SPE posts of watering balance or post being prepared, the alcohol water wash with water or content below 10% first is removed
Fall the larger impurity of starch isopolarity, then with 10%~100% ethanol or methanol-eluted fractions, obtain tertiary amine alkaline constituentss, finally with
50%~100% ethanol containing 0.1%~10% acid or methanol-eluted fractions, obtain quaternary ammonium alkaline constituentss;3rd, by the tertiary amine base collected and season
Ammonium alkali cleaning takes off position, after concentration, freezes or is spray-dried.
The high performance liquid chromatography qualitative-and-quantitative method of tertiary amine bases component obtained by this method and quaternary ammonium bases component is:
Waters Alliance highly effective liquid phase chromatographic systems, on C18ME posts, with acetonitrile(A)And water(Containing 0.1% phosphoric acid,
0.2% triethylamine)Gradient elution is carried out for mobile phase, elution requirement is:0-20min,23%A;20-30min,23%-55%A;30-
45min,55%A.Flow velocity is 1mL/min, and PDA detectors, column temperature are 30 DEG C.For tertiary amine bases component, with tetrahydropalmatine it is
Reference substance makes external standard working curve, and gained regression equation is y=2E+07x+9190.1, R2=0.9999, Detection wavelength 280nm,
Range of linearity 0.005-0.1mg/mL.In tertiary amine bases component obtained by this method, the content of 6 main peaks is with tetrahydropalmatine(Fig. 1,
Peak 3)Meter is more than 65%.For quaternary ammonium bases component, external standard working curve is made by reference substance of dehydrogenation corybulbine, gained is returned
Equation is returned to be y=5E+07x-35237, R2=0.9996, Detection wavelength 280nm, range of linearity 0.005-0.1mg/mL.This method
In gained quaternary ammonium bases component, the content of 7 main peaks is with dehydrogenation corybulbine(Fig. 2, peak 4)Meter is more than 90%.
The present invention preparation method, process is simple, efficiently, the two Alkaloid component of tertiary amine and quaternary ammonium for preparing it is total
Alkali content respectively reaches 65% and more than 90%(HPLC is analyzed), purity is high, and is beneficial to quality control, be " safety, effectively, can
The exploitation of the alkaloidss tcm componentses preparation of control " is there is provided good technical scheme.
Description of the drawings
The uv atlas of the chromatogram and 6 main peaks of Fig. 1 tertiary amine bases components.
The uv atlas of the chromatogram and 7 main peaks of Fig. 2 quaternary ammonium bases components.
Specific embodiment
With reference to embodiment, the present invention is further elaborated, but these embodiments are definitely not any limit to the present invention
System.In embodiment, C18/WCX mixed model separation materials used are purchased from Zhejiang Acchrom Innovation Technology Co., Ltd..Embodiment
The tertiary amine-type alkaloidal constituent and quaternary ammonium type alkaloidal constituent of middle gained carries out qualitative and quantitative analysis using high performance liquid chromatography.
Embodiment one:
The methanolic extract extractum 200mg of Rhizoma Corydalis (processed with vinegar) is taken, is dissolved in the methanol-water of 10mL 5%, is obtained carrying for 20mg/mL
Take thing solution.10g C18/WCX fillers(40 μm of particle diameter) it is filled in open type SPE column jecket, first activated with 30mL methanol, then
30mL water balances are used, it is stand-by.Pour 10mL samples into above SPE posts blank pipe, the speed for controlling about 2mL/min is loaded to SPE posts
On, after loading is finished, with the methanol water wash of 60mL 10%, except the impurity component that depolarization is larger;Then with 60mL's 80%
Methanol is divided to two pipe eluting tertiary amine-type alkaloids;Then rinse colourless to eluent with pure methanol, remove weaker non-of other polarity
Alkaloid component;Finally, it is colourless to eluent with the methanol-eluted fractions quaternary ammonium type alkaloid containing 1% formic acid(About 20mL).Eluting is complete
Afterwards, SPE posts recover white, after watering balance, can loading again.
Embodiment two:
The methanolic extract extractum 200mg of Rhizoma Corydalis (processed with vinegar) is taken, is dissolved in the methanol-water of 10mL 5%, is obtained carrying for 20mg/mL
Take thing solution.10g C18/WCX fillers(40 μm of particle diameter) it is filled in open type SPE column jecket, 30mL Ethanol activations are first used, then
30mL water balances are used, it is stand-by.Pour 10mL samples into above SPE posts blank pipe, the speed for controlling about 2mL/min is loaded to filler
On, after loading is finished, with the ethanol water wash of 60mL 5%, except the impurity component that depolarization is larger;Then with the second of 60mL 50%
Alcohol is divided to two pipe eluting tertiary amine-type alkaloids;Then rinse colourless to eluent with straight alcohol, remove the weaker non-life of other polarity
Alkaloids composition;Finally, it is colourless to eluent with the 80% ethanol elution quaternary ammonium type alkaloid containing 1% acetic acid(About 50mL).Eluting is complete
Afterwards, SPE posts recover white, after watering balance, can loading again.
Embodiment three:
80% ethanol extraction extractum 200mg of Rhizoma Corydalis (processed with vinegar) is taken, is dissolved in 10mL water, the extract for obtaining 20mg/mL is molten
Liquid.10g C18/WCX fillers(40 μm of particle diameter) it is filled in open type SPE column jecket, 30mL Ethanol activations are first used, 30mL is then used
Water balance, it is stand-by.Pour 10mL samples into above SPE posts blank pipe, the speed for controlling about 2mL/min is loaded on filler, loading
After finishing, with the ethanol water wash of 60mL 5%, except the impurity component that depolarization is larger;Then it is divided to two with the ethanol of 60mL 50%
Pipe eluting tertiary amine-type alkaloid;Then rinse colourless to eluent with straight alcohol, remove the weaker non-alkaloid of other polarity into
Point;Finally, it is colourless to eluent with the 80% ethanol elution quaternary ammonium type alkaloid containing 1% acetic acid(About 50mL).After eluting is complete, SPE
Post recovers white, after watering balance, can loading again.
Example IV:
The water extract extractum 200mg of Rhizoma Corydalis (processed with vinegar) is taken, is dissolved in 10mL water, is obtained the extract solution of 20mg/mL.
10g C18/WCX fillers(40 μm of particle diameter) it is filled in open type SPE column jecket, 30mL Ethanol activations are first used, 30mL water is then used
Balance, it is stand-by.Pour 10mL samples into above SPE posts blank pipe, the speed for controlling about 2mL/min is loaded on filler, and loading is complete
Bi Hou, with the ethanol water wash of 60mL 5%, except the impurity component that depolarization is larger;Then it is divided to two pipes with the ethanol of 60mL 50%
Eluting tertiary amine-type alkaloid;Then rinse colourless to eluent with straight alcohol, remove the weaker non-alkaloid components of other polarity;
Finally, it is colourless to eluent with the 80% ethanol elution quaternary ammonium type alkaloid containing 1% acetic acid(About 50mL).After eluting is complete, SPE posts are extensive
Multiple white, after watering balance, can loading again.
Embodiment five:
The methanolic extract extractum 1g of Rhizoma Corydalis (processed with vinegar) is taken, is dissolved in the methanol-water of 50mL 5%, is obtained the extraction of 20mg/mL
Thing solution.C18/WCX chromatographic columns(20×250mm,40μm), flow velocity 20mL/min, Detection wavelength 280nm, single pump loading, single pump
Eluting.0-10min, 100% ethanol;10-20min, 100% water;20-22.5min, loading;22.5-32.5min, 100% water;
32.5-42.5min, 25% ethanol;42.5-52.5min, 40% ethanol;52.5-62.5min, 50% ethanol;62.5-72.5min,
100% ethanol;72.5-82.5min, -80% ethanol of 1% acetic acid.Tertiary amine-type alkaloid concentrates on 40% ethanol elution part;Quaternary ammonium type
Alkaloid concentrates on -80% ethanol elution part of 1% acetic acid.
Embodiment six:
80% ethanol extraction extractum 1g of Rhizoma Corydalis (processed with vinegar) is taken, is dissolved in 50mL water, is obtained the extract solution of 20mg/mL.
C18/WCX chromatographic columns(20×250mm,40μm), flow velocity 20mL/min, Detection wavelength 280nm, single pump loading, single pump eluting.0-
10min, 100% ethanol;10-20min, 100% water;20-22.5min, loading;22.5-32.5min, 100% water;32.5-
42.5min, 25% ethanol;42.5-52.5min, 40% ethanol;52.5-62.5min, 50% ethanol;62.5-72.5min, 100% second
Alcohol;72.5-82.5min, -80% ethanol of 1% acetic acid.Tertiary amine-type alkaloid concentrates on 40% ethanol elution part;Quaternary ammonium type alkaloid
Concentrate on -80% ethanol elution part of 1% acetic acid.
Embodiment seven:
The water extract extractum 1g of Rhizoma Corydalis (processed with vinegar) is taken, is dissolved in 50mL water, is obtained the extract solution of 20mg/mL.C18/
WCX chromatographic columns(20×250mm,40μm), flow velocity 20mL/min, Detection wavelength 280nm, single pump loading, single pump eluting.0-
10min, 100% ethanol;10-20min, 100% water;20-22.5min, loading;22.5-32.5min, 100% water;32.5-
42.5min, 25% ethanol;42.5-52.5min, 40% ethanol;52.5-62.5min, 50% ethanol;62.5-72.5min, 100% second
Alcohol;72.5-82.5min, -80% ethanol of 1% acetic acid.Tertiary amine-type alkaloid concentrates on 40% ethanol elution part;Quaternary ammonium type alkaloid
Concentrate on -80% ethanol elution part of 1% acetic acid.
Claims (8)
1. in a kind of Rhizoma Corydalis extract tertiary amine base and quaternary ammonium base classification preparation method, it is characterised in that the method include as
Lower step:
1) by Rhizoma Corydalis extract water, ethanol water or methanol water dissolution;
2) solution obtained above is loaded to into C18/WCX mixed model chromatographic columns, successively using water, ethanol water or water, methanol
Water wash and eluting;
3) tertiary amine base and quaternary ammonium base eluting position is collected respectively, after concentration and recovery organic solvent, freeze or be spray-dried.
2. preparation method according to claim 1, it is characterised in that:Described Rhizoma Corydalis extract is included with water, methanol
Or one or two or more kinds in ethanol is that solvent is slightly carried using what percolation, decoction, backflow, ultrasound or microwave radiation exaraction were obtained
Thing, or the crude extract total alkali extract again after acid carries alkali deposited, solvent distribution or resin column chromatography purification.
3. preparation method according to claim 1 and 2, it is characterised in that:Described Rhizoma Corydalis extract, first with containing
The aqueous solution of 0%~20% methanol or ethanol redissolves or dilutes.
4. preparation method according to claim 1, it is characterised in that:Described C18/WCX mixed model chromatographic columns, both may be used
Being the SPE post patterns of open type, it is also possible to be filled in chromatographic column column jecket, using preparative hplc pattern.
5. the preparation method according to claim 1 or 4, it is characterised in that:Described C18/WCX mixed model chromatographs are filled out
Material, is the separation material for being bonded C18 alkyl chains and-R-COOH on silica matrix, and which, need to first with 1 before specifically used
The methanol or Ethanol activation of~5 times of column volumes, then put down with the aqueous solution containing 0%~20% ethanol or methanol of 1~5 times of column volume
Weighing apparatus.
6. preparation method according to claim 1, it is characterised in that:The tool of described C18/WCX mixed model chromatographic columns
Body processing mode is:Described Rhizoma Corydalis extract solution is loaded to described C18/WCX by 1%~10% applied sample amount to mix
Syntype chromatographic column, after whole loadings are complete, with the ethanol or methanol aqueous solution drip washing of water or volume content 1%~10%, removes
The larger impurity of polarity, then with ethanol or the methanol-eluted fractions of volumetric concentration 10%~100%, obtains tertiary amine alkaline constituentss, then
With 50%~100% ethanol containing 0.1%~10% acid or methanol-eluted fractions, quaternary ammonium alkaline constituentss are obtained, finally will collect what is obtained
Tertiary amine base and quaternary ammonium alkaline constituentss, are concentrated respectively, after reclaiming organic solvent, are dried, are obtained this two Alkaloid.
7. the preparation method according to claim 1 or 6, it is characterised in that:The tertiary amine base for affording is because of poorly water-soluble, raw
Thing availability is poor, further can add one or two or more kinds in acetic acid, nitric acid, hydrochloric acid as needed in eluent, make
Be reacted to physiologically acceptable salt with alkaloid, to improve dissolubility.
8. the preparation method according to claim 1 or 6, it is characterised in that:Used by quaternary ammonium alkaline constituentss elution process
Acid be formic acid, acetic acid, nitric acid, hydrochloric acid, in sulphuric acid one or two or more kinds.
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