CN104415573A - 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 PDF

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CN104415573A
CN104415573A CN201310409003.6A CN201310409003A CN104415573A CN 104415573 A CN104415573 A CN 104415573A CN 201310409003 A CN201310409003 A CN 201310409003A CN 104415573 A CN104415573 A CN 104415573A
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ethanol
quaternary ammonium
water
acid
alkaloid
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CN104415573B (en
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梁鑫淼
王超然
郭秀洁
张秀莉
郭志谋
薛兴亚
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Zhongke Yulin Energy Technology Operation Co ltd
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Dalian Institute of Chemical Physics of CAS
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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

The classification system Preparation Method of tertiary amine base and quaternary ammonium base in a kind of Corydalis P.E
Technical field:
The invention belongs to Alkaloid separation technical field of purification, be specifically related to a kind of preparation method of Chinese traditional medicine biology bases component.
Background technology:
Corydalis tuber (corydalis tuber) is the stem tuber of papaveraceae plant corydalis Corydalis yanhusuo W.T.Wang, bitter warm in nature, and energy promoting blood circulation to remove blood stasis, sharp gas pain relieving, be one of famous " eight Zhe's ", medical value is quite high.Modern Pharmaceutical Chemistry and pharmacological experiment show, main active in corydalis tuber is tertiary amine and quaternary ammonium type two Alkaloid, wherein tertiary amine base content is about 0.65%, quaternary ammonium base content is about 0.3%(He Kai, Gao Jianli, Zhao Guangshu. corydalis tuber chemical composition, pharmacological action and quality controling research progress, Chinese herbal medicine, 2007,38 (12): 1909-1912).This two constituents is not only structurally variant, and dissolubility and pharmacological action also have very large difference.With Corydaline, B prime, C prime, D primes etc. are that the tertiary amine-type alkaloid of representative is water-soluble hardly, often have good antalgic and sedative effect, main active (the Zhao emerald of corydalis tuber for traditional pain management, Zhao Xiaoqin, Li Yonghe. the comparative study of Content determination of dl-tetrahydropalmatine and analgesic activity in Rhizoma Corydalis (processed with vinegar), Xinjiang traditional Chinese medicine, 2007,25 (2): 34-36); And corydalis tuber resisting myocardial ischemia, reduce remarkable effect in myocardium keto consumption etc., mainly because of water-soluble good quaternary ammonium base (Cheng Xingye. the basic research of corydalis tuber activity against myocardial ischemia site material, China Concord Medical Science University's master thesis, 2008).Once had bibliographical information, effect of YANHUSU is relevant with its concocting method, and raw product are identical with the composition of the fried liquid of processed product, but tertiary amine base content raises in processed product, analgesic effect strengthens, and is used for the treatment of with regard to coronary heart disease with regard to corydalis tuber, and raw product are then better than processed product, after main cause is concocted exactly, quaternary ammonium base content obviously reduces (Wang Guangning, Li Yong. concoct the impact of corydalis tuber on tetrahydropalmatine and dehydrocorydaline content, food and pharmaceutical, 2007,9 (8): 1-2).Obviously, in corydalis tuber, two Alkaloid compositions are when treating a certain disease or card, are not all effective.If this two constituents can be screened enrichment out respectively, also reject other a large amount of invalid components or interference components, when treating a certain disease or card, drug action will have more specific aim simultaneously, main pharmacodynamics effect is more remarkable, also easilier controls its quality.And at present, although being in great demand to corydalis alkaloid effective parts formulation, being all mainly medicinal extract sheet or carrying alkali through acid and sink, the total alkali after ion exchange resin etc. are refining, 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, the present invention is proposed.
Summary of the invention
The present invention realizes dissimilar alkaloid component in corydalis tuber to be used for the treatment of the treatment of dissimilar indication, and provides the classification system Preparation Method of tertiary amine base and quaternary ammonium base in a kind of Corydalis P.E.
In Corydalis P.E of the present invention, the classification system Preparation Method of tertiary amine base and quaternary ammonium base is: one, by Corydalis P.E alcohol content 0 ~ 20% ethanol water or methanol-water dissolve; Two, activate to ethanol or methyl alcohol the C18/WCX mixed mode SPE post or preparative column that also watering balance is good by solution obtained above, first with the alcohol water wash of water or content less than 10%, remove the impurity that starch isopolarity is larger, then ethanol or the methanol-eluted fractions of 10% ~ 100% is used, obtain tertiary amine base component, finally to contain 50% ~ 100% ethanol or the methanol-eluted fractions of 0.1% ~ 10% acid, obtain quaternary ammonium base component; Three, by the tertiary amine base collected and quaternary ammonium base wash-out position, after concentrated, freezing or spraying dry.
The high performance liquid chromatography qualitative-and-quantitative method of this method gained tertiary amine bases component and quaternary ammonium bases component is:
Waters Alliance highly effective liquid phase chromatographic system, on C18ME post, with acetonitrile (A) and water (containing 0.1% phosphoric acid, 0.2% triethylamine), for mobile phase carries out gradient elution, elution requirement is: 0-20min, 23%A; 20-30min, 23%-55%A; 30-45min, 55%A.Flow velocity is 1mL/min, PDA detector, and column temperature is 30 DEG C.For tertiary amine bases component, be that reference substance makes external standard working curve with tetrahydropalmatine, gained regression equation is y=2E+07x+9190.1, R 2=0.9999, determined wavelength 280nm, range of linearity 0.005-0.1mg/mL.In this method gained tertiary amine bases component, the content of 6 main peaks is greater than 65% with tetrahydropalmatine (Fig. 1, peak 3) meter.For quaternary ammonium bases component, with dehydrogenation corybulbine for reference substance makes external standard working curve, gained regression equation is y=5E+07x-35237, R 2=0.9996, determined wavelength 280nm, range of linearity 0.005-0.1mg/mL.In this method gained quaternary ammonium bases component, the content of 7 main peaks is greater than 90% with dehydrogenation corybulbine (Fig. 2, peak 4) meter.
Preparation method of the present invention, technique is simple, efficiently, the total alkali of the tertiary amine prepared and quaternary ammonium two Alkaloid component can reach more than 65% and 90% (HPLC analysis) respectively, purity is high, and is beneficial to quality control, for the exploitation of the alkaloids tcm components preparation of " safety; effectively, controlled " provides good technical scheme.
Accompanying drawing explanation
The chromatogram of Fig. 1 tertiary amine bases component and the uv atlas of 6 main peaks.
The chromatogram of Fig. 2 quaternary ammonium bases component and the uv atlas of 7 main peaks.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is further elaborated, but these embodiments are never any limitation of the invention.C18/WCX mixed mode parting material used in embodiment is all purchased from Zhejiang Acchrom Innovation Technology Co., Ltd..In embodiment, the tertiary amine-type alkaloidal constituent of gained and quaternary ammonium type alkaloidal constituent all adopt high performance liquid chromatography to carry out qualitative and quantitative analysis.
Embodiment one:
Get the methanolic extract medicinal extract 200mg of Rhizoma Corydalis (processed with vinegar), be dissolved in the methanol-water of 10mL 5%, obtain the extract solution of 20mg/mL.10g C18/WCX filler (particle diameter 40 μm) is loaded in open type SPE column jecket, first with the activation of 30mL methyl alcohol, then uses 30mL water balance, stand-by.Pour 10mL sample into above SPE post blank pipe, the speed controlling about 2mL/min is loaded on SPE post, after loading, with the methanol-water drip washing of 60mL 10%, except the impurity component that depolarization is larger; Then two pipe wash-out tertiary amine-type alkaloids are divided with the methyl alcohol of 60mL 80%; Then colourless to eluent by pure washed with methanol, remove the non-alkaloid components that other polarity are more weak; Finally, with containing the methanol-eluted fractions quaternary ammonium type alkaloid of 1% formic acid to eluent colourless (about 20mL).After wash-out is complete, SPE post recovers white, after watering balance, and can loading again.
Embodiment two:
Get the methanolic extract medicinal extract 200mg of Rhizoma Corydalis (processed with vinegar), be dissolved in the methanol-water of 10mL 5%, obtain the extract solution of 20mg/mL.10g C18/WCX filler (particle diameter 40 μm) is loaded in open type SPE column jecket, first uses 30mL Ethanol activation, then uses 30mL water balance, stand-by.Pour 10mL sample into above SPE post blank pipe, the speed controlling about 2mL/min is loaded on filler, after loading, with the ethanol water wash of 60mL 5%, except the impurity component that depolarization is larger; Then two pipe wash-out tertiary amine-type alkaloids are divided with the ethanol of 60mL 50%; Then rinse colourless to eluent with straight alcohol, remove the non-alkaloid components that other polarity are more weak; Finally, with containing 80% ethanol elution quaternary ammonium type alkaloid of 1% acetic acid to eluent colourless (about 50mL).After wash-out is complete, SPE post recovers white, after watering balance, and can loading again.
Embodiment three:
Get 80% ethanol extract medicinal extract 200mg of Rhizoma Corydalis (processed with vinegar), be dissolved in 10mL water, obtain the extract solution of 20mg/mL.10g C18/WCX filler (particle diameter 40 μm) is loaded in open type SPE column jecket, first uses 30mL Ethanol activation, then uses 30mL water balance, stand-by.Pour 10mL sample into above SPE post blank pipe, the speed controlling about 2mL/min is loaded on filler, after loading, with the ethanol water wash of 60mL 5%, except the impurity component that depolarization is larger; Then two pipe wash-out tertiary amine-type alkaloids are divided with the ethanol of 60mL 50%; Then rinse colourless to eluent with straight alcohol, remove the non-alkaloid components that other polarity are more weak; Finally, with containing 80% ethanol elution quaternary ammonium type alkaloid of 1% acetic acid to eluent colourless (about 50mL).After wash-out is complete, SPE post recovers white, after watering balance, and can loading again.
Embodiment four:
Get the water extract medicinal extract 200mg of Rhizoma Corydalis (processed with vinegar), be dissolved in 10mL water, obtain the extract solution of 20mg/mL.10g C18/WCX filler (particle diameter 40 μm) is loaded in open type SPE column jecket, first uses 30mL Ethanol activation, then uses 30mL water balance, stand-by.Pour 10mL sample into above SPE post blank pipe, the speed controlling about 2mL/min is loaded on filler, after loading, with the ethanol water wash of 60mL 5%, except the impurity component that depolarization is larger; Then two pipe wash-out tertiary amine-type alkaloids are divided with the ethanol of 60mL 50%; Then rinse colourless to eluent with straight alcohol, remove the non-alkaloid components that other polarity are more weak; Finally, with containing 80% ethanol elution quaternary ammonium type alkaloid of 1% acetic acid to eluent colourless (about 50mL).After wash-out is complete, SPE post recovers white, after watering balance, and can loading again.
Embodiment five:
Get the methanolic extract medicinal extract 1g of Rhizoma Corydalis (processed with vinegar), be dissolved in the methanol-water of 50mL 5%, obtain the extract solution of 20mg/mL.C18/WCX chromatographic column (20 × 250mm, 40 μm), flow velocity 20mL/min, determined wavelength 280nm, single pump loading, single pump wash-out.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, 1% acetic acid-80% ethanol.Tertiary amine-type alkaloid concentrates on 40% ethanol elution part; Quaternary ammonium type alkaloid concentrates on 1% acetic acid-80% ethanol elution part.
Embodiment six:
Get 80% ethanol extract medicinal extract 1g of Rhizoma Corydalis (processed with vinegar), be dissolved in 50mL water, obtain the extract solution of 20mg/mL.C18/WCX chromatographic column (20 × 250mm, 40 μm), flow velocity 20mL/min, determined wavelength 280nm, single pump loading, single pump wash-out.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, 1% acetic acid-80% ethanol.Tertiary amine-type alkaloid concentrates on 40% ethanol elution part; Quaternary ammonium type alkaloid concentrates on 1% acetic acid-80% ethanol elution part.
Embodiment seven:
Get the water extract medicinal extract 1g of Rhizoma Corydalis (processed with vinegar), be dissolved in 50mL water, obtain the extract solution of 20mg/mL.C18/WCX chromatographic column (20 × 250mm, 40 μm), flow velocity 20mL/min, determined wavelength 280nm, single pump loading, single pump wash-out.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, 1% acetic acid-80% ethanol.Tertiary amine-type alkaloid concentrates on 40% ethanol elution part; Quaternary ammonium type alkaloid concentrates on 1% acetic acid-80% ethanol elution part.

Claims (8)

1. the classification system Preparation Method of tertiary amine base and quaternary ammonium base in Corydalis P.E, it is characterized in that, the method comprises the steps:
1) Corydalis P.E use water, ethanol water or methanol-water are dissolved;
2) solution obtained above is loaded to C18/WCX mixed mode chromatographic column, adopts water, ethanol water or water, methanol-water drip washing and wash-out successively;
3) tertiary amine base and quaternary ammonium base wash-out position is collected respectively, after concentration and recovery organic solvent, freezing or spraying dry.
2. preparation method according to claim 1, it is characterized in that: it is the crude extract that solvent adopts the extracting modes such as diacolation, decoction, backflow, ultrasonic or microwave radiation technology and obtains that described Corydalis P.E comprises with one or two or more kinds in water, methyl alcohol or ethanol, or the total alkali extract of this crude extract again after peracid carries that alkali sinks, solvent distributes or the mode such as resin column chromatography purifies.
3. preparation method according to claim 1 and 2, is characterized in that: described Corydalis P.E, first redissolves or dilution with the aqueous solution containing 0% ~ 20% methyl alcohol or ethanol, wherein, is preferably 0% ~ 10%.
4. preparation method according to claim 1, is characterized in that: described C18/WCX mixed mode chromatographic column, both can be the SPE post pattern of open type, and also can load in chromatographic column column jecket, adopts preparative chromatography pattern.
5. the preparation method according to claim 1 or 4, it is characterized in that: described C18/WCX mixed mode chromatograph packing material, it is the parting material of bonding C18 alkyl chain and-R-COOH on silica matrix, it is before concrete use, need first with methyl alcohol or the Ethanol activation of 1 ~ 5 times of column volume, then with the aqueous equilibrium containing 0% ~ 20% ethanol or methyl alcohol of 1 ~ 5 times of column volume.
6. preparation method according to claim 1, it is characterized in that: the concrete processing mode of described C18/WCX mixed mode chromatographic column is: by described Corydalis P.E solution by 1% ~ 10% applied sample amount be loaded to described C18/WCX mixed mode chromatographic column, after whole loading is complete, with ethanol or the methanol aqueous solution drip washing of water or volume content 1% ~ 10%, remove the impurity that starch isopolarity is larger, then use ethanol or the methanol-eluted fractions of volumetric concentration 10% ~ 100%, obtain tertiary amine base component; Finally by 50% ~ 100% ethanol or the methanol-eluted fractions that contain 0.1% ~ 10% acid, obtain quaternary ammonium base component;
Finally will collect the tertiary amine base and quaternary ammonium base component that obtain, concentrate respectively, after reclaiming organic solvent, dry, obtain this two Alkaloid.
7. the preparation method according to claim 1 or 6, it is characterized in that: the tertiary amine base that wash-out obtains is because of poorly water-soluble, bioavilability is poor, one or two or more kinds in the acid of the living things system compatibilities such as acetic acid, nitric acid, hydrochloric acid, sulfuric acid can be added further as required in eluent, make it to be reacted into alkaloid into physiologically acceptable salt, to improve dissolubility.
8. the preparation method according to claim 1 and 5, it is characterized in that: in quaternary ammonium base component elution process, acid used is one or two or more kinds in formic acid, acetic acid, nitric acid, hydrochloric acid, sulfuric acid etc., can, according to the needs produced, use different acid to obtain different quaternary ammonium alkali salts; Or also can first with after formic acid or acetic acid wash-out, in eluent, add the strong acid such as hydrochloric acid or sulfuric acid replace and obtain strong acid salt.
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CN110960578A (en) * 2018-09-29 2020-04-07 泰州医药城国科化物生物医药科技有限公司 Method for classifying and preparing tertiary amine alkali and quaternary ammonium alkali in corydalis tuber extract
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CN110974874A (en) * 2019-08-05 2020-04-10 泰州医药城国科化物生物医药科技有限公司 Method for preparing flavone and saponin components in spina date seed extract
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CN110974874A (en) * 2019-08-05 2020-04-10 泰州医药城国科化物生物医药科技有限公司 Method for preparing flavone and saponin components in spina date seed extract

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