CN101186572A - Method for separating and purifying salvianolic acid from red sage root liquid extract by one step - Google Patents
Method for separating and purifying salvianolic acid from red sage root liquid extract by one step Download PDFInfo
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Abstract
The invention relates to a method for further separating and purifying salvianolic acid from Danshen extract fluid, which comprises preparing, breaking and extracting Danshen via water solution, acidifying the extracting solution to adjust pH and adding salt to process post-treatment, processing dynamic continuous adsorption and elution on the treated extract at chromatography column stuffed with resin adsorbent, eluting via water, collecting and concentrating eluent, eluting via gradient ethanol solution, segmented collecting and concentrates eluent and drying the concentrates solution to obtain product. The invention realizes a method for separating and purifying various salvianolic acids in a simple, effective and fast manner, wherein test on different salvianolic acid products shows that the highest yields of tanshinol, alkannic acid, rosmarinic acid, salvianolic acid A and salvianolic acid B are 35. 55%, 70.65%, 99.27%, 82.78%, and 89.34%, and relative highest purities are 95.32%, 65.05%, 29.40%, 33.93%, and 82.35%, which are near or higher than the result of purification on the goal of single component.
Description
Technical field
The present invention relates to natural phant functional component extractive technique, particularly a kind of from the red sage root aqueous extract method of one step separation and purification salvianolic acid, be specifically related to easy from red sage root aqueous extract, efficiently, the method for the multiple salvianolic acid of separation and purification apace.
Background technology
The red sage root (Salvia miltiorrhiza Bunge) is a kind of per nnial herb, be the Labiatae Salvia, its dry root is a traditional Chinese medical science time-honored simply drug for invigorating blood circulation and eliminating stasis commonly used, has " numbness of dispelling is good for pin; menstruation regulating is only collapsed, detoxify and drain pus for promoting the circulation of QI to relieve pain, tranquillizing by calming the heart; clearing heat and cooling blood; promoting blood circulation and removing blood stasis, nourishing blood and invigorating qi " eight large effects.
The water soluble component of the red sage root has pharmacological action widely; as protect myocardial ischemia-anoxemia, microcirculation improvement, maincenter calmness, anticoagulant and thrombosis etc.; used it for treatment of diseases such as coronary heart disease, stenocardia, myocardial infarction, ishemic stroke clinically, drug effect is remarkable.Wherein several important compound have its special effect again, as: Salvianic acidA is coronary artery dilator significantly, and blood flow increasing improves ATP content in cardiac muscle and the cerebral tissue, thereby under ischemic or anaerobic conditions, can obviously dwindle myocardial infarct size; The effect pharmacology of rancinamycin IV is similar to Salvianic acidA, also has the coronary artery dilator effect, is the effective constituent of red sage root protection cardiovascular systems, and the cells of vascular wall adhesion that can prophylaxis of tumours necrosis factor-alpha (TNF-α) causes; Salvianolic acid A can effectively reduce the concentration of alanine aminotransferase and TNF-α in the serum; The expression of rosmarinic acid energy inflammation-inhibiting molecule and the activity of HIV-1 intergrase; Alkannic acid is a kind of anti-HIV-1 compounds of many target spots; To showing that with in vitro study salvianolic acid B magnesium can resist the rats'liver damage that D-galactosamine causes, reduces the hepatic necrosis degree in the rat liver body.Therefore, if can obtain the higher salvianolic acid component of multiple purity simultaneously, then can develop the pharmaceutical use of the red sage root to greatest extent.
At present, obtaining of red sage root water soluble ingredient adopted methods such as water extract-alcohol precipitations, ethyl acetate extraction, document (Chinese patent medicine, 2007,29 (1): 143-144 more; Herbal medicine, 2007,38 (6): 843-846; Herbal medicine, 2007,38 (4): 542-545; The time precious traditional Chinese medical science traditional Chinese medicines, 2007,18 (5): 1186-1187) all elaborate, but products obtained therefrom or be the polyphenol acid mixture, structure activity relationship is undistinct; Or obtain a certain single effective substance through the multistep purifying again, adopt water to carry-step purifying Salvianic acidAs such as twin columns absorb-elute-solvent extraction as CN1342638A, CN1303052C adopts water or alcohol extracting-precursor conversion-ultrafiltration removal of impurities-solvent extraction-multistep purifying Salvianic acidAs such as normal-phase chromatography, CN1751706A adopts alkali to carry-multistep purifying Salvianic acidAs such as acidifying-alcohol precipitation-twin columns (resin+polymeric amide) absorb-elute-crystallization, CN101012163A adopts adsorption and desorption by resin-recrystallization or secondary chromatography purification Salvianic acidA, CN1425659 adopts water to carry-number step separation and purification salvianolic acid Bs such as acidifying-column chromatography-drying, all be to extract purification of target with the one-component in above-mentioned each example, other functional components do not relate to.CN1305866C adopts multisteps such as twice boiling water extraction-high speed centrifugation-membrane filtration removal of impurities or solvent extraction-reversed phase chromatography separation to obtain salvianolic acid A, B and three kinds of components of rancinamycin IV, but parameters such as purity and yield do not report, and is batch treatment, goes up sample 5ml at every turn.Therefore, still do not have a kind of easy and simple to handlely at present, extraction efficiency and product purity and treatment capacity are all higher, and the method for the multiple salvianolic acid of separation and purification simultaneously.
Summary of the invention
The object of the invention be to provide a kind of from the red sage root aqueous extract method of the multiple salvianolic acid of one step separation and purification, this method is easy and simple to handle, can a step separation and purification prepare 5 kinds of salvianolic acids.
Provided by the invention a kind of from the red sage root water extract method of separation and purification salvianolic acid may further comprise the steps:
1) gets red rooted salvia, pulverize, use extraction with aqueous solution;
2) acidifying adjust pH in the extracting solution, and carry out aftertreatment with salt;
3) extracting solution after handling is at the enterprising action attitude of the chromatography column of having filled sorbent material continuous adsorption, wash-out: earlier with water elution, collect elutriant, concentrate; With gradient ethanolic soln wash-out, the Fractional Collections elutriant concentrates again; Concentrated solution is drying to obtain product.
The invention provides a kind of from the red sage root aqueous extract method of one step separation and purification multiple salvianolic acid mainly may further comprise the steps:
1) gets red rooted salvia, pulverize, use extraction with aqueous solution;
2) extracting solution adds acid for adjusting pH value, to remove floss; With salt to strengthen the adsorptive power of resin to material;
3) extracting solution after handling is at the enterprising action attitude of the chromatography column of having filled sorbent material continuous adsorption, wash-out: earlier with water elution, collect elutriant, concentrate; With gradient ethanolic soln wash-out, the Fractional Collections elutriant concentrates again; Concentrated solution is drying to obtain product.
Step 1) employing water is carried the water soluble component in the red sage root, obtains comprising total phenolic acids extraction liquid of multiple salvianolic acid.Described extracting method is a kind of in pickling process, percolation, microwave extraction method, ultrasonic method or the Enzymatic Extraction, preferred Enzymatic Extraction (CN1884558), extracting solution can be handled through alcohol precipitation or without alcohol precipitation, when being performance assessment criteria with the product yield, preferably without the extracting solution of alcohol precipitation.
Step 2) acid described in is selected from: one or more in hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetate or the perchloric acid etc., and preferred hydrochloric acid, concentration is 1～4%; PH value scope is 1～5, preferred pH=3.5; Adopt the floss in centrifugal or the suction method removal extracting solution, preferred centrifuging, rotating speed is 5500 rev/mins; Described salt is following a kind of or more than one combinations: sodium-chlor, sodium sulfate, ammonium sulfate etc., preferred sodium-chlor.
The sorbent material that adopts in the step 3) is a kind of among weak-base ion-exchange resin D392, D380 or D301R, strong polar macroporous adsorption resin NKA-9, polar macroporous adsorption resin X-5, low-pole macroporous adsorbent resin SP825 or the AB-8, preferred low-pole macroporous resin SP825; Last sample pH between 2～8, preferred pH=3.5; Last sample salt concn 1%～4%, preferred 2%; Last sample and eluting temperature are 20～40 ℃, preferred 25 ℃; Dynamically during water elution with the velocity flow of 0.5～5 times of sorbent material volume per hour through adsorption column, preferable flow rate is 1.33 times of sorbent material volumes per hour, the collection elutriant, principal constituent is a Salvianic acidA; Dynamically ethanol gradient elution liquid is 10～80% aqueous ethanolic solutions, and preferred 10%, 20%, 40%, 60% and 80% aqueous ethanolic solution substitutes successively; During ethanol gradient elution with the velocity flow of 0.5～5 times of sorbent material volume per hour through adsorption column, preferable flow rate is 1.5 times of sorbent material volumes per hour; Fractional Collections, effluent volume are that 2～8 times (preferred effluent volume is 5 times of resin volume) of resin volume are a component unit, and wherein component I is that alkannic acid, component I I are that rosmarinic acid, component III are that salvianolic acid A, component I V are salvianolic acid B; Concentrate and adopt normal pressure or vacuum rotary steam method of enrichment; Dry adopt a kind of in spraying drying or the lyophilize.
Each salvianolic acid product of gained is measured through efficient liquid phase chromatographic analysis and shown: the highest yield of Salvianic acidA, alkannic acid, rosmarinic acid, salvianolic acid A and salvianolic acid B is respectively 35.55%, 70.65%, 99.27%, 82.78% and 89.34%, and highest purity is respectively 95.32%, 65.05%, 29.40%, 33.93%, 82.35%.Wherein chromatographiccondition is as follows: chromatographic column is YMC-PackODS-A C18 (150 * 4.6mm column, 5 μ m); Column temperature is a room temperature; The detection wavelength is 280nm; Flow velocity is 1.0ml/min; Sample size is 20 μ l; Mobile phase A is a water: acetic acid (volume ratio)=100: 0.5; Mobile phase B is an acetonitrile: water: acetic acid (volume ratio)=95: 5: 0.5, and the stratographic analysis gradient sees Table 1:
Moving phase gradient in table 1 stratographic analysis
| Time (min) | Mobile phase A (%) | Mobile phase B (%) |
| 0 1.5 10 29 36 52 | 100 100 88 77 70 60 | 0 0 12 23 30 40 |
Step 2) purpose that adds sour adjust pH is precipitated impurities, avoids stopping up resin bed in the dynamic adsorption or sneaking in the finished product; Step 2) purpose with salt is to utilize salting out to reduce the solubleness of salvianolic acid in the aqueous solution, thereby strengthens the adsorptive power of resin to it; Adsorptive power between the ethanol gradient elution in the step 3), the salvianolic acid that not only can progressively destroy opposed polarity and resin and realize that component separates, but also can reduce because the resin bubble that the rate of expansion difference is produced in different solvents.
Characteristics of the present invention are to adopt a step resin absorption, the purification treating method of wash-out, obtain the salvianolic acid of multiple higher degree simultaneously, core technology is (to comprise sample pH by sample and elution requirement on the optimization regulation and control resin, last sample salt concn, last sample and eluting temperature, last sample and elution flow rate, the elutriant alcohol concn, Fractional Collections liquid is long-pending etc.), and easy realization component is separated and the purpose of high-purity preparation, and various polyphenol acid (Salvianic acidA, salvianolic acid B, salvianolic acid A, alkannic acid, rosmarinic acid) purity, it is the purifying process gained result (seeing table 2 for details) of target with the one-component at present that yield is close to or higher than.
The purity and yield comparison of salvianolic acid when table 2 adopts different extracting and purifying method
| Method | Extract the purifying thing | Purity | Yield |
| CN1342638A CN1303052C CN1868994A CN1751706A CN101012163A CN1425659 is of the present invention | Salvianic acidA Salvianic acidA Salvianic acidA Salvianic acidA Salvianic acidA salvianolic acid B Salvianic acidA salvianolic acid B | ＞30％ ＞95％ ＞94％ ＞90％ ＞90％ ＞90％ ＞95％ ＞82％ | —— ＞70％ —— —— ＞1.8％ —— ＞35％ ＞89％ |
Description of drawings
Fig. 1 adopts the high-efficient liquid phase chromatogram of gained Salvianic acidA of the present invention.
Fig. 2 adopts the high-efficient liquid phase chromatogram of gained salvianolic acid B of the present invention.
Embodiment
Embodiment 1
(1) water extract-alcohol precipitation: get red rooted salvia and be crushed to 20～35 orders,, add 95% ethanol and make that alcohol volume content reaches 60% in the extracting solution with 15 times of water extraction, centrifugation behind 4 ℃ of refrigeration 24h, rotating speed is 5500 rev/mins, reclaims supernatant liquor, revolve steaming to there not being ethanol, get red sage root water extract-alcohol precipitation liquid.
(2) acidifying is with salt: water intaking is carried 200 milliliters of usefulness 4% hydrochloric acid of precipitation solution (mass concentration) and is transferred pH to 3.5, and flocks is removed in centrifuging, and rotating speed is 5500 rev/mins, adds 4g sodium-chlor again.
(3) go up sample, wash-out: through the extracting solution of above-mentioned processing under 25 ℃ with 1.33 times of resin volumes/hour flow velocity to flow through diameter be 19 millimeters, length-to-diameter ratio is 1: 10, and is filled with the chromatography column of low-pole macroporous adsorbent resin SP825, carries out dynamic adsorption; Behind the end of the sample, with 250 ml distilled waters with 1.33 times of resin volumes/hour flow velocity carry out dynamic desorption, collect water elution liquid; Use distilled water and 95% alcoholic acid mixed solution (the two volume ratio is respectively 10%, 20%, 40%, 60% and 80%) to proceed dynamic gradient elution subsequently, elution flow rate be 1.5 times of resin volumes/hour, the elutriant of per 5 times of resin volumes is a component unit, collects corresponding 4 unitary ethanolic soln elutriants.
(4) concentrate drying: 1 part of water elution liquid and 4 parts of ethanolic soln elutriants are revolved inspissation respectively contract, 5 partial concentration liquid cooling freeze-drying are dry to obtain 5 kinds of power-products.
(5) check and analysis: through efficient liquid phase chromatographic analysis proof each several part product in turn the yield of corresponding Salvianic acidA, alkannic acid, rosmarinic acid, salvianolic acid A and salvianolic acid B be respectively 32.14%, 68.07%, 38.81%, 33.03% and 76.08%, purity is respectively 85.83%, 63.00%, 24.08%, 31.70%, 86.58%.
Embodiment 2
(1) water is carried: get red rooted salvia and be crushed to 20～35 orders, with 15 times of water extraction.
(2) acidifying is with salt: water intaking 200 milliliters of usefulness 4% hydrochloric acid of extract (mass concentration) are transferred pH to 3.5, and flocks is removed in centrifuging, and rotating speed is 5500 rev/mins, adds 4g sodium-chlor again.
(3) go up sample, wash-out: through the extracting solution of above-mentioned processing under 25 ℃ with 1.33 times of resin volumes/hour flow velocity to flow through diameter be 19 millimeters, length-to-diameter ratio is 1: 10, and is filled with the chromatography column of low-pole macroporous adsorbent resin SP825, carries out dynamic adsorption; Behind the end of the sample, with 250 ml distilled waters with 1.33 times of resin volumes/hour flow velocity carry out dynamic desorption, collect water elution liquid; Use distilled water and 95% alcoholic acid mixed solution (the two volume ratio is respectively 10%, 20%, 40%, 60% and 80%) to proceed dynamic gradient elution subsequently, elution flow rate be 1.5 times of resin volumes/hour, the elutriant of per 5 times of resin volumes is a component unit, collects corresponding 4 unitary ethanolic soln elutriants.
(4) concentrate drying: 1 part of water elution liquid and 4 parts of ethanolic soln elutriants are revolved inspissation respectively contract, 5 partial concentration liquid cooling freeze-drying are dry to obtain 5 kinds of power-products.
(5) check and analysis: through efficient liquid phase chromatographic analysis proof each several part product in turn the yield of corresponding Salvianic acidA, alkannic acid, rosmarinic acid, salvianolic acid A and salvianolic acid B be respectively 35.55%, 70.65%, 99.27%, 82.78% and 89.34%, purity is respectively 95.32%, 65.05%, 29.40%, 33.93%, 82.35%.
Claims (10)
1. the method for the multiple salvianolic acid of separation and purification from red sage root water extract is characterized in that may further comprise the steps:
1) gets red rooted salvia, pulverize, use extraction with aqueous solution;
2) acidifying adjust pH in the extracting solution, and carry out aftertreatment with salt;
3) extracting solution after handling is at the enterprising action attitude of the chromatography column of having filled sorbent material continuous adsorption, wash-out: earlier with water elution, collect elutriant, concentrate; With gradient ethanolic soln wash-out, the Fractional Collections elutriant concentrates again; Concentrated solution is drying to obtain product.
2. the method for the multiple salvianolic acid of separation and purification from red sage root water extract is characterized in that mainly may further comprise the steps:
1) gets red rooted salvia, pulverize, use extraction with aqueous solution;
2) acidifying adjust pH in the extracting solution, and carry out aftertreatment with salt;
3) extracting solution after handling is at the enterprising action attitude of the chromatography column of having filled sorbent material continuous adsorption, wash-out: earlier with water elution, collect elutriant, concentrate; With gradient ethanolic soln wash-out, the Fractional Collections elutriant concentrates again; Concentrated solution is drying to obtain product;
Described water extraction is pickling process, percolation, microwave extraction method, ultrasonic method or Enzymatic Extraction, and extracting solution is handled through alcohol precipitation or without alcohol precipitation;
Described acidifying is to be selected from: one or more in hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetate or the perchloric acid; Described salt is sodium-chlor, sodium sulfate or ammonium sulfate;
Described sorbent material is a kind of among weak-base ion-exchange resin D392, D380 or D301R, strong polar macroporous adsorption resin NKA-9, polar macroporous adsorption resin X-5, low-pole macroporous adsorbent resin SP825 or the AB-8.
3. method as claimed in claim 2 is characterized in that described acid is the hydrochloric acid of 1～4% mass percentage concentration, transfers pH=1～5.
4. method as claimed in claim 2 is characterized in that described salt is sodium-chlor.
5. method as claimed in claim 2 is characterized in that described aftertreatment is with the floss in centrifugal or the suction method removal extracting solution.
6. method as claimed in claim 2 is characterized in that described sorbent material is low-pole macroporous resin SP825; Last sample pH is between 2～8, last sample salt concn 1%～4%, last sample and eluting temperature are 20～40 ℃, dynamically during water elution with the velocity flow of 0.5～5 times of sorbent material volume per hour through adsorption column, dynamically ethanol gradient elution liquid is 10～80% aqueous ethanolic solutions, during ethanol gradient elution with the velocity flow of 0.5～5 times of sorbent material volume per hour through adsorption column, Fractional Collections, effluent volume are that 2～8 times of resin volume are a component unit.
7. method as claimed in claim 6 is characterized in that the described sample pH=3.5 of going up; Last sample and eluting temperature are 25 ℃; Dynamically flow velocity is 1.33 times of sorbent material volumes per hour during water elution, collects elutriant, and dynamic ethanol gradient elution liquid is that 10%, 20%, 40%, 60% and 80% aqueous ethanolic solution substitutes successively; Flow velocity is 1.5 times of sorbent material volumes per hour during ethanol gradient elution; Fractional Collections, every section effluent volume are 5 times of resin volume.
8. method as claimed in claim 2 is characterized in that concentrated employing normal pressure described in the step 3) or vacuum rotary steam concentrate.
9. method as claimed in claim 2 is characterized in that dry employing spraying drying or lyophilize in the step 3).
10. the salvianolic acid that obtains of the described method of claim 2-10.
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| CN102249920A (en) * | 2011-05-30 | 2011-11-23 | 上海朗萨医药科技有限公司 | Preparation method of high-purity salvianolic acid A |
| CN102351701A (en) * | 2011-10-27 | 2012-02-15 | 广州汉方现代中药研究开发有限公司 | Method for separating and purifying rosmarinic acid from Tibetan radix salviae miltiorrhizae |
| CN102351819A (en) * | 2011-10-27 | 2012-02-15 | 广州汉方现代中药研究开发有限公司 | Extraction, purification and preparation method of high-purity salvianolic acid B |
| CN101638401B (en) * | 2008-07-29 | 2012-11-21 | 上海医药工业研究院 | Method for preparing high-purity danshinolic acid B |
| CN102993143A (en) * | 2012-12-27 | 2013-03-27 | 成都普思生物科技有限公司 | Method for rapidly separating alkannic acid monomer from salviae miltiorrhizae |
| CN103083298A (en) * | 2012-11-20 | 2013-05-08 | 蒋春红 | Application of salvianolic acid A composition in preparing medicines for protecting ischemic brain tissue damage |
| CN103083297A (en) * | 2012-11-20 | 2013-05-08 | 蒋春红 | Application of salvianolic acid A composition in preparing medicines for improving neural function symptom after cerebral ischemia |
| CN103083295A (en) * | 2012-11-20 | 2013-05-08 | 陆文萍 | Application of salvianolic acid A freeze-dried powder injection in preparing medicines for improving neural function symptom after cerebral ischemia |
| CN103570654A (en) * | 2013-10-17 | 2014-02-12 | 兰赫(上海)生物科技有限公司 | Method for preparing alkannic acid |
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| CN102249920B (en) * | 2011-05-30 | 2013-09-25 | 上海朗萨医药科技有限公司 | Preparation method of high-purity salvianolic acid A |
| CN102249920A (en) * | 2011-05-30 | 2011-11-23 | 上海朗萨医药科技有限公司 | Preparation method of high-purity salvianolic acid A |
| CN102351701A (en) * | 2011-10-27 | 2012-02-15 | 广州汉方现代中药研究开发有限公司 | Method for separating and purifying rosmarinic acid from Tibetan radix salviae miltiorrhizae |
| CN102351819A (en) * | 2011-10-27 | 2012-02-15 | 广州汉方现代中药研究开发有限公司 | Extraction, purification and preparation method of high-purity salvianolic acid B |
| CN102351819B (en) * | 2011-10-27 | 2014-05-14 | 广州白云山汉方现代药业有限公司 | Extraction, purification and preparation method of high-purity salvianolic acid B |
| CN103083297A (en) * | 2012-11-20 | 2013-05-08 | 蒋春红 | Application of salvianolic acid A composition in preparing medicines for improving neural function symptom after cerebral ischemia |
| CN103083295A (en) * | 2012-11-20 | 2013-05-08 | 陆文萍 | Application of salvianolic acid A freeze-dried powder injection in preparing medicines for improving neural function symptom after cerebral ischemia |
| CN103083295B (en) * | 2012-11-20 | 2016-01-06 | 江西青峰药业有限公司 | Salvianolic acid A freeze-dried powder is for the preparation of the purposes improving the function of nervous system's symptom medicine after cerebral ischemia |
| CN103083298A (en) * | 2012-11-20 | 2013-05-08 | 蒋春红 | Application of salvianolic acid A composition in preparing medicines for protecting ischemic brain tissue damage |
| CN103083297B (en) * | 2012-11-20 | 2015-11-25 | 江西青峰药业有限公司 | Salvianolic acid A compositions is for the preparation of the purposes improving the function of nervous system's symptom medicine after cerebral ischemia |
| CN102993143A (en) * | 2012-12-27 | 2013-03-27 | 成都普思生物科技有限公司 | Method for rapidly separating alkannic acid monomer from salviae miltiorrhizae |
| CN103570654A (en) * | 2013-10-17 | 2014-02-12 | 兰赫(上海)生物科技有限公司 | Method for preparing alkannic acid |
| CN103570654B (en) * | 2013-10-17 | 2018-04-27 | 兰赫(上海)生物科技有限公司 | A kind of preparation method of alkannic acid |
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| CN103667371B (en) * | 2013-11-11 | 2016-03-16 | 天津大学 | A kind of biological production of Salvianic acidA |
| CN104761520A (en) * | 2015-04-10 | 2015-07-08 | 大连工业大学 | Method for preparing high-purity salvianolic acid B employing salt precipitation |
| CN105456359A (en) * | 2015-12-22 | 2016-04-06 | 贵州景峰注射剂有限公司 | Method for effectively removing color of radix salviae miltiorrhizae extracting solution |
| CN113402489A (en) * | 2021-04-16 | 2021-09-17 | 宁波大学 | Method for efficiently preparing salvianolic acid B and lithospermic acid |
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