CN109678719A - A kind of extraction preparation method and applications of high-purity monomer salviol acid A - Google Patents
A kind of extraction preparation method and applications of high-purity monomer salviol acid A Download PDFInfo
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Abstract
The invention discloses a kind of extraction preparation methods of high-purity monomer salviol acid A (SLA-A), belong to pharmaceutical technology field, to solve the problems, such as that it is not high that the extraction of monomer salviol acid A (SLA-A) prepares finished product purity.Method is the following steps are included: extraction, removal of impurities, concentration, column chromatography separating monomer salviol acid A (SLA-A), concentrate drying.With the impurity in pillar layer separation monomer salviol acid A (SLA-A) in preparation method of the present invention, first separated using polyamide-based filler, it is separated later using sephadex filler, successively purified, remove undesired impurities, monomer salviol acid A (SLA-A) (content is greater than 99%) is made, content requirement has reached requirement of the chemicals to purity, and it is quality controllable, stable, so that drug activity improves 10 times or more compared with salvianolic acid, dosage can be greatly reduced, reduce various toxicities.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to a kind of extraction preparation method of high-purity monomer salviol acid A.
Background technique
All kinds of preparations of Radix Salviae Miltiorrhizae have been common drug at home, in clinical treatment cardiovascular and cerebrovascular disease, such as: angina pectoris, brain
Blood vessel accident etc. plays a very important role.Carrying out separation to the water soluble ingredient of Radix Salviae Miltiorrhizae in the prior art can be obtained pellet
Join phenolic acid A, B, C, D, E, F, G, Rosmarinic acid, alkannic acid, danshensu, the phenolic acid compounds such as protocatechualdehyde.Pharmacology
These phenolic acid compounds of the results show have the effects that antithrombotic, improve microcirculation, anti-cell lipid peroxidation injury.
Wherein salviol acid A activity is most strong, and root of red-rooted salvia phenolic acid B takes second place, and protocatechualdehyde and danshensu activity are most weak.Therefore, it extracts wherein
The most strong component salviol acid A of activity makes extract specific chemical components, and active constituent content is high, is the steady of raising red sage formulation
It is qualitative, drug quality is improved, improves drug effect, it is ensured that the key of curative effect.
Although salviol acid A (SLA-A) shows strongest physiological activity in clinical various aspects, its chemical property is not
Stablize, variation is easily decomposed under heating, illumination, acid condition, also can never study to obtain well in the prior art
The preparation process and extracting method of high-purity monomer salviol acid A (SLA-A), also just fail to obtain largely for New Drug Research
Salviol acid A sample further influences relative new drug development.
Summary of the invention
The purpose of the present invention is to provide a kind of extraction preparation methods of high-purity monomer salviol acid A, to solve monomer
The extraction of salviol acid A (SLA-A) prepares the not high problem of finished product purity.
In order to solve problem above, technical solution of the present invention are as follows:
A kind of extraction preparation method of high-purity monomer salviol acid A (SLA-A), comprising the following steps:
Step 1: extracting:
By salvia piece or red rooted salvia, using be heated to reflux, decoct, impregnate, diacolation, ultrasound, microwave or high pressure mode mention
It takes；
Step 2: removal of impurities:
Extracting solution filtering, natural subsidence or the solid impurity being centrifuged off in extracting solution；
Step 3: concentration:
Extracting solution normal pressure or reduced pressure carry out secondary removal of impurities to concentrate；
Step 4: column chromatography separating monomer salviol acid A (SLA-A):
A, chromatographic column is prepared using polyamide-based filler；
B, chromatographic column used is activated；
C, gained concentrate in step 3 is added into chromatographic column, is eluted, is removed with water, alcohol or alcohol-water solution or acetone-water solution
Impurity；
D, above-mentioned acquired solution alcohols, acetone, acetonitrile, alcohol solution, acetone-water solution or acetonitrile-aqueous solution are eluted, i.e.,
Obtain monomer salviol acid A (SLA-A) solution；
E, preparation chromatographic column is filled using sephadex and refines salviol acid A, 1-3 times repeatedly to get high-purity monomer Radix Salviae Miltiorrhizae
Phenolic acid A (SLA-A) solution；
Step 6: concentration, drying:
It is concentrated using conventional method, the accurate pH for controlling concentrate is 2.7-2.8, is dried, that is, monomer salviol acid A is made
(SLA-A)。
Further, the heavy method of water in step 3 specifically: by extracting solution normal pressure or reduced pressure, be added 3~8 times after cooling
The deionized water of medicinal material amount filters to get filtrate after standing.
Further, alcohol precipitation step in step 3 are as follows: by extracting solution normal pressure or reduced pressure, 3~5 times of medicines are added after cooling
The dehydrated alcohol of material amount, reconciling dehydrated alcohol concentration is 75%~80% progress alcohol precipitation, is filtered to get filtrate after standing.
Beneficial effects of the present invention are as follows:
With the impurity in pillar layer separation monomer salviol acid A in preparation method of the present invention, first separated using polyamide-based filler,
It is separated using sephadex filler, is successively purified later, remove undesired impurities, monomer salviol acid A (SLA- is made
A), with high purity, activity is good.
The present invention extracts preparation method and obtains the monomer salviol acid A (SLA-A) (content is greater than 99%) of high-purity, content
It is required that having reached requirement of the chemicals to purity, and quality controllable, stable, so that drug activity is improved compared with salvianolic acid
10 times or more, dosage can be greatly reduced, and monomer salviol acid A (SLA-A) physiological activity outstanding can guarantee drug
Safety, while the various toxicities that existing red sage formulation occurs are solved, class drug is protected for components in danshen cardiovascular and cerebrovascular
Clinical application brings new guarantee and hope.
The present invention provides monomer salviol acid A (SLA-A), it can be expected that for treating and preventing cardiovascular and cerebrovascular disease,
Specific chemical components, active constituent content height (optimal to can reach 99% or more), drug effect is significant；This method technical maturity, product
Quality is stablized, and can be mass produced, and has great importance for improving components in danshen preparation curative effect.
Specific embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
Embodiment 1
Step 1: extracting:
Salvia piece is taken, adds 9 times of deionized water amounts, soaking at room temperature 5 hours, adjusts pH value to 4.0, be then heated to 90~100 DEG C
Refluxing extraction 2 hours, separate first time extracting solution, then plus 6 times of deionized water amount, be heated to 90~100 DEG C of refluxing extractions 1.5
Hour, separate second of extracting solution；Merge extracting solution twice, the solid impurity being filtered to remove in extracting solution.
Step 2: removal of impurities:
It is 1.25 that the extracting solution normal pressure of step one kind, which is concentrated into relative density, and the deionized water of 5 times of medicinal material amounts is added after cooling
Precipitating stands, filters to get filtrate, and removes the solid impurity in extracting solution.
Step 3: concentration:
The concentration of extracting solution normal pressure is added the deionized water of 8 times of medicinal material amounts, filters to get filtrate after standing and carry out to concentrate after cooling
Secondary removal of impurities；
Step 4: column chromatography separating monomer salviol acid A (SLA-A):
A, chromatographic column is prepared using polyamide-based filler；
B, the activation of chromatographic column used；
C, gained concentrate in step 3 is added into the D101 large pore resin absorption column pre-processed, is separated, is first spent
Ionized water or 10% Diluted Alcohol elution, remove impurity, then use the ethanol elution of 30% concentration, collect contain the molten of salviandic acid A
Liquid；
D, 95% ethanol solution of above-mentioned acquired solution is eluted, collects eluent, ethyl alcohol is concentrated into and is use up to get monomer is arrived
Salviol acid A (SLA-A) solution；
E, preparation chromatographic column is filled using sephadex and refines salviol acid A, 3 times repeatedly to get high-purity monomer danshensu
Sour A (SLA-A) solution, through detecting, purity is up to 99%；
Step 6: concentration, drying:
It is concentrated using conventional method, the accurate pH for controlling concentrate is dried between 2.7-2.8, that is, monomer Radix Salviae Miltiorrhizae is made
Phenolic acid A (SLA-A).
Embodiment 2
Step 1: extracting:
It takes red rooted salvia to clean, adds 8 times of deionized water amounts, soaking at room temperature 2 hours, adjust pH value to 3.8, it is then heated to 90~
100 DEG C refluxing extraction 2 hours, separate first time extracting solution, then plus 5 times of deionized water amount, be heated to 90~100 DEG C of reflux and mention
It takes 1.5 hours, separates second of extracting solution；Merge extracting solution twice, the solid impurity being filtered to remove in extracting solution.
Step 2: removal of impurities:
It is 1.20 that the extracting solution normal pressure of step one kind, which is concentrated into relative density, and the deionized water of 5 times of medicinal material amounts is added after cooling
Precipitating stands, filters to get filtrate, and removes the solid impurity in extracting solution.
Step 3: concentration:
Extracting solution is concentrated under reduced pressure, and the deionized water of 3 times of medicinal material amounts is added after cooling, filters to get filtrate after standing and carries out to concentrate
Secondary removal of impurities；
Step 4: column chromatography separating monomer salviol acid A (SLA-A):
A, chromatographic column is prepared using polyamide-based filler；
B, the activation of chromatographic column used；
C, by step 3 gained concentrate add to the D101 large pore resin absorption column pre-processed, separated, spend from
Sub- water elution removes impurity, collects the solution containing salviandic acid A；
D, 85% acetone soln of above-mentioned acquired solution is eluted, collects eluent, acetone is concentrated into and is use up to get monomer is arrived
Salviol acid A (SLA-A) solution；
E, preparation chromatographic column is filled using sephadex and refines salviol acid A, 3 times repeatedly to get high-purity monomer danshensu
Sour A (SLA-A) solution, through detecting, purity is up to 99%；
Step 6: concentration, drying:
It is concentrated using conventional method, the accurate pH for controlling concentrate is dried between 2.7-2.8, that is, monomer Radix Salviae Miltiorrhizae is made
Phenolic acid A (SLA-A).
Embodiment 3
Step 1: extracting:
It takes red rooted salvia to clean, adds 10 times of deionized water amounts, soaking at room temperature 3 hours, adjust pH value to 3.6, it is then heated to 90~
100 DEG C refluxing extraction 2 hours, separate first time extracting solution, then plus 6 times of deionized water amount, be heated to 90~100 DEG C of reflux and mention
It takes 1.5 hours, separates second of extracting solution；Merge extracting solution twice, the solid impurity being filtered to remove in extracting solution.
Step 2: removal of impurities:
It is 1.10 that the extracting solution normal pressure of step one kind, which is concentrated into relative density, and the deionized water of 5 times of medicinal material amounts is added after cooling
Precipitating stands, filters to get filtrate, and removes the solid impurity in extracting solution.
Step 3: concentration:
The concentration of extracting solution normal pressure is added the deionized water of 5 times of medicinal material amounts, filters to get filtrate after standing and carry out to concentrate after cooling
Secondary removal of impurities；
Step 4: column chromatography separating monomer salviol acid A (SLA-A):
A, chromatographic column is prepared using polyamide-based filler；
B, the activation of chromatographic column used；
C, by step 3 gained concentrate add to the D101 large pore resin absorption column pre-processed, separated, spend from
Sub- water elution removes impurity, collects the solution containing salviandic acid A；
D, 90% acetonitrile solution of above-mentioned acquired solution is eluted, collects eluent, acetonitrile is concentrated into and is use up to get monomer is arrived
Salviol acid A (SLA-A) solution；
E, preparation chromatographic column is filled using sephadex and refines salviol acid A, 1 purifying is to get high-purity monomer danshensu
Sour A (SLA-A) solution, through detecting, purity is up to 99%；
Step 6: concentration, drying:
It is concentrated using conventional method, the accurate pH for controlling concentrate is dried between 2.7-2.8, that is, monomer Radix Salviae Miltiorrhizae is made
Phenolic acid A (SLA-A).
Embodiment 4
Difference from Example 1 is: step 3 is alcohol precipitation step: extracting solution normal pressure being concentrated, 3 times of medicinal materials are added after cooling
The dehydrated alcohol of amount, reconciling dehydrated alcohol concentration is 75% progress alcohol precipitation, is filtered to get filtrate after standing.
Embodiment 5
Difference from Example 2 is: step 3 is alcohol precipitation step: extracting solution normal pressure being concentrated, 5 times of medicinal materials are added after cooling
The dehydrated alcohol of amount, reconciling dehydrated alcohol concentration is 85% progress alcohol precipitation, is filtered to get filtrate after standing.
Embodiment 6
Difference from Example 3 is: step 3 is alcohol precipitation step: extracting solution normal pressure being concentrated, 4 times of medicinal materials are added after cooling
The dehydrated alcohol of amount, reconciling dehydrated alcohol concentration is 80% progress alcohol precipitation, is filtered to get filtrate after standing.
The present invention has carried out following experiments to confirm that the monomer salviol acid A (SLA-A) made of this method is improving the heart
Application and curative effect in myocardial ischemia drug.
There is used material in following confirmatory experiment:
Monomer salviol acid A (SLA-A) is prepared by embodiment 1.
The danshen of control experiment group and the physiological saline of pseudo- operation group are the circulation drug of market purchase.
Experimental example 1: monomer salviol acid A (SLA-A) closes the influence of mouse tracheae ECG extinction time to folder.
Routinely experimental method tests mouse, and experimental result is as follows:
1 monomer salviol acid A (SLA-A) of table closes the influence of mouse ECG extinction time to tracheae folder
Note: P < 0.001 compared with physiological saline group * * *
Positive drug danshen, which has, it can be seen from 1 data of table extends the work that folder closes mouse tracheae mouse electrocardio extinction time
With with significant difference compared with model group.The high, medium and low dosage of salviol acid A all has the apparent folder that extends and closes mouse tracheae
And extend the time of mouse electrocardio disappearance, with significant difference compared with model group.
Experimental example 2: monomer salviol acid A (SLA-A) induces pituitrin the influence of myocardial ischemia in rats.
It learns from else's experience and screens qualified rat 50, weight 200-280g, 270.1 ± 13.0g of average weight, half male and half female, at random
It is respectively classified into five groups, every group 10, successive administration 14 days, 30 minutes after the last administration, with 1.5% yellow Jackets 30mg/kg
Intraperitoneal injection of anesthesia is faced upward position and is fixed on young animal dissecting table, and rat four limbs and chest install electrocardiogram needle electrode, calibration electricity
Pressure is 1mv/cm, low speed 50mm/ seconds, traces V3 normal ECG, then injects pituitrin 0.6U/ in rat tail vein
Kg traces V3 electrocardiogram immediately, and every 15 seconds record electrocardiograms are primary in 1 minute, and it is primary to trace within every 30 seconds in 2 minutes electrocardiogram,
It is primary to trace within every 1 minute in 2-5 minutes electrocardiogram, i.e., (15 seconds, 30 seconds, 45 seconds, 60 seconds, 1 point 30 seconds, 2 points, 3 points, 4 points, 5 points
The electrocardiogram of clock), it is measured on electrocardiogram and compares T after groups of animals injection of pituitrin and involve the ischemic of S-T segment and become
Change, carries out statistical procedures and compare the difference between physiological saline group and administration group, evaluate the function of resisting myocardial ischemia of drug, portion
Dividing the results are shown in Table 2.
2 monomer salviol acid A (SLA-A) of table to pituitrin induce myocardial ischemia in rats electrocardiogram influence (X ±
SD)
Note: P < 0.05 compared with physiological saline group *
P < 0.01 compared with physiological saline group *
Experimental example 3:
Influence of the monomer salviol acid A (SLA-A) to thrombus in rabbit body.
Rabbit 30 are taken, half male and half female, weight 2.0-3.0kg is randomly divided into five groups, every group 6.By rabbit Ethylurethanm
After 1g/kg ear vein injecting anesthetic, faces upward position and be fixed on rabbit autopsy table, cut off the hair in front of neck, operation separation neck after disinfection
A piece sewing-needle with floss silk is penetrated intravascular about 2cm or more along arteria carotis communis, opens artery by total artery about 2.5cm
Folder, flows freely blood in the blood vessels, after 2 hours, puts to death animal, carefully cuts blood vessel, carefully split blood vessel, taking-up has
The floss silk of thrombus claims the weight in wet base of thrombus on weighing scale to test twisting force, compares administration group with the weight of control group thrombus, the results are shown in Table 4.
Influence of the 3 monomer salviol acid A (SLA-A) of table to thrombus in rabbit body
Note: P < 0.05 compared with saline control group *
P < 0.01 compared with saline control group *
P < 0.001 compared with saline control group * *
Table 3 statistics indicate that, salviol acid A have obviously inhibit rabbit body in thrombosis, keep the weight of thrombus obviously low
In model control group.
Experimental example 4: influence of the monomer salviol acid A (SLA-A) to rat's blood stasis model hemorheology.
Taking rat 60, weight 200-250g, half male and half female is randomly divided into 6 groups, and every group 10, before experiment, continuous 14 days
Administration, 40 minutes after the last administration, respectively by adrenaline subcutaneous injection 0.08ml/100g weight, totally 2 times, two minor ticks 4 hours,
(front and back is respectively spaced 2 hours) immerses rat in ice water 5 minutes between double injection Adr, stops eating after disposition, secondary morning takes blood examination
It surveys.
Morning takes blood, and 3.8% citrate anticoagulation of blood forbids the grumeleuse for having small in blood, uses Chengdu Instruement Factory
NXE-1B cone and plate viscometer measures each group whole blood specific viscosity, serum specific viscosity, fibrin specific viscosity, RBC hematocrit and red
Cell electrophoresis and blood coagulation time.It the results are shown in Table 4.
Influence of the 4 monomer salviol acid A (SLA-A) of table to rat's blood stasis model hemorheological property
Note: P < 0.05 compared with model group *
P < 0.01 compared with model group *
P < 0.001 compared with model group * *
Can be seen that salviol acid A can change the variation of blood stasis hemorheology of rat by 4 data of table, to blood contrast viscosity,
Blood plasma specific viscosity, clotting time and platelet aggregation all have the effect of being substantially reduced, by this test it can be proved that salviol acid A
Can make viscous, dense, thick, aggregation the situation of blood stasis rat blood is improved.
Experimental example 5: influence of the monomer salviol acid A (SLA-A) to rat brain endoperoxides object.
Taking rat 60, weight 180-220g, half male and half female is randomly divided into six groups, and every group 10, using literature method,
Successive administration 14 days, last dose 40 minutes, operation separation rat bilateral carotid, folder closed after five minutes, restored blood stream
It is dynamic, administration is injected intravenously after 24 hours again, rat sacrificed by decapitation, operation brain was taken into 1 hour, 10% brain homogenate is prepared, by document side
Method measures LPO content in brain tissue, the results are shown in Table 6.
5 monomer salviol acid A (SLA-A) of table is to the influence to rat brain endoperoxides lipid
Note: P < 0.05 compared with model control group *
P < 0.01 compared with model control group *
As can be seen from Table 5, salviol acid A can be such that the generation of rat brain endoperoxides object subtracts after a certain period of time in administration
It is few, to show body from the injury of some harmful substances.
Other animal acute toxicity test shows: the half lethal dose (LD of mouse mainline administration50) it is 2.0g
/kg。
Claims (3)
1. a kind of extraction preparation method of high-purity monomer salviol acid A, comprising the following steps:
Step 1: extracting:
By salvia piece or red rooted salvia, using be heated to reflux, decoct, impregnate, diacolation, ultrasound, microwave or high pressure mode mention
It takes；
Step 2: removal of impurities:
Extracting solution filtering, natural subsidence or the solid impurity being centrifuged off in extracting solution；
Step 3: concentration:
Extracting solution normal pressure or reduced pressure carry out secondary removal of impurities to concentrate；
Step 4: column chromatography separating monomer salviol acid A:
A, chromatographic column is prepared using polyamide-based filler；
B, chromatographic column used is activated；
C, gained concentrate in step 3 is added into chromatographic column, is eluted, is removed with water, alcohol or alcohol-water solution or acetone-water solution
Impurity；
D, above-mentioned acquired solution alcohols, acetone, acetonitrile, alcohol solution, acetone-water solution or acetonitrile-aqueous solution are eluted, i.e.,
Obtain monomer salviol acid A solution；
E, preparation chromatographic column is filled using sephadex and refines salviol acid A, 1-3 times repeatedly to get high-purity monomer Radix Salviae Miltiorrhizae
Phenolic acid solution A；
Step 6: concentration, drying:
It is concentrated using conventional method, the accurate pH for controlling concentrate is 2.7-2.8, is dried, that is, monomer root of red-rooted salvia phenolic acid is made
A。
2. a kind of extraction preparation method of high-purity monomer salviol acid A as described in claim 1, it is characterised in that: described
The heavy method of water in step 3 specifically: by extracting solution normal pressure or reduced pressure, the deionized water of 3~8 times of medicinal material amounts is added after cooling,
It filters to get filtrate after standing.
3. a kind of extraction preparation method of high-purity monomer salviol acid A as described in claim 1, it is characterised in that: described
Alcohol precipitation step in step 3 are as follows: by extracting solution normal pressure or reduced pressure, the dehydrated alcohol of 3~5 times of medicinal material amounts is added after cooling, adjusts
Solving dehydrated alcohol concentration is 75%~80% progress alcohol precipitation, is filtered to get filtrate after standing.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1958555A (en) * | 2006-10-30 | 2007-05-09 | 王煜 | Method for preparing salviol acid A |
| CN101041620A (en) * | 2006-07-13 | 2007-09-26 | 正大青春宝药业有限公司 | Preparation method of salvia miltiorrhiza tanshinoate A |
| CN102219685A (en) * | 2010-04-16 | 2011-10-19 | 北京本草天源药物研究院 | Method for preparing salvianolic acid A of salvia miltiorrhiza |
| CN102464586A (en) * | 2010-11-12 | 2012-05-23 | 天津天士力制药股份有限公司 | Preparation method of danshinolic acid A |
| CN103570548A (en) * | 2013-10-17 | 2014-02-12 | 浙江永宁药业股份有限公司 | Preparation method of salvinaolic acid A |
-
2019
- 2019-02-22 CN CN201910134282.7A patent/CN109678719A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101041620A (en) * | 2006-07-13 | 2007-09-26 | 正大青春宝药业有限公司 | Preparation method of salvia miltiorrhiza tanshinoate A |
| CN1958555A (en) * | 2006-10-30 | 2007-05-09 | 王煜 | Method for preparing salviol acid A |
| CN102219685A (en) * | 2010-04-16 | 2011-10-19 | 北京本草天源药物研究院 | Method for preparing salvianolic acid A of salvia miltiorrhiza |
| CN102464586A (en) * | 2010-11-12 | 2012-05-23 | 天津天士力制药股份有限公司 | Preparation method of danshinolic acid A |
| CN103570548A (en) * | 2013-10-17 | 2014-02-12 | 浙江永宁药业股份有限公司 | Preparation method of salvinaolic acid A |
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Application publication date: 20190426 |