CN109810082A - A kind of extraction separation method of tanshin polyphenolic acid B - Google Patents

A kind of extraction separation method of tanshin polyphenolic acid B Download PDF

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CN109810082A
CN109810082A CN201910059866.2A CN201910059866A CN109810082A CN 109810082 A CN109810082 A CN 109810082A CN 201910059866 A CN201910059866 A CN 201910059866A CN 109810082 A CN109810082 A CN 109810082A
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resin
tanshin polyphenolic
polyphenolic acid
solution
extraction separation
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CN109810082B (en
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刘东锋
于霞
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Nanjing Zelang Biotechnology Co Ltd
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Jiangsu Deze Biotechnology Co Ltd
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Abstract

The invention discloses a kind of extraction separation methods of tanshin polyphenolic acid B: (1) choosing red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;(2) extract: according to parts by weight, weighing 1 part of red rooted salvia medicine materical crude slice, be added 12 parts of water of pH5.0, be added the zytase of every gram of medicinal material 5-15U, rebaudioside and/or stevioside, 38-45 DEG C reaction 2-3 hours, cool down, filtered fluid be obtained by filtration;(3) it purifies: 1/5th of the original volume of extracting solution vacuum concentration is purified using macroporous absorbent resin.Integrated use zytase of the present invention, rebaudioside and stevioside can effectively shorten the time of enzymatic treatment, and also can protect the activity of tanshin polyphenolic acid B in purification process, thus the stability of the tanshin polyphenolic acid B during increasing substantially extraction purification.The two exclusive use has this effect, and combining more has synergy.

Description

A kind of extraction separation method of tanshin polyphenolic acid B
Technical field
The present invention relates to a kind of extraction separation methods of tanshin polyphenolic acid B, belong to technical field of bioengineering.
Background technique
Radix Salviae Miltiorrhizae, Chinese medicine name.For the dry root and rhizome of Lamiaceae plant Radix Salviae Miltiorrhizae Salvia miltiorrhiza Bge.. Spring, the excavation of two season of autumn, silt is removed, it is dry.National most area is all distributed.It is inducing meastruation to relieve menalgia with promoting blood circulation, clear away heart-fire The effect of relieving restlessness, cool blood to disappear carbuncle.For chest impediment and cardialgia, stomach duct and abdomen hypochondriac pain, a lump in the abdomen causing distension and pain, hot numbness pain, dysphoria and insomnia, and menstruation is not It adjusts, dysmenorrhea menostasis, sore swell and ache curative.
In terms of being concentrated mainly on liposoluble constituent to the early stage research of effective component in red sage, more than 40 chemical combination have been obtained Object.These compounds can be divided into two classes, i.e., tanshinone (o-quinone type) and enumerate ketone (adjacent hydroxyl paraquinoid).Tanshinone Compound majority belongs to diterpene compound, and wherein most is diterpene quinone.Such as Tanshinone I, Tanshinone II -A, Radix Salviae Miltiorrhizae II-B of ketone, tanshinone III, isotanshinone I, IsotanshinoneⅡ-A, Cryptotanshinone, different Cryptotanshinone, hydroxyl Tanshinone II -A, two Hydrogen Tanshinone I, left-handed dihydrotanshinone I, neotanshinone A, neotanshinone B, neotanshinone C, new Cryptotanshinone II, ring phenol The new Cryptotanshinone of lactamide, oleoyl and oleoyl danshenxinkun A etc..By the effort of decades, people are to fat soluble ingredient of red sage root It obtains than more comprehensively recognizing, and important discovery is also achieved to the bioactivity research of various composition, it was demonstrated that these The clinical application drug that a batch works well is developed in the pharmacological action of compound.Tanshin polyphenolic acid B is three molecule danshensus and one point Sub- caffeic acid is combined into.Tanshin polyphenolic acid B is the highest water-soluble phenolic sour component of content in Radix Salviae Miltiorrhizae, is accounted in the pharmacological action of Radix Salviae Miltiorrhizae There is critical role.But tanshin polyphenolic acid B is easily degraded, various catabolites have again in aqueous solution because its chemical structure is unstable Complicated pharmacological activity.This not only brings very big difficulty to the preparation process of red sage root water soluble ingredient drug, and is possible to drop The clinical efficacy of its low related preparations.
The damp and hot degradation of tanshin polyphenolic acid B meets first order kinetics in Salvia miltiorrhiza Bge water extract, and reaction rate constant is in heating temperature, pH Positive correlation, wherein temperature is greater than the influence of pH to the influence of reaction rate constant K.Thus, when extracting separation tanshin polyphenolic acid B The time that Radix Salviae Miltiorrhizae impregnates, water is mentioned, is concentrated and dried should be shortened, avoid long-time heating under alkaline condition, and will be as far as possible The resting period for shortening solution state makes Salvia miltiorrhiza Bge water extract solidification that can reduce tanshin polyphenolic acid B loss as early as possible.In addition, should be as far as possible Guarantee to save under low pH, high concentration and cryogenic conditions, to keep tanshin polyphenolic acid B stability in aqueous solution.
Currently, application of the biological enzyme in traditional Chinese medicine technology is further extensive, especially in the extraction process of Chinese medicine, obtain Significant effect.Enzyme reaction needs certain condition.Under optimum conditions, active most strong, the catalytic capability shown of enzyme It is most strong.
The present invention is intended to provide a kind of extraction separation method of the tanshin polyphenolic acid B of environment-friendly high-efficiency, tanshin polyphenolic acid B during the separation process Stability is high, and degradation rate is low, and makes full use of biotechnology, environment-friendly high-efficiency.
Summary of the invention
The object of the present invention is to provide a kind of extraction separation methods of the tanshin polyphenolic acid B of environment-friendly high-efficiency, red during the separation process Phenolic acid B stability is high, and degradation rate is low, and makes full use of biotechnology, environment-friendly high-efficiency.The structural formula of tanshin polyphenolic acid B is as follows:
Stevia is a kind of natural sweet taste of high sugariness for extracting from stevia rebaudian leaf non-nutritive low in calories Agent.Currently, eight kinds of glucosides are had found from stevia, i.e. Stevioside (slevioside), rebaudioside (RebaudiosideA, B, C, D, E), (Dul~ide ties up primary glucoside (steviobi~siti) Lai Baodi with this to Dul-A The sugariness highest of glucoside A, greater than 300 times of sucrose, and taste matter is best, is free of any bad pleasant impression, is a kind of ideal Crude sweet hides agent, and extraction prepares the research heat that the high stevia rebaudianum sugar product of content rebaudioside-A content is domestic and international stevioside production industry Point
Stevioside (being commonly called as stevioside, steviol glycoside) is one kind from catananche's STEVIA REBAUDIANA (or stevia rebaudian leaf) The new type natural sweetener that essence mentions, and South America uses STEVIA REBAUDIANA to have centuries history as medicinal herbs and for sugar.
The applicant for the first time applies to rebaudioside and stevioside in the extraction separation of tanshin polyphenolic acid B, with Lay Bao Enlightening glucoside and stevioside can effectively shorten the time of enzymatic treatment, and also can protect tanshin polyphenolic acid B in purification process Activity, thus the stability of the tanshin polyphenolic acid B during increasing substantially extraction purification.The two exclusive use has this effect, group More there is synergy altogether.
Technical problems to be solved needed for the present invention can be achieved through the following technical solutions.
A kind of extraction separation method of tanshin polyphenolic acid B, its step are as follows:
(1) it chooses red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;
(2) it extracts: according to parts by weight, weighing 1 part of red rooted salvia medicine materical crude slice, 12 parts of water of pH5.0 are added, every gram of medicinal material is added The zytase of 5-15U, rebaudioside and/or stevioside, 38-45 DEG C reaction 2-3 hours, it is cooling, filtered fluid is obtained by filtration;
(3) it purifies: 1/5th of the original volume of extracting solution vacuum concentration is purified using macroporous absorbent resin.
Preferably, the step (3) are as follows:
95% ethyl alcohol impregnates resin 18-20 hours, is swollen it sufficiently, selects glass column, is rinsed and is set using 95% ethyl alcohol Rouge column washes away the organic impurities in resin containing band.The washing of first deionization, 5% hydrochloric acid solution impregnate, and drain acid solution, then spend from Sub- water is cleaned, and 2-4% sodium hydroxide solution is added and washes, then deionization washing, removes water-solubility impurity in resin.Use 50% second The HCL solution of alcohol rinses resin column.Extract loading is cleaned using a small amount of deionized water, and effective component is attracted to macroreticular resin It is interior.With 50% ethanol-eluting resin column, the eluent of purifying is collected, solution is dried in vacuo, obtains product.
Advantages of the present invention:
(1) integrated use zytase of the present invention, rebaudioside and stevioside can effectively shorten enzymatic treatment when Between, and also can protect in purification process the activity of tanshin polyphenolic acid B, thus the red phenol during increasing substantially extraction purification The stability of sour B.The two exclusive use has this effect, and combining more has synergy.
(2) it directly from red rooted salvia medicine materical crude slice, does not need to crush, a step can be obtained the very high extracting solution of recovery rate.
Specific embodiment
The embodiment of the present invention is described below in detail, described the examples are only for explaining the invention, and should not be understood as pair Limitation of the invention.
Specific embodiments of the present invention are as described below.
The present invention uses prior art conventional H PLC detection effective content and recovery rate:
2.83 milligrams of tanshin polyphenolic acid B standard items accurately are weighed, is placed in 5 milliliters of volumetric flasks, deionized water constant volume shakes up, and makees For reference substance solution.
According to official method: mobile phase is methanol-acetonitrile-formic acid-water (30:10:1:59).Detection wavelength is 286nm.It is right It is respectively 1,2,4,8,16 μ L according to product solution sample volume, successively carries out high performance liquid chromatography detection.Using peak area as ordinate, into Sample amount is abscissa, draws standard curve.
According to methanol eddy recovery rate as reference: taking red rooted salvia several, crush, sieve with 100 mesh sieve, take medicinal powder 1 Gram, 250 milliliters of 75% methanol is added, weighed weight is heated to reflux 1 hour, is taken out, and it is cooling, weight is supplied with 75% methanol, is shaken It is even, filtrate is obtained by filtration.
The test of sample size: sample volume is 5 μ l, and tanshin polyphenolic acid B in crude drug is calculated according to standard curve in sample detection Content be 3.58%.
Embodiment 1
A kind of extraction separation method of tanshin polyphenolic acid B, its step are as follows:
(1) it chooses red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;
(2) it extracts: according to parts by weight, weighing red rooted salvia medicine materical crude slice 50g, the water 600g of pH5.0 is added, every gram of medicinal material is added The zytase of 10U, rebaudioside 1g, 40 DEG C are reacted 3 hours, cooling, and filtered fluid is obtained by filtration;
Liquid is supplied, is 3.68% according to the recovery rate that tanshin polyphenolic acid B is calculated in standard curve.
(3) it purifies: 1/5th of the original volume of extracting solution vacuum concentration is purified using macroporous absorbent resin.
The step (3) are as follows:
95% ethyl alcohol impregnates resin 18 hours, is swollen it sufficiently, selects glass column, uses 95% alcohol flushing resin Column washes away the organic impurities in resin containing band.First deionization washing, 5% hydrochloric acid solution impregnate, and drain acid solution, then use deionization Water is cleaned, and 2% sodium hydroxide solution is added and washes, then deionization washing, removes water-solubility impurity in resin.Use 50% ethyl alcohol HCL solution rinses resin column.Extract loading is cleaned using a small amount of deionized water, and effective component is attracted in macroreticular resin.With 50% ethanol-eluting resin column collects the eluent of purifying, is dried in vacuo solution, obtains product.
Embodiment 2:
A kind of extraction separation method of tanshin polyphenolic acid B, its step are as follows:
(1) it chooses red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;
(2) it extracts: according to parts by weight, weighing red rooted salvia medicine materical crude slice 50g, 600 parts of water of pH5.0 are added, every gram of medicine is added The zytase of material 12U, stevioside 1g, 45 DEG C are reacted 3 hours, cooling, and filtered fluid is obtained by filtration;
Liquid is supplied, is 3.61% according to the recovery rate that tanshin polyphenolic acid B is calculated in standard curve.
(3) it purifies: 1/5th of the original volume of extracting solution vacuum concentration is purified using macroporous absorbent resin.
The step (3) are as follows:
95% ethyl alcohol impregnates resin 18 hours, is swollen it sufficiently, selects glass column, uses 95% alcohol flushing resin Column washes away the organic impurities in resin containing band.First deionization washing, 5% hydrochloric acid solution impregnate, and drain acid solution, then use deionization Water is cleaned, and 3% sodium hydroxide solution is added and washes, then deionization washing, removes water-solubility impurity in resin.Use 50% ethyl alcohol HCL solution rinses resin column.Extract loading is cleaned using a small amount of deionized water, and effective component is attracted in macroreticular resin.With 50% ethanol-eluting resin column collects the eluent of purifying, is dried in vacuo solution, obtains product.
Embodiment 3
A kind of extraction separation method of tanshin polyphenolic acid B, its step are as follows:
(1) it chooses red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;
(2) it extracts: according to parts by weight, weighing red rooted salvia medicine materical crude slice 50g, the water 600g of pH5.0 is added, every gram of medicinal material is added The zytase of 10U, rebaudioside 1g, stevioside 1g, 45 DEG C are reacted 2 hours, cooling, and filtered fluid is obtained by filtration;
Liquid is supplied, is 3.86% according to the recovery rate that tanshin polyphenolic acid B is calculated in standard curve.
(3) it purifies: 1/5th of the original volume of extracting solution vacuum concentration is purified using macroporous absorbent resin.
Preferably, the step (3) are as follows:
95% ethyl alcohol impregnates resin 18 hours, is swollen it sufficiently, selects glass column, uses 95% alcohol flushing resin Column washes away the organic impurities in resin containing band.First deionization washing, 5% hydrochloric acid solution impregnate, and drain acid solution, then use deionization Water is cleaned, and 3% sodium hydroxide solution is added and washes, then deionization washing, removes water-solubility impurity in resin.Use 50% ethyl alcohol HCL solution rinses resin column.Extract loading is cleaned using a small amount of deionized water, and effective component is attracted in macroreticular resin.With 50% ethanol-eluting resin column collects the eluent of purifying, is dried in vacuo solution, obtains product.
Embodiment 4
Investigation is added without the case where rebaudioside and stevioside:
Check experiment 1:
A kind of extraction separation method of tanshin polyphenolic acid B, its step are as follows:
(1) it chooses red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;
(2) it extracts: according to parts by weight, weighing 1 part of red rooted salvia medicine materical crude slice, 20 parts of water of pH5.0 are added, every gram of medicinal material is added 45 DEG C of zytase of 10U react 3 hours, cooling, and filtered fluid is obtained by filtration;
Liquid is supplied, is 2.36% according to the recovery rate that tanshin polyphenolic acid B is calculated in standard curve.
Check experiment 2:
A kind of extraction separation method of tanshin polyphenolic acid B, its step are as follows:
(1) it chooses red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;
(2) it extracts: according to parts by weight, weighing 1 part of red rooted salvia medicine materical crude slice, 20 parts of water of pH5.0 are added, every gram of medicinal material is added 45 DEG C of zytase of 10U react 8 hours, cooling, and filtered fluid is obtained by filtration;
Liquid is supplied, is 2.95% according to the recovery rate that tanshin polyphenolic acid B is calculated in standard curve, it is seen then that after extending the time The recovery rate of tanshin polyphenolic acid B improves, it was demonstrated that the present invention with rebaudioside and stevioside can effectively shorten enzymatic treatment when Between.
The detection of the final loss late of embodiment 5
Eluent vacuum drying, obtains brown ceramic powder, takes 0.1 gram of powder, be dissolved in 20 ml deionized waters, according to standard Curve test content.
Project Brown ceramic powder (g) Content of danshinolic acid B (%)
Embodiment 1 1.96 78.41
Embodiment 2 1.98 78.22
Embodiment 3 2.03 81.35
As it can be seen that integrated use zytase of the present invention, rebaudioside and stevioside can effectively shorten enzymatic treatment Time, and also can protect in purification process the activity of tanshin polyphenolic acid B, thus the pellet during increasing substantially extraction purification The stability of phenolic acid B.The two exclusive use has this effect, and combining more has synergy.The present invention is also directly from Radix Salviae Miltiorrhizae Pharmaceutical decocting piece sets out, and does not need to crush, and a step can be obtained the very high extracting solution of recovery rate.
It should be noted that the foregoing is merely preferred specific embodiment of the invention, if conception under this invention institute It changes, the function generated, it, should all be within the scope of the invention when the spirit still covered without departing from specification.
In the description of this specification, reference term " one embodiment ", " some embodiments ", " example ", " specifically show The description of example " or " some examples " etc. means specific features, structure, material or spy described in conjunction with this embodiment or example Point is included at least one embodiment or example of the invention.In the present specification, schematic expression of the above terms are not Centainly refer to identical embodiment or example.Moreover, particular features, structures, materials, or characteristics described can be any One or more embodiment or examples in can be combined in any suitable manner.
Although an embodiment of the present invention has been shown and described, it will be understood by those skilled in the art that: not A variety of change, modification, replacement and modification can be carried out to these embodiments in the case where being detached from the principle of the present invention and objective, this The range of invention is defined by the claims and their equivalents.

Claims (7)

1. a kind of extraction separation method of tanshin polyphenolic acid B, it is characterised in that:
Zytase, rebaudioside and/or stevioside are used.
2. the extraction separation method of tanshin polyphenolic acid B described in claim 1, its step are as follows:
(1) it chooses red rooted salvia: choosing the red rooted salvia medicine materical crude slice in accordance with States Pharmacopoeia specifications;
(2) it extracts: according to parts by weight, weighing 1 part of red rooted salvia medicine materical crude slice, 12 parts of water of pH5.0 are added, zytase, Lay is added Bao Di glucoside and/or stevioside, 38-45 DEG C reaction 2-3 hours, it is cooling, filtered fluid is obtained by filtration;
(3) it purifies: extracting solution being concentrated, is purified using macroporous absorbent resin.
3. the extraction separation method of tanshin polyphenolic acid B as claimed in claim 2, it is characterised in that:
The zytase of every gram of medicinal material 5-15U is added.
4. the extraction separation method of tanshin polyphenolic acid B described in claim 2 or 3, it is characterised in that:
0.02 part of rebaudioside and/or 0.02 part of stevioside.
5. the extraction separation method of the described in any item tanshin polyphenolic acid Bs of claim 2-4, it is characterised in that:
The step (3) are as follows: extracting solution is concentrated into 1/5th of original volume.
6. the extraction separation method of the described in any item tanshin polyphenolic acid Bs of claim 2-5, it is characterised in that:
The step (3) are as follows: ethyl alcohol impregnates resin, is swollen it sufficiently, and glass column is selected to wash using alcohol flushing resin column Remove the organic impurities in resin containing band;First deionization washing, hydrochloric acid solution impregnate, drain acid solution, then be washed with deionized water, add Enter sodium hydroxide solution to wash, then deionization washing, removes water-solubility impurity in resin;Resin is rinsed using the HCL solution of ethyl alcohol Column, extract loading are cleaned using a small amount of deionized water, and effective component is attracted in macroreticular resin;With 50% ethanol elution tree Rouge column collects the eluent of purifying, is dried in vacuo solution, obtains product.
7. the extraction separation method of the described in any item tanshin polyphenolic acid Bs of claim 2-6, it is characterised in that:
The step (3) are as follows: 95% ethyl alcohol impregnates resin 18-20 hours, is swollen it sufficiently, selects glass column, uses 95% Alcohol flushing resin column washes away the organic impurities in resin containing band;First deionization washing, 5% hydrochloric acid solution impregnate, and drain acid Liquid, then be washed with deionized water, 2-4% sodium hydroxide solution is added and washes, then deionization washing, removes water-soluble miscellaneous in resin Matter;Resin column is rinsed using the HCL solution of 50% ethyl alcohol.Extract loading is cleaned using a small amount of deionized water, and effective component is inhaled It is attached in macroreticular resin;With 50% ethanol-eluting resin column, the eluent of purifying is collected, solution is dried in vacuo, obtains product.
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Citations (4)

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Publication number Priority date Publication date Assignee Title
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CN101759673A (en) * 2009-10-22 2010-06-30 南京泽朗医药科技有限公司 Method for extracting salvianolic acid B from fresh salvia miltiorrhiza
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CN105541768A (en) * 2015-12-22 2016-05-04 贵州景峰注射剂有限公司 Lithospermic acid B extraction method

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1884558A (en) * 2006-05-30 2006-12-27 天津大学 Method for intensively extracting red-rooted salvia polyphenol acids using composite enzyme hydrolyzing red-rooted salvia
CN101759673A (en) * 2009-10-22 2010-06-30 南京泽朗医药科技有限公司 Method for extracting salvianolic acid B from fresh salvia miltiorrhiza
CN103172601A (en) * 2013-03-04 2013-06-26 西北大学 Method for separating and extracting salvianolic acid B
CN105541768A (en) * 2015-12-22 2016-05-04 贵州景峰注射剂有限公司 Lithospermic acid B extraction method

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