CN101810660A - Water-soluble silymarin and preparation method thereof - Google Patents
Water-soluble silymarin and preparation method thereof Download PDFInfo
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- CN101810660A CN101810660A CN200910264177A CN200910264177A CN101810660A CN 101810660 A CN101810660 A CN 101810660A CN 200910264177 A CN200910264177 A CN 200910264177A CN 200910264177 A CN200910264177 A CN 200910264177A CN 101810660 A CN101810660 A CN 101810660A
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Abstract
The invention discloses water-soluble silymarin, which is an inclusion compound that takes cyclodextrin as main molecules and silymarin as guest molecules; and the inclusion compound contains 12 to 20wt % of silybinin. The preparation method thereof comprises the following steps: silybum marianum seeds are squeezed into silybum marianum cakes; the silybum marianum cakes are added into alkali water ethanol solution and are heated to 75DEG C to 85DEG C, the constant temperature is kept for 1.5-2.5 hours, and silybum marianum extracting solution is prepared after 2-4 times of continuous extraction; the silybum marianum extracting solution is added with the cyclodextrin for inclusion, thus obtaining inclusion compound solution; flocculant is added, standing after being well stirred; after flocculate is filtered out, membrane separation process is carried out, thus obtaining water-soluble silymarin solution; and after the membrane separation process, the water-soluble silymarin solution is concentrated and dried, thus obtaining the dried product of the water-soluble silymarin. The water-soluble silymarin prepared by the method has the advantages of high solubility, good quality, good drug stability and high bioavailability.
Description
Technical field
The present invention relates to the extraction of active ingredient silymarin in the Compositae medicinal plants Herba Silybi mariani, relate in particular to water soluble silymarin and extract preparation method.
Background technology
Herba Silybi mariani is good hepatoprotective plant, contains Flavonoid substances in its seed--silymarin.Silymarin includes flavone compounds such as silibinin, Isosilybin, silidianin and Silychristin, its Main Ingredients and Appearance silibinin has effects such as antioxidant radical, anti peroxidation of lipid, protection liver plasma membrane, anti-hepatic fibrosis, thereby improve the detoxification ability of liver, the liver protecting; Simultaneously, silymarin also has significant curative effect for the some diseases of cardiovascular system such as hyperlipidemia etc.; The Yiganling tablet of selling on the market is exactly the single preparations of ephedrine of silymarin.
The preparation of silymarin at present all is to extract as solvent with acetone or ethyl acetate or normal hexane to make fat-soluble silymarin.There are many deficiencies in this fat-soluble silymarin on using: at first, fat-soluble silymarin has the defective of solvent high residue, the residual quantity of its acetone, ethyl acetate or hexane far surpasses the acetone of national standard or ethyl acetate and is no more than the residue criterion that 5000ppm, hexane are no more than 290ppm all more than 20000PPm; And acetone or ethyl acetate all belong to harmful, use hazardous chemicals, can produce the paralysis effect to people's nervous system, suck acetone steam and can cause symptoms such as headache, dim eyesight, vomiting, the ethyl acetate steam of high concentration then can cause liver, the nephremia, causes acute lung edema then; Normal hexane also has very strong narcoticness; Therefore existing Herba Silybi mariani prepares solvent all has great hazardness to human body.The second, fat-soluble silymarin is insoluble in water, and active ingredient should not be absorbed by the body, and makes to exist the effective ingredient dissolubility behind the preparation and bioavailability is low, the defective of medicine stability difference.The 3rd, because fat-soluble silymarin is insoluble in water, make capsule or tablet so mainly be used as, be difficult to make intravenous injection, also difficult use on the health care of food product.
Be insoluble in the deficiency of water at fat-soluble Herba Silybi mariani, the begin one's study preparation of silymarin that can be water-soluble of people.Chinese invention patent ZL200410041363.6 discloses a kind of preparation method of Herba Silybi mariani extract meglumine salt, it is that fat-soluble silymarin and the meglumine that will prepare by fat-soluble extracting method are dissolved in respectively in the organic solvents such as methanol, ethanol or isopropyl alcohol, again two solution are merged, stir, and generate the Herba Silybi mariani meglumine salt, after filtration, make finished product after the drying.Though the Herba Silybi mariani meglumine salt that makes by said method can strengthen its water solublity and dissolubility, thereby improve its bioavailability, but not only this method does not solve the dissolvent residual problem of fat-soluble silymarin, has also brought new organic solvent residue problems such as methanol again.Though and the Herba Silybi mariani meglumine salt acts on and silymarin is very much approaching, its Main Ingredients and Appearance and effect await further to study, and its pharmaceutically-active stability and effective degree still need further raising.Therefore, the water soluble silymarin product of directly producing, have essential meaning is not arranged as yet on the market.
Summary of the invention
Technical problem to be solved by this invention provides a kind of water soluble silymarin and preparation method thereof, its not only finished product noresidue, and dissolubility height, product are of fine quality; And medicine stability is good, the bioavailability height.
In order to solve the problems of the technologies described above, water soluble silymarin of the present invention is to be that host molecule, silymarin are the clathrate of enclosed molecule with the cyclodextrin; The silibinin that contains 12%～20% (weight) in this clathrate.
In order to make above-mentioned water soluble silymarin, preparation method of the present invention may further comprise the steps:
(a), press degrease and make the Herba Silybi mariani cake with after the roguing of Herba Silybi mariani seed;
(b) the Herba Silybi mariani cake that will press oil is packed in the extraction pot, adds the aqueous alkali alcoholic solution in extraction pot, and heating kept constant temperature 1.5～2.5 hours after 75 ℃～85 ℃, extract 2～4 times continuously and make the Herba Silybi mariani extracting solution; The weight ratio of Herba Silybi mariani cake and aqueous alkali alcoholic solution is 1: (7～9); This aqueous alkali ethanol is mixed by alcoholic solution and NaOH, and the concentration expressed in percentage by weight of its alcoholic solution is 25%～35%, and the weight ratio of NaOH and alcoholic solution is 1: (50～25);
(c) will send in the enclose jar through the Herba Silybi mariani extracting solution behind the aqueous alkali ethanol extraction, in the enclose jar, add cyclodextrin, the input weight ratio of silymarin extracting solution and cyclodextrin is 1: (0.035～0.04), stirred 1-2 hour, forming with the cyclodextrin is that host molecule, silymarin are the inclusion complex in solution of enclosed molecule;
(d) described inclusion complex in solution is fed through in the flocculation jar, and in the flocculation jar, adds flocculating agent, and leave standstill after stirring;
(e) flocculate in the above-mentioned inclusion complex in solution of elimination and after obtaining clathrate filtering solution carries out membrance separation to this clathrate filtering solution and handles, and makes water soluble silymarin solution.
The present invention compared with prior art has following significant advantage:
At first, the present invention is owing to adopt mechanical means to press the oils and fats that goes in the Herba Silybi mariani seed, and extraction process is a simple physical process, any dissolvent residual can not take place, thereby for the noresidue of finished product, product are of fine quality lays a good foundation.
The second, the present invention does not only have hazard residue because employing aqueous alkali ethanol extracts the silymarin in the Herba Silybi mariani cake, and harmless residue also is convenient to volatilization or filtering, and low as the solvent production cost with aqueous alkali ethanol, also helps improving the yield of active ingredient; Also owing to adopt 75 ℃～85 ℃ extraction temperature, this temperature is apparently higher than the temperature of conventional organic solvents, broken through the limitation that the conventional organic solvents boiling point is low, the extraction temperature is difficult to improve, the raising of extracting temperature not only helps the release fully of active ingredient, improve resource utilization, and accelerated the rate of release of active ingredient, make effective ingredient in the extracting solution reach capacity time of state shorten over half, thereby improved preparation production efficiency greatly; Also, help the leaching fully of effective ingredient in the material owing to adopt the big doubly aqueous alkali alcoholic solution of amount.
The 3rd, the present invention is that host molecule, silymarin are the clathrate of enclosed molecule owing to adopt cyclodextrin inclusion compound technology thereby formed with the cyclodextrin, has improved the drug solubility and the water solublity of silymarin greatly; The silymarin drug molecule is protected, and has increased the medicine stability of silymarin again; More, can regulate the rate of release of final drug effectively, improve the bioavailability of medicine owing to adopt cyclodextrin inclusion compound technology.
The 4th, the present invention has been owing to adopted the flocculation operation, removes large granular impurities such as albumen, fiber, starch and tannin in the inclusion complex in solution effectively by flocculation step; Owing to adopt filter membrane further elimination molecule of separating treatment technology and microbial impurities thereof, both improved the finished product purity and the quality of water soluble silymarin greatly again; Making silymarin make preparations such as intravenous injection again becomes possibility, thereby has expanded the application of silymarin.
The 5th, adopt preparation method of the present invention, simplified process flow greatly than traditional handicraft, not only reduce active ingredient loss and pollution that intermediate link causes, and avoided the long quality that causes of active ingredient heated time to descend.Adopt the present invention also to help improving and kept the silibinin composition in the silymarin to greatest extent, the raising of silibinin content has strengthened the effect of drugs and the quality of finished of silymarin again greatly.
The further embodiment of the present invention will the described water soluble silymarin solution after membrance separation is handled carries out concentrate drying and becomes the water soluble silymarin dry products.Described concentrate drying is to use earlier the scraper plate concentrator the described water soluble silymarin solution after handling through membrance separation is concentrated, be the membrane filtration of 0.15 μ m～0.25 μ m with membrane aperture again after, be spray dried to the water soluble silymarin dry products.
Adopt the scraper plate concentrator to concentrate and adopt spray drying, it is simply effective to have technology, result of use is good, the characteristics that quality of finished is excellent, and further adopt membrane filtration, further the granulometric impurity in the filtering water soluble silymarin makes the purity of water soluble silymarin finished product higher, and quality is more excellent.Highly purified water soluble silymarin dry products range of application is wider.
Description of drawings
Fig. 1 is the process chart of water soluble silymarin preparation method of the present invention.
The specific embodiment
The present invention is further detailed explanation below in conjunction with Fig. 1.
Embodiment 1
To press degrease and form the Herba Silybi mariani cake with screw oil expeller after the Herba Silybi mariani seed screening roguing earlier, Herba Silybi mariani oil be sold; The Herba Silybi mariani cake is round pie, and its cake external diameter is 110mm, and THICKNESS CONTROL is between 1.5mm ± 0.2mm; The Herba Silybi mariani cake is standby.
Herba Silybi mariani cake 500kg after press for extracting juice deoiled is encased in the extraction pot, and to drop into weight ratio to extraction pot be the aqueous alkali ethanol of 1: 8 4000kg; This aqueous alkali ethanol is thrown to alcoholic solution with solid-state NaOH and is mixed, and the weight percent concentration of alcoholic solution is 30%, contains 30% alcoholic solution 97kg and the NaOH of 3kg in promptly every 100kg aqueous alkali ethanol.The alcoholic acid PH=8.3 of this aqueous alkali.Aqueous alkali ethanol in the extraction pot and Herba Silybi mariani cake mixture are warmed to 80 ℃, and keep constant temperature after 2 hours, extract 3 times continuously, and make the Herba Silybi mariani extracting solution.
The Herba Silybi mariani extracting solution is delivered in the enclose jar, and with 1: the Herba Silybi mariani extracting solution of (0.035～0.04) and cyclodextrin weight ratio drop into HP-.Herba Silybi mariani extracting solution with 1000kg is an example, should drop into the HP-of 35-40kg to 1000kg Herba Silybi mariani extracting solution.Continuous stirring is 1.5 hours after the input HP-, is that host molecule, silymarin are the inclusion complex in solution of enclosed molecule until forming with the HP-.Certainly cyclodextrin not only comprises HP-, also comprises alpha-cyclodextrin, δ-cyclodextrin, gamma-cyclodextrin etc.
Inclusion complex in solution is delivered in the flocculation jar, in flocculation jar, drops into bentonite flocculating agent by the percentage by weight of inclusion complex in solution 1%.And temperature is controlled between 35 ℃～40 ℃, leave standstill 30min after; Again the above-mentioned inclusion complex in solution that has flocculate is sent into centrifugal separator and elimination flocculate wherein continuously, to obtain clathrate filtering solution, last is that the ultrafilter membrane separator-filter of 0.22 μ m carries out membrane filtration with above-mentioned clathrate filtering solution through membrane aperture again, with further elimination granulometric impurity and microbial impurities and make the water soluble silymarin preparation that reaches the injection standard wherein.
Silymarin content in the water soluble silymarin preparation that the present invention provides is not less than 45% (weight), and silibinin content is between 12%～20% (weight), and it is of fine quality to have product, the characteristics that bioavailability is high.
Embodiment 2
After Herba Silybi mariani seed screening roguing, with mechanical type oil extruder degrease, silybin oil is sold; Press the Herba Silybi mariani cake standby after preliminary the pulverizing.
Herba Silybi mariani cake after press for extracting juice deoiled is put in the extraction pot, and with the ratio of 1: 7 Herba Silybi mariani cake and the aqueous alkali ethanol weight ratio aqueous alkali ethanol of in extraction pot, packing into.Aqueous alkali ethanol is to be mixed by alcoholic solution and solid state N aOH, and the percentage by weight of its alcoholic solution is 25%, contains 25% alcoholic solution 96kg, NaOH4kg in every 100kg aqueous alkali ethanol, aqueous alkali ethanol PH=8.5.Aqueous alkali ethanol in the extraction pot and Herba Silybi mariani cake mixture are warmed to 85 ℃, and keep constant temperature after 1.5 hours, extract 2 times continuously, and make the Herba Silybi mariani extracting solution.
The Herba Silybi mariani extracting solution is delivered in the enclose jar, and drops into the inclusion agents beta-schardinger dextrin-.Herba Silybi mariani extracting solution with 1000kg is an example, drops into the beta-schardinger dextrin-of 35-40kg by every 1000kg Herba Silybi mariani extracting solution.Continuous stirring is 1 hour after the Herba Silybi mariani extracting solution drops into beta-schardinger dextrin-, is that host molecule, silymarin are the inclusion complex in solution of enclosed molecule until forming with the beta-schardinger dextrin-.
Inclusion complex in solution is delivered in the flocculation jar, in flocculation jar, drops into the poly-bran of shell by 0.8% percentage ratio of inclusion complex in solution weight.And temperature is controlled between 35 ℃～40 ℃, after leaving standstill 1 hour, again the above-mentioned inclusion complex in solution that has flocculate is sent into centrifugal separator elimination flocculate continuously, to make clathrate filtering solution, be that the ultrafilter membrane separating and filtering device of 0.20 μ m carries out membrane filtration and makes water soluble silymarin enclose solution again with above-mentioned clathrate filtering solution warp let-off membrane aperture.
Above-mentioned water soluble silymarin enclose filtering solution is sent in the scraper plate concentrator concentrates, being concentrated into density is 1.12g/cm
3Fluid extract, the ultrafilter membrane separating and filtering device that is 0.15 μ m with this fluid extract warp let-off fenestra carries out membrane filtration again, sends into after the membrane filtration again and is dried to powdery, water-soluble silymarin dry products in the spray dryer.Silymarin content in this dried finished product is not less than 45% (weight), and silibinin content is between 12%～20%.
Embodiment 3
After Herba Silybi mariani seed screening roguing, with mechanical type oil extruder degrease, silybin oil is sold; Press the Herba Silybi mariani cake standby after preliminary the pulverizing.
Herba Silybi mariani cake after press for extracting juice deoiled is put in the extraction pot, and with the ratio of 1: 9 Herba Silybi mariani cake and the aqueous alkali ethanol weight ratio aqueous alkali ethanol of in extraction pot, packing into.Aqueous alkali ethanol is to be mixed by alcoholic solution and solid state N aOH, and the percentage by weight of its alcoholic solution is 35%, contains 35% alcoholic solution 98k g, NaOH 2kg in every 100kg aqueous alkali ethanol, aqueous alkali ethanol PH=8.Aqueous alkali ethanol in the extraction pot and Herba Silybi mariani cake mixture are warmed to 75 ℃, and keep constant temperature after 2.5 hours, extract continuously 4 times and make the Herba Silybi mariani extracting solution.
The Herba Silybi mariani extracting solution is delivered in the enclose jar, and drops into the inclusion agents alpha-cyclodextrin.Herba Silybi mariani extracting solution with 1000kg is an example, drops into the alpha-cyclodextrin of 35-40kg by every 1000kg Herba Silybi mariani extracting solution.Continuous stirring is 2 hours after the Herba Silybi mariani extracting solution drops into alpha-cyclodextrin, is that host molecule, silymarin are the inclusion complex in solution of enclosed molecule until forming with the cyclodextrin.
Inclusion complex in solution is delivered in the flocculation jar, in flocculation jar, drops into the ZC-101 high polymer coagulant by 0.8% percentage ratio of inclusion complex in solution weight.And temperature is controlled between 35 ℃～40 ℃, and after leaving standstill 45min, the above-mentioned inclusion complex in solution that has flocculate is sent into centrifugal separator and the elimination flocculate continuously, to make clathrate filtering solution, be that the ultrafilter membrane separating and filtering device of 0.50 μ m carries out membrane filtration and makes water soluble silymarin enclose solution with above-mentioned clathrate filtering solution through membrane aperture again.
Above-mentioned water soluble silymarin enclose solution is sent in the scraper plate concentrator concentrates, being condensed into density is 1.12g/cm
3Fluid extract, the ultrafilter membrane separating and filtering device that is 0.20 μ m with this fluid extract warp let-off fenestra carries out membrane filtration again, sends into after the membrane filtration again and is dried to powdery, water-soluble silymarin dry products in the spray dryer.Silymarin content in this dried finished product is not less than 45% (weight), and silibinin content is between 12%～20%.
Claims (10)
1. a water soluble silymarin is characterized in that this water soluble silymarin is is that host molecule, silymarin are the clathrate of enclosed molecule with the cyclodextrin; The silibinin that contains 12%～20% (weight) in this clathrate.
2. water soluble silymarin according to claim 1 is characterized in that described cyclodextrin is beta-schardinger dextrin-or HP-.
3. method for preparing the described water soluble silymarin of claim 1 is characterized in that this preparation method may further comprise the steps:
(a), press degrease and make the Herba Silybi mariani cake with after the roguing of Herba Silybi mariani seed;
(b) the Herba Silybi mariani cake that will press oil is packed in the extraction pot, adds the aqueous alkali alcoholic solution in extraction pot, and heating kept constant temperature 1.5～2.5 hours after 75 ℃～85 ℃, extract 2～4 times continuously and make the Herba Silybi mariani extracting solution; The weight ratio of Herba Silybi mariani cake and aqueous alkali alcoholic solution is 1: (7～9); This aqueous alkali ethanol is mixed by alcoholic solution and NaOH, and the concentration expressed in percentage by weight of its alcoholic solution is 25%～35%, and the weight ratio of NaOH and alcoholic solution is 1: (50～25);
(c) will send in the enclose jar through the Herba Silybi mariani extracting solution behind the aqueous alkali ethanol extraction, in the enclose jar, add cyclodextrin, the input weight ratio of silymarin extracting solution and cyclodextrin is 1: (0.035～0.04), stirred 1-2 hour, forming with the cyclodextrin is that host molecule, silymarin are the inclusion complex in solution of enclosed molecule;
(d) described inclusion complex in solution is fed through in the flocculation jar, and in the flocculation jar, adds flocculating agent, and leave standstill after stirring;
(e) flocculate in the above-mentioned inclusion complex in solution of elimination and after obtaining clathrate filtering solution carries out membrance separation to this clathrate filtering solution and handles, and makes water soluble silymarin solution.
4. water soluble silymarin preparation method according to claim 3 is characterized in that the described water soluble silymarin solution after handling through membrance separation is carried out concentrate drying becomes the water soluble silymarin dry products.
5. water soluble silymarin preparation method according to claim 4, it is characterized in that, described concentrate drying is to use the scraper plate concentrator earlier the described water soluble silymarin solution after handling through membrance separation is concentrated, after being the membrane filtration of 0.15 μ m～0.5 μ m with membrane aperture again, be spray dried to the water soluble silymarin dry products.
6. according to claim 3,4 or 5 described water soluble silymarin preparation methoies, it is characterized in that described Herba Silybi mariani cake overall dimensions is 90～110mm, the thickness of this Herba Silybi mariani cake is 1.3mm～1.7mm.
7. according to claim 3,4 or 5 described water soluble silymarin preparation methoies, it is characterized in that, the weight ratio of described Herba Silybi mariani cake and aqueous alkali alcoholic solution is 1: 8, the concentration expressed in percentage by weight of alcoholic solution is 30%, heating to 80 ℃ keeps constant temperature after 2 hours, extracts 3 times continuously and makes the Herba Silybi mariani extracting solution; The PH=8 of aqueous alkali alcoholic solution～8.5.
8. according to claim 3,4 or 5 described water soluble silymarin preparation methoies, it is characterized in that described cyclodextrin is beta-schardinger dextrin-or HP-.
9. according to claim 3,4 or 5 described water soluble silymarin preparation methoies, it is characterized in that described flocculating agent is a bentonite, this bentonitic input amount is 0.8%～1.2% of an inclusion complex in solution weight, leaves standstill after stirring 0.5～1 hour.
10. according to claim 3,4 or 5 described water soluble silymarin preparation methoies, it is characterized in that, utilize the flocculate in the described inclusion complex in solution of centrifugal separator elimination, and after obtaining clathrate filtering solution, filter membrane with membrane aperture 0.15 μ m～0.30 μ m carries out the membrance separation processing to clathrate filtering solution again, and obtains water soluble silymarin solution.
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| CN104904895A (en) * | 2014-03-11 | 2015-09-16 | 范永明 | Water-soluble silymarin health tea |
| CN106667998A (en) * | 2017-02-13 | 2017-05-17 | 内蒙古昶辉生物科技股份有限公司 | Method for preparing water-soluble silymarin |
| CN107087480A (en) * | 2016-02-18 | 2017-08-25 | 四川利君精华制药股份有限公司 | A kind of medicinal milk thistle cultivation technique and silymarin extracting method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104904895A (en) * | 2014-03-11 | 2015-09-16 | 范永明 | Water-soluble silymarin health tea |
| US10702568B2 (en) | 2015-03-19 | 2020-07-07 | Cydex Pharmaceuticals, Inc. | Compositions containing silymarin and sulfoalkyl ether cyclodextrin and methods of using the same |
| US11382944B2 (en) | 2015-03-19 | 2022-07-12 | Cydex Pharmaceuticals, Inc. | Compositions containing silymarin and sulfoalkyl ether cyclodextrin and methods of using the same |
| CN107087480A (en) * | 2016-02-18 | 2017-08-25 | 四川利君精华制药股份有限公司 | A kind of medicinal milk thistle cultivation technique and silymarin extracting method |
| CN106667998A (en) * | 2017-02-13 | 2017-05-17 | 内蒙古昶辉生物科技股份有限公司 | Method for preparing water-soluble silymarin |
| CN106667998B (en) * | 2017-02-13 | 2019-03-12 | 内蒙古昶辉生物科技股份有限公司 | A kind of preparation method of water-soluble silymarin |
| CN108524364A (en) * | 2018-06-14 | 2018-09-14 | 上海棠美生物科技有限公司 | A kind of cosmetic active object nano-carrier package and preparation method thereof |
| CN110204426A (en) * | 2019-07-02 | 2019-09-06 | 黑龙江康源生物科技有限公司 | A kind of preparation method and water solubility CBD of water solubility CBD |
| CN110204426B (en) * | 2019-07-02 | 2023-05-30 | 梁志全 | Preparation method of water-soluble CBD and water-soluble CBD |
| CN111494564A (en) * | 2020-04-30 | 2020-08-07 | 江苏中兴药业有限公司 | Preparation method of compound liver-protecting and alcohol-dispelling tablet |
| CN111494564B (en) * | 2020-04-30 | 2021-07-27 | 江苏中兴药业有限公司 | Preparation method of compound liver-protecting and alcohol-dispelling tablet |
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