CN102372750A - Method for simultaneously preparing albiflorin and paeoniflorin - Google Patents
Method for simultaneously preparing albiflorin and paeoniflorin Download PDFInfo
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Abstract
The present invention discloses a purification method for simultaneously preparing albiflorin and paeoniflorin. The method comprises: adopting a paeonia lactiflora medicinal material or a paeonia lactiflora extract as a raw material; adopting a column chromatography method to purify the paeoniflorin and the albiflorin. According to the present invention, the method of the present invention has characteristics of simple purification process, easy operation, high purification efficiency and short purification time; the high purity albiflorin and the high purity paeoniflorin can be prepared in the same process with low cost and low energy consumption, such that the purpose of environmental protection is achieved, economic benefits are improved.
Description
Technical field
The invention belongs to medical technical field, relate to the separating and extracting method of chemical field compound, be specifically related to the preparation technology of natural plant physiologically active substance peoniflorin and lactone glucoside of Radix Paeoniae.
Background technology
Chinese herbaceous peony is a Ranunculaceae Chinese herbaceous peony subfamily Paeonia per nnial herb, and its dry root commonly used is used as medicine.Chinese Pharmacopoeia was included 2 kinds of Chinese herbaceous peonies in 2010 in the version.A kind of is the root of herbaceous peony (Radix Paeoniae Alba), is the dry root of ranunculaceae plant Chinese herbaceous peony Paeonia lactiflora Pall.; A kind of is the radix paeoniae rubrathe (Radix Paeoniae Rubra), is the dry root of ranunculaceae plant river radix paeoniae rubrathe Paeonia veitchii Lynch.The existing in the market multiple Chinese medicine preparation that contains Chinese herbaceous peony is like NAOXUESHUAN PIAN, beneficial brain rehabilitation capsule, hemiparalysis restoration sheet, pills for resuscitation and reconstruction, DAHUOLUO WAN etc.Be mainly used in diseases such as treatment cardiovascular and cerebrovascular diseases, neurodynia, hypertension, miscarriage, dysmenorrhoea.Modern chemistry research shows: Chinese herbaceous peony mainly contains compositions such as peoniflorin, lactone glucoside of Radix Paeoniae, Hydroxy peoniflorin, benzoylpaeoniflorin.Because peoniflorin content in medicinal material is high, pure article are prone to obtain, so more to the research report of peoniflorin.For a long time, great majority research thinks that peoniflorin is the main effective constituent of Chinese herbaceous peony, thereby measurement contains the Chinese herbaceous peony medicine as index with peoniflorin, and estimates the capability and performance of medicine with the height of its content.
In recent years, modern pharmacological research finds that lactone glucoside of Radix Paeoniae has analgesia, calmness, anticonvulsant action, to immune effect, to the effect of unstriated muscle; Anti-inflammatory action, resisting pathogenic microbes, liver protection effect is mainly used in epilepsy clinically; Analgesia, drug rehabilitation, only dizzy, treatment rheumatoid arthritis, treatment bacillary dysentery and enteritis; The treatment viral hepatitis, geriatric disease, flocculation of sulfuric-resisting barium and mucolytics effect.
Therefore; Pharmacological research to lactone glucoside of Radix Paeoniae more and more comes into one's own; The research of lactone glucoside of Radix Paeoniae is increasing; For example: application number is that 200510045840.0 application for a patent for invention discloses a kind of compsn that contains active compound peoniflorin (paeoniflorin) and lactone glucoside of Radix Paeoniae (albiflorin) that extraction separation obtains from the root of herbaceous peony (Ranunculaceae Paeonia plant peony Paeonia lactifora Pall); Two component concentration sums are between 50%-95%; And peoniflorin and the lactone glucoside of Radix Paeoniae ratio in said composition is 1: 10～10: 1, and said composition is used to prepare the medicine of the illness of oligoleukocythemia, thrombocyte and the reduction of blood red sphaeroprotein of treating a variety of causes and causing.And for example: application number is that 200710132810.2 application for a patent for invention discloses a kind of peoniflorin and lactone glucoside of Radix Paeoniae pharmaceutical composition of containing; Peoniflorin is 10 with the ratio of the weight of lactone glucoside of Radix Paeoniae in the said composition: 1-50: 1, and this bright pharmaceutical composition can be used for prevention and treatment cardiovascular and cerebrovascular diseases.But above-mentioned research only is that the pharmacological use of peoniflorin, lactone glucoside of Radix Paeoniae is studied, preparation be the compsn of peoniflorin and lactone glucoside of Radix Paeoniae.
Because the chemical property of lactone glucoside of Radix Paeoniae, the method difficulty of the lactone glucoside of Radix Paeoniae that preparation purity is high does not also have a kind of easy feasible technological in the existing research, can be low-cost, mass preparation obtains highly purified lactone glucoside of Radix Paeoniae.For example application number is the method that 200910100680.3 application for a patent for invention discloses a kind of separating and preparing peony lactone glucoside by simulation moving bed chromatography.This method separating and preparing peony lactone glucoside by simulation moving bed chromatography adopts the Radix Paeoniae Alba total glucosides extract as raw material, application simulation moving-bed chromatographic separating and preparing peony lactone glucoside; The stationary phase of SMBC adopts C18 silica gel; Moving phase adopts the mixing solutions of methyl alcohol or acetonitrile and water, formic acid, Virahol, and percentage meter by volume in the mixing solutions: methyl alcohol or acetonitrile 10%～50%, water 50%～90%, formic acid 0～1%, Virahol 0～2%, the summation of each above-mentioned component are 100%; Though the purity of the lactone glucoside of Radix Paeoniae of this method preparation can reach more than 90%; But because this Technology Need uses a large amount of expensive reverse phase silica gels (RP-C18), and preparation technology's flow process is complicated, and operating procedure control condition is harsh; Cause product cost high, be not suitable for scale operation.
Up to now, not having a kind of suitable industrialization to produce the operational path for preparing high purity lactone glucoside of Radix Paeoniae and high purity peoniflorin simultaneously as yet discloses.
Summary of the invention
The object of the present invention is to provide a kind of method for preparing high purity peoniflorin and lactone glucoside of Radix Paeoniae simultaneously, the inventive method operating procedure process is simple, and is with short production cycle.Utilization the inventive method can prepare the peoniflorin and the lactone glucoside of Radix Paeoniae of feather weight respectively in a technical process, and resulting peoniflorin and lactone glucoside of Radix Paeoniae purity can reach more than 90%.Take this preparation method to extract purifying peoniflorin and lactone glucoside of Radix Paeoniae, reduced production cost significantly, suitable batch preparation and suitability for industrialized production.
Be to realize the object of the invention, the present invention provides a kind of method for preparing peoniflorin and lactone glucoside of Radix Paeoniae simultaneously, comprise with column chromatography method to Chinese herbaceous peony medicinal material or Radix Paeoniae Alba extract separate, purifying.
Wherein, column chromatography is selected macroporous resin column chromatography and silica gel column chromatography.
When adopting the Chinese herbaceous peony medicinal material to extract as raw material, extraction solution selection water, mass percent concentration are that ethanol or the mass percent concentration of 20-70% is the methyl alcohol of 20-70%, preferably use water extraction.Process for extracting can adopt reflux extraction or diacolation extraction method to carry out described extraction and handle.When adopting reflux extraction to extract, each refluxing extraction process Chinese medicinal materials weight is 1 with the ratio of the volume that extracts solvent: 5-8, extraction time 2-3h/ time.
For avoiding liquid concentrator after the medicinal material extract when the macroporous adsorptive resins,, and cause resin column to stop up because of overrich or muddiness.Can take following two kinds of pretreatment processs: (1) medicinal material liquid concentrator by the alcohol precipitation impurity-removing method of routine, adds an amount of high concentration ethanol (95% ethanol or absolute ethyl alcohol); Make the ethanol final concentration reach 70-75%; After leaving standstill, get supernatant, reclaim under reduced pressure; Remove ethanol, reclaim liquid again through macroporous adsorptive resins.(2) medicinal material liquid concentrator adds 2-4 times of water gaging, and hold over night is got supernatant, again through macroporous adsorptive resins.
The resin model that macroporous resin column chromatography is selected for use can be the macroporous resin of nonpolar, low-pole, middle polarity, like D101, AB-8, DM130H, XAD-2, D201, HP-20, X-5, H103, DM11 or ADS-17 type resin.Be preferably nonpolar macroporous adsorption resin, like AB-8, D101 type resin.
In the macroporous resin column chromatography process, the column diameter of macroporous resin column is 1 with the ratio of post height: 10-50.The column volume of macroporous resin is 8-25 with the ratio of Chinese herbaceous peony medicinal material weight: 10, and promptly working as Chinese herbaceous peony medicinal material weight is 100g, then the column volume of macroporous resin column is 80-250ml; When Chinese herbaceous peony medicinal material weight is 100kg, then the column volume of macroporous resin column is 80-250L.
The macroporous resin column chromatography eluent can be aqueous ethanol, aqueous methanol or the aqueous acetone of different concns.Behind end of the sample, the water washing of doubly measuring column volume with 3-6 is earlier removed the non-adsorbable impurity of resin (comprising polysaccharide etc.), and then is used eluent wash-out, elution process can adopt single concentration wash-out, or adopts gradient elution.For avoiding resin column in elution process, meet water because of the high density eluent and can produce bubble, influence the resin column elute effect; Preferentially use 1-2 column volume of eluent wash-out of low concentration, re-use the eluent wash-out of higher concentration.
Also can adopt high concentration methanol or high concentration ethanol that medicinal material is carried out heating and extracting; Sugar is less in the extracting solution that obtains; Can be without the macroporous adsorbent resin column chromatography step, and directly carry out 1-3 time silica gel column chromatography, peoniflorin that obtains conforming to quality requirements and lactone glucoside of Radix Paeoniae.
The silica gel granularity that silica gel column chromatography uses also has considerable influence to separating effect, and in theory, the silica gel that granularity is thin more, separating effect are good more, but post is pressed obviously rising, and to the also corresponding increase of the requirement of equipment, and the cost of silica gel also can significantly increase.Preferred size of the present invention is a 100-200 order silica gel.
The eluting solvent of silica gel column chromatography is selected ETHYLE ACETATE and methanol mixture, and wherein methyl alcohol is 0-15 with the ratio of the volume of ETHYLE ACETATE: 100.Also can select ETHYLE ACETATE and alcoholic acid mixture, wherein ethanol is 0-10 with the ratio of the volume of ETHYLE ACETATE: 100.Or the mixture of selection ETHYLE ACETATE and acetone, wherein acetone is 0-20 with the ratio of the volume of ETHYLE ACETATE: 100.Or the mixture of selection ETHYLE ACETATE and water, wherein water is 0-3.5 with the ratio of the volume of ETHYLE ACETATE: 100.
The silica gel that silica gel column chromatography uses is 5-50 with the ratio of the weight of sample to be purified: 1.When the weight part of silica gel and sample to be purified relatively lower, can influence the separating effect of target product, the product gas purity that promptly obtains has decline.Improve the ratio of silica gel and the weight part of sample to be purified, can improve target product, especially the separating effect between peoniflorin and the lactone glucoside of Radix Paeoniae.But cost (the silica gel usage quantity that comprises column chromatography, eluting solvent consumption) all can correspondingly increase.The preferred silica gel of the present invention is 8-20 with the ratio of the weight of sample to be purified: 1.For further improving the purity of peoniflorin or lactone glucoside of Radix Paeoniae, can pass through the silica gel column chromatography step again 1-2 time to product, the product purity that obtains can reach more than 98.0%, but production cost also can correspondingly increase.
The present invention prepares peoniflorin and the used raw material of lactone glucoside of Radix Paeoniae and comprises from plant, particularly medicinal plant Chinese herbaceous peony and the river radix paeoniae rubrathe, separating to purify and obtain; Selected raw material can be arbitrary position or whole plant such as these medicinal material rhizome, root, leaf, branch, stem, fruit, flower, and wherein preferred position is root and rhizome.Extraction solvent described in the preparation technology can be water or any alcohols commonly used, ketone and esters solvent or the mixed solvent that is made into by a certain percentage by these solvents; Or by these solvents and acidity or basic solvent sour, that alkali is made into; Because peoniflorin and lactone glucoside of Radix Paeoniae are water soluble component; Taking all factors into consideration extraction cost, be preferably water, is aqueous methanol or aqueous ethanol secondly.
The raw material that the present invention prepares peoniflorin and lactone glucoside of Radix Paeoniae use also can directly adopt Radix Paeoniae Alba extract.Related Radix Paeoniae Alba extract comprises that (1) directly obtains through concentrating after the conventional solvent extraction with the Chinese herbaceous peony medicinal material; (2) the Chinese herbaceous peony medicinal material adopts conventional solvent extraction method again through after the solvent extraction, obtains after concentrating; (3) the Chinese herbaceous peony medicinal material passes through absorption with macroporous adsorbent resin, wash-out again through solvent extraction, obtains after concentrating.When using directly when concentrating the Radix Paeoniae Alba extract that obtains as raw material with the Chinese herbaceous peony medicinal material extract, through macroporous resin column chromatography, pass through silica gel column chromatography again after then can raw material directly being dissolved, obtain peoniflorin and lactone glucoside of Radix Paeoniae.The Radix Paeoniae Alba extract that obtains after after using the solvent extraction of Chinese herbaceous peony medicinal material process, adopting conventional solvent extraction method to concentrate again is as raw material; Or when using Radix Paeoniae Alba extract (like Radix Paeoniae Alba total glycosides) after handling as raw material through macroporous resin column; Then can not need to pass through again macroporous adsorptive resins, directly with material dissolution, behind the silica gel mixed sample; Through 1-3 silica gel column chromatography, obtain peoniflorin and lactone glucoside of Radix Paeoniae respectively again.The peoniflorin that obtains and the purity of lactone glucoside of Radix Paeoniae all can reach 50-99.9%.
The present invention has following advantage:
1, uses the inventive method, can in same technical process, prepare peoniflorin and lactone glucoside of Radix Paeoniae, make full use of the comprehensive use value of herb resource.
2, use the inventive method, can in same technical process, obtain the peoniflorin of feather weight and the lactone glucoside of Radix Paeoniae of feather weight respectively.
3, use the inventive method, peoniflorin that obtains and lactone glucoside of Radix Paeoniae purity are high, and peoniflorin and lactone glucoside of Radix Paeoniae content reach 50-99.9%.
4, preparation technology's method of the present invention is simple, and purification efficiency is high, and it is low to consume energy, environmental protection, and the operating procedure condition is controlled easily, and quality controllability is strong.
5, high purity peoniflorin of the present invention and lactone glucoside of Radix Paeoniae; Can be used to prepare medicine and functional health-care food separately; Also can with other any Chinese and western drugs or food; Especially with some have the Chinese medicine that activates blood circulation and disperses blood clots and protect cardiovascular and cerebrovascular diseases or with tranquillizing and allaying excitement and antidepressant drug matching antianxity, play the purpose of collaborative or synergy, be used to prepare medicine and functional health-care food.
Description of drawings:
Accompanying drawing 1 is that the HPLC of embodiment 1 preparation gained peoniflorin detects collection of illustrative plates
Accompanying drawing 2 is that the HPLC of embodiment 1 preparation gained lactone glucoside of Radix Paeoniae detects collection of illustrative plates
Accompanying drawing 3 is that the HPLC of embodiment 2 preparation gained peoniflorins detects collection of illustrative plates
Accompanying drawing 4 is that the HPLC of embodiment 2 preparation gained lactone glucoside of Radix Paeoniae detects collection of illustrative plates
Accompanying drawing 5 is that the HPLC of embodiment 7 preparation gained lactone glucoside of Radix Paeoniae detects collection of illustrative plates
Embodiment
Through embodiment the present invention is further specified below.
1, the extraction of medicinal material
150 kilograms of exsiccant Chinese herbaceous peony roots, be ground into meal after, in the 2 tons of stainless steel traditional Chinese medicine extraction jars of packing into; The adding mass percent concentration is 70% ethanolic soln; Heating and refluxing extraction three times, the volume that extracts the ethanolic soln of usefulness is followed successively by 1200L, 900L; 900L, extraction time is followed successively by 3h, 2.5h, 2h.
After No. three extracting solutions merging; Adopt vacuum decompressioning and concentrating tank (Wuxi City China new drug equipment ltd produces) to carry out concentrating under reduced pressure, being concentrated into does not have the alcohol flavor, makes the Chinese herbaceous peony liquid concentrator; Wherein the temperature of concentrating under reduced pressure is 70 ℃; The relative vacuum degree is-0.09～-0.075MPa, the specific density of Chinese herbaceous peony liquid concentrator is 1.25, volume is 220L.
2, separating treatment
1) add 95% ethanol 700L to the Chinese herbaceous peony liquid concentrator, hold over night is got supernatant, is concentrated into 200L, adds the dilution of 400L water.Carry out separating treatment through macroporous adsorptive resins.Wherein, macroporous adsorbent resin is selected AB-8 type macroporous adsorbent resin, and the column volume of macroporous adsorptive resins is 200L (0.4 meter of a column diameter; Post is high 1.6 meters), behind the end of the sample, earlier with 500L water washing to effluent as clear as crystal after; Using the 1000L mass percent concentration again is 60% methanol solution wash-out; Collect elutriant, elution flow rate is 150L/h, and every 50L elutriant is collected as first-class part;
That 2) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant of collecting contains that there is something special, will contain peoniflorin and merge to eluent stream part of lactone glucoside of Radix Paeoniae, obtains the resin column elutriant.Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol, and the volume ratio of chloroform and methyl alcohol is 4: 1, behind the ascending development, sprays the ethanol solution of sulfuric acid with 5%, 150 ℃ of heating colour developings after 5 minutes;
The resin column elutriant that 3) will contain peoniflorin and lactone glucoside of Radix Paeoniae component places in the vacuum decompressioning and concentrating tank (Wuxi City China new drug equipment ltd produces) and carries out concentrating under reduced pressure; Concentrate back water bath method, pulverizing; Obtain 7.5 kilograms of the crude mixture of peoniflorin and lactone glucoside of Radix Paeoniae; Wherein, the temperature of concentrating under reduced pressure is 70 ℃, the relative vacuum degree is-0.095～-0.08Mpa;
3, purification process
1) crude mixture of peoniflorin and lactone glucoside of Radix Paeoniae is all dissolved the back with 20L methyl alcohol and add 8.9 kilograms of silica-gel powders (100-200 order), stir, drying obtains blend sample;
2) blend sample being carried out silica gel column chromatography, is that eluent carries out wash-out with ETHYLE ACETATE and methanol mixture, and wherein, the granularity of the sorbent material silica gel in the silicagel column is the 100-200 order, and the column diameter of silicagel column is 1: 8 with the ratio of post height; Sorbent material silica gel is 6: 1 with the ratio of the weight of blend sample, and eluent is the mixed solvent (volume ratio is 20: 1) of ETHYLE ACETATE and methyl alcohol, eluent consumption 4000L, and elution flow rate is 200L/h, every 50L elutriant is collected first-class part;
That 3) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant contains that there is something special, and elutriant is merged into three parts: contain peoniflorin part, peoniflorin and lactone glucoside of Radix Paeoniae mixing portion, contain the lactone glucoside of Radix Paeoniae part, distinguish evaporate to dryness; Get 1.74 kilograms of peoniflorins, peoniflorin and 0.37 kilogram in lactone glucoside of Radix Paeoniae mixture, 0.86 kilogram of lactone glucoside of Radix Paeoniae; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%.
Detecting paeoniflorin content through HPLC is 88.26%, sees accompanying drawing 1; Lactone glucoside of Radix Paeoniae content is 92.23%, sees accompanying drawing 2.
The HPLC testing conditions is: instrument: Water 515 pumps, 2487 detectors; Chromatographic column: KromasilRP-C18; Moving phase: acetonitrile: 0.1% phosphate aqueous solution (13: 87); Detect wavelength: 230nm; Flow velocity: 1.0ml/min.
1, the extraction of medicinal material
300 kilograms of fresh paenoiae alba roots, after the chopping, in the 3 tons of traditional Chinese medicine extraction jars of packing into, the adding mass percent concentration is 40% ethanol; Heating and refluxing extraction three times, the alcoholic acid volume that extracts usefulness is followed successively by 2200L, 1800L, 1800L; Extraction time is followed successively by 3h, 3h, 2h;
After No. three extracting solutions merging, adopt vacuum decompressioning and concentrating tank to carry out concentrating under reduced pressure, being concentrated into does not have the alcohol flavor; Make the Chinese herbaceous peony liquid concentrator, wherein the temperature of concentrating under reduced pressure is 60 ℃, the relative vacuum degree is-0.09～-0.08MPa; The specific density of Chinese herbaceous peony liquid concentrator is 1.21, and volume is 250L.
2, separating treatment
1) add 95% ethanol 800L to the Chinese herbaceous peony liquid concentrator, hold over night is got supernatant, is concentrated into 250L, adds the dilution of 500L water.Adopt macroporous adsorptive resins to carry out separating treatment, wherein, macroporous adsorbent resin is selected D-101 type macroporous adsorbent resin; The column volume of macroporous adsorptive resins is 225L (0.4 meter of a diameter, high 2.0 meters), behind the end of the sample; Earlier with 700L water washing to effluent as clear as crystal after, the 1200L mass percent concentration is 50% ethanolic soln wash-out again, the collection elutriant; Elution flow rate is 200L/h, and every 50L elutriant is collected as first-class part;
That 2) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant of collecting contains that there is something special, and the eluent stream part that will contain peoniflorin or lactone glucoside of Radix Paeoniae (or both mixing) merges to together, obtains the resin column elutriant; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%;
The resin column elutriant that 3) will contain peoniflorin and lactone glucoside of Radix Paeoniae component places in the vacuum decompressioning and concentrating tank (Wuxi City China new drug equipment ltd produces) and carries out concentrating under reduced pressure; Concentrate back water bath method, pulverizing; Obtain 8.1 kilograms of the crude mixture of peoniflorin and lactone glucoside of Radix Paeoniae; Wherein, the temperature of concentrating under reduced pressure is 70 ℃, the relative vacuum degree is-0.09～-0.075MPa;
3, purification process
1) crude mixture with peoniflorin and lactone glucoside of Radix Paeoniae all adds 10 kilograms of silica gel for chromatography powder (200-300 order) in the dissolving back with 15L ETHYLE ACETATE and methyl alcohol mixed liquor (wherein ETHYLE ACETATE, methyl alcohol volume ratio are 4: 1); Stir; Drying obtains blend sample;
2) blend sample being carried out silica gel column chromatography, is eluent with ETHYLE ACETATE and alcohol mixed solvent, carries out gradient elution, and wherein, the granularity of the sorbent material silica gel in the silicagel column is the 100-200 order, and the column diameter of silicagel column is 1: 8 with the ratio of post height; Sorbent material silica gel is 12: 1 with the ratio of the weight of lactone glucoside of Radix Paeoniae bullion, and ETHYLE ACETATE and alcoholic acid volume ratio are 10: 1 in the eluent, eluent consumption 6000L, and elution flow rate is 200L/h per hour, every 50L elutriant is collected as first-class part;
That 3) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant contains that there is something special, and elutriant is merged into two parts: contain peoniflorin part, contain lactone glucoside of Radix Paeoniae part (both cross sections are incorporated the peoniflorin part into), distinguish evaporate to dryness; Get 2.42 kilograms of peoniflorins, 1.16 kilograms of lactone glucoside of Radix Paeoniae; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%.
Detecting paeoniflorin content through HPLC is 84.78%, sees accompanying drawing 3; Lactone glucoside of Radix Paeoniae content is 94.71%, sees accompanying drawing 4.
The HPLC testing conditions is: instrument: Water 515 pumps, 2487 detectors; Chromatographic column: KromasilRP-C18; Moving phase: acetonitrile: 0.1% phosphate aqueous solution (13: 87); Detect wavelength: 230nm; Flow velocity: 1.0ml/min.
1, the extraction of medicinal material
100 kilograms of exsiccant Chinese herbaceous peony roots, be ground into meal after, soak 5 hours with the 400L deionized water after, pack in 1 ton of stainless steel diacolation jar, use the deionized water diacolation, the about 1500L of collection percolate.
2, separating treatment
1) adopt macroporous adsorptive resins to carry out separating treatment percolate.Wherein, macroporous adsorbent resin is selected AB-8 type macroporous adsorbent resin, and the column volume of macroporous adsorptive resins is 150L; Behind the end of the sample; Earlier with 500L water washing to effluent as clear as crystal after, using the 800L mass percent concentration again is 50% ethanol elution, elution flow rate is 100L/h; Collect elutriant, every 50L elutriant is collected as first-class part;
That 2) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant of collecting contains that there is something special, and the eluent stream part that will contain peoniflorin or lactone glucoside of Radix Paeoniae (or both mixing) merges to together, obtains the resin column elutriant; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%;
The resin column elutriant that 3) will contain peoniflorin and lactone glucoside of Radix Paeoniae component places and carries out concentrating under reduced pressure in the vacuum decompressioning and concentrating tank; Concentrate back water bath method, pulverizing; Obtain 4.81 kilograms of the crude mixture of peoniflorin and lactone glucoside of Radix Paeoniae; Wherein, the temperature of concentrating under reduced pressure is 70 ℃, the relative vacuum degree is-0.09～-0.075MPa;
3, purification process
1) crude mixture is all dissolved the back with an amount of methyl alcohol and add 6.4 kilograms of silica-gel powders (100-200 order), stir, drying obtains blend sample;
2) blend sample being carried out silica gel column chromatography, is eluent with ETHYLE ACETATE, carries out gradient elution, and wherein, the granularity of the sorbent material silica gel in the silicagel column is the 100-200 order, and the column diameter of silicagel column is 1: 10 with the ratio of post height; Sorbent material silica gel is 20: 1 with the ratio of the weight of crude mixture, and eluent is an ETHYLE ACETATE, consumption 6000L, and elution flow rate is 300L/h, every 50L elutriant is collected first-class part;
That 3) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant contains that there is something special, and elutriant is merged into two parts: contain peoniflorin part, contain lactone glucoside of Radix Paeoniae part (both do not have intersection), distinguish evaporate to dryness; Get 1.73 kilograms of peoniflorins, 1.02 kilograms of lactone glucoside of Radix Paeoniae; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%.
Detecting paeoniflorin content through HPLC is 93.42%; Lactone glucoside of Radix Paeoniae content is 92.77%.
With commercially available Radix Paeoniae Alba total glycosides is raw material (through measuring paeoniflorin content 24.2%, lactone glucoside of Radix Paeoniae 15.9%).
1, purification process
1) Radix Paeoniae Alba extract is 10 kilograms, all dissolves the back with 70% ethanol and adds 12.1 kilograms of silica-gel powders (100-200 order), stirs, and evaporate to dryness gets blend sample;
2) blend sample being carried out silica gel column chromatography, is eluent with the mixture of ETHYLE ACETATE and water, carries out gradient elution, and wherein, the granularity of the sorbent material silica gel in the silicagel column is the 100-200 order, and the column diameter of silicagel column is 1: 6 with the ratio of post height; Sorbent material silica gel is 16: 1 with the ratio of the weight of blend sample, and the volume ratio of ETHYLE ACETATE and water is 100: 3.5 in the eluent, and the eluent consumption is 5000L, and elution flow rate is 200L/h, and every 50L elutriant is collected first-class part;
That 3) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant contains that there is something special, and elutriant is merged into two parts: contain peoniflorin part, contain lactone glucoside of Radix Paeoniae part (both cross sections are incorporated the lactone glucoside of Radix Paeoniae part into), distinguish evaporate to dryness; Get 2.53 kilograms of peoniflorins, 1.08 kilograms of lactone glucoside of Radix Paeoniae; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%.
Detecting paeoniflorin content through HPLC is 93.4%; Lactone glucoside of Radix Paeoniae content is 82.9%.
1, the extraction of medicinal material
100 kilograms of exsiccant milli root of herbaceous peony roots, after the pulverizing, in the 2 tons of traditional Chinese medicine extraction jars of packing into, the adding mass percent concentration is 95% ethanol; Heating and refluxing extraction three times, the alcoholic acid volume that extracts usefulness is followed successively by 800L, 600L, 600L; Extraction time is followed successively by 3h, 3h, 2h;
After No. three extracting solutions merging, adopt vacuum decompressioning and concentrating tank to carry out concentrating under reduced pressure, be concentrated into dried; Make 18 kilograms of Radix Paeoniae Alba extracts, wherein the temperature of concentrating under reduced pressure is 60 ℃, the relative vacuum degree is-0.09～-0.08MPa; The specific density of Chinese herbaceous peony liquid concentrator is 1.21, and volume is 250L.
2, purification process
1) after adding 70% ethanol 25L all dissolves in Radix Paeoniae Alba extract, add 20 kilograms of silica gel for chromatography powder (100-200 order), stir, drying obtains blend sample;
2) blend sample being carried out silica gel column chromatography, is eluent with ETHYLE ACETATE and water mixed solvent, carries out wash-out, and wherein, the granularity of the sorbent material silica gel in the silicagel column is the 100-200 order, and the column diameter of silicagel column is 1: 8 with the ratio of post height; Sorbent material silica gel is 6: 1 with the ratio of the weight of lactone glucoside of Radix Paeoniae bullion, and the volume ratio of ETHYLE ACETATE and water is 100: 2.5 in the eluent, eluent consumption 2500L, and elution flow rate is 200L/h per hour, every 50L elutriant is collected as first-class part;
That 3) adopts that tlc (TLC method) detects peoniflorin and lactone glucoside of Radix Paeoniae in the elutriant contains that there is something special, and elutriant is merged into two parts: contain peoniflorin part, contain lactone glucoside of Radix Paeoniae part (both cross sections are incorporated the lactone glucoside of Radix Paeoniae part into), distinguish evaporate to dryness; Get 3.61 kilograms of peoniflorins, 2.16 kilograms of lactone glucoside of Radix Paeoniae; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%.Detecting paeoniflorin content through HPLC is 72.83%; Lactone glucoside of Radix Paeoniae content is 64.59%.
3, refinement treatment
1) get 2 kilograms of the lactone glucoside of Radix Paeoniae bullions that a step obtains, after dissolving fully with 70% ethanol 3.5L, add 2.5 kilograms of silica gel for chromatography powder (100-200 order), stir, drying obtains the lactone glucoside of Radix Paeoniae sample;
2) the lactone glucoside of Radix Paeoniae sample being carried out silica gel column chromatography, is eluent with ETHYLE ACETATE and acetone mixed solvent, carries out wash-out, and wherein, the granularity of the sorbent material silica gel in the silicagel column is the 100-200 order, and the column diameter of silicagel column is 1: 10 with the ratio of post height; Sorbent material silica gel is 15: 1 with the ratio of the weight of lactone glucoside of Radix Paeoniae bullion, and the volume ratio of ETHYLE ACETATE and acetone is 10: 1 in the eluent, eluent consumption 1000L, and elution flow rate is 200L/h per hour, every 50L elutriant is collected as first-class part;
That 3) adopts that tlc (TLC method) detects lactone glucoside of Radix Paeoniae in the elutriant contains that there is something special, obtains lactone glucoside of Radix Paeoniae wash-out part, evaporate to dryness; Get 1.17 kilograms of lactone glucoside of Radix Paeoniae, wherein, the thin layer plate that the TLC method is used is the silica gel G plate; Developping agent is the mixed solution of chloroform, methyl alcohol, and the volume ratio of chloroform and methyl alcohol is 4: 1, behind the ascending development; Spray is with 5% ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes.Detecting lactone glucoside of Radix Paeoniae content through HPLC is 93.24%.
Embodiment 6
Except the medicinal material extract step adopts fresh river radix paeoniae rubrathe branches and leaves, the mixture of root is raw material for 500 kilograms; After the chopping, in the 3 tons of diacolation jars of packing into, be that percolate carries out the diacolation extraction with the deionized water; The volume of percolate is 3800L, and the flow velocity that diacolation extracts is 50L/h; Percolate carries out concentrating under reduced pressure after merging; Being concentrated into does not have the alcohol flavor, makes the Chinese herbaceous peony liquid concentrator, and wherein the temperature of concentrating under reduced pressure is 80 ℃; The relative vacuum degree is-0.095～-0.08MPa; The specific density of Chinese herbaceous peony liquid concentrator is outside 1.25, and all the other are identical with embodiment 3, refining 1.96 kilograms of peoniflorins, 0.67 kilogram of the lactone glucoside of Radix Paeoniae that obtains.Detect through HPLC, paeoniflorin content is 79.4%; Lactone glucoside of Radix Paeoniae content is 73.7%.
Embodiment 7
1) get 1.0 kilograms of lactone glucoside of Radix Paeoniae (purity 92.77%) that embodiment 3 obtains as sample, with small amount of methanol the lactone glucoside of Radix Paeoniae sample is all dissolved the back and add 1.2 kilograms of silica-gel powders (100-200 order), stir, drying makes the lactone glucoside of Radix Paeoniae sample;
2) the lactone glucoside of Radix Paeoniae sample being carried out silica gel column chromatography, is that eluent carries out wash-out with the mixture of ETHYLE ACETATE-water, and wherein, the granularity of the sorbent material silica gel in the silicagel column is the 100-200 order, and the column diameter of silicagel column is 1: 5 with the ratio of post height; Sorbent material silica gel is 30: 1 with the ratio of the weight of lactone glucoside of Radix Paeoniae sample, and the volume ratio of ETHYLE ACETATE and water is 100: 3 in the eluent, and elution volume is 2000L, and elution flow rate is 80L/h, and every 50L elutriant is collected first-class part;
That 3) adopts that tlc (TLC method) detects lactone glucoside of Radix Paeoniae in the elutriant contains that there is something special, merges the elutriant that contains lactone glucoside of Radix Paeoniae, behind the evaporate to dryness 0.65 kilogram of lactone glucoside of Radix Paeoniae; Wherein, the thin layer plate that the TLC method is used is the silica gel G plate, and developping agent is the mixed solution of chloroform, methyl alcohol; The volume ratio of chloroform and methyl alcohol is 4: 1; Behind the ascending development, spray ethanol solution of sulfuric acid, 150 ℃ of heating colour developings after 5 minutes with 5%.
Detect through HPLC, lactone glucoside of Radix Paeoniae content is 99.3%, sees accompanying drawing 5.
The HPLC testing conditions is: instrument: Water 515 pumps, 2487 detectors; Chromatographic column: KromasilRP-C18; Moving phase: acetonitrile: 0.1% phosphate aqueous solution (13: 87); Detect wavelength: 230nm; Flow velocity: 1.0ml/min.
Embodiment 8 lactone glucoside of Radix Paeoniae sheets
Get lactone glucoside of Radix Paeoniae 400 grams of embodiment 2 gained, add starch 100 grams, Magnesium Stearate 30 grams mix, and compacting is 10000 on tabletting machine.Every contains the about 40mg of lactone glucoside of Radix Paeoniae, and the patient takes 3 every day, is used to treat coronary atherosclerotic heart disease and stenocardia.
The preparation of embodiment 9 peoniflorin compound preparations
Peoniflorin (purity 93.4%) 180 grams
Salvianolic acid B (purity 98.1) 70 grams
Ginsenoside Rg1's (purity 99.3) 50 grams
Borneol 45 grams
Said components mixes, and in the hard gelatin capsule of packing into, makes 4000 capsules, is used to treat coronary atherosclerotic heart disease and stenocardia.
Claims (14)
1. process for purification for preparing lactone glucoside of Radix Paeoniae and peoniflorin simultaneously, comprise with silica gel column chromatography method to Chinese herbaceous peony medicinal material or Radix Paeoniae Alba extract separate, purifying.
2. process for purification for preparing lactone glucoside of Radix Paeoniae and peoniflorin simultaneously comprises as follows step in sequence:
1) the Chinese herbaceous peony medicinal material of pulverizing is joined in the extraction solution, extract processing, extracting solution concentrates the back and adopts macroporous adsorbent resin to carry out the removal of impurities separating treatment, and the resin column elutriant that collect, merging contains peoniflorin and lactone glucoside of Radix Paeoniae obtains the resin column eluate;
2) the resin column eluate is carried out 1-2 purification by silica gel column chromatography and handle, the eluent wash-out, the Fractional Collections elutriant after thin layer detects, merges the silicagel column elutriant that contains peoniflorin and lactone glucoside of Radix Paeoniae respectively;
3) silicagel column elutriant concentrating under reduced pressure obtains peoniflorin and lactone glucoside of Radix Paeoniae respectively.
3. process for purification for preparing lactone glucoside of Radix Paeoniae and peoniflorin simultaneously comprises as follows step in sequence:
1) the Chinese herbaceous peony medicinal material of pulverizing is joined in the extraction solution, extract processing, extracting solution concentrates laggard row and carries out 1-3 purification by silica gel column chromatography processing; The eluent wash-out; The Fractional Collections elutriant after thin layer detects, merges the silicagel column elutriant that contains peoniflorin and lactone glucoside of Radix Paeoniae respectively;
2) silicagel column elutriant concentrating under reduced pressure obtains peoniflorin and lactone glucoside of Radix Paeoniae respectively.
4. process for purification for preparing lactone glucoside of Radix Paeoniae and peoniflorin simultaneously comprises as follows step in sequence:
1) the total glycosides of white peony root is directly carried out 1-3 purification by silica gel column chromatography and handle, the eluent wash-out, the Fractional Collections elutriant after thin layer detects, merges the silicagel column elutriant that contains peoniflorin and lactone glucoside of Radix Paeoniae respectively;
2) silicagel column elutriant concentrating under reduced pressure obtains peoniflorin and lactone glucoside of Radix Paeoniae respectively.
5. process for purification as claimed in claim 2 is characterized in that ethanol or mass percent concentration that the extraction solution selection water described in the step 1), mass percent concentration are 20-70% are the methyl alcohol of 20-70%, is preferably water extraction.
6. process for purification as claimed in claim 2 is characterized in that macroporous adsorbent resin selection D101, AB-8, DM130H, XAD-2, D201, HP-20, X-5, H103, DM11 or the ADS-17 type resin described in the step 1).
7. like claim 3,4 described process for purification, it is characterized in that it is that ethanol or the mass percent concentration of 90-99.9% is the methyl alcohol of 90-99.9% that the extraction solution described in the step 1) is selected mass percent concentration, is preferably 95% extraction using alcohol.
8. like claim 2,3,4 described process for purification, it is characterized in that the silica gel that described purification by silica gel column chromatography handles and the ratio of the weight of sample to be purified are 5-50: 1, be preferably 6-20: 1.
9. like claim 2,3,4 described process for purification; It is characterized in that the eluent that described purification by silica gel column chromatography is handled is ETHYLE ACETATE and methanol mixture; Wherein, methyl alcohol is 0-15 with the ratio of the volume of ETHYLE ACETATE: 100, carry out wash-out according to single concentration proportioning.
10. like claim 2,3,4 described process for purification; It is characterized in that the eluent that described purification by silica gel column chromatography is handled is ETHYLE ACETATE and alcoholic acid mixture; Wherein, ethanol is 0-10 with the ratio of the volume of ETHYLE ACETATE: 100, carry out wash-out according to single concentration proportioning.
11. like claim 2,3,4 described process for purification; It is characterized in that the eluent that described purification by silica gel column chromatography is handled is the mixture of ETHYLE ACETATE and acetone; Wherein, acetone is 0-20 with the ratio of the volume of ETHYLE ACETATE: 100, carry out wash-out according to single concentration proportioning.
12. like claim 2,3,4 described process for purification; It is characterized in that the eluent that described purification by silica gel column chromatography is handled is the mixture of ETHYLE ACETATE and water; Wherein, water is 0-3.5 with the ratio of the volume of ETHYLE ACETATE: 100, carry out wash-out according to single concentration proportioning.
13. like claim 1,2,3,4 described process for purification, the purity of the lactone glucoside of Radix Paeoniae that it is characterized in that preparing is 50-99.9%, wherein preferred purity is 86%-99%, and further preferred purity is 91-97%.
14. like claim 1,2,3,4 described process for purification, the purity of the peoniflorin that it is characterized in that preparing is 50-99.9%, wherein preferred purity is 86%-99%, and further preferred purity is 91-97%.
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| CN201010249421XA CN102372750A (en) | 2010-08-10 | 2010-08-10 | Method for simultaneously preparing albiflorin and paeoniflorin |
| PCT/CN2010/076636 WO2012019373A1 (en) | 2010-08-10 | 2010-09-06 | Method for preparing paeoniflorin and albiflorin |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103044503A (en) * | 2012-12-24 | 2013-04-17 | 浙江工业大学 | Method for rapidly and efficiently extracting paeoniflorin and albiflorin |
| CN107868113A (en) * | 2017-11-14 | 2018-04-03 | 郑州轻工业学院 | A kind of method that Paeoniflorin is extracted in the seed dregs of rice from Chinese herbaceous peony |
| CN109232687A (en) * | 2018-10-09 | 2019-01-18 | 江苏农牧科技职业学院 | A kind of extracting method of Chinese herbaceous peony plant different parts paeoniflorin content |
| CN115677789A (en) * | 2021-07-23 | 2023-02-03 | 广州白云山汉方现代药业有限公司 | Preparation method of paeoniflorin-6-O' -benzene sulfonate |
| CN115677790A (en) * | 2021-07-23 | 2023-02-03 | 广州白云山汉方现代药业有限公司 | Method for synthesizing paeoniflorin derivative |
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| CN104725448A (en) * | 2013-12-19 | 2015-06-24 | 北京农学院 | Albiflorin extracting method |
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| CN1169821C (en) * | 2002-03-07 | 2004-10-06 | 上海中药创新研究中心 | Glycosides compound monomer in Chinese herbaceous peony, and method for extracting and separating same |
| CN100336524C (en) * | 2005-07-27 | 2007-09-12 | 南京海陵中药制药工艺技术研究有限公司 | Method for preparing extract product of paeoniflorin |
| CN101607975B (en) * | 2009-07-16 | 2011-07-20 | 宁波立华植物提取技术有限公司 | Method for separating and preparing peony lactone glucoside by simulation moving bed chromatography method |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103044503A (en) * | 2012-12-24 | 2013-04-17 | 浙江工业大学 | Method for rapidly and efficiently extracting paeoniflorin and albiflorin |
| CN107868113A (en) * | 2017-11-14 | 2018-04-03 | 郑州轻工业学院 | A kind of method that Paeoniflorin is extracted in the seed dregs of rice from Chinese herbaceous peony |
| CN109232687A (en) * | 2018-10-09 | 2019-01-18 | 江苏农牧科技职业学院 | A kind of extracting method of Chinese herbaceous peony plant different parts paeoniflorin content |
| CN115677789A (en) * | 2021-07-23 | 2023-02-03 | 广州白云山汉方现代药业有限公司 | Preparation method of paeoniflorin-6-O' -benzene sulfonate |
| CN115677790A (en) * | 2021-07-23 | 2023-02-03 | 广州白云山汉方现代药业有限公司 | Method for synthesizing paeoniflorin derivative |
| CN115677789B (en) * | 2021-07-23 | 2024-10-01 | 广州白云山汉方现代药业有限公司 | Preparation method of paeoniflorin-6-O' -benzenesulfonate |
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