CN102492005A - Method for preparing paeoniflorin and albiflorin - Google Patents
Method for preparing paeoniflorin and albiflorin Download PDFInfo
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- CN102492005A CN102492005A CN2011104100679A CN201110410067A CN102492005A CN 102492005 A CN102492005 A CN 102492005A CN 2011104100679 A CN2011104100679 A CN 2011104100679A CN 201110410067 A CN201110410067 A CN 201110410067A CN 102492005 A CN102492005 A CN 102492005A
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Abstract
The invention discloses a method for preparing paeoniflorin and albiflorin, which mainly includes the following steps: selecting peony plant raw materials containing the paeoniflorin and the albiflorin, adopting water or alcohol-water mixed solvent to perform extraction, mixing extract, concentrating, filtering, absorbing the obtained crude extract by adopting pre-preprocessed macroporous resin, performing gradient elution by using ethanol-water mixed solvent, collecting 30% to 75% of ethanol elution parts eluent to perform concentration and drying. The obtained refined extract adopts pressurized column chromatography, using silica gel and modified silica gel as fillers, appropriate organic solvent is separated in mobile phase, flow parts containing the paeoniflorin and the albiflorin are collected respectively, concentrated and dried to obtain paeoniflorin finished products and albiflorin finished products with the purity more than 90%. The method for preparing the paeoniflorin and the albiflorin is concise in process, strong in operability, convenient in automation, capable of achieving comprehensive utilization of plant resources, convenient in solvent recycling, low in energy consumption, high in product purity, easy to achieve and high in industrialization.
Description
Technical field
The present invention relates to the preparation method of a kind of peoniflorin and root of herbaceous peony glycosides.
Technical background
Peoniflorin (paeoniflorin) and root of herbaceous peony glycosides (are claimed lactone glucoside of Radix Paeoniae again; Albiflorin) be a kind of monoterpene glycosides composition; Ubiquity in the Paeoniaceae plant is to mainly contain effective constituent and quality control standard in the traditional Chinese medicine root of herbaceous peony, the radix paeoniae rubrathe, the Tree Peony Bark, has multiple pharmacological effect and purposes; The total glycosides of white peony root is a kind of medicine of treating rheumatoid arthritis in China, and peoniflorin can be used as effective ingredient with root of herbaceous peony glycosides and is applied to relevant medicine and functional food field.
Preparation technology's correlative study document of Radix Paeoniae Alba total glycosides mainly concentrates on China.You Song etc. (one Chinese patent application number 02133298.3) disclose a kind of " composition and method of making the same of peoniflorin and lactone glucoside of Radix Paeoniae "; Said compsn extraction separation from Chinese herbaceous peony obtains; Wherein peoniflorin and the lactone glucoside of Radix Paeoniae ratio in said composition is 7: 3～9: 1, and its preparation technology is mainly refining through polymeric adsorbent, alumina column chromatography and silica gel column chromatography make.Zhang Xiantao etc. (one Chinese patent application number 200510041212.5) disclose a kind of " preparation method of extract product of paeoniflorin "; Said technology mainly adopts extraction using alcohol radix paeoniae rubrathe medicinal material, behind the last macroporous resin, and ethanol elution; Elutriant concentrates the back and goes up polyamide resin, gets content 90% above peoniflorin.Zhu Jingjian etc. (one Chinese patent application number 02110973.7) disclose a kind of " glycoside compound monomer, extraction and isolating method in the Chinese herbaceous peony ", and said composition comprises peoniflorin, lactone glucoside of Radix Paeoniae, benzoylpaeoniflorin and Hydroxy peoniflorin, and its method mainly adopts the root of herbaceous peony or radix paeoniae rubrathe swelling in alcohol solution; Reflux is concentrated into medicinal extract, uses the acetone soln supersound extraction; Concentrate; Silica gel mixed sample, the rough segmentation of last vacuum chromatographic column is carried out distribution chromatography repeatedly through silicagel column again and is obtained.Shi Renbing etc. (one Chinese patent application number 200710111231. *) disclose a kind of " extract of total glucosides of paeony and preparation method thereof "; Said extract mainly comprises peoniflorin, RADIX PAEONIAE ALBA glycosides, lacdtlorin, peony lactone A, B, C, oxypaeoniflorin, benzoylpaeoniflorin and verivate thereof etc., can from each plant parts of Paeoniaceae, prepare.
Through studying for a long period of time, adopt the technology of macroporous resin technology purifying Radix Paeoniae Alba total glycosides comparatively ripe at present, but peoniflorin and root of herbaceous peony glycosides can not separate, general technology such as SX also are difficult to reach separating effect.Bibliographical information adopts method separation and purification peoniflorin and root of herbaceous peony glycosides monomers such as normal pressure silica gel column chromatography, high-speed counter-current chromatography, but that the former post is imitated is lower, dress post and detecting operation are complicated, and the latter needs special plant and instrument, and the two all is difficult to realize suitability for industrialized production.The peoniflorin and the root of herbaceous peony glycosides monomer of mass-producing at present still do not have the commercially available prod, explore feasible industrialized manufacturing technique, are that technical barrier to be solved is arranged at present.
Summary of the invention
The purpose of this invention is to provide a kind of purity greater than 90%, be easy to realize the peoniflorin and the root of herbaceous peony glycosides preparation technology of industrialization.
The method for preparing peoniflorin and root of herbaceous peony glycosides provided by the invention may further comprise the steps:
(1) choose the Paeoniaceae plant material that contains peoniflorin and root of herbaceous peony glycosides, adopt water or alcohol-water mixed solvent to extract, extracting solution merges, and concentrates, and filters, and gets crude extract;
(2) by (1) gained crude extract, adopt the good macroporous resin of pre-treatment to adsorb, press 0-20%, 30-75% ethanol gradient elution with the alcohol-water mixed solvent again, collect 30-75% ethanol elution position elutriant, concentrate, drying must be made with extra care extract;
(3) by the refining extract of (2) gained, adopting the pressured column chromatogram, is filler with silica gel or modified silica-gel; Suitable organic solvent is that moving phase is separated, and collects stream part of containing peoniflorin and root of herbaceous peony glycosides respectively, concentrates; Drying can obtain purity greater than 90% peoniflorin and root of herbaceous peony glycosides finished product.
Paeoniaceae plant described in the said process step (1) is any one in the root of herbaceous peony, the radix paeoniae rubrathe, the tree peony, and said plant material is any one in roots of plants, stem, leaf, the rhizome.The extraction solvent is any one in water, the alcohol-water.Said process for extracting can be any one in refluxing extraction, supersound extraction, microwave-assisted extraction, the countercurrent extraction.
In the said process step (2), said macroporous resin is polystyrene or acrylic resin, wherein preferred nonpolar or low-pole macroporous resin.Preferably press 0-10%, 30-70% ethanol gradient elution during the macroporous resin gradient elution.
Pressured column chromatogram described in the said process step (3) is low pressure or middle compression leg chromatogram, and column length is the 10-100 cm range, preferred 15-100 centimetre; Column internal diameter can be chosen as the 2-100 cm range according to the production needs, preferred 10-50 centimetre.Said filler can be silica gel, and said moving phase is any one in chloroform-methanol, methylene chloride-methanol, ETHYLE ACETATE-methyl alcohol, the ethyl acetate-ethanol.Said filler also can be carbon 18 modified silica-gels, and said moving phase is any one in methanol-water, the methanol-water-organic acid, wherein preferred volatile first of organic acid or acetate.Said stream part of containing peoniflorin and root of herbaceous peony glycosides can be adopted online ultraviolet detection, or the thin layer of off-line detects or Liquid Detection.
The present invention is through peoniflorin and root of herbaceous peony glycosides technical study; The technology of preparing route of being accomplished has following characteristic and advantage: (1) medicinal material can be selected the various plant materials of Paeoniaceae that contain peoniflorin and root of herbaceous peony glycosides for use; Comprise in the root of herbaceous peony, the radix paeoniae rubrathe, the tree peony any one; Comprise any one position in the root, stem, leaf, rhizome of plant, enlarge and enriched effective comprehensive utilization of plant resources; (2) adopt preferred macroporous resin gradient elution technology, effectively enrichment be rich in the component of peoniflorin and root of herbaceous peony glycosides, simplified subsequent purification technology burden; (3) novelty is used low pressure or middle compression leg chromatogram operation, has realized the robotization and the operability of monomer purifying operation, successfully obtains purity greater than 90% monomer finished product.Operational path economical rationality of the present invention, efficient are high, energy consumption is low, can realize making full use of of plant resources, and solvent is convenient to reclaim and recycle easy realization of industrial production.
Content of the present invention is accomplished through lot of experiments, process optimization analysis, describes with following specific embodiment.
Embodiment
Peoniflorin of the present invention and root of herbaceous peony glycosides are by the represented method manufacturing of following examples, and involved method is the technique means that those skilled in the art can grasp and use.But following examples must not be interpreted as the restriction to this area invention claim of going up in all senses.
Embodiment 1 macroporous resin Static Adsorption performance is investigated
Take by weighing 1kg root of herbaceous peony medicine materical crude slice, with 8L70% alcohol reflux 2 times, each 2h filters, merging filtrate, and being evaporated to does not have the alcohol flavor, and the adjustment soup makes every 1ml soup be equivalent to the 0.5g crude drug, and is subsequent use.
Take by weighing the heavy 1.00g of each model resin dry; Place the tool plug Erlenmeyer flask of 10 50ml respectively, add root of herbaceous peony extracting solution (10ml of 0.5g crude drug/ml), 6h vibrates under 35 ℃ of conditions in the constant-temperature shaking case; Vibration velocity is 180prm; With the root of herbaceous peony extracting solution vacuum filtration after the absorption, filtrating is measured root of herbaceous peony glycosides and root of herbaceous peony glycosides content with reference to 2010 editions official methods with the HPLC method through suitably dilution.The good resin of absorption after the vacuum-drying, adds 10ml95% ethanol with washing 3 times, the 6h that in the constant-temperature shaking case, vibrates under 35 ℃ of conditions equally, and vibration velocity is 180prm, carries out desorption.Stripping liquid is through suitably measuring peoniflorin and root of herbaceous peony glycosides content with HPLC after the dilution.The good resin of absorption after the vacuum-drying, adds 10ml95% ethanol with washing 3 times, the 6h that in the constant-temperature shaking case, vibrates under 35 ℃ of conditions equally, and vibration velocity is 180prm, carries out desorption.Stripping liquid is through suitably measuring peoniflorin and root of herbaceous peony glycosides content with HPLC after the dilution.
Come evaluating resin through calculating adsorptive capacity and desorption efficiency.Adsorptive capacity calculation formula (1) and desorption efficiency calculation formula (2) do;
(1)q
e＝(C
0-C
e)V
i/W；(2)D＝C
dV
d/(C
0-C
e)V
i×100％
In the formula (1), q
eBe resin absorption amount (mg/g), C
0Initial concentration solution, C
eAdsorb saturated back strength of solution, V
iBe sample volume, W is the resin dry weight.D is a desorption efficiency in the formula (2), C
dBe the concentration of elutriant composition to be measured after the desorption, V
dBe effluent volume, C
0, C
e, V
iWith last same.The result sees table 1.
Each model resin of table 1 is to maximal absorptive capacity and the desorption efficiency of Chinese herbaceous peony
Conclusion: ten kinds of resins can both attach by adsorption and desorption peoniflorin and root of herbaceous peony glycosides, but with polystyrene low-pole Resin A B-8 and LX38, LX17 is better for acrylic acid series Semi-polarity resin.
The preparation of embodiment 2 Radix Paeoniae Alba extracts
Take by weighing the 40kg white Peony Root, spend the night with 70% alcohol immersion, refluxing extraction 2 times, each 2h filters, merging filtrate, rotary evaporation is not to there being the alcohol flavor, and the adjustment soup makes every 1ml soup be equivalent to the 0.5g crude drug, and is subsequent use.Take by weighing 120kg (weight in wet base) LX38 resin, (in 300 * 2300cm), column volume is 60L to the stainless steel column of packing into, last appearance; Behind the absorption 1h, first water 300L, 10% ethanol 300L removes impurity; Use 50% ethanol 360L wash-out peoniflorin and root of herbaceous peony glycosides again, use 95% ethanol regenerating resin at last, flow velocity is 150-200L/h; 50% ethanol position is concentrated evaporate to dryness get 2.52kg, wherein peoniflorin purity is 24%, and root of herbaceous peony glycosides is 16%.
The preparation of embodiment 3 Radix Paeoniae Alba extracts
Take by weighing 40kg root of herbaceous peony medicine materical crude slice, spend the night with 70% alcohol immersion, refluxing extraction 2 times, each 2h filters, merging filtrate, rotary evaporation is not to there being the alcohol flavor, and the adjustment soup makes every 1ml soup be equivalent to the 0.5g crude drug, and is subsequent use.Take by weighing 120kg (weight in wet base) AB-8 resin, (in 300 * 2300cm), column volume is 60L to the stainless steel column of packing into, last appearance; Behind the absorption 1h, first water 300L, 10% ethanol 300L removes impurity; Use 50% ethanol 360L wash-out peoniflorin and root of herbaceous peony glycosides again, use 95% ethanol regenerating resin at last, flow velocity is 150-200L/h; 50% ethanol position is concentrated evaporate to dryness get 2.32kg, wherein peoniflorin purity is 22%, and root of herbaceous peony glycosides is 12%.
The preparation of embodiment 4 Radix Paeoniae Alba extracts
Take by weighing 40kg root of herbaceous peony rhizome, spend the night with 70% alcohol immersion, refluxing extraction 2 times, each 2h filters, merging filtrate, rotary evaporation is not to there being the alcohol flavor, and the adjustment soup makes every 1ml soup be equivalent to the 0.5g crude drug, and is subsequent use.Take by weighing 120kg (weight in wet base) LX17 resin, (in 300 * 2300cm), column volume is 60L to the stainless steel column of packing into, last appearance; Behind the absorption 1h, first water 300L, 10% ethanol 300L removes impurity, uses 50% ethanol 360L wash-out peoniflorin and root of herbaceous peony glycosides again; Use 95% ethanol regenerating resin at last, flow velocity is 150-200L/h, and 50% ethanol position is concentrated evaporate to dryness; Get 2.84kg, wherein peoniflorin purity is 27%, and root of herbaceous peony glycosides is 18%.
Embodiment 5 silica gel medium pressure posts prepare the monomer composition
Get embodiment 2 gained Radix Paeoniae Alba extract 8g, use dissolve with methanol, add 8g 200-300 order silica gel mixed sample, the compression leg system separates in the employing; Adorn post (150 * 35mm i.d.) with silica gel H, use eluent ethyl acetate 1000ml, flow velocity 50mL/min uses ETHYLE ACETATE: methyl alcohol=95: 5 wash-outs again; Ultraviolet 230nm detects, and collects peoniflorin stream part and root of herbaceous peony glycosides stream part successively, concentrating under reduced pressure; Drying gets peoniflorin 2.8g, root of herbaceous peony glycosides 1.2g, and purity is respectively 95.4% and 92.2%.
Embodiment 6 silica gel medium pressure posts prepare the monomer composition
Adopt chloroform: methyl alcohol (15: 1 to 13: 1,90min) gradient elution, all the other parameter conditions get peoniflorin 2.5g with embodiment 5, root of herbaceous peony glycosides 1.0g, purity is respectively 96.1% and 91.2%.
Press the reverse phase silica gel post to prepare the monomer composition among the embodiment 7
Get embodiment 2 gained Radix Paeoniae Alba extract 10g, the compression leg system separates in the employing, with reverse phase silica gel C dress post (400 * 70mmi.d.); Sample is with appearance on the 100mL water dissolution, with 18% methyl alcohol isocratic elution, flow velocity 50mL/min; Ultraviolet 230nm detects, and collects peoniflorin stream part and root of herbaceous peony glycosides stream part successively, concentrating under reduced pressure; Drying gets peoniflorin 3.3g, root of herbaceous peony glycosides 1.4g, and purity is respectively 93.6% and 90.5%.
Press the reverse phase silica gel post to prepare the monomer composition among the embodiment 8
Adopt 18% methyl alcohol (containing 1%HAc) isocratic elution, all the other parameter conditions get peoniflorin 3.7g with embodiment 7, root of herbaceous peony glycosides 1.6g, and purity is respectively 98.1% and 94.2%.
Claims (10)
1. the preparation method of peoniflorin and root of herbaceous peony glycosides is characterized in that the preparation method of said peoniflorin and root of herbaceous peony glycosides is following:
(1) choose the Paeoniaceae plant material that contains peoniflorin and root of herbaceous peony glycosides, adopt water or alcohol-water mixed solvent to extract, extracting solution merges, and concentrates, and filters, and gets crude extract;
(2) by (1) gained crude extract, adopt the good macroporous resin of pre-treatment to adsorb, press 0-20%, 30-75% ethanol gradient elution with the alcohol-water mixed solvent again, collect 30-75% ethanol elution position elutriant, concentrate, drying must be made with extra care extract;
(3) by the refining extract of (2) gained, adopting the pressured column chromatogram, is filler with silica gel or modified silica-gel; Suitable organic solvent is that moving phase is separated, and collects stream part of containing peoniflorin and root of herbaceous peony glycosides respectively, concentrates; Drying can obtain purity greater than 90% peoniflorin and root of herbaceous peony glycosides finished product.
2. according to the preparation method of said peoniflorin of claim 1 and root of herbaceous peony glycosides, it is characterized in that said Paeoniaceae plant is any one in the root of herbaceous peony, the radix paeoniae rubrathe, the tree peony, said plant material is any one in roots of plants, stem, leaf, the rhizome.
3. according to the preparation method of said peoniflorin of claim 1 and root of herbaceous peony glycosides, it is characterized in that its extraction solvent is any one in water, the alcohol-water.
4. according to the preparation method of said peoniflorin of claim 1 and root of herbaceous peony glycosides, it is characterized in that process for extracting described in its preparation methods steps (1) is any one in refluxing extraction, supersound extraction, microwave-assisted extraction, the countercurrent extraction.
5. according to the preparation method of said peoniflorin of claim 1 and root of herbaceous peony glycosides, it is characterized in that macroporous resin is polystyrene or acrylic resin described in its preparation methods steps (2), wherein preferred nonpolar or low-pole macroporous resin.
6. according to the preparation method of said peoniflorin of claim 5 and root of herbaceous peony glycosides, it is characterized in that the alcohol-water mixed solvent is preferably pressed 0-10%, 30-70% ethanol gradient elution in its preparation methods steps (2).
7. according to the preparation method of said peoniflorin of claim 1 and root of herbaceous peony glycosides, it is characterized in that pressured column chromatogram described in its preparation methods steps (3) is low pressure or middle compression leg chromatogram, column length is the 10-100 cm range, and column internal diameter is the 2-100 cm range.
8. according to the preparation method of said peoniflorin of claim 7 and root of herbaceous peony glycosides; It is characterized in that filler is a silica gel described in its preparation methods steps (3), said moving phase is any one in chloroform-methanol, methylene chloride-methanol, ETHYLE ACETATE-methyl alcohol, the ethyl acetate-ethanol.
9. according to the preparation method of said peoniflorin of claim 7 and root of herbaceous peony glycosides, it is characterized in that filler described in its preparation methods steps (3) is carbon 18 modified silica-gels, said moving phase is any one in methanol-water, the methanol-water-organic acid.
10. according to the preparation method of said peoniflorin of claim 7 and root of herbaceous peony glycosides, it is characterized in that stream part of containing peoniflorin and root of herbaceous peony glycosides described in its preparation methods steps (3) adopts online ultraviolet detection or offline inspection.
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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 |
| CN103584093A (en) * | 2013-10-29 | 2014-02-19 | 无限极（中国）有限公司 | Application of white peony root extract in preparation of health food or cosmetic with anti-radiation and anti-aging effects |
| CN103784523A (en) * | 2014-01-28 | 2014-05-14 | 齐鲁工业大学 | Peony polyphenol extraction process |
| CN104072550A (en) * | 2013-03-25 | 2014-10-01 | 河北以岭医药研究院有限公司 | Separation method of monoterpene and saponins components in traditional Chinese medicine composition vegetable drug midbody |
| CN111122731A (en) * | 2019-12-27 | 2020-05-08 | 贵州景峰注射剂有限公司 | Quality detection method for radix paeoniae rubra |
| CN111388542A (en) * | 2020-03-24 | 2020-07-10 | 首都医科大学 | Method for extracting monoterpene glycoside active ingredient from non-medicinal part of radix paeoniae alba |
| CN112807257A (en) * | 2020-03-23 | 2021-05-18 | 上海铮信生物科技有限公司 | Preparation method of radix Paeoniae extract |
| CN113750140A (en) * | 2021-04-14 | 2021-12-07 | 宁波职业技术学院 | Application of total glucosides of paeony in preparing medicine for treating rheumatoid arthritis |
| CN113769692A (en) * | 2021-09-29 | 2021-12-10 | 四川聚元药业集团有限公司 | Preparation reation kettle of high-purity albiflorin |
| CN115677796A (en) * | 2022-11-23 | 2023-02-03 | 四川聚元药业集团有限公司 | Method for extracting paeoniflorin from white paeony root |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044503A (en) * | 2012-12-24 | 2013-04-17 | 浙江工业大学 | Method for rapidly and efficiently extracting paeoniflorin and albiflorin |
| CN104072550A (en) * | 2013-03-25 | 2014-10-01 | 河北以岭医药研究院有限公司 | Separation method of monoterpene and saponins components in traditional Chinese medicine composition vegetable drug midbody |
| CN104072550B (en) * | 2013-03-25 | 2018-05-29 | 河北以岭医药研究院有限公司 | The separation method of monoterpene and saponin component in Chinese medicine composition autonomic drug intermediate |
| CN103584093A (en) * | 2013-10-29 | 2014-02-19 | 无限极（中国）有限公司 | Application of white peony root extract in preparation of health food or cosmetic with anti-radiation and anti-aging effects |
| CN103584093B (en) * | 2013-10-29 | 2016-05-18 | 无限极（中国）有限公司 | Radix paeoniae alba extraction has the application in health food or the cosmetics of radioresistance and senile-resistant efficacy in preparation |
| CN103784523A (en) * | 2014-01-28 | 2014-05-14 | 齐鲁工业大学 | Peony polyphenol extraction process |
| CN111122731A (en) * | 2019-12-27 | 2020-05-08 | 贵州景峰注射剂有限公司 | Quality detection method for radix paeoniae rubra |
| CN112807257A (en) * | 2020-03-23 | 2021-05-18 | 上海铮信生物科技有限公司 | Preparation method of radix Paeoniae extract |
| CN111388542A (en) * | 2020-03-24 | 2020-07-10 | 首都医科大学 | Method for extracting monoterpene glycoside active ingredient from non-medicinal part of radix paeoniae alba |
| CN113750140A (en) * | 2021-04-14 | 2021-12-07 | 宁波职业技术学院 | Application of total glucosides of paeony in preparing medicine for treating rheumatoid arthritis |
| CN113769692A (en) * | 2021-09-29 | 2021-12-10 | 四川聚元药业集团有限公司 | Preparation reation kettle of high-purity albiflorin |
| CN115677796A (en) * | 2022-11-23 | 2023-02-03 | 四川聚元药业集团有限公司 | Method for extracting paeoniflorin from white paeony root |
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