CN101085728A - Method for preparing paeonol and paeoniflorin from cortex moutan - Google Patents
Method for preparing paeonol and paeoniflorin from cortex moutan Download PDFInfo
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- CN101085728A CN101085728A CN 200710069983 CN200710069983A CN101085728A CN 101085728 A CN101085728 A CN 101085728A CN 200710069983 CN200710069983 CN 200710069983 CN 200710069983 A CN200710069983 A CN 200710069983A CN 101085728 A CN101085728 A CN 101085728A
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Abstract
The invention relates to a method for preparing paeonol and peony glycosides from root bark of tree peony. It compries following steps: immersing pieces of medical herb of root bark of tree peony in water, extracting through distillation and getting paeonol crystal; extracting dregs of a decoction with alcohol solution, decompressing extract, separating extract with D201 macroporous absorption resin and getting peony glycosides. The invention is characterized by full use of medical herb, increased peony glycosides purity, rational design, low cost, easy operation, good stability and suitability for industrial production.
Description
Technical field
The invention belongs to field of medicaments, particularly relate to process extraction, refining from the Chinese medicine root bark of tree peony, substep obtains the preparation method of Paeonol and peoniflorin.
Background technology
At present, in the world, herbal medicine all has certain market, along with people increasing and the aging of population to the health requirements level of understanding, sub-health stateization, people thirst for back to nature more, utilize the high pharmacological agent of pure natural degree, prevent some chemical synthetic drugs cann't be solved problem, so the application of natural plant exceeds the background of its original traditional national culture.From natural drug, seek the little and inexpensive medicine of side effect and become the target that countries in the world pharmaceutical manufacturer is chased.The European Community has carried out unified legislation to herbal medicine, state herbal medicine status such as Canada and Australia have legalized, United States Government has also drafted the plant amedica management method, the compound mixed preparation that begins to accept natural drug is as curative, and these provide good international environment for Chinese medicine enters international medical market as curative.On the other hand, along with the quickening of global economic integration progress, particularly China becomes a full member of WTO, and Chinese Medicine market incorporates the breadth and depth of international medical big market and will further aggravate.Face the enormous impact of Asian countries's traditional medicine product such as the cut-throat competition of powerful transnational medical group and Japan, Korea S, India, Thailand and European countries' plant amedicas such as Germany, France, numerous products that China's traditional Chinese medicine produces are owing to still can not meet the standard of international medical market and requirement and being kept outside of the door.
The root bark of tree peony is the dry root skin of cohosh tree peony (Paeonia suffruticosa Andr.), ground such as distribution Hebei, Henan, Shandong, Sichuan, Shaanxi, Gansu.All there is cultivation all parts of the country, medicinal material main product Anhui, are China tradition conventional Chinese medicine materials, its cold nature, and flavor is arduous, and the heart, liver, kidney channel are gone in cold, have heat-clearing, cool blood, and blood, the effect of the stasis of blood that disappears.The root bark of tree peony is concocted and to be seen China's beam Dai Taohong scape the earliest and write in " variorums ", thinks: " all urge to break, remove the heart." in the medical book such as Compendium of Material Medica record " root bark of tree peony core is not used as medicine, and need go it.”
Paeonol and peoniflorin are two kinds of main active substances in the root bark of tree peony.Modern medicine study proof Paeonol has antibacterial anti-inflammatory, analgesia, analgesic, spasmolysis, antianaphylaxis, invigorates blood circulation, changes effects such as silt, raise immunity, has purposes widely at medicine, spices, chemical field, for example toothpaste, perfumed soap, body lotion, hair growing liquid, medical disinfecting paper, women, infant hygiene articles for use, foodstuff additive, fodder additives etc.Peoniflorin has analgesia, calmness, protects the liver, anti-inflammatory, immunomodulatory, vasodilation, improve learning and memory behavior isoreactivity, can treat rheumatoid arthritis, hepatitis and senile relative disease etc.
At present, the patent, the bibliographical information that extract Paeonol from the root bark of tree peony are few, in order to improve yield, often adopt comparatively loaded down with trivial details method such as overcritical grade, need the plant and instrument of certain scale, have limited the application in industrial production.And do not have method report to obtain Paeonol and two kinds of materials of peoniflorin simultaneously at present from the root bark of tree peony, caused the waste of raw material to a certain extent, therefore, it is particularly important to set up a kind of method that can obtain these two kinds of essential substance from medicinal material simultaneously.
Summary of the invention
The object of the present invention is to provide a kind of preparation method who from the root bark of tree peony, obtains Paeonol and peoniflorin.
The preparation method of Paeonol of the present invention and peoniflorin comprises with steam distillation obtaining Paeonol that the dregs of a decoction add pure water extraction, and extracting solution separates this several steps of acquisition peoniflorin with macroporous adsorptive resins.
The present invention is achieved through the following technical solutions:
(1) the paeonol piece removal impurity that is soaked in water, oven dry is extracted with steam distillation, collects distillate, and freezing back is melted promptly and is filtered, and obtains the Paeonol crystal;
(2) dregs of a decoction add pure water extraction, the enrichment of extracting solution concentrating under reduced pressure;
(3) macroporous adsorptive resins on the concentrated solution, 0%-30% concentration aqueous ethanol purifying is used in first water flushing again, uses 20%-70 concentration aqueous ethanol desorbed solution wash-out again, collects elutriant and is evaporated to and do not have alcohol, and lyophilize promptly gets the peoniflorin part.
Wherein: in the step (1), the medicine materical crude slice soak time is 10-48 hour, and the distillate volume is that 8-15 doubly measures, and the distillate freezing time is 4-10 hour.Preferred paeonol piece soak time is 15-36 hour, and the distillate volume is that 10-12 doubly measures, and the distillate freezing time is 6-8 hour.Best the distillate volume is 12 times of amounts for the medicine materical crude slice soak time is 24 hours, and the distillate freezing time is 8 hours.
In the step (2), alcohol concn is 30%-95%, and solvent load 8-15 doubly measures, and heating is extracted 1-3 time, each 0.5-2 hour.Preferred alcohol concentration is 50%-80%, and solvent load 10-12 doubly measures, and heating is extracted 1-2 time, each 0.5-1 hour.Best alcohol concn is 70%, 10 times of amounts of solvent load, and heating is extracted 2 times, each 0.5 hour.
In the step (3), elution volume is a 1-4 column volume (BV) behind the purifying, and resolving the back elution volume is 3-6 BV.Preferred refined solution alcohol concn is 10%-20%, and elution volume is 2-3 BV, and the desorbed solution alcohol concn is 30%-50%, and elution volume is the 4-5 column volume.Best elution volume is 3 BV for the refined solution alcohol concn is 20%, and the desorbed solution alcohol concn is 40%, and elution volume is 4 BV.
Paeonol and peoniflorin according to method of the present invention is made can be made into said formulation on any pharmaceutics, also can cooperate other drug or component to make preparation together and use.
Paeonol that extraction obtains and peoniflorin and preparation allowable pharmaceutical excipients or carrier combinations are prepared into preparation, and its form comprises liquid preparation, granule, tablet, aerosol spray, lyophilized injectable powder, drops or capsule and pill.
The usefulness of the inventive method is:
(1) can from root bark of tree peony medicinal material, obtain Paeonol and peoniflorin by substep by the method for the invention, medicinal material has been carried out maximum utilization.
(2) present method can use comparatively simple method to obtain the higher Paeonol of purity, and simultaneously, peoniflorin is selected D for use when purifying
201The type macroporous resin, having solved other resins effectively can not improve the purity of peoniflorin greatly with tannin in the root bark of tree peony and the isolating problem of peoniflorin.Set up the method that from the root bark of tree peony, obtains Paeonol and peoniflorin simultaneously first.
(3) the method for the invention is that index is carried out comprehensive evaluation with effective component yield and yield of extract, has avoided pursuing the active constituent content height simply, and has caused yield of extract very low, is difficult to satisfy industrial production requirement.
(4) the present invention is reasonable in design, low-cost, easy to operate, good stability, is suitable for industrialization.
Description of drawings
Fig. 1 is a Paeonol 230nm liquid chromatogram.
Fig. 2 is a peoniflorin 230nm liquid chromatogram.
Embodiment
The present invention is further described in conjunction with the embodiments.Following each embodiment only is used to the present invention is described and is not limitation of the present invention.
Embodiment one
Get paeonol piece 500kg, 50 ℃ of dryings 6 hours were soaked 24 hours, and refluxing extraction is collected distillate to 12 times amount (6L) ,-4 ℃ freezing 8 hours, take out and melt back suction filtration at once, insolubles is Paeonol.The dregs of a decoction add 10 times of amount 70% aqueous ethanolic solution slight boiling condition heating and refluxing extraction 2 times, and each 0.5 hour, extracting liquid filtering merged, and is evaporated to 1g/mL (crude drug amount), last D
201Macroporous resin (0.2-0.6g raw medicinal herbs/g wet resin).Use the 4BV deionized water rinsing, discard, continue the 20% aqueous ethanolic solution purifying with 4BV, discard, use 4BV 40% aqueous ethanolic solution wash-out again, collect elutriant, being evaporated to does not have alcohol, and lyophilize promptly gets the peoniflorin part.Measure through liquid phase, the medicinal material extract rate of Paeonol is 2.06%, and the medicinal material extract rate of peoniflorin is 0.32%.
Embodiment two
Get paeonol piece 500kg, 50 ℃ of dryings 6 hours were soaked 10 hours, and refluxing extraction is collected distillate to 8 times amount (4L) ,-4 ℃ freezing 4 hours, take out and melt back suction filtration at once, insolubles is Paeonol.The dregs of a decoction add 10 times of amount 30% aqueous ethanolic solution slight boiling condition heating and refluxing extraction 1 time, and each 0.5 hour, extracting liquid filtering merged, and is evaporated to 1g/mL (crude drug amount), last D
201Macroporous resin (0.2-0.6g raw medicinal herbs/g wet resin).Use the 2BV deionized water rinsing, discard, continue the 10% aqueous ethanolic solution purifying with 3BV, discard, use 3BV 30% aqueous ethanolic solution wash-out again, collect elutriant, being evaporated to does not have alcohol, and lyophilize promptly gets the peoniflorin part.Measure through liquid phase, the medicinal material extract rate of Paeonol is 1.89%, and the medicinal material extract rate of peoniflorin is 0.30%.
Embodiment three
Get paeonol piece 500kg, 50 ℃ of dryings 6 hours were soaked 15 hours, and refluxing extraction is collected distillate to 12 times amount (6L) ,-4 ℃ freezing 6 hours, take out and melt back suction filtration at once, insolubles is Paeonol.The dregs of a decoction add 8 times of amount 50% aqueous ethanolic solution slight boiling condition heating and refluxing extraction 2 times, and each 0.5 hour, extracting liquid filtering merged, and is evaporated to 1g/mL (crude drug amount), last D
201Macroporous resin (0.2-0.6g raw medicinal herbs/g wet resin).Use the 3BV deionized water rinsing, discard, continue the 20% aqueous ethanolic solution purifying with 3BV, discard, use 3BV 50% aqueous ethanolic solution wash-out again, collect elutriant, being evaporated to does not have alcohol, and lyophilize promptly gets the peoniflorin part.Measure through liquid phase, the medicinal material extract rate of Paeonol is 1.92%, and the medicinal material extract rate of peoniflorin is 0.31%.
Embodiment four
Get paeonol piece 500kg, 50 ℃ of dryings 6 hours were soaked 48 hours, and refluxing extraction is collected distillate to 15 times amount (7.5L) ,-4 ℃ freezing 10 hours, take out and melt back suction filtration at once, insolubles is Paeonol.The dregs of a decoction add 15 times of amount 95% aqueous ethanolic solution slight boiling condition heating and refluxing extraction 3 times, and each 0.5 hour, extracting liquid filtering merged, and is evaporated to 1g/mL (crude drug amount), last D
201Macroporous resin (0.2-0.6g raw medicinal herbs/g wet resin).Use the 3BV deionized water rinsing, discard, continue the 30% aqueous ethanolic solution purifying with 3BV, discard, use 4BV 60% aqueous ethanolic solution wash-out again, collect elutriant, being evaporated to does not have alcohol, and lyophilize promptly gets the peoniflorin part.Measure through liquid phase, the medicinal material extract rate of Paeonol is 1.98%, and the medicinal material extract rate of peoniflorin is 0.29%.
Embodiment five Paeonols and content of paeoniflorin are measured
(1) assay (high performance liquid chromatography) of Paeonol among the embodiment one
Chromatographic conditionChromatographic column Agilent Zorbax SB-C
18Post (4.6mm * 150mm, 5 μ m); Adopt isocratic elution, mobile phase A is water mutually, and Mobile phase B is acetonitrile mutually; Mobile phase A is 55%, Mobile phase B is 45% isocratic elution; Flow velocity 1.0mLmin
-1Detect wavelength 230nm; 30 ℃ of column temperatures; Sample size 5 μ L.
The preparation of need testing solutionTake by weighing this product, in volumetric flask, be diluted to scale, shake up, promptly with dissolve with methanol solution.
Measuring methodThe accurate need testing solution of drawing injects liquid chromatograph, measures, and the result is referring to Fig. 2, and wherein 1 represents Paeonol.
(2) content of paeoniflorin is measured among the embodiment one
Chromatographic conditionChromatographic column Agilent Zorbax SB-C
18Post (4.6mm * 150mm, 5 μ m); Adopt isocratic elution, mobile phase A is water mutually, and Mobile phase B is acetonitrile mutually; Mobile phase A is 85%, Mobile phase B is 15% isocratic elution; Flow velocity 1.0mLmin
-1Detect wavelength 230nm; 30 ℃ of column temperatures; Sample size 5 μ L.
The preparation of need testing solutionTake by weighing this product, deposit in the volumetric flask, be diluted to scale, shake up, promptly with dissolve with methanol solution.
Measuring methodThe accurate need testing solution of drawing injects liquid chromatograph, measures, and the result is referring to Fig. 2, and wherein 1 represents peoniflorin.
The preparation of embodiment six dripping pills
Paeonol 0.5g and the 10.5g polyoxyethylene glycol-6000 of getting embodiment one mix, and heating and melting moves in the dripping pill drip irrigation behind the change material, and in ℃ whiteruss of medicine liquid droplet to 6～8, oil removing makes 300 of dripping pills.
The preparation of embodiment seven lyophilized injectable powders
Get Lignum Dalbergiae Odoriferae oil 1.5g, join in the saturated hydroxypropyl of 13ml, stirring and dissolving filters, and the filtrate cryodrying gets the inclusion compound powder of Lignum Dalbergiae Odoriferae oil and hydroxypropyl.Except that above-mentioned Lignum Dalbergiae Odoriferae oil closes the inclusion compound powder of hydroxypropyl, get peoniflorin 0.5g, N.F,USP MANNITOL 5.5g, Calcium Disodium Edetate 0.9g and the distilled water 2ml of embodiment one again, behind the said components mixing, lyophilize, 350 of packing, promptly.
The preparation of embodiment eight tablets
Get among the embodiment one that peoniflorin is an amount of to mix with Microcrystalline Cellulose, add 3% polyvidone ethanolic soln system softwood, cross 18 mesh sieve system particles, 60 ℃ of dryings 1 hour, whole, the adding talcum powder is an amount of, mixing, compressing tablet, promptly.
Embodiment nine capsular preparations
Get peoniflorin and peanut oil among the embodiment one and stir in 2: 18 ratio water dissolving type stainless steel and irritate, add an amount of gelatin and glycerine simultaneously and mix, emit and use the colloidal mill defibrination again, the mixed solution that grinds stirs, and makes soup; Under 40-50 ℃ of temperature, stir glycerine and distilled water miscible, again with the glycerin liquid temperature to 80-90 ℃, get gelatin and add wherein to mix and stir, become glue until off-bottom, glue was left standstill 4 hours, make offset plate with laminator and use for the pill operation; Above-mentioned soup of making and offset plate are sent into the pellet press pill, did cylinder typing in 4 hours at 22-25 ℃ of temperature katabatic wind then, again dry 16-20 hour of 25-30 ℃ of temperature katabatic wind, the qualified capsule and pill of pick, clean with 95% ethanol, dry 4 hours of 25-30 ℃ of katabatic wind, promptly.
The preparation of embodiment ten injection liquids
Get among the embodiment one that peoniflorin is an amount of to be dissolved with 40 ℃ of waters for injection, add an amount of pharmaceutical carrier isotonic agent, the pH value of regulator solution is 7.0-8.0, adds to the full amount of water for injection, remove thermal source with the ultra-fine filter ultrafiltration, after the mensuration pH value, use membrane filtration, after the packing, autoclaving, check, packing, promptly.
Claims (6)
1. preparation method who obtains Paeonol and peoniflorin from the root bark of tree peony is characterized in that realizing by following steps:
(1) the paeonol piece removal impurity that is soaked in water, oven dry is extracted with steam distillation, collects distillate, and freezing back is melted promptly and is filtered, and obtains the Paeonol crystal;
(2) dregs of a decoction add pure water extraction, the enrichment of extracting solution concentrating under reduced pressure;
(3) macroporous adsorptive resins on the concentrated solution, 0%-30% concentration aqueous ethanol purifying is used in first water flushing again, uses 20%-70 concentration aqueous ethanol desorbed solution wash-out again, collects elutriant and is evaporated to and do not have alcohol, and lyophilize promptly gets the peoniflorin part.
2. the preparation method who obtains Paeonol and peoniflorin from the root bark of tree peony according to claim 1 is characterized in that: the paeonol piece soak time is 10-48 hour in the step (1), and the distillate volume is that 8-15 doubly measures, and the distillate freezing time is 4-10 hour.
3. the preparation method who from the root bark of tree peony, obtains Paeonol and peoniflorin according to claim 1, it is characterized in that: alcohol solution extracts twice in the step (2), and alcohol concn is 30%-95%, and solvent load 8-15 doubly measures, heating is extracted 1-3 time, each 0.5-2 hour.
4. the preparation method who obtains Paeonol and peoniflorin from the root bark of tree peony according to claim 1 is characterized in that: adopt D in the step (3)
201The type macroporous resin.
5. according to claim 1 or the 4 described preparation methods that obtain Paeonol and peoniflorin from the root bark of tree peony, it is characterized in that: elution volume is a 1-4 column volume behind the middle purifying of step (3), and resolving the back elution volume is the 3-6 column volume.
6. the preparation method who from the root bark of tree peony, obtains Paeonol and peoniflorin according to claim 1, it is characterized in that: Paeonol that extraction obtains and peoniflorin and preparation allowable pharmaceutical excipients or carrier combinations are prepared into preparation, and its form comprises liquid preparation, granule, tablet, aerosol spray, lyophilized injectable powder, drops or capsule and pill.
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| CN101628866A (en) * | 2009-08-11 | 2010-01-20 | 张守力 | Extraction method of paeonol |
| CN101975833A (en) * | 2010-05-25 | 2011-02-16 | 江西中烟工业有限责任公司 | Method for measuring main active ingredient paeonol of traditional Chinese medicinal additive in cigarettes |
| CN101390962B (en) * | 2008-10-15 | 2011-06-22 | 安徽大学 | Preparation method of active components in root-bark tree peony by in-phase leaching and sub-item preparation |
| CN102423346A (en) * | 2011-12-26 | 2012-04-25 | 云南白药中草药芯片有限公司 | Tree peony root bark extract, as well as preparation method and application thereof |
| CN102499913A (en) * | 2011-10-31 | 2012-06-20 | 广西亿康药业股份有限公司 | Preparation method for refined and purified paeonol preparation |
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| CN105801392A (en) * | 2016-04-14 | 2016-07-27 | 重庆大学 | Extracting method of 2'-hydroxy-4'-methoxyacetopheone |
| CN107308177A (en) * | 2017-07-19 | 2017-11-03 | 辽宁华润本溪三药有限公司 | A kind of pharmaceutical composition of antalgic and inflammation relieving and preparation method thereof and purposes |
| CN108392488A (en) * | 2018-05-29 | 2018-08-14 | 刘娟 | Purposes of the Paeoniflorin in preparing IDO inhibitor |
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| CN101390962B (en) * | 2008-10-15 | 2011-06-22 | 安徽大学 | Preparation method of active components in root-bark tree peony by in-phase leaching and sub-item preparation |
| CN101628866A (en) * | 2009-08-11 | 2010-01-20 | 张守力 | Extraction method of paeonol |
| CN101975833A (en) * | 2010-05-25 | 2011-02-16 | 江西中烟工业有限责任公司 | Method for measuring main active ingredient paeonol of traditional Chinese medicinal additive in cigarettes |
| CN101975833B (en) * | 2010-05-25 | 2013-04-17 | 江西中烟工业有限责任公司 | Method for measuring main active ingredient paeonol of traditional Chinese medicinal additive in cigarettes |
| CN103327992B (en) * | 2010-12-03 | 2016-10-12 | 信一制药株式会社 | For prevent or treat inflammatory diseases comprise Caulis Trachelospermi extract and the pharmaceutical composition of Cortex Moutan extract and the method preparing this pharmaceutical composition |
| CN103327992A (en) * | 2010-12-03 | 2013-09-25 | 信一制药株式会社 | Pharmaceutical composition for preventing or treating inflammatory diseases comprising trachelospermi caulis extract and paeonia suffruticosa andrews extract, and method for preparing the same |
| US9694045B2 (en) | 2010-12-03 | 2017-07-04 | Sinil Pharmaceutical Co., Ltd. | Pharmaceutical composition for preventing or treating inflammatory diseases comprising trachelospermi caulis extract and paeonia suffruticosa andrews extract, and method for preparing the same |
| CN102499913A (en) * | 2011-10-31 | 2012-06-20 | 广西亿康药业股份有限公司 | Preparation method for refined and purified paeonol preparation |
| CN102423346A (en) * | 2011-12-26 | 2012-04-25 | 云南白药中草药芯片有限公司 | Tree peony root bark extract, as well as preparation method and application thereof |
| CN102423346B (en) * | 2011-12-26 | 2015-09-09 | 云南白药中草药芯片有限公司 | A kind of Cortex Moutan extract and its production and use |
| CN104983813A (en) * | 2015-06-16 | 2015-10-21 | 北京中医药大学 | Nasal delivery preparation for opening orifices and eliminating stagnant blood and preparing method of nasal delivery preparation for opening orifices and eliminating stagnant blood |
| CN104983813B (en) * | 2015-06-16 | 2018-07-10 | 北京中医药大学 | Open hole powder stasis of blood nasal cavity administrated preparation and preparation method thereof |
| CN105801392A (en) * | 2016-04-14 | 2016-07-27 | 重庆大学 | Extracting method of 2'-hydroxy-4'-methoxyacetopheone |
| CN107308177A (en) * | 2017-07-19 | 2017-11-03 | 辽宁华润本溪三药有限公司 | A kind of pharmaceutical composition of antalgic and inflammation relieving and preparation method thereof and purposes |
| CN107308177B (en) * | 2017-07-19 | 2022-05-17 | 辽宁华润本溪三药有限公司 | Analgesic and anti-inflammatory pharmaceutical composition and preparation method and application thereof |
| CN108392488A (en) * | 2018-05-29 | 2018-08-14 | 刘娟 | Purposes of the Paeoniflorin in preparing IDO inhibitor |
| CN110143877A (en) * | 2019-05-23 | 2019-08-20 | 中国水产科学研究院长江水产研究所 | The preparation method and applications of ferulic acid paeonol ester |
| CN110143877B (en) * | 2019-05-23 | 2022-06-21 | 中国水产科学研究院长江水产研究所 | Preparation method and application of paeonol ferulate |
| CN110613626A (en) * | 2019-09-18 | 2019-12-27 | 郑州轻工业学院 | Toothpaste containing paeoniflorin |
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| CN100491318C (en) | 2009-05-27 |
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