CN103709029A - Process for extracting and purifying ferulic acid from angelica cartilaginomarginata Nakai - Google Patents
Process for extracting and purifying ferulic acid from angelica cartilaginomarginata Nakai Download PDFInfo
- Publication number
- CN103709029A CN103709029A CN201310695017.9A CN201310695017A CN103709029A CN 103709029 A CN103709029 A CN 103709029A CN 201310695017 A CN201310695017 A CN 201310695017A CN 103709029 A CN103709029 A CN 103709029A
- Authority
- CN
- China
- Prior art keywords
- forulic acid
- radix angelicae
- angelicae sinensis
- extracting
- bone edge
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a process for extracting and purifying ferulic acid from angelica cartilaginomarginata Nakai. The process comprises the steps of smashing a raw material, namely angelica cartilaginomarginata Nakai; then, extracting by using an ultrasonic continuous countercurrent extractor and by taking hot water as a solvent to obtain a water extracting solution; centrifuging the obtained water extracting solution, and collecting the centrifugate; next, concentrating the centrifugate, dissolving a concentrate by using methanol, then, filtering, and collecting a methanol solution; adding petroleum ether into the methanol solution, uniformly stirring, then, standing for layering, collecting a methanol layer, separating ferulic acid from the methanol layer by using a simulated moving bed chromatographic separation technology, and purifying the ferulic acid. By using the process, finished products of the ferulic acid, which have the yield of over 75% and the purity of over 95%, can be obtained.
Description
Technical field:
The invention belongs to the field of separating extractive from plant, particularly a kind of technique of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis.
Background technology:
Bone edge Radix Angelicae Sinensis, umbelliferae angelica, formal name used at school Angelica cartilaginomarginata Nakai, perennial herb.Root is thicker, is fusiform.Florescence is in September.Mainly grow in sylvan life thick grass.In Northeast China and each province, east have distribution.All herbal medicine, root can be used as antispastic anodyne.
The chemical name of forulic acid (Ferulic Acid) is 4 hydroxyl 3 methoxy cinnamic acids, is one of derivative of TRANSCINNAMIC ACID (claiming again styracin, 3 phenyl 2 vinylformic acid, molecular structure).Forulic acid (Sodium Ferulate) has platelet aggregation-against, suppresses platelet 5-HT and discharges, and suppresses the generation of platelet thrombus element a2 (txa2), strengthens prostaglandin(PG) active, analgesia, the effects such as alleviating vascular spasm.To produce the basic raw material that is used for the treatment of the disease medicines such as cardiovascular and cerebrovascular diseases and oligoleukocythemia.As Sodium Ferulate, Limai capsule, Ferulic acid etc., it can play effect vigorous and graceful and protection skin simultaneously in human body.
At present, forulic acid is mainly to extract and obtain by chemosynthesis with from vegetable material.Chemosynthesis is to take 4-hydroxyl-3-methoxylbenxaldehyde by Witting-Horner and Knoeve-nagel reaction is synthetic, to obtain as raw material.But what this method obtained is the mixture of cis and trans-ferulaic acid, and long reaction time, is three weeks, and solvent load is large, and yield is low.From plant, extracting and obtaining forulic acid is mainly to prepare by enzyme process and alkaline process.Due to lignocellulose compact structure, the hydrolysis efficiency of enzymolysis process is lower.Although the ester bond and alkaline process can rupture, discharges forulic acid, while being equal to due to polysaccharide, xylogen and monomer whose, enter alkali lye, cause forulic acid separation difficulty.
Summary of the invention:
Primary and foremost purpose of the present invention is to provide a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis, can overcome the shortcoming and defect of prior art again simultaneously.The present invention utilizes ultrasonic continuous countercurrent extraction forulic acid, then utilizes routine techniques and simulated moving bed chromatography isolation technique purifying forulic acid, and acquisition purity is high, the product of quality better.
The object of the invention is to be achieved through the following technical solutions: a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis, specifically comprises the following steps:
(1) material bone edge Radix Angelicae Sinensis is pulverized, then utilized ultrasonic continuous countercurrent extractor to take hot water and extract as solvent;
(2) the bone edge Radix Angelicae Sinensis aqueous extract that will obtain through step (1) is centrifugal, collects centrifugate;
(3) centrifugate step (2) being obtained is concentrated, obtains enriched material;
(4) enriched material step (3) being obtained is with filtering after dissolve with methanol, removes not tolerantly, obtains methanol solution;
(5) in methanol solution, add sherwood oil, stratification after stirring, collects methanol layer;
(6) adopt simulated moving bed chromatography isolation technique separation and purification forulic acid from methanol layer.
In described step (1), material bone edge Radix Angelicae Sinensis powder is broken to 10～40 orders, ultrasonic power 20～200W, range of frequency 10～100KHz, extracting temperature is 60～100 ℃, raw material rate of advance is 5～30 ms/h, and water flow velocity is 20～100 ms/h, and raw material working direction is contrary with water (flow) direction.
In described step (2), centrifugation apparatus can adopt one or more series connection in tripod pendulum type batch centrifugal, disk plate centrifuge or tubular-bowl centrifuge.
In described step (3), adopt vacuum concentration, vacuum tightness is-0.05～-0.09Mpa, and thickening temperature is at 55～65 ℃, and in the enriched material obtaining, moisture controlled is in 5%.
In described step (4), enriched material: methyl alcohol=1: 1～10 (W/V), temperature range during dissolving is 50～64 ℃.
In described step (5), sherwood oil: methanol solution=1: 1～3 (V/V), churning time is not less than 20min, and time of repose is not less than 40min.
In described step (6), adopt simulated moving bed chromatography isolation technique separation and purification forulic acid from methanol layer, used simulation moving-bed be IV band structure, by 4～8 C18 chromatographic columns, formed, each band is composed in series by 1～2 root chromatogram column, moving phase is methyl alcohol: water (1% Glacial acetic acid)=70: 30, sample introduction flow velocity is 0.1～0.3ml/min, eluent flow rate is 2～6ml/min, extraction liquid flow velocity is 2～6ml/min, be 17～20min switching time, and chromatographic system service temperature is 25 ℃.
In described step (6), the forulic acid elutriant obtaining is concentrated into solid substance and accounts for 30～50%, then 0～5 ℃ standing 6～10 hours, collect crystallization, obtain high purity forulic acid.
Advantage of the present invention is under the effect of ultrasonic continuous countercurrent extraction, using water as extracting solvent agent, utilize simulated moving bed chromatography technology purifying forulic acid, improved greatly extraction efficiency, reduced the usage quantity of solvent, obtain the product that purity is higher, water can not produce and pollute environment simultaneously, has reduced significantly environmental pressure.
Embodiment:
Embodiment 1:
Take bone edge Radix Angelicae Sinensis, after pulverizing, cross 20 mesh sieves, utilize ultrasonic continuous countercurrent extractor to extract, ultrasonic power is 50W, and frequency is 50KHz, extract temperature 60 C, raw material rate of advance is 5 ms/h, and water flow velocity is 20 ms/h, and aqueous extract is centrifugal with tripod pendulum type batch centrifugal, centrifugate is concentrated into dry under vacuum tightness-0.06Mpa, temperature 60 C condition, obtains enriched material.5 times of amounts (V/W) methyl alcohol stirring and dissolving at 50 ℃ for enriched material, filters and to obtain methyl alcohol filtrate, and the sherwood oil to adding 0.5 times of volume in methyl alcohol filtrate, stirs 30min under normal temperature, and then standing 60min, collects methanol layer.Methanol layer carries out separation and purification by IV band simulated moving bed chromatography, moving phase is methyl alcohol: water (1% Glacial acetic acid)=70: 30, sample introduction flow velocity is 0.1ml/min, eluent flow rate is 2ml/min, extraction liquid flow velocity is 2ml/min, be 18min switching time, chromatographic system service temperature is 25 ℃, the extraction liquid that collection contains forulic acid, being concentrated into solid content is 40%, 5 ℃ standing 10 hours, collect crystallization, obtaining forulic acid finished product purity is 96.50%, and content yield is 75.23%.
Embodiment 2:
Take bone edge Radix Angelicae Sinensis, after pulverizing, cross 40 mesh sieves, utilize ultrasonic continuous countercurrent extractor to extract, ultrasonic power is 20W, and frequency is 40KHz, extract 80 ℃ of temperature, raw material rate of advance is 10 ms/h, and water flow velocity is 40 ms/h, and aqueous extract is centrifugal with disk plate centrifuge, centrifugate is concentrated into dry under vacuum tightness-0.07Mpa, 55 ℃ of conditions of temperature, obtains enriched material.4 times of amounts (V/W) methyl alcohol stirring and dissolving at 55 ℃ for enriched material, filters and to obtain methyl alcohol filtrate, and the sherwood oil to adding 1 times of volume in methyl alcohol filtrate, stirs 30min under normal temperature, and then standing 60min, collects methanol layer.Methanol layer carries out separation and purification by IV band simulated moving bed chromatography, moving phase is methyl alcohol: water (1% Glacial acetic acid)=70: 30, sample introduction flow velocity is 0.2ml/min, eluent flow rate is 4ml/min, extraction liquid flow velocity is 4ml/min, be 18.5min switching time, chromatographic system service temperature is 25 ℃, the extraction liquid that collection contains forulic acid, being concentrated into solid content is 30%, 0 ℃ standing 5 hours, collect crystallization, obtaining forulic acid finished product purity is 97.14%, and content yield is 77.48%.
Embodiment 3:
Take bone edge Radix Angelicae Sinensis, after pulverizing, cross 10 mesh sieves, utilize ultrasonic continuous countercurrent extractor to extract, ultrasonic power is 100W, and frequency is 100KHz, extract 90 ℃ of temperature, raw material rate of advance is 20 ms/h, and water flow velocity is 60 ms/h, and aqueous extract is centrifugal with tubular-bowl centrifuge, centrifugate is concentrated into dry under vacuum tightness-0.08Mpa, 65 ℃ of conditions of temperature, obtains enriched material.5 times of amounts (V/W) methyl alcohol stirring and dissolving at 50 ℃ for enriched material, filters and to obtain methyl alcohol filtrate, and the sherwood oil to adding 0.4 times of volume in methyl alcohol filtrate, stirs 30min under normal temperature, and then standing 60min, collects methanol layer.Methanol layer carries out separation and purification by IV band simulated moving bed chromatography, moving phase is methyl alcohol: water (1% Glacial acetic acid)=70: 30, sample introduction flow velocity is 0.3ml/min, eluent flow rate is 6ml/min, extraction liquid flow velocity is 6ml/min, be 17.5min switching time, chromatographic system service temperature is 25 ℃, the extraction liquid that collection contains forulic acid, being concentrated into solid content is 50%, 3 ℃ standing 8 hours, collect crystallization, obtaining forulic acid finished product purity is 96.87%, and content yield is 76.66%.
Claims (8)
1. from bone edge Radix Angelicae Sinensis, extract a method for purifying forulic acid, it is characterized in that, comprise following step:
(1) material bone edge Radix Angelicae Sinensis is pulverized, then utilized ultrasonic continuous countercurrent extractor to take hot water and extract as solvent;
(2) the bone edge Radix Angelicae Sinensis aqueous extract that will obtain through step (1) is centrifugal, collects centrifugate;
(3) centrifugate step (2) being obtained is concentrated, obtains enriched material;
(4) enriched material step (3) being obtained is with filtering after dissolve with methanol, removes not tolerantly, obtains methanol solution;
(5) in methanol solution, add sherwood oil, stratification after stirring, collects methanol layer;
(6) adopt simulated moving bed chromatography isolation technique separation and purification forulic acid from methanol layer.
2. a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis according to claim 1, it is characterized in that: in described step (1), material bone edge Radix Angelicae Sinensis powder is broken to 10～40 orders, ultrasonic power 20～200W, range of frequency 10～100KHz, extracting temperature is 60～100 ℃, raw material rate of advance is 5～30 ms/h, water flow velocity is 20～100 ms/h, and raw material working direction is contrary with water (flow) direction.
3. a kind of method of extracting from bone edge Radix Angelicae Sinensis from purifying forulic acid according to claim 1, it is characterized in that: in described step (2), centrifugation apparatus can adopt one or more series connection in tripod pendulum type batch centrifugal, disk plate centrifuge or tubular-bowl centrifuge.
4. a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis according to claim 1, it is characterized in that: in described step (3), adopt vacuum concentration, vacuum tightness is-0.05～-0.09Mpa, thickening temperature is at 55～65 ℃, and in the enriched material obtaining, moisture controlled is in 5%.
5. a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis according to claim 1, is characterized in that: in described step (4), and enriched material: methyl alcohol=1: 1～10 (W/V), temperature range during dissolving is 50～64 ℃.
6. a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis according to claim 1, it is characterized in that: in described step (5), sherwood oil: methanol solution=1: 1～3 (V/V), churning time is not less than 20min, and time of repose is not less than 40min.
7. a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis according to claim 1, it is characterized in that: in described step (6), adopt simulated moving bed chromatography isolation technique separation and purification forulic acid from methanol layer, used simulation moving-bed be IV band structure, by 4～8 C18 chromatographic columns, formed, each band is composed in series by 1～2 root chromatogram column, moving phase is methyl alcohol: water (1% Glacial acetic acid)=70: 30, sample introduction flow velocity is 0.1～0.3ml/min, eluent flow rate is 2～6ml/min, extraction liquid flow velocity is 2～6ml/min, be 17～20min switching time, chromatographic system service temperature is 25 ℃.
8. a kind of method of extracting purifying forulic acid from bone edge Radix Angelicae Sinensis according to claim 1, it is characterized in that: in described step (6), the forulic acid elutriant obtaining is concentrated into solid substance and accounts for 30～50%, then standing 6～10 hours at 0～5 ℃, collect crystallization, obtain high purity forulic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310695017.9A CN103709029B (en) | 2013-12-13 | 2013-12-13 | A kind of technique of extraction purification ferulic acid from Guyuling Capsule |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310695017.9A CN103709029B (en) | 2013-12-13 | 2013-12-13 | A kind of technique of extraction purification ferulic acid from Guyuling Capsule |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103709029A true CN103709029A (en) | 2014-04-09 |
| CN103709029B CN103709029B (en) | 2016-06-29 |
Family
ID=50402422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310695017.9A Active CN103709029B (en) | 2013-12-13 | 2013-12-13 | A kind of technique of extraction purification ferulic acid from Guyuling Capsule |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103709029B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104117044A (en) * | 2014-07-25 | 2014-10-29 | 河南科技大学第一附属医院 | Preparation method of traditional Chinese medicine (TCM) decoction for treating constipation |
| CN104127844A (en) * | 2014-07-25 | 2014-11-05 | 河南科技大学第一附属医院 | Preparation method for traditional Chinese medicine preparation used for treating senile constipation |
| CN107652179A (en) * | 2017-10-31 | 2018-02-02 | 桂林纽泰生物科技有限公司 | A kind of method that forulic acid is extracted from Desmodium styracifolium |
| CN110812428A (en) * | 2019-10-14 | 2020-02-21 | 中山市恒生药业有限公司 | Guiqi blood nourishing oral liquid and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1064674A (en) * | 1991-03-13 | 1992-09-23 | 筑野食品工业株式会社 | The preparation method of forulic acid |
| CN101143816A (en) * | 2007-10-23 | 2008-03-19 | 天津理工大学 | Method for extracting ferulic acid from Chinese angelica by ultrasonic |
| CN101768073A (en) * | 2010-02-01 | 2010-07-07 | 南京泽朗医药科技有限公司 | Method for preparing ferulic acid from Chinese angelica |
| CN102060693A (en) * | 2010-12-20 | 2011-05-18 | 大兴安岭嘉迪欧营养原料有限公司 | Method for enriching and purifying ferulic acid in cimicifugae foetidae |
| CN102381962A (en) * | 2011-10-19 | 2012-03-21 | 兰州理工大学 | Extraction method of effective components of Chinese angelica |
-
2013
- 2013-12-13 CN CN201310695017.9A patent/CN103709029B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1064674A (en) * | 1991-03-13 | 1992-09-23 | 筑野食品工业株式会社 | The preparation method of forulic acid |
| CN101143816A (en) * | 2007-10-23 | 2008-03-19 | 天津理工大学 | Method for extracting ferulic acid from Chinese angelica by ultrasonic |
| CN101768073A (en) * | 2010-02-01 | 2010-07-07 | 南京泽朗医药科技有限公司 | Method for preparing ferulic acid from Chinese angelica |
| CN102060693A (en) * | 2010-12-20 | 2011-05-18 | 大兴安岭嘉迪欧营养原料有限公司 | Method for enriching and purifying ferulic acid in cimicifugae foetidae |
| CN102381962A (en) * | 2011-10-19 | 2012-03-21 | 兰州理工大学 | Extraction method of effective components of Chinese angelica |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104117044A (en) * | 2014-07-25 | 2014-10-29 | 河南科技大学第一附属医院 | Preparation method of traditional Chinese medicine (TCM) decoction for treating constipation |
| CN104127844A (en) * | 2014-07-25 | 2014-11-05 | 河南科技大学第一附属医院 | Preparation method for traditional Chinese medicine preparation used for treating senile constipation |
| CN107652179A (en) * | 2017-10-31 | 2018-02-02 | 桂林纽泰生物科技有限公司 | A kind of method that forulic acid is extracted from Desmodium styracifolium |
| CN110812428A (en) * | 2019-10-14 | 2020-02-21 | 中山市恒生药业有限公司 | Guiqi blood nourishing oral liquid and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103709029B (en) | 2016-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101829210B (en) | Method for preparing apple polyphenol | |
| CN102199177A (en) | Manufacturing method of pure natural high-purity stevioside | |
| CN103709029A (en) | Process for extracting and purifying ferulic acid from angelica cartilaginomarginata Nakai | |
| CN103408538B (en) | Method for extracting silymarin | |
| CN103570779A (en) | Method for preparing glycyrrhizin by simulated moving bed separation | |
| CN102106928B (en) | Method for preparing high-purity oil tea saponins | |
| CN107325138A (en) | A kind of method of the main anthocyanin of four kinds of extraction separation and purification in pomace from blackcurrant | |
| CN105232679A (en) | Method for simultaneously extracting ursolic acid and oleanolic acid in hawthorn by means of subcritical water | |
| CN104610417A (en) | Method for extracting ursolic acid and oleanolic acid from hawthorns | |
| CN107098942A (en) | A kind of method of kaempferia galamga glycosides in Subcritical Water Extraction radish leaves | |
| CN104447941A (en) | Method for simultaneous extraction of oligomeric proanthocyanidins and tea saponin from camellia oleifera shells | |
| CN103694213B (en) | A kind of extraction and isolation preparation method of Lignans in Schisandra chinensis monomer | |
| CN103709217B (en) | A kind of method preparing luteoloside from Radix Achyranthis Bidentatae rattan | |
| CN104263763A (en) | Novel method for extracting resveratrol from giant knotweed | |
| CN104610418B (en) | A kind of method extracting ursolic acid from Herba Cynomorii | |
| CN103833805A (en) | Process for refining glycyrrhizinic acid in liquorice | |
| CN105503981A (en) | Method for extracting and separating anthocyanin from red cabbage | |
| CN102327325A (en) | Method for preparing white mulberry rootbark general flavone | |
| CN103524342A (en) | Method for rapidly separating tussilagone by adopting adjustable ternary solvent system | |
| CN102731309B (en) | A kind of method extracting separating chlorogenic acid from Herba Dendranthematis indici | |
| CN102633860A (en) | Method for extracting ardisiacrispin A | |
| CN105713006A (en) | Preparation method of oridonin | |
| CN103893228B (en) | The method preparing osthole from Radix Angelicae Pubescentis | |
| CN204637640U (en) | A kind of device extracting mogroside V from Momordica grosvenori | |
| CN103242397A (en) | Method for preparing leonurus glycoside from radix rehmanniae |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20181113 Address after: 161099 No. 92 Longhua Road, Tiefeng District, Qiqihar City, Heilongjiang Province Patentee after: Heilongjiang dinghengsheng Pharmaceutical Co. Ltd. Address before: 165000 Heilongjiang Jiagedaqi Changhong community Xinyuan District AGA Road North Lin Bei Bei group Patentee before: Daxinganling Gadol Sports Ingredient Co., Ltd. |