CN101891608A - Method for preparing ferulic acid by separation - Google Patents
Method for preparing ferulic acid by separation Download PDFInfo
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- CN101891608A CN101891608A CN2010102186543A CN201010218654A CN101891608A CN 101891608 A CN101891608 A CN 101891608A CN 2010102186543 A CN2010102186543 A CN 2010102186543A CN 201010218654 A CN201010218654 A CN 201010218654A CN 101891608 A CN101891608 A CN 101891608A
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Abstract
The invention relates to a method for preparing ferulic acid by separation. The method prepares the high-purity ferulic acid by separation from ethanol ultrasonic extract of Szechuan lovage rhizome plant by adopting countercurrent chromatography. A solvent consists of four components, namely ether or n-alkane, fatty ester, acetonitrile or fatty alcohol or fatty ketone and water or acid-containing water in a volume ratio of (0.2-1.25): (1-3): 1: (1-3) in turn, and the solvent contains 0.1 to 0.5 percent (V/V) of acid. The method is suitable for preparing the monomer ferulic acid by separation of countercurrent chromatographs of various types, and can directly introduce a large amount of crude mixture; and the separation purity can reach over 95 percent.
Description
Technical field
The present invention relates to a kind ofly adopt high-speed countercurrent chromatography from the ethanol ultrasonic extraction thing of Chinese medicine Ligusticum wallichii, to separate to prepare the high-purity monomer method for preparing ferulic acid by separation.
Background technology
Ligusticum wallichii is a samphire, the dry rhizome of Ligusticum wallichii [Ligusticum chuanxiong Hort.], and warm in nature, flavor suffering has the function of blood-activating and qi-promoting, wind-expelling pain-stopping.Ligusticum wallichii is the traditional Chinese medicine of China, in China long medicinal history is arranged, and the successive dynasties medical expert all is used for menoxenia, dysmenorrhoea amenorrhoea due to the blood stasis stagnation of the circulation of vital energy to it, stagnation of QI due to depression of the liver and cause the pain in chest and hypochondrium of hematogenous blockage, arthralgia due to wind-cold-dampness pathogen BI syndrome, treating swelling and pain by traumatic injury, headache, rheumatalgia.In recent years, clinically be usually used in treating coronary heart disease, stenocardia, cardiovascular disorder and gynaecopathias such as ischemic cerebrovascular disease.Contain multiple compositions such as volatile oil, lactone, alkaloids, phenols in the Ligusticum wallichii.Wherein, alkaloids and phenolic acids are main active ingredient promoting blood circulation and removing blood stasis, but alkaloid is low.And liposoluble ingredient mainly is a forulic acid.But the forulic acid anticoagulant promotes the thrombocyte depolymerization. antithrombotic forms, and removes vascular smooth muscle spasm, anti-oxidant and raising membrane stability.There are anti-inflammatory, analgesia, antifertility, ultra-violet radiation resisting and Green Tea Extract, adjusting immunologic function, sharp liver to protect pharmacological actions such as courage.The content of forulic acid in Ligusticum wallichii is about 0.1%.The extraction of effective constituent has supercritical fluid extraction, alcohol extracting, two carry etc. in the Ligusticum wallichii, and products therefrom is the mixture of Ligustrazine, forulic acid, volatile oil.
Existing bibliographical information adopts the method for column chromatography and high performance liquid chromatography to separate, through the D101 macroporous resin column, carbon 18 posts, separate to obtain forulic acid the crude product behind extraction using alcohol, perhaps adopt the alkaline ethanol refluxing extraction after, hcl acidifying, separate through a plurality of steps such as repeated multiple times extracted with diethyl ether, yellow soda ash extraction, centrifugation again and obtain forulic acid, technology is loaded down with trivial details, the cost height, and the rate of recovery is low.The adverse current chromatogram method for separating and preparing can reach high purity, low cost, rate of recovery height is better than traditional column chromatography and high performance liquid chromatography separation method both ways, there is not on the one hand solid state adhesion body not have the irreversible adsorption loss, on the other hand the direct upper prop of crude product.Because high speed adverse current chromatogram (High-speed CountercurrentChromatography, HSCCC) be that a kind of successive that grew up in recent years need not the efficient of any solid support, liquid liquid distribution chromatography isolation technique fast, variety of issue-sample that it has avoided solid state adhesion body or carrier to bring easily is adsorbed, loss and sex change, when using other liquid phase chromatography amount of being prepared to separate, its allocative efficiency can obviously reduce, solvent-oil ratio is big, HSCCC guarantees higher peak type resolution, fractional dose is big, the sample free of losses, rate of recovery height, isolating environment relaxes, and saves solvent.Counter current chromatograph can directly advance the product mixture that slightly gets sample in a large number, and separating resulting can reach quite high purity, even can directly connect instruments such as mass spectrograph, has been widely used in the preparation separation and the purifying of field chemical substances such as biology, medicine, environmental protection.
Summary of the invention
The objective of the invention is to adopt the method for high speed adverse current chromatogram to obtain the forulic acid monomer of purity more than 95%.
The solution of the present invention is: the Ligusticum wallichii crude product raw material of ethanol ultrasonic extraction separates preparation high purity forulic acid by counter current chromatography.The two-phase system of selecting for use is an aqueous solvent system.Aqueous solvent system is made of four components, and the A component is ethers or normal paraffin; The B component is a fatty ester; The C component is acetonitrile, Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketone; The D component is water or acidiferous water.
Normal paraffin is normal hexane, normal heptane, Skellysolve A.
Fatty ester is ethyl acetate, propyl acetate, isopropyl acetate or n-butyl acetate.
Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketone are methyl alcohol, ethanol or acetone.
Ethers is ether, sherwood oil or methyl tertiary butyl ether.
Acid is trifluoroacetic acid, acetate or formic acid.
Adopt aqueous solvent system, below be stationary phase mutually, be moving phase mutually down, under guaranteeing that phase volume ratio is less than 1 prerequisite up and down, according to solubility constant, do not destroying under the system equilibrated situation, regulating the volume ratio of A: B: C: D four components: (0.2-1.25): (1-3): 1: (1-3) contain sour 0.1%-0.5% (V/V), obtain forulic acid through a counter-current separation.
Experiment condition is fit to room temperature 15-35 ℃, and room temperature is little to the separation efficiency influence.In the said temperature scope, when room temperature was higher, appearance time slightly shifted to an earlier date, and separation efficiency changes little, and the forulic acid peak shape is not had influence.
At first by volume above-mentioned solvent system is disposed in the separating funnel, shakes up the back standing demix.Ready to balance after for some time separates upper and lower phase.Adopt half preparation type or analysis mode high-speed counter-current chromatograph, be furnished with the NS-1007 pump, 20mL or 2ml sampling valve, tetrafluoroethylene post, column volume are 240mL or 500ml or 40ml, 8823A-UV UV-detector, Yoko gawa 3057 potable recording instrument.Be dissolved in the moving phase Ligusticum wallichii crude extract stand-by.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 500-1000rpm, with the flow velocity of 0.5-3.0mL/min moving phase is pumped in the post, treat that whole system is set up running balance after, by the sampling valve sample introduction; According to the detector uv atlas, the receiving target composition obtains solid then.
Its purity of forulic acid of extracting with present method can reach more than 95%.The counter current chromatograph that is applicable to various models separates preparation forulic acid monomer, can directly advance the product mixture that slightly gets sample in a large number, and separating resulting can reach quite high purity.
Embodiment
Embodiment 1:
Choose normal hexane-ethyl acetate-methanol-water (containing trifluoroacetic acid) separation and purification Rhizoma Chuanxiong extract (the Ligusticum wallichii raw material of ethanol ultrasonic extraction) on half preparation type counter current chromatograph GS10A, at first by 0.6: 1.4: 1: 1 (containing 0.1% trifluoroacetic acid), volume ratio was disposed at above-mentioned solvent composition in the separating funnel, shook up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii material dissolution that takes by weighing the 300mg ethanol ultrasonic extraction is stand-by in 20mL moving phase.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 500rpm, with the flow velocity of 0.8mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 98%.
Embodiment 2:
Choose sherwood oil-n-butyl acetate-alcohol-water and on half preparation type counter current chromatograph EMC500, separate Rhizoma Chuanxiong extract.Earlier by 0.3: 3: 1: 1.25 volume ratios are disposed at above-mentioned solvent composition in the separating funnel, shake up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 500mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii dissolving crude product that takes by weighing the 700mg ethanol ultrasonic extraction is stand-by in 20mL moving phase, before the sample introduction, earlier is filled with whole pillar with stationary phase, and the adjustment engine speed is 1000rpm, with the flow velocity of 3.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 95%.
Embodiment 3:
Get normal heptane-propyl acetate-methanol-water (containing acetate) component and on analysis mode counter current chromatograph GS20A, separate Rhizoma Chuanxiong extract.At first by 0.25: 1.6: 1: 1 (containing 0.5% acetate), volume ratio was disposed at above-mentioned solvent composition in the separating funnel, shook up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt analysis mode counter current chromatograph GS20A, be furnished with the NS-1007 pump, the 2mL sampling valve, tetrafluoroethylene post, column volume are 40mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii dissolving crude product that takes by weighing the 20mg ethanol ultrasonic extraction is stand-by in 2mL moving phase.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 1000rpm, with the flow velocity of 0.5mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches more than 96%.
Embodiment 4:
Choose Skellysolve A-isopropyl acetate-acetonitrile-water and separate Rhizoma Chuanxiong extract on half preparation type counter current chromatograph GS10AB, at first by 1.25: 3: 1: 3 volume ratios are disposed at above-mentioned solvent composition in the separating funnel, shake up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii dissolving crude product that takes by weighing the 490mg ethanol ultrasonic extraction is stand-by in 20mL moving phase.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 700rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 97%.
Embodiment 5:
Choose normal hexane-ethyl acetate-acetone-water (containing formic acid) and on half preparation type counter current chromatograph GS10A, separate Rhizoma Chuanxiong extract.At first by 1: 1.5: 1: 1.2 (containing 0.3% formic acid), volume ratio was disposed at above-mentioned solvent composition in the separating funnel, shook up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii that takes by weighing the 430mg extraction using alcohol is dissolved in the 20mL moving phase stand-by.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 800rpm, with the flow velocity of 1.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 96%.
Embodiment 6:
Choose sherwood oil-isopropyl acetate-acetonitrile-water and separate Rhizoma Chuanxiong extract on half preparation type counter current chromatograph EMC500, at first by 0.3: 1.7: 1: 1.3 volume ratios are disposed at above-mentioned solvent composition in the separating funnel, shake up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 500mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii that takes by weighing the 590mg extraction using alcohol is dissolved in the 20mL moving phase stand-by.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 97%.
Embodiment 7:
Choose sherwood oil-n-butyl acetate-alcohol-water and separate Rhizoma Chuanxiong extract on half preparation type counter current chromatograph GS10A, at first by 1: 1: 1: 1 volume ratio is disposed at above-mentioned solvent composition in the separating funnel, shakes up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa3057 potable recording instrument.The Ligusticum wallichii that takes by weighing the 400mg ethanol ultrasonic extraction is dissolved in the 20mL moving phase stand-by.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 96%.
Embodiment 8:
Choose normal hexane-ethyl acetate-acetone-water (containing acetate) and on half preparation type counter current chromatograph GS10A, separate Rhizoma Chuanxiong extract.At first by 0.2: 1: 1: 1 (containing 0.3% acetate), volume ratio was disposed at above-mentioned solvent composition in the separating funnel, shook up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii that takes by weighing the 350mg extraction using alcohol is dissolved in the 20mL moving phase stand-by.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 800rpm, with the flow velocity of 1.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 96%.
Embodiment 9:
Choose normal hexane-ethyl acetate-acetonitrile-water (containing trifluoroacetic acid) and on half preparation type counter current chromatograph EMC500, separate Rhizoma Chuanxiong extract, at first by 0.2: 1.8: 1: 1 (containing 0.25% trifluoroacetic acid), volume ratio was disposed at above-mentioned solvent composition in the separating funnel, shook up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 500mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii that takes by weighing the 380mg ethanol ultrasonic extraction is dissolved in the 20mL moving phase stand-by.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 96%.
Embodiment 10:
Choose normal heptane-propyl acetate-acetone-water (containing trifluoroacetic acid) and on half preparation type counter current chromatograph GS10A, separate Rhizoma Chuanxiong extract, at first by 1.25: 1.25: 1: 1.5 (containing 0.4% trifluoroacetic acid), volume ratio was disposed at above-mentioned solvent composition in the separating funnel, shook up the back standing demix.Ready to balance after for some time separates upper and lower phase, takes off as stationary phase, and is last as moving phase.Adopt half countercurrent chromatography instrument, be furnished with the NS-1007 pump, the 20mL sampling valve, tetrafluoroethylene post, column volume are 240mL, 8823A-UV UV-detector, Yokogawa 3057 potable recording instrument.The Ligusticum wallichii that takes by weighing the 380mg ethanol ultrasonic extraction is dissolved in the 20mL moving phase stand-by.Before the sample introduction, earlier be filled with whole pillar with stationary phase, the adjustment engine speed is 800rpm, with the flow velocity of 2.0mL/min moving phase is pumped in the post; After treating that whole system is set up running balance, by the sampling valve sample introduction; Then according to the detector uv atlas, the receiving target composition, its HPLC purity reaches about 96%.
Claims (6)
1. method for preparing ferulic acid by separation is characterized in that: it is to adopt counter current chromatography to separate from plant Ligusticum wallichii ethanol ultrasonic extraction thing to prepare the high purity forulic acid, and its solvent composition is made of four components of ABCD:
The A component is ethers or normal paraffin; The B component is a fatty ester; The C component is acetonitrile, Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketone; The D component is water or acidiferous water; Be followed successively by by volume: (0.2-1.25): (1-3): 1: (1-3), acidiferous water contains sour 0.1%-0.5% by volume.
2. a kind of method for preparing ferulic acid by separation according to claim 1 is characterized in that: normal paraffin is normal hexane, normal heptane or Skellysolve A.
3. a kind of method for preparing ferulic acid by separation according to claim 1 is characterized in that: Fatty Alcohol(C12-C14 and C12-C18) or aliphatic ketone are: methyl alcohol, ethanol or acetone.
4. a kind of method for preparing ferulic acid by separation according to claim 1 is characterized in that: fatty ester is ethyl acetate, propyl acetate, isopropyl acetate or n-butyl acetate.
5. a kind of method for preparing ferulic acid by separation according to claim 1 is characterized in that: ethers is ether, sherwood oil or methyl tertiary butyl ether.
6. a kind of method for preparing ferulic acid by separation according to claim 1 is characterized in that: acid is trifluoroacetic acid, acetate or formic acid.
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| CN2010102186543A CN101891608A (en) | 2010-07-06 | 2010-07-06 | Method for preparing ferulic acid by separation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107011158A (en) * | 2017-04-06 | 2017-08-04 | 成都众宜坊农业开发有限公司 | A kind of method of extraction purification forulic acid in cauline leaf from Ligusticum wallichii |
| CN110857271A (en) * | 2018-08-24 | 2020-03-03 | 江苏康缘药业股份有限公司 | Compound and preparation method and application thereof |
-
2010
- 2010-07-06 CN CN2010102186543A patent/CN101891608A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 胡佳 等: "高速逆流色谱分离纯化川芎中的阿魏酸", 《全国生物医药色谱学术交流会（2010景德镇）论文集》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107011158A (en) * | 2017-04-06 | 2017-08-04 | 成都众宜坊农业开发有限公司 | A kind of method of extraction purification forulic acid in cauline leaf from Ligusticum wallichii |
| CN110857271A (en) * | 2018-08-24 | 2020-03-03 | 江苏康缘药业股份有限公司 | Compound and preparation method and application thereof |
| CN110857271B (en) * | 2018-08-24 | 2021-06-01 | 江苏康缘药业股份有限公司 | Compound and preparation method and application thereof |
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Application publication date: 20101124 |