CN110818547B - A method for extracting curcumin and gingerol from rhizoma Zingiberis recens - Google Patents
A method for extracting curcumin and gingerol from rhizoma Zingiberis recens Download PDFInfo
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Abstract
The invention discloses a preparation method for extracting curcumin and gingerol from ginger, which comprises the following steps: s1, washing ginger and stirring with ethanol to form slurry; s2, adding ethanol, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazolium tetrafluoroborate, pressurizing the mixture to extract by a solvent, filtering the mixture, and performing ultrafiltration to obtain an ultrafiltration membrane filtering solution; s3, preparing a molecularly imprinted polymer by taking curcumin and gingerol as double-template molecules; s4, mixing the molecularly imprinted polymer and the filtering solution, loading the mixture to a column, washing the mixture by 30-50% of ethanol to obtain gingerol, eluting the gingerol by 70-90% of ethanol, and washing the eluted gingerol to obtain curcumin.
Description
Technical Field
The invention belongs to the field of medical industry, and particularly relates to a preparation method for extracting curcumin and gingerol from ginger.
Background
Ginger (ginger)Zingber officinale Roscoe) The raw ginger and bai la yun belong to the perennial root herbaceous plants of the Zingiberaceae family, and are the rhizomes of the plants of the Zingiberaceae family. Besides being widely used as spice seasoning, ginger is also a common traditional Chinese medicine and has the effects of relieving exterior syndrome, dispelling cold, warming middle energizer, relieving vomiting, warming lung, relieving cough and detoxifying.
Modern medical research proves that the effective components in ginger mainly comprise curcumin and gingerol. Wherein curcumin is a very rare pigment with diketone in plant world, and has pharmacological effects of reducing blood sugar, reducing blood fat, resisting oxidation, resisting inflammation, resisting cancer and the like; gingerol is the main flavor substance with characteristic spicy flavor in ginger, and can clear free radical, oxidation resistance, mutation resistance, tumor resistance, bacteria resistance, virus resistance and immunity regulation.
Because the difference of the physical and chemical properties of curcumin and gingerol is large, the prior art still adopts different extraction methods to respectively extract two monomers, the single extraction method has high components, and two high-purity products cannot be obtained at one time, and CN103012095A discloses a method for jointly extracting a plurality of ginger functional components, curcumin and gingerol are obtained by using organic solvent extraction and vacuum rotary evaporation, but the yield of the method is reduced, the purity of the obtained product is not high, and the utilization rate of raw materials is relatively low.
Therefore, there is still a need to develop a preparation method with higher extraction efficiency and capable of simultaneously extracting high-purity curcumin and gingerol, improving the utilization rate of raw materials, improving the technical level of ginger extraction and improving the product quality.
Disclosure of Invention
In order to solve the technical problems, the invention provides the preparation method for extracting the curcumin and the gingerol from the ginger, and the preparation method has the advantages of higher yield, higher product purity, simple preparation method, easy operation and suitability for industrial mass production.
The technical scheme adopted by the invention for solving the technical problems is as follows:
the invention provides a preparation method for extracting curcumin and gingerol from ginger, which comprises the following steps:
s1, cleaning ginger, adding 50% ethanol, wherein the weight ratio of the ginger to the 50% ethanol is 1: 3-4, and stirring to form slurry;
s2, adding 95% ethanol into the slurry prepared in S1 to enable the concentration of the ethanol in the slurry to be 70%, then adding N, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazole tetrafluoroborate, uniformly stirring, extracting by adopting a pressurized solvent extraction technology, filtering an extracting solution, collecting a supernatant, and performing ultrafiltration circulation to obtain an ultrafiltration membrane filtering solution;
s3, dissolving curcumin and gingerol serving as double-template molecules in acetonitrile, adding 4-vinylpyridine serving as a functional monomer, shaking for 30min, adding a cross-linking agent ethylene glycol dimethacrylate and an initiator dibenzoyl peroxide, uniformly mixing, reacting for 24h at 80 ℃ to obtain a block polymer, crushing, sieving and drying to obtain the molecularly imprinted polymer;
s4, mixing the molecularly imprinted polymer obtained in the S3 and the ultrafiltration membrane filtering solution obtained in the S2, loading the mixture on a column, washing the column with 30-50% ethanol, evaporating the solvent by using a washing solution to obtain gingerol, eluting the gingerol with 70-90% ethanol, and evaporating the solvent by using an eluent to obtain curcumin.
In a preferred embodiment of the present invention, in the step S2, the weight ratio of ginger, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazolium tetrafluoroborate is 1:0.2 to 0.5:0.5 to 0.8.
In a preferred embodiment of the present invention, in the step S2, the weight ratio of N-dimethyl-N- (2-hydroxy-ethoxyethyl) propanoic acid ammonium to 1-butyl-3-methylimidazolium tetrafluoroborate is 1: 1.2.
In a preferred embodiment of the present invention, in the step S2, the extraction temperature is 80 ℃, the extraction time is 10min, the extraction pressure is 8MPa, and the displacement volume is 40%.
In a preferred embodiment of the present invention, in the step S3, the molar ratio of the template molecules curcumin to gingerol is 2: 3.
In a preferred embodiment of the present invention, in the step S3, the molar ratio of the total template molecules, the functional monomer and the cross-linking agent is 1:5 to 8:8 to 10.
As a preferred embodiment of the present invention, the gingerol obtained in S4, wherein the content of 6-gingerol is greater than 85%.
Compared with the prior art, the invention has the beneficial technical effects that:
1. the method takes ethanol, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazolium tetrafluoroborate with proper concentrations as composite solvents, increases the extraction efficiency of curcumin and gingerol in ginger, reduces the extraction of other non-target products, combines a pressurized solvent extraction technology, is beneficial to the separation of effective components, shortens the extraction time, avoids long-time high-temperature treatment, and can effectively protect the target products from being damaged.
2. The invention creatively prepares the double-template molecularly imprinted polymer capable of effectively adsorbing curcumin and gingerol by adopting a double-template molecularly imprinted technology, and keeps effective difference of adsorption force of two molecules, so that two components can be eluted by different solvents, and the separation and purification of curcumin and gingerol are realized.
3. In the extraction process, toxic reagents such as methanol, benzene and the like are avoided, and the prepared product has high purity, no harmful solvent residue and safer and more convenient use.
Detailed Description
The invention is further illustrated by the following comparative examples and preferred examples. It should not be understood that the scope of the above-described subject matter of the present invention is limited to the following specific examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Unless otherwise indicated, the raw materials and equipment described in the embodiments of the present invention are known products and can be obtained by purchasing commercially available products.
Comparative example 1
Curcumin and gingerol were prepared as described in the CN103012095A example.
Cleaning rhizoma Zingiberis recens, cutting, adding 3 times of anhydrous ethanol, pulping, centrifuging at 5000rpm for 10min to obtain supernatant, vacuum rotary evaporating the supernatant at 60 deg.C and 40rpm, rotary evaporating in water bath to volatilize ethanol to obtain paste gingerol, and drying the concentrated solution to obtain powdered curcumin product. After the finished product is weighed, the yield of the gingerol is calculated to be 3.12 per mill, the yield of the curcumin is 3.76 per mill, and the purity of the gingerol is 50.7 percent and the purity of the curcumin is 42.4 percent through inspection.
Comparative example 2
Curcumin and gingerol were prepared as follows.
S1, cleaning ginger, and pulping with 5 times of absolute ethyl alcohol;
s2, adding 1-alkyl-3-methylimidazole and 1-alkylpyridine which are 0.5 time and 0.3 time of the weight of ginger into the slurry, extracting by a pressurized solvent extraction technology at 80 ℃ for 20min under the extraction pressure of 8MPa and the displacement volume of 40%, filtering the extracting solution, collecting the supernatant, and performing ultrafiltration circulation to obtain an ultrafiltration membrane filtering solution;
s3, mixing the filtrate with macroporous adsorbent resin and ultrafiltration membrane, loading onto column, washing with 30% methanol, evaporating solvent from the washing solution to obtain gingerol, eluting with 70% ethanol, and evaporating solvent from the eluate to obtain curcumin. After the finished product is weighed, the yield of the gingerol is calculated to be 3.85 per mill, the yield of the curcumin is 4.13 per mill, and the inspection shows that the purity of the gingerol is 52.7 percent and the purity of the curcumin is 56.8 percent.
Comparative example 3
Curcumin and gingerol were prepared as follows.
S1, cleaning ginger, adding 50% ethanol, wherein the weight ratio of ginger to 50% ethanol is 1:4, and stirring to form slurry;
s2, adding 95% ethanol into the slurry prepared in S1 to enable the concentration of the ethanol in the slurry to be 70%, then adding 1-alkyl-3-methylimidazole and 1-alkylpyridine, wherein the weight ratio of the ginger to the 1-alkyl-3-methylimidazole to the 1-alkylpyridine is 1:0.4:0.5, uniformly stirring, extracting by adopting a pressurized solvent extraction technology, filtering the extracting solution, collecting the supernatant, and performing ultrafiltration circulation to obtain an ultrafiltration membrane filtering solution;
s3, mixing the filtrate with macroporous adsorbent resin and ultrafiltration membrane, loading onto column, washing with 30% ethanol, evaporating solvent from washing solution to obtain gingerol, eluting with ethyl acetate, evaporating solvent from eluent to obtain curcumin, weighing the product, calculating to obtain gingerol yield of 4.18 ‰, curcumin yield of 4.73 ‰, and detecting to obtain gingerol with purity of 62.5% and curcumin purity of 50.1%.
Comparative example 4
Curcumin and gingerol were prepared as follows.
S1, cleaning ginger, adding 50% ethanol, wherein the weight ratio of ginger to 50% ethanol is 1:4, and stirring to form slurry;
s2, adding 95% ethanol into the slurry prepared in S1 to enable the concentration of the ethanol in the slurry to be 70%, then adding 1-alkyl-3-methylimidazole and 1-alkylpyridine, wherein the weight ratio of the ginger to the 1-alkyl-3-methylimidazole to the 1-alkylpyridine is 1:0.4:0.5, uniformly stirring, extracting by adopting a pressurized solvent extraction technology, filtering the extracting solution, collecting the supernatant, and performing ultrafiltration circulation to obtain an ultrafiltration membrane filtering solution;
s3, dissolving curcumin serving as a template molecule in acetonitrile, adding methacrylic acid serving as a functional monomer, oscillating for 30min, adding a crosslinking agent ethylene glycol dimethacrylate and an initiator azobisisobutyronitrile, wherein the molar ratio of the template molecule to the functional monomer to the crosslinking agent is 1:5:10, the weight of the initiator is the same as that of ginger, uniformly mixing, reacting for 24h at 70 ℃ to obtain a block polymer, crushing, sieving and drying to obtain the molecularly imprinted polymer;
s4, mixing the molecularly imprinted polymer obtained in the step S3 and the ultrafiltration membrane filtering solution obtained in the step S2, loading the mixture on a column, washing the column with water, evaporating the solvent by using a washing solution to obtain gingerol, eluting the gingerol by using absolute ethyl alcohol, and evaporating the solvent by using an eluent to obtain curcumin. The yield of gingerol is 4.52 per mill and the yield of curcumin is 5.38 per mill after the finished product is weighed, and the purity of gingerol is 55.6 percent and the purity of curcumin is 57.3 percent through inspection.
Example 1
Curcumin and gingerol were prepared as follows.
S1, cleaning ginger, adding 50% ethanol, wherein the weight ratio of ginger to 50% ethanol is 1:4, and stirring to form slurry;
s2, adding 95% ethanol into the slurry prepared in S1 to enable the ethanol concentration in the slurry to be 70%, then adding N, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazole tetrafluoroborate, uniformly stirring ginger, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazole tetrafluoroborate in a weight ratio of 1:0.5:1, extracting by adopting a pressurized solvent extraction technology, filtering the extracting solution, wherein the extraction temperature is 80 ℃, the extraction time is 10min, the extraction pressure is 8MPa, the displacement volume is 40%, collecting the supernatant, and performing ultrafiltration circulation to obtain an ultrafiltration filtering solution;
s3, dissolving curcumin and gingerol serving as double-template molecules in a molar ratio of 1:1 in acetonitrile, adding 4-vinylpyridine serving as a functional monomer, shaking for 30min, adding a crosslinking agent ethylene glycol dimethacrylate and an initiator dibenzoyl peroxide, mixing uniformly, reacting at 80 ℃ for 24h to obtain a block polymer, crushing, sieving and drying to obtain the molecularly imprinted polymer, wherein the molar ratio of the template molecules to the functional monomer to the crosslinking agent is 1:8:10, and the weight of the initiator is 1/2 of that of ginger;
s4, mixing the molecularly imprinted polymer obtained in S3 and the ultrafiltration membrane filtered solution obtained in S2, loading the mixture on a column, washing the column with 30% ethanol, evaporating the solvent in a washing solution to obtain gingerol, eluting the gingerol with 90% ethanol, and evaporating the solvent in an eluent to obtain curcumin. The yield of gingerol is 8.86 per mill and the yield of curcumin is 8.31 per mill after the finished product is weighed, the purity of gingerol is 80.7 percent through inspection, wherein the content of 6-gingerol is 69.1 percent, the purity of curcumin is 82.5 percent,
example 2
Curcumin and gingerol were prepared as described in example 1. The difference lies in that: in S2, the weight ratio of ginger, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazolium tetrafluoroborate is 1:0.5: 0.6; s3, the molar ratio of the middle template molecule curcumin to the gingerol is 2: 3; the yield of gingerol is 9.43 per mill and the yield of curcumin is 8.66 per mill after the finished product is weighed, and the purity of gingerol is 83.1 percent through inspection, wherein the content of 6-gingerol is 86.7 percent, and the purity of curcumin is 86.2 percent.
The above description is only a preferred embodiment of the present invention, and it should be understood that the present invention is not limited to the above description, which should be interpreted as a limitation, since modifications can be made to the embodiment and its application range by those skilled in the art in light of the above description.
Claims (7)
1. A preparation method for extracting curcumin and gingerol from ginger is characterized by comprising the following steps:
s1, cleaning ginger, adding 50% ethanol, wherein the weight ratio of the ginger to the 50% ethanol is 1: 3-4, and stirring to form slurry;
s2, adding 95% ethanol into the slurry prepared in S1 to enable the concentration of the ethanol in the slurry to be 70%, then adding N, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazole tetrafluoroborate, uniformly stirring, extracting by adopting a pressurized solvent extraction technology, filtering an extracting solution, collecting a supernatant, and performing ultrafiltration circulation to obtain an ultrafiltration membrane filtering solution;
s3, dissolving curcumin and gingerol serving as double-template molecules in acetonitrile, adding 4-vinylpyridine serving as a functional monomer, oscillating for 30min, adding a crosslinking agent ethylene glycol dimethacrylate and an initiator dibenzoyl peroxide, uniformly mixing, reacting for 24h at 80 ℃ to obtain a block polymer, crushing, sieving and drying to obtain a molecularly imprinted polymer;
s4, mixing the molecularly imprinted polymer obtained in the S3 and the ultrafiltration membrane filtering solution obtained in the S2, loading the mixture on a column, washing the column with 30-50% ethanol, evaporating the solvent by using a washing solution to obtain gingerol, eluting the gingerol with 70-90% ethanol, and evaporating the solvent by using an eluent to obtain curcumin.
2. The method as claimed in claim 1, wherein in step S2, the weight ratio of rhizoma Zingiberis recens, N-dimethyl-N- (2-hydroxy-ethoxyethyl) ammonium propionate and 1-butyl-3-methylimidazolium tetrafluoroborate is 1: 0.2-0.5: 0.5-0.8.
3. The method as claimed in claim 1, wherein in step S2, the weight ratio of ammonium N, N-dimethyl-N- (2-hydroxy-ethoxyethyl) propionate to 1-butyl-3-methylimidazolium tetrafluoroborate is 1: 1.2.
4. The method as claimed in claim 1, wherein the pressure solvent extraction technique adopted in step S2 comprises extracting at 80 deg.C for 10min under 8MPa for 40% of displacement volume.
5. The method as claimed in claim 1, wherein in step S3, the molar ratio of the template molecules curcumin to gingerol is 2: 3.
6. The method for extracting curcumin and gingerol from ginger according to claim 1, wherein in the step S3, the molar ratio of the total amount of template molecules, the functional monomer and the cross-linking agent is 1: 5-8: 8-10.
7. The method according to claim 1, wherein the gingerol obtained in S4 contains 6-gingerol more than 85%.
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| CN101381430A (en) * | 2008-10-09 | 2009-03-11 | 浙江工业大学 | Molecule brand polymer of curcumin, preparation method and application thereof |
| CN103012095A (en) * | 2012-12-06 | 2013-04-03 | 山东农业大学 | Method for combined extraction of variety of functional components of ginger |
| CN104277177A (en) * | 2014-10-28 | 2015-01-14 | 山东省分析测试中心 | Gingerol pseudo-template molecularly imprinted polymer and method for extracting gingerol from fresh gingers by using same |
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| CN101381430A (en) * | 2008-10-09 | 2009-03-11 | 浙江工业大学 | Molecule brand polymer of curcumin, preparation method and application thereof |
| CN103012095A (en) * | 2012-12-06 | 2013-04-03 | 山东农业大学 | Method for combined extraction of variety of functional components of ginger |
| CN104277177A (en) * | 2014-10-28 | 2015-01-14 | 山东省分析测试中心 | Gingerol pseudo-template molecularly imprinted polymer and method for extracting gingerol from fresh gingers by using same |
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