CN101967083B - Method for separating and refining polyprenol in ginkgo biloba extract - Google Patents
Method for separating and refining polyprenol in ginkgo biloba extract Download PDFInfo
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Abstract
The invention relates to a method for separating and refining polyprenol in ginkgo biloba extract. The method comprises the following steps: placing polyprenol extract in alcoholic lye to fully stir, saponifying at 30-80 DEG C for 0.5-4h, neutralizing the reaction liquid with acid, concentrating to obtain the saponified polyprenol extract; dissolving urea in loading solvent, adding carrier to ensure that urea is loaded on the carrier, removing solvent, preparing stationary phase; performing the column-packing of the prepared stationary phase, then adding the saponified polyprenol extract in the column, injecting mobile phase in the chromatographic column at a constant speed to elute, collecting elution components during different periods; combining the elution components which are rich in polyprenol, concentrating and evaporating; dissolving polyprenol which is processed by the urea column chromatography in the refluxed methanol, ethanol or acetonitrile to obtain saturated solution, freezing to crystallize, filtering, and drying to obtain polyprenol. The method of the invention has the advantages of mild operating conditions, high process recovery, high production purity, simple process and low operation cost.
Description
Technical field
The present invention relates to a kind of method of from Ginkgo Leaf medicinal extract, extracting the purifying polyprenol.
Background technology
Polyprenol polyprenol also claims Polyprenol (polyi soprenol), is the general name that isoprene monomer (isopentene group) is linked into the poly-compounds of straight chain shape, extensively exists at nature.Low-pole is soluble in organic solvent.Polyprenol is long chain aliphatic alcohol, contains a plurality of unconjugated double bonds in the structure, has the performance of very strong absorption free radical.The polyprenols that is present in the mammalian body is called as dolichol, it is sugar carrier important when glycoprotein is synthetic in the microbial film, but its content is extremely low, and polyprenols in Ginkgo biloba leaves content can account for cured leaf heavy 1～2%, be considered to the synthetic only intermediate of animal dolichol.Polyprenols From The Leaves of Ginkco Biloba L is nontoxic to human body, can be used as immunologic active material, is used for the treatment of the disease that causes because of immune deficiency, and has the effect of inducing apoptosis of tumour cell, has wide medicines and health protection application prospect.
Polyprenol medicinal extract normally extracts Ginkgo Leaf with weak polar solvent in sherwood oil, normal hexane, acetone, ethanol or the supercritical co etc. and obtains, and the content of polyprenol in medicinal extract is greatly about the 5-20% scope.The chemical ingredients of polyprenol and Various Complex is present in Ginkgo Leaf and the medicinal extract thereof, and it is large to separate the difficulty of withdrawing deposit, and step is many, and refining effect is limited.Because polyprenol is long-chain polyisoamylene base alcohol, and is very similar to the waxy substance pledge Physicochemical character in the medicinal extract a little less than the polarity, this withdraws deposit with regard to the separation of giving polyprenol and brings great challenge.
Patent of invention CN01113696.0 utilizes the methods such as solvent precipitation, extraction and silica gel column chromatography that polyprenol is made with extra care, and can obtain purity and be 95% polyprenol product; Patent of invention CN200410041670.4 utilizes the method for secondary molecular distillation, can obtain the polyprenol product of 75-95%; Patent of invention CN200410074088.8 utilizes the method for supercritical co fractional separation, and obtaining content is 80% polyprenol product; Solvent precipitation and silica gel column chromatography can be removed the most of polar material in the product, and for very limited with the effect of the approaching wax material of polyprenol physico-chemical property (comprising polarity); Molecular distillation has the advantages such as cleaning, green, but its theoretical basis is to separate by the difference of the molecular free path of material, because the molecular weight of wax material and polyprenol all has a scope distributed more widely, so that the common factor of its molecular free path is very large, so, only be difficult to the wax material in the product is separated with molecular distillation, in addition, molecular distillation must carry out under high vacuum and comparatively high temps, can increase the structure possibility of destroying the polyprenol in the product; The supercritical co fractional separation be according under the different temperature and pressures, supercritical co is different from and carry out separating-purifying the changes in solubility of different substances, this often requires separated material to have certain difference in parameters such as polarity or molecular weight, but the wax material in the Ginkgo Leaf medicinal extract and polyprenol all are the materials that polarity is extremely weak and molecular weight has wider distribution range, so, although the supercritical co fractional separation can obtain the polyprenol of 80% content, take the yield of sacrificing technique as cost.Can find out in the existing technological process, do not have the step for the separation of the wax material in the product, so, also contain a certain amount of wax material in its product, expect the polyprenol product that purity is higher, essential through complicated technological process, and process recovery ratio is often very low.So that the industrialization production of polyprenol is restricted.
Summary of the invention
It is simple to the purpose of this invention is to provide a kind of technique, and yield is more than 80%, and purity is in the preparation method of the polyprenol more than 98%.
The present invention be the Ginkgo Leaf medicinal extract that extracts take weak polar solvent as raw material, by techniques such as saponification, urea column chromatography, crystallizations, obtain purity at the polyprenol product more than 98%, and greatly improve the yield of its polyprenol.
The urea column chromatography mainly is a kind of method that is used for separating-purifying lipid acid.We find in experiment, the urea stationary phase has stronger adsorption to the wax material, and substantially do not have adsorption for the more polyprenol of two key numbers, can utilize like this absorption difference of wax material and polyprenol that they are separated, because urea is the larger material of a kind of polarity, it has strong adsorption for the polar material in the medicinal extract equally, so, can remove simultaneously the weak wax material of the stronger impurity of medicinal extract Semi-polarity and polarity, obtain the high polyprenol product of content, pass through again crystallization, content can reach more than 98%, and the yield of urea column chromatography process high (greater than 90%), technique overall yield (urea column chromatography and crystallization) is greater than 80%.Concrete operation step of the present invention is as follows:
(1) medicinal extract saponification: polyprenol medicinal extract fully stirs in pure alkaline solution, and at 30-80 ℃ of lower saponification 0.5-4h, reaction solution is with the acid neutralization, concentratedly obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: urea is dissolved in the loaded solvent, adds carrier, urea is loaded on the carrier, desolventizing makes stationary phase;
(3) urea column chromatography: the stationary phase dress post with making, then with polyprenol medicinal extract upper prop after the saponification, at the uniform velocity inject chromatography column with moving phase and carry out wash-out, the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness;
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in methyl alcohol, ethanol or the acetonitrile in the backflow, saturated solution, and freezing and crystallizing filters, and drying obtains polyprenol.
Refer to that such as the described polyprenol medicinal extract of step (1) the polyprenol content that obtains with sherwood oil, normal hexane, acetone, ethanol, supercritical carbon dioxide extraction Ginkgo Leaf is at the polyprenol medicinal extract of 5-20wt%; Referring to pure alkaline solution such as the described pure alkaline solution of step (1) is the sodium hydroxide of 1-40wt% or the methyl alcohol of potassium hydroxide, and the sodium hydroxide of 1-40wt% or the ethanolic soln of potassium hydroxide, the mass ratio of medicinal extract and pure alkaline solution are 1-10: 10.
Described acid refers to the liquid acid of any kind such as step (1), preferred hydrochloric acid or sulfuric acid.
Refer to the methanol-water solution of 40-95%, ethanol-water solution, methyl alcohol or the ethanol of 40-95% such as the described loaded solvent of step (2).
Refer to any have certain physical strength, stable pressed powder, preferred silica gel, aluminum oxide or gac such as the described carrier of step (2);
Such as the described urea of step (2): the mass ratio of carrier is 0.1-10: 1;
Refer to anyly can dissolve polyprenol and the solvent of dissolved urea not, preferred sherwood oil, normal hexane, chloroform or ethyl acetate such as the described moving phase of step (3);
The present invention has following features
1, adopt the urea column chromatography, operational condition is gentle, and process recovery ratio is high, and the technique total recovery is more than 80%.Product purity is high, and the content of polyprenol reaches more than 98%, and technique is simple, and running cost is low.
2, the urea chromatography column can reuse.
3, with short production cycle, large in batches, be convenient to industrialization.
Embodiment
Embodiment 1
(1) medicinal extract saponification: the polyprenol content that the supercritical carbon dioxide extraction Ginkgo Leaf is obtained is the 10g polyprenol medicinal extract of 20wt%, at the 100g of 1wt% KOH-methanol solution, fully stir, at 30 ℃ of lower saponification 4h, reaction solution neutralizes with hydrochloric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 100g urea is dissolved in the methyl alcohol, adds the 10g gac in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with sherwood oil and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the methyl alcohol in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 98.8wt%, technique total recovery 82wt%.
Embodiment 2
(1) medicinal extract saponification: the polyprenol content that the Petroleum ether extraction Ginkgo Leaf is obtained is the 20g polyprenol medicinal extract of 15wt%, at the 100g of 5wt% KOH-ethanolic soln, fully stir, at 40 ℃ of lower saponification 3.5h, reaction solution neutralizes with sulfuric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 100g urea is dissolved in the methyl alcohol, adds 100g silica gel in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with normal hexane and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the ethanol in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 98.6wt%, technique total recovery 82wt%.
Embodiment 3
(1) medicinal extract saponification: the polyprenol content that the acetone extraction Ginkgo Leaf is obtained is the 50g polyprenol medicinal extract of 10wt%, at the 100g of 30wt% NaOH-methanol solution, fully stir, at 50 ℃ of lower saponification 3h, reaction solution neutralizes with hydrochloric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 100g urea is dissolved in the aqueous ethanolic solution of 80wt%, adds the 200g aluminum oxide in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with chloroform and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the acetonitrile in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 99.6wt%, technique total recovery 86wt%.
Embodiment 4
(1) medicinal extract saponification: the polyprenol content that the extraction using alcohol Ginkgo Leaf is obtained is that the 60g polyprenol medicinal extract of 5wt% is at the 100g of 20wt% KOH-methanol solution, fully stir, at 70 ℃ of lower saponification 1h, reaction solution neutralizes with hydrochloric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 100g urea is dissolved in the aqueous ethanolic solution of 70wt%, adds 600g silica gel in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with ethyl acetate and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the methyl alcohol in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 98.5wt%, technique total recovery 82wt%.
Embodiment 5
(1) medicinal extract saponification: the polyprenol content that the extraction using alcohol Ginkgo Leaf is obtained is the 80g polyprenol medicinal extract of 5wt%, at the 100g of 35wt% KOH-methanol solution, fully stir, at 60 ℃ of lower saponification 1.5h, reaction solution neutralizes with sulfuric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 100g urea is dissolved in the aqueous ethanolic solution of 60wt%, adds 800g silica gel in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with sherwood oil and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the ethanol in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 98.6wt%, technique total recovery 84wt%.
Embodiment 6
(1) medicinal extract saponification: the polyprenol content that the extraction using alcohol Ginkgo Leaf is obtained is the 100g polyprenol medicinal extract of 5wt%, at the 100g of 40wt% NaOH-methanol solution, fully stir, at 80 ℃ of lower saponification 0.5h, reaction solution neutralizes with hydrochloric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 10g urea is dissolved in the aqueous ethanolic solution of 50wt%, adds the 100g aluminum oxide in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with normal hexane and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the acetonitrile in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 99.5wt%, technique total recovery 86wt%.
Embodiment 7
(1) medicinal extract saponification: the polyprenol content that the acetone extraction Ginkgo Leaf is obtained is the 60g polyprenol medicinal extract of 10wt%, at the 100g of 15wt% KOH-ethanolic soln, fully stir, at 30 ℃ of lower saponification 4h, reaction solution neutralizes with hydrochloric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 50g urea is dissolved in the aqueous ethanolic solution of 40wt%, adds the 80g aluminum oxide in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with sherwood oil and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the methyl alcohol in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 98.8wt%, technique total recovery 82wt%.
Embodiment 8
(1) medicinal extract saponification: the polyprenol content that the acetone extraction Ginkgo Leaf is obtained is the 40g polyprenol medicinal extract of 15wt%, at the 100g of 20wt% NaOH-ethanolic soln, fully stir, at 40 ℃ of lower saponification 3h, reaction solution neutralizes with sulfuric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 30g urea is dissolved in 95% the methanol aqueous solution, adds 60g silica gel in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with ethyl acetate and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the ethanol in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 98.5wt%, technique total recovery 86wt%.
Embodiment 9
(1) medicinal extract saponification: the polyprenol content that the Petroleum ether extraction Ginkgo Leaf is obtained is the 20g polyprenol medicinal extract of 20wt%, at the 100g of 8wt% NaOH-ethanolic soln, fully stir, at 30 ℃ of lower saponification 4h, reaction solution neutralizes with hydrochloric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 100g urea is dissolved in the methanol aqueous solution of 90wt%, adds the 50g gac in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with chloroform and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the acetonitrile in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 99.5wt%, technique total recovery 88wt%.
Embodiment 10
(1) medicinal extract saponification: the polyprenol content that the normal hexane extraction Ginkgo Leaf is obtained is the 60g polyprenol medicinal extract of 10wt%, at the 100g of 15wt% KOH-ethanolic soln, fully stir, at 60 ℃ of lower saponification 3h, reaction solution neutralizes with sulfuric acid, concentrated obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: 100g urea is dissolved in the methanol aqueous solution of 80wt%, adds the 80g gac in methanol solution, the rotation evaporate to dryness makes stationary phase;
(3) urea column chromatography: with the stationary phase dress post that makes, then polyprenol medicinal extract upper prop after the saponification at the uniform velocity injects chromatography column with normal hexane and carries out wash-out, and the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness.
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in the methyl alcohol in the backflow, saturated solution, and freezing and crystallizing filters, drying, the content of the polyprenol that obtains reaches 98.2wt%, technique total recovery 85wt%.
Claims (9)
1. the method for polyprenol in the separation and purification ginkgo biloba extract is characterized in that comprising the steps:
(1) medicinal extract saponification: polyprenol medicinal extract fully stirs in pure alkaline solution, and at 30-80 ℃ of lower saponification 0.5-4h, reaction solution is with the acid neutralization, concentratedly obtains polyprenol medicinal extract after the saponification;
(2) preparation of urea stationary phase: urea is dissolved in the loaded solvent, adds carrier, urea is loaded on the carrier, desolventizing makes stationary phase;
(3) urea column chromatography: the stationary phase dress post with making, then with polyprenol medicinal extract upper prop after the saponification, at the uniform velocity inject chromatography column with moving phase and carry out wash-out, the wash-out of collecting the different periods divides, and divides merging with the wash-out that is rich in polyprenol, concentrated evaporate to dryness;
(4) crystallization: the polyprenol behind the urea column chromatography is dissolved in methyl alcohol, ethanol or the acetonitrile in the backflow, saturated solution, and freezing and crystallizing filters, and drying obtains polyprenol;
Described polyprenol medicinal extract is that the polyprenol content that obtains with sherwood oil, normal hexane, acetone, ethanol or supercritical carbon dioxide extraction Ginkgo Leaf is at the polyprenol medicinal extract of 5-20wt%.
2. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 1, it is characterized in that the described pure alkaline solution of step (1) is the sodium hydroxide of 1-40wt% or the methyl alcohol of potassium hydroxide, the sodium hydroxide of 1-40wt% or the ethanolic soln of potassium hydroxide.
3. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 1, the mass ratio that it is characterized in that the described polyprenol medicinal extract of step (1) and pure alkaline solution is 1-10: 10.
4. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 1 is characterized in that the described acid of step (1) is liquid acid.
5. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 4 is characterized in that liquid acid is hydrochloric acid or sulfuric acid.
6. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 1 is characterized in that the described loaded solvent of step (2) is the methanol-water solution of 40-95wt%, ethanol-water solution, methyl alcohol or the ethanol of 40-95wt%.
7. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 1 is characterized in that the described carrier of step (2) is silica gel, aluminum oxide or gac.
8. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 1, it is characterized in that the described urea of step (2): the mass ratio of carrier is 0.1-10: 1.
9. the method for polyprenol in a kind of separation and purification ginkgo biloba extract as claimed in claim 1 is characterized in that the described moving phase of step (3) is sherwood oil, normal hexane, chloroform or ethyl acetate.
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| CN102219645B (en) * | 2011-04-29 | 2013-10-02 | 浙江省林业科学研究院 | Ultrasonic countercurrent extraction method of polyprenol |
| CN102603483B (en) * | 2012-03-13 | 2015-07-22 | 江苏大学 | Method for extracting polyprenols from ginkgo leaves |
| CN102771496B (en) * | 2012-07-26 | 2014-04-09 | 中国林业科学研究院林产化学工业研究所 | Plant growth regulator composition containing polyprenols and preparation method thereof |
| CN102775276B (en) * | 2012-07-26 | 2014-10-01 | 中国林业科学研究院林产化学工业研究所 | Preparation method of plant polyprenol with bacteriostatic and antioxidant activity and hydrogenated derivative thereof |
| CN103145528B (en) * | 2013-01-24 | 2015-02-18 | 中国林业科学研究院林产化学工业研究所 | Method of preparing high-purity polyprenol lipid by means of both high-speed countercurrent chromatography and high performance liquid chromatography |
| CN103083368B (en) * | 2013-02-05 | 2015-07-15 | 中国林业科学研究院林产化学工业研究所 | Preparation method of ginkgo leaf lipoid components having antibacterial activities |
| CN110302220A (en) * | 2019-07-23 | 2019-10-08 | 江苏贝斯康药业有限公司 | A kind of preparation method of low phenolic acid ginkgo leaf neutrality extract |
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