CN110305180B - Preparation process for extracting high-purity ursolic acid from rosemary - Google Patents
Preparation process for extracting high-purity ursolic acid from rosemary Download PDFInfo
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention provides a preparation process for extracting high-purity ursolic acid from rosemary, which is characterized in that an ursolic acid product with the purity of more than 99 percent is obtained by adopting different solvents for leaching, filtering, separating, crystallizing and purifying, and meanwhile, ursolic acid products with the contents of 5-20 percent, 40-60 percent and 50-70 percent and carnosic acid products with the content of 20-40 percent can also be obtained. The preparation process for extracting the high-purity ursolic acid disclosed by the invention has the advantages of high utilization rate of raw materials, repeated and recycled use of the solvent, small environmental pollution and easiness in realization of industrial production.
Description
Technical Field
The invention relates to the technical field of plant product processing, in particular to a preparation process for extracting high-purity ursolic acid from rosemary.
Background
Rosemary, a shrub belonging to the family Labiatae, prefers warm climate, native European regions and the coast of the mediterranean north of Africa, has been introduced to China in the Cao Wei period, and is occasionally applied in gardens at present. Antioxidant and rosemary essential oil having excellent antioxidant activity can be extracted from flowers and leaves of rosemary. The rosemary antioxidant is widely used for the fresh keeping and quality guarantee of medicines, fried foods, oil-rich foods and various oils and fats; the rosemary essence is used in the daily chemical industries of spice, air freshener, ant repellent, sterilization, disinsection and the like. Rosemary is a rare natural perfume plant, gives off a faint scent in the growing season, and has the effects of clearing away heart-fire and refreshing. Its stem, leaf and flower have pleasant fragrance, and the aromatic oil extracted from flower and twig can be used for preparing cosmetic raw materials such as air cleaner, perfume, perfumed soap, etc., and the most famous cosmetic lotion is made of rosemary, and can be used in beverage, skin care oil, pilatory, and washing cream. Rosemary contains antioxidant components such as carnosic acid, carnosol, rosmanol, ursolic acid, and rosmanic acid.
The ursolic acid has wide resource, low toxicity, and wide bioactivity, has remarkable effects in resisting cancer, tumor, oxidation, inflammation, protecting liver, and reducing blood lipid, and is worthy of attention. In recent years, it has been found that ursolic acid not only has a resistance effect against various carcinogenic and carcinogenic substances, but also can inhibit the growth of various malignant tumor cells. Meanwhile, ursolic acid and its derivatives also have inhibitory activity against viruses. Therefore, the pharmacological activity of ursolic acid is attracting more and more attention of medical experts. With the continuous and deep research on ursolic acid in recent years, the ursolic acid is widely applied in clinic.
At present, the technology for preparing the high-content ursolic acid product in the rosemary extraction industry is few, a macroporous resin adsorption separation method is mostly used in industrial production, the production efficiency of the product is low, and the environmental pollution is serious. And the 90% ursolic acid product is difficult to obtain by the simple processes of solvent extraction, replacement and recrystallization.
Disclosure of Invention
Therefore, the invention aims to obtain a preparation process for extracting high-purity ursolic acid from rosemary mainly by solvent replacement and assisted by an acid-base reagent.
The invention is realized by the following steps:
a preparation process for extracting high-purity ursolic acid from rosemary comprises the following steps:
step 1: selecting rosemary, extracting the rosemary by an ethanol extraction process to obtain a rosemary extract in industrial production, adding 65-75% ethanol solution which is 5-10 times of the rosemary extract powder, heating and extracting, filtering while hot, and repeatedly extracting the obtained filter residue for several times according to the above steps to obtain primary fat-soluble rosemary extract filter residue A;
step 2: combining the filtrates obtained in the step (1), concentrating under reduced pressure to obtain an extract, washing and drying to obtain a carnosic acid product with the content of 20-40%;
and step 3: adding the filter residue A obtained in the step 1 into 10-15 times of 85% ethanol, adding an alkali solution, adjusting the pH value to 11-14, stirring and dissolving for 20-30min, performing microwave treatment, filtering, removing the filter residue, adding an acid solution into the filtrate, adjusting the pH value to 2-4, standing at normal temperature for 1-2h, filtering again, and drying the obtained filter residue to obtain a filter residue B;
and 4, step 4: concentrating the filtrate obtained in the step (3) under reduced pressure to obtain an extract, filtering, adding water into filter residues, washing the filter residues to be neutral, and drying to obtain a low-content ursolic acid product with the content of 5-20%;
and 5: extracting the filter residue B obtained in the step 3 with 10-20 times of petroleum ether or n-hexane for several times, filtering, and naturally drying the filter residue or recovering the solvent to dry to obtain filter residue C;
step 6: adding 10-15 times of acetic acid into the filter residue C obtained in the step 5, heating for dissolving, filtering while hot, washing and drying the obtained filter residue to obtain an ursolic acid product with the content of 50-70%;
and 7: naturally cooling the filtrate obtained in the step 6, standing for crystallization, and filtering;
and 8: repeating the filter residue obtained in the step 7 for a plurality of times according to the step 7, washing the filter residue in the last time with ethanol and water, and drying to obtain filter residue D;
and step 9: dissolving the filter residue D obtained in the step 8 with 5-10 times of water, adding NaOH solution to adjust the PH value to 11-14, stirring for dissolving, filtering after microwave treatment, and discarding the filter residue;
step 10, concentrating the filtrate obtained in the step 9, stopping concentrating immediately after crystallization begins to occur, adding a potassium salt solution, stirring, filtering to obtain filter residue, washing with water, and drying to obtain filter residue E;
step 11: and (3) adding the filter residue E obtained in the step (10) into 10-15 times of acetic acid solution, filtering, standing and crystallizing the obtained filtrate, repeating the step for a plurality of times on the filter residue obtained by filtering, and washing and drying the finally obtained filter residue with water to obtain the high-purity ursolic acid with the purity of more than 99%.
Further, recovering the filtrate solvent in the step 2, the step 4, the step 5 and the step 7; recovering and obtaining solvent ethanol in the step 2 and the step 4, recovering and obtaining solvent petroleum ether or normal hexane in the step 5, recovering and obtaining solvent acetic acid in the step 7, and recovering and obtaining solvent acetic acid in the step 9.
Further, in the step 1, the extraction temperature is 65-80 ℃, and the extraction time is 45-60 min.
Further, in the step 3 and the step 9, the microwave extraction condition is 100-140W of microwave power, and the extraction time is 5-10 min; the alkali solution is NaOH solution.
Further, in the step 3, the acid solution is phosphoric acid or hydrochloric acid or a mixture of two acids.
Further, in the step 5, the extraction temperature of the petroleum ether or the n-hexane is 65-75 ℃, and the extraction time is 45-60min each time.
Further, in the step 6, the temperature of the solution is 70-80 ℃, and the dissolving time is 30-45 min.
Further, in the step 6, the acetic acid may be replaced by methanol, ethanol, butanol, ethyl acetate, propyl acetate or butyl acetate.
Further, in the step 10, the potassium salt solution is a saturated solution of potassium chloride and potassium sulfate.
Further, in the step 11, the mass fraction of the ursolic acid in the obtained high-purity ursolic acid product is more than 99%.
Compared with the prior art, the invention has the beneficial effects that:
1) the purity of the ursolic acid obtained by the application is high, and the content is more than 99%;
2) the application can also obtain 5% -20%, 40% -60% and 50% -70% of ursolic acid products and 20% -40% of carnosic acid products;
3) the method has the advantages of simple and convenient process, high extraction yield, high utilization rate of effective components, easy realization of industrialization and batch production, and good product safety;
4) the solvent can be recycled, the production cost is low, the produced hazardous waste is less, and the environmental pollution is less.
Detailed Description
For clear and complete description of the technical solutions in the present invention, it is obvious that the inventor combines the embodiments to describe, but the following embodiments describe only some embodiments of the present invention, not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
A preparation process for extracting high-purity ursolic acid from rosemary comprises the following steps:
step 1: selecting rosemary, extracting the rosemary by an ethanol extraction process to obtain a rosemary extract in industrial production, adding 65-75% ethanol solution which is 5-10 times of the rosemary extract powder, heating and extracting, filtering while hot, and repeatedly extracting the obtained filter residue for several times according to the above steps to obtain primary fat-soluble rosemary extract filter residue A;
step 2: combining the filtrates obtained in the step (1), concentrating under reduced pressure to obtain an extract, washing and drying to obtain a carnosic acid product with the content of 20-40%;
and step 3: adding the filter residue A obtained in the step 1 into 10-15 times of 85% ethanol, adding an alkali solution, adjusting the pH value to 11-14, stirring and dissolving for 20-30min, performing microwave treatment, filtering, removing the filter residue, adding an acid solution into the filtrate, adjusting the pH value to 2-4, standing at normal temperature for 1-2h, filtering again, and drying the obtained filter residue to obtain a filter residue B;
and 4, step 4: concentrating the filtrate obtained in the step (3) under reduced pressure to obtain an extract, filtering, adding water into filter residues, washing the filter residues to be neutral, and drying to obtain a low-content ursolic acid product with the content of 5-20%;
and 5: extracting the filter residue B obtained in the step 3 with 10-20 times of petroleum ether or n-hexane for several times, filtering, and naturally drying the filter residue or recovering the solvent to dry to obtain filter residue C;
step 6: adding 10-15 times of acetic acid into the filter residue C obtained in the step 5, heating for dissolving, filtering while hot, washing and drying the obtained filter residue to obtain an ursolic acid product with the content of 50-70%;
and 7: naturally cooling the filtrate obtained in the step 6, standing for crystallization, and filtering;
and 8: repeating the filter residue obtained in the step 7 for a plurality of times according to the step 7, washing the filter residue in the last time with ethanol and water, and drying to obtain filter residue D;
and step 9: dissolving the filter residue D obtained in the step 8 with 5-10 times of water, adding NaOH solution to adjust the PH value to 11-14, stirring for dissolving, filtering after microwave treatment, and discarding the filter residue;
step 10, concentrating the filtrate obtained in the step 9, stopping concentrating immediately after crystallization begins to occur, adding a potassium salt solution, stirring, filtering to obtain filter residue, washing with water, and drying to obtain filter residue E;
step 11: and (3) adding the filter residue E obtained in the step (10) into 10-15 times of acetic acid solution, filtering, standing and crystallizing the obtained filtrate, repeating the step for a plurality of times on the filter residue obtained by filtering, and washing and drying the finally obtained filter residue with water to obtain the high-purity ursolic acid with the purity of more than 99%.
Further, recovering the filtrate solvent in the step 2, the step 4, the step 5 and the step 7; recovering and obtaining solvent ethanol in the step 2 and the step 4, recovering and obtaining solvent petroleum ether or normal hexane in the step 5, recovering and obtaining solvent acetic acid in the step 7, and recovering and obtaining solvent acetic acid in the step 9.
Further, in the step 1, the extraction temperature is 65-80 ℃, and the extraction time is 45-60 min.
Further, in the step 3 and the step 9, the microwave extraction condition is 100-140W of microwave power, and the extraction time is 5-10 min; the alkali solution is NaOH solution.
Further, in the step 3, the acid solution is phosphoric acid or hydrochloric acid or a mixture of two acids.
Further, in the step 5, the extraction temperature of the petroleum ether or the n-hexane is 65-75 ℃, and the extraction time is 45-60min each time.
Further, in the step 6, the temperature of the solution is 70-80 ℃, and the dissolving time is 30-45 min.
Further, in the step 6, the acetic acid may be replaced by methanol, ethanol, butanol, ethyl acetate, propyl acetate or butyl acetate.
Further, in the step 10, the potassium salt solution is a saturated solution of potassium chloride and potassium sulfate.
Examples 1 to 4 and comparative examples 1 to 4 were prepared according to the above preparation method by combining the parameters shown in tables 1 to 2.
Table 1:
table 2:
comparative example 5:
absent steps 1-2, the extraction was directly performed with 85% ethanol and the remaining steps were prepared as in example 3.
Comparative example 6:
absent step 3, impurities were removed without acid-base separation, and the remainder was prepared as in example 3.
Comparative example 7:
absent steps 9-10, multiple recrystallizations were carried out directly after obtaining ursolic acid crude product in step 8, and the rest was prepared as in example 3.
Comparative example 8:
absent microwave treatment, the remainder was prepared as in example 3.
The results are shown in tables 3 to 4, in which the amount of extraction is the amount obtained per 100g of the starting material in the final product.
Table 3:
| unit of | Example 1 | Example 2 | Example 3 | Example 4 | Comparative example 1 | Comparative example 2 | |
| Concentration of Ursolic acid | ％ | 99.2 | 99.5 | 99.7 | 99.4 | 95.2 | 94.8 |
| Amount of extraction | g | 5.46 | 5.73 | 5.94 | 5.80 | 5.13 | 4.51 |
Table 4:
| unit of | Comparative example 3 | Comparative example 4 | Comparative example 5 | Comparative example 6 | Comparative example 7 | Comparative example 8 | |
| Concentration of Ursolic acid | ％ | 93.1 | 92.1 | 87.6 | 86.4 | 91.2 | 94.3 |
| Amount of extraction | g | 4.28 | 4.16 | 4.09 | 3.74 | 4.25 | 4.63 |
It can be seen that the purity of the obtained ursolic acid is more than 99% according to the preparation method provided by the application. Beyond the methods given in this application, the purity of the final product can be affected.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. A preparation method for extracting high-purity ursolic acid from rosemary is characterized by comprising the following steps:
step 1: selecting rosemary, extracting the rosemary by an ethanol extraction process to obtain a rosemary extract in industrial production, adding 65-75% ethanol solution which is 5-10 times of the rosemary extract powder, heating and extracting, wherein the extraction temperature is 65-80 ℃, the extraction time is 45-60min, filtering while hot, and repeatedly extracting the obtained filter residue for a plurality of times according to the above steps to obtain primary fat-soluble rosemary extract filter residue A;
step 2: combining the filtrates obtained in the step (1), concentrating under reduced pressure to obtain an extract, washing and drying to obtain a carnosic acid product with the content of 20-40%;
and step 3: adding the filter residue A obtained in the step 1 into 10-15 times of 85% ethanol, adding an alkali solution, adjusting the pH value to 11-14, stirring and dissolving for 20-30min, performing microwave treatment, filtering, removing the filter residue, adding an acid solution into the filtrate, adjusting the pH value to 2-4, standing at normal temperature for 1-2h, filtering again, and drying the obtained filter residue to obtain a filter residue B;
and 4, step 4: concentrating the filtrate obtained in the step (3) under reduced pressure to obtain an extract, filtering, adding water into filter residues, washing the filter residues to be neutral, and drying to obtain a low-content ursolic acid product with the content of 5-20%;
and 5: extracting the filter residue B obtained in the step 3 with 10-20 times of petroleum ether or n-hexane for several times, filtering, and naturally drying the filter residue or recovering the solvent to dry to obtain filter residue C;
step 6: adding 10-15 times of acetic acid into the filter residue C obtained in the step 5, heating for dissolving, filtering while hot, washing and drying the obtained filter residue to obtain an ursolic acid product with the content of 50-70%;
and 7: naturally cooling the filtrate obtained in the step 6, standing for crystallization, and filtering;
and 8: repeating the filter residue obtained in the step 7 for a plurality of times according to the step 6, washing the filter residue in the last time with ethanol and water, and drying to obtain filter residue D;
and step 9: dissolving the filter residue D obtained in the step 8 with 5-10 times of water, adding NaOH solution to adjust the PH value to 11-14, stirring for dissolving, filtering after microwave treatment, and discarding the filter residue;
step 10, concentrating the filtrate obtained in the step 9, stopping concentrating immediately after crystallization begins to occur, adding a potassium salt solution, stirring, filtering to obtain filter residue, washing with water, and drying to obtain filter residue E;
step 11: adding the filter residue E obtained in the step 10 into 10-15 times of acetic acid solution, filtering, standing the obtained filtrate for crystallization, repeating the step for a plurality of times on the filter residue obtained by filtering, and washing and drying the finally obtained filter residue with water to obtain the high-purity ursolic acid with the purity of more than 99%;
in the steps 3 and 9, the microwave extraction condition is 100-; the alkali solution is NaOH solution.
2. The method for preparing high-purity ursolic acid from rosemary according to claim 1, wherein the filtrate solvent in the step 2, the step 4, the step 5, the step 7 and the step 11 is recovered; recovering and obtaining solvent ethanol in the step 2 and the step 4, recovering and obtaining solvent petroleum ether or normal hexane in the step 5, recovering and obtaining solvent acetic acid in the step 7, and recovering and obtaining solvent acetic acid in the step 11.
3. The method as claimed in claim 1, wherein the acid solution in step 3 is phosphoric acid or hydrochloric acid or a mixture of both acids.
4. The method for extracting high-purity ursolic acid from rosemary according to claim 1, wherein in the step 5, the extraction temperature of petroleum ether or n-hexane is 65-75 ℃ and the extraction time is 45-60min each time.
5. The method of claim 1, wherein the temperature of the solution in step 6 is 70-80 ℃ and the dissolution time is 30-45 min.
6. The method as claimed in claim 1, wherein the acetic acid is replaced with methanol, ethanol, butanol, ethyl acetate, propyl acetate or butyl acetate in the step 6.
7. The method as claimed in claim 1, wherein the potassium salt solution is a saturated solution of potassium chloride and potassium sulfate in the step 10.
8. The method of claim 1, wherein the mass fraction of ursolic acid in the high purity ursolic acid product obtained in step 11 is more than 99%.
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| CN103102384B (en) * | 2012-12-30 | 2015-08-26 | 中山百灵生物技术有限公司 | Method for extracting high-purity ursolic acid from rosemary |
| CN104447334A (en) * | 2014-12-22 | 2015-03-25 | 付大亮 | Comprehensive extraction technology of rosmarinic acid, ursolic acid, oleanolic acid and carnosic acid |
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