CN104370992B - A kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture - Google Patents
A kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture Download PDFInfo
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- CN104370992B CN104370992B CN201410661439.9A CN201410661439A CN104370992B CN 104370992 B CN104370992 B CN 104370992B CN 201410661439 A CN201410661439 A CN 201410661439A CN 104370992 B CN104370992 B CN 104370992B
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Abstract
The present invention provides and a kind of extracts ursolic acid and the method for Oleanolic Acid mixture from Glossy Privet Fruit. The method first adopts acid hydrolysis technology that the ursolic acid existed in carbohydrate ligands mode in Glossy Privet Fruit and Oleanolic Acid are hydrolyzed into free state, preferentially isolate in raw material the extraction material being rich in ursolic acid and Oleanolic Acid, then remove fat soluble organic compound in material with sherwood oil; Adopt alkaline ethanol mixed solvent again, it is aided with supersound extraction, process through washing, dissolve with ethanol etc., obtain target product. Present invention reduces raw material overall process amount; Decrease impurity when mixed solvent extracts ursolic acid and Oleanolic Acid; The mixed extraction solvent used, can make the ursolic acid of free state and Oleanolic Acid be converted into the sodium salt more easily entering in Extraction solvent; Being aided with supersound extraction can smudge cells, it is to increase two kinds of acid is from deviating to enter the ability of Extraction solvent vegetable cell. Thus, technique of the present invention improves the extraction yield of ursolic acid and Oleanolic Acid content in Glossy Privet Fruit, the consumption greatly reducing Extraction solvent, consuming little energy, significantly reduces the cost producing target product.
Description
Technical field
The present invention relates to extract from fruit and there is the technology of pharmaceutical use biomass, specifically a kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture.
Background of invention:
The dry mature fruit of Glossy Privet Fruit system Oleaceae aiphyllium glossy privet (LigustriLucidum), in avette, surface beige or atropurpureus, exocarp is thin, and endocarp is wooden, yellowish brown, and tool indulges rib, and 10-11 month is ripe. It is cool in nature, and taste is sweet, and micro-hardship, returns liver, kidney channel, has nourishing liver and kidney, the function that bright order crow sends out, and tcm clinical practice is mainly used in dizzy tinnitus, and waist knee is thin soft, early whitening of beard and hair, and order is secretly not clear waits disease. Glossy Privet Fruit fruit is rich in ursolic acid and Oleanolic Acid.
Described ursolic acid (Ursolicacid) be again ursonic acid, and Oleanolic Acid (Oleanolicacid) has another name called Rhizome and root of Udo acid, is all the main pharmacodynamics composition of Glossy Privet Fruit, is all pentacyclic triterpenoid, and molecular formula is as follows, is C30H48O3��
Ursolic acid is glossy prism in dehydrated alcohol, in fine, soft fur sample needle crystal thing in Diluted Alcohol, is rendered as the powder shape of brown color or yellow-green colour during low levels. Having special smell, fusing point is 283��285 DEG C. It is soluble in dioxane, pyridine, dissolves in methyl alcohol, ethanol, butanols, butanone, be slightly dissolved in acetone, be slightly soluble in benzene, chloroform, ether, be insoluble to water and sherwood oil. Having research to confirm, ursolic acid has many-sided pharmacological action, and gram-positive microorganism, Gram-negative bacteria, yeast are all had activity by it, has the effect of antiulcer agent, antibechic, anticancer, anti-mutation, anti-oxidant and inducing cancer cell differentiation; Its toxicity is little, anti-tumor activity strong, is a kind of active components of plants having very much Development volue, is expected to become the effective new type anticancer medicine of low poison.
Oleanolic Acid is white, needle-shaped crystals body, tasteless, is insoluble to water, dissolves in methyl alcohol, ethanol, chloroform, ether, acetone and other organic solvent, is present in various plants with the form of episome and carbohydrate ligands. Also have research confirm, Oleanolic Acid except have anti-inflammatory, calmness, Qiang Xin, diuresis, reducing blood-fat, hypoglycemic and protect liver fall enzyme, strengthen immunity etc. effect except, also chromosome damage is had provide protection, atherosclerosis is had prophylactic effect. Clinical it is used for the treatment of infectivity acute icterohepatitis, chronic viral hepatitis, has and significantly reduce gpt and removing jaundice effect.
China's Glossy Privet Fruit plant distributions is extensive, resource is enriched. The existing research of technique of ursolic acid, Oleanolic Acid is individually extracted at present from Glossy Privet Fruit. As, Shaanxi Tech Univ's journal (2008,26(4): 85-88) publish Zheng Yan, the people such as the Sudan " in Glossy Privet Fruit the Study on extraction of a ursolic acid " literary composition. The technique research that this article is done is taking the full fruit of Glossy Privet Fruit as raw material, confirm that the primary and secondary influence factor extracting ursolic acid in Glossy Privet Fruit is: Extracting temperature by test > extraction time > solid-liquid ratio > ethanol contend mark, determined optimum process condition: Extracting temperature is 80 DEG C, extraction time is 120min, solid-liquid ratio is 1: 9, ethanol contend mark is 90%, and extraction time is 2 times. But owing to Glossy Privet Fruit raw material is not made relevant treatment by the research before extraction, therefore exist and use the defects such as Extraction solvent demand is many, energy consumption is big.
And for example Ma Zhongxian published by Zun Yi medical college journal [2003,26(5): 474-475.], Pu Jiazhi, Sun Zhiyong etc. " extract the experimental technique of Oleanolic Acid " in a Glossy Privet Fruit literary composition. Method described in this article is that Glossy Privet Fruit has been separated into pericarp, pulp and seed coat, kind benevolence, and with pericarp, pulp as raw material, in the industrial alcohol of 93%��94% after refluxing extraction, adopts the separation of " alkali-soluble is saltoutd " method, obtain Oleanolic Acid; And for example Zhao's Zhang Laixin satellite, the people such as Yang Qiong [from Chinese medicinal materials Glossy Privet Fruit, extract effective component Oleanolic Acid optimised process research [J]. chemical engineer, 2011,10:11-13], disclose utilize ultrasonic fragmentation make separation of hull and kernel and extract, saltout through the heavy alkali-soluble of acid, the processing condition of the acid treatment decolouring step research such as degreasing, purified crystals extraction. And we are learnt by liquid-phase chromatographic analysis and Literature Consult, ursolic acid and Oleanolic Acid be triterpenic acid class isomers each other, and character is similar, and the Extraction and isolation method provided according to people such as Ma Zhongxian with Zhang Laixin is difficult to be separated the two. Like this, making the index of Glossy Privet Fruit Objective extraction or evaluation not bery definite on the one hand, Oleanolic Acid and ursolic acid likely extract again insufficient on the other hand, cause the wasting of resources. And in the extraction process of this research, after Glossy Privet Fruit is isolated pericarp, pulp, directly boiling under 1.5kg vapor pressure in pressure kettle, or make supersound process by ultrasonic device, follow-up directly adopts ethanol refluxing process or supersound extraction again. Visible, there is the ursolic acid and the Oleanolic Acid that are only extracted free state in the method, do not deviate from Glossy Privet Fruit fruit with the ursolic acid of carbohydrate ligands form and Oleanolic Acid, therefore when there is follow-up extraction using alcohol, the ursolic acid combined with glucosides and Oleanolic Acid are difficult to the weak point being suggested from vegetable cell.
Summary of the invention
A kind of method simultaneously extracting ursolic acid, Oleanolic Acid from Glossy Privet Fruit provided by the present invention, it is in view of ursolic acid, Oleanolic Acid are all pentacyclic triterpenoid, chemical physical property is similar, the two is difficult to again the characteristic of separation, first Glossy Privet Fruit is treated as ursolic acid and the high material of Oleanolic Acid content, Extraction and isolation Technology by studying voluntarily again, obtain the crude mixture of ursolic acid and Oleanolic Acid, reach and extract the total extraction yield height of material, consume the goal of the invention that Extraction solvent is few.
The technical solution of the inventive method
The overall craft route of the inventive method: first adopt acid hydrolysis technology, the material containing ursolic acid and Oleanolic Acid is preferentially separated, the ursolic acid existed in carbohydrate ligands mode is become free state with Oleanolic Acid acid hydrolysis from vegetable cell in Glossy Privet Fruit; Then with the sherwood oil that polarity is very weak, fat soluble organic compound in material is extracted removal, to reduce impurity when follow-up mixed solvent extracts ursolic acid and Oleanolic Acid, it is to increase the extraction yield of ursolic acid and Oleanolic Acid; Adopt the mixed solvent that alkaline ethanol forms again, the ursolic acid of free state and Oleanolic Acid are converted into sodium salt, are aided with supersound extraction, through washing and dissolve with ethanol process etc., finally obtain the crude mixture of target product-ursolic acid and Oleanolic Acid.
The implementation step of described operational path is as follows:
(1) processing Glossy Privet Fruit material: after being cleaned with clear water by complete for the Glossy Privet Fruit of 10-12 month maturation fruit, boiling 20-50 minute in dilute acid soln, by the Glossy Privet Fruit after boiling by grinding, stir, isolate pulp, then obtains dry pulp material after drying;
(2) ursolic acid and Oleanolic Acid is extracted: the dry pulp of step () is placed in reflux, add sherwood oil, and make the total mass number of dry pulp and sherwood oil volume ratio be 1g:5-20mL, reflux at the temperature of 70-90 DEG C and filter after 1.5-2.5h, extract and remove lipid-soluble substance in material, reclaim sherwood oil, by gained slag shape material, add taking by mass percent concentration 99.5% industrial alcohol and mass percent concentration as the NaOH solution of 2-12% is made into, mass percent concentration is the alkaline ethanol mixed extraction solvent of 91-95%, and make its material, the quality of liquid, volume ratio is 1:6-9, supersound extraction is carried out under bath temperature, residue is abandoned in filter, filtrate is after rotary evaporation concentration and recovery solvent, add mineral acid acidified and filter, the A throw out obtained is used rare neutralizing treatment successively, after deionized water wash, become B throw out, B throw out is again with dissolve with ethanol, filtration, B filtrate is through decolouring, concentrated, in standing certain time, finally obtain C throw out and solution, after being separated by filtration, solution is incorporated into B throw out and, in the solution of dissolve with ethanol, is the crude extract of target product-ursolic acid and Oleanolic Acid after C drying precipitate.
In above-mentioned steps (), described dilute acid soln is mass percent concentration is the H of 0.1-0.5%2SO4Solution. Or the H of preferred mass percentage concentration 0.3%2SO4Solution, cooking time is 30 minutes.
In above-mentioned steps (), being ground to after pulp is separated with fruit stone by Glossy Privet Fruit after boiling in dilute acid soln moves in water, and continuous agitate water body, pulp and fruit stone are waftd float on the surface, at once by basket sieve by settling velocity pulp taking-up slowly, and repeatedly repeatable operation like this, gained Glossy Privet Fruit pulp lyophilize is become dry pulp material.
In above-mentioned steps (two), drying pulp being placed in reflux, adds sherwood oil, filter after backflow 1.5-2.5h, slag shape material continues to repeat 3 times with the Petroleum ether extraction of same ratio; Remove fat soluble organic compound in this material, and reclaim sherwood oil; Gained slag shape material is added again the mixed extraction solvent of the alkaline ethanol composition of described material, liquid quality, volume ratio, after feed liquid mixes, the Vltrasonic device being placed under the bath temperature of temperature control 50-60 DEG C is 53HZ in ultrasonic frequency, and ultrasonic power is extract 20-30min 100% time; Supersound extraction filter after filtrate after rotary evaporation concentration and recovery solvent, then to add mineral acid be mass percent concentration is hydrochloric acid or the dilute sulphuric acid of 1-5%; The washing of gained A throw out is 1-5%Na with rare alkali2CO3��Or 1-5%NaHCO3��Or 1-5%NaOH; The decolouring of described B filtrate adds the attapulgite that liquid volume and mass ratio are 10:1 in this filtrate to decolour.
Above-mentioned, or preferably dried fruit meat quality number and sherwood oil volume ratio are 1g:10mL, and reflux 2h at the temperature of 80 DEG C.
Above-mentioned, or preferably slag shape material adds the mixed extraction solvent of alkaline ethanol composition again, and its feed liquid mass volume ratio is 1:8, and ultrasound temperature-control is 60 DEG C, and extraction time is 25min.
Above-mentioned, adding mineral acid acidified or preferred mass percentage concentration is the hydrochloric acid of 3%; The washing of A throw out is the NaHCO of 3% with rare alkali or preferred mass percentage concentration3��
Above-mentioned, the mixed extraction solvent of alkaline ethanol composition or preferred mass percentage concentration 99.5% industrial alcohol and mass percent concentration are mass percent concentration 95% alcohol mixed solution that is made into of NaOH solution of 5%.
The present invention has the following advantages:
The present invention provides a kind of technology simultaneously extracting ursolic acid and Oleanolic Acid from Glossy Privet Fruit. This technology utilizes acid-hydrolysis method that the ursolic acid existed in carbohydrate ligands mode in Glossy Privet Fruit and Oleanolic Acid are hydrolyzed into free state, preferentially isolate ursolic acid and Oleanolic Acid high-content position in Glossy Privet Fruit raw material and, as the useful material extracted, reduce the overall process amount of raw material; And the Petroleum ether extraction adopting low-pole removes lipid-soluble substance in material, decrease impurity when mixed solvent extracts ursolic acid and Oleanolic Acid; The alkaline ethanol mixed extraction solvent used makes the ursolic acid of free state and Oleanolic Acid be converted into sodium salt more easily to enter in Extraction solvent; With ultrasound assisted extraction, it is to increase two kinds of tartaric acid are deviate to enter the ability in Extraction solvent from the vegetable cell of fragmentation. Thus the technical scheme of the present invention improves the extraction yield of ursolic acid and Oleanolic Acid content in Glossy Privet Fruit, the consumption greatly reducing Extraction solvent, consuming little energy, reduces the cost producing target product.
Accompanying drawing explanation
Fig. 1 is overall craft route map of the present invention;
Fig. 2 is the schematic flow sheet of operational path implementation step one of the present invention;
Fig. 3 is the schematic flow sheet of operational path implementation step two of the present invention;
Fig. 4 is that the present invention tests detection Glossy Privet Fruit raw material different sites ursolic acid and Oleanolic Acid comparision contents schematic diagram;
Embodiment
Hereinafter providing embodiment, the present invention is further elaborated:
(1) with operational path implementation step of the present invention " process Glossy Privet Fruit material " institute foundation accompanying drawing 1,2, technical process, and the related embodiment that the testing inspection of accompanying drawing 4 provides:
(1) get ripe Glossy Privet Fruit 2.0kg, after cleaning with clear water, it is the H of 0.3% with mass percent concentration2SO4In solution, boiling is after 30 minutes, filter, by being ground to further, Glossy Privet Fruit pulp is separated gained Glossy Privet Fruit slag with fruit stone, then transfer in water, and constantly stir and pulp and fruit stone are waftd float on the surface, take immediately basket sieve by settling velocity slowly pulp take out, repeatable operation like this is repeatedly, just Glossy Privet Fruit pulp and fruit stone isolate can be obtained, further by the drying when lyophilize of Glossy Privet Fruit pulp, as the material extracting ursolic acid and Oleanolic Acid.
(2) get ripe Glossy Privet Fruit 2.0kg, after cleaning with clear water, it is the H of 0.1% with mass percent concentration2SO4In solution, boiling is after 20 minutes, filter, by being ground to further, Glossy Privet Fruit pulp is separated gained Glossy Privet Fruit slag with fruit stone, then transfer in water, and constantly stir and pulp and fruit stone waftd float on the surface, take immediately basket sieve by settling velocity slowly pulp take out, repeatable operation like this repeatedly just can obtain Glossy Privet Fruit pulp and fruit stone isolate, further by the drying when lyophilize of Glossy Privet Fruit pulp, as the material extracting ursolic acid and Oleanolic Acid.
(3) get ripe Glossy Privet Fruit 2.0kg, after cleaning with clear water, it is the H of 0.5% with mass percent concentration2SO4In solution, boiling is after 50 minutes, filter, by being ground to further, Glossy Privet Fruit pulp is separated gained Glossy Privet Fruit slag with fruit stone, then transfer in water, and constantly stir and pulp and fruit stone waftd float on the surface, take immediately basket sieve by settling velocity slowly pulp take out, repeatable operation like this repeatedly just can obtain Glossy Privet Fruit pulp and fruit stone isolate, further by the drying when lyophilize of Glossy Privet Fruit pulp, as the material extracting ursolic acid and Oleanolic Acid.
As shown in Figure 4, the present invention is by following test: washed by clear water by Glossy Privet Fruit, be the H of 0.3% with mass percent concentration2SO4In solution, boiling is after 30 minutes, filter, it is divided into two parts after boiling to process, the direct lyophilize of a copy of it becomes dry full fruit, another part is by grinding, stir, after being separated into pulp and fruit stone, fruit stone peels off into shell and kernel further, dry pulp is obtained respectively after lyophilize, dry shell and dry kernel, add full fruit totally four kinds of dried objects of direct lyophilize again, extract under ultrasound condition with the mixed solvent of same NaOH solution and ethanol composition respectively, after extraction solution holds surely, high performance liquid chromatography is adopted to carry out ursolic acid and Oleanolic Acid assay in extracting solution, result confirms that the pulp obtained after the operation process such as diluted acid boiling is as the material extracting ursolic acid and Oleanolic Acid, more ursolic acid and Oleanolic Acid value is contained than other position of Glossy Privet Fruit.
(2) related embodiment provided with the technical process testing inspection of implementation step two " extracting ursolic acid and Oleanolic Acid " the institute foundation accompanying drawing 1,3 of operational path of the present invention:
(1) it is placed in round-bottomed flask with the dry pulp 250g of Glossy Privet Fruit, adds sherwood oil, and (boiling range is 60-90 to make the total mass number of dry pulp and sherwood oil0C) volume ratio is that 1g:10mL is 800Refluxing at the temperature of C and filter after 2h, filter residue continues to repeat 3 times with the Petroleum ether extraction of same ratio. Reclaim the sherwood oil in 3 petroleum ether extracts; Its slag shape material is the NaHCO of 5% with industrial alcohol (99.5%) and mass percent concentration further3The mixed extraction solvent of the 95% ethanol composition that solution is made into is placed in temperature control Vltrasonic device under the bath temperature of 60 DEG C after mixing according to the feed liquid mass volume ratio of 1:8, and ultrasonic frequency is 53HZ, and ultrasonic power is 100%, supersound extraction 25min; After being filtered by material liquid mixture after supersound extraction, residue is abandoned in filter, and its filtrate spin concentration reclaims ethanol, then the hcl acidifying adding 3%, the A throw out obtained; Again A throw out is used 3%NaHCO successively3After rare neutralizing treatment, deionized water wash, become B throw out; B throw out is again with dissolve with ethanol, filtration, gained B filtrate adds liquid volume and mass ratio is the attapulgite decolouring of 10:1, filters, gained C filtrate concentrates to half volume, leave standstill certain time, obtain C throw out and solution, after filtration, solution is merged into B throw out and, in the solution of dissolve with ethanol, is the crude extract product of Oleanolic Acid and ursolic acid after C drying precipitate. This crude extract, through liquid chromatography inspection, ursolic acid content is 6.95%, and Oleanolic Acid content is 49.85%.
(2) it is placed in round-bottomed flask with the dry pulp 250g of Glossy Privet Fruit, adds sherwood oil, and (boiling range is 60-90 to make the total mass number of dry pulp and sherwood oil0C) volume ratio is that 1g:5mL is 700Refluxing at the temperature of C and filter after 1.5h, filter residue continues to repeat 3 times with the Petroleum ether extraction of same ratio. Reclaim the sherwood oil in 3 petroleum ether extracts; Its; Slag shape material with industrial alcohol (99.5%) and mass percent concentration be further 2% NaHCO3The mixed extraction solvent of the 91% ethanol composition that solution is made into is placed in temperature control Vltrasonic device under the bath temperature of 60 DEG C after mixing according to the feed liquid mass volume ratio of 1:6, and ultrasonic frequency is 53HZ, and ultrasonic power is 100%, supersound extraction 20min; After being filtered by material liquid mixture after supersound extraction, residue is abandoned in filter, and its filtrate spin concentration reclaims ethanol, then the hcl acidifying adding 3%, the A throw out obtained; Again A throw out is used 1%NaHCO successively3After rare neutralizing treatment, deionized water wash, become B throw out; B throw out is again with dissolve with ethanol, filtration, gained B filtrate adds liquid volume and mass ratio is the attapulgite decolouring of 10:1, filters, gained C filtrate concentrates to half volume, leave standstill certain time, obtain C throw out and solution, after filtration, solution is merged into B throw out and, in the solution of dissolve with ethanol, is the crude extract product of Oleanolic Acid and ursolic acid after C drying precipitate. This crude extract, through liquid chromatography inspection, ursolic acid content is 6.85%, and Oleanolic Acid content is 49.73%.
(3) it is placed in round-bottomed flask with the dry pulp 250g of Glossy Privet Fruit, adds sherwood oil, and (boiling range is 60-90 to make the total mass number of dry pulp and sherwood oil0C) volume ratio is that 1g:20mL is 900Refluxing at the temperature of C and filter after 2.5h, filter residue continues to repeat 3 times with the Petroleum ether extraction of same ratio. Reclaim the sherwood oil in 3 petroleum ether extracts; Its slag shape material with industrial alcohol (99.5%) and mass percent concentration be further 12% NaHCO3The mixed extraction solvent of the 95% ethanol composition that solution is made into is placed in temperature control Vltrasonic device under the bath temperature of 60 DEG C after mixing according to the feed liquid mass volume ratio of 1:9, and ultrasonic frequency is 53HZ, and ultrasonic power is 100%, supersound extraction 30min; After being filtered by material liquid mixture after supersound extraction, residue is abandoned in filter, and its filtrate spin concentration reclaims ethanol, then the hcl acidifying adding 5%, the A throw out obtained; Again A throw out is used 1%NaHCO successively3After rare neutralizing treatment, deionized water wash, become B throw out; B throw out is again with dissolve with ethanol, filtration, gained B filtrate adds liquid volume and mass ratio is the attapulgite decolouring of 10:1, filters, gained C filtrate concentrates to half volume, leave standstill certain time, obtain C throw out and solution, after filtration, solution is merged into B throw out and, in the solution of dissolve with ethanol, is the crude extract product of Oleanolic Acid and ursolic acid after C drying precipitate. This crude extract, through liquid chromatography inspection, ursolic acid content is 6.54%, and Oleanolic Acid content is 47.06%.
To sum up, the operational path of technical solution that the present invention proposes and implementation step, and given embodiment and relevant detection data confirm, the present invention can reach the goal of the invention of expection.
Claims (8)
1. one kind is extracted ursolic acid and the method for Oleanolic Acid mixture from Glossy Privet Fruit, it is characterized in that: the overall craft route of the method is: first adopt acid hydrolysis technology, the material being rich in ursolic acid and Oleanolic Acid in Glossy Privet Fruit is preferentially separated, from vegetable cell, ursolic acid is become with the glycolipid acid hydrolysis of Oleanolic Acid ursolic acid and the Oleanolic Acid of free state; Then fat soluble organic compound in material is removed with the Petroleum ether extraction of low-pole; The mixed solvent adopting alkaline ethanol to form again, is aided with supersound extraction, and the ursolic acid of free state and Oleanolic Acid are converted into sodium salt; Through washing and dissolve with ethanol process, finally obtain the crude mixture of target product-ursolic acid and Oleanolic Acid;
The implementation step of described operational path is as follows:
(1) processing Glossy Privet Fruit material: after being cleaned with clear water by complete for the Glossy Privet Fruit of 10-12 month maturation fruit, boiling 20-50 minute in dilute acid soln, by the Glossy Privet Fruit after boiling by grinding, stir, isolate pulp, then obtains dry pulp material after drying;
(2) ursolic acid and Oleanolic Acid is extracted: the dry pulp of step () is placed in reflux, add sherwood oil, and make the total mass number of dry pulp and sherwood oil volume ratio be 1g:5-20mL, reflux at the temperature of 70-90 DEG C and filter after 1.5-2.5h, extract and remove lipid-soluble substance in material, reclaim sherwood oil, by gained slag shape material, add taking by mass percent concentration 99.5% industrial alcohol and mass percent concentration as the NaOH solution of 2-12% is made into, mass percent concentration is the alkaline ethanol mixed extraction solvent of 91-95%, and make its material, the quality of liquid, volume ratio is 1:6-9, supersound extraction is carried out under bath temperature, residue is abandoned in filter, filtrate is after rotary evaporation concentration and recovery solvent, add mineral acid acidified and filter, the A throw out obtained is used rare neutralizing treatment successively, after deionized water wash, become B throw out, B throw out is again with dissolve with ethanol, filtration, B filtrate is through decolouring, concentrated, in standing certain time, finally obtain C throw out and solution, after being separated by filtration, solution is incorporated into B throw out and, in the solution of dissolve with ethanol, is the crude extract of target product-ursolic acid and Oleanolic Acid after C drying precipitate.
2. according to claim 1 a kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture, it is characterised in that: in described step (), be mass percent concentration with the diluted acid of dilute acid soln boiling it is the H of 0.1-0.5%2SO4Solution.
3. according to claim 2 a kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture, it is characterised in that: with the H of the diluted acid preferred mass percentage concentration 0.3% of dilute acid soln boiling2SO4Solution, cooking time is 30 minutes.
4. according to claim 1 a kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture, it is characterized in that: in above-mentioned steps (), being ground to after pulp is separated with fruit stone by Glossy Privet Fruit after boiling in dilute acid soln moves in water, and continuous agitate water body, pulp and fruit stone are waftd float on the surface, at once by basket sieve by settling velocity pulp taking-up slowly, and repeatedly repeatable operation like this, gained Glossy Privet Fruit pulp lyophilize is become dry pulp.
5. according to claim 1 a kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture, it is characterized in that: in above-mentioned steps (two), drying pulp is placed in reflux, add sherwood oil, filter after backflow 1.5-2.5h, slag shape material continues to repeat 3 times with the Petroleum ether extraction of same ratio; Remove fat soluble organic compound in this material, and reclaim sherwood oil; Gained slag shape material is added again the mixed extraction solvent of the alkaline ethanol composition of described material, liquid quality, volume ratio, after feed liquid mixes, the Vltrasonic device being placed under the bath temperature of temperature control 50-60 DEG C is 53HZ in ultrasonic frequency, and ultrasonic power is extract 20-30min 100% time; Supersound extraction filter after filtrate after rotary evaporation concentration and recovery solvent, then to add mineral acid be mass percent concentration is hydrochloric acid or the dilute sulphuric acid of 1-5%; The washing of gained A throw out is 1-5%Na with rare alkali2CO3��Or 1-5%NaHCO3��Or 1-5%NaOH; The decolouring of described B filtrate adds the attapulgite that liquid volume and mass ratio are 10:1 in this filtrate to decolour.
6. a kind of according to claim 1 or 5 from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture, it is characterized in that: drying pulp is placed in reflux, add sherwood oil, or preferably the total mass number of dry pulp and sherwood oil volume ratio are 1g:10mL, reflux 2h at the temperature of 80 DEG C, and slag shape material is added the mixed extraction solvent of alkaline ethanol composition, and its feed liquid mass volume ratio is 1:8, ultrasound temperature-control is 60 DEG C, and extraction time is 25min.
7. according to claim 5 a kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture, it is characterised in that: described in add mineral acid acidified or preferred mass percentage concentration be the hydrochloric acid of 3%; The washing of A throw out is the NaHCO of 3% with rare alkali or preferred mass percentage concentration3��
8. according to claim 1 a kind of from Glossy Privet Fruit, extract ursolic acid and the method for Oleanolic Acid mixture, it is characterised in that: the mixed extraction solvent of described alkaline ethanol composition or preferred mass percentage concentration 99.5% industrial alcohol and mass percent concentration are mass percent concentration 95% alcohol mixed solution that is made into of NaOH solution of 5%.
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| CN105287777B (en) * | 2015-11-27 | 2019-08-23 | 广西中医药大学 | A kind of pharmaceutical composition of diuresis |
| CN112830952B (en) * | 2021-03-02 | 2022-01-04 | 湘西自治州奥瑞克医药化工有限责任公司 | Production process for extracting purified oleanolic acid from peony seed meal |
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| CN101053580A (en) * | 2006-11-10 | 2007-10-17 | 燕山大学 | New medical application of traditional Chinese medicine privet and preparation method of its extraction |
| CN101775060A (en) * | 2010-02-08 | 2010-07-14 | 苏州宝泽堂医药科技有限公司 | Method for separating and purifying ursolic acid from glossy privet leaves |
| CN102351939A (en) * | 2011-09-05 | 2012-02-15 | 曾超 | Method for preparing high-purity ursolic acid and oleanolic acid from ligustrum lucidum ait |
| CN103453412A (en) * | 2012-05-30 | 2013-12-18 | 海洋王照明科技股份有限公司 | Pendant lamp |
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2014
- 2014-11-19 CN CN201410661439.9A patent/CN104370992B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101053580A (en) * | 2006-11-10 | 2007-10-17 | 燕山大学 | New medical application of traditional Chinese medicine privet and preparation method of its extraction |
| CN101775060A (en) * | 2010-02-08 | 2010-07-14 | 苏州宝泽堂医药科技有限公司 | Method for separating and purifying ursolic acid from glossy privet leaves |
| CN102351939A (en) * | 2011-09-05 | 2012-02-15 | 曾超 | Method for preparing high-purity ursolic acid and oleanolic acid from ligustrum lucidum ait |
| CN103453412A (en) * | 2012-05-30 | 2013-12-18 | 海洋王照明科技股份有限公司 | Pendant lamp |
Non-Patent Citations (1)
| Title |
|---|
| 女贞子中齐墩果酸的提取工艺及测定方法研究进展;王萍等;《化工时刊》;20080630;第22卷(第6期);第51-54页 * |
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