CN102040576A - Method for extracting myricetin from waxberry branches and leaves - Google Patents
Method for extracting myricetin from waxberry branches and leaves Download PDFInfo
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- CN102040576A CN102040576A CN2010102932093A CN201010293209A CN102040576A CN 102040576 A CN102040576 A CN 102040576A CN 2010102932093 A CN2010102932093 A CN 2010102932093A CN 201010293209 A CN201010293209 A CN 201010293209A CN 102040576 A CN102040576 A CN 102040576A
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Abstract
The invention provides a method for extracting myricetin from waxberry branches and leaves. Branches and leaves of a waxberry tree are used as raw materials in the method. The method comprises the following steps of: performing enzymolysis on the raw materials to obtain an enzymolysis product, ultrasonically extracting the enzymolysis product for 2 to 3 times by using an ethanol solution, reclaiming ethanol from the extracted solution under reduced pressure to obtain extract, refluxing and dissolving the extract by adding water, filtering while hot, naturally cooling the filtrate, crystallizing, repeating for 3 to 4 times, filtering the crystal, performing separation and purification by using n-hexane-ethyl acetate-methanol-0.5mol/L hydrochloric acid as a two-phase solvent system and adopting a high-speed countercurrent chromatograph, and drying the effluent by distillation under reduced pressure to obtain a myricetin product. The method has the advantages of simple process operation, high product purity and low cost.
Description
Technical field:
The invention belongs to the Separation of Natural Products technical field, especially relate to a kind of method of from gale branch and leaves, extracting ampelopsin.
Background technology:
Ampelopsin, the flavonols natural compounds is 3,5,7,3 ', 4 ', 5 '-quercetagetin, yellow needle-like crystal, fusing point is 324.0～325.5 ℃, is dissolved in hot methanol, ethanol, be insoluble to acetone, solubleness is 4% in 25 ℃ of water, and solubleness is bigger in the hot water, be insoluble in chloroform, sherwood oil, place the easy oxidation of air to turn green.
Ampelopsin has hypoglycemic activity: foreign study finds that ampelopsin all has hypoglycemic activity preferably to several animal models, is expected to develop hypoglycemic drug or uses as diabetic subject's foodstuff additive.Platelet activation factor (PAF) antagonistic action: external in vitro study shows, the high density ampelopsin can be by the scavenging(action) of leukocyte increasing to low density lipoprotein cholesterol, regulate its concentration in blood, the tool antithrombotic, resist myocardial ischemia, many-sided cardiovascular pharmacological effect such as microcirculation improvement, be expected to it is developed as the blood-activating stasis-removing kind medicine.Antioxygenation: ampelopsin is a cyclooxygenase 1, cyclooxygenase 2, and the 5-lipoxygenase inhibitor has extremely strong radical scavenging activity, can be used as natural antioxidants and is applied to the fresh-keeping and healthcare products of food, the storage of makeup.Liver protection function: ampelopsin can obviously reduce tetracol phenixin, D2 GalN and Yi Liuqingsuannaizhi and cause chmice acute liver injury model serum alt, AST activity and T2BIL content, alleviate the sex change and the necrosis of hepatic tissue, and improve mononuclear-macrophage phagocytic function and hemolysin content, be expected to be developed as liver protecting class medicine.Antibacterial and anti-inflammation functions: ampelopsin is in the external growth that suppresses and kill multiple drug-resistant bacteria, and anerobe have high susceptibility to red bayberry, is expected to be developed as antisepsis and anti-inflammation class medicine.Matrix metalloproteinase (MMP) inhibitor: following cardiovascular disorder and tumorigenic prevention and treatment reagent have dyeing and fugitive color not.Studies show that more than ampelopsin has broad application prospect in hypoglycemic, the antithrombotic of preparation and oxidation resistant medicine and healthcare products.
Document " high speed adverse current chromatogram purifying ampelopsin (Zhang Yousheng) ", the method of document research is that the dibydro myricetrin crude product (purity is 82.89%) that will obtain through the macroporous resin adsorption purifying adopts the HSCCC method, two-phase solvent system, separation condition etc. are optimized, can obtain the pure product of dibydro myricetrin more than 99%, this result of study shows that the HSCCC technology can obtain the purity high product aspect separating effective Chinese medicine components.Content is seldom in big right plant for ampelopsin, mainly transform at present and obtain by dibydro myricetrin, as patent (application number: application number: 200610019693.4) " a kind of preparation method of ampelopsin ", the method of this patent disclosure is water or alcohol-water decoction extraction or a refluxing extraction from vine tea and other Vitaceae ampelopsis, extract one or many, filtered while hot, behind the united extraction liquid, add alkaline assistant (as sodium bicarbonate, yellow soda ash, weakly alkaline materials such as sodium sorbate), make extracting solution pH between 7～9, carry out thaumatropy through heated and boiled, concentrate, the crystallization process, again through the alcohol-water recrystallization, get the ampelopsin crystal, but conversion condition is difficult to control, therefore provides a kind of method of from gale branch and leaves, extracting ampelopsin also to be necessary.
Summary of the invention:
The objective of the invention is in order to remedy in the nature plant ampelopsin content fewly, extraction yield is low, and purity is not high, and a kind of method of extracting ampelopsin from gale branch and leaves is provided.
The objective of the invention is to be achieved through the following technical solutions:
A kind of method of extracting ampelopsin from gale branch and leaves is characterized in that comprising following steps:
1) enzymolysis: gale branch and leaves is crushed to 10～60 orders, adds enzyme and sour water (pH is 4～6) and make fully and soak into, natural enzymolysis 5～7 days, filter zymolyte;
2) extract: above-mentioned zymolyte extracts 2-3 time with 95% ethanolic soln supersound extraction, 1～2h, filters, and filtrate decompression is removed organic solvent, and petroleum ether degreasing is slightly carried product;
3) crystallization: above-mentioned ampelopsin crude extract is added water backflow dissolving, naturally cooling, crystallization leaches crystallization and adds water backflow crystallization 2～3 times again;
4) high speed adverse current chromatogram separation and purification: with normal hexane-ethyl acetate-methyl alcohol-0.5mol/L hydrochloric acid is the two-phase solvent system, with above-mentioned crystallisate with phased soln down, more than be stationary phase mutually, descending is moving phase mutually, the effluent evaporated under reduced pressure promptly gets the ampelopsin product.
In the optional cellulase of the enzyme that uses in the described step 1), β glucanase, synaptase and the amylase one or more, the preferred β glucanase of the present invention, enzyme dosage is 0.4%～1%.
Described step 2) ultrasonic power 0.5～10kw in, a kind of in sour optional hydrochloric acid, sulfuric acid, acetate and the phosphoric acid of use.
The two-phase solvent that uses in the described step 4) is normal hexane-ethyl acetate-methyl alcohol-0.5mol/L hydrochloric acid (3: 10～20: 7～10: 9～15), and the chromatographic instrument rotating speed is 700～1000r/min, and the flow velocity of moving phase is 1～3ml/min.
Advantage of the present invention in sum is:
1) the gale branch and leaves raw material is easy to get.
2) enzymolysis, mild condition can not destroyed the aglycon structure, has reduced the side reaction generation.
3) HSCCC good separating effect, solvent load is little, need not to use carrier, has reduced the loss in the process.
Embodiment:
Embodiment 1:
Gale branch and leaves is crushed to 50 orders, takes by weighing 1kg, drop into extractor, add 2L hydrochloric acid (pH4) and soak into, add β glucanase 10g, natural enzymolysis 5 days, the filtering zymolyte that gets, zymolyte extracts with 95% ethanolic soln, filters, filtrate adds the concussion of 1L sherwood oil, changes separating funnel over to, removes petroleum ether layer, emit the centrifugal crude extract 32g of getting, add 12L water backflow dissolving, naturally cooling, crystallization leaches crystallization and adds water backflow crystallization 3 times again, filter crystallisate 8.5g.Get 120ml normal hexane, 480ml ethyl acetate, 550ml methyl alcohol, 450mlL 0.5mol/L hydrochloric acid, ultra-sonic oscillation are mixed, and shift full separating funnel, and standing demix is told phase up and down, more than be stationary phase mutually, time is moving phase mutually.Above-mentioned crystallisate is with phased soln under the 350ml, fill chromatographic column with pump with the flow of 10ml/min mutually with last, the head end and the sampling valve of post joined the opening speed controller, make spiral tube toward the clockwise direction rotation, when the chromatographic instrument rotating speed is 950r/min, be that 2.5ml/min pumps into moving phase with the flow velocity, and by the sampling valve sample introduction, each sample size is 150mg, collect effluent liquid, evaporated under reduced pressure promptly gets ampelopsin product 2.3g, content 99.3%.
Embodiment 2:
Gale branch and leaves is crushed to 40 orders, takes by weighing 1kg, drop into extractor, add 2L sulfuric acid (pH6) and soak into, add β glucanase 10g, natural enzymolysis 7 days, the filtering zymolyte that gets, zymolyte extracts with 95% ethanolic soln, filters, filtrate adds the concussion of 1.5L sherwood oil, changes separating funnel over to, removes petroleum ether layer, emit the centrifugal crude extract 27g of getting, add 15L water backflow dissolving, naturally cooling, crystallization leaches crystallization and adds water backflow crystallization 3 times again, filter crystallisate 6.5g.Get 100ml normal hexane, 500ml ethyl acetate, 300ml methyl alcohol, 400mlL 0.5mol/L hydrochloric acid, ultra-sonic oscillation are mixed, and are transferred to separating funnel, and standing demix is told phase up and down, more than be stationary phase mutually, time is moving phase mutually.Above-mentioned crystallisate is with phased soln under the 300ml, fill chromatographic column with pump with the flow of 10ml/min mutually with last, the head end and the sampling valve of post joined the opening speed controller, make spiral tube toward the clockwise direction rotation, when the chromatographic instrument rotating speed is 900r/min, be that 2ml/min pumps into moving phase with the flow velocity, and by the sampling valve sample introduction, each sample size is 250mg, collect effluent liquid, evaporated under reduced pressure promptly gets ampelopsin product 2.4g, content 99.4%.
Embodiment 3:
Gale branch and leaves is crushed to 60 orders, takes by weighing 1kg, drop into extractor, add 1.5L phosphoric acid (pH5) and soak into, add β glucanase 8g, natural enzymolysis 6 days, the filtering zymolyte that gets, zymolyte extracts with 95% ethanolic soln, filters, filtrate adds the concussion of 3L sherwood oil, changes separating funnel over to, removes petroleum ether layer, emit the centrifugal crude extract 29g of getting, add 20L water backflow dissolving, naturally cooling, crystallization leaches crystallization and adds water backflow crystallization 4 times again, filter crystallisate 6.8g.Get 100ml normal hexane, 400ml ethyl acetate, 350ml methyl alcohol, 450mlL 0.5mol/L hydrochloric acid, ultra-sonic oscillation are mixed, and are transferred to separating funnel, and standing demix is told phase up and down, more than be stationary phase mutually, time is moving phase mutually.Above-mentioned crystallisate is with phased soln under the 400ml, fill chromatographic column with pump with the flow of 12ml/min mutually with last, the head end and the sampling valve of post joined the opening speed controller, make spiral tube toward the clockwise direction rotation, when the chromatographic instrument rotating speed is 950r/min, be that 1ml/min pumps into moving phase with the flow velocity, and by the sampling valve sample introduction, each sample size is 150mg, collect effluent liquid, evaporated under reduced pressure promptly gets ampelopsin product 2.6g, content 99.0%.
Embodiment 4:
Gale branch and leaves is crushed to 10 orders, takes by weighing 5kg, drop into extractor, add 8L acetate (pH4) and soak into, add β glucanase 50g, natural enzymolysis 5 days, the filtering zymolyte that gets, zymolyte extracts with 95% ethanolic soln, filters, filtrate adds the concussion of 12L sherwood oil, changes separating funnel over to, removes petroleum ether layer, emit the centrifugal crude extract 127g of getting, add 75L water backflow dissolving, naturally cooling, crystallization leaches crystallization and adds water backflow crystallization 3 times again, filter crystallisate 34g.Get 0.6L normal hexane, 2L ethyl acetate, 1.4L methyl alcohol, 1.4L 0.5mol/L hydrochloric acid, ultra-sonic oscillation are mixed, and shift full separating funnel, and standing demix is told phase up and down, more than be stationary phase mutually, time is moving phase mutually.Above-mentioned crystallisate is with phased soln under the 1.5L, fill chromatographic column with pump with the flow of 20ml/min mutually with last, the head end and the sampling valve of post joined the opening speed controller, make spiral tube toward the clockwise direction rotation, when the chromatographic instrument rotating speed is 800r/min, be that 1.5ml/min pumps into moving phase with the flow velocity, and by the sampling valve sample introduction, each sample size is 200mg, collect effluent liquid, evaporated under reduced pressure promptly gets ampelopsin product 11.5g, content 99.1%.
Embodiment 5:
Gale branch and leaves is crushed to 20 orders, takes by weighing 5kg, drop into extractor, add 10L hydrochloric acid (pH5) and soak into, add β glucanase 50g, natural enzymolysis 7 days, the filtering zymolyte that gets, zymolyte extracts with 95% ethanolic soln, filters, filtrate adds the concussion of 10L sherwood oil, changes separating funnel over to, removes petroleum ether layer, emit the centrifugal crude extract 152g of getting, add 80L water backflow dissolving, naturally cooling, crystallization leaches crystallization and adds water backflow crystallization 4 times again, filter crystallisate 40g.Get 0.8L normal hexane, 2.4L ethyl acetate, 1.4L methyl alcohol, 2L 0.5mol/L hydrochloric acid, ultra-sonic oscillation are mixed, and are transferred to separating funnel, and standing demix is told phase up and down, more than be stationary phase mutually, time is moving phase mutually.Above-mentioned crystallisate is with phased soln under the 2L, fill chromatographic column with pump with the flow of 15ml/min mutually with last, the head end and the sampling valve of post joined the opening speed controller, make spiral tube toward the clockwise direction rotation, when the chromatographic instrument rotating speed is 1000r/min, be that 2ml/min pumps into moving phase with the flow velocity, and by the sampling valve sample introduction, each sample size is 200mg, collect effluent liquid, evaporated under reduced pressure promptly gets ampelopsin product 14.2g, content 99.2%.
Claims (4)
1. method of extracting ampelopsin from gale branch and leaves is characterized in that comprising following steps:
1) enzymolysis: gale branch and leaves is crushed to 10～60 orders, adds enzyme and sour water (pH is 4～6) and make infiltration fully, natural enzymolysis 5～7 days gets zymolyte;
2) extract: above-mentioned zymolyte extracts 2-3 time with 95% ethanolic soln supersound extraction, 1～2h, filters, and filtrate decompression is removed organic solvent, and petroleum ether degreasing is slightly carried product;
3) crystallization: above-mentioned ampelopsin crude extract is added water reflux dissolving crystallized 3～4 times;
4) high speed adverse current chromatogram separation and purification: with normal hexane-ethyl acetate-methyl alcohol-0.5mol/L hydrochloric acid is the two-phase solvent system, with above-mentioned crystallisate with phased soln down, more than be stationary phase mutually, descending is moving phase mutually, the effluent evaporated under reduced pressure promptly gets the ampelopsin product.
2. from gale branch and leaves, extract the method for ampelopsin according to claim 1, it is characterized in that in the optional cellulase of the enzyme that uses in the described step 1), β glucanase, synaptase and the amylase one or more.
3. from gale branch and leaves, extract the method for ampelopsin according to claim 1, it is characterized in that described step 2) in ultrasonic power 0.5～10kw, a kind of in sour optional hydrochloric acid, sulfuric acid, acetate and the phosphoric acid of use.
4. from gale branch and leaves, extract the method for ampelopsin according to claim 1, it is characterized in that the two-phase solvent that uses in the described step 4) is normal hexane-ethyl acetate-methyl alcohol-0.5mol/L hydrochloric acid (3: 10～20: 7～10: 9～15), the chromatographic instrument rotating speed is 700～1000r/min, and the flow velocity of moving phase is 1～3ml/min.
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| CN2010102932093A CN102040576A (en) | 2010-09-27 | 2010-09-27 | Method for extracting myricetin from waxberry branches and leaves |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2762137A1 (en) | 2013-02-05 | 2014-08-06 | Jilinsheng Jinziyuan Biotechnology Ltd. | Use of myricetin or derivatives thereof as a cathepsin k inhibitor |
| CN104045616A (en) * | 2014-06-26 | 2014-09-17 | 无锡市崇安区科技创业服务中心 | Method for extracting myricetin |
| CN105168936A (en) * | 2015-10-13 | 2015-12-23 | 鞠进英 | Nanometer wound-healing nursing gel and preparation method thereof |
| CN107397843A (en) * | 2016-05-19 | 2017-11-28 | 苏州凯祥生物科技有限公司 | Application of the Ampelopsis grossedentata extrat in farnesoid X receptor activator is prepared |
| CN108409804A (en) * | 2018-04-24 | 2018-08-17 | 厦门医学院 | A method of myricetin 3-O (3 〞-O- galloyls)-rhamnose pyranoside in separation Myrica rubra Dongkui leaf |
| CN110526891A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of texifolin is isolated and purified and identified from vine tea tissue |
| CN110526889A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of myricetin is isolated and purified and identified from vine tea tissue |
| CN110526890A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of dihydromyricetin is isolated and purified and identified from vine tea tissue |
| CN113121320A (en) * | 2021-04-20 | 2021-07-16 | 湖南医药学院 | Method for separating myricetin from waxberry bark by using high-speed counter-current chromatography |
| CN113636995A (en) * | 2021-08-16 | 2021-11-12 | 浙江大学中原研究院 | Method for purifying myricetin from waxberry leaves |
| NL2029678A (en) | 2021-11-08 | 2022-01-19 | Univ Zhejiang | Method for purifying myricetin from myrica rubra leaf |
| CN115919909A (en) * | 2021-08-16 | 2023-04-07 | 浙江省农业科学院 | Application of waxberry branch alcohol extract in preparation of anti-liver cancer drugs |
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2010
- 2010-09-27 CN CN2010102932093A patent/CN102040576A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2762137A1 (en) | 2013-02-05 | 2014-08-06 | Jilinsheng Jinziyuan Biotechnology Ltd. | Use of myricetin or derivatives thereof as a cathepsin k inhibitor |
| JP2014152175A (en) * | 2013-02-05 | 2014-08-25 | Jilinsheng Jinziyuan Biotechnology Ltd | Use of myricetin as cathepsin k inhibitor |
| CN104045616A (en) * | 2014-06-26 | 2014-09-17 | 无锡市崇安区科技创业服务中心 | Method for extracting myricetin |
| CN104045616B (en) * | 2014-06-26 | 2016-02-10 | 无锡市崇安区科技创业服务中心 | A kind of extracting method of myricetin |
| CN105168936A (en) * | 2015-10-13 | 2015-12-23 | 鞠进英 | Nanometer wound-healing nursing gel and preparation method thereof |
| CN107397843A (en) * | 2016-05-19 | 2017-11-28 | 苏州凯祥生物科技有限公司 | Application of the Ampelopsis grossedentata extrat in farnesoid X receptor activator is prepared |
| CN107397843B (en) * | 2016-05-19 | 2021-03-02 | 苏州凯祥生物科技有限公司 | Application of vine tea extract in preparation of farnesol X receptor agonist |
| CN108409804A (en) * | 2018-04-24 | 2018-08-17 | 厦门医学院 | A method of myricetin 3-O (3 〞-O- galloyls)-rhamnose pyranoside in separation Myrica rubra Dongkui leaf |
| CN110526889A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of myricetin is isolated and purified and identified from vine tea tissue |
| CN110526890A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of dihydromyricetin is isolated and purified and identified from vine tea tissue |
| CN110526891A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of texifolin is isolated and purified and identified from vine tea tissue |
| CN113121320A (en) * | 2021-04-20 | 2021-07-16 | 湖南医药学院 | Method for separating myricetin from waxberry bark by using high-speed counter-current chromatography |
| CN113121320B (en) * | 2021-04-20 | 2023-04-11 | 湖南医药学院 | Method for separating myricetin from waxberry bark by using high-speed counter-current chromatography |
| CN113636995A (en) * | 2021-08-16 | 2021-11-12 | 浙江大学中原研究院 | Method for purifying myricetin from waxberry leaves |
| CN115919909A (en) * | 2021-08-16 | 2023-04-07 | 浙江省农业科学院 | Application of waxberry branch alcohol extract in preparation of anti-liver cancer drugs |
| CN113636995B (en) * | 2021-08-16 | 2023-04-14 | 浙江大学中原研究院 | Method for purifying myricetin from waxberry leaves |
| CN115919909B (en) * | 2021-08-16 | 2023-12-19 | 浙江省农业科学院 | Application of waxberry branch alcohol extract in preparation of anti-liver cancer drugs |
| NL2029678A (en) | 2021-11-08 | 2022-01-19 | Univ Zhejiang | Method for purifying myricetin from myrica rubra leaf |
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Application publication date: 20110504 |