CN110498827B - Method for extracting flavonoid glycoside from orange peel - Google Patents
Method for extracting flavonoid glycoside from orange peel Download PDFInfo
- Publication number
- CN110498827B CN110498827B CN201910798806.2A CN201910798806A CN110498827B CN 110498827 B CN110498827 B CN 110498827B CN 201910798806 A CN201910798806 A CN 201910798806A CN 110498827 B CN110498827 B CN 110498827B
- Authority
- CN
- China
- Prior art keywords
- orange peel
- stirring
- extracting
- solution
- flavonoid glycoside
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
Abstract
The invention relates to the field of cosmeceutics, and discloses a method for extracting flavonoid glycoside from orange peel. The invention adopts polyoxyethylene octyl phenol ether and polyethylene oxide as extracting agents to reduce cloud point, and adds inorganic salt to increase the polarity of the solvent so as to facilitate separation. The combination of high-voltage pulse electric field technology and cloud point extraction technology can lower the extraction temperature, prevent the volatilization of heat sensitive components and improve the extraction rate. The invention utilizes the flavonoid compound molecule parent nucleus composed of 2 benzene rings through three carbon bonds, not only can form a large pi bond conjugated system, but also has good super-delocalization, so that the oxygen atom in the molecule with strong chelation has stronger coordination capacity, zirconium ions are added into the crude extraction liquid to form chelate, and the ionic liquid is utilized to selectively dissolve the zirconium ions, so as to remove the zirconium ions of the complex, thereby achieving the purpose of purification.
Description
Technical Field
The invention relates to the field of cosmeceutics, in particular to a method for extracting flavonoid glycoside from orange peel.
Background
The cosmeceutical is superior to general cosmetics in the aspects of safety, effectiveness and the like, and becomes a great trend for leading the trend of cosmetics. The plant components are used as natural beauty products and have thousands of years of use history in China. Flavonoid glycoside is a polyphenol substance, and has effects of scavenging free radicals, resisting oxidation, maintaining skin luster and elasticity, and delaying skin aging.
Cloud point extraction technology is an emerging liquid-liquid extraction technology which appears in recent years, does not use volatile organic solvents, and does not affect the environment. It is based on the solubility and cloud point phenomenon of the neutral surfactant micelle water solution, and the experiment parameters are changed to initiate phase separation to separate hydrophobic substance from hydrophilic substance.
The high-voltage pulse electric field technology is a new type high-efficiency non-heat treatment technology, and is a method for repeatedly applying high-voltage pulse number to material between two poles to make treatment by utilizing the principle of that external electric field can induce cell membrane perforation. The high-voltage pulse electric field treatment has the advantages of rapidness, uniformity, capability of being carried out at room temperature and the like, and is widely applied to the fields of natural product extraction, non-thermal food processing and the like at present.
The current advanced extraction methods for extracting flavonoids mainly comprise microwave-assisted extraction (MAE), reversed phase liquid chromatography (RPLC-PDA), subcritical ethanol extraction, Pressurized Solvent Extraction (PSE) and a method combining MAE and cloud point extraction technologies. The method for extracting flavonoid glycoside by means of combining the high-voltage pulse electric field technology and the cloud point extraction technology has not been reported.
Disclosure of Invention
The invention mainly solves the technical problem that the flavonoid glycoside is extracted from orange peel by a time-saving, high-efficiency and environment-friendly method, and the high-voltage pulse electric field extraction method and the cloud point extraction technology are combined. The present invention adopts a new extracting agent, polyoxyethylene octyl phenol ether and polyethylene oxide are mixed, and the cloud point is reduced, and then the inorganic salt is added, and the polarity of the solvent is increased so as to make separation easier. The combination of high-voltage pulse electric field technology and cloud point extraction technology can properly reduce extraction temperature, prevent heat sensitive components from volatilizing and improve extraction rate. The invention does not use volatile organic solvent, does not influence the environment, and accords with the concepts of green environmental protection and sustainable development. The invention utilizes the characteristic that a molecular parent nucleus of a flavonoid compound consists of 2 benzene rings through three carbon bonds, not only can form a large pi bond conjugated system, but also has good super-delocalization, so that oxygen atoms in molecules with strong chelation have strong coordination capacity, zirconium ions are added into a crude extraction liquid to form a chelate, and a novel green solvent ionic liquid is utilized to selectively dissolve the zirconium ions to remove the zirconium ions of the complex, thereby achieving the purpose of purification.
The specific technical scheme of the invention is as follows: a method for extracting flavonoid glycoside from orange peel comprises the following steps:
1) pretreatment of raw materials: drying pericarpium Citri Tangerinae at 40-50 deg.C for 20-30 hr, pulverizing, and sieving with 20-40 mesh sieve to obtain dried pericarpium Citri Tangerinae powder;
2) preparing an extracting agent: mixing polyoxyethylene octyl phenol ether and polyethylene oxide, adding into deionized water, stirring for 2-4h, mixing, adding NaCl solution, and stirring for 10-15min to obtain an extractant;
the invention mixes polyoxyethylene octyl phenol ether and polyethylene oxide two nonionic surfactants, reduces the cloud point of the mixed system, promotes phase separation and improves the extraction rate. The addition of NaCl, an inorganic salt, can reduce the cloud point of a micelle system due to salting-out effect, the inorganic salt can reduce the repulsion between micelles, increase the attraction and precipitate the micelles, and the addition of NaCl can increase the polarity of a solvent, so that the extractant is also suitable for a high-pressure pulse technology under the condition of meeting the cloud point extraction.
3) Mixing orange peel powder with an extracting agent: weighing pericarpium Citri Tangerinae powder, adding extractant, and stirring at 35-45 deg.C for 15-20 min;
4) carrying out electric field treatment on the mixed liquid obtained in the step 3) through a high-voltage pulse electric field device at the flow rate of 8-12mL/min, centrifuging the obtained extracting solution for 2-3min, and taking an enriched phase;
5) standing the enriched phase obtained in step 4) in 30-40 deg.C constant temperature water bath for 10-20min for layering, centrifuging the layered supernatant for 3-5min, and removing the supernatant to obtain crude extract;
6) adding the crude extract obtained in the step 5) into a three-neck round-bottom flask, adding ethanol, stirring for 2-3h, mixing uniformly, adding sodium ethoxide solution, and rapidly adding zirconium oxychloride (ZrOCl)2) The solution was stirred under reflux for 6h.
The invention utilizes the characteristic that a molecular parent nucleus of a flavonoid compound consists of 2 benzene rings through three carbon bonds, not only can form a large pi bond conjugated system, but also has good super-delocalization degree, so that oxygen atoms in molecules with strong chelation have strong coordination capacity, zirconium ions are added into a crude extraction liquid to form a chelate, and the zirconium ions are removed subsequently, thereby achieving the purpose of purification.
7) Preparing chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid by a cation ring-opening polymerization method, adding the prepared chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid into the system which is reacted in the step 6) by using a constant flow pump under the condition of constant-temperature stirring, and continuously stirring for 1-2 hours to ensure that the reaction is complete.
The method utilizes novel green solvent ionic liquid to selectively dissolve zirconium ions and remove the zirconium ions of the complex in the step 6).
8) Adding 20-30mL of 0.1-0.3mol/L ammonia water solution into the step 7), standing for layering, removing the lower layer liquid, and drying the upper layer liquid to obtain the purified flavonoid glycoside extract.
Preferably, in the step 2), the mass ratio of the polyoxyethylene octyl phenol ether to the polyethylene oxide is 2:1-3:1, and after the deionized water and the NaCl solution are added, the sodium chloride content in the extracting agent is maintained at 1.3% -1.6%.
Preferably, in the step 3), the liquid-solid ratio of the extracting agent to the orange peel powder is 80-125 mL/g.
Preferably, in the step 4), the high-voltage pulse electric field device has 7-9 pulse numbers and the electric field intensity of 17-20 kV/cm.
Preferably, in the steps 4) and 5), the centrifugal speed is 3600-3900 rpm.
Preferably, the specific preparation step of the sodium ethoxide solution in the step 6) is to weigh 6.82-10.23g of sodium ethoxide to be dissolved in 20-30mL of ethanol, and the concentration of the ZrOCl2 solution is 0.1-0.2 mol/L.
Preferably, the constant-temperature stirring temperature in the step 7) is 40-50 ℃, and the flow rate of the constant-flow pump is 6-8 mL/min;
compared with the prior art, the invention has the beneficial effects that: the invention provides a method for extracting flavonoid glycoside from orange peel, which is characterized in that the flavonoid glycoside is extracted by a time-saving, efficient, green and environment-friendly method, and the high-voltage pulse electric field extraction method and the cloud point extraction technology are combined to extract the flavonoid glycoside from the orange peel. The present invention adopts a new extracting agent, polyoxyethylene octyl phenol ether and polyethylene oxide are mixed, and the cloud point is reduced, and then the inorganic salt is added, and the polarity of the solvent is increased so as to make separation easier. The combination of high-voltage pulse electric field technology and cloud point extraction technology can properly reduce extraction temperature, prevent heat sensitive components from volatilizing and improve extraction rate. The invention does not use volatile organic solvent, does not influence the environment, and accords with the concepts of green environmental protection and sustainable development. The invention utilizes the characteristic that a molecular parent nucleus of a flavonoid compound consists of 2 benzene rings through three carbon bonds, not only can form a large pi bond conjugated system, but also has good super-delocalization, so that oxygen atoms in molecules with strong chelation have strong coordination capacity, zirconium ions are added into a crude extraction liquid to form a chelate, and a novel green solvent ionic liquid is utilized to selectively dissolve the zirconium ions to remove the zirconium ions of the complex, thereby achieving the purpose of purification.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
1) Pretreatment of raw materials: drying orange peel in a drying oven at 45 ℃ for 24h, crushing and sieving with a 30-mesh sieve to obtain dried orange peel powder for later use;
2) preparing an extracting agent: adding polyoxyethylene octyl phenol ether and polyethylene oxide into deionized water according to the ratio of 2:1 to prepare a solution of 0.05g/mL, stirring for 2 hours by using a magnetic stirrer to uniformly mix the solution, adding a NaCl solution to keep the content of the NaCl solution at 1.5% (w/v), and stirring for 10 minutes;
3) mixing orange peel powder with an extracting agent: weighing 0.4g of orange peel powder, adding 36mL of the extracting agent prepared in the step 2), controlling the liquid-solid ratio to be 90: 1, and magnetically stirring for 15min at 40 ℃;
4) carrying out electric field treatment on the mixed liquid prepared in the step 3) by a high-voltage pulse electric field device at the flow rate of 10mL/min, wherein the electric field strength is 18kV/cm, the pulse number is 7, centrifuging at the speed of 3700r/min for 2min, and taking an enriched phase;
5) standing the enriched phase obtained in the step 4) in a constant-temperature water bath at 35 ℃ for 10min to layer the enriched phase, centrifuging the layered supernatant for 3-5min, and removing the supernatant to obtain a crude extraction solution;
6) 6.82g of sodium ethoxide is weighed and dissolved in 20mL of ethanol to prepare a sodium ethoxide solution. Adding the crude extract obtained in the step 5) into a three-neck round-bottom flask, adding 60mL of ethanol, stirring for 2h, mixing uniformly, then adding 2mL of sodium ethoxide solution, and rapidly adding 8mL of zirconium oxychloride (ZrOCl) with the concentration of 0.1mol/L2) The solution is refluxed and stirred for 6 hours, and then is cooled to room temperature after the reaction is finished;
7) preparing chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid by a cation ring-opening polymerization method, adding 3mL of the prepared chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid into the system which is subjected to the reaction in the step 6) by a constant flow pump at the flow rate of 8mL/min under the condition of stirring at the constant temperature of 40 ℃, and continuously stirring for 1-2 hours to ensure that the reaction is complete.
8) Adding 20mL of 0.2mol/L ammonia water solution into the step 7), standing for layering, discarding the lower layer liquid, and drying the upper layer liquid to obtain the purified flavonoid glycoside extract.
The obtained flavonoid glycoside has extraction amount of 5mg/g and purity of 83%
Example 2
1) Pretreatment of raw materials: drying orange peel in a drying oven at 45 ℃ for 24h, crushing and sieving with a 30-mesh sieve to obtain dried orange peel powder for later use;
2) preparing an extracting agent: adding polyoxyethylene octyl phenol ether and polyethylene oxide into deionized water according to the ratio of 2.5: 1 to prepare a solution of 0.05g/mL, stirring for 3h by using a magnetic stirrer to uniformly mix the solution, adding a NaCl solution to keep the content of the NaCl solution at 1.4% (w/v), and stirring for 12 min;
3) mixing orange peel powder with an extracting agent: weighing 0.6g of orange peel powder, adding 60mL of the extracting agent prepared in the step 2), controlling the liquid-solid ratio to be 100: 1, and magnetically stirring for 14min at 40 ℃;
4) carrying out electric field treatment on the mixed liquid prepared in the step 3) by a high-voltage pulse electric field device at the flow rate of 10mL/min, wherein the electric field strength is 19kV/cm, the pulse number is 8, centrifuging the mixed liquid at the speed of 3800r/min for 3min, and taking an enriched phase;
5) standing the enriched phase obtained in the step 4) in a constant-temperature water bath at 34 ℃ for 10min to layer the enriched phase, taking the layered supernatant, centrifuging the supernatant for 5min at a speed of 3800r/min, and removing the supernatant to obtain a crude extraction solution;
6) 8.18g of sodium ethoxide was weighed and dissolved in 25mL of ethanol to prepare a sodium ethoxide solution. Adding the crude extract obtained in the step 5) into a three-neck round-bottom flask, adding 65mL of ethanol, stirring for 2h, mixing uniformly, adding 3mL of sodium ethoxide solution, and rapidly adding 7mL of zirconium oxychloride (ZrOCl) with the concentration of 0.15mol/L2) The solution is refluxed and stirred for 6 hours, and then is cooled to room temperature after the reaction is finished;
7) preparing 1-carboxyl polyether-3-methylimidazolium chloride polyether ionic liquid by a cation ring-opening polymerization method, adding 4mL of the prepared 1-carboxyl polyether-3-methylimidazolium chloride polyether ionic liquid into the system which is subjected to the reaction in the step 6) at the flow rate of 7mL/min by using a constant flow pump under the condition of stirring at the constant temperature of 45 ℃, and continuously stirring for 1h to ensure that the reaction is complete.
8) Adding 30mL of 0.1mol/L ammonia water solution into the step 7), standing for layering, removing the lower layer liquid, and drying the upper layer liquid to obtain the purified flavonoid glycoside extract.
The obtained flavonoid glycoside has extraction amount of 5.8mg/g and purity of 84%
Example 3
1) Pretreatment of raw materials: drying orange peel in a drying oven at 45 ℃ for 24h, crushing and sieving with a 30-mesh sieve to obtain dried orange peel powder for later use;
2) preparing an extracting agent: adding polyoxyethylene octyl phenol ether and polyethylene oxide into deionized water according to the ratio of 3:1 to prepare a solution of 0.05g/mL, stirring for 2 hours by using a magnetic stirrer to uniformly mix the solution, adding a NaCl solution to keep the content of the NaCl solution at 1.4% (w/v), and stirring for 13 minutes;
3) mixing orange peel powder with an extracting agent: weighing 0.4g of orange peel powder, adding 34mL of the extracting agent prepared in the step 2), controlling the liquid-solid ratio to be 85: 1, and magnetically stirring for 13min at 46 ℃;
4) carrying out electric field treatment on the mixed liquid prepared in the step 3) through a high-voltage pulse electric field device at the flow rate of 10mL/min, wherein the electric field strength is 20kV/cm, the pulse number is 8, centrifuging the mixed liquid at the speed of 3800r/min for 3min, and taking an enriched phase;
5) standing the enriched phase obtained in the step 4) in a constant-temperature water bath at 38 ℃ for 10min to layer the enriched phase, taking the layered supernatant, centrifuging the supernatant for 3min at the speed of 3750r/min, and removing the supernatant to obtain a crude extraction solution;
6) 10.23g of sodium ethoxide was weighed and dissolved in 30mL of ethanol to prepare a sodium ethoxide solution. Adding the crude extract obtained in the step 5) into a three-neck round-bottom flask, adding 80mL of ethanol, stirring for 2h, mixing uniformly, then adding 3mL of sodium ethoxide solution, and rapidly adding 8mL of zirconium oxychloride (ZrOCl) with the concentration of 0.2mol/L2) The solution is refluxed and stirred for 6 hours, and then is cooled to room temperature after the reaction is finished;
7) preparing chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid by a cation ring-opening polymerization method, adding 3mL of the prepared chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid into the system which is subjected to the reaction in the step 6) by a constant flow pump at the flow rate of 10mL/min under the condition of stirring at the constant temperature of 42 ℃, and continuously stirring for 2h to ensure that the reaction is complete.
8) Adding 20mL of 0.15mol/L ammonia water solution into the step 7), standing for layering, discarding the lower layer liquid, and drying the upper layer liquid to obtain the purified flavonoid glycoside extract.
The obtained flavonoid glycoside has extraction amount of 5.4mg/g and purity of 82%
The raw materials and equipment used in the invention are common raw materials and equipment in the field if not specified; the methods used in the present invention are conventional in the art unless otherwise specified.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and all simple modifications, alterations and equivalents of the above embodiments according to the technical spirit of the present invention are still within the protection scope of the technical solution of the present invention.
Claims (6)
1. A method for extracting flavonoid glycoside from orange peel is characterized by comprising the following steps of:
1) pretreatment of raw materials: drying pericarpium Citri Tangerinae at 40-50 deg.C for 20-30 hr, pulverizing, and sieving with 20-40 mesh sieve to obtain dried pericarpium Citri Tangerinae powder;
2) preparing an extracting agent: mixing polyoxyethylene octyl phenol ether and polyethylene oxide, adding into deionized water, stirring for 2-4h, mixing, adding NaCl solution, and stirring for 10-15min to obtain an extractant;
3) mixing orange peel powder with an extracting agent: weighing pericarpium Citri Tangerinae powder, adding extractant, and stirring at 35-45 deg.C for 15-20 min;
4) carrying out electric field treatment on the mixed liquid obtained in the step 3) through a high-voltage pulse electric field device at the flow rate of 8-12mL/min, centrifuging the obtained extracting solution for 2-3min, and taking an enriched phase; the number of pulses of the high-voltage pulse electric field device is 7-9, and the electric field intensity is 17-20 kV/cm;
5) standing the enriched phase obtained in step 4) in 30-40 deg.C constant temperature water bath for 10-20min for layering, centrifuging the layered supernatant for 3-5min, and removing the supernatant to obtain crude extract;
6) adding the crude extraction liquid obtained in the step 5) into a three-neck round-bottom flask, adding ethanol, stirring for 2-3h, mixing uniformly, then adding a sodium ethoxide solution, rapidly adding a zirconium oxychloride solution, refluxing and stirring for 5-7h, and cooling to room temperature after the reaction is finished;
7) preparing chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid by a cation ring-opening polymerization method, adding the prepared chlorinated 1-carboxyl polyether-3-methyl imidazolium salt polyether ionic liquid into the system which is reacted in the step 6) by using a constant flow pump under the condition of constant-temperature stirring, and continuously stirring for 1-2 hours to ensure that the reaction is complete;
8) adding 0.1-0.3mol/L ammonia water solution into the step 7), standing for layering, discarding the lower layer liquid, and drying the upper layer liquid to obtain the purified flavonoid glycoside extract.
2. The method for extracting flavonoid glycoside from orange peel according to claim 1, wherein in the step 2), the mass ratio of polyoxyethylene octyl phenol ether to polyethylene oxide is 2:1-3:1, and the sodium chloride content in the extractant is maintained at 1.3-1.6% after deionized water and NaCl solution are added.
3. The method for extracting flavonoid glycoside from orange peel according to claim 1, wherein in step 3), the liquid-solid ratio of the extractant to the orange peel powder is 80-125 mL/g.
4. The method as claimed in claim 1, wherein the centrifugation speed in step 4) and step 5) is 3600-3900 rpm.
5. The method for extracting flavonoid glycoside from orange peel as claimed in claim 1, wherein the sodium ethoxide solution of step 6) is prepared by weighing 6.82-10.23g of sodium ethoxide and dissolving in 20-30mL of ethanol, wherein the concentration of zirconium oxychloride solution is 0.1-0.2 mol/L.
6. The method for extracting flavonoid glycoside from orange peel according to claim 1, wherein in the step 7), the stirring temperature is constant at 40-50 ℃ and the flow rate of the constant flow pump is 6-8 mL/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910798806.2A CN110498827B (en) | 2019-08-27 | 2019-08-27 | Method for extracting flavonoid glycoside from orange peel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910798806.2A CN110498827B (en) | 2019-08-27 | 2019-08-27 | Method for extracting flavonoid glycoside from orange peel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110498827A CN110498827A (en) | 2019-11-26 |
| CN110498827B true CN110498827B (en) | 2020-08-18 |
Family
ID=68590121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910798806.2A Active CN110498827B (en) | 2019-08-27 | 2019-08-27 | Method for extracting flavonoid glycoside from orange peel |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110498827B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113769437A (en) * | 2021-10-22 | 2021-12-10 | 武汉轻工大学 | Method for rapidly extracting high-quality bioactive components from microalgae cells and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008034228A1 (en) * | 2006-09-18 | 2008-03-27 | Mcgill University | Pulsed electric field enhanced method of extraction |
| CN105496808A (en) * | 2015-12-22 | 2016-04-20 | 上海清轩生物科技有限公司 | Extraction method of camellia seed flavone |
| CN107693665A (en) * | 2017-10-30 | 2018-02-16 | 广西中医药大学 | The strong floor total flavone extracting method of medicine nine |
| CN108497491A (en) * | 2018-03-16 | 2018-09-07 | 惠州学院 | A kind of extracting method of Xinhui tangerine peel functional components |
-
2019
- 2019-08-27 CN CN201910798806.2A patent/CN110498827B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008034228A1 (en) * | 2006-09-18 | 2008-03-27 | Mcgill University | Pulsed electric field enhanced method of extraction |
| CN105496808A (en) * | 2015-12-22 | 2016-04-20 | 上海清轩生物科技有限公司 | Extraction method of camellia seed flavone |
| CN107693665A (en) * | 2017-10-30 | 2018-02-16 | 广西中医药大学 | The strong floor total flavone extracting method of medicine nine |
| CN108497491A (en) * | 2018-03-16 | 2018-09-07 | 惠州学院 | A kind of extracting method of Xinhui tangerine peel functional components |
Non-Patent Citations (1)
| Title |
|---|
| 浊点萃取高效液相色谱法测定苦荞茶中的黄酮;彭贵龙，周光明;《四川大学学报（自然科学版）》;20140131;第51卷(第1期);第153-159页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110498827A (en) | 2019-11-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105798320B (en) | A kind of method of low temperature preparation copper nanoparticle | |
| CN110498827B (en) | Method for extracting flavonoid glycoside from orange peel | |
| CN105754073A (en) | Method for preparing and curing water-borne epoxy resin | |
| CN108467730B (en) | Method for preparing fluorescent carbon dots | |
| CN104551007A (en) | Large-scale preparation method of silver nano-sheets | |
| CN109260950A (en) | A kind of method for separating and concentrating of lithium isotope | |
| CN103723773B (en) | A kind of hydrosol of ferroferric oxide nano granules and its preparation method and application | |
| CN113768806A (en) | Glabridin ionic liquid nano solution and preparation method and application thereof | |
| CN106220636B (en) | A kind of method that phenylamino porphyrin self-assembled nanometer material is prepared using cosolvent method | |
| CN105769653A (en) | SOD skin-caring composition with stable activity and preparing method thereof | |
| CN114574697A (en) | Method for extracting and separating rare earth neodymium from phosphate ionic liquid | |
| CN109384203B (en) | Pyrite type copper diselenide and preparation method thereof | |
| CN102303882B (en) | Method for preparing alpha-Al2O3 powder from microemulsion | |
| CN107522221A (en) | A kind of method that active porous nano ceric oxide is prepared based on inorganic template | |
| CN107200345A (en) | A kind of preparation method of γ cuprous iodides | |
| CN103143719A (en) | Preparation method of platinum nanoparticle loaded platinum nanoparticle crystals | |
| CN102872730B (en) | Method for preparing polyvinylidene fluoride alloy film | |
| CN105440099B (en) | A kind of method and application of liquid phase synthesis polypeptide | |
| CN113135564B (en) | Preparation method of stable graphene aqueous dispersion liquid | |
| CN106191476B (en) | A method of separation lanthanide series | |
| CN106317234B (en) | A kind of extracting process of Nostoc commune polysaccharide | |
| Knorr et al. | Low-Temperature Infrared Spectral Study of the Photochemical Reaction of (CO) 5Cr: C (OMe) Ph with Solvent and Alkynes | |
| CN109824024B (en) | Preparation method of lanthanide series doped zinc selenide nano material | |
| CN102936030A (en) | Method for preparing monodisperse rare earth oxide ultrathin nanosheets | |
| CN107055627B (en) | It is a kind of that nanometer iron oxide red method is prepared by neodymium iron boron secondary slugs |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |