CN113945651A - A kind of method and application of extracting ferulic acid in Angelica sinensis by nonionic surfactant - Google Patents
A kind of method and application of extracting ferulic acid in Angelica sinensis by nonionic surfactant Download PDFInfo
- Publication number
- CN113945651A CN113945651A CN202111126747.8A CN202111126747A CN113945651A CN 113945651 A CN113945651 A CN 113945651A CN 202111126747 A CN202111126747 A CN 202111126747A CN 113945651 A CN113945651 A CN 113945651A
- Authority
- CN
- China
- Prior art keywords
- ferulic acid
- surfactant
- phase
- solution
- angelica
- 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.)
- Pending
Links
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 title claims abstract description 48
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 title claims abstract description 47
- 235000001785 ferulic acid Nutrition 0.000 title claims abstract description 47
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 title claims abstract description 47
- 229940114124 ferulic acid Drugs 0.000 title claims abstract description 47
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 43
- 239000002736 nonionic surfactant Substances 0.000 title claims abstract description 21
- 241000382455 Angelica sinensis Species 0.000 title description 20
- 239000004094 surface-active agent Substances 0.000 claims abstract description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000007864 aqueous solution Substances 0.000 claims abstract description 35
- 235000001287 Guettarda speciosa Nutrition 0.000 claims abstract description 28
- 238000000605 extraction Methods 0.000 claims abstract description 26
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 239000012071 phase Substances 0.000 claims description 64
- 239000000243 solution Substances 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 238000004458 analytical method Methods 0.000 claims description 31
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 29
- 239000000843 powder Substances 0.000 claims description 29
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 28
- 241000125175 Angelica Species 0.000 claims description 27
- 239000008346 aqueous phase Substances 0.000 claims description 27
- 238000000136 cloud-point extraction Methods 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 21
- 238000005303 weighing Methods 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 239000012488 sample solution Substances 0.000 claims description 15
- 239000006228 supernatant Substances 0.000 claims description 15
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 14
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 14
- 238000007789 sealing Methods 0.000 claims description 14
- 238000007873 sieving Methods 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 150000002191 fatty alcohols Chemical class 0.000 claims description 6
- -1 sorbitan fatty acid ester Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 claims description 5
- 229940048848 lauryl glucoside Drugs 0.000 claims description 5
- 229940080421 coco glucoside Drugs 0.000 claims description 4
- 229930182478 glucoside Natural products 0.000 claims description 4
- 150000008131 glucosides Chemical class 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 238000011002 quantification Methods 0.000 claims description 2
- 239000000523 sample Substances 0.000 claims description 2
- 230000003595 spectral effect Effects 0.000 claims description 2
- 238000003260 vortexing Methods 0.000 claims 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 238000003556 assay Methods 0.000 claims 1
- 238000011049 filling Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000010829 isocratic elution Methods 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 17
- 239000000126 substance Substances 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
- 230000007547 defect Effects 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 231100000086 high toxicity Toxicity 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 230000002087 whitening effect Effects 0.000 abstract description 2
- 244000061520 Angelica archangelica Species 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000012491 analyte Substances 0.000 description 13
- 238000004140 cleaning Methods 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 238000011084 recovery Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005325 percolation Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- 241000906579 Actaea cimicifuga Species 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 230000007082 Aβ accumulation Effects 0.000 description 1
- 235000007162 Ferula assa foetida Nutrition 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 235000012850 Ferula foetida Nutrition 0.000 description 1
- 241000112528 Ligusticum striatum Species 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000000658 coextraction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000009695 di'ao xinxuekang Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ONJQDTZCDSESIW-UHFFFAOYSA-N polidocanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ONJQDTZCDSESIW-UHFFFAOYSA-N 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008371 vanilla flavor Substances 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/062—Preparation extracting sample from raw material
Landscapes
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Medicines Containing Plant Substances (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention relates to a novel method for extracting ferulic acid from angelica and application thereof, wherein a non-ionic surfactant aqueous solution is used as an extracting agent. The method overcomes the defects of the traditional method that a large amount of volatile organic solvents such as methanol, acetone and the like are used as extracting agents, and the traditional method has the defects of high toxicity, low yield, high production cost and the like. The method does not need to remove the surfactant again, and directly adds the surfactant aqueous solution containing the ferulic acid into the daily chemical products according to a certain proportion, so that the surfactant active ingredients in the daily chemical products are improved, and the ferulic acid is added into the daily chemical products. Ferulic acid is used as a skin conditioner, and has effects of protecting skin and whitening skin. The method provided by the invention achieves the maximum solubility by using the least solvents, has the advantages of high extraction rate, short extraction time and low extraction cost, and is suitable for large-scale industrial production.
Description
Technical Field
The invention belongs to the technical field of traditional Chinese medicine preparations, and relates to a novel method for extracting ferulic acid from angelica by using a non-ionic surfactant and application thereof, in particular to a novel method for using a non-ionic surfactant aqueous solution as an extracting agent.
Background
Ferulic Acid (Ferulic Acid) with chemical name of 3-methoxy-4-hydroxycinnamic Acid and chemical formula of C10H10O4Is one of the derivatives of cinnamic acid. The content of Chinese medicinal materials such as asafetida, angelica, ligusticum wallichii, cimicifuga foetida, spina date seed and the like is high, and the Chinese medicinal materials are one of effective components of the Chinese medicaments and are already used as one of quality indexes of Chinese patent medicaments. Ferulic acid is a natural antioxidant, an ultraviolet absorbing material and a skin whitening material, such as Xinxuekang, Taitai oral liquid and the like all contain ferulic acid, and the ferulic acid is currently researched to enter the global market. Ferulic acid has also been highlighted as a material for the treatment of alzheimer's disease due to its clinical reports of its functional role in inhibiting β -amyloid accumulation (Nutrients,2015,7 (7): 5764-5782). Furthermore, ferulic acid is considered to have a very high functional and growth potential due to its high demand as raw material for vanilla flavor (vanillin) (ApplBiochem Biotechnol,2013,169 (4): 1353-.
The ferulic acid extraction method comprises percolation, flash extraction, ethanol reflux extraction, ultrasonic method, enzymolysis, alkaline hydrolysis, and CO extraction2Supercritical extraction method. Among the ferulic acid preparation methods, the percolation method is a common method for extracting the ferulic acid from angelica sinensis, but the percolation method has the disadvantages of large solvent consumption, long time and complicated operation. And the commonly used solvent is a traditional volatile organic solvent such as methanol, acetone and the like, and has the defects of high toxicity, low yield, high production cost and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a novel method for extracting ferulic acid from angelica by using a non-ionic surfactant and application thereof, and particularly relates to a novel method for using a non-ionic surfactant aqueous solution as an extracting agent.
The above objects are achieved by the following technical solutions
1. A novel method for extracting ferulic acid from angelica sinensis by using a nonionic surfactant and application thereof are characterized in that the angelica sinensis with whiskers is selected and purchased from various large drugstores in Lanzhou city.
2. A new method for extracting ferulic acid from angelica sinensis by using a nonionic surfactant and application thereof are characterized in that the nonionic surfactant selected in the method is one or a mixture of more of fatty alcohol polyoxyethylene ether (AEO-9), lauryl glucoside (APG1214), coco glucoside (APG0814), fatty alcohol polyoxyethylene ether glucoside (AEG050), coco oil acid (CMMEA6511) and polyethylene glycol monoalkyl ether (Genapol X-080), and the using amount is 1-15% (volume fraction).
3. A new method for extracting ferulic acid from angelica by using a non-ionic surfactant and application thereof are characterized in that the method comprises the following steps:
step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extraction of a surfactant aqueous solution: measuring a certain volume of nonionic surfactant aqueous solution, placing the nonionic surfactant aqueous solution into a round-bottom flask, accurately weighing a certain amount of angelica powder, adding the angelica powder, heating at a certain temperature, magnetically stirring for a certain time, and connecting a condensing pipe internally communicated with condensed water on the round-bottom flask to prevent loss of a solvent and an analyte;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
Acclaim is selected as a chromatographic columnTM C18(4.6X250mm，
5 μm), the column temperature was controlled at 35 ℃. The flow rate was 1ml/min, the amount of sample was 10. mu.l, the detection wavelength was 316nm, and the mobile phase was acetonitrile and 0.085% aqueous phosphoric acid (acetonitrile: aqueous phosphoric acid: 16:84, v/v) and was eluted at equal intervals. The identification of the spectral peaks is obtained by comparison with the retention time of ferulic acid control, and the peak area is used for quantification.
The invention has the advantages that:
the Cloud Point Extraction (CPE) belongs to an emerging liquid-liquid extraction technology, and the greatest advantage is that the CPE is not usedVolatile organic solventThe selected extractant is usually a surfactant, which has little influence on the environment and is low in price. It is used to separate hydrophilic matter from hydrophobic matter by means of the solubility of surfactant micelle aqua, altering test parameters and other conditions to initiate phase separation. Compared with the traditional liquid-liquid extraction technology, the cloud point extraction technology has the following advantages: the operation is easy; secondly, the extraction efficiency is high, the application range is wide, and the enrichment factor is large; the device is easy to be combined with an instrument analysis method; fourthly, toxic and harmful organic solvents which are harmful to the environment are not used, and the amount of the needed surfactant is small, so that the use amount of organic matters which pollute the environment is controlled to the minimum, and the method also conforms to the concept of modern green chemical industry.
The surfactant mainly comprises ionic surfactant (including cationic surfactant and anionic surfactant), nonionic surfactant, amphoteric surfactant, compound surfactant, other surfactants, etc. Wherein the nonionic surfactant is selected from fatty alcohol polyoxyethylene ether, glucoside, fatty glyceride, sorbitan fatty acid ester (span), polyoxyethylene sorbitan fatty acid ester (Tween), etc. Compared with other solvents, the nonionic surfactant extractant has the following advantages: the cloud point extraction enrichment rate is good, the dosage is small, the biodegradation performance is good, the influence of water hardness is avoided, the environment is protected, no pollution is caused, and the price is low.
The method for measuring the content of the ferulic acid by using the high performance liquid chromatography has the advantages of high analysis speed, high sensitivity, high separation efficiency and high result precision, and becomes an important separation and analysis technology in the subject fields of chemistry, medicine, industry, agriculture and the like.
The non-ionic surfactant is selected as the extracting agent, so that the defect that a large amount of volatile organic solvents such as methanol, acetone and the like are used as the extracting agent in the traditional method is overcome, and the traditional method has the defects of high toxicity, low yield, high production cost and the like; the dosage of the needed surfactant is small, the environment is not polluted, and the price is low; the surfactant aqueous solution containing the ferulic acid is directly added into daily chemical products according to a certain proportion without removing the surfactant again, so that the surfactant active ingredients in the daily chemical products are improved, and the ferulic acid is also added into the daily chemical products. Not only has high selectivity and recovery rate, but also has simple process and low production cost.
The application of the ferulic acid can be directly added into products for preparing daily necessities, cosmetics and the like for supplementing active ingredients, namely supplementing the active ingredients in the daily necessities and the cosmetics, and can also be added with the ferulic acid. The method is simple and easy to implement, has low cost and can be applied to large-scale industrial production.
Drawings
FIG. 1 is a diagram: control spectrum, wherein a is blank experiment (extractant: 10% AEO-9 aqueous solution); b, ferulic acid reference substance 70% methanol water solution; c, extracting ferulic acid from the angelica by using 10 percent of AEO-9 aqueous solution. The mobile phase is acetonitrile: 0.085% aqueous phosphoric acid solution ═ 16: 84; column temperature: 35 ℃; flow rate: 1 mL/min; WVL:316 nm.
Detailed Description
Example one
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 10% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 30min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
Example two
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) aqueous lauryl glucoside (APG1214) extraction: weighing 20ml of 10% (volume fraction) APG1214 aqueous solution, placing in a round-bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 30min, and connecting a condensing tube with condensed water in it on the round-bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
EXAMPLE III
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) aqueous extraction of coco glucoside (APG 0814): measuring 20ml of 10% (volume fraction) APG0814 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 30min, and connecting a condensing tube with condensed water in the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
Example four
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) aqueous extraction of coconut oil acid (CMMEA 6511): weighing 20ml of 10% (volume fraction) CMMEA6511 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 30min, and connecting a condensation pipe with condensed water in it on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
EXAMPLE five
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extraction of APG1214 and APG0814 mixed aqueous solution: weighing 20ml of 10% APG1214 and APG0814 mixed (volume fraction, APG1214: APG0814 ═ 1:1) aqueous solution, placing in a round-bottom flask, accurately weighing 0.2g of angelica powder, adding, heating at 50 ℃, magnetically stirring for 30min, and connecting a condenser pipe with condensed water inside on the round-bottom flask to prevent loss of solvent and analyte;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
The second to fifth embodiments are: ferulic acid was extracted from angelica sinensis by replacing the aqueous solution of the nonionic surfactant AEO-9 used in step 2) of example one with lauryl glucoside (APG1214), coco glucoside (APG0814), coco acid (CMMEA6511) and mixed APG1214 and APG0814, respectively. Wherein, the recovery rates of ferulic acid in examples one to five are shown in Table 1.
Table 1 recovery data of ferulic acid in examples one to five
| Examples | Extracting agent | Recovery rate |
| Example one | Fatty alcohol polyoxyethylene ether (AEO-9) | 94.8％ |
| Example two | Lauryl glucoside (APG1214) | 90.2％ |
| EXAMPLE III | Cococo glucoside (APG0814) | 87.7％ |
| Example four | Coconut oil acid (CMMEA6511) | 85.92 |
| EXAMPLE five | APG1214:APG0814＝1:1 | 91.5％ |
EXAMPLE six
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 1% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 30min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
EXAMPLE seven
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 5% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 30min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
Example eight
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 15% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 30min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
The sixth to ninth embodiments are: when 10% of the volume fraction of the extractant used in the step 2) in the example I is replaced by 1%, 4% and 7% respectively, ferulic acid in angelica is extracted. Wherein, the recovery rates of ferulic acid in the fifth to seventh examples are shown in Table 2.
Table 2 recovery data of ferulic acid in examples six to eight
Example nine
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 10% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 10min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
Example ten
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 10% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 20min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
EXAMPLE eleven
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 10% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 40min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, and the supernatant was transferred to another centrifuge tube and added 15% (w/v) for 02 min. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
Example twelve
Step 1) angelica pretreatment: cleaning purchased Chinese angelica, drying in the shade, crushing, sieving with a 50-mesh sieve to obtain fine powder, and sealing and storing for later use;
step 2) extracting with an aqueous solution of fatty alcohol-polyoxyethylene ether (AEO-9): measuring 20ml of 10% (volume fraction) AEO-9 aqueous solution, placing in a round bottom flask, accurately weighing 0.2g of radix Angelicae sinensis powder, adding, heating at 50 deg.C, magnetically stirring for 60min, and connecting a condensing tube with condensed water on the round bottom flask to prevent solvent and analyte loss;
step 3) cloud point extraction enrichment: the product was transferred to a centrifuge tube and centrifuged at 4000r/min for 10min, the supernatant was transferred to another centrifuge tube and vortexed for 2min by adding 15% (w/v) sodium chloride. The sample solution was then heated in a constant temperature water bath at 100 ℃ until the solution completely separated into two distinct phases, the upper one being the surfactant phase of smaller volume and the lower one being the aqueous phase of larger volume. The aqueous phase is aspirated out with a syringe having a long needle, the more viscous surfactant phase being left in the tube;
step 4) HPLC system analysis: methanol was added to the step 3 tube to reduce the viscosity of the surfactant phase, the amount of solution was made up to the cloud point before extraction, mixed well, filtered through a 0.45 μm filter and injected into the HPLC system for analysis.
Examples nine to twelve are: and (3) extracting the ferulic acid in the angelica when the heating magnetic stirring time in the step 2) in the first embodiment is respectively replaced by 10min, 20min, 40min and 60 min. Wherein, the recovery rates of ferulic acid in examples nine to twelve are shown in Table 3.
TABLE 3 recovery data for ferulic acid in examples nine to twelve
| Examples | Concentration of extractant | Recovery rate |
| Example nine | 10min | 89.8％ |
| Example ten | 20min | 91.6％ |
| EXAMPLE eleven | 40min | 94.1％ |
| Example twelve | 60min | 92.5％ |
The specific examples described above are only a part of the implementation method of the present invention, and the method of the present invention can be modified and revised without departing from the scope of the present invention, and these modifications and revisions should be considered as within the protection scope of the present invention. The method is simple and easy to implement, has low cost and can be applied to large-scale industrial production.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, improvement and the like made within the content and principle of the present invention shall be included in the protection scope of the present invention.
Claims (9)
1. A method for extracting ferulic acid, which method uses a cloud point extraction method.
2. A method as claimed in claim 1, wherein the cloud point extraction method uses a nonionic surfactant.
3. A method of extracting ferulic acid according to claim 1, wherein ferulic acid is extracted from angelica.
4. The method of claim 2, wherein the nonionic surfactant is one or more selected from fatty alcohol polyoxyethylene ether, lauryl glucoside, coco glucoside, fatty alcohol polyoxyethylene ether glucoside, coco acid, polyethylene glycol monoalkyl ether, alkylphenol ethoxylate, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and polyoxyethylene fatty acid ester.
5. A process according to claim 3, wherein the ferulic acid is prepared by: the method comprises the following steps:
step 1) angelica pretreatment: processing the purchased angelica, crushing, sieving to obtain fine powder, and sealing and storing for later use;
step 2) extraction of a surfactant aqueous solution: weighing a nonionic surfactant aqueous solution, placing in a container, weighing and adding angelica powder, heating and magnetically stirring;
step 3) cloud point extraction enrichment: transferring the product into a centrifuge tube, centrifuging, transferring the supernatant into another centrifuge tube, adding sodium chloride, and vortexing; then the sample solution is placed in a constant-temperature water bath for heating until the solution is completely divided into two different phases, wherein the upper layer is a surfactant phase with a smaller volume, and the lower layer is a water phase with a larger volume; removing the lower water phase to obtain surfactant solution rich in ferulic acid, namely the product.
6. Centrifuging at 4000r/min for 10min, transferring the supernatant to another centrifuge tube, adding 15% (w/v) sodium chloride, and vortexing for 2 min; then the sample solution is placed in a thermostatic water bath at the temperature of 80-120 ℃ to be heated until the solution is completely divided into two different phases, wherein the upper layer is a surfactant phase with a smaller volume, and the lower layer is a water phase with a larger volume; the aqueous phase was aspirated with a syringe having a long needle, and the more viscous surfactant phase was left in the tube.
7. A method as claimed in claim 5, wherein the control assay comprises:
1) analysis on HPLC system: adding methanol into the tube in the step 3 to reduce the viscosity of the surfactant phase, filling the solution amount until the cloud point extraction is completed, mixing uniformly, filtering with a filter membrane of 0.45 μm, and injecting into an HPLC system for analysis;
2) acclaim is selected as a chromatographic columnTMC18, specification of 4.6X250mm,
5 mu m, and the column temperature is controlled at 35 ℃; the flow rate is 1ml/min, the sample amount is 10 μ l, the detection wavelength is 316nm, and the mobile phase is acetonitrile and 0.085% phosphoric acid water solution, the acetonitrile: phosphoric acid aqueous solution 16:84, v/v; carrying out isocratic elution; the identification of the spectral peaks is obtained by comparison with the retention time of ferulic acid control, and the peak area is used for quantification.
8. A process as claimed in claim 5, wherein the container is a round-bottomed flask, and a condenser tube for introducing condensed water is connected to the round-bottomed flask.
9. Use of ferulic acid, characterised in that ferulic acid products are prepared by the method according to claim 1, for the preparation of active ingredient supplements in daily products and cosmetics.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111126747.8A CN113945651A (en) | 2021-09-26 | 2021-09-26 | A kind of method and application of extracting ferulic acid in Angelica sinensis by nonionic surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111126747.8A CN113945651A (en) | 2021-09-26 | 2021-09-26 | A kind of method and application of extracting ferulic acid in Angelica sinensis by nonionic surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113945651A true CN113945651A (en) | 2022-01-18 |
Family
ID=79328685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111126747.8A Pending CN113945651A (en) | 2021-09-26 | 2021-09-26 | A kind of method and application of extracting ferulic acid in Angelica sinensis by nonionic surfactant |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113945651A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115014890A (en) * | 2022-05-18 | 2022-09-06 | 深圳职业技术学院 | Sample treatment method and determination method of nitrofuran metabolites |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103408558A (en) * | 2013-07-18 | 2013-11-27 | 中国人民解放军第四军医大学 | Cloud point extraction based psoralen and isopsoralen extracting method |
| CN105548390A (en) * | 2015-12-11 | 2016-05-04 | 陇西保和堂药业有限责任公司 | Determination method for content of ferulic acid in Chinese angelica decoction pieces |
| CN107271391A (en) * | 2017-06-30 | 2017-10-20 | 潘仲巍 | Room temperature solid ionic liquid is used as the forulic acid in extractant separation determination Radix Angelicae Sinensis |
| CN111018696A (en) * | 2019-12-04 | 2020-04-17 | 浙江理工大学 | Method for extracting ferulic acid from angelica sinensis |
-
2021
- 2021-09-26 CN CN202111126747.8A patent/CN113945651A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103408558A (en) * | 2013-07-18 | 2013-11-27 | 中国人民解放军第四军医大学 | Cloud point extraction based psoralen and isopsoralen extracting method |
| CN105548390A (en) * | 2015-12-11 | 2016-05-04 | 陇西保和堂药业有限责任公司 | Determination method for content of ferulic acid in Chinese angelica decoction pieces |
| CN107271391A (en) * | 2017-06-30 | 2017-10-20 | 潘仲巍 | Room temperature solid ionic liquid is used as the forulic acid in extractant separation determination Radix Angelicae Sinensis |
| CN111018696A (en) * | 2019-12-04 | 2020-04-17 | 浙江理工大学 | Method for extracting ferulic acid from angelica sinensis |
Non-Patent Citations (2)
| Title |
|---|
| PRADIP B. DHAMOLE 等: "Extraction of p-Coumaric Acid and Ferulic Acid Using Surfactant-Based Aqueous Two-Phase System", 《APPL BIOCHEM BIOTECHNOL》 * |
| 任杰麟 等: "HPLC法检测中药洗发水中阿魏酸的含量", 《香料香精化妆品》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115014890A (en) * | 2022-05-18 | 2022-09-06 | 深圳职业技术学院 | Sample treatment method and determination method of nitrofuran metabolites |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3511064A1 (en) | Method for preparing high-purity cannabidiol | |
| CN105111255A (en) | Extraction and separation method for echinacoside and verbascoside in cistanche | |
| US20190022159A1 (en) | Novel method for preparing purified extracts of harpagophytum procumbens | |
| CN111039761A (en) | Method for purifying cannabidiol | |
| CN112010738B (en) | Industrial method for producing cannabinoid compound by utilizing chromatographic separation | |
| CN113945651A (en) | A kind of method and application of extracting ferulic acid in Angelica sinensis by nonionic surfactant | |
| Gomes et al. | Integrative process to extract chlorophyll and purify rosmarinic acid from rosemary leaves (Rosmarinus officialis) | |
| CN101260138B (en) | Highly effective separation purification method for polygalic acid and tenuigenin | |
| CN105669797B (en) | A kind of method that burdock seed oil, arctiin, arctigenin, arctigenin-4'-gentiobioside E and arctigenin-4'-gentiobioside H are separated from great burdock achene | |
| CN110092767A (en) | A method of Sync enrichment purification of paclitaxel and 10-DAB III from Chinese yew | |
| CN104211690A (en) | Method for separating and purifying mangiferin from aquilaria sinensis leaves | |
| CA3042612C (en) | Method for determining content of menthol in preparation of traditional chinese medicine composition | |
| CN111307969B (en) | Method for simultaneously extracting phenolic acid glycosides and polysaccharides in traditional Chinese medicine | |
| CN105031070A (en) | Viola tricolor extract for treating gouty arthritis and preparation method thereof | |
| CN101982466B (en) | Method for extracting isoflavonoids compound in all-grass of Twining Rhynchosia with ionic liquid | |
| CN104398557A (en) | Method for preparing general flavones by using complexing method | |
| CN109810149A (en) | A kind of extraction process of shrub althea flower procyanidins | |
| CN103316087B (en) | Semen Myristicae five tastes effective site and preparation method thereof, quality determining method and application | |
| CN106896180A (en) | A kind of detection method of Bushen Tianjing oral liquid | |
| CN106719899A (en) | A kind of plant flavor-absorbing disinfecting agent proportioning processes of TR 001 | |
| CN102492003B (en) | Technique for extracting and separating salidroside from glossy privet fruit | |
| CN107669728B (en) | Rape pollen total sterol for treating prostatic hyperplasia and preparation method thereof | |
| CN101560145A (en) | Method for separating chrysophanol and physcion by silica-gel column chromatography | |
| CN110187032A (en) | The measuring method of Pinoresinol diglucoside content in a kind of Eucommia ulmoides | |
| KR930701968A (en) | Anti-neoplastic agents extracted from plants and preparation method thereof |
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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20220118 |