CN117327039A - Extraction method of luteolin for treating acute and chronic rhinitis - Google Patents
Extraction method of luteolin for treating acute and chronic rhinitis Download PDFInfo
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- CN117327039A CN117327039A CN202311115817.9A CN202311115817A CN117327039A CN 117327039 A CN117327039 A CN 117327039A CN 202311115817 A CN202311115817 A CN 202311115817A CN 117327039 A CN117327039 A CN 117327039A
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- enzymolysis
- luteolin
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- 238000000605 extraction Methods 0.000 title claims abstract description 52
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 title claims abstract description 49
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 title claims abstract description 49
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 235000009498 luteolin Nutrition 0.000 title claims abstract description 48
- 206010039083 rhinitis Diseases 0.000 title claims abstract description 21
- 201000009151 chronic rhinitis Diseases 0.000 title claims abstract description 11
- 230000001154 acute effect Effects 0.000 title claims abstract description 10
- 201000009240 nasopharyngitis Diseases 0.000 title claims abstract description 10
- 102000004190 Enzymes Human genes 0.000 claims abstract description 40
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
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- 239000002904 solvent Substances 0.000 claims abstract description 26
- 239000012043 crude product Substances 0.000 claims abstract description 24
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- 239000000203 mixture Substances 0.000 claims description 20
- 239000000600 sorbitol Substances 0.000 claims description 20
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 19
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- 241001529821 Agastache Species 0.000 claims description 15
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- 102000012479 Serine Proteases Human genes 0.000 claims description 11
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940089639 cornsilk Drugs 0.000 description 3
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000019835 bromelain Nutrition 0.000 description 2
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
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- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 108010059892 Cellulase Proteins 0.000 description 1
- 244000304337 Cuminum cyminum Species 0.000 description 1
- 235000007129 Cuminum cyminum Nutrition 0.000 description 1
- 108090000270 Ficain Proteins 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- 229960002504 capsaicin Drugs 0.000 description 1
- 235000017663 capsaicin Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
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- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 235000019836 ficin Nutrition 0.000 description 1
- POTUGHMKJGOKRI-UHFFFAOYSA-N ficin Chemical compound FI=CI=N POTUGHMKJGOKRI-UHFFFAOYSA-N 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- -1 flavonoid compound Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
- 238000000874 microwave-assisted extraction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 238000002137 ultrasound extraction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention belongs to the field of active ingredient extraction processes, and particularly relates to an extraction method and application of luteolin for treating acute and chronic rhinitis. The method comprises the steps of adding patchouli into wild chrysanthemum flower, mixing, adding a solvent for soaking, extracting to obtain an extracting solution, and adding enzyme 1 into the extracting solution for enzymolysis to obtain an enzymolysis solution; purifying the enzymolysis liquid by a polyamide resin column, washing with water, adding ethyl acetate-acetone solution for eluting, collecting eluent, and spin-drying to obtain a crude product; and finally, adding alkaline ethanol solution into the crude product, adding enzyme 2 for enzymolysis, adding hydrochloric acid for crystallization and suction filtration. The extraction process of the invention is mild, the extraction rate and purity of luteolin are high, and the luteolin extracted by the invention can be used for treating acute and chronic rhinitis.
Description
Technical Field
The invention belongs to the field of active ingredient extraction processes, and particularly relates to an extraction method of luteolin for treating acute and chronic rhinitis.
Background
Luteolin is a natural flavonoid compound, has a yellow needle-like crystal with a melting point of 228-230 ℃ and chemical name of 3,4,5, 7-tetrahydroxy flavone, is widely existing in various plants in nature, and is often used for treating diseases and has various pharmacological effects. Chemical analysis research shows that luteolin under the condition of equimolar concentration has the strongest antioxidant activity compared with quercetin and capsaicin; the results of pharmacological and clinical experiments also show that luteolin has obvious effect of treating chronic rhinitis, has obvious antibacterial and antiviral effects, and has the effects of reducing blood fat, cholesterol and the like.
Luteolin is a compound of polyphenol hydroxyl, and has relatively high lattice energy and relatively poor lipophilic and hydrophilic properties due to intermolecular forces among the hydroxyl groups; its special structure results in its low solubility in a variety of solvents, which presents a certain challenge for its preparation. The existing semisynthesis process and full synthesis process of luteolin are complex in operation and high in cost; extraction from natural plants is the best way to obtain luteolin. Research, innovation and effective extraction process are continuous pursuits of cumin by the person skilled in the art.
The Chinese patent application CN105566273A discloses a method for extracting luteolin from corn silk, which takes corn silk as a raw material and adopts microwave-ultrasonic to assist in extracting the luteolin from the corn silk, wherein the extraction technology comprises two stages: the first stage adopts microwave oven microwave extraction, and the later stage adopts ultrasonic cleaner ultrasonic extraction.
Another chinese patent application CN107382937a discloses a method for extracting luteolin from luteolin, which comprises the steps of pulverizing, extracting, filtering, acid hydrolysis, centrifugal separation, decolorizing and purifying with neutral alumina, decolorizing with activated carbon, concentrating and crystallizing, etc. In the extraction process, ultrasonic wave combined high-voltage pulse electric field treatment and microwave combined high-voltage pulse electric field treatment are adopted, the obtained extracting solution is hydrolyzed by adopting acid and high-frequency electromagnetic wave treatment, and finally the obtained hydrolysate is subjected to centrifugal separation, neutral alumina decoloration purification, activated carbon decoloration, concentration crystallization, centrifugation, recrystallization and other processes in sequence, so that the extraction rate and purity of the finished luteolin are improved.
The prior art has explored the extraction of luteolin, but the extraction rate and purity are not high, or the process is complex, the universality is poor, the luteolin is difficult to popularize in large production, the luteolin plants are less planted in China, and the supply of the luteolin is limited; the pure luteolin product is extracted from the wild chrysanthemum flower with higher content and the patchouli planted in large area, and the prior art has not been disclosed.
Disclosure of Invention
Aiming at the defects, the invention provides an extraction method of luteolin for treating acute and chronic rhinitis, which has high extraction rate and high purity.
In order to solve the technical problems, the invention adopts the following technical scheme:
a method for extracting luteolin for treating acute and chronic rhinitis comprises the following steps:
(1) Adding herba Agastaches into flos Chrysanthemi Indici, mixing, soaking in solvent, and extracting to obtain extractive solution;
(2) Adding enzyme 1 into the extracting solution for enzymolysis to obtain an enzymolysis solution;
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, adding ethyl acetate-acetone solution for eluting, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding alkaline ethanol solution into the crude product, adding enzyme 2 for enzymolysis, adding hydrochloric acid for crystallization and suction filtration.
Preferably, in the step (1), the mass ratio of the wild chrysanthemum to the patchouli is 1:1.5-2.
Preferably, the solvent in the step (1) is a mixture of sorbitol, polyethylene glycol 600 tartaric acid and water, and the mass ratio of the sorbitol, the polyethylene glycol 600, the tartaric acid and the water is 0.01-0.05:0.01-0.05:0.01-0.03:1.
preferably, the temperature of the extraction in the step (1) is 60-70 ℃, the extraction time is 0.5-2h, and the extraction times are 1-3 times.
Preferably, the enzyme in step (2) comprises a mass ratio of 1:1-5, wherein the enzyme is used in an amount of 0.05-0.1% of the mass of the extract.
Preferably, in the step (2), the enzymolysis temperature is 55-70 ℃, the enzymolysis pH is 5.0-7.5, and the enzymolysis time is 2-4h.
Preferably, the polyamide resin in step (3) has a particle size of 60 to 80 mesh; the volume ratio of the ethyl acetate to the acetone is 1:0.2-0.5, the dosage is 5-8 times of the column volume, and the eluting flow rate is 1-1.5mL/min.
Preferably, in the step (4), the alkaline ethanol solution is 1-5% ammonia ethanol solution, and the mass volume ratio of the crude product to the alkaline ethanol is 1:1-2.
Preferably, in the step (4), the enzyme 2 is a mixture of keratinase, serine protease and aminopeptidase with a mass ratio of 1:0.5-1:0.5-1, the enzymolysis time is 2-4 hours, and the pH is adjusted to 1.0-1.5 after hydrochloric acid is added.
The invention also aims to provide the application of the luteolin extracted by the extraction method in preparing medicines for treating acute and chronic rhinitis.
It is still another object of the present invention to provide the use of the above extraction method for the extraction of luteolin.
Compared with the prior art, the invention has the following positive and beneficial effects:
(1) The invention promotes the dissolution of the active ingredients through the soaking and extraction of the specific solvent;
(2) The luteolin can be extracted more completely by further adopting specific enzyme for enzymolysis, and the luteolin can be separated from a complex combined with saccharides, proteins and the like by adding specific enzyme 2 for enzymolysis after purification, so that the extraction rate of the luteolin is improved.
(3) The invention adopts the composite resin for purification and adopts the specific solvent for re-dissolution and crystallization, thereby obviously synergistically improving the extraction purity of luteolin.
(4) Through extensive researches, the invention discovers that the patchouli and the wild chrysanthemum are extracted together and can also promote the extraction of luteolin.
Detailed Description
The present invention will be described in further detail with reference to the following examples, which are not intended to limit the present invention, but are merely illustrative of the present invention. The experimental methods used in the following examples are not specifically described, but the experimental methods in which specific conditions are not specified in the examples are generally carried out under conventional conditions, and the materials, reagents, etc. used in the following examples are commercially available unless otherwise specified.
Wherein the cellulase supplier is a summer Cheng Mei preparation; the saccharifying enzyme supplier is Nanning east Henghua biological technology Limited liability company;
the supplier of keratinase is Shandong Fengtai technology biosciences, the supplier of serine proteinase is Siam Dall technology biosciences, and the supplier of aminopeptidase, bromelain and papain is Nanning Dong Henghua channel biosciences, inc.; ficin is available from commercial suppliers
Example 1
The extraction method of luteolin in the embodiment comprises the following steps:
(1) Adding herba Agastaches into flos Chrysanthemi Indici, wherein the mass ratio of herba Agastaches to flos Chrysanthemi Indici is 1:1, mixing, adding a solvent, soaking for 30min, and extracting at 65 ℃ for 1h to obtain an extracting solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol to the tartaric acid to the water is 0.02:0.02:0.02:1.
(2) Adding 0.08% enzyme into the extract, and performing enzymolysis at 55deg.C and pH of 7.5 for 2 hr to obtain enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 3 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting by using ethyl acetate-acetone solution with the volume ratio of 5BV of 1:0.3, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 1 time of 1-5% ammonia water ethanol solution into the crude product, adding the mixture of keratinase, serine protease and aminopeptidase with the mass ratio of 1:0.5:0.5, carrying out enzymolysis for 2 hours at 30 ℃ and pH of 7.0, adding hydrochloric acid to adjust the pH to 1.0, stirring, crystallizing and filtering to obtain the product.
Example 2
The extraction method of luteolin in the embodiment comprises the following steps:
(1) Adding herba Agastaches into flos Chrysanthemi Indici, wherein the mass ratio of herba Agastaches to flos Chrysanthemi Indici is 1:2, mixing, adding solvent, soaking for 30min, and extracting at 70deg.C for 2 hr to obtain extractive solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol to the tartaric acid to the water is 0.01:0.01:0.01:1.
(2) Adding 0.05% enzyme into the extract, and performing enzymolysis at 55deg.C and pH of 7.5 for 4 hr to obtain enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 5 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting by using ethyl acetate-acetone solution with the volume ratio of 5BV of 1:0.2, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 2 times of 5% ammonia water ethanol solution into the crude product, adding a mixture of keratinase, serine protease and aminopeptidase with the mass ratio of 1:0.5:0.5, carrying out enzymolysis for 3 hours at 30 ℃ and pH7.0, adding hydrochloric acid to adjust the pH to 1.0, stirring, crystallizing and carrying out suction filtration to obtain the finished product.
Example 3
(1) The extraction method of luteolin in the embodiment comprises the following steps: adding herba Agastaches into flos Chrysanthemi Indici, wherein the mass ratio of herba Agastaches to flos Chrysanthemi Indici is 1:2, mixing, adding solvent, soaking for 30min, extracting at 60deg.C for 0.5 hr for 3 times to obtain extractive solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol to the tartaric acid to the water is 0.05:0.05:0.03:1.
(2) Adding 0.1% enzyme into the extract, and performing enzymolysis for 2 hours at 70 ℃ and pH of 7.5 to obtain an enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 1 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting by using ethyl acetate-acetone solution with the volume ratio of 5BV of 1:0.5, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 1 times of 1% ammonia water ethanol solution into the crude product, adding a mixture of keratinase, serine proteinase and aminopeptidase with the mass ratio of 1:1:1, carrying out enzymolysis for 4 hours at 30 ℃, adding hydrochloric acid to adjust the pH value to 1.5, stirring, crystallizing and carrying out suction filtration to obtain the finished product. Wherein the keratinase supplier is Shandong Fengtai Biotechnology Co., ltd, the serine proteinase supplier is Sidamer biological technology Co., and the aminopeptidase supplier is Nanning Henghua biological technology Co., ltd.
Comparative example 1
This comparative example differs from example 1 in that the solvent of step (1) is different; the remainder remained the same as in example 1.
(1) Adding herba Agastaches into flos Chrysanthemi Indici, wherein the mass ratio of herba Agastaches to flos Chrysanthemi Indici is 1:1, mixing, adding a solvent, soaking for 30min, and extracting at 65 ℃ for 1h to obtain an extracting solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol 600 to the citric acid to the water is 0.02:0.02:0.02:1.
(2) Adding 0.08% enzyme into the extract, and performing enzymolysis at 55deg.C and pH of 7.5 for 2 hr to obtain enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 3 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting by using ethyl acetate-acetone solution with the volume ratio of 5BV of 1:0.3, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 1 times of 1-5% ammonia water ethanol solution into the crude product, adding the mixture of keratinase, serine protease and aminopeptidase with the mass ratio of 1:0.5:0.5, carrying out enzymolysis for 2 hours at 30 ℃, adding hydrochloric acid to adjust the pH value to 1.0, stirring, crystallizing and filtering.
Comparative example 2
This comparative example differs from example 1 in that the enzyme of step (2) is different; the remainder remained the same as in example 1.
(1) Adding herba Agastaches into flos Chrysanthemi Indici, wherein the mass ratio of herba Agastaches to flos Chrysanthemi Indici is 1:1, mixing, adding a solvent, soaking for 30min, and extracting at 65 ℃ for 1h to obtain an extracting solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol to the tartaric acid to the water is 0.02:0.02:0.02:1.
(2) Adding 0.08% enzyme into the extract, and performing enzymolysis at 55deg.C and pH of 7.5 for 2 hr to obtain enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 3 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting by using ethyl acetate-acetone solution with the volume ratio of 5BV of 1:0.3, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 1 time of 1-5% ammonia water ethanol solution into the crude product, adding the mixture of bromelain, papain and aminopeptidase with the mass ratio of 1:0.5:0.5, carrying out enzymolysis for 2 hours at 30 ℃, adding hydrochloric acid to adjust the pH value to 1.0, stirring, crystallizing and carrying out suction filtration to obtain the finished product.
Comparative example 3
This comparative example differs from example 1 in that the purification step of step (3) is different; the remainder remained the same as in example 1.
(1) Adding herba Agastaches into flos Chrysanthemi Indici, wherein the mass ratio of herba Agastaches to flos Chrysanthemi Indici is 1:1, mixing, adding a solvent, soaking for 30min, and extracting at 65 ℃ for 1h to obtain an extracting solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol to the tartaric acid to the water is 0.02:0.02:0.02:1.
(2) Adding 0.08% enzyme into the extract, and performing enzymolysis at 55deg.C and pH of 7.5 for 2 hr to obtain enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 3 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting with 5BV ethyl acetate solution, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 1 times of 1-5% ammonia water ethanol solution into the crude product, adding the mixture of keratinase, serine protease and aminopeptidase with the mass ratio of 1:0.5:0.5, carrying out enzymolysis for 2 hours at 30 ℃, adding hydrochloric acid to adjust the pH value to 1.0, stirring, crystallizing and filtering.
Comparative example 4
The comparative example is an extraction of Pogostemon cablin, the amount of which is the same as in example 1.
(1) Soaking herba Agastaches in solvent for 30min, and extracting at 65deg.C for 1 hr to obtain extractive solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol to the tartaric acid to the water is 0.02:0.02:0.02:1.
(2) Adding 0.08% enzyme into the extract, and performing enzymolysis at 55deg.C and pH of 7.5 for 2 hr to obtain enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 3 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting by using ethyl acetate-acetone solution with the volume ratio of 5BV of 1:0.3, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 1 times of 1-5% ammonia water ethanol solution into the crude product, adding the mixture of keratinase, serine protease and aminopeptidase with the mass ratio of 1:0.5:0.5, carrying out enzymolysis for 2 hours at 30 ℃, adding hydrochloric acid to adjust the pH value to 1.0, stirring, crystallizing and filtering.
Comparative example 5
The comparative example was an extraction of wild chrysanthemum flower, and the amount of wild chrysanthemum flower was the same as in example 1.
(1) Soaking flos Chrysanthemi Indici in solvent for 30min, and extracting at 65deg.C for 1 hr to obtain extractive solution;
wherein the solvent is a mixture of sorbitol, polyethylene glycol 600, tartaric acid and water, and the mass ratio of the sorbitol to the polyethylene glycol to the tartaric acid to the water is 0.02:0.02:0.02:1.
(2) Adding 0.08% enzyme into the extract, and performing enzymolysis at 55deg.C and pH of 7.5 for 2 hr to obtain enzymolysis solution;
the enzyme is prepared from the following components in percentage by mass: 3 and a saccharifying enzyme.
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, eluting by using ethyl acetate-acetone solution with the volume ratio of 5BV of 1:0.3, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding 1 times of 1-5% ammonia water ethanol solution into the crude product, adding the mixture of keratinase, serine protease and aminopeptidase with the mass ratio of 1:0.5:0.5, carrying out enzymolysis for 2 hours at 30 ℃, adding hydrochloric acid to adjust the pH value to 1.0, stirring, crystallizing and filtering.
Experiment one, the extraction rate and purity of luteolin extracted by the invention are detected
HPLC was used to determine luteolin content:
preparation of test solution: 1g of a sample is precisely weighed, 25mL of methanol is added for ultrasonic dissolution, filtration and concentration are carried out, the volume is fixed to a volumetric flask of 5mL, and a filter membrane of 0.45 mu m is used for filtration, thus obtaining a sample solution.
Preparing a reference substance solution: precisely weighing a proper amount of luteolin reference substance, dissolving with methanol to obtain a reference substance solution of luteolin 1 μg/mL for use.
(1) The chromatographic conditions are as follows:
the octadecylsilane chemically bonded silica column is a chromatographic column;
acetonitrile-0.5% phosphoric acid solution (volume ratio is 50:50) is used as a mobile phase;
column temperature is 30 ℃; the detection wavelength is 285nm;
the flow rate is 1.0mL/min; the sample injection amount is 20 mu L;
calculating the content of luteolin in the product according to an external standard method.
Extraction ratio% = weight of powder crystallized and dried/total mass of pogostemon cablin and wild chrysanthemum 100%;
purity% = luteolin content per weight of crystalline dry powder 100%.
The samples prepared in examples 1 to 3 and comparative examples 1 to 5 according to the present invention were measured for luteolin content, and the extraction yield and purity thereof were as shown in Table 1 below.
TABLE 1
| Extraction yield% | Purity% | |
| Example 1 | 0.61 | 98.6 |
| Example 2 | 0.63 | 97.2 |
| Example 3 | 0.59 | 98.0 |
| Comparative example 1 | 0.48 | 90.1 |
| Comparative example 2 | 0.38 | 94.5 |
| Comparative example 3 | 0.55 | 83.2 |
| Comparative example 4 | 0.01 | 97.4 |
| Comparative example 5 | 0.52 | 98.5 |
The result shows that the extraction rate of luteolin prepared by the extraction method is higher than the sum of luteolin extracted from patchouli and wild chrysanthemum, which indicates that chemical components contained in the patchouli and the wild chrysanthemum are mutually promoted, and the extraction rate of luteolin is improved. Meanwhile, the invention adopts secondary enzymolysis and specific solvent to extract the medicinal materials, separates luteolin from the compound combined with sugar, protein and the like, and further improves the extraction rate and purity of the luteolin.
The foregoing examples illustrate only a few embodiments of the invention and are described in detail herein without thereby limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (10)
1. The extraction method of luteolin for treating acute and chronic rhinitis is characterized by comprising the following steps:
(1) Adding herba Agastaches into flos Chrysanthemi Indici, mixing, soaking in solvent, and extracting to obtain extractive solution;
(2) Adding enzyme 1 into the extracting solution for enzymolysis to obtain an enzymolysis solution;
(3) Purifying the enzymolysis liquid by a polyamide resin column, washing with water, adding ethyl acetate-acetone solution for eluting, collecting eluent, and spin-drying to obtain a crude product;
(4) Adding alkaline ethanol solution into the crude product, adding enzyme 2 for enzymolysis, adding hydrochloric acid for crystallization and suction filtration.
2. The extraction method according to claim 1, wherein the mass ratio of the wild chrysanthemum flower to the patchouli in the step (1) is 1:1.5-2.
3. The extraction method according to claim 1, wherein the solvent in the step (1) is a mixture of sorbitol, polyethylene glycol 600 tartaric acid and water, and the mass ratio of sorbitol, polyethylene glycol 600, tartaric acid and water is 0.01-0.05:0.01-0.05:0.01-0.03:1.
4. the extraction method according to claim 1, wherein the extraction temperature in step (1) is 60-70 ℃, the extraction time is 0.5-2h, and the number of extraction times is 1-3.
5. The extraction method according to claim 1, wherein the enzyme in step (2) comprises a mass ratio of 1:1-5, wherein the enzyme is used in an amount of 0.05-0.1% of the mass of the extract.
6. The extraction method according to claim 1, wherein the enzymolysis temperature in step (2) is 55-70 ℃, the enzymolysis pH is 5.0-7.5, and the enzymolysis time is 2-4h.
7. The extraction method according to claim 1, wherein the polyamide resin in step (3) has a particle size of 60 to 80 mesh; the volume ratio of the ethyl acetate to the acetone is 1:0.2-0.5, the dosage is 5-8 times of the column volume, and the eluting flow rate is 1-1.5mL/min.
8. The extraction method according to claim 1, wherein the alkaline ethanol solution in the step (4) is 1-5% aqueous ammonia ethanol solution, and the mass-volume ratio of the crude product to the alkaline ethanol is 1:1-2.
9. The method according to claim 1, wherein in the step (4), the enzyme 2 is a mixture of keratinase, serine protease and aminopeptidase in a mass ratio of 1:0.5-1:0.5-1, the enzymolysis time is 2-4 hours, and the pH is adjusted to 1.0-1.5 after adding hydrochloric acid.
10. Use of luteolin extracted by the extraction method of any one of claims 1-9 in the preparation of a medicament for treating acute and chronic rhinitis.
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