CN117562939A - Sweet osmanthus standard active substance PHEG50 and preparation method and application thereof - Google Patents
Sweet osmanthus standard active substance PHEG50 and preparation method and application thereof Download PDFInfo
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- CN117562939A CN117562939A CN202311525358.1A CN202311525358A CN117562939A CN 117562939 A CN117562939 A CN 117562939A CN 202311525358 A CN202311525358 A CN 202311525358A CN 117562939 A CN117562939 A CN 117562939A
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- osmanthus
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- 239000013543 active substance Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 235000019083 Osmanthus fragrans Nutrition 0.000 title claims description 45
- 244000242564 Osmanthus fragrans Species 0.000 title claims description 45
- 239000012528 membrane Substances 0.000 claims abstract description 76
- QFRYQWYZSQDFOS-UHFFFAOYSA-N verbascoside Natural products CC1OC(COC2C(O)C(COC3OC(C(O)C(O)C3O)C(=O)O)OC(Oc4cc(O)cc5OC(=CC(=O)c45)c6ccc(O)c(O)c6)C2O)C(O)C(O)C1O QFRYQWYZSQDFOS-UHFFFAOYSA-N 0.000 claims abstract description 40
- 235000019082 Osmanthus Nutrition 0.000 claims abstract description 38
- 241000333181 Osmanthus Species 0.000 claims abstract description 38
- 229930185474 acteoside Natural products 0.000 claims abstract description 38
- FBSKJMQYURKNSU-ZLSOWSIRSA-N acteoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC(=O)\C=C\C=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@@H](OCCC=2C=C(O)C(O)=CC=2)[C@@H]1O FBSKJMQYURKNSU-ZLSOWSIRSA-N 0.000 claims abstract description 38
- FBSKJMQYURKNSU-UKQWSTALSA-N acteoside I Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)C=Cc4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O FBSKJMQYURKNSU-UKQWSTALSA-N 0.000 claims abstract description 38
- 238000001914 filtration Methods 0.000 claims abstract description 33
- 239000000706 filtrate Substances 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000001728 nano-filtration Methods 0.000 claims abstract description 25
- 239000000919 ceramic Substances 0.000 claims abstract description 21
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 19
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229930182470 glycoside Natural products 0.000 claims abstract description 11
- 239000000284 extract Substances 0.000 claims abstract description 10
- 150000002338 glycosides Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000002386 leaching Methods 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000000287 crude extract Substances 0.000 claims abstract 2
- 239000012465 retentate Substances 0.000 claims description 13
- 239000012466 permeate Substances 0.000 claims description 10
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims description 9
- 229960002303 citric acid monohydrate Drugs 0.000 claims description 9
- 238000007873 sieving Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- ILRCGYURZSFMEG-UHFFFAOYSA-N Salidroside Natural products OC1C(O)C(O)C(CO)OC1OCCC1=CC=C(O)C=C1 ILRCGYURZSFMEG-UHFFFAOYSA-N 0.000 claims description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
- 230000002929 anti-fatigue Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
- 235000011090 malic acid Nutrition 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- ILRCGYURZSFMEG-RQICVUQASA-N salidroside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OCCC1=CC=C(O)C=C1 ILRCGYURZSFMEG-RQICVUQASA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 230000036541 health Effects 0.000 claims description 2
- 239000011344 liquid material Substances 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 235000011167 hydrochloric acid Nutrition 0.000 claims 1
- 229960000443 hydrochloric acid Drugs 0.000 claims 1
- 229940099690 malic acid Drugs 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 229960004838 phosphoric acid Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 238000006317 isomerization reaction Methods 0.000 abstract description 4
- 230000015556 catabolic process Effects 0.000 abstract description 3
- 238000006731 degradation reaction Methods 0.000 abstract description 3
- FNMHEHXNBNCPCI-QEOJJFGVSA-N Isoacteoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](OCCC=2C=C(O)C(O)=CC=2)O[C@H](COC(=O)\C=C\C=2C=C(O)C(O)=CC=2)[C@H]1O FNMHEHXNBNCPCI-QEOJJFGVSA-N 0.000 abstract description 2
- FNMHEHXNBNCPCI-RYEKTNFUSA-N isoacteoside Natural products C[C@@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](COC(=O)C=Cc3ccc(O)c(O)c3)O[C@@H](OCCc4ccc(O)c(O)c4)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O FNMHEHXNBNCPCI-RYEKTNFUSA-N 0.000 abstract description 2
- 239000000419 plant extract Substances 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 description 19
- 241000628997 Flos Species 0.000 description 17
- 238000003756 stirring Methods 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- 230000009182 swimming Effects 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000207834 Oleaceae Species 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- -1 phenethyl alcohol glycoside Chemical class 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010019909 Hernia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000042430 Rhodiola rosea Species 0.000 description 1
- 235000003713 Rhodiola rosea Nutrition 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- XBJFCYDKBDVADW-UHFFFAOYSA-N acetonitrile;formic acid Chemical compound CC#N.OC=O XBJFCYDKBDVADW-UHFFFAOYSA-N 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G3/00—Glycosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- 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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- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses an osmanthus standard active substance PHEG50, a preparation method and application thereof, and particularly relates to the field of plant extracts. The preparation method of the osmanthus standard active substance PHEG50 comprises the following steps: mixing dried osmanthus flowers with water, adding acid to adjust the pH value, and leaching under a certain temperature condition to obtain an osmanthus crude extract; filtering the crude osmanthus extract to obtain filtrate, treating the filtrate by a ceramic membrane, an ultrafiltration membrane and a nanofiltration membrane, concentrating by an RO membrane, and drying to obtain the osmanthus standard active substance PHEG50. According to the scheme disclosed by the invention, the degradation and isomerization of the acteoside into the iso-acteoside are effectively reduced, the osmanthus standard active substance with high phenethyl alcohol total glycoside content is efficiently prepared, and the osmanthus standard active substance PHEG50 provided by the invention has the effect of obviously relieving physical fatigue.
Description
Technical Field
The invention belongs to the field of plant extracts, and particularly relates to an osmanthus standard active substance PHEG50, and a preparation method and application thereof.
Background
Osmanthus fragrans (Osmanthus fragrans (thunder.) lour.) are also called mountain and bay, which belong to the genus Oleaceae. The osmanthus fragrans have various varieties, about 154 varieties exist in the whole country, and the osmanthus fragrans are divided into 4 product groups, namely, four seasons osmanthus fragrans, silver osmanthus fragrans, gold osmanthus fragrans and red osmanthus fragrans.
The Chinese herbal medicine records: the flos Osmanthi Fragrantis is also called Oleaceae plant Oleaceae (Osmanthus fragrans). Harvesting when flowering for 9-10 months, removing impurities, drying in the shade, and hermetically storing. Sweet osmanthus flower, sweet in flavor and warm in nature. It enters lung, spleen and kidney meridians. Has effects of warming lung, resolving fluid retention, dispelling cold and relieving pain. Is mainly used for treating epigastric cold pain, cold hernia abdominal pain, amenorrhea and dysmenorrhea.
The invention patent CN116159089A, a phenethyl alcohol glycoside extract, a preparation method thereof and application thereof in anti-saccharification, discloses a preparation method for preparing 23-49% of phenethyl alcohol glycoside (PHEG) from osmanthus fragrans; the osmanthus fragrans extract prepared by the technical scheme has the advantages that the total phenylethanoid glycosides content is lower than 50%, the acteoside and the rhodiola rosea glycosides content are lower, and the total phenylethanoid glycosides content standard of the osmanthus fragrans standard active substance can not be met.
Ding Lixin and the like detect the content of salidroside and acteoside in different batches of osmanthus fragrans in different production places by using HPLC (journal of medicine analysis 2013,33 (5), 894-897), which shows that the osmanthus fragrans contains high content of salidroside and acteoside. Wu Gaili under the condition of researching pH5-7, boiling water is heated for 0-300min, and acteoside is degraded and isomerized into acteoside (Chinese herbal medicine 2022,53 (11), 3295-3305), which suggests that acteoside may be unstable under certain pH and temperature conditions.
Pharmacological literature shows that although acteoside and acteoside have similar effects of resisting oxidation, relieving physical fatigue and the like, activities of reducing uric acid and the like are obviously different. Therefore, optimizing the process conditions and inhibiting the isomerization of acteoside to acteoside are necessary.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to take osmanthus fragrans as a raw material, control reasonable parameter conditions, avoid degradation and isomerization of acteoside into iso-acteoside, and efficiently prepare the osmanthus fragrans standard active substance PHEG50 with the total phenylethanoid glycosides more than or equal to 50% by using a pure physical processing technology.
The first aspect of the invention provides a preparation method of an osmanthus standard active substance PHEG50, which comprises the following steps:
(1) Mixing dry osmanthus flowers with water, wherein the liquid-material ratio is more than or equal to 22 mL/1 g, adding acid to adjust the pH value to 3-4, and leaching for 1-4 h at 55-80 ℃ to obtain crude osmanthus extract;
(2) Filtering the crude osmanthus extract to obtain filtrate, concentrating and drying to obtain an osmanthus standard active substance PHEG50.
Preferably, the osmanthus fragrans dry flowers are osmanthus fragrans dry flowers, osmanthus fragrans dry flowers and/or osmanthus fragrans dry flowers.
Preferably, the dried osmanthus flowers obtained in the step (1) are crushed, sieved by a sieve with more than or equal to 10 meshes, and then mixed with water.
Preferably, the acid added in the step (1) for adjusting the pH value to 3-4 is at least one of citric acid monohydrate, malic acid, phosphoric acid, hydrochloric acid and acetic acid.
Preferably, the leaching time is 1-2 hours when the pH in the step (1) is 3-4 and the temperature is 60-80 ℃.
Preferably, in the step (2), the crude osmanthus fragrans extract is filtered by a ceramic membrane while the crude osmanthus fragrans extract is hot, so as to obtain ceramic membrane filtrate;
filtering the ceramic membrane filtrate by an ultrafiltration membrane of 5000-10000 daltons to remove macromolecules such as protein, polysaccharide and the like, thus obtaining an ultrafiltration membrane permeate;
filtering the ultrafiltration membrane permeate through a nanofiltration membrane of 200-250 daltons to remove monosaccharides, free amino acids and other small molecular components to obtain nanofiltration membrane retentate;
concentrating the nanofiltration membrane trapped fluid by an RO membrane, and drying to obtain the sweet osmanthus standard active substance PHEG50.
The second aspect of the invention provides an osmanthus standard active substance PHEG50, which is prepared by the preparation method.
Preferably, the sweet osmanthus standard active substance PHEG50 contains more than or equal to 50% of phenethyl alcohol total glycoside by mass percent.
Preferably, according to the mass percentage, acteoside in the sweet osmanthus standard active substance PHEG50 is more than or equal to 40%, rhodioside is more than or equal to 8%, and acteoside is less than or equal to 4%.
The third aspect of the invention provides application of the osmanthus standard active substance PHEG50 in preparing anti-fatigue medicines, foods and/or health products.
The fourth aspect of the invention provides an application of the sweet osmanthus standard active substance PHEG50 in preparing a detection standard.
The invention has the beneficial effects that:
1. by adopting the technical scheme provided by the invention, the degradation and isomerization of the acteoside into the acteoside are effectively reduced, the standard active substance PHEG50 of the osmanthus fragrans with the high phenethyl alcohol total glycoside being more than or equal to 50% is efficiently prepared, the acteoside in the phenethyl alcohol total glycoside is more than 40%, the rhodioside is more than 8%, and the acteoside is less than 4%.
2. The sweet osmanthus standard active substance PHEG50 provided by the invention has the obvious effect of relieving physical fatigue.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in the following in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The following description of the embodiments of the present invention will be presented in further detail with reference to the examples, which should be understood as being merely illustrative of the present invention and not limiting.
Preparation of test examples and extraction Rate detection
Pulverizing dried flos Osmanthi Fragrantis, sieving with 20 mesh sieve, weighing several parts, each part having 10.0g, respectively loading into 250ml conical flask, adding 220ml pure water, adding 165mg citric acid monohydrate to adjust pH to=3, or adding 27.5mg citric acid monohydrate to adjust pH to=4. No citric acid monohydrate is added, and the pH value of the osmanthus fragrans water extract is 6. Heating in water bath at different temperatures, intermittently stirring for 1min every 10min, extracting for 4 hr, sampling every 1 hr, filtering with 0.45 μm filter membrane, and detecting by HPLC. The extraction yields of acteoside and acteoside were calculated, both being isomers. Pulverizing dried flos Osmanthi Fragrantis, weighing 1.0g,50ml 70% ethanol water, ultrasonic extracting at room temperature for 45min, sampling, and detecting to obtain extractive solution as reference; the results of the measurements are shown in tables 2-4 below.
Table 1 extraction yields at different temperatures (55, 60, 70, 80, 90 ℃) at ph=3
Table 2 extraction yields at different temperatures (55, 60, 70, 80, 90 ℃) at ph=4
Table 3 extraction yields at different temperatures (55, 60, 70, 80, 90 ℃) at ph=6
HPLC detection method
The Detector was a 2998PDA Detector using a Waters e2695 type HPLC. The chromatographic column is Atlantis TM 3.5 μm, 4.6X1250 mm; the detection wavelengths are 327nm, 280nm, 254nm and 230nm, and the flow rate is 1ml/min; the column temperature is 30+/-2 ℃; mobile phase gradients are shown in table 4;
TABLE 4 Mobile phase gradient Meter
Time/min | 0.1% acetonitrile formate/% | 0.1% formic acid water/% |
0 | 20 | 80 |
10 | 35 | 65 |
12 | 20 | 80 |
15 | 20 | 80 |
Test example result analysis:
table 2 experimental data shows that: at ph=3, the extraction is carried out at a temperature below 60 ℃, the acteoside is stable, even a small amount of acteoside is converted into acteoside, but the temperature is too low, the extraction time is long, and the extraction efficiency is low. Extracting at 70-80deg.C for 1 hr to obtain acteoside which is stable and not isomerized to acteoside, and extracting for more than 2 hr to obtain acteoside which is isomerized to acteoside. The extraction temperature is over 90 ℃, and the acteoside is obviously isomerized into acteoside.
Table 3 experimental data shows that: at ph=4, the extraction is carried out for 1h at a temperature below 60 ℃, the acteoside is stable, and the acteoside is not isomerized into the acteoside. Extracting at a temperature lower than 55deg.C for 3 hr, and extracting acteoside with extraction yield lower than 80%. The temperature is over 70 ℃, and the acteoside is obviously isomerized into acteoside.
Table 4 experimental data shows that: extracting at above 55deg.C without adjusting acid and pH=6 to obtain acteoside. The isomerism proportion is obviously increased above 70 ℃.
Examples and comparative examples
Preparation of example 1
3000g of dried flos eryngii, and crushing and sieving with a 10-mesh sieve to obtain dried flos eryngii powder for later use;
adding pure water 45L into a 100L extraction barrel, adding citric acid monohydrate, adjusting the pH to be 3, heating to 80 ℃, adding dry osmanthus flower powder, and intermittently stirring and extracting for 60min; filtering with 100 mesh stainless steel screen, adding the obtained residue into 30L water solution with pH=3, extracting at 80deg.C under intermittent stirring for 30min, and filtering with 100 mesh screen.
Combining the two extracted filtrate, filtering the ceramic membrane while the filtrate is hot, filtering the ceramic membrane filtrate by using an 10000 dalton ultrafiltration membrane, passing the ultrafiltration membrane permeate through a 200 dalton nanofiltration membrane, and collecting nanofiltration membrane retentate; the retentate from the nanofiltration membrane of 200 daltons was concentrated to 25% solids by RO membrane and dried by vacuum concentration under reduced pressure to give the sample of example 1.
Example 2 preparation
3000g of dried flos eryngii, and crushing and sieving with a 10-mesh sieve to obtain dried flos eryngii powder for later use;
adding pure water 45L into a 100L extraction barrel, adding ascorbic acid (VC), adjusting the pH to be 4, heating to 60 ℃, adding dry flos eryngii powder, and intermittently stirring and extracting for 60min; filtering with 100 mesh stainless steel screen, adding the obtained residue into 30L water solution with pH=4, extracting at 60deg.C under intermittent stirring for 30min, and filtering with 100 mesh screen.
Combining the two extracted filtrate, filtering the ceramic membrane while the filtrate is hot, filtering the ceramic membrane filtrate by using an 10000 dalton ultrafiltration membrane, passing the ultrafiltration membrane permeate through a 200 dalton nanofiltration membrane, and collecting nanofiltration membrane retentate; the retentate from the nanofiltration membrane of 200 daltons was concentrated to 25% solids by RO membrane and concentrated under reduced pressure to give the sample of example 2.
Example 3 preparation
3000g of dried golden osmanthus flowers, and crushing and sieving the dried golden osmanthus flowers with a 10-mesh sieve to obtain dried golden osmanthus flowers powder for later use;
adding pure water 45L into a 100L extraction barrel, adding malic acid, adjusting the pH to be 3, heating to 70 ℃, adding dried golden osmanthus flower powder, and intermittently stirring and extracting for 90min; filtering with 100 mesh stainless steel screen, adding the obtained residue into 30L water solution with pH=3, extracting at 70deg.C under intermittent stirring for 30min, and filtering with 100 mesh screen.
Combining the two extracted filtrate, filtering the ceramic membrane while the filtrate is hot, filtering the ceramic membrane filtrate by using a 5000 dalton ultrafiltration membrane, passing the ultrafiltration membrane permeate through a 250 dalton nanofiltration membrane, and collecting nanofiltration membrane retentate; the retentate from the 250 dalton nanofiltration membrane was concentrated to a solids content of 30% by passing through an RO membrane and spray dried to give the sample of example 3.
Example 4 preparation
3000g of dried silver osmanthus flowers, and crushing and sieving the dried silver osmanthus flowers with a 10-mesh sieve to obtain dried silver osmanthus flowers powder for later use;
adding pure water 45L into a 100L extraction barrel, adding citric acid monohydrate, adjusting the pH to be 3, heating to 60 ℃, adding dried silver osmanthus flower powder, and intermittently stirring and extracting for 45min; filtering with 100 mesh stainless steel screen, adding the obtained residue into 30L water solution with pH=3, extracting at 60deg.C under intermittent stirring for 15min, and filtering with 100 mesh screen.
Combining the two extracted filtrate, filtering the ceramic membrane while the filtrate is hot, filtering the ceramic membrane filtrate by using a 5000 dalton ultrafiltration membrane, passing the ultrafiltration membrane permeate through a 200 dalton nanofiltration membrane, and collecting nanofiltration membrane retentate; the 200 dalton nanofiltration membrane retentate was concentrated to 25% solids by RO membrane and spray dried to give the sample of example 4.
Preparation of comparative example 1
3000g of dried flos eryngii, and crushing and sieving the dried flos eryngii with a 10-mesh sieve to obtain the dried flos eryngii powder for later use.
Adding pure water 45L into a 100L extraction barrel, heating to 80 ℃, adding dried eryngii flower powder, and intermittently stirring and extracting for 60min; filtering with 100 mesh stainless steel screen, adding the obtained residue into 30L pure water, extracting at 80deg.C under intermittent stirring for 30min, and filtering with 100 mesh screen.
Combining the two extracted filtrate, filtering the ceramic membrane while the filtrate is hot, filtering the ceramic membrane filtrate by using an 10000 dalton ultrafiltration membrane, passing the ultrafiltration membrane permeate through a 300 dalton nanofiltration membrane, and collecting nanofiltration membrane retentate; and concentrating the 300 dalton nanofiltration membrane trapped liquid to 25% of solid content through an RO membrane, and freeze-drying to obtain a sample of comparative example 1.
Preparation of comparative example 2
3000g of dried flos eryngii, and crushing and sieving the dried flos eryngii with a 10-mesh sieve to obtain the dried flos eryngii powder for later use.
Adding pure water 45L into a 100L extraction barrel, adding citric acid monohydrate, adjusting the pH to be 4, heating to 80 ℃, adding dry osmanthus flower powder, and intermittently stirring and extracting for 60min; filtering with 100 mesh stainless steel screen, adding the obtained residue into 30L water solution with pH=4, extracting at 80deg.C under intermittent stirring for 30min, and filtering with 100 mesh screen.
Combining the two extracted filtrate, filtering the ceramic membrane while the filtrate is hot, filtering the ceramic membrane filtrate by using an 10000 dalton ultrafiltration membrane, passing the ultrafiltration membrane permeate through a 200 dalton nanofiltration membrane, and collecting nanofiltration membrane retentate; and concentrating the retentate of the nanofiltration membrane of 200 daltons by using an RO membrane until the solid content is 25%, and spray-drying to obtain a sample of comparative example 2.
Preparation of comparative example 3
3000g of dried flos eryngii, and crushing and sieving the dried flos eryngii with a 10-mesh sieve to obtain the dried flos eryngii powder for later use.
Adding pure water 45L into a 100L extraction barrel, adding citric acid monohydrate, adjusting the pH to be 3, heating to 80 ℃, adding dry osmanthus flower powder, and intermittently stirring and extracting for 60min; filtering with 100 mesh stainless steel screen, adding the obtained residue into 30L water solution with pH=3, extracting at 80deg.C under intermittent stirring for 30min, and filtering with 100 mesh screen.
And (3) combining the two extracted filtrate, filtering the ceramic membrane while the ceramic membrane is hot, concentrating the obtained filtrate by using an RO membrane until the solid content is 25%, and spray-drying to obtain a sample of comparative example 3.
Sample extraction rates and analysis of the main component content of the samples of examples and comparative examples are shown in Table 5:
TABLE 5HPLC detection results
Anti-fatigue mouse experiment
Sample to be measured: PHEG50 and normal saline prepared in example 1;
40 healthy male SPF-class mice of 5 weeks old of Kunming species, with a weight of 29.00+ -1.65 g, were randomly divided into a sports group, PHEG50 low dose (15 mg/kg, ratio of sample mass to mouse weight to be measured) +sports group, a medium dose (30 mg/kg) +sports group, and a high dose (60 mg/kg) +sports group after 2 days of adaptive feeding of experimental animals. 10 animals in each group eat and drink freely at 18-24 ℃. PHEG50 was dissolved in normal saline and infused 1 time per day. Normal control group, exercise group, etc. the normal saline perfused the stomach for 4 weeks. Mice were observed daily and recorded for general status, weighing once a week.
Except for the normal control group, the water was not subjected to load swimming for 3 hours after stomach irrigation, at a water temperature of 25 ℃ and a water depth of 40cm. 30min per day at week 1, 60min per day at week 2, 90min per day at week 3, 120min per day at week 4, 6 days per week for 4 weeks. On day 29, all but the normal control group were subjected to one-time exhaustion swimming and exhaustion time was recorded.
TABLE 6 weight and time of life of mice in each group
Group of | Weight/g before experiment | Week 4 weight/g | Swimming time/min for exhaustion |
Sports group | 29.36±1.28 | 31.19±2.36# | 78.60±26.38* |
Low dose group | 29.47±1.34 | 32.37±2.19# | 118.32±29.27* |
Medium dose group | 29.24±1.27 | 32.45±2.28# | 145.11±30.25* |
High dose group | 29.35±1.36 | 32.68±2.44# | 157.24±35.48* |
Note that: "#" is P < 0.01; ". Times" means 0.01 < P < 0.05.
Analysis of results:
compared with a sports group, the low, medium and high three-dose PHEG50+ sports group is shown by the experiment of the exhaustion swimming of the mice, the time of the exhaustion swimming is obviously prolonged, and the time of the exhaustion swimming is obviously prolonged along with the increase of the dose, so that the sweet osmanthus standard active PHEG50 provided by the invention has the effect of obviously relieving physical fatigue.
Finally, it should be noted that: the foregoing description is only a preferred embodiment of the present invention, and the present invention is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present invention has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The preparation method of the sweet osmanthus standard active substance PHEG50 is characterized by comprising the following steps of:
(1) Mixing dry osmanthus flowers with water, wherein the liquid-material ratio is more than or equal to 22 mL/1 g, adding acid to adjust the pH value to 3-4, and leaching for 1-4 h at 55-80 ℃ to obtain crude osmanthus extract;
(2) Filtering the crude osmanthus extract to obtain filtrate, concentrating and drying to obtain an osmanthus standard active substance PHEG50.
2. The method for preparing the sweet osmanthus standard active substance PHEG50 according to claim 1, wherein the sweet osmanthus dry flowers are dried osmanthus flowers, dried osmanthus flowers and/or dried osmanthus flowers;
and (3) crushing the dried osmanthus flowers in the step (1), sieving with a sieve with a mesh size of more than or equal to 10, and mixing with water.
3. The method for preparing sweet osmanthus standard active substance PHEG50 according to claim 1, wherein the acid in the step (1) is at least one of citric acid monohydrate, malic acid, ascorbic acid, phosphoric acid, hydrochloric acid and acetic acid.
4. The method for preparing sweet osmanthus standard active substance PHEG50 according to claim 1, wherein the leaching time is 1-2 h when the pH in the step (1) is 3-4 and the temperature is 60-80 ℃.
5. The method for preparing the sweet osmanthus standard active substance PHEG50 according to claim 1, wherein the sweet osmanthus crude extract in the step (2) is filtered by a ceramic membrane when being hot, so as to obtain ceramic membrane filtrate;
the ceramic membrane filtrate is filtered by an ultrafiltration membrane of 5000-10000 daltons to obtain an ultrafiltration membrane permeate;
the ultrafiltration membrane permeate is filtered by a nanofiltration membrane of 200-250 daltons to obtain nanofiltration membrane retentate;
concentrating the nanofiltration membrane trapped fluid by an RO membrane, and drying to obtain the sweet osmanthus standard active substance PHEG50.
6. An osmanthus standard active substance PHEG50, which is characterized by being prepared by the preparation method according to any one of claims 1-5.
7. The osmanthus standard active substance PHEG50 according to claim 6, wherein the total glycosides of phenethyl alcohol are contained in a mass percentage of not less than 50%.
8. The sweet osmanthus standard active substance PHEG50 according to claim 6 or 7, wherein the acteoside in the sweet osmanthus standard active substance PHEG50 is more than or equal to 40% and the salidroside is more than or equal to 8% and the acteoside is more than or equal to 4% in percentage by mass.
9. Use of the sweet osmanthus standard active substance PHEG50 according to any of claims 6-8 for preparing anti-fatigue drugs, foods and/or health products.
10. Use of the sweet osmanthus standard active substance PHEG50 according to any one of claims 6-8 in the preparation of a detection standard.
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