CN106977559A - A kind of method of separating-purifying punicalagins and gallic acid simultaneously from granatum - Google Patents
A kind of method of separating-purifying punicalagins and gallic acid simultaneously from granatum Download PDFInfo
- Publication number
- CN106977559A CN106977559A CN201710184111.6A CN201710184111A CN106977559A CN 106977559 A CN106977559 A CN 106977559A CN 201710184111 A CN201710184111 A CN 201710184111A CN 106977559 A CN106977559 A CN 106977559A
- Authority
- CN
- China
- Prior art keywords
- granatum
- concentration
- punicalagins
- purifying
- separating
- 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
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 229920001190 pomegranate ellagitannin Polymers 0.000 title claims abstract description 57
- LMIBIMUSUFYFJN-RSVYENFWSA-N punicalagin Natural products O[C@@H]1O[C@@H]2COC(=O)c3cc(O)c(O)c(O)c3c4c(O)cc5OC(=O)c6c(c(O)c(O)c7OC(=O)c4c5c67)c8c(O)c(O)c(O)cc8C(=O)O[C@H]2[C@@H]9OC(=O)c%10cc(O)c(O)c(O)c%10c%11c(O)c(O)c(O)cc%11C(=O)O[C@@H]19 LMIBIMUSUFYFJN-RSVYENFWSA-N 0.000 title claims abstract description 57
- 235000004515 gallic acid Nutrition 0.000 title claims abstract description 46
- 229940074391 gallic acid Drugs 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 37
- 239000011347 resin Substances 0.000 claims abstract description 54
- 229920005989 resin Polymers 0.000 claims abstract description 54
- 238000000605 extraction Methods 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000002425 crystallisation Methods 0.000 claims abstract description 30
- 239000002994 raw material Substances 0.000 claims abstract description 30
- 230000008025 crystallization Effects 0.000 claims abstract description 25
- 238000001179 sorption measurement Methods 0.000 claims abstract description 13
- 238000002203 pretreatment Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 239000000047 product Substances 0.000 claims description 45
- 238000001914 filtration Methods 0.000 claims description 27
- 238000001953 recrystallisation Methods 0.000 claims description 25
- 239000000284 extract Substances 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000012141 concentrate Substances 0.000 claims description 18
- 239000008367 deionised water Substances 0.000 claims description 15
- 235000014360 Punica granatum Nutrition 0.000 claims description 14
- 229910021641 deionized water Inorganic materials 0.000 claims description 14
- 239000000706 filtrate Substances 0.000 claims description 14
- 241000219991 Lythraceae Species 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 8
- 238000000108 ultra-filtration Methods 0.000 claims description 7
- 238000004042 decolorization Methods 0.000 claims description 6
- 238000007654 immersion Methods 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 238000004061 bleaching Methods 0.000 claims description 3
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- 238000002604 ultrasonography Methods 0.000 claims description 3
- 229930182470 glycoside Natural products 0.000 claims description 2
- 150000002338 glycosides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 16
- 239000011149 active material Substances 0.000 description 12
- 238000004140 cleaning Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000001514 detection method Methods 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- 229920002101 Chitin Polymers 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 229920002079 Ellagic acid Polymers 0.000 description 4
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 description 4
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000004132 ellagic acid Nutrition 0.000 description 4
- 229960002852 ellagic acid Drugs 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000004584 polyacrylic acid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 1
- 102000012286 Chitinases Human genes 0.000 description 1
- 108010022172 Chitinases Proteins 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- 206010027514 Metrorrhagia Diseases 0.000 description 1
- 241001415846 Procellariidae Species 0.000 description 1
- 208000012287 Prolapse Diseases 0.000 description 1
- 241001083505 Punica Species 0.000 description 1
- 244000294611 Punica granatum Species 0.000 description 1
- 102000003425 Tyrosinase Human genes 0.000 description 1
- 108060008724 Tyrosinase Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 210000000436 anus Anatomy 0.000 description 1
- 238000009412 basement excavation Methods 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229940094952 green tea extract Drugs 0.000 description 1
- 235000020688 green tea extract Nutrition 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 238000010262 high-speed countercurrent chromatography Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of method of separating-purifying punicalagins and gallic acid, including step simultaneously from granatum：Raw material pre-treatment, is extracted, concentration, and water is heavy to decolourize, resin adsorption, resin parsing, and desorbed solution extraction, crystallization.The above method, realize from granatum while separating-purifying punicalagins and gallic acid, and the content of separating-purifying punicalagins is more than the content of 98%, gallic acid more than 96%, the rate of recovery of punicalagins is more than the rate of recovery of 71%, gallic acid more than 68%.
Description
Technical field
The present invention relates to granatum extractive technique, more particularly to separation punicalagins are extracted simultaneously from granatum and are not eaten
The method of sub- acid.
Background technology
Pomegranate (Punica granatum L.) is Punicaceae Punica machaka or dungarunga plant, alias peace stone
If being a kind of medical and edible dual purpose plant if pomegranate, egg, pomegranate etc., the Central Asia such as Iran and Afghanistan are originated in, are had nearly 2000 in China
Cultivation history.Compendium of Materia Medica, which records pomegranate, has effects that " under antidiarrheal dysentery, lower blood, prolapse of the anus, metrorrhagia band ", and granatum contains
Abundant active component such as gallic acid, punicalagins etc..Punicalagins, molecular formula C48H28O30, molecular weight is 1084.72, peace
Pomegranate glycosides has a variety of pharmacological effects such as anti-oxidant, anticancer, antibacterial, antiviral, anti-inflammatory, in addition, punicalagins are inhaled by human body
After receipts, in the presence of human chitinase, ellagic acid can be decomposed into, ellagic acid oxidation resistant has been used as food oxydating resistance
Agent, and available in terms of cosmetics.Gallic acid molecular formula is C7H6O5, molecular weight 170.12, gallic acid has anti-inflammatory, anti-
The various biologicals such as mutation, anti-oxidant, Green Tea Extract activity, while gallic acid has antitumor, protection liver, suppresses endothelium
Loose effect.
Pomegranate is as the Chinese medicine of traditional integration of drinking and medicinal herbs, and its medicinal and edibility excavation is increasingly subject to pay attention to.And
Granatum processed as fruit pomegranate after accessory substance, be as Fertilizer application, if can effective profit in most cases at present
With the active material in granatum, then its value-added content of product has great raising.
At present, the patent and document of existing related separating-purifying punicalagins or gallic acid from granatum, for example specially
Sharp " a kind of pomegranate rind extracts of ZL200710106039.1 and preparation method thereof ", the disclosure of the invention using granatum as raw material,
Extracted through low-carbon alcohols organic solvent, the process such as concentration, column chromatography, drying obtains the granatum that punicalagins content is more than 40%
Extract.Patent " a kind of extracting methods of the punicalagins from granatum of ZL201010510836.8 ", the disclosure of the invention with
Granatum is raw material, is extracted with ethanol, and punicalagins product is obtained by UF membrane means, Activated Carbon Adsorption Separation；Patent
" a kind of methods that punicalagins and ellagic acid are prepared from granatum of ZL201010531940.5 ", the disclosure of the invention is with pomegranate
Skin is raw material, by processes such as extraction, filtering, acidification hydrolizations, obtains punicalagins purity more than 40%, ellagic acid purity exists
More than 90% product；" purifying process of punicalagins and its tyrosinase activity suppress to grind master's research paper in granatum
Study carefully, author：Cui Yanna " is thick from 40% punicalagins using dry post method, high-speed countercurrent chromatography, the combination of gel LH-20 chromatographies
The punicalagins product that purity is 96.21% is prepared in product.Consult, be showed no from granatum through patent retrieval and domestic and international paper
The method and report of punicalagins and gallic acid are extracted in raw material simultaneously, therefore to utilize the raw material of granatum to greatest extent
Value, it is necessary develop it is a kind of and meanwhile from granatum separating-purifying punicalagins and gallic acid technique.
The content of the invention
In view of above-mentioned condition, it is necessary to provide a kind of simultaneously separating-purifying punicalagins and gallic acid from granatum
Method, to realize separating-purifying punicalagins and gallic acid simultaneously.
The present invention provides a kind of method of separating-purifying punicalagins and gallic acid, including step simultaneously from granatum
Suddenly：Raw material pre-treatment：Granatum raw material is taken to be crushed；Extract：It is full below 4 using carbon atom under the conditions of certain temperature
Ultrasonic refluxing extraction is carried out to the granatum of crushing with alcohol, to obtain granatum extract solution；Concentration：Granatum extract solution is dense
Contracting, obtains granatum concentrate, while reclaiming organic solvent；Water is heavy to decolourize：Appropriate water, wadding will be added in granatum concentrate
Solidifying agent and decolorising agent enter water-filling and sink, decolourize, and water is heavy, filtering acquisition filtrate after a period of time of decolourizing；Resin adsorption：Filtrate passes through
Resin is adsorbed；Resin is parsed：Resin is washed with deionized, then successively uses low concentration Organic Alcohol and the organic alcoholysis of high concentration
Resin is analysed, low concentration Organic Alcohol desorbed solution A and high concentration Organic Alcohol desorbed solution B is collected respectively；Desorbed solution extraction, crystallization：Concentration
Desorbed solution A, the desorbed solution A of concentration is extracted with appropriate ethyl acetate, is collected lower floor's extract and is concentrated, ties at a certain temperature
Brilliant, dissolving, recrystallization, dry recrystallization and obtain separating-purifying product a；Meanwhile, desorbed solution B is concentrated, is extracted with appropriate chloroform
The desorbed solution B of concentration, collects lower floor's extract and concentrates, and lower crystallization, dissolving, recrystallization, dry recrystallization at a certain temperature
Obtain separating-purifying product b；Wherein, product a is the punicalagins that content is more than 98%, and product b is content not having more than 96%
Gallate-based.
Further, the extraction step, saturated alcohols of the carbon atom below 4 are ethanol or methanol, ethanol or methanol concentration
Between 50%~80% (V/V), needed before ultrasonic refluxing extraction carry out immersion 0.5 hour~2 hours, Extracting temperature be 60 DEG C~
80 DEG C, ultrasonic reflux extracting time is 1 hour~2 hours, and ultrasonic power is 3KW~30KW.
Further, the concentration step, the granatum extract solution is using being concentrated in vacuo, and the vacuum concentration is obtained
Granatum concentrate relative density be 1.1g/cm3~1.3g/cm3。
Further, the heavy decolorization process of the water, the water of addition is deionized water, and the volume for adding water is that granatum is concentrated
Liquid product 10 times~15 times, add flocculant weight for use granatum raw material weight 0.2%~0.5%, addition
The weight of decolorising agent by use granatum raw material weight 2%~5%, water is heavy, bleaching time is 8~12 hours.
Further, the filtering in the heavy decolorization process of the water includes press filtration and ultrafiltration, is first carried out using flame filter press
Press filtration and flocculant and decolorising agent are filtered out, then surpassed again more than or equal to 30000Dal milipore filters using molecular cut off
Filter is handled, and obtains filtrate.
Further, the milipore filter is vacuum tunica fibrosa.
Further, the resin adsorption step, the resin is polar macroporous adsorption resin, the polar macroporous absorption
Resin is LAS-7 polar resins or HPD500 polar resins.
Further, the resin analyzing step, the Organic Alcohol be ethanol or methanol, the Organic Alcohol of low concentration
Concentration is 15%~30% (V/V), and the concentration of the Organic Alcohol of high concentration is 50%~70% (V/V).
Further, the desorbed solution extraction, crystallisation step, the desorbed solution A of ethyl acetate extraction concentration and chloroform extraction
The desorbed solution B of concentration extraction times are respectively 2~3 times.
Further, the desorbed solution extraction, crystallisation step, primary crystallization, the control condition of recrystallization are 4 DEG C~8
12 hours~18 hours are stood still for crystals at DEG C.
The beneficial effect that the technical scheme of the embodiment of the present invention is brought is：The above method, is realized from granatum simultaneously
Separating-purifying punicalagins and gallic acid, and the content of separating-purifying punicalagins is big more than the content of 98%, gallic acid
In 96%, the rate of recovery of punicalagins is more than the rate of recovery of 71%, gallic acid more than 68%.
Brief description of the drawings
Fig. 1 is the flow chart of the method for separating-purifying punicalagins and gallic acid simultaneously from granatum of the present invention.
Embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with accompanying drawing to the embodiment of the present invention
It is described in further detail.
Fig. 1 is the flow chart of the method for separating-purifying punicalagins and gallic acid simultaneously from granatum of the present invention,
Specifically, refer to Fig. 1, the method for separating-purifying punicalagins and gallic acid of the invention simultaneously from granatum, including
Following steps：
S201：Raw material pre-treatment：Granatum raw material is taken to be crushed.
S202：Extract：Under the conditions of certain temperature, using saturated alcohols (C of the carbon atom below 4nH2n+1OH, n ＜ 4) to powder
Broken granatum carries out ultrasonic refluxing extraction, to obtain granatum extract solution.
S203：Concentration：Granatum extract solution is concentrated, granatum concentrate is obtained, while reclaiming organic solvent.
S204：Water is heavy to decolourize：Appropriate water, flocculant and decolorising agent will be added in granatum concentrate, and to enter water-filling heavy, de-
Color, water is heavy, filtering acquisition filtrate after a period of time of decolourizing.
S205：Resin adsorption：Filtrate is adsorbed by resin.
S206：Resin is parsed：Resin is washed with deionized, then successively uses low concentration Organic Alcohol and the organic alcoholysis of high concentration
Resin is analysed, low concentration Organic Alcohol desorbed solution A and high concentration Organic Alcohol desorbed solution B is collected respectively.
S207：Desorbed solution extraction, crystallization：Desorbed solution A is concentrated, the desorbed solution A of concentration is extracted with appropriate ethyl acetate, is received
Collection lower floor's extract is simultaneously concentrated, and is crystallized, dissolves, is recrystallized at a certain temperature, is dried recrystallization and is obtained separating-purifying product a；
Meanwhile, desorbed solution B is concentrated, the desorbed solution B of concentration is extracted with appropriate chloroform, lower floor's extract is collected and concentrates, in a constant temperature
The lower crystallization of degree, dissolving, recrystallization, dry recrystallization and obtain separating-purifying product b.
S208：Product detection and assay：With HPLC (high performance liquid chromatography, High Performance Liquid
Chromatography product a and product b composition and content) are detected, and calculates time of active material in product a and product b
Yield.
In S201 raw material pre-treatment steps, granatum raw material uses drying granatum, is crushed by pulverizer,
In order to which subsequent extracted is more efficient.Granatum raw material is come from Mengzi Yunnan, granatum raw material, and granatum feed moisture content is less than
10%th, the content of punicalagins is higher than 1.0% higher than the content of 5.0%, gallic acid.
In S202 extraction steps, saturated alcohols preferred alcohol or methanol of the carbon atom below 4, ethanol or methanol concentration exist
Between 50%~80% (V/V), needed before ultrasonic refluxing extraction after carrying out immersion 0.5 hour~2 hours, ultrasonic refluxing extraction temperature
For 60 DEG C~80 DEG C, ultrasonic reflux extracting time is 1 hour~2 hours, and ultrasonic use power is 3KW~30KW.
In S203 concentration steps, the concentration of granatum extract solution is using being concentrated in vacuo, while the saturation by carbon atom below 4
The organic solvents such as alcohol are reclaimed.It is 1.1g/cm to be concentrated in vacuo obtained concentrate relative density3~1.3g/cm3。
In S204 water sinks decolorization process, the water of addition is deionized water, and the volume for adding water is granatum concentrated liquid
Long-pending 10 times~15 times.Add flocculant weight for during extraction step use granatum raw material weight 0.2%~
0.5%, flocculant can be for chitin, polyacrylic acid, polyacrylate, polyacrylamide etc., but not limited to this.Add and decolourize
The weight of agent is by, using the 2%~5% of granatum raw material weight, decolorising agent refers generally to physical decolorization agent as lived during extraction step
Property charcoal.Water is heavy, bleaching time is 8~12 hours.Filtering includes press filtration and ultrafiltration, typically first carries out press filtration using flame filter press
And filter out flocculant and decolorising agent, hyperfiltration treatment is then carried out using the milipore filter of certain molecular cut off again, filtrate is obtained.
Ultrafiltration retaining molecular weight is more than or equal to 30000Dal, the preferred vacuum tunica fibrosa of milipore filter.
In S205 resin adsorption steps, the resin used is polar macroporous adsorption resin, preferred LAS-7 polar resins
Or HPD500 polar resins.
In S206 resin analyzing steps, resin is washed with a certain amount of deionized water, a certain amount of low concentration is then used
Organic Alcohol parses resin, collects its corresponding desorbed solution A1, resin is washed with a certain amount of deionized water again afterwards, is collected simultaneously
The cleaning solution A of this portions of de-ionized water2, merge desorbed solution A1With cleaning solution A2It is used as desorbed solution A；Finally with a certain amount of highly concentrated
Spend Organic Alcohol to continue to parse resin, while collecting desorbed solution B.Wherein, the Organic Alcohol preferred alcohol of resin is parsed, secondly methanol.
The concentration of low concentration Organic Alcohol is 15%~30% (V/V)；The concentration of high concentration Organic Alcohol is 50%~70% (V/V).Parsing
Liquid A is desorbed solution containing punicalagins, and desorbed solution B is desorbed solution containing gallic acid, can pass through S208 product detections and assay
Step is determined.
In the extraction of S207 desorbed solutions, crystallisation step, the desorbed solution A and chloroform of ethyl acetate extraction concentration extract concentration
Desorbed solution B extraction times are 2-3 times.Primary crystallization, dissolving, recrystallization, refer to quiet at 4 DEG C~8 DEG C at a certain temperature
Crystallization 12 hours~18 hours is put, low concentration (15%~30%) Organic Alcohol of the primary crystallization corresponding to desorbed solution A dissolves, and
Primary crystallization corresponding to desorbed solution B high concentration (50%~70%) Organic Alcohol dissolves, then stands and tie again at 4 DEG C~8 DEG C
It is brilliant 12 hours~18 hours.Recrystallization is dried using vacuum drying.
In S208 product detections and assay step, product a and product b composition and content is detected with HPLC.Production
Thing a is the punicalagins that content is more than 98%, and the rate of recovery of its active material is more than 71%；Product b is that content is more than 96%
Gallic acid, the rate of recovery of its active material is more than 68%.HPLC detection methods refer to document paper " China Dispensary 2013
The 3rd phase of volume 24, RP-HPLC methods determine the content of 4 kinds of polyphenol components in granatum, author Liu Zhenping, Chen Xianggui, Peng simultaneously
Petrel etc. ".
The calculation formula of the rate of recovery is as follows：
The weight/mass percentage composition of active material/(work in the quality * raw materials of raw material in the quality * products of the rate of recovery=product
The weight/mass percentage composition of property material) * 100%
Wherein, active material is punicalagins or gallic acid.
Embodiment one：
(content that granatum feed moisture content is less than 10%, punicalagins is 5.2%, not had Mengzi Yunnan granatum raw material
The content of gallate-based is 1.1%) to be crushed by pulverizer；100 kilograms of the granatum raw material crushed is taken to move into 1 cubic metre
Ultrasonic wave extraction equipment in, add 50% (V/V) concentration methanol 500L, immersion 1 hour after, be heated to 60 DEG C, and use
3KW ultrasonic powers ultrasound refluxing extraction 2 hours, releases granatum extract solution；Concentrated pomegranate skin extract solution, is obtained under vacuum
It is 1.1g/cm to obtain relative density3, volume be 120L granatum concentrate, while reclaim methanol；Then in granatum concentrate
In, add 1200L deionized water, 0.5 kilogram of chitin flocculant, 5 kilograms of 303 activated carbons of sugar, standing after stirring 5 minutes
8 hours, the heavy destainer of water removes chitin with flame filter press press filtration and sugar uses 303 activated carbons, is then cut again with 30000Dal
Stay the vacuum fiber ultrafiltration membrane of molecular weight to carry out hyperfiltration treatment, and obtain filtrate；Filtrate passes through polar macroporous adsorption resin
HPD500 (abbreviation resin) is adsorbed；Resin first is washed with 500L deionized water, is then 15% (V/V) with 300L concentration
The methanol of concentration is parsed, and collects its corresponding desorbed solution A1, resin then is washed with 200L deionized waters again, is collected simultaneously
The deionized water cleaning solution A of this part2, merge desorbed solution A1With cleaning solution A2It is used as desorbed solution A；It is with 400L concentration finally
The methanol parsing resin of 50% (V/V) concentration, while collecting desorbed solution B；Desorbed solution A is concentrated in vacuo, the desorbed solution A of concentration is added
Ethyl acetate is extracted twice, and lower floor's liquid after extraction is concentrated in vacuo again, and 12 hours are stood still for crystals at 4 DEG C, filtering
Primary crystallization thing is obtained, it is small that the primary crystallization thing stands recrystallization 12 after being dissolved with the methanol of 15% (V/V) concentration at 4 DEG C
When, filtering obtains recrystallization thing, and 3.75 kg product a are obtained after vacuum drying；It is concentrated in vacuo desorbed solution B, the desorbed solution B of concentration
Add chloroform to be extracted twice, lower floor's liquid after extraction is concentrated in vacuo again, and 12 hours are stood still for crystals at 4 DEG C, filtering
Primary crystallization thing is obtained, it is small that the primary crystallization thing stands recrystallization 12 after being dissolved with the methanol of 50% (V/V) concentration at 4 DEG C
When, filtering obtains recrystallization thing, and 0.78 kg product b is obtained after vacuum drying；It is content 98.6% with HPLC detections product a
Punicalagins, product b is that the rate of recovery of active material punicalagins in the gallic acid of content 96.7%, product a is 71.1%,
The rate of recovery of active material gallic acid is 68.6% in product b.
Embodiment two：
(content that granatum feed moisture content is less than 10%, punicalagins is 5.2%, not had Mengzi Yunnan granatum raw material
The content of gallate-based is 1.1%) to be crushed by pulverizer；100 kilograms of the granatum raw material crushed is taken to move into 1 cubic metre
Ultrasonic wave extraction equipment in, add 80% (V/V) concentration ethanol 600L, immersion 2 hours after, be heated to 70 DEG C, and use
10KW ultrasonic powers ultrasound refluxing extraction 1.5 hours, releases granatum extract solution；Concentrated pomegranate skin is extracted under vacuum
Liquid, acquisition relative density is 1.2g/cm3, volume be 115L granatum concentrate, while reclaim ethanol；Then in granatum
In concentrate, 1500L deionized water, 0.3 kilogram of chitin flocculant, 3 kilograms of 303 activated carbons of sugar, stirring 5 minutes are added
10 hours are stood afterwards, the heavy destainer of water removes chitin with flame filter press press filtration and sugar uses 303 activated carbons, then uses again
The vacuum fiber ultrafiltration membrane of 40000Dal molecular cut offs carries out hyperfiltration treatment, and obtains filtrate；Filtrate is inhaled by polar macroporous
Attached resin HPD500 (abbreviation resin) is adsorbed；Resin first is washed with 500L deionized water, is then with 300L concentration
The ethanol of 25% (V/V) concentration is parsed, and collects its corresponding desorbed solution A1, then wash tree with 200L deionized waters again
Fat, while collecting the deionized water cleaning solution A of this part2, merge desorbed solution A1With cleaning solution A2It is used as desorbed solution A；Finally use
400L concentration parses resin for the ethanol of 60% (V/V) concentration, while collecting desorbed solution B；Desorbed solution A is concentrated in vacuo, concentration
Desorbed solution A adds ethyl acetate and carries out extraction three times, and lower floor's liquid after extraction is concentrated in vacuo again, is stood still for crystals at 6 DEG C
15 hours, filtering obtained primary crystallization thing, and the primary crystallization thing is stood after being dissolved with the ethanol of 25% (V/V) concentration at 6 DEG C
Recrystallization 15 hours, filtering obtains recrystallization thing, and 4.03 kg product a are obtained after vacuum drying；Desorbed solution B is concentrated in vacuo, it is dense
The desorbed solution B of contracting adds chloroform and carries out extraction three times, and lower floor's liquid after extraction is concentrated in vacuo again, is stood still for crystals at 6 DEG C
15 hours, filtering obtained primary crystallization thing, and the primary crystallization thing is stood after being dissolved with the ethanol of 60% (V/V) concentration at 6 DEG C
Recrystallization 15 hours, filtering obtains recrystallization thing, and 0.86 kg product b is obtained after vacuum drying；With HPLC detections product a be containing
The punicalagins of amount 98.2%, product b is the recovery of active material punicalagins in the gallic acid of content 96.1%, product a
Rate is 76.1%, and the rate of recovery of active material gallic acid is 75.1% in product b.
Embodiment three：
(content that granatum feed moisture content is less than 10%, punicalagins is 5.2%, not had Mengzi Yunnan granatum raw material
The content of gallate-based is 1.1%) to be crushed by pulverizer；200 kilograms of the granatum raw material crushed is taken to move into 2 cubic metres
Ultrasonic wave extraction equipment in, add 65% (V/V) concentration ethanol 1400L, immersion 0.5 hour after, be heated to 80 DEG C, and adopt
With the ultrasonic refluxing extraction of 30KW ultrasonic powers 1 hour, granatum extract solution is released；Concentrated pomegranate skin is extracted under vacuum
Liquid, acquisition relative density is 1.3g/cm3, volume be 212L granatum concentrate, while reclaim ethanol；Then in granatum
In concentrate, 3000L deionized water, 0.4 kilogram of polyacrylic acid flocculant, 4 kilograms of 303 activated carbons of sugar, 5 points of stirring are added
12 hours are stood after clock, the heavy destainer of water removes polyacrylic acid with flame filter press press filtration and sugar uses 303 activated carbons, then uses again
The vacuum fiber ultrafiltration membrane of 40000Dal molecular cut offs carries out hyperfiltration treatment, and obtains filtrate；Filtrate is inhaled by polar macroporous
Attached resin LAS-7 (abbreviation resin) is adsorbed；Resin first is washed with 1000L deionized water, is then with 600L concentration
The ethanol of 30% (V/V) concentration is parsed, and collects its corresponding desorbed solution A1, then wash tree with 400L deionized waters again
Fat, while collecting the deionized water cleaning solution A of this part2, merge desorbed solution A1With cleaning solution A2It is used as desorbed solution A；Finally use
800L concentration parses resin for the ethanol of 70% (V/V) concentration, while collecting desorbed solution B；Desorbed solution A is concentrated in vacuo, concentration
Desorbed solution A adds ethyl acetate and is extracted twice, and lower floor's liquid after extraction is concentrated in vacuo again, is stood still for crystals at 8 DEG C
18 hours, filtering obtained primary crystallization thing, and the primary crystallization thing is stood after being dissolved with the ethanol of 30% (V/V) concentration at 8 DEG C
Recrystallization 18 hours, filtering obtains recrystallization thing, and 7.9 kg product a are obtained after vacuum drying；It is concentrated in vacuo desorbed solution B, concentration
Desorbed solution B add chloroform be extracted twice, lower floor's liquid after extraction is concentrated in vacuo again, and 18 are stood still for crystals at 8 DEG C
Hour, filtering obtains primary crystallization thing, and the primary crystallization thing stands weight after being dissolved with the ethanol of 70% (V/V) concentration at 8 DEG C
Crystallization 18 hours, filtering obtains recrystallization thing, and 1.64 kg product b are obtained after vacuum drying；It is content with HPLC detections product a
98.4% punicalagins, product b is the rate of recovery of active material punicalagins in the gallic acid of content 96.5%, product a
For 74.7%, the rate of recovery of active material gallic acid is 71.9% in product b.
The beneficial effect that the technical scheme of the embodiment of the present invention is brought is：The above method, is realized from granatum simultaneously
Separating-purifying punicalagins and gallic acid, and the content of separating-purifying punicalagins is big more than the content of 98%, gallic acid
In 96%, the rate of recovery of punicalagins is more than the rate of recovery of 71%, gallic acid more than 68%.
More than, only it is presently preferred embodiments of the present invention, any formal limitation not is made to the present invention, although this
Invention is disclosed above with preferred embodiment, but is not limited to the present invention, any those skilled in the art,
Do not depart from the range of technical solution of the present invention, when the technology contents using the disclosure above make a little change or are modified to equivalent
The equivalent embodiment of change, as long as being that, without departing from technical solution of the present invention content, the technical spirit according to the present invention is real to more than
Any simple modification, equivalent variations and modification that example made are applied, in the range of still falling within technical solution of the present invention.
Claims (10)
1. a kind of method of separating-purifying punicalagins and gallic acid simultaneously from granatum, it is characterised in that including step：
Raw material pre-treatment：Granatum raw material is taken to be crushed；
Extract：Under the conditions of certain temperature, ultrasound backflow is carried out to the granatum of crushing using saturated alcohols of the carbon atom below 4 and carried
Take, to obtain granatum extract solution；
Concentration：Granatum extract solution is concentrated, granatum concentrate is obtained, while reclaiming organic solvent；
Water is heavy to decolourize：Appropriate water, flocculant and decolorising agent will be added in granatum concentrate and enters that water-filling is heavy, decolourize, water is heavy,
Decolourize to filter acquisition filtrate after a period of time；
Resin adsorption：Filtrate is adsorbed by resin；
Resin is parsed：Resin is washed with deionized, then is successively divided with low concentration Organic Alcohol and high concentration Organic Alcohol parsing resin
Shou Ji not low concentration Organic Alcohol desorbed solution A and high concentration Organic Alcohol desorbed solution B；
Desorbed solution extraction, crystallization：Desorbed solution A is concentrated, the desorbed solution A of concentration is extracted with appropriate ethyl acetate, lower floor's extraction is collected
Take liquid and concentrate, crystallize, dissolve, recrystallize at a certain temperature, dry recrystallization and obtain separating-purifying product a；Meanwhile, concentration
Desorbed solution B, the desorbed solution B of concentration is extracted with appropriate chloroform, is collected lower floor's extract and is concentrated, lower at a certain temperature to tie
Brilliant, dissolving, recrystallization, dry recrystallization and obtain separating-purifying product b；Wherein, product a is the pomegranate that content is more than 98%
Glycosides, product b is the gallic acid that content is more than 96%.
2. as claimed in claim 1 while the method for separating-purifying punicalagins and gallic acid from granatum, it is characterised in that：
The extraction step, saturated alcohols of the carbon atom below 4 are ethanol or methanol, and ethanol or methanol concentration are in 50%~80% (V/V)
Between, need to carry out immersion 0.5 hour~2 hours before ultrasonic refluxing extraction, Extracting temperature is 60 DEG C~80 DEG C, ultrasonic refluxing extraction
Time is 1 hour~2 hours, and ultrasonic power is 3KW~30KW.
3. as claimed in claim 1 while the method for separating-purifying punicalagins and gallic acid from granatum, it is characterised in that：
The concentration step, the granatum extract solution is described to be concentrated in vacuo obtained granatum concentration liquid phase using being concentrated in vacuo
It is 1.1g/cm to density3~1.3g/cm3。
4. as claimed in claim 1 while the method for separating-purifying punicalagins and gallic acid from granatum, it is characterised in that：
The water sinks decolorization process, and the water of addition is deionized water, and the volume for adding water is 10 times~the 15 of the granatum volume of concentrate
Times, add flocculant weight for use granatum raw material weight 0.2%~0.5%, addition decolorising agent weight be institute
Using the 2%~5% of granatum raw material weight, water is heavy, bleaching time is 8~12 hours.
5. such as claim 1 or 4 from granatum the method for separating-purifying punicalagins and gallic acid simultaneously, its feature exists
In：Filtering in the heavy decolorization process of the water includes press filtration and ultrafiltration, first using flame filter press progress press filtration by flocculant
And decolorising agent is filtered out, 30000Dal milipore filters are then more than or equal to using molecular cut off again and carry out hyperfiltration treatment, are filtered
Liquid.
6. as claimed in claim 5 while the method for separating-purifying punicalagins and gallic acid from granatum, it is characterised in that：
The milipore filter is vacuum tunica fibrosa.
7. as claimed in claim 1 while the method for separating-purifying punicalagins and gallic acid from granatum, it is characterised in that：
The resin adsorption step, the resin is polar macroporous adsorption resin, and the polar macroporous adsorption resin is LAS-7 polarity trees
Fat or HPD500 polar resins.
8. as claimed in claim 1 while the method for separating-purifying punicalagins and gallic acid from granatum, it is characterised in that：
The resin analyzing step, the Organic Alcohol is ethanol or methanol, and the concentration of the Organic Alcohol of low concentration is 15%~30%
(V/V), the concentration of the Organic Alcohol of high concentration is 50%~70% (V/V).
9. as claimed in claim 1 while the method for separating-purifying punicalagins and gallic acid from granatum, it is characterised in that：
The desorbed solution extraction, crystallisation step, the desorbed solution A of ethyl acetate extraction concentration and the desorbed solution B of chloroform extraction concentration extraction
It is respectively 2~3 times to take number of times.
10. as claimed in claim 1 while the method for separating-purifying punicalagins and gallic acid, its feature exists from granatum
In：The desorbed solution extraction, crystallisation step, primary crystallization, the control condition of recrystallization are to stand still for crystals 12 at 4 DEG C~8 DEG C
Hour~18 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710184111.6A CN106977559A (en) | 2017-03-24 | 2017-03-24 | A kind of method of separating-purifying punicalagins and gallic acid simultaneously from granatum |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710184111.6A CN106977559A (en) | 2017-03-24 | 2017-03-24 | A kind of method of separating-purifying punicalagins and gallic acid simultaneously from granatum |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106977559A true CN106977559A (en) | 2017-07-25 |
Family
ID=59339593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710184111.6A Pending CN106977559A (en) | 2017-03-24 | 2017-03-24 | A kind of method of separating-purifying punicalagins and gallic acid simultaneously from granatum |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106977559A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108113803A (en) * | 2017-12-20 | 2018-06-05 | 江苏省健尔康医用敷料有限公司 | Medical plaster bandage |
| CN108250256A (en) * | 2018-03-05 | 2018-07-06 | 北京化工大学 | A kind of method for preparing high-purity punicalagins crystalline powder |
| CN108864217A (en) * | 2018-08-02 | 2018-11-23 | 新疆医科大学 | A kind of purification process of granatum punicalagins |
| CN110937993A (en) * | 2019-12-31 | 2020-03-31 | 上海仁酶生物科技有限公司 | Method for separating and refining gallic acid by using macroporous resin |
| CN113896751A (en) * | 2021-11-19 | 2022-01-07 | 成都农业科技中心 | Punicalagin purification method and application thereof in preparation of alpha-glucosidase inhibitor |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101955500A (en) * | 2010-10-19 | 2011-01-26 | 南京泽朗医药科技有限公司 | Method for extracting punicalagins from granatum |
| CN102180916A (en) * | 2010-11-23 | 2011-09-14 | 天津市尖峰天然产物研究开发有限公司 | Production process for extracting punicalagin from pomegranate rind with different maturity |
| CN102370591A (en) * | 2010-08-24 | 2012-03-14 | 上海博天尼化妆品有限公司 | Pomegranate rind extract method and application of pomegranate rind extract |
| CN103155953A (en) * | 2011-12-19 | 2013-06-19 | 陕西恒田化工有限公司 | Pomegranate peel polyphenol plant fungicide and application and preparation method |
| CN103505480A (en) * | 2012-06-21 | 2014-01-15 | 新疆医科大学 | Punica granatum peel antitumor polyphenol effective part, its preparation method and application |
| CN105878306A (en) * | 2016-04-11 | 2016-08-24 | 浙江中医药大学 | Preparation method of pomegranate peel polyphenols |
| CN106349301A (en) * | 2016-08-26 | 2017-01-25 | 陕西工业职业技术学院 | Method for separating and purifying punicalagin in pomegranate peel |
-
2017
- 2017-03-24 CN CN201710184111.6A patent/CN106977559A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102370591A (en) * | 2010-08-24 | 2012-03-14 | 上海博天尼化妆品有限公司 | Pomegranate rind extract method and application of pomegranate rind extract |
| CN101955500A (en) * | 2010-10-19 | 2011-01-26 | 南京泽朗医药科技有限公司 | Method for extracting punicalagins from granatum |
| CN102180916A (en) * | 2010-11-23 | 2011-09-14 | 天津市尖峰天然产物研究开发有限公司 | Production process for extracting punicalagin from pomegranate rind with different maturity |
| CN103155953A (en) * | 2011-12-19 | 2013-06-19 | 陕西恒田化工有限公司 | Pomegranate peel polyphenol plant fungicide and application and preparation method |
| CN103505480A (en) * | 2012-06-21 | 2014-01-15 | 新疆医科大学 | Punica granatum peel antitumor polyphenol effective part, its preparation method and application |
| CN105878306A (en) * | 2016-04-11 | 2016-08-24 | 浙江中医药大学 | Preparation method of pomegranate peel polyphenols |
| CN106349301A (en) * | 2016-08-26 | 2017-01-25 | 陕西工业职业技术学院 | Method for separating and purifying punicalagin in pomegranate peel |
Non-Patent Citations (9)
| Title |
|---|
| JINGJING LU ET AL.: "Preparative separation of punicalagin from pomegranate husk by high-speed countercurrent chromatography", 《JOURNAL OF CHROMATOGRAPHY B》 * |
| 冉懋雄等: "《现代中药栽培养殖与加工手册》", 31 May 1999, 中国中医药出版社 * |
| 刘姝 等: "优化石榴皮中安石榴苷的分离与纯化工艺", 《中国药师》 * |
| 朱静等: "大孔吸附树脂对石榴皮多酚的分离纯化", 《食品科技》 * |
| 李国秀: "石榴多酚类物质的分离鉴定和抗氧化活性研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
| 李端等: "《天然药物化学》", 30 September 2013, 中国医药科技出版社 * |
| 纪白慧: "石榴籽和石榴皮生物活性成分的研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
| 蒋克彬: "《污水处理工艺与应用》", 31 March 2014, 中国石化出版社出版发行 * |
| 顾翼东 主编: "《化学词典》", 30 September 1989, 上海辞书出版社 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108113803A (en) * | 2017-12-20 | 2018-06-05 | 江苏省健尔康医用敷料有限公司 | Medical plaster bandage |
| CN108113803B (en) * | 2017-12-20 | 2021-08-10 | 健尔康医疗科技股份有限公司 | Medical plaster bandage |
| CN108250256A (en) * | 2018-03-05 | 2018-07-06 | 北京化工大学 | A kind of method for preparing high-purity punicalagins crystalline powder |
| CN108250256B (en) * | 2018-03-05 | 2020-10-27 | 北京化工大学 | Method for preparing punicalagin crystal powder |
| CN108864217A (en) * | 2018-08-02 | 2018-11-23 | 新疆医科大学 | A kind of purification process of granatum punicalagins |
| CN110937993A (en) * | 2019-12-31 | 2020-03-31 | 上海仁酶生物科技有限公司 | Method for separating and refining gallic acid by using macroporous resin |
| CN113896751A (en) * | 2021-11-19 | 2022-01-07 | 成都农业科技中心 | Punicalagin purification method and application thereof in preparation of alpha-glucosidase inhibitor |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106977559A (en) | A kind of method of separating-purifying punicalagins and gallic acid simultaneously from granatum | |
| CN104940246B (en) | A method of extracting coprinus comatus element from coprinus comatus | |
| CN101560201B (en) | Technique for extracting puerarin and diverse medical ingredients from root of kudzuvine | |
| CN104710391B (en) | Method for extracting luteolin and beta-sitosterol from peanut shells | |
| CN102382083A (en) | Preparation method of andrographolide | |
| CN103772473A (en) | Vacuum pulse type method of extracting and purifying ursolic acid of rosemary | |
| CN102816066A (en) | Method for extracting chlorogenic acid and hyperoside from lonicera japonica leaves | |
| CN101172948B (en) | Method for separation and purification of cajanine and pinostrobin from extract of cajanus cajan branches and leaves | |
| CN105777698A (en) | Method for purifying pitaya peel anthocyanin | |
| CN103193832B (en) | Method for extracting and separating high-purity tea polyphenol from tea leaves | |
| CN106543245A (en) | A kind of method that arctiin is isolated and purified from burdock | |
| CN102078341B (en) | High-purity ginkgo flavone and composition thereof | |
| CN107216304A (en) | A kind of method of dihydroquercetin in ultrasound assisted extraction sorghum bran | |
| CN102031116A (en) | New method for preparing rosemary natural antioxidant | |
| CN102526150A (en) | Method for preparing total elecampane sesquiterpene lactone extract | |
| CN104000935B (en) | A kind of method that anti-oxidant phenolic acid is extracted in the slag from jacket | |
| CN105477026A (en) | Process for extracting ginkgolic acid, flavone, terpene lactones and polysaccharose from gingko exotesta in combined mode | |
| CN103239546A (en) | Method for extracting general flavone from litchi shells | |
| CN105732741A (en) | Method for extracting anthocyanin and ursolic acid from perilla leaves | |
| CN102327325A (en) | Method for preparing white mulberry rootbark general flavone | |
| CN101985440A (en) | Method for producing piperine | |
| CN111195268A (en) | Method for extracting polyphenols from pomegranate peel | |
| CN101683396A (en) | Extraction method of tropaeolum total lavonoids | |
| CN108046990A (en) | A kind of method of highly selective extraction Salanesol | |
| CN107722080A (en) | A kind of method that ursin is extracted in the leaf from purple bergenia herb |
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 |
Application publication date: 20170725 |
|
| RJ01 | Rejection of invention patent application after publication |