CN104886595A - Method for extracting flavonoids from peanut hulls with aqueous enzymatic method and alcohol and water solvent assisted by microwave - Google Patents
Method for extracting flavonoids from peanut hulls with aqueous enzymatic method and alcohol and water solvent assisted by microwave Download PDFInfo
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- 235000010777 Arachis hypogaea Nutrition 0.000 title claims abstract description 65
- 235000018262 Arachis monticola Nutrition 0.000 title claims abstract description 65
- 235000020232 peanut Nutrition 0.000 title claims abstract description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 30
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- 238000006911 enzymatic reaction Methods 0.000 title claims abstract description 11
- 241001553178 Arachis glabrata Species 0.000 title abstract description 57
- 229930003935 flavonoid Natural products 0.000 title abstract description 19
- 150000002215 flavonoids Chemical class 0.000 title abstract description 19
- 235000017173 flavonoids Nutrition 0.000 title abstract description 19
- 239000002904 solvent Substances 0.000 title abstract description 5
- 108090000790 Enzymes Proteins 0.000 claims abstract description 42
- 102000004190 Enzymes Human genes 0.000 claims abstract description 42
- 239000007788 liquid Substances 0.000 claims abstract description 28
- 238000005516 engineering process Methods 0.000 claims abstract description 18
- 238000003809 water extraction Methods 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 12
- 239000000843 powder Substances 0.000 claims abstract description 11
- 238000004108 freeze drying Methods 0.000 claims abstract description 10
- 238000004140 cleaning Methods 0.000 claims abstract description 9
- 238000003828 vacuum filtration Methods 0.000 claims abstract description 9
- 239000012528 membrane Substances 0.000 claims abstract description 5
- 229940088598 enzyme Drugs 0.000 claims description 41
- 229930003944 flavone Natural products 0.000 claims description 33
- 235000011949 flavones Nutrition 0.000 claims description 33
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims description 29
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims description 29
- 150000002212 flavone derivatives Chemical class 0.000 claims description 28
- 230000005855 radiation Effects 0.000 claims description 20
- 108090000371 Esterases Proteins 0.000 claims description 16
- 229920002678 cellulose Polymers 0.000 claims description 14
- 239000001913 cellulose Substances 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 12
- 235000012054 meals Nutrition 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 10
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- 229920002492 poly(sulfone) Polymers 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 4
- 108010059892 Cellulase Proteins 0.000 claims description 3
- 229940106157 cellulase Drugs 0.000 claims description 3
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- 244000105624 Arachis hypogaea Species 0.000 claims 8
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 15
- 230000003064 anti-oxidating effect Effects 0.000 abstract description 7
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- -1 flavone compound Chemical class 0.000 description 9
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- 241000196324 Embryophyta Species 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
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- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000000874 microwave-assisted extraction Methods 0.000 description 4
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- 239000000470 constituent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- 230000017531 blood circulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 150000004777 chromones Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
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- 229920005610 lignin Polymers 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
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- 239000002831 pharmacologic agent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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Classifications
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- 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)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
-
- 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
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- Biotechnology (AREA)
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- General Health & Medical Sciences (AREA)
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention discloses a method for extracting flavonoids from peanut hulls with an aqueous enzymatic method and alcohol and water solvent assisted by microwave. The method comprises the following steps: cleaning the peanut hulls, drying the cleaned hulls, smashing the dried hulls, adding water, adjusting pH value, adding compound enzyme and performing enzymolysis assisted by microwave; adding ethanol into the enzymolysis mixed liquid, and performing extraction assisted by microwave; subjecting the obtained product to vacuum filtration, separating the filtered product with a ultrafiltration membrane, and condensing separated product, and subjecting the condensed product to freeze drying to obtain peanut hull flavonoid powder with an anti-oxidation effect. The method disclosed in the invention is different from an alcohol-water extraction method in the prior art in that the enzymolysis method is firstly utilized to remove crosslinking or absorption between the flavonoids and cell walls, which facilitates the subsequent sufficient extraction of the flavonoids with the alcohol and water solvent assisted by microwave, and the peanut hull flavonoid powder with high anti-oxidation activity is obtained by separation with the ultrafiltration membrane and condensing as well as a freeze drying technology. The method disclosed in the invention has the advantages of simple process, shortened extraction time, improved extraction rate, energy saving, environment protection and suitability for industrial production, and the produced flavonoids have significant anti-oxidation effect.
Description
Technical field
The present invention relates to a kind of method that aqueous enzymatic method assisted microwave synthesis alcohol water extraction gets peanut shell flavone class material, belong to peanut processing byproduct active material extractive technique field.
Background technology
Plant is the mankind's the abundantest utilizable natural resources, and flavonoids bioactivator contained in plant is the main source of food, chemical industry and medical industry raw material.But these Flavonoid substances are with different glycoside forms in plant, be distributed in positions different in plant.Containing abundant flavone compound in peanut shell, based on cyanidenon.Modern study shows, peanut flavones is a kind of natural, there is stronger non-oxidizability and effect of scavenging radical, and as pharmacologic agents, at reduction cholesterol, improve blood circulation, reduce blood pressure and blood lipoid, control cardiovascular and cerebrovascular disease, strengthens immunity, and the aspect such as antibacterial, antiviral also has important effect, is therefore recorded as Chinese medicine in " Yunnan Province's drug standards ".
China is Peanut big producing country, a large amount of peanut shells has been discarded every year in peanut processing process, Flavonoid substances in abundant extraction peanut shell, as the raw material of health food or medicine trade, by contributing to the comprehensive utilization degree promoting peanut, reaches the object of recycling.
Flavonoid substances is the derivative of chromone or chromogen alkane, take C6-C3-C6 structure as the natural products of basic parent nucleus, and namely two phenyl ring are combined into by 3 carbon atoms, and in water, solubility is less.The method extracting flavones at present from plant mainly contains water seaoning, soda acid extraction, alcohol extracting method etc., utilizes microwave, ultrasonic assistant to extract and supercritical CO in recent years
2extraction to be carried etc. and can be improved recovery rate, but Flavonoid substances mostly is crosslinked or is adsorbed on cell membrane, traditional physical method not easily opens this structure, and be easily destroyed under condition extremely, and, due to the safety requirements to medical product and health products, multiplex alcohol water is as Extraction solvent, and extraction efficiency is often on the low side.In order to address these problems, need the peanut shell flavone extractive technique of establishing high-efficiency cleaning.
Enzymatic Extraction has become active component in medicinal plant and has extracted the important method of research.Due to the general flavone in peanut shell nearly all surround by the cell membrane based on cellulose, and, fiber and the content of lignin of peanut shell are high, the two combines with covalent, can also and cell wall polysaccharides component between combine in ester bond mode, therefore, apply after enzymolysis being carried out to peanut shell based on the compound enzyme liquid of cellulase and esterase, microwave radiation technology alcohol water is adopted to extract, be intended to recovery rate and the shortening extraction time of improving flavones in peanut shell, reduce extraction cost, set up the peanut shell flavone extractive technique of high-efficiency cleaning, for the further exploitation of flavones in peanut shell provide technical support.
Summary of the invention
The technical barrier such as the object of the invention is to get that low, the consuming time length of the efficiency existed in peanut shell flavone technology, cost are high for solving alcohol water extraction, active constituent content is low in extract, provides a kind of composite enzyme process assisted microwave synthesis alcohol water extraction to get the method with antioxidation peanut shell flavone.Cellulose-binding enzyme of the present invention and the composite zymolysis technique of esterase, utilize the method for microwave radiation exaraction solvent fully to be extracted by the Flavonoid substances in peanut shell, recovery rate improves, and extraction time shortens, in extract, active constituent content is high, and antioxidation is remarkable.
For achieving the above object, the technical solution adopted in the present invention is: enzymolysis peanut hull meal turbid solution, and microwave radiation technology alcohol water extraction gets the method for peanut shell flavone class material, and its step comprises:
One, peanut shell cleaning, oven dry, pulverizing;
Two, composite enzymolysis: peanut hull meal mixes by certain solid-liquid ratio with water, adjust ph, adds the compound enzyme of cellulase and esterase, and microwave radiation technology enzymolysis obtains enzymolysis mixed liquor;
Three, microwave radiation technology alcohol water extraction is got: by certain volume ratio, is joined by ethanol in above-mentioned enzymolysis liquid mixture, further microwave radiation exaraction Flavonoid substances;
Four, concentrate drying is separated: vacuum filtration alcohol aqueous extract, suction filtration liquid obtains peanut shell flavone concentrate through ultrafiltration concentration, and then freeze drying obtains the Flavonoids in Peanut Hull powder with antioxidation.
Preferably, the volume ratio of weight and water that a kind of aqueous enzymatic method assisted microwave synthesis alcohol water extraction gets the peanut hull meal of the pulverizing described in method step two of peanut shell flavone class material is 1:2(g/ml)-1:4(g/ml), pH value is adjusted to 7.0-10.0, adding enzyme lives as 12000U/mg alkali cellulose enzyme and enzyme work are the compound enzyme that 6000 U/mg esterases mix, alkali cellulose enzyme: esterase=3:2, the addition of compound enzyme is 2000-3000 U/ml mixed liquor, the condition of microwave radiation technology enzymolysis is temperature 30-40 DEG C, microwave power 400-600w, time 10-16min.
Preferably, the enzymolysis mixeding liquid volume described in method step three that a kind of aqueous enzymatic method assisted microwave synthesis alcohol water extraction gets peanut shell flavone class material is 4:1(ml/ml with ethanol contend ratio)-1:1(ml/ml), the condition of microwave radiation exaraction is temperature 80-100 DEG C, microwave power 300-1000w, time 5-15 min.
Preferably, the vacuum that a kind of aqueous enzymatic method assisted microwave synthesis alcohol water extraction gets the vacuum filtration described in method step four of peanut shell flavone class material is 0.1 MPa, the polysulfone hollow fibre milipore filter of Ultra filtration membrane concentrates condition to be molecular cut off be 5 kDa, with 0.2-0.3 MPa pressure, feeding liquid flow velocity 0.4 m/s, ultrafiltration concentration liquid obtains peanut shell flavone powder through freeze drying.
The invention has the beneficial effects as follows: according to the present invention, can provide that extraction efficiency is high, energy consumption is low, extraction time is short, cost is low, and antioxidation is remarkable, the peanut shell flavone powder that active constituent content is high.
Detailed description of the invention
Liquid chromatogram (HPLC) method is adopted to measure the content of cyanidenon in extract; Adopt the scavenging action of spectrophotometry hydroxyl radical free radical (OH) and DPPH free radical.
embodiment 1
Peanut shell, through cleaning, is dried, and pulverizes; Peanut hull meal is placed in Microwave Extraction container, weight in peanut hull meal: the volume=1:2(g/ml of water) ratio add water, adjust ph to 7.2, adding enzyme lives as 12000U/mg alkali cellulose enzyme and enzyme work are the compound enzyme (alkali cellulose enzyme: esterase=3:2) that 6000 U/mg esterases mix, addition is 2800 U/ml mixed liquors, at microwave power 500 w, under 35 DEG C of conditions, microwave radiation technology enzyme hydrolysis 12 min, obtains enzymolysis mixed liquor; In enzymolysis mixeding liquid volume: ethanol contend=2:1(ml/ml) ratio adds ethanol in enzymolysis mixed liquor, and at microwave power 600w, under 85 DEG C of conditions, microwave radiation technology alcohol water extraction gets 8min, obtains extract; Under vacuum 0.1 Mpa condition, vacuum filtration extract, obtains suction filtration liquid, employing molecular cut off is the polysulfone hollow fibre milipore filter of 5 kDa, with 0.3 MPa pressure, and feeding liquid flow velocity 0.4 m/s, retain permeate, ultrafiltration concentration liquid obtains peanut shell flavone powder through freeze drying.Extracting flavonoids rate under this embodiment condition is 4.67%; Concentration is the peanut shell general flavone of 10 mg/mL is 91.22% to the Scavenging activity of free radical OH, is 96.21% to the Scavenging activity of DPPH free radical.
embodiment 2
Peanut shell, through cleaning, is dried, and pulverizes; Peanut hull meal is placed in Microwave Extraction container, weight in peanut hull meal: the volume=1:4(g/ml of water) ratio add water, adjust ph to 8.5, adding enzyme lives as 12000U/mg alkali cellulose enzyme and enzyme work are the compound enzyme (alkali cellulose enzyme: esterase=3:2) that 6000 U/mg esterases mix, addition is 2500 U/ml mixed liquors, at microwave power 600 w, under 32 DEG C of conditions, microwave radiation technology enzyme hydrolysis 15 min, obtains enzymolysis mixed liquor; In enzymolysis mixeding liquid volume: ethanol contend=3:1(ml/ml) ratio adds ethanol in enzymolysis mixed liquor, and at microwave power 800 w, under 90 DEG C of conditions, microwave radiation technology alcohol water extraction gets 10 min, obtains extract; Under vacuum 0.1 Mpa condition, vacuum filtration extract, obtains suction filtration liquid, employing molecular cut off is the polysulfone hollow fibre milipore filter of 5 kDa, with 0.25 MPa pressure, and feeding liquid flow velocity 0.4 m/s, retain permeate, ultrafiltration concentration liquid obtains peanut shell flavone powder through freeze drying.Extracting flavonoids rate under this condition is 4.89%; Concentration is the peanut shell general flavone of 10 mg/mL is 90.91% to the Scavenging activity of free radical OH, is 94.33% to the Scavenging activity of DPPH free radical.
embodiment 3
Peanut shell, through cleaning, is dried, and pulverizes; Peanut hull meal is placed in Microwave Extraction container, weight in peanut hull meal: the volume=1:3(g/ml of water) ratio add water, adjust ph to 10.0, adding enzyme lives as 12000U/mg alkali cellulose enzyme and enzyme work are the compound enzyme (alkali cellulose enzyme: esterase=3:2) that 6000 U/mg esterases mix, addition is 3000 U/ml mixed liquors, at microwave power 400 w, under 40 DEG C of conditions, microwave radiation technology enzyme hydrolysis 16min, obtains enzymolysis mixed liquor; In enzymolysis mixeding liquid volume: ethanol contend=4:1(ml/ml) ratio adds ethanol in enzymolysis mixed liquor, and at microwave power 1000w, under 80 DEG C of conditions, microwave radiation technology alcohol water extraction gets 15min, obtains extract; Under vacuum 0.1Mpa condition, vacuum filtration extract, obtains suction filtration liquid, employing molecular cut off is the polysulfone hollow fibre milipore filter of 5 kDa, with 0.2MPa pressure, and feeding liquid flow velocity 0.4 m/s, retain permeate, ultrafiltration concentration liquid obtains peanut shell flavone powder through freeze drying.Extracting flavonoids rate under this embodiment condition is 5.36%; Concentration is the peanut shell general flavone of 10 mg/mL is 92.99% to the Scavenging activity of free radical OH, is 97.87% to the Scavenging activity of DPPH free radical.
embodiment 4
Peanut shell, through cleaning, is dried, and pulverizes; Peanut hull meal is placed in Microwave Extraction container, weight in peanut hull meal: the volume=1:4(g/ml of water) ratio add water, adjust ph to 9.0, adding enzyme lives as 12000U/mg alkali cellulose enzyme and enzyme work are the compound enzyme (alkali cellulose enzyme: esterase=3:2) that 6000 U/mg esterases mix, addition is 2000 U/ml mixed liquors, at microwave power 500 w, under 30 DEG C of conditions, microwave radiation technology enzyme hydrolysis 10 min, obtains enzymolysis mixed liquor; In enzymolysis mixeding liquid volume: ethanol contend=1:1(ml/ml) ratio adds ethanol in enzymolysis mixed liquor, and at microwave power 400w, under 100 DEG C of conditions, microwave radiation technology alcohol water extraction gets 5min, obtains extract; Under vacuum 0.1 Mpa condition, vacuum filtration extract, obtains suction filtration liquid, employing molecular cut off is the polysulfone hollow fibre milipore filter of 5 kDa, with 0.3 MPa pressure, and feeding liquid flow velocity 0.4 m/s, retain permeate, ultrafiltration concentration liquid obtains peanut shell flavone powder through freeze drying.Extracting flavonoids rate under this embodiment condition is 4.97%; Concentration is the peanut shell general flavone of 10 mg/mL is 90.17% to the Scavenging activity of free radical OH, is 95.32% to the Scavenging activity of DPPH free radical.
The above, be only the specific embodiment of the present invention, is not limited thereto, and is anyly familiar with those skilled in the art in the technical scope that the present invention discloses, and can expect change easily or replace, all should be encompassed within protection scope of the present invention.
Claims (4)
1. aqueous enzymatic method assisted microwave synthesis alcohol water extraction gets a method for peanut shell flavone class material, comprises the following steps:
(1) peanut shell cleaning, dries, and pulverizes, adds water, adjust ph, add the compound enzyme of cellulase and esterase, microwave radiation technology enzymolysis;
(2) ethanol is added, microwave radiation exaraction in enzymolysis mixed liquor;
(3) vacuum filtration, Ultra filtration membrane concentrated extracting solution, freeze drying, obtains the peanut shell flavone powder of Wheat Protein.
2. a kind of aqueous enzymatic method assisted microwave synthesis alcohol water extraction according to claim 1 gets the method for peanut shell flavone class material, it is characterized in that, the weight of the peanut hull meal of the pulverizing described in step (1) and the volume ratio of water are 1:2(g/ml)-1:4(g/ml), pH value is adjusted to 7.0-10.0, adding enzyme lives as 12000U/mg alkali cellulose enzyme and enzyme work are the compound enzyme that 6000 U/mg esterases mix, alkali cellulose enzyme: esterase=3:2, the addition of compound enzyme is 2000-3000 U/ml mixed liquor, the condition of microwave radiation technology enzymolysis is temperature 30-40 DEG C, microwave power 400-600w, time 10-16min.
3. a kind of aqueous enzymatic method assisted microwave synthesis alcohol water extraction according to claim 1 gets the method for peanut shell flavone class material, it is characterized in that, enzymolysis mixeding liquid volume described in step (2) and ethanol contend are than being 4:1(ml/ml)-1:1(ml/ml), the condition of microwave radiation exaraction is temperature 80-100 DEG C, microwave power 300-1000w, time 5-15 min.
4. a kind of aqueous enzymatic method assisted microwave synthesis alcohol water extraction according to claim 1 gets the method for peanut shell flavone class material, it is characterized in that, the vacuum of the vacuum filtration described in step (3) is 0.1 MPa, the polysulfone hollow fibre milipore filter of Ultra filtration membrane concentrates condition to be molecular cut off be 5 kDa, with 0.2-0.3 MPa pressure, feeding liquid flow velocity 0.4 m/s, ultrafiltration concentration liquid obtains peanut shell flavone powder through freeze drying.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106884026A (en) * | 2017-01-24 | 2017-06-23 | 山东省花生研究所 | A kind of active polysaccharide rich in flavone compound and preparation method thereof |
| CN107266931A (en) * | 2017-07-10 | 2017-10-20 | 桂林融通科技有限公司 | A kind of method for extracting peanut shell uranidin |
| CN108642914A (en) * | 2018-06-26 | 2018-10-12 | 乡宁县云丘山旅游开发有限责任公司 | A kind of preparation method of natural plants dyed cloth |
| CN108677559A (en) * | 2018-06-26 | 2018-10-19 | 乡宁县云丘山旅游开发有限责任公司 | A kind of natural plants cloth dyeing technology |
| CN111296838A (en) * | 2020-02-28 | 2020-06-19 | 西昌市正中食品有限公司 | Preparation process of tartary buckwheat nutritional extract rich in flavone |
| CN115368335A (en) * | 2022-09-06 | 2022-11-22 | 山东福洋生物制造工程研究院 | <xnotran></xnotran> |
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| CN108677559A (en) * | 2018-06-26 | 2018-10-19 | 乡宁县云丘山旅游开发有限责任公司 | A kind of natural plants cloth dyeing technology |
| CN111296838A (en) * | 2020-02-28 | 2020-06-19 | 西昌市正中食品有限公司 | Preparation process of tartary buckwheat nutritional extract rich in flavone |
| CN115368335A (en) * | 2022-09-06 | 2022-11-22 | 山东福洋生物制造工程研究院 | <xnotran></xnotran> |
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