CN103695479B - High-purity resveratrol preparation method - Google Patents
High-purity resveratrol preparation method Download PDFInfo
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- CN103695479B CN103695479B CN201310725682.8A CN201310725682A CN103695479B CN 103695479 B CN103695479 B CN 103695479B CN 201310725682 A CN201310725682 A CN 201310725682A CN 103695479 B CN103695479 B CN 103695479B
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- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 235000021283 resveratrol Nutrition 0.000 title claims abstract description 13
- 229940016667 resveratrol Drugs 0.000 title claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000000605 extraction Methods 0.000 claims abstract description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012043 crude product Substances 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- RHMXXJGYXNZAPX-UHFFFAOYSA-N emodin Chemical compound C1=C(O)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O RHMXXJGYXNZAPX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 11
- 239000000284 extract Substances 0.000 claims abstract description 9
- 108090000790 Enzymes Proteins 0.000 claims abstract description 8
- 102000004190 Enzymes Human genes 0.000 claims abstract description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 3
- 241001648835 Polygonum cuspidatum Species 0.000 claims abstract 2
- 235000018167 Reynoutria japonica Nutrition 0.000 claims abstract 2
- 229940079593 drug Drugs 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000470 constituent Substances 0.000 claims description 12
- 229940088598 enzyme Drugs 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 7
- 230000003014 reinforcing effect Effects 0.000 claims description 6
- 108010059892 Cellulase Proteins 0.000 claims description 5
- 108010059820 Polygalacturonase Proteins 0.000 claims description 5
- 229940106157 cellulase Drugs 0.000 claims description 5
- -1 concentrated Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000003808 methanol extraction Methods 0.000 claims description 5
- 238000010298 pulverizing process Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000002386 leaching Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 239000010282 Emodin Substances 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000019634 flavors Nutrition 0.000 abstract 1
- 238000004537 pulping Methods 0.000 abstract 1
- 235000018991 trans-resveratrol Nutrition 0.000 description 25
- 244000153955 Reynoutria sachalinensis Species 0.000 description 20
- 235000003202 Reynoutria sachalinensis Nutrition 0.000 description 20
- 238000005516 engineering process Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HSTZMXCBWJGKHG-UHFFFAOYSA-N (E)-piceid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(C=CC=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960003764 polydatin Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- HSTZMXCBWJGKHG-CUYWLFDKSA-N trans-piceid Polymers O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(\C=C\C=2C=CC(O)=CC=2)=C1 HSTZMXCBWJGKHG-CUYWLFDKSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 241000219050 Polygonaceae Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a high-purity resveratrol preparation method which comprises (1) pulping or crushing a bulk drug polygonum cuspidatum; (2) taking 30%-90% ethyl alcohol as a solvent to conduct pot group type dynamic countercurrent extraction, conducting vacuum concentration after extraction until no alcohol flavor exists, and keeping the mixture for later use; (3) adding a complex enzyme preparation to conduct enzymolysis, and concentrating and filtering after enzymolysis to obtain a crude product; (4) extracting the obtained crude product by using methyl alcohol, drying the extract to obtain a by-product rheum emodin, and enabling the extract liquor to be subjected to alumina column alumina column chromatography, methyl alcohol analysis, concentration, gasoline washing, activated carbon decoloration, ethyl alcohol crystallization and drying to obtain the high-purity resveratrol. According to the invention, extraction and then enzymolysis are conducted to convert the polygonin, so that the conversion time is shortened, the adoption of the dynamic countercurrent and the combination of vacuum pulse improve the extraction rate, the environment protecting production of the resveratrol with short period, less steps and low loss is implemented, and the application prospect is wide.
Description
Technical field
The present invention relates to a kind of preparation method of high-purity resveratrol, specifically refer to Isolation and purification trans-resveratrol from giant knotweed, and obtain the method for byproduct Schuttgelb.
Background technology
Giant knotweed is that polygonaceae belongs to perennial vine, is distributed widely in East China, the Central-South and ground such as Liaoning, Shaanxi, Gansu, Sichuan, Yunnan.Chinese scholars from having done large quantity research, finds that its rhizome contains a kind of Polyhydroxystibene to the chemical composition of giant knotweed---trans-resveratrol, i.e. 3,4,5-trihydroxy-toluylene, belong to tannin matter polyphenol.It has reducing blood-fat, antithrombotic, prevention of arterial sclerosis to human body, strengthens the important regulatives such as immunologic function, be widely used in the fields such as medicine intermediate, foodstuff additive, protective foods, through development and the research of decades, trans-resveratrol has defined stable domestic and international market
From giant knotweed, extract trans-resveratrol technique have more report, because the trans-resveratrol in giant knotweed exists mainly with the form of polydatin greatly, thus existing trans-resveratrol production technique is all generally first by fermentable, polydatin (also known as polygonin) is converted into trans-resveratrol to extract again, owing to also creating more glucide while microbial transformation trans-resveratrol, thus the viscosity of material strengthens, in leaching process, the penetrance of solvent is deteriorated, and causes extraction yield low long with extraction time; Having extracted the purifying after trans-resveratrol mostly to need to use trichloromethane, and is twice upper prop, need through Resveratrol content be 20% and 50% twice intermediates link, thus life cycle of the product is long, loss is large, and cost is high, also there is the risk of poisonous harmful organic solvent.
Therefore, the Development and Production cycle is short, step is few, loss is low, the high-purity resveratrol production technique of environmental protection, significant.
Summary of the invention
For solving the above-mentioned prior art Problems existing extracting trans-resveratrol from giant knotweed, the present inventor through a large amount of production practice, finally invent a kind of with short production cycle, step is few, loss is low, the high-purity resveratrol production technique of environmental protection.
The present invention includes following step:
(1) process of raw medicinal material: no matter giant knotweed raw medicinal material is dry wet, wet giant knotweed carries out making beating process, if dry giant knotweed then carries out pulverization process, this Technology, to the not requirement of the humidity of raw medicinal material, reduces medicinal material processing cost.
(2) extraction and concentration of effective constituent: with the ethanol of 30%-90% for solvent, solvent carries out the extraction of pot group type dynamic countercurrent, extraction time 6-10 hour, Extracting temperature 40-75 DEG C with the volume mass of raw medicinal material than for 7:1-15:1, be evaporated to after extraction completes without alcohol taste, for subsequent use.In volume mass ratio, the unit of volume is milliliter, and the unit of quality is gram.
In said extracted process, step vacuumizing and vacuum breaker is carried out to extractor, utilize vacuum impulse reinforcing mass transfer.The mechanism of vacuum impulse reinforcing mass transfer is: because ethanol is the organic solvent that volatility is stronger, ethanol when vacuumizing in giant knotweed cell tissue can gasify because of decompression, cause giant knotweed cell tissue internal pressure to be greater than outside giant knotweed histocyte, the ethanol having dissolved effective constituent can be forced through giant knotweed cell tissue under differential pressure action; When vacuum breaker, giant knotweed histocyte external pressure is greater than pressure in giant knotweed histocyte, ethanol outside giant knotweed histocyte enters rapidly giant knotweed histocyte inside and goes to dissolve effective constituent because of differential pressure action, the change that replaces of this giant knotweed histocyte external and internal pressure enhances ethanol and dissolving effective constituent mass transfer in ethanol, makes extraction efficiency raising, the reduction of effective constituent residual rate.
(3) enzymolysis: the compound enzymic preparation adding quality of medicinal material 8/2000 to thousand/1000ths carries out enzymolysis, enzymolysis makes polygonin be converted into trans-resveratrol, enzymolysis time 6-15 hour, hydrolysis temperature 35-55 DEG C, should constantly stir in enzymolysis process, concentrated after enzymolysis completes, filter after namely obtain crude product.The proportioning of compound enzymic preparation is cellulase massfraction 50-80%, polygalacturonase massfraction is 15-30%, all the other are zytase, the average enzyme of compound enzymic preparation is lived as 10000-50000 unit, international zymetology meeting regulation in 1961 is deferred to by described Mei Huo unit, refers under specified conditions (25 DEG C, other is optimum condition), the enzyme amount of 1 micromole substrate can be transformed in 1 minute, or the 1 micromolar enzyme amount about group in conversion of substrate.
(4) separation and purification: by the crude product methanol extraction obtained, extract remainder is drying to obtain byproduct Schuttgelb, in byproduct, Schuttgelb massfraction is 40%-60%, extraction liquid is resolved through alumina column chromatography, methyl alcohol, concentrated, gasoline washing, activated carbon decolorizing, alcohol crystal must fine work trans-resveratrol after drying, trans-resveratrol massfraction is 98%-99.8%.
Compared with prior art, the invention has the beneficial effects as follows: employing is first extracted and substituted traditional method extracted again of first fermenting by the method for compound enzymic preparation enzymolysis again, the time making polygonin be converted into trans-resveratrol shortened to 6-15 hour by 20-40 days, and in enzymolysis process, the transformation efficiency of polygonin is high; Adopt dynamic countercurrent and in conjunction with vacuum impulse, the effective constituent in giant knotweed extracted, effectively shortening extraction time, improve the extraction yield of effective constituent; Purifying process use extract, concentrated after crude product do raw material, do not have Resveratrol content be 20% and 50% intermediates link, directly obtain the fine work trans-resveratrol that content is more than 98%, compared with doing raw material production fine work trans-resveratrol with the trans-resveratrol of existing extensive employing 50%, trans-resveratrol yield improves more than 10%, enhances product competitive power commercially; This technique, to the not requirement of the humidity of giant knotweed raw material, reduces Feedstock treating cost; This technique also obtains the Schuttgelb that byproduct-massfraction is 40%-60% while obtaining fine work trans-resveratrol.
In sum, the present invention is by carrying out effective integration by above multinomial technology, and achieve the short period of Isolation and purification trans-resveratrol from giant knotweed, few step, low-loss and environmental protection and produce, the market competitiveness is strong, has a extensive future.
Embodiment
Below the preparation method of high-purity resveratrol is described in detail.
Embodiment 1:
(1) process of raw medicinal material: Rhizoma Polygoni Cuspidati is carried out pulling an oar or pulverization process.
(2) extraction and concentration of effective constituent: the ethanol with 35% is solvent, solvent carries out the extraction of pot group type dynamic countercurrent with the volume mass of raw medicinal material than for 8:1,6.5 hours extraction times, Extracting temperature 45 DEG C, be evaporated to after extraction completes without alcohol taste, for subsequent use, in said extracted process, step vacuumizing and vacuum breaker is carried out to extractor, utilize vacuum impulse reinforcing mass transfer.
(3) enzymolysis: the compound enzymic preparation adding quality of medicinal material 3/1000ths carries out enzymolysis, enzymolysis time 9 hours, hydrolysis temperature 45 DEG C, constantly stirs in enzymolysis process, concentrated after enzymolysis completes, filter after namely obtain crude product; The proportioning of compound enzymic preparation is cellulase massfraction 65%, and polygalacturonase massfraction is 21%, and all the other are zytase, and the average enzyme work of compound enzymic preparation is 14000 units, and international zymetology meeting regulation in 1961 is deferred to by described Mei Huo unit.
(4) separation and purification: by the crude product methanol extraction obtained, extract remainder is drying to obtain byproduct Schuttgelb, in byproduct, Schuttgelb massfraction is 49%, extraction liquid is resolved through alumina column chromatography, methyl alcohol, concentrated, gasoline washing, activated carbon decolorizing, alcohol crystal must fine work trans-resveratrol after drying, trans-resveratrol massfraction is 98.8%.
Embodiment 2:
(1) process of raw medicinal material: Rhizoma Polygoni Cuspidati is carried out pulling an oar or pulverization process.
(2) extraction and concentration of effective constituent: the ethanol with 82% is solvent, solvent carries out the extraction of pot group type dynamic countercurrent with the volume mass of raw medicinal material than for 11:1,9.5 hours extraction times, Extracting temperature 72 DEG C, be evaporated to after extraction completes without alcohol taste, for subsequent use, in said extracted process, step vacuumizing and vacuum breaker is carried out to extractor, utilize vacuum impulse reinforcing mass transfer.
(3) enzymolysis: the compound enzymic preparation adding quality of medicinal material 7/1000ths carries out enzymolysis, enzymolysis time 6.2 hours, hydrolysis temperature 53 DEG C, constantly stirs in enzymolysis process, concentrated after enzymolysis completes, filter after namely obtain crude product; The proportioning of compound enzymic preparation is cellulase massfraction 54%, and polygalacturonase massfraction is 28%, and all the other are zytase, and the average enzyme work of compound enzymic preparation is 43000 units, and international zymetology meeting regulation in 1961 is deferred to by described Mei Huo unit.
(4) separation and purification: by the crude product methanol extraction obtained, extract remainder is drying to obtain byproduct Schuttgelb, in byproduct, Schuttgelb massfraction is 57%, extraction liquid is resolved through alumina column chromatography, methyl alcohol, concentrated, gasoline washing, activated carbon decolorizing, alcohol crystal must fine work trans-resveratrol after drying, trans-resveratrol massfraction is 98.1%.
Embodiment 3:
(1) process of raw medicinal material: Rhizoma Polygoni Cuspidati is carried out pulling an oar or pulverization process.
(2) extraction and concentration of effective constituent: the ethanol with 70% is solvent, solvent carries out the extraction of pot group type dynamic countercurrent with the volume mass of raw medicinal material than for 14:1,7.9 hours extraction times, Extracting temperature 60 DEG C, be evaporated to after extraction completes without alcohol taste, for subsequent use, in said extracted process, step vacuumizing and vacuum breaker is carried out to extractor, utilize vacuum impulse reinforcing mass transfer.
(3) enzymolysis: the compound enzymic preparation adding quality of medicinal material 5/1000ths carries out enzymolysis, enzymolysis time 14 hours, hydrolysis temperature 38 DEG C, constantly stirs in enzymolysis process, concentrated after enzymolysis completes, filter after namely obtain crude product; The proportioning of compound enzymic preparation is cellulase massfraction 76%, and polygalacturonase massfraction is 16%, and all the other are zytase, and the average enzyme work of compound enzymic preparation is 32000 units, and international zymetology meeting regulation in 1961 is deferred to by described Mei Huo unit.
(4) separation and purification: by the crude product methanol extraction obtained, extract remainder is drying to obtain byproduct Schuttgelb, in byproduct, Schuttgelb massfraction is 41%, extraction liquid is resolved through alumina column chromatography, methyl alcohol, concentrated, gasoline washing, activated carbon decolorizing, alcohol crystal must fine work trans-resveratrol after drying, trans-resveratrol massfraction is 99.2%.
Claims (1)
1. a preparation method for high-purity resveratrol, is characterized in that comprising following step:
(1) process of raw medicinal material: bulk drug polygonum cuspidatum is carried out pulling an oar or pulverizing;
(2) extraction and concentration of effective constituent: with the ethanol of 30%-90% for solvent, solvent carries out the extraction of pot group type dynamic countercurrent with the volume mass of raw medicinal material than for 7:1-15:1, extraction time 6-10 hour, Extracting temperature 40-75 DEG C, be evaporated to after extraction completes without alcohol taste, for subsequent use, in described volume mass ratio, the unit of volume is milliliter, and the unit of quality is gram;
In the leaching process of effective constituent, step vacuumizing and vacuum breaker is carried out to extractor, utilize vacuum impulse reinforcing mass transfer;
(3) enzymolysis: the compound enzymic preparation adding quality of medicinal material 8/2000 to thousand/1000ths carries out enzymolysis, enzymolysis time 6-15 hour, and hydrolysis temperature 35-55 DEG C, constantly stirs in enzymolysis process, concentrated after enzymolysis completes, filter after namely obtain crude product;
The proportioning of described compound enzymic preparation is cellulase massfraction 50-80%, polygalacturonase massfraction is 15-30%, all the other are zytase, and the average enzyme of compound enzymic preparation is lived as 10000-50000 unit, and international zymetology meeting regulation in 1961 is deferred to by Mei Huo unit;
(4) separation and purification: by the crude product methanol extraction obtained, extract remainder dry byproduct Schuttgelb, extraction liquid is resolved through alumina column chromatography, methyl alcohol, concentrated, gasoline washing, activated carbon decolorizing, alcohol crystal must high-purity resveratrol after drying.
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| CN105250487A (en) * | 2015-10-19 | 2016-01-20 | 潘勤霞 | Method for extracting flavone from eggplants |
| CN107300590A (en) * | 2017-05-26 | 2017-10-27 | 广州中医药大学 | A kind of HPLC detection methods that polygonin and resveratrol are extracted from giant knotweed |
| CN108821953A (en) * | 2018-05-30 | 2018-11-16 | 上海华堇生物技术有限责任公司 | A kind of polishing purification method of natural resveratrol |
| CN111909005A (en) * | 2020-08-11 | 2020-11-10 | 唐山市食品药品综合检验检测中心(唐山市检验检测研究院) | Preparation method of peanut skin residue resveratrol |
| CN112552147A (en) * | 2020-11-24 | 2021-03-26 | 菏泽学院 | Preparation method for extracting resveratrol from paeonia ostii seed meal |
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| CN101338327B (en) * | 2008-08-13 | 2011-03-23 | 长沙华诚生物科技有限公司 | Process for extracting resveratrol with purity higher than 98 0.000000rom giant knotweed |
| CN101643754A (en) * | 2009-08-31 | 2010-02-10 | 三明华健生物工程有限公司 | New technique for extracting and preparing high-purity resveratrol from giant knotweed |
| CN102080108A (en) * | 2010-12-15 | 2011-06-01 | 云南弗蓝替生物工程有限公司 | Method for extracting emodin, polydatin and resveratrol from polygonum cuspidatum by using vacuum enzymolysis technology |
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