CN106755162A - A kind of method that enzyme process prepares fat-soluble grape pip procyanidin - Google Patents
A kind of method that enzyme process prepares fat-soluble grape pip procyanidin Download PDFInfo
- Publication number
- CN106755162A CN106755162A CN201611087009.6A CN201611087009A CN106755162A CN 106755162 A CN106755162 A CN 106755162A CN 201611087009 A CN201611087009 A CN 201611087009A CN 106755162 A CN106755162 A CN 106755162A
- Authority
- CN
- China
- Prior art keywords
- grape pip
- lipase
- fat
- pip procyanidin
- soluble
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
The invention discloses the technique that a kind of continuity method prepares aqueous polyurethane optical coating.The technique includes：1) diisocyanate is the invention discloses a kind of method that enzyme process prepares fat-soluble grape pip procyanidin.The method is first mixed grape pip procyanidin with the organic aliphatic acid containing 2~30 carbon atoms with certain proportion, adds solvent, and 0.1~10h is stirred at 20~90 DEG C.Add immobilized lipase as catalyst, heating stirring reacts 1~48h at 20~90 DEG C, lipase is separated, terminating reaction, decompression boils off its filtrate makes into sticky oil thing.Product of the invention obtained can be added in edible oil with arbitrary proportion, and antioxidant effect substantially and stable performance, and keeps the quality of original grease, preparation process is simple, safe and reliable.Fat-soluble grape pip procyanidin edible safety prepared by the present invention.
Description
Technical field
The present invention relates to fat-soluble grape pip procyanidin, more particularly to a kind of preparation method of natural, tool
Body is related to a kind of method that enzyme process prepares fat-soluble grape pip procyanidin.
Background technology
Grape pip procyanidin, abbreviation OPC is a kind of bioflavonoid for having a special molecular structure, is the current world
The upper generally acknowledged removing maximally effective natural of people's interior free yl.Grape pip procyanidin has very strong internal work
Property, with extremely strong effect that is anti-oxidant, eliminating free radical, ultra-oxygen anion free radical and hydroxyl radical free radical can be effectively eliminated,
Also there is eye health, heart rate health care, dangerous pathogenesis of cancer, enhancing blood vessel intensity, anti-inflammatory, the multiple efficacies such as swollen of dispelling are reduced.
Grape pip procyanidin is soluble in water, can also be dissolved in methyl alcohol, ethanol, acetone polar organic solvent.But it is more
Hydroxyl structure, causes its good hydrophilic property and lipophile is weak, is insoluble in oil, limits it in fat esters food and other oil-containings
Application in food.Therefore, developing fat-soluble grape pip procyanidin product has wide market prospects.
Though the method that conventional method prepares fat-soluble grape pip procyanidin is relatively easy, solvent residual amount is big, in order to
Make product without toxic component, cause subsequent treatment process complicated, but also bring emission pollution problem.Chinese invention patent
CN101066075 disclose addition grape pip procyanidin microemulsion edible fat production method, by oleic acid polyglycerol monoester with
Ethanol is with 4：1 ratio is uniformly mixed in the range of 20-40 DEG C, by volume for the amount of 1-5% is added dropwise over grape pip
The OPC aqueous solution, adds while stirring, until forming uniform and stable solution, is disperseed at a high speed with Ultra-TurraxT25
Machine disperses grape pip procyanidin emulsion 3-5 minutes under the conditions of 20,000rpm, static 1 hour, stand-by；Regulation is edible
Oil temperature is stirred 30 minutes with mixer in the range of 20-40 DEG C under the conditions of 1,000rpm, the former flower of the grape pip that will be prepared
Blue or green element emulsion is slowly added in edible oil according to the ratio of volume ratio 5-10%, stirring while adding, until fat clarification is without muddy
Untill turbid, the edible oil of grape pip procyanidin microemulsion is as added.
Chinese invention patent application CN101703636A discloses a kind of oil-soluble grape seed extract and preparation method thereof,
Containing 6~28 organic aliphatic acid and the NaOH mixing of carbon atom, heating reflux reaction obtains higher fatty acids sodium, will
Higher fatty acids sodium adds hydrochloric acid to be acidified, and takes its upper strata grease, at 25~130 DEG C, to instilling acylating agent in grease；With grape pip
Extract is solute, and organic solvent is solvent, and its solution instills the synthetic of above-mentioned acylation reaction, reaction at 30~90 DEG C
Decompression afterwards boils off its filtrate into sticky oil thing.
Though above two preparation method can prepare natural products, technique is complex, and need to add a large amount of solvents.Separately
Outward, the product that the emulsion process of Chinese invention patent CN101066075 is made stablizes poor, easily layering；Chinese invention patent
The chemical method of CN101703636A need to use long-time high-temperature process, and preparation time is long, not only consumes energy, and accessory substance is more, produces
The inoxidizability of product weakens.
The content of the invention
It is free from environmental pollution it is an object of the invention to provide one kind, it is easily isolated again, obtained product edible safety, performance
Stabilization, the method that the obvious enzyme process of antioxidant effect prepares fat-soluble grape pip procyanidin.
, because with reaction condition, gently, regioselectivity is strong, accessory substance is few, flow is simply controllable etc. excellent for enzyme process molecular modification
Point is increasingly becoming a kind of new method of substituted chemistry synthesis.Lipase is one of most important biocatalyst in industrial production,
Immobilized lipase is used widely in the food industry because of its good stability and catalysis activity.In enzyme process acidization
In, select suitable enzyme most important.Present invention discover that 9 kinds are applied to the lipase that flavone compound is acylated, respectively fat
Fat enzyme CALB, lipase 435, lipase RMIM, lipase TLIM, lipase IM, lipase TL100L, lipase CRL, onion
Pseudomonas Lipases and candida rugosa lipase.The present invention prepares fat-soluble grape pip procyanidin using enzyme process, leads to
Change reaction condition is crossed, fat-soluble grape pip procyanidin is prepared.The present invention can improve product stability, shorten preparation time,
Strengthen edible safety, avoid environmental pollution.The inventive method was both free from environmental pollution with lipase as catalyst, was easy to again point
From；Obtained product edible safety, can be added in edible oil, stable performance with arbitrary proportion, and antioxidant effect substantially, and is made
Standby process is simple is controllable.
The purpose of the present invention is achieved through the following technical solutions：
A kind of method that enzyme process prepares fat-soluble grape pip procyanidin, comprises the following steps：
(1) grape pip procyanidin is mixed with the organic aliphatic acid containing 2~30 carbon atoms, addition solvent, 20~
0.1~10h is stirred at 90 DEG C；
(2) add immobilized lipase as catalyst, heating stirring reacts 1~48h at 20~90 DEG C；The fixation
Change lipase is lipase CALB, lipase 435, lipase RMIM, lipase TLIM, lipase IM, lipase TL100L, fat
Any one in fat enzyme CRL, Pseudomonas cepacia lipase and candida rugosa lipase；
(3) lipase is separated, terminating reaction, decompression boils off its filtrate after reaction, obtains the sticky oil thing of aubergine, is
The fat-soluble grape pip procyanidin of synthesis.
Further to realize the object of the invention, it is preferable that described to contain 2~30 organic aliphatic acids of carbon atom for bay
Acid, palm fibre are put one or more in acid, stearic acid, oleic acid and linoleic acid.
Further preferably, the organic aliphatic acid is containing 8~22 unrighted acids of carbon atom.
Preferably, the grape pip procyanidin and the mass ratio of organic aliphatic acid are 10:1~1:50.
Preferably, the solvent is one or more in water, ethanol, acetone, ethyl acetate and petroleum ether.
Preferably, it is 20 with the mass ratio of grape pip procyanidin to add solvent:1~1:40.
Preferably, it is 1 with the mass ratio of grape pip procyanidin to add immobilized lipase:100~1:1.
Preferably, the device that decompression boils off its filtrate is Rotary Evaporators, and temperature is 30~90 DEG C.
Obtained product of the invention can be added in edible oil with arbitrary proportion, and antioxidant effect is obvious, stable performance, and
The quality of original grease is kept, obtained product edible safety, preparation process is simple is controllable.
Compared with prior art, the present invention has advantages below：
(1) enzyme process prepares fat-soluble grape pip procyanidin, the tradition side such as emulsion process than prior art CN101066075
Method stable performance, edible safety.Can be added in edible oil with arbitrary proportion；
(2) enzyme process prepares fat-soluble grape pip procyanidin, and its lipase has the selectivity and selectivity of height, compares
Prior art CN101703636A chemical methods, target product is easily separated；
(3) enzyme process prepares fat-soluble grape pip procyanidin, and the reaction than prior art CN101703636A chemical methods is walked
It is rapid less, it is simple controllable；
(4) enzyme process prepares fat-soluble grape pip procyanidin, and it is catalyst that it uses immobilized lipase, compared to existing skill
The base catalyst of art CN101703636A chemical methods, accessory substance is few, does not produce alkali waste to pollute environment, and be easily isolated.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of the raw material grape pip procyanidin of embodiment 1.
Fig. 2 is the infrared spectrogram of the fat-soluble grape pip procyanidin of products therefrom of embodiment 1.
Fig. 3 is the HPLC spectrograms of the raw material grape pip procyanidin of embodiment 1.
Fig. 4 is the HPLC spectrograms of the fat-soluble grape pip procyanidin of products therefrom.
Specific embodiment
To more fully understand the present invention, the present invention is described further with reference to the accompanying drawings and examples, it is necessary to illustrate
, embodiment do not constitute the limitation to the claimed scope of the invention.
Embodiment 1：
5g grape pip procyanidins are mixed with 20g laurate, 1L acetone is added, 2h is stirred at 40 DEG C.Add immobilization
Used as catalyst, heating stirring reacts 8h to lipase 435 (Hangzhou Chuan Ke bio tech ltd) at 45 DEG C.It is solid from adding
Immobilized lipase rises and starts timing, lipase is separated, terminating reaction, and decompression boils off its filtrate, remaining aubergine after reaction
Sticky oil thing, the fat-soluble grape pip procyanidin product for as synthesizing.After testing, the fat-soluble grape pip original cyanine of gained
Plain ethyl acetate solubility is 1.6g/100g, and its conversion ratio is 77%.
Embodiment 2：
5g grape pip procyanidins are mixed with 50g palmitic acids, 5L ethanol is added, 4h is stirred at 50 DEG C.Add immobilization
Used as catalyst, heating stirring reacts 12h to lipase RMIM (Hangzhou Chuan Ke bio tech ltd) at 60 DEG C.From addition
Immobilized lipase rises and starts timing, lipase is separated, terminating reaction, and decompression boils off its filtrate after reaction, remaining purplish red
The sticky oil thing of color, the fat-soluble grape pip procyanidin product for as synthesizing.After testing, the former flower of the fat-soluble grape pip of gained
Blue or green element ethyl acetate solubility is 2.4g/100g, and its conversion ratio is 73%.
Embodiment 3：
5g grape pip procyanidins are mixed with 1g linoleic acid, 2L petroleum ethers are added, 1h is stirred at 50 DEG C.Add immobilization
Used as catalyst, heating stirring reacts 5h to lipase TLIM (Hangzhou Chuan Ke bio tech ltd) at 50 DEG C.From addition
Immobilized lipase rises and starts timing, lipase is separated, terminating reaction, and decompression boils off its filtrate after reaction, remaining purplish red
The sticky oil thing of color, the fat-soluble grape pip procyanidin product for as synthesizing.After testing, the former flower of the fat-soluble grape pip of gained
Blue or green element ethyl acetate solubility is 1.3g/100g, and its conversion ratio is 61%.
Embodiment 4：
5g grape pip procyanidins are mixed with 5g soy(a)-bean oil fatty acids, 100ml distilled water is added, 0.5h is stirred at 30 DEG C.
Immobilized lipase CALB (Hangzhou Chuan Ke bio tech ltd) is added as catalyst, the heating stirring reaction at 40 DEG C
18h.The timing since adding immobilized lipase, lipase is separated, terminating reaction, and decompression boils off its filtrate after reaction,
The sticky oil thing of remaining aubergine, the fat-soluble grape pip procyanidin product for as synthesizing.After testing, gained is fat-soluble
Grape pip procyanidin ethyl acetate solubility is 3.1g/100g, and its conversion ratio is 82%.
The gained sample of embodiment 1 is tested and analyzed using FT-RI and HPLC-MS, other embodiment situation is as implemented
Example is similar, does not provide one by one；The test acquired results of embodiment 1 are as follows：
FT-RI (VERTEX33, Bruker) uses pellet technique, is tested according to the regulation of GB/T6040.Such as
Shown in Fig. 1 and Fig. 2；After testing, the infrared spectrum of fat-soluble grape pip procyanidin is compared with grape pip procyanidin,
3400cm‐1The phenolic hydroxyl group absworption peak of left and right weakens significantly, shows the water-soluble reduction of original matter, 1700cm‐1Nearby occur strong
Ester carbonyl group absworption peak, shows the fat-soluble enhancing of novel substance, and grape pip procyanidin is acylated after reaction.Its principle is mainly Portugal
The phenolic hydroxyl group of grape seed OPC generates ester carbonyl group, and fat-soluble group is transformed into by water soluble group.
Waters2998 high performance liquid chromatography (HPLC) separation condition is：Analytical column Waters C18 (4.6mm × 250mm
ID, 5.0 μm)；Detection wavelength 280nm；28 DEG C of column temperature；The μ L of sample size 20；Flow velocity 1mL/min；Mobile phase：First alcohol and water.
Linear gradient elution program：0-5min, 5-25% methyl alcohol；5-20min, 25% methyl alcohol；20-25min, 25-30%
Methyl alcohol；25-40min, 30% methyl alcohol；40-45min, 30-100% methyl alcohol；45-60min, 100% methyl alcohol.
MS detections are carried out by Thermo Scientific LCQ Ion-Trap Mass Spectrometer, mass spectrum bar
Part is as follows：ESI+, capillary voltage 3.5kV, m/z 50-2000.
GSP-o is analyzed using HPLC-MS/MS, is as a result seen Fig. 3,4, it is seen that grape pip procyanidin is being retained
After time 40min, almost occur without other materials, and modified grape pip procyanidin has after retention time 40min
More than 10 kinds materials are present, and 7 kinds of main matters, the respectively palmitic acid of epigallocatechin two are further determined that using mass spectrum
Ester, catechin tripalmitate, PB1 dipalmitate, the palmitate of epicatechin four, epicatechin gallate
Ester dipalmitate, PC1 tripalmitate, OPC A2 dipalmitates.By table 1, (grape pip of embodiment 1 is former
Anthocyanidin before modified after constituent analysis situation table) understand, these materials are mainly grape pip procyanidin by two, three and four
Substitution acylation reaction is obtained, and illustrates that the esterification of grape pip procyanidin is completed.
Compared with the conventional methods such as the emulsion process with prior art CN101066075, product is obtained in the embodiment of the present invention
Enzyme process prepares fat-soluble grape pip original cyanine, and the esterification for belonging to, product property stabilization is fat-soluble good, can be with arbitrary proportion
It is added in edible oil, antioxidant effect substantially, and keeps the quality of original grease.
Enzyme process of the present invention prepares fat-soluble grape pip procyanidin, and it is catalyst that it uses immobilized lipase, compared to existing
There is the base catalyst of technology CN101703636A chemical methods, accessory substance is few, do not produce alkali waste to pollute environment, and be easy to point
From.There is the selectivity and selectivity of height because of lipase, compared to existing technology CN101703636A chemical methods, the present invention need not
Regulation pH, need to only separate lipase, and decompression boils off its filtrate, you can target product is easily separated.
Embodiment of the present invention raw material is all food grade materials, and for enzyme process reacts, without side reaction, reaction is gentle, so system
The product edible safety for obtaining, preparation process is simple is controllable.
The grape pip procyanidin of 1 embodiment of table 1 before modified after constituent analysis situation table
Claims (8)
1. a kind of method that enzyme process prepares fat-soluble grape pip procyanidin, it is characterised in that comprise the following steps：
(1) grape pip procyanidin is mixed with the organic aliphatic acid containing 2~30 carbon atoms, adds solvent, 20~90 DEG C
0.1~10h of lower stirring；
(2) add immobilized lipase as catalyst, heating stirring reacts 1~48h at 20~90 DEG C；The immobilization fat
Fat enzyme is lipase CALB, lipase 435, lipase RMIM, lipase TLIM, lipase IM, lipase TL100L, lipase
Any one in CRL, Pseudomonas cepacia lipase and candida rugosa lipase；
(3) lipase is separated, terminating reaction, decompression boils off its filtrate after reaction, obtains the sticky oil thing of aubergine, is synthesis
Fat-soluble grape pip procyanidin.
2. the method that enzyme process according to claim 1 prepares fat-soluble grape pip procyanidin, it is characterised in that：It is described to contain
2~30 organic aliphatic acids of carbon atom are laurate, brown one or more put in acid, stearic acid, oleic acid and linoleic acid.
3. the method that enzyme process according to claim 1 and 2 prepares fat-soluble grape pip procyanidin, it is characterised in that：Institute
It is containing 8~22 unrighted acids of carbon atom to state organic aliphatic acid.
4. the method that enzyme process according to claim 1 prepares fat-soluble grape pip procyanidin, it is characterised in that：The Portugal
Grape seed OPC is 10 with the mass ratio of organic aliphatic acid:1~1:50.
5. the method that enzyme process according to claim 1 prepares fat-soluble grape pip procyanidin, it is characterised in that：It is described molten
Agent is one or more in water, ethanol, acetone, ethyl acetate and petroleum ether.
6. the method that enzyme process prepares fat-soluble grape pip procyanidin according to claim 1 or 5, it is characterised in that：Plus
It is 20 to enter solvent with the mass ratio of grape pip procyanidin:1~1:40.
7. the method that enzyme process according to claim 1 prepares fat-soluble grape pip procyanidin, it is characterised in that：Add solid
Immobilized lipase is 1 with the mass ratio of grape pip procyanidin:100~1:1.
8. the method that enzyme process according to claim 1 prepares fat-soluble grape pip procyanidin, it is characterised in that：It is described to subtract
The device that pressure boils off its filtrate is Rotary Evaporators, and temperature is 30~90 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611087009.6A CN106755162B (en) | 2016-12-01 | 2016-12-01 | Method for preparing fat-soluble grape seed procyanidin by enzyme method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611087009.6A CN106755162B (en) | 2016-12-01 | 2016-12-01 | Method for preparing fat-soluble grape seed procyanidin by enzyme method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106755162A true CN106755162A (en) | 2017-05-31 |
| CN106755162B CN106755162B (en) | 2020-10-30 |
Family
ID=58914016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611087009.6A Active CN106755162B (en) | 2016-12-01 | 2016-12-01 | Method for preparing fat-soluble grape seed procyanidin by enzyme method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106755162B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110240794A (en) * | 2019-05-06 | 2019-09-17 | 阜阳大可新材料股份有限公司 | A kind of mould proof fiber board adhesive |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101935587A (en) * | 2010-08-23 | 2011-01-05 | 江苏格林生物科技有限公司 | Process method for producing alpha-linolenic acid edible oil |
| CN102432582A (en) * | 2011-12-29 | 2012-05-02 | 广西金宏昕生物科技有限公司 | Preparation method of proanthocyanidin |
| CN102747117A (en) * | 2012-07-28 | 2012-10-24 | 江南大学 | Method for synthetizing liposoluble tea polyphenols by enzymic method |
| CN104140985A (en) * | 2014-07-10 | 2014-11-12 | 华南理工大学 | Antioxidant grease prepared in situ by enzymatic catalysis and method |
| CN104178531A (en) * | 2014-08-23 | 2014-12-03 | 中国农业科学院油料作物研究所 | Method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil |
| CN105936922A (en) * | 2016-06-02 | 2016-09-14 | 北京化工大学 | Method for enzymatic transesterfication preparation of cocoa butter equiralent by using 33-DEG C palm oil |
-
2016
- 2016-12-01 CN CN201611087009.6A patent/CN106755162B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101935587A (en) * | 2010-08-23 | 2011-01-05 | 江苏格林生物科技有限公司 | Process method for producing alpha-linolenic acid edible oil |
| CN102432582A (en) * | 2011-12-29 | 2012-05-02 | 广西金宏昕生物科技有限公司 | Preparation method of proanthocyanidin |
| CN102747117A (en) * | 2012-07-28 | 2012-10-24 | 江南大学 | Method for synthetizing liposoluble tea polyphenols by enzymic method |
| CN104140985A (en) * | 2014-07-10 | 2014-11-12 | 华南理工大学 | Antioxidant grease prepared in situ by enzymatic catalysis and method |
| CN104178531A (en) * | 2014-08-23 | 2014-12-03 | 中国农业科学院油料作物研究所 | Method for producing functional grease containing rich phytosterin ester from high-acid-value vegetable oil |
| CN105936922A (en) * | 2016-06-02 | 2016-09-14 | 北京化工大学 | Method for enzymatic transesterfication preparation of cocoa butter equiralent by using 33-DEG C palm oil |
Non-Patent Citations (1)
| Title |
|---|
| 王丹丹等: "蓝莓、紫薯与葡萄籽原花青素提取及其清除自由基能力的比较", 《辽东学院学报( 自然科学版)》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110240794A (en) * | 2019-05-06 | 2019-09-17 | 阜阳大可新材料股份有限公司 | A kind of mould proof fiber board adhesive |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106755162B (en) | 2020-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Caldas et al. | Phenolic compounds recovery from grape skin using conventional and non-conventional extraction methods | |
| Ghafoor et al. | Supercritical fluid extraction of phenolic compounds and antioxidants from grape (Vitis labrusca B.) seeds | |
| Fu et al. | Microwave and enzyme co-assisted aqueous two-phase extraction of polyphenol and lutein from marigold (Tagetes erecta L.) flower | |
| Qin et al. | Application of ionic liquid-based ultrasound-assisted extraction of five phenolic compounds from fig (Ficus carica L.) for HPLC-UV | |
| Haminiuk et al. | Phenolic compounds in fruits–an overview | |
| Sójka et al. | Transfer and mass balance of ellagitannins, anthocyanins, flavan-3-ols, and flavonols during the processing of red raspberries (Rubus idaeus L.) to juice | |
| Xu et al. | Subcritical water extraction and antioxidant activity evaluation with on-line HPLC-ABTS·+ assay of phenolic compounds from marigold (Tagetes erecta L.) flower residues | |
| Kitrytė et al. | Consecutive high-pressure and enzyme assisted fractionation of blackberry (Rubus fruticosus L.) pomace into functional ingredients: Process optimization and product characterization | |
| JPWO2006049258A1 (en) | High molecular weight polyphenol extracted from fermented tea, mitochondrial disease therapeutic agent, diabetes preventive/therapeutic agent, and food and drink | |
| Muangrat et al. | Physicochemical properties and antioxidant activity of oil extracted from Assam tea seeds (Camellia sinensis var. assamica) by supercritical CO2 extraction | |
| Sosnowska et al. | Effects of fruit extracts on pancreatic lipase activity in lipid emulsions | |
| Yuliani et al. | Optimization of genistein and daidzein extraction from a tempeh-fermented product of soybean | |
| Jabbar et al. | Nutritional, phytochemical characterization and antioxidant capacity of Ningxia Wolfberry (Lycium barbarum L.) | |
| Ihsanpuro et al. | Extract with high 1, 1-diphenyl-2-picrylhydrazyl (DPPH) inhibitory capability from pericarp and seed of mangosteen (Garcinia mangostana L.) using microwave-assisted extraction (MAE) two-phase solvent technique | |
| Sarria-Villa et al. | Isolation of catechin and gallic acid from Colombian bark of Pinus patula | |
| CN106755162A (en) | A kind of method that enzyme process prepares fat-soluble grape pip procyanidin | |
| CN109438213B (en) | Isopentenyl chalcone compound and preparation method thereof | |
| Myers et al. | Identification of native catechin fatty acid esters in green tea (Camellia sinensis) | |
| Gong et al. | Supercritical CO2 extraction of oleoresin from marigold (Tagetes erecta L.) flowers and determination of its antioxidant components with online HPLC‐ABTS•+ assay | |
| Zhao et al. | Extraction and characterization of radish seed oils using different methods | |
| Chemat et al. | Optimization of procedures for in-line extraction of lipids and polyphenols from grape seeds | |
| CN112552315A (en) | Purification method of Barosavirenz and derivatives thereof | |
| JP2008308630A (en) | Antioxidant derived from compositae plant, method for producing the same, and 2,4-hexadienal derivative | |
| JP2017019756A (en) | Tomato extract and its producing method, and food and drink and cosmetic including tomato extract | |
| JP2006052197A (en) | Cosmetic and method for producing the same |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |