CN106008626B - A kind of method of quick preparation black rice anthocyanin Cy-3-G - Google Patents
A kind of method of quick preparation black rice anthocyanin Cy-3-G Download PDFInfo
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- CN106008626B CN106008626B CN201610359790.1A CN201610359790A CN106008626B CN 106008626 B CN106008626 B CN 106008626B CN 201610359790 A CN201610359790 A CN 201610359790A CN 106008626 B CN106008626 B CN 106008626B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
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- C—CHEMISTRY; METALLURGY
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C07H1/08—Separation; Purification from natural products
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Abstract
The present invention relates to from a kind of from the method for 3 glucoside of black rice fast separating and purifying black rice anthocyanin Cyanidin.Concrete operations are as follows：Black rice is cleaned, is impregnated, ultramicro grinding is slurried；Extracting at constant temperature；It centrifuges, obtains Aqueous extracts；Then Fe is utilized3O4Nano-particle purifies, it is eluted with organic solvent, eluent is the refined solution of anthocyanidin, refined solution is concentrated by NF membrane, organic solvent is recycled, concentrate is freeze-dried, anthocyanidin powder is obtained, it is further detached by preparative high performance liquid chromatography again, obtains the high-purity separating liquid for containing only 3 glucoside of Cyanidin；Separating liquid is freeze-dried, 3 glucoside powder of Cyanidin is obtained.The entire extraction process of the present invention is green, environmentally friendly, pollution-free, and purifying uses Fe3O4Nano-particle, elution reagent can be recycled and be recycled by NF membrane；Using prepare liquid phase quickly, efficiently separate purifying, farthest reservation anthocyanidin monomer be not destroyed.
Description
Technical field
The invention belongs to the separating and purifying technology fields of food functionality natural products, and in particular to one kind is carried from black rice
Take the fast separating process of purifying anthocyanidin and Cy-3-G.
Background technology
Black rice is otherwise known as blood rice, purple rice, black rice, belongs to grass, full of nutrition, has " king in world's rice "
The good reputation of " black pearl ".Contain protein 11.5g in per 100g, 6.8% is higher by than general rice；Fatty 2.7g is higher than rice
Go out 1.9 times；Rich in vitamin B, B1, riboflavin, thiamine and iron, zinc, copper, selenium and other trace elements.In addition, also containing in black rice
The amino acid of necessary for human, total content are higher by general rice 15.9%, and lysine is higher by 3-5 times, and arginine is higher by 2.12 times,
The pattern of amino acid is closer to Human Body Model in what is more important black rice.One of the primary raw material of black rice or anthocyanidin.Flower
Green element, also known as anthocyanidin, are the water-soluble natural pigments that nature one kind is widely present in plant, belong to flavonoids,
It is also the main color-generation substance in plant petals, is known as after water, protein, fat, carbohydrate, vitamin, minerals
The seventh-largest essential nutrients later is a kind of organic active polyphenoils, has anti-oxidant, anti-aging, antitumor, drop blood
Fat improves the multiple efficacies such as immunity.
In recent years, a large amount of research has been carried out to the physiological function of anthocyanidin both at home and abroad, and achieve plentiful and substantial research at
Fruit.The study found that often edible anthocyanidin can obviously improve eyesight, alleviate hepatosis, inhibit tumor promotion, slow down old age
The deposition of spot, and have the function of resisting oxidation and delaying senility.Meanwhile anthocyanidin or a kind of safer natural pigment.
A large amount of exploitation anthocyanidin, can not only meet people to it as drug, cosmetics and health food the needs of, but also it is alternative right
The use of the harmful synthetic food color of human body.
Black rice is rich in anthocyanidin, and wherein Cy-3-G is the major monomeric compoent of black rice anthocyanin, is accounted for about
95% or more of black rice anthocyanin content.The extraction and purifying of anthocyanidin monomer are the important links in pigment production, are currently known
Method mostly using macroreticular resin and sephadex as purification media, these method extraction times are longer, purification steps troublesome, effect
The shortcomings of benefit is not high, and there are certain environmental pollutions.So anthocyanidin monomer higher price in the market, this is eating it
Being widely used for the fields such as product, medicine, cosmetics, health products causes direct influence, cannot be satisfied the straight of consumers in general
Connect demand.
Invention content
In order to reduce the purifying cost of anthocyanidin monomer, reduces anthocyanidin extraction process and the pollution caused by environment is asked
Topic, the present invention provide a kind of method quickly preparing black rice Cy-3-G.
A kind of operating procedure of the method for quick preparation black rice anthocyanin Cy-3-G is as follows：
（1）The impurity in black rice is removed, is soaked in water 0.5~3 hour；
（2）Black rice and water are pressed into 1 Kg of mass volume ratio:10~20 L carry out ultramicro grinding, obtain screened stock material；
（3）Extracting at constant temperature is carried out to slurry, obtains black rice slurries；
（4）Black rice slurries are centrifuged, anthocyanidin Aqueous extracts are obtained；
（5）By 20~30ml of volume mass volume ratio：Ferroso-ferric oxide is added in anthocyanidin Aqueous extracts in 1g（Fe3O4）It receives
Rice corpuscles, stir 1 hour or more, the ferroso-ferric oxide of anthocyanidin will be adsorbed with magnet（Fe3O4）Nano-particle is sucked out, and use is pure
Water purification elutes ferroso-ferric oxide（Fe3O4）Nanoparticle surface is not eluted by the substance of its absorption, then with organic solvent, eluent
As anthocyanidin refined solution；
（6）Anthocyanidin refined solution is concentrated by NF membrane, makes volume concentration to the 1/15 of anthocyanidin refined solution volume, divides
Concentrate and filter liquor are not obtained, and filter liquor is step（5）Organic solvent used；
（7）By concentrate vacuum freeze drying, the black rice anthocyanin powder of moisture≤5% is obtained；
（8）Black rice anthocyanin powder is recovered to concentrate with acid solution, it is further by preparative high performance liquid chromatography instrument
Separation, obtains the separating liquid for containing only Cy-3-G；
（9）By separating liquid vacuum freeze drying, the Cy-3-G of the aubergine of moisture≤5% is obtained
Powder, purity can reach 95% or more.
The technical solution further limited is as follows：
Step（1）In, black rice impregnates 0.5~3 hour in water.
Step（2）In, the average particle size of the material in the screened stock material is less than 50 μm.
Step（3）In, the pH that screened stock material is adjusted with the citric acid solution of 0.5~5.0mol/l of concentration is 2.5~5.5,
At 20~55 DEG C, extract 2~6 hours.
Step（4）In, using disc centrifuge, under 6000~10000 revs/min, solid-liquid is carried out to black rice slurries
Separation, except desizing, protein, polysaccharide.
Step（5）In, the organic solvent is ethyl alcohol, methanol, acetone, n-butanol, 1,3-PD, glycerine, second two
One kind in alcohol being based on environmental consideration, preferably 40 ~ 80% ethanol solution.
Step（6）In, the NF membrane is the NF membrane that molecular cut off is 200~300Da；It is 0.8 to concentrate pressure
20~45 DEG C of MPa, temperature.
Step（7）In, the concentrate carries out precooling, then in vacuum freeze drier, vacuum degree 0.05~
It is freeze-dried under the conditions of 0.1MPa, temperature -20~-40 DEG C.
Step（8）In, the preparative high performance liquid chromatography instrument elution requirement is：Mobile phase A is the first of volumetric concentration 10%
Acid, Mobile phase B are 25ml by volume：10 ml：40 ml：The acetonitrile of 25 ml：Formic acid：Water：The mixed solution of methanol uses
C18 column gradient elutions, Mobile phase B rises to 85% by 16% in flow velocity 1ml/min, 40~85min, Detection wavelength 520nm.
Step（9）In, vacuum freeze drying condition is 0.05~0.1MPa of vacuum degree, temperature -20~-40 DEG C.
The advantageous effects of the present invention embody in the following areas：
（1）It is environmentally safe
The extractant that the present invention uses is water, the entire free of contamination chemical reagent of extraction process, and purifying uses Fe3O4Nanometer
Particle can be recycled and be recycled by NF membrane after organic solvent elution enrichment, and other reagents are pollution-free to environment.It should
Method can be effectively saved energy consumption and environmental protection.
（2）It is effectively protected the stability of anthocyanidin monomer
In entire extraction, purification process, using medium temperature（20~60 DEG C）Extraction；Disk centrifugation is except starch etc.；Fe3O4It receives
Rice corpuscles purifies；Organic solvent is recycled in nanofiltration；Freeze-drying is dried, mild condition, farthest retains anthocyanidin monomer
It is not destroyed.
（3）Purifying process uses membrane separation technique
This research separates and recovers organic reagent using NF membrane, can not only concentrate, but also technology energy consumption is small, has safely
Effect, simple for process, operation is also convenient for, and automation is stronger.
（4）The breakthrough of black rice anthocyanin purification technique
For a long time, since the extracting method of anthocyanidin is of high cost, complex steps, recovery rate are low, it is constrained in food
And it is widely applied in other related fields.The anthocyanidin obtained by the method for the invention is through Fe3O4Nano-particle is big after purification
Its purity and yield are improved greatly, are conducive to isolate and purify monomer based on preparing liquid technology, and significantly shorten
Purification time, reduces the cost of traditional post separation.
（5）Preparative liquid chromatography separation prepares black rice anthocyanin Cy-3-G
It is isolated and purified through preparing liquid phase one-step, can fast and efficiently obtain the high-purity monomer of black rice anthocyanin.
Description of the drawings
Fig. 1 is the preparation solution phasor of black rice anthocyanin Cy-3-G.
Specific implementation mode
With reference to embodiment and attached drawing, the present invention is further described.
Embodiment 1
A kind of concrete operation step of quick preparation black rice anthocyanin Cy-3-G is as follows：
（1）Impurity elimination, immersion：Macroscopic impurity in black rice is removed, is then soaked in water half an hour；
（2）Ultramicro grinding：By mass volume ratio 1:10（Kg/L）Black rice and water are taken, ultramicro grinding is carried out, until feed liquid is flat
Equal granularity is less than 50 μm；
（3）Extraction：The pH that screened stock material is adjusted with the citric acid solution of concentration 0.5mol/l is 4.5, at 40 DEG C, extraction 4
Hour, obtain black rice slurries；
（4）It centrifuges：Using disc centrifuge, under 8000 revs/min, black rice slurries are separated by solid-liquid separation,
To remove desizing, protein, polysaccharide, Aqueous extracts are obtained；
（5）Fe3O4Nano-particle adsorbs anthocyanidin：1g Fe are added in 25ml anthocyanidin Aqueous extracts3O4Nano-particle,
Under the conditions of 500 r/min, magnetic agitation 2.0h, until most of anthocyanidin is by Fe3O4Nano-particle adsorbs；It will be inhaled with magnet again
Fe with anthocyanidin3O4Nano-particle is sucked out, first with pure water elution not by Fe3O4The substance of nano-particle absorption, then use
60% ethanol solution elution, eluent is anthocyanidin refined solution；
（6）Nanofiltration concentrates：Anthocyanidin refined solution is concentrated by the NF membrane that molecular cut off is 200Da, keeps volume dense
It is reduced to the 1/15 of refined solution volume, and recycles ethyl alcohol, 0.8 MPa of operating pressure, 25 DEG C of temperature respectively obtains concentrate and filters out
Liquid, filter liquor are 60% ethanol solution；
（7）Vacuum freeze drying：Concentrate is subjected to precooling, is then placed in vacuum freeze drier, in vacuum degree
0.1MPa, freeze-drying -25 DEG C of conditions of temperature, are freeze-dried to moisture≤5%, obtain the black rice anthocyanin powder of aubergine
End；
（8）Prepare Cy-3-G：Black rice anthocyanin powder is restored with acid solution, liquid is restored and passes through system
Standby type high performance liquid chromatograph further detaches, and splitter used is C18 columns, and mobile phase A is volumetric concentration 10%（V/V）'s
Formic acid, Mobile phase B are 25ml by volume：10 ml：40 ml：The acetonitrile of 25 ml：Formic acid：Water：The mixed solution of methanol, stream
Speed is 1ml/min, and Mobile phase B rises to 85% by 16% in 50min, Detection wavelength 520nm.As shown in Figure 1, main peak is to swear vehicle
Chrysanthemum element -3- glucosides, are collected its component；
（9）Vacuum freeze drying：Collection liquid is subjected to precooling, is then placed in vacuum freeze drier, in vacuum degree
0.1MPa, freeze-drying -25 DEG C of conditions of temperature, freeze-drying to moisture≤5% obtain aubergine powder, as corn flower
Element -3- glucoside powder.After testing, Cy-3-G powder purity is 99.5%.
Embodiment 2
A kind of concrete operation step of quick preparation black rice anthocyanin Cy-3-G is as follows：
（1）Impurity elimination, immersion：Macroscopic impurity in black rice is removed, is then soaked in water half an hour；
（2）Ultramicro grinding：By mass volume ratio 1: 20（Kg/L）Black rice and water are taken, ultramicro grinding is carried out, until feed liquid is flat
Equal granularity is less than 50 μm；
（3）Extraction：The pH that screened stock material is adjusted with the citric acid solution of concentration 1.5mol/l is 5.5, at 55 DEG C, extraction 6
Hour, obtain black rice slurries；
（4）It centrifuges：Using disc centrifuge, under 10000 revs/min, black rice slurries are separated by solid-liquid separation,
To remove desizing, protein, polysaccharide, Aqueous extracts are obtained；
（5）Fe3O4Nano-particle adsorbs anthocyanidin：1g Fe are added in 30ml anthocyanidin Aqueous extracts3O4Nano-particle turns
Speed 300 r/min, magnetic agitation 2.5h, until most of anthocyanidin is by Fe3O4Nano-particle adsorbs；It will be adsorbed with magnet again
The Fe of anthocyanidin3O4Nano-particle is sucked out, first with pure water elution not by Fe3O4The substance of nano-particle absorption, then with 75%
Ethanol solution elutes, and eluent is the refined solution of anthocyanidin；
（6）Nanofiltration concentrates：The refined solution of anthocyanidin is concentrated by the NF membrane that molecular cut off is 300Da, makes volume
It is concentrated to the 1/15 of refined solution volume, and recycles ethyl alcohol, 0.8 MPa of operating pressure, 35 DEG C of temperature respectively obtains concentrate and filter
Go out liquid, filter liquor is 75% ethanol solution；
（7）Vacuum freeze drying：Concentrate is subjected to precooling, is then placed in vacuum freeze drier, in vacuum degree
0.05MPa, freeze-drying -40 DEG C of conditions of temperature, freeze-drying to moisture≤5% obtain aubergine powder, as black rice
Anthocyanidin powder；
（7）Prepare Cy-3-G：Anthocyanidin freeze-dried powder is restored with acid solution, concentrate is passed through into system
Standby type high performance liquid chromatography further detaches, and splitter used is C18 columns, and mobile phase A is volumetric concentration 10%（V/V）First
Acid, Mobile phase B are 25ml by volume：10 ml：40 ml：The acetonitrile of 25 ml：Formic acid：Water：The mixed solution of methanol, flow velocity
For 1ml/min, Mobile phase B rises to 85% by 16% in 65min, and Detection wavelength is 520nm to Cy-3-G component
It is collected；
（8）Vacuum freeze drying：Separating liquid is subjected to precooling, is then placed in vacuum freeze drier, in vacuum degree
0.05MPa, freeze-drying -40 DEG C of conditions of temperature, freeze-drying to moisture≤5% obtain aubergine powder, as swear vehicle
Chrysanthemum element -3- glucoside powder.After testing, Cy-3-G powder purity is 98.7%.
Claims (4)
1. a kind of method of quick preparation black rice anthocyanin Cy-3-G, it is characterised in that specific operation step
It is rapid as follows：
（1）The impurity in black rice is removed, is soaked in water 0.5~3 hour；
（2）Black rice and water are pressed into 1 Kg of mass volume ratio:10~20 L carry out ultramicro grinding, obtain screened stock material, the screened stock material
In material average particle size be less than 50 μm；
（3）Extracting at constant temperature is carried out to slurry, the pH that screened stock material is adjusted with the citric acid solution of 0.5~5.0mol/l of concentration is 2.5
~5.5, at 20~55 DEG C, extracts 2~6 hours, obtain black rice slurries；
（4）Disc centrifuge is separated by solid-liquid separation black rice slurries under 6000~10000 revs/min, except desizing, egg
White matter, polysaccharide obtain anthocyanidin Aqueous extracts；
（5）By volume mass than 20~30ml：Ferroso-ferric oxide is added in anthocyanidin Aqueous extracts in 1g（Fe3O4）Nano-particle stirs
It mixes 1 hour or more, the ferroso-ferric oxide of anthocyanidin will be adsorbed with magnet（Fe3O4）Nano-particle is sucked out, with pure water elution four
Fe 3 O（Fe3O4）Nanoparticle surface is not eluted by the substance of its absorption, then with organic solvent, and eluent is anthocyanidin
Refined solution；
（6）Anthocyanidin refined solution is concentrated by NF membrane, the NF membrane is the nanofiltration that molecular cut off is 200~300Da
Film；Concentration pressure is 0.8 MPa, 20~45 DEG C of temperature；Make volume concentration to the 1/15 of anthocyanidin refined solution volume, respectively obtains
Concentrate and filter liquor, filter liquor are step（5）Organic solvent used；
（7）Concentrate is subjected to precooling, then in vacuum freeze drier, in 0.05~0.1MPa of vacuum degree, temperature -20
It is freeze-dried under the conditions of~-40 DEG C, obtains the black rice anthocyanin powder of moisture≤5%；
（8）Black rice anthocyanin powder is recovered to concentrate with acid solution, is further detached by preparative high performance liquid chromatography instrument,
Obtain containing only the separating liquid of Cy-3-G；Elution requirement is：Mobile phase A is the formic acid of volumetric concentration 10%,
Mobile phase B is 25ml by volume：10 ml：40 ml：The acetonitrile of 25 ml：Formic acid：Water：The mixed solution of methanol, using C18
Column gradient elution, Mobile phase B rises to 85% by 16% in flow velocity 1ml/min, 40~85min, Detection wavelength 520nm；
（9）By separating liquid vacuum freeze drying, vacuum freeze drying condition is 0.05~0.1MPa of vacuum degree, temperature -20~-40
℃；The Cy-3-G powder of the aubergine of moisture≤5% is obtained, purity can reach 95% or more.
2. a kind of method of quick preparation black rice anthocyanin Cy-3-G according to claim 1, special
Sign is：Step（4）In, using disc centrifuge.
3. a kind of method of quick preparation black rice anthocyanin Cy-3-G according to claim 1, special
Sign is：Step（5）In, the organic solvent is ethyl alcohol, methanol, acetone, n-butanol, 1,3-PD, glycerine, ethylene glycol
In one kind.
4. a kind of method of quick preparation black rice anthocyanin Cy-3-G according to claim 1, special
Sign is：Step（5）In, the organic solvent be 40 ~ 80% ethanol solution.
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| CN109706205B (en) * | 2018-02-28 | 2020-12-01 | 合肥工业大学 | Stable-performance black rice anthocyanin monomer and molecular modification preparation method |
| CN113262274B (en) * | 2021-05-13 | 2022-05-03 | 华中农业大学 | Black rice extract and preparation method and application thereof |
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