CN106983871A - A kind of preparation method of large biological molecule compound stable state quercetagetin - Google Patents
A kind of preparation method of large biological molecule compound stable state quercetagetin Download PDFInfo
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- CN106983871A CN106983871A CN201710206621.9A CN201710206621A CN106983871A CN 106983871 A CN106983871 A CN 106983871A CN 201710206621 A CN201710206621 A CN 201710206621A CN 106983871 A CN106983871 A CN 106983871A
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- quercetagetin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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Abstract
The invention discloses a kind of preparation method of large biological molecule compound stable state quercetagetin, the transmission system technical field belonged in function factor stable state technology.This method is using zeins and propylene glycol alginate as raw material, using quercetagetin as bioactive substance, the zeins propylene glycol alginate large biological molecule compound of load quercetagetin is prepared using anti-solvent coprecipitation, the wherein mass ratio of zeins and propylene glycol alginate is 40:1~1:10, the addition of quercetagetin is 0.1wt%~2.0wt%.The macromolecular complex is after drying in spongy, significantly increase the water solubility of quercetagetin, the embedding rate of quercetagetin more than 90% and 6% 15% load capacity are realized, its light degradation and thermal degradation speed is effectively reduced, hence it is evident that improve its bioavailability.The implementation of the present invention can provide new approaches and new way for function factor stable state.
Description
Technical field
The invention belongs to the transmission system technical field in function factor stable state technology, and in particular to a kind of biological big point
The preparation method of sub- compound stable state quercetagetin.
Background technology
Quercetagetin is as a kind of polyhydroxy flavone compound, with anti-oxidant, anticancer, anti-inflammatory, antibacterial, disease-resistant
The various biological such as poison function and pharmacological action, can effective prevention of cardiovascular disease, significantly improve body immunity.However,
Quercetagetin is insoluble in water, sensitive to light, heat, oxygen, easily degrades, bioavailability is low, hence it is evident that limit its
Application in field of food.Now there are some researches show, polysaccharide and protein-based large biological molecule because its is safe, biodegradable and
The advantage, embedding, protection and transmission available for various bioactivators such as stability is strong.
Zeins is as a kind of edible natural phytoprotein, with renewable, nontoxic, amphipathic and good
Biocompatibility and degradability, by being self-assembly of microballoon or nano particle, can be usually used in the embedding of function factor with
Transmission.But dissolubility of the single zeins colloidal solid in water is poor, to thermo-responsive, this strongly limits it
Application in water-soluble food system.Now there are some researches show zeins can pass through noncovalent interaction with polysaccharide
Form compound.Such as zeins passes through hydrogen bond, Van der Waals force, hydrophobic interaction shape with chitosan and beet pectin
Into composite particles.It is and amphipathic however, focus primarily upon hy-drophilic polysaccharide about the research of zeins and polysaccharide at present
The research of polysaccharide interaction still belongs to blank.
Propylene glycol alginate, is to occur the linear polymeric polysaccharide of esterification generation by alginic acid and propane oxide, main
Chain is made up of α-L- guluronic acids and beta-D-mannuronic acid, can be with fat because the propylene-glycol-based in molecule is lipophilic end
Fat chou is closed, and the uronic acid in molecule is water-wet side, containing great amount of hydroxy group and part carboxyl, can be combined with protein.Therefore,
Alginate propylene glycol ester molecule has two kinds of groups of hydrophily and lipophile concurrently, with good surface-active and emulsion stability, fits
For dairy products, milk beverage, frozen food etc..The present invention intends preparing compound using zeins and propylene glycol alginate
Grain is used to embedding and protecting quercetagetin.
It is the anti-solvent precipitation method, also known as liquid-liquid dispersions method or phase separation currently used for colloidal solid most common method is prepared
Method.This method is applied to drip containing a kind of solution of component to prepare colloidal solid in another solution of polarized difference,
Organic solution containing two or more components can also be prepared into composite colloid particle using anti-solvent method, this kind of method is referred to as anti-molten
Agent coprecipitation, has been used for embedding of the zeins to various bioactivators, such as Quercetin, curcumin and white black false hellebore
Alcohol.
The present invention is using zeins, propylene glycol alginate as raw material, using quercetagetin to be representative biological living
Property material, using anti-solvent coprecipitation prepare load quercetagetin zeins-propylene glycol alginate be combined
Thing.The present invention not only significantly improves the water solubility of quercetagetin, and significantly improves its embedding rate and load capacity, has
Effect reduces its light degradation and thermal degradation speed, its bioavailability is significantly improved, while being provided for function factor stable state
New way.
The content of the invention
The present invention is low for water-soluble poorly water-soluble, the bioavailability sensitive to light, heat, oxygen of quercetagetin
Not enough there is provided a kind of preparation method of large biological molecule compound stable state quercetagetin, it is characterised in that with corn alcohol
Molten albumen and propylene glycol alginate are raw material, using quercetagetin as bioactive substance, and legal system is co-precipitated using anti-solvent
Zeins-propylene glycol alginate large biological molecule compound of standby load quercetagetin, comprises the following steps：
(1) dissolve：Zeins, propylene glycol alginate, quercetagetin are dissolved in ethanol water simultaneously,
Magnetic agitation is to being completely dissolved；
(2) anti-solvent is co-precipitated：The zeins that is obtained step (1) using syringe, propylene glycol alginate and
Quercetagetin ethanol water is expelled in distilled water, magnetic agitation in injection process, forms zeins-alginic acid
Propylene glycol ester-quercetagetin ternary complex dispersion liquid；
(3) rotary evaporation：Zeins-propylene glycol alginate-quercetagetin three that step (2) is obtained
First compound dispersion liquid removes part second alcohol and water using decompression rotary evaporation, prepares ternary complex concentrate；
(4) centrifuge：The ternary complex concentrate that step (3) is obtained, centrifugation removes particle aggregate, obtains ternary and answers
Compound seminal fluid；
(5) dry：The ternary complex seminal fluid that step (4) is obtained carries out vacuum freeze drying or spray drying, prepares
Go out to load zeins-propylene glycol alginate large biological molecule compound of quercetagetin.
The mass ratio of zeins and propylene glycol alginate described in step (1) is 40:1~1:10, the longevity of quercitrin ten thousand
The addition of chrysanthemum element is zeins and 0.1wt%~2.0wt% of propylene glycol alginate quality summation, ethanol water
The volume fraction of middle ethanol is 60%~90%.
Injection speed described in step (2) is 5mL/min, mixing speed 200r/min, zeins, alginic acid the third two
The volume ratio 1 of alcohol ester and quercetagetin ethanol water and distilled water:10~1:1.
The pressure of decompression rotary evaporation described in step (3) is -0.1MPa, and temperature is 30~60 DEG C, rotary speed 200
~500r/min, evaporation time is 10~50min, and the ternary complex volume of concentrate is the 1/ of ternary complex dispersion liquid volume
2~1/10.
Centrifugal rotational speed described in step (4) is 3000~6000r/min, and centrifugation time is 10~60min.
The temperature of vacuum freeze drying described in step (5) is -40~-60 DEG C, and the time is 2~10h；Be spray-dried into
150~180 DEG C of material temperature degree, drop temperature is 80 DEG C.
Zeins-propylene glycol alginate large biological molecule of load quercetagetin described in step (5)
The embedding rate of quercetagetin is more than 90% in compound, and load capacity is 6.2%~15.4%, effectively reduces its light degradation
With thermal degradation speed, hence it is evident that improve its bioavailability.
Beneficial effects of the present invention：The present invention is using natural biological macromolecular zeins and propylene glycol alginate as original
Material, using the quercetagetin with the various biological function such as anti-oxidant, anticancer, anti-inflammatory as representative bioactive substance,
Zeins-alginate propylene glycol ester complexes of load quercetagetin are prepared using anti-solvent coprecipitation first.
The compound is in spongy and with exclusive fruit tree, not only significantly improves the water solubility of quercetagetin, and
And its embedding rate and load capacity are significantly improved, its light degradation and thermal degradation speed are effectively reduced, its biological profit is significantly improved
With rate.The present invention's is embodied as function factor stable stateization there is provided new way.
Brief description of the drawings
Fig. 1 is that zeins-propylene glycol alginate of anti-solvent coprecipitation preparation load quercetagetin is multiple
Compound schematic diagram；
Fig. 2 is the structural representation of zeins-alginate propylene glycol ester complexes of load quercetagetin；Figure
Middle 1- zeins；2- propylene glycol alginates；3- quercetagetins；4- loads the molten egg of quercetagetin corn alcohol
In vain-alginate propylene glycol ester complexes；5- fruit tree shape micro-structurals；The spongy lyophilized products of 6-.
Embodiment
The invention provides a kind of preparation method of large biological molecule compound stable state quercetagetin, with reference to attached
The invention will be further described with embodiment for figure, but not limitation of the present invention.
Embodiment 1
As shown in figure 1, by 0.4g zeins, 0.08g propylene glycol alginates (both mass ratioes 5:1) 20mg quercitrins
Patuletin is dissolved in the ethanol solution that 40mL volume fractions are 80%, and magnetic agitation makes it fully dissolve.Will with syringe
The above-mentioned solution of 40mL, which is injected into the large beaker for filling 120mL water, does not stop stirring, and mixing speed is 200r/min, is formed muddy
Turbid yellow solution, as zeins-propylene glycol alginate-quercetagetin ternary complex dispersion liquid.Using
Rotary evaporation concentration ternary complex dispersion liquid is depressurized, pressure is -0.1MPa, and temperature is 40 DEG C, and rotary speed 300r/min steams
The hair time is 30min, and the ternary complex volume of concentrate is the 1/4 of ternary complex dispersion liquid volume；Ternary complex is concentrated
Liquid centrifugation removes particle aggregate, and the rotating speed 4000r/min of centrifuge, centrifugation time 10min obtain ternary complex seminal fluid；
Ternary complex seminal fluid uses vacuum freeze drying, and drying temperature is -50 DEG C, and the time is 6h, obtains load quercetagetin
Zeins-alginate propylene glycol ester complexes.
Zeins-propylene glycol alginate compound wall materialses are 93.8% to the embedding rate of quercetagetin, load
Measure as 6.2%.After heating 30min through 95 DEG C, the retention rate of the quercetagetin without embedding is 40.21%, and is passed through
The retention rate of quercetagetin after zeins-propylene glycol alginate embedding is 96.49%；Through light degradation
After 120min, the retention rate of the quercetagetin without embedding is 44.06%, and through zeins-alginate propylene glycol
The retention rate of quercetagetin after ester embedding is 85.69%.Therefore, zeins-alginate propylene glycol ester complexes
Effectively reduce thermal degradation and the light degradation speed of quercetagetin.
Embodiment 2
As shown in figure 1, by 0.4g zeins, 0.2g propylene glycol alginates (both mass ratioes 2:1) 50mg quercitrins
Patuletin is dissolved in the ethanol solution that 40mL volume fractions are 70%, and magnetic agitation makes it fully dissolve.Will with syringe
The above-mentioned solution of 40mL, which is injected into the large beaker for filling 200mL water, does not stop stirring, and mixing speed is 500r/min, is formed muddy
Turbid yellow solution, as zeins-propylene glycol alginate-quercetagetin ternary complex dispersion liquid.Using
Rotary evaporation concentration ternary complex dispersion liquid is depressurized, pressure is -0.1MPa, and temperature is 50 DEG C, and rotary speed 300r/min steams
The hair time is 20min, and the ternary complex volume of concentrate is the 1/4 of ternary complex dispersion liquid volume；Ternary complex is concentrated
Liquid centrifugation removes particle aggregate, and the rotating speed 4000r/min of centrifuge, centrifugation time 10min obtain ternary complex seminal fluid；
Ternary complex seminal fluid ternary complex seminal fluid is using spray drying, and 180 DEG C of feeding temperature, drop temperature is 80 DEG C, is born
Carry zeins-alginate propylene glycol ester complexes of quercetagetin.
Zeins-propylene glycol alginate compound wall materialses are 91.7% to the embedding rate of quercetagetin, load
Measure as 10.8%.After heating 30min through 95 DEG C, the retention rate of the quercetagetin without embedding is 40.21%, and is passed through
The retention rate of quercetagetin after zeins-propylene glycol alginate embedding is 92.19%；Through light degradation
After 120min, the retention rate of the quercetagetin without embedding is 44.06%, and through zeins-alginate propylene glycol
The retention rate of quercetagetin after ester embedding is 80.52%.Therefore, zeins-alginate propylene glycol ester complexes
Effectively reduce thermal degradation and the light degradation speed of quercetagetin.
Embodiment 3
As shown in figure 1, by 0.4g zeins, 0.8g propylene glycol alginates (both mass ratioes 1:2) 100mg quercitrins
Patuletin is dissolved in the ethanol solution that 40mL volume fractions are 60%, and magnetic agitation makes it fully dissolve.Will with syringe
The above-mentioned solution of 40mL, which is injected into the large beaker for filling 200mL water, does not stop stirring, and mixing speed is 500r/min, is formed muddy
Turbid yellow solution, as zeins-propylene glycol alginate-quercetagetin ternary complex dispersion liquid.Using
Rotary evaporation concentration ternary complex dispersion liquid is depressurized, pressure is -0.1MPa, and temperature is 55 DEG C, and rotary speed 300r/min steams
The hair time is 15min, and the ternary complex volume of concentrate is the 1/4 of ternary complex dispersion liquid volume；Ternary complex is concentrated
Liquid centrifugation removes particle aggregate, and the rotating speed 4000r/min of centrifuge, centrifugation time 10min obtain ternary complex seminal fluid；
Ternary complex seminal fluid uses vacuum freeze drying, and drying temperature is -50 DEG C, and the time is 6h, obtains load quercetagetin
Zeins-alginate propylene glycol ester complexes.
Zeins-propylene glycol alginate compound wall materialses are 84.1% to the embedding rate of quercetagetin, load
Measure as 15.4%.After heating 30min through 95 DEG C, the retention rate of the quercetagetin without embedding is 40.21%, and is passed through
The retention rate of quercetagetin after zeins-propylene glycol alginate embedding is 82.27%；Through light degradation
After 120min, the retention rate of the quercetagetin without embedding is 44.06%, and through zeins-alginate propylene glycol
The retention rate of quercetagetin after ester embedding is 75.12%.Therefore, zeins-alginate propylene glycol ester complexes
Effectively reduce thermal degradation and the light degradation speed of quercetagetin.
Shown in Fig. 2, propylene glycol alginate is in elongated filamentary structure, zeins particle adsorbed close spherical in shape
In fiber surface, quercetagetin is largely embedded in fibrous inside, and small part is embedded by zeins, the compound
Just as the fruit tree of the full fruit of a knot, the zeins-alginate propylene glycol ester complexes for loading quercetagetin are dried
Afterwards in spongy, the water solubility of quercetagetin is significantly increased.
Claims (7)
1. a kind of preparation method of large biological molecule compound stable state quercetagetin, it is characterised in that with the molten egg of corn alcohol
White and propylene glycol alginate is raw material, using quercetagetin as bioactive substance, is prepared using anti-solvent coprecipitation negative
Zeins-propylene glycol alginate large biological molecule compound of quercetagetin is carried, is comprised the following steps：
(1) dissolve：Zeins, propylene glycol alginate, quercetagetin are dissolved in ethanol water simultaneously, magnetic force
Stirring is to being completely dissolved；
(2) anti-solvent is co-precipitated：Zeins, propylene glycol alginate and the quercitrin for being obtained step (1) using syringe
Patuletin ethanol water is expelled in distilled water, magnetic agitation in injection process, forms zeins-alginic acid the third two
Alcohol ester-quercetagetin ternary complex dispersion liquid；
(3) rotary evaporation：Zeins-propylene glycol alginate-quercetagetin ternary that step (2) is obtained is answered
Compound dispersion liquid removes part second alcohol and water using decompression rotary evaporation, prepares ternary complex concentrate；
(4) centrifuge：The ternary complex concentrate that step (3) is obtained, centrifugation removes particle aggregate, obtains ternary complex
Seminal fluid；
(5) dry：The ternary complex seminal fluid that step (4) is obtained carries out vacuum freeze drying or spray drying, prepares negative
Carry zeins-propylene glycol alginate large biological molecule compound of quercetagetin.
2. a kind of preparation method of large biological molecule compound stable state quercetagetin according to claim 1, it is special
Levy and be, the mass ratio of zeins and propylene glycol alginate described in step (1) is 40:1~1:10, quercitrin marigold
The addition of element for zeins and propylene glycol alginate quality summation 0.1wt%~2.0wt%, in ethanol water
The volume fraction of ethanol is 60%~90%.
3. a kind of preparation method of large biological molecule compound stable state quercetagetin according to claim 1, it is special
Levy and be, injection speed described in step (2) is 5mL/min, mixing speed 200r/min, zeins, alginic acid the third two
The volume ratio 1 of alcohol ester and quercetagetin ethanol water and distilled water:10~1:1.
4. a kind of preparation method of large biological molecule compound stable state quercetagetin according to claim 1, it is special
Levy and be, the pressure of the decompression rotary evaporation described in step (3) is -0.1MPa, and temperature is 30~60 DEG C, rotary speed 200
~500r/min, evaporation time is 10~50min, and the ternary complex volume of concentrate is the 1/ of ternary complex dispersion liquid volume
2~1/10.
5. a kind of preparation method of large biological molecule compound stable state quercetagetin according to claim 1, it is special
Levy and be, centrifugal rotational speed described in step (4) is 3000~6000r/min, centrifugation time is 10~60min.
6. a kind of preparation method of large biological molecule compound stable state quercetagetin according to claim 1, it is special
Levy and be, the temperature of the vacuum freeze drying described in step (5) is -40~-60 DEG C, and the time is 2~10h；Be spray-dried into
150~180 DEG C of material temperature degree, drop temperature is 80 DEG C.
7. a kind of preparation method of large biological molecule compound stable state quercetagetin according to claim 1, it is special
Levy and be, zeins-propylene glycol alginate large biological molecule of the load quercetagetin described in step (5)
The embedding rate of quercetagetin is more than 90% in compound, and load capacity is 6.2%~15.4%, effectively reduces its light degradation
With thermal degradation speed, hence it is evident that improve its bioavailability.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109212094A (en) * | 2018-10-30 | 2019-01-15 | 晨光生物科技集团股份有限公司 | The detection method of quercetagetin in marigold residue |
| CN109805375A (en) * | 2019-01-28 | 2019-05-28 | 集美大学 | A kind of functional food and preparation method thereof improving organum visuale's oxidation resistance |
| CN113621440A (en) * | 2020-05-06 | 2021-11-09 | 晨光生物科技集团股份有限公司 | Grease composition with better stability |
| CN114098076A (en) * | 2021-11-18 | 2022-03-01 | 江南大学 | Preparation method of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles |
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| CN104225669A (en) * | 2014-08-25 | 2014-12-24 | 华南理工大学 | Bioactive bacterial cellulose-zein composite film and preparation method thereof |
Non-Patent Citations (1)
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| CUIXIA SUN ET AL.: "Binary Complex Based on Zein and Propylene Glycol Alginate for Delivery of Quercetagetin", 《BIOMACROMOLECULES》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109212094A (en) * | 2018-10-30 | 2019-01-15 | 晨光生物科技集团股份有限公司 | The detection method of quercetagetin in marigold residue |
| CN109212094B (en) * | 2018-10-30 | 2021-03-30 | 晨光生物科技集团股份有限公司 | Method for detecting quercitin in marigold dregs |
| CN109805375A (en) * | 2019-01-28 | 2019-05-28 | 集美大学 | A kind of functional food and preparation method thereof improving organum visuale's oxidation resistance |
| CN113621440A (en) * | 2020-05-06 | 2021-11-09 | 晨光生物科技集团股份有限公司 | Grease composition with better stability |
| CN114098076A (en) * | 2021-11-18 | 2022-03-01 | 江南大学 | Preparation method of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles |
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