CN105456196B - Curcumin composite particles and its preparation method and application - Google Patents

Curcumin composite particles and its preparation method and application Download PDF

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Publication number
CN105456196B
CN105456196B CN201510819903.7A CN201510819903A CN105456196B CN 105456196 B CN105456196 B CN 105456196B CN 201510819903 A CN201510819903 A CN 201510819903A CN 105456196 B CN105456196 B CN 105456196B
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curcumin
composite particles
component
solution
composition
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CN105456196A (en
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张亚琼
姚芳懿
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Shanghai Jiaotong University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C11/00—Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/08—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing caseinates but no other milk proteins nor milk fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/1526—Amino acids; Peptides; Protein hydrolysates; Nucleic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/06—Treating tea before extraction; Preparations produced thereby
    • A23F3/14—Tea preparations, e.g. using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/10—Treating roasted coffee; Preparations produced thereby
    • A23F5/14—Treating roasted coffee; Preparations produced thereby using additives, e.g. milk, sugar; Coating, e.g. for preserving
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/66—Proteins
    • 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
    • A61K31/12—Ketones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1658—Proteins, e.g. albumin, gelatin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

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Abstract

The present invention provides a kind of curcumin composite particles and its preparation method and application.Specifically, the invention discloses a kind of curcumin composite particles, contain component (a) curcumin；Component (b) alcohol soluble protein；Component (c) casein, caseinate or casein derived object；Wherein, the component (a) and the component (b) are in admixture and are wrapped up by the component (c).Curcumin composite particles of the invention can significantly improve water-soluble, bioavilability and the stability of curcumin, have a good application prospect in functional food and field of medicaments.

Description

Curcumin composite particles and its preparation method and application
Technical field
The present invention relates to field of biotechnology, relates more specifically to a kind of curcumin composite particles and preparation method thereof and answer With.
Background technique
Curcumin is a kind of polyphenol compound extracted from the rhizome of herbaceos perennial turmeric, traditional Curcumin is typically all to be used as food dye and additive, in recent years, a large amount of research shows that curcumin has extensive physiology Active function, such as it is reducing blood lipid, antitumor, anti-inflammatory, cholagogue, anti-oxidant.However, dissolubility pole of the curcumin in aqueous environments Difference, and it is unstable；In addition curcumin also has sensibility to light, heat, these factors all constrain curcumin in different necks significantly The application in domain.The water-soluble of curcumin can be substantially improved by the nanometer system that selection suitable material building contains curcumin And stability.Selected material is synthetic polymer or matrix material (containing surfactant), bio-safety mostly at present There is hidden danger in property.
Therefore, there is an urgent need in the art to develop safe and reliable curcumin nano system.
Summary of the invention
The purpose of the present invention is to provide a kind of safe and reliable curcumin composite particles and its preparation method and application.
In the first aspect of the present invention, a kind of curcumin composite particles are provided, the composite particles contain:
Component (a): curcumin；
Component (b): alcohol soluble protein；
Component (c): it can on casein, bromatology or in pharmaceutically acceptable caseinate or bromatology or pharmaceutically connect The casein derived object received；
Wherein, component (a) curcumin and component (b) alcohol soluble protein are in admixture and by the components (c) it is wrapped up；
Also, the composite particles are hydrophilic particle.
In another preferred example, the curcumin composite particles have nucleocapsid structure.
In another preferred example, the nucleocapsid structure has hydrophobic core and hydrophilic outer shell.
In another preferred example, component (a) and component (b) are contained in the hydrophobic core, preferably component (a) and component (b) the sum of weight accounts for the 70-100wt% of hydrophobic nuclear weight, preferably 80-100wt%, more preferably 90-100wt%.
In another preferred example, the hydrophilic outer shell contains component (c), and preferably the weight of component (c) accounts for hydrophilic outer The 80-100wt% of the weight of shell, preferably 90-100wt%, more preferably 95-100wt%.
In another preferred example, the mass ratio of component (a) curcumin and component (b) alcohol soluble protein is (0.2-5): (5-100), preferably (0.5-3): (10-50) is more preferably (1-2): (10-20).
In another preferred example, the mass M of the component (c)cWith the quality sum of component (a) curcumin and component (b) Ma+bThe ratio between be (0.5-5): (0.8-1.2)；Preferably (0.8-4): (0.9-1.1)；More preferably it is (0.9-2): 1.
In another preferred example, the component (b) and component (c) mass ratio are (0.8-2): (0.8-2), more preferably for (0.8-1.2): 1.
In another preferred example, component (b) cladding component (a).
In another preferred example, the component (b) is 80-100% to the clad ratio of component (a), preferably 90-98%.
In another preferred example, the partial size of the curcumin composite particles is 50-500nm, preferably 100-400nm, more Good ground 120-300nm.
In another preferred example, the hydrophilic shell with a thickness of 20-150nm, preferably 50-100nm, more preferably for 60-80nm。
In another preferred example, the alcohol soluble protein includes zeins, wheat gliadin.
In another preferred example, the component (c) is caseinate.
In another preferred example, the caseinate include casein sodium, Caseins, potassium salts, calcium caseinate, Or combinations thereof.
In another preferred example, the curcumin composite particles have one or more features selected from the group below:
(i) bioavilability: bioavilability 50-80%, preferably 55-70%；
(ii) dissolubility: in water, solubility is 0.1-1mg/mL, more preferably 0.1-0.5mg/mL at 25 DEG C.
In another preferred example, prepared by method described in the curcumin composite particles fourth aspect present invention.
In the second aspect of the present invention, a kind of composition is provided, the composition includes (a) first aspect present invention institute The curcumin composite particles stated；(b) acceptable carrier in pharmaceutically acceptable carrier or bromatology.
In another preferred example, contain 0.001-99wt% in the composition, preferably 0.1-90wt%, more preferably 1- The curcumin composite particles of 80wt%, are based on the total weight of the composition.
In another preferred example, the composition includes pharmaceutical composition, Halth-care composition, meal supplement combination Object, beverage composition for treating dental erosion and food composition.
In the third aspect of the present invention, a kind of beverage composition for treating dental erosion is provided, the composition includes (a) first party of the present invention Curcumin composite particles described in face；(b) the upper acceptable carrier of beverage.
In another preferred example, the beverage composition for treating dental erosion also includes acceptable additive on food.
In another preferred example, the additive includes: sweetener, acidity regulator, electrolyte, and/or essence.
In another preferred example, the acidity regulator is used to adjust the pH value of the beverage composition for treating dental erosion.
In another preferred example, in the beverage composition for treating dental erosion, also comprising beverage base as load acceptable on food Body.
In another preferred example, the beverage base include coffee, tea, fruit juice, milk, milk replacer, dairy products, and/or Water.
In another preferred example, contain 0.001-99wt% in the beverage composition for treating dental erosion, preferably 0.1-90wt%, more preferably The curcumin composite particles of ground 1-80wt%, are based on the total weight of the composition.
In the fourth aspect of the present invention, provides and a kind of prepare curcumin composite particles described in first aspect present invention Method, the method includes the steps:
(i) the first solution and the second solution are provided, wherein
First solution includes the first solvent and component (a) curcumin and component (b) alcohol that are dissolved in the first solvent Molten albumen；
Second solution includes the second solvent and the component (c) being dissolved in the second solvent；
(ii) the first solution is mixed with the second solution, so that the curcumin for forming first aspect present invention is compound Particle.
In another preferred example, the method further comprises the steps of:
(iii) it to the curcumin composite particles formed in previous step, is separated；
(iv) it optionally carries out that the curcumin composite particles of previous step are dried.
In another preferred example, in step (ii), including the first solution the second solution of addition is formed containing the ginger The mixed liquor of flavine composite particles.
In another preferred example, in step (ii), including before mixing, among or later, to first solution, Second solution and/or mixed liquor are stirred.
In another preferred example, in step (ii), the addition includes being added dropwise.
In another preferred example, it in step (ii), after the first solution is added dropwise to the second solution, is stirred.
It in another preferred example, include: drying, drying, freeze-drying in step (iv) described drying.
In another preferred example, the mass concentration of alcohol soluble protein is 5-50mg/mL in first solution, preferably 15-25mg/mL。
In another preferred example, the mass concentration of curcumin is 0.1-10mg/mL in first solution, preferably 0.5-5mg/mL。
In another preferred example, the mass concentration of caseinate is 1-10mg/mL in second solution, preferably 1.5-2.5mg/mL。
In another preferred example, first solvent is selected from the group: alcohol, water/alcohol mixed solvent.
In another preferred example, water/alcohol in the mixed solvent, alcohol content 20-95vt%, preferably 40- 90vt%, more preferably 60-80vt%
In another preferred example, second solvent is selected from the group: water, alcohol, water/alcohol mixed solvent.
In another preferred example, as water/alcohol in the mixed solvent of the second solvent, alcohol content 0.1- 50wt%, preferably 1-40wt%, more preferably 2-30wt%
In another preferred example, the alcohols be 1-3 member lower alcohol, be selected from the group: methanol, ethyl alcohol, propyl alcohol, isopropanol, Or combinations thereof.
In another preferred example, the use volume ratio of first solution and second solution is 1-5:10-50, preferably Ground 1-2:10-20.
In another preferred example, the mixing time of the step c) stirring is 5-120min, preferably 10-80min.
In the fifth aspect of the invention, the purposes of curcumin composite particles as described in the first aspect of the invention is provided, It is used to prepare a composition, the composition is for reducing blood lipid, antitumor, anti-inflammatory, cholagogue, and/or anti-oxidant.
In another preferred example, the composition includes beverage composition for treating dental erosion, food compositions, pharmaceutical composition, health care Product composition.
It should be understood that above-mentioned each technical characteristic of the invention and having in below (eg embodiment) within the scope of the present invention It can be combined with each other between each technical characteristic of body description, to form a new or preferred technical solution.As space is limited, exist This no longer tires out one by one states.
Detailed description of the invention
Fig. 1 redissolves digital photograph figure in water after showing the freeze-drying of curcumin nano particle.
Fig. 2 shows the transmission electron microscope picture of curcumin nano particle.
Fig. 3 shows free curcumin compared with the DSC heat analysis for the curcumin being wrapped in nanometer system.
Fig. 4 shows curcumin nano system cumulative in vitro release profiles.
Fig. 5 shows that free curcumin compares (under the conditions of 180 DEG C with the thermal stability for being wrapped in curcumin in nanometer system Heating).
Fig. 6 shows variation (180 DEG C of conditions of curcumin nano system partial size and polydispersity index in a heated condition Lower heating).
Fig. 7 shows the transmission electron microscope picture of curcumin nano system under heating different time.Wherein, Fig. 7 A is 180 DEG C of items It is heated 10 minutes under part；Fig. 7 B is heated 60 minutes under the conditions of being 180 DEG C.
Fig. 8 shows that free curcumin compares with the light durability for being wrapped in curcumin in nanometer system.
Fig. 9 shows the particle diameter distribution situation of fresh preparation with the curcumin nanoparticles of freeze-drying rehydration
Figure 10 shows transmission electron microscope picture of the nanoparticle in 2M NaCl solution and 40% (w/v) sucrose system.Wherein, Figure 10 A is transmission electron microscope picture of the nanoparticle in 2M NaCl solution, and Figure 10 B is nanoparticle in 40% (w/v) sucrose system Transmission electron microscope picture.
Figure 11 shows Caco-2 cell to the free curcumin of same dose and is wrapped in taking the photograph for curcumin in nanoparticle Take rate result.Wherein, Figure 11 A, 11B, 11C and 11D respectively illustrate the intake time be 4h, for 24 hours, 48h and 72h when uptake ratio As a result (data are indicated with average value ± standard deviation.**p<0.01,***p<0.001).
Figure 12 shows the free curcumin of same dose and is wrapped in across the Caco-2 cell monolayer of curcumin in nanoparticle (data are indicated the efficiency of film with average value ± standard deviation.**p<0.01,***p<0.001).
Specific embodiment
The present inventor after extensive and in-depth study, unexpectedly develops a kind of curcumin composite particles for the first time.Experiment Show to be carrier using alcohol soluble protein and caseinate, property can be prepared by simple liquid-liquid dispersion method Stable curcumin composite particles, can significantly improve the water-soluble of curcumin, resist the quick of ultraviolet lighting and high-temperature heating Perception.On this basis, the present invention is completed.
Term
As used herein, term " containing ", "include", "comprise" can be open, semi-enclosed or enclosed.It changes Yan Zhi, and " by ... constitute ", " substantially by ... constitute " be also included in the range of the term.
As used herein, term " encapsulating ", " cladding " and " package " is used interchangeably, and refers to a certain encapsulating material or encapsulation object Matter by content packet inside it.
As used herein, term " composite particles of the present invention ", " Nano composite granules of the present invention ", " curcumin compound Grain ", " curcumin nano particle ", " curcumin nano system " etc. are used interchangeably, and are referred to and are contained described in first aspect present invention There is the particle of component (a), component (b) and component (c).Composite particles of the invention have nucleocapsid structure.
Alcohol soluble protein
Alcohol soluble protein (alcohol soluble protein) is one of the component of vegetable seeds storage albumen.It does not dissolve in Water dissolves in 50%~90% ethyl alcohol.
Zeins is also known as rice protein, and English name ZEIN is the protein for being 25000~45000 by average molecular weight The mixture of composition, it is formed alpha-helix body by the hydrogen bond action of hydroxyl and imino group in peptide backbone；There is bottom surface energy, has There is unique film forming characteristics.In alcohol solution, at random ball of string structure, but at a kind of transparent, glossy after solvent evaporation Film, there is moisture-proof, oxygen barrier, uvioresistant, protect perfume, oil resistance, the characteristics such as antistatic.
Caseinate
Caseinate, is the salt form of casein, and common caseinate includes casein sodium, caseinic acid Potassium, calcium caseinate etc..
Casein sodium is also known as casein sodium salt, casein sodium, be using fresh milk as raw material, will be in milk with sour curdling method The casein of content about 2.5% purifies, then is made through alkaline sodium reaction.Casein is not soluble in water, and the Sodium Caseinate after reacting With fabulous water solubility.It contains the various essential amino acids of needed by human body and various trace elements, serves not only as various food Nutritional supplement, also can be used as human body mine trace element, be various food nutritional supplement and protein sources.It is emulsification again Stabilizer, thickener have thickening power and the distinctive foaming characteristic of albumen and gas retaining well, and have good nutritive value. There is the effects of heat preservation, fresh-keeping, guarantor is fragrant, improves quality in the food industry.
Curcumin
Curcumin is a kind of polyphenol compound extracted from the rhizome of herbaceos perennial turmeric, traditional Curcumin is typically all to be used as food dye and additive, in recent years, a large amount of research shows that curcumin has extensive physiology Active function, such as it is reducing blood lipid, antitumor, anti-inflammatory, cholagogue, anti-oxidant.However, dissolubility pole of the curcumin in aqueous environments Difference, and it is unstable；In addition curcumin also has sensibility to light, heat, these factors all constrain curcumin in different necks significantly The application in domain.
Curcumin composite particles
Curcumin composite particles of the invention contain:
Component (a) curcumin；
Component (b) alcohol soluble protein；
It can on component (c) casein or its bromatology or in pharmaceutically acceptable salt or its bromatology or pharmaceutically connect The casein derived object received；
Wherein, component (a) curcumin and component (b) alcohol soluble protein are in admixture and by the components (c) it is wrapped up；
Also, the composite particles are hydrophilic particle.
In composite particles of the invention, in hydrophobic core, curcumin is uniformly to mix with alcohol soluble protein.
In the present invention, the shape of the curcumin composite particles is not particularly limited, and representative shape includes (but simultaneously It is not limited to): spherical, subsphaeroidal, oval.
" curcumin nanoparticles powder " is the curcumin nano particle after freeze-drying as used herein, it is preferable that the flavine The preparation method of nano particle is as described in Example 1, and the mass ratio of Zein and NaCas is 1.
Composition
As used herein, term " composition " includes pharmaceutical composition, Halth-care composition, dietary supplement compositions, drink Feed composition and food composition.
The beverage composition for treating dental erosion or food compositions include curcumin composite particles as described in the first aspect of the invention, and Acceptable carrier or additive in sitology.The composition can be formulated as typical food product known in the art, including Following form: powder, particle, tablet, pill, capsule, suspension, lotion, syrup, injection (infusion), liquid, extraction Object, chewing gum, tea, jelly or beverage.
Acceptable carrier or additive can be any carrier or additive known in the art in sitology.It is described to add Adding agent may include electrolyte, such as sodium salt (sodium chloride), sylvite (potassium citrate), calcium salt (calcium citrate), magnesium salts (magnesium sulfate) Deng.
The beverage composition for treating dental erosion also may include other components, and the other components can be various used in conventional beverage Flavoring agent or natural carbohydrate.The example of above-mentioned natural carbohydrate is conventional sugar, such as monosaccharide (such as glucose or fruit Sugar etc.), disaccharides (such as maltose, sucrose) and polysaccharide (such as glucan, cyclodextrin) and sugar alcohol, such as xylitol, sorbierite And antierythrite.Other flavoring agents can also be added, (such as thaumatin (taumatin), STEVIA REBAUDIANA mention natural flavouring Take object etc.) and synthetic flavorings (such as saccharin, Aspartame).It is preferably based on the beverage of 100mL, it is described natural Carbohydrate content is about 1 to 20g, preferably 5 to 12g.
Described pharmaceutical composition may include pharmaceutically acceptable carrier or additive.The pharmaceutical composition can pass through Conventional route (such as oral, rectum, intravenous injection, intramuscular, subcutaneous injection) is applied to mammal, including rat, mouse, family Poultry and people.So exemplary drug formulations known in the art can be made in pharmaceutical composition.Pharmaceutical composition can be made oral Preparation, injectable formulation, suppository, percutaneous preparation and through nasal preparation, but not limited to this.
After being configured to such preparation, pharmaceutically acceptable carrier needed for each preparation can be added or additive.It prepares After oral preparation, one in diluent, lubricating oil, binder, disintegrating agent, sweetener, stabilizer and preservative can be selected Kind is a variety of as carrier, can select one of flavoring agent, vitamin and antioxidant or a variety of as additive.
Carrier and additive can be any pharmaceutically acceptable example.In particular, it is preferred that diluent example It may include: lactose, glucose, sucrose, cornstarch, soya-bean oil, microcrystalline cellulose, sorbierite, xylitol and mannitol, preferably The example of lubricant may include: magnesium stearate and talcum, the example of preferred binder may include: polyvinylpyrrolidone Or hydroxypropyl cellulose.Additionally, it is preferred that the example of disintegrating agent may include: calcium carboxymethylcellulose, carboxyrnethyl starch sodium, poly- third Olefin(e) acid potassium or Crospovidone, the example of preferred sweetener may include: white sugar, fructose, sorbierite or Aspartame, preferably The example of stabilizer may include: sodium carboxymethylcellulose, beta-cyclodextrin, hundred beeswaxs and xanthan gum, the example of preferred preservative Son may include: methyl p-hydroxybenzoate, propylparaben and potassium sorbate.
In addition to these ingredients, it also may include for improving taste additives known, such as: natural flavouring, such as Lee Son, lemon, pineapple or medicinal herbs taste, fruit juice, natural dye, such as chlorophyllin or flavonoids, sweetener component, as fructose, Honey, sugar alcohol or sugar or acidulant such as citric acid or sodium citrate.
Main advantages of the present invention include:
(a) composite particles preparation method of the invention is simple, and low energy consumption.
(b) composite particles of the invention are coated with using the material from food, securely and reliably.
(c) composite particles property of the invention is stablized, and dissolubility is good.
(d) composite particles of the invention have the characteristic of control release.
(e) composite particles bioavilability of the invention is good.
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention Rather than it limits the scope of the invention.In the following examples, the experimental methods for specific conditions are not specified, usually according to conventional strip Part, or according to the normal condition proposed by manufacturer.Unless otherwise stated, otherwise percentage and number are calculated by weight.
Preparative Example 1
The preparation of alcohol soluble protein-casein sodium nanoparticle
Zeins is dissolved with 80% (v/v) ethanol water, wherein the mass concentration of zeins is 20mg/mL.A certain amount of above-mentioned alcohol solution is instilled into the caseinic acid sodium water solution that mass concentration is 2mg/mL, mixed system The mass ratio that feeds intake of middle zeins (Zein) and casein sodium (NaCas) be respectively 1:0.1,1:0.25,1:0.35, 1:0.5,1:0.625,1:0.8,1:1.0,1:1.25.Magnetic agitation for a period of time after, ethyl alcohol is dried up with nitrogen evaporator, obtains alcohol Molten albumen-casein sodium nanoparticle.
As a result as follows:
When the adding proportion of Zein and NaCas is 1:0.1~1:0.25, instantaneously there is macroscopic sediment deposition In bottom of bottle；As NaCas adding proportion increases to 1:0.35~1:0.5, milky dispersion can be formed, but will be above-mentioned After system stands a period of time, there have been one layer of white depositions for bottom of bottle；This may be due to NaCas additive amount not enough It is more, it is also not enough to stablize Zein particle；It, can shape when the adding proportion of NaCas is further increased to 1:0.625~1:1.25 At stable milky white color system, difference feeds intake mass ratio, and the partial size and polydispersity index of obtained nano particle are as shown in the table:
The size results measured from dynamic light scattering: when the ratio of Zein and NaCas are increased to 1 from 1:0.625: When 1, the increase on statistical significance is presented in particle size, and when the ratio of Zein and NaCas is further increased to 1:1.25, grain Diameter no longer increases, this may be since the NaCas of Zein particle surface absorption at this time has been saturated.Therefore, we select Zein The nano particle for being 1 with NaCas mass ratio is as the subsequent research system for containing curcumin.
Preparative Example 2
Alcohol soluble protein-casein sodium nanoparticle stability experiment
Alcohol soluble protein prepared by Preparative Example 1-casein sodium nanoparticle freeze-drying, and redissolved respectively in 2M NaCl aqueous solution and 40% (w/v) aqueous sucrose solution, the nanometer appearance after perspective Electronic Speculum observation redissolution.
The results are shown in Figure 10, and alcohol soluble protein-casein sodium nanoparticle of the redissolution in NaCl and aqueous sucrose solution is still So keep its spherical morphology in water.The nanoparticle surface redissolved in sucrose solution is smooth；And redissolve receiving in NaCl Grain of rice surface shows slightly unsmooth, some corner angle, this may be since drying process causes salt crystal to be deposited on nanoparticle in sample preparation Surface.
Embodiment 1
The preparation of curcumin nano system
Zeins and curcumin are dissolved with 80% (v/v) ethanol water, wherein the quality of zeins Concentration is 20mg/mL, and the mass concentration of curcumin is 1mg/mL.A certain amount of above-mentioned alcohol solution, which is instilled mass concentration, is The caseinic acid sodium water solution of 2mg/mL, the throwing of zeins (Zein) and casein sodium (NaCas) in mixed system Material mass ratio is 1:1.Magnetic agitation for a period of time after, ethyl alcohol is dried up with nitrogen evaporator, obtains the nanosystems for containing curcumin.
As a result as follows:
Fig. 1 shows that the curcumin nano particle that Zein and NaCas mass ratio are 1 redissolves digital photograph in water, Fig. 2 Show the transmission electron microscope picture of the curcumin nano particle.It can be seen from the figure that curcumin nano particle diameter of the invention In 180nm or so, granular size is more uniform, and shape is spherical in shape, and can see apparent hydrophobic core and hydrophilic shell moieties.
Fig. 3 show free curcumin compared with the DSC heat analysis for the curcumin being wrapped in nanometer system, it can be found that Curcumin is scattered in nanometer system with amorphous state.
Embodiment 2
The encapsulation rate of curcumin nano system
The preparation method of curcumin nano system is as described in Example 1.Fresh curcumin nanoparticles obtained are placed in- Pre-freeze is stayed overnight in 80 DEG C of ultra low temperature freezers, is then put into freeze dryer rapidly and 48h is lyophilized, obtain lyophilized powder sample.It weighs The free turmeric that the vortex washing of 2mL ethyl acetate is not wrapped in nanoparticle is added in curcumin nanoparticles powder after 4mg freeze-drying Then element is centrifuged 30min at 3900g, take out supernatant.With above-mentioned same method to the nanoparticle sediment after centrifugation again Secondary washing repeatedly for three times merges the supernatant after washing centrifugation.N2The supernatant being passed through after merging, blows ethyl acetate, then It is redissolved to obtain curcumin ethanol solution with 1mL ethyl alcohol.Using established curcumin UPLC analysis method, free ginger is calculated The quality of flavine, and nanoparticle system is calculated to the encapsulation rate of curcumin by following formula:
As a result as follows:
Nanoparticle system can achieve 95% or so to the encapsulation rate of curcumin, show that nanometer system may be implemented to turmeric The efficient encapsulating of element carries, and is more advantageous to the water solubility for improving curcumin.
Embodiment 3
The extracorporeal releasing experiment of curcumin nano system
Configure three kinds of dissolution mediums: simulation simulated gastric fluid, simulation artificial intestinal fluid and the artificial colonic fluid of simulation.Wherein, mould Quasi- simulated gastric fluid: by 2g sodium chloride, 7mL concentrated hydrochloric acid is with distilled water constant volume to 1000mL, and adjusting pH is 1.2；Simulation is artificial small Intestinal juice: 6.8g KH is weighed2PO4 is dissolved in 250mL distilled water, and NaOH the and 400mL distilled water of 190mL 0.2mol/L is added, and mixes With distilled water constant volume to 1000mL after even, with 0.2mol/L NaOH tune pH to 7.4；Simulate artificial colonic fluid: configuration concentration is The KH of 0.05mol/L2PO4 solution, and pH is adjusted to 6.0.Since the solubility of curcumin in water is very low, in order to meet bakie Condition all joined a certain amount of tween in above-mentioned three kinds of dissolution mediums, and it is artificial to be configured to the simulation containing 1% (w/v) tween Gastric juice, artificial intestinal fluid and artificial colonic fluid.
The release in vitro behavior of curcumin is studied using dynamic dialysis method.Weigh 20.5mg curcumin nanoparticles powder End is dispersed with the simulated gastric fluid of pH1.2, is placed in the bag filter pre-processed (molecular cut off 15kDa), and is placed on It is that extracorporeal releasing experiment is carried out in 37 DEG C, the shaking table of 100rpm in the conical flask of dissolution medium equipped with 60mL simulated gastric fluid.2h Bag filter is taken out afterwards, being put into is equally to be placed in shaking table and carry out in the conical flask of dissolution medium equipped with 60mL artificial intestinal fluid Release.Bag filter is taken out again after 6h, being put into is then to discharge in the conical flask of dissolution medium equipped with the artificial colonic fluid of 60mL Terminate release experiment after 16h.It is sampled in conical flask respectively at different time points, and fills into isometric Isothermal release in time and be situated between Matter draws ginger according to the amount for measuring curcumin in each time point dissolution medium under established curcumin UPLC chromatographic condition Flavine cumulative release curve.
As a result as shown in figure 4, from cumulative release curve it can be seen that curcumin discharged from nanoparticle system have control Make the characteristic of release.By being fitted to release profiles, the behavior of curcumin release in vitro meets the side Higuchi as the result is shown Journey, the equation after fitting are Y=6.2272t1/2-0.5965(R2=0.9946), this illustrates that curcumin mainly passes through diffusion It is released from nanoparticle.
Embodiment 4
The stability experiment of curcumin nano system
A certain amount of curcumin powder is dissolved in ethyl alcohol water mixed system (50:50, v/v), it is 10 μ g/mL that concentration, which is made, Curcumin ethanolic aqueous system.According to the encapsulation rate value for the curcumin nano particle that embodiment 2 obtains, nano-granule freeze-dried powder is redissolved End obtains the Zein-NaCas nanoparticle water-borne dispersions with identical curcumin concentration.Above two system is respectively placed in It is irradiated under heating and 354nm ultraviolet wavelength in 180 DEG C of baking ovens, then in different heating time point (0,10,20,40,60min) With the percentage for remaining curcumin under light application time point (0,20,40,60,90,120min) in sampling and measuring system.
As a result as shown in Figure 5,6, the stability for the curcumin being wrapped in nanoparticle greatly improves, and adds under the conditions of 180 DEG C Hot 60min, can still keep 60% or more activity, and partial size and polydispersity index be without significant change, and in alcohol-water system Free curcumin heats 60min substantially completely loss of activity under the conditions of 180 DEG C.Fig. 7 shows heating 10min (A) and 60min (B) transmission electron microscope picture of curcumin nano system when.It can be seen from the figure that at high temperature heat, the size of nanoparticle, point Cloth and pattern nothing are substantially change.The light durability of curcumin nano system of the invention is as shown in figure 8, be wrapped in nanoparticle In curcumin the sensibility of ultraviolet light (254nm) is substantially reduced, ultraviolet light irradiate 60min, 90% or more work can be kept Property, ultraviolet light irradiates 120min, can still keep 50% or so activity, be much better than free curcumin.The above results show this hair Bright curcumin nano particle has fabulous stability, is adapted to the working processes such as food baking.
Embodiment 5
The rehydration of curcumin nano system is tested
The curcumin nanoparticles powder of freeze-drying is redissolved again in the distilled water of same volume, is vibrated with vortex oscillation instrument The state of system is stored at room temperature, observed after 2min, and is compared with the parameters of freshly prepared curcumin nano particle.
As a result as follows:
Particle diameter distribution situation such as Fig. 9 institute of freshly prepared curcumin nano particle and the curcumin nanoparticles of freeze-drying rehydration Show, characterizing part data are as shown in the table, and the partial size, polydispersity index and surface potential of the two have no significant difference.Knot Fruit shows that curcumin nano particle of the invention has good freeze-drying rehydration.
Embodiment 6
The solubility experiment of curcumin nano system
A certain amount of curcumin nanoparticles powder is redissolved in distilled water, the curcumin nano obtained according to embodiment 2 The encapsulation rate value of the particle and concentration of nanoparticle calculates the solubility of curcumin nano particle after redissolving.
The solubility of curcumin nano particle of the invention can achieve 0.1-0.5mg/mL, be much higher than trip reported in the literature Water solubility 11ng/mL from curcumin.Increasing substantially for curcumin solubility is conducive to improve its bioavilability.
Embodiment 7
The experiment of cellular uptake rate
By Caco-2 cell inoculation in 96 hole blackboards, cell concentration is 2 × 105A/hole, in 37 DEG C, 5%CO2In incubator Culture 21-29 days, forms it into cell monolayer, and keep changing a not good liquor in every two days.It first carries out changing liquid before test, then add respectively Enter the free curcumin solution and curcumin nano system of same dose, culture 4h, for 24 hours, after 48h, 72h, 4 DEG C of blank are added PBS solution terminates cellular uptake.Cell monolayer is rinsed 3 times, addition cell pyrolysis liquid (0.5%Triton X-100, 0.2M NaOH) effect 3min, surveys fluorescence intensity at 425nm, 518nm wavelength.In addition, every hole takes 20 μ L BCA Quantitative Westerns Matter content, cell indicate the uptake ratio of two kinds of curcumins with fluorescence intensity with corresponding protein content ratio.
As a result as shown in figure 11, for 4 time points of test, Caco-2 cell is to the curcumin being wrapped in nanoparticle All have higher uptake ratio.
Embodiment 8
Cell transmembrane transport experiment
Caco-2 cell is taken to digest through 0.25% pancreatin, cell count is 6 × 105A/mL is added on 12 hole transwell training It supports and is cultivated in plate.Culture plate upper chamber (apical, AP) first infiltrates 2min with 0.1mL complete medium, and it is thin that 0.5mL is then added Born of the same parents, 1.5mL complete medium is added in lower room (basolateral, BL), in 37 DEG C, 5%CO2It is cultivated in incubator, after 6-16h It carries out changing liquid, removes not attached cell, change a not good liquor within every two days later.1h carries out changing liquid before transport experiment starts, and then surveys Cross-film resistance is determined, when resistance is 600-800 Ω/cm2When start formally to test.There to be same dose (25 μM) respectively The free curcumin solution of 0.5mL and curcumin nano system are added to upper chamber as supply pool, and the complete of 1.5mL is added with room at present Culture medium is as reception tank, and every group sets 3 repetitions, in 37 DEG C, 5%CO2It is cultivated in incubator, respectively in 1,2,3,4h, from Lower room takes 50 μ L in 96 orifice plates, in triplicate, while adding 37 DEG C of complete mediums, 150 μ L, in exciting light 425nm, transmitting Fluorescence intensity is surveyed under light 518nm wavelength, and curcumin is calculated in the bioavilability of cellular level by following formula.
As a result as shown in Figure 12 and following table, the curcumin being wrapped in nanoparticle all has the life on higher cellular level Object availability.
All references mentioned in the present invention is incorporated herein by reference, independent just as each document It is incorporated as with reference to such.In addition, it should also be understood that, after reading the above teachings of the present invention, those skilled in the art can To make various changes or modifications to the present invention, such equivalent forms equally fall within model defined by the application the appended claims It encloses.

Claims (29)

1. a kind of curcumin composite particles, which is characterized in that the composite particles contain:
Component (a): curcumin；
Component (b): alcohol soluble protein；
Component (c): on casein or bromatology or pharmaceutically acceptable caseinate；
Wherein, component (a) curcumin and component (b) alcohol soluble protein are in admixture and by the components (c) It is wrapped up；
Also, the composite particles are hydrophilic particle；
Also, the component (b) is 90-98% to the clad ratio of component (a)；
Also, the mass ratio of the component (b) and component (c) is 1:(0.625~1.25)；
Also, the mass ratio of the component (a) and component (b) is (1-2): (10-20)；
Also, it after the first solution during the preparation process, is added dropwise to the second solution, is stirred, so that the turmeric be made Plain composite particles；
Wherein, first solution includes the first solvent and component (a) curcumin and component (b) alcohol that are dissolved in the first solvent Molten albumen, and second solution includes the second solvent and the component (c) being dissolved in the second solvent.
2. composite particles as described in claim 1, which is characterized in that the curcumin composite particles have nucleocapsid structure.
3. composite particles as claimed in claim 2, which is characterized in that the nucleocapsid structure has hydrophobic core and hydrophilic outer Shell.
4. composite particles as described in claim 1, which is characterized in that the component (b) is 1 with component (c) mass ratio: (0.8-1.25)。
5. composite particles as described in claim 1, which is characterized in that the partial size of the curcumin composite particles is 120- 300nm。
6. composite particles as claimed in claim 3, which is characterized in that the hydrophilic outer shell with a thickness of 20-150nm.
7. composite particles as claimed in claim 6, which is characterized in that the hydrophilic outer shell with a thickness of 60-80nm.
8. composite particles as described in claim 1, which is characterized in that the alcohol soluble protein includes zeins, small Gliadin.
9. composite particles as described in claim 1, which is characterized in that the component (c) is caseinate, and described Caseinate be casein sodium, Caseins, potassium salts, calcium caseinate, or combinations thereof.
10. composite particles as described in claim 1, which is characterized in that the curcumin composite particles, which have, to be selected from the group One or more features:
(i) bioavilability: bioavilability 50-80%；
(ii) dissolubility: in water, solubility is 0.1-1mg/mL at 25 DEG C.
11. composite particles as claimed in claim 10, which is characterized in that the bioavilability is 55-70%.
12. composite particles as claimed in claim 10, which is characterized in that the solubility is 0.1-0.5mg/mL.
13. a kind of composition, which is characterized in that the composition includes (a) curcumin composite particles described in claim 1； (b) acceptable carrier in pharmaceutically acceptable carrier or bromatology.
14. composition as claimed in claim 13, which is characterized in that contain the turmeric of 0.001-99wt% in the composition Plain composite particles, are based on the total weight of the composition.
15. a kind of beverage composition for treating dental erosion, which is characterized in that the composition includes compound of (a) curcumin described in claim 1 Grain；(b) the upper acceptable carrier of beverage.
16. beverage composition for treating dental erosion as claimed in claim 15, which is characterized in that the beverage composition for treating dental erosion also includes can on food The additive of receiving.
17. beverage composition for treating dental erosion as claimed in claim 16, which is characterized in that the additive includes: sweetener, acidity adjustment Agent, electrolyte, and/or essence.
18. beverage composition for treating dental erosion as claimed in claim 15, which is characterized in that also include beverage in the beverage composition for treating dental erosion Matrix is as carrier acceptable on food.
19. beverage composition for treating dental erosion as claimed in claim 18, which is characterized in that the beverage base includes coffee, tea, fruit Juice, milk, milk replacer, dairy products, and/or water.
20. a kind of method for preparing composite particles described in claim 1, which is characterized in that the method includes the steps:
(i) the first solution and the second solution are provided, wherein
First solution includes the first solvent and component (a) curcumin and the molten egg of component (b) alcohol that are dissolved in the first solvent It is white；
Second solution includes the second solvent and the component (c) being dissolved in the second solvent；
(ii) the first solution is mixed with the second solution, to form the curcumin composite particles of claim 1；
In step (ii), after the first solution is added dropwise to the second solution, it is stirred.
21. method as claimed in claim 20, which is characterized in that the method further comprises the steps of:
(iii) it to the curcumin composite particles formed in previous step, is separated；
(iv) it optionally carries out that the curcumin composite particles of previous step are dried.
22. method as claimed in claim 20, which is characterized in that the mass concentration of alcohol soluble protein is 5- in first solution 50mg/mL。
23. method as claimed in claim 22, which is characterized in that the mass concentration of alcohol soluble protein is in first solution 15-25mg/mL。
24. method as claimed in claim 20, which is characterized in that the mass concentration of curcumin is 0.1- in first solution 10mg/mL。
25. method as claimed in claim 24, which is characterized in that the mass concentration of curcumin is 0.5- in first solution 5mg/mL。
26. method as claimed in claim 20, which is characterized in that the mass concentration of caseinate is in second solution 1-10mg/mL。
27. method as claimed in claim 20, which is characterized in that the use volume of first solution and second solution Than for 1-5:10-50.
28. the purposes of composite particles as described in claim 1, which is characterized in that be used to prepare a composition, the composition For reducing blood lipid, antitumor, anti-inflammatory, cholagogue, and/or anti-oxidant.
29. purposes as claimed in claim 28, which is characterized in that the composition includes food compositions, pharmaceutical composition Object, Halth-care composition.
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