CN114098076B - Preparation method of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles - Google Patents
Preparation method of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles Download PDFInfo
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- CN114098076B CN114098076B CN202111370893.5A CN202111370893A CN114098076B CN 114098076 B CN114098076 B CN 114098076B CN 202111370893 A CN202111370893 A CN 202111370893A CN 114098076 B CN114098076 B CN 114098076B
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- zein
- quercetin
- pectin
- chitosan
- nanoparticles
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- Cosmetics (AREA)
Abstract
The invention discloses a preparation method of genipin-crosslinked quercetin-zein/pectin/chitosan nano-particles, which belongs to the technical field of food. In the composite nano-particles prepared by the invention, the bioavailability of the quercetin is improved from 16.1% to 82.7%, and the nano-particles can keep good stability after being stored for 15 days at 4 ℃.
Description
Technical Field
The invention belongs to the technical field of food science and food additives, and particularly relates to a preparation method of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles.
Background
Quercetin is a polyhydroxy flavonoid compound, and has the outstanding characteristic of strong oxidation resistance. In addition, quercetin also has physiological functions of diminishing inflammation, resisting oxidation, preventing cancer, resisting allergy, etc. However, quercetin is insoluble in water and oil, unstable to external environmental factors such as light and heat, and easily decomposed under alkaline conditions, which greatly limits its application in functional foods. Quercetin and zein can be dissolved in high-concentration ethanol together, and quercetin can be loaded into zein nanoparticles by an anti-solvent precipitation method. The principle is that zein and quercetin are dissolved in ethanol water solution with a certain concentration and then are uniformly dispersed in the water phase, and as the ethanol concentration is rapidly reduced, zein is supersaturated to form particles, and meanwhile, the quercetin is embedded in a hydrophobic inner core of zein nano particles. But the zein nano particles have the problems of low stability, low embedding rate and the like. In the prior art, a biopolymer coating is usually used to solve the above problems, for example, a single sodium caseinate and pectin are used as a stabilizer of zein nanoparticles, so that the embedding rate of zein on functional factors is improved to a certain extent, but there are few studies on stabilizing zein nanoparticles by using two different polysaccharides, and the prior art has a problem of large particle size.
The layer-by-layer electrostatic accumulation method is also called a layer-by-layer self-assembly method, and can be used for preparing multilayer nanoparticles. The principle is that polyelectrolytes with opposite charges can form multilayer nanoparticles through electrostatic interaction, and compared with nanoparticles formed by hydrogen bonds or hydrophobic interaction self-assembly, the polyelectrolyte combined through electrostatic interaction has stronger acting force. At present, the preparation of zein nanoparticles with two different polysaccharides and stable simultaneously by combining an anti-solvent precipitation method and a layer-by-layer electrostatic accumulation method is rarely reported. In addition, researches show that the mechanical properties of protein and polysaccharide complex nanoparticles can be effectively improved by crosslinking, but although the crosslinking effect of common chemical crosslinking agents such as glutaraldehyde is good, the cytotoxicity of the artificially synthesized chemical crosslinking agents is high, and the pH and the temperature of the glutamine transaminase are strictly limited due to the crosslinking performance of the glutamine transaminase, so that the application of the glutamine transaminase in a food system is limited. Therefore, a safe and efficient cross-linking agent is required to improve the stability of the protein and polysaccharide nanoparticles loaded with the functional factors.
Disclosure of Invention
[ problem ] to
Aiming at the defects of instability, low quercetin embedding rate and low quercetin bioavailability of the existing zein nanoparticles, the invention provides a method for efficiently preparing genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles by combining an anti-solvent precipitation method and a layer-by-layer electrostatic accumulation method. The technical scheme provided by the invention has the advantages of simple method, safe operation, green solvent and easy popularization.
[ technical conception ]
According to the invention, an anti-solvent method is combined with a layer-by-layer electrostatic deposition method, pectin and chitosan are used as raw materials and are attached to the surface of zein nanoparticles through an electrostatic deposition method to prepare ternary nanoparticles, so that the physical stability of the zein nanoparticles and the embedding rate of quercetin are improved; and genipin is added for crosslinking so as to further improve the stability and bioavailability of the nano-particles.
The technical principle of the invention is as follows:
zein is dissolved in ethanol water solution with a certain concentration, contains a large amount of hydrophobic amino acid, and has obvious partition of hydrophilic part and hydrophobic part in the structure, so the zein has unique self-assembly characteristic, and can be prepared into nano particles by an anti-solvent method and used for encapsulating hydrophobic substances. Pectin is an anionic polysaccharide, and is adsorbed on the surface of zein nanoparticles through electrostatic interaction to obtain negatively charged zein/pectin nanoparticles. The chitosan is the only cationic polysaccharide in nature, has no toxicity, no irritation and good biocompatibility, is an excellent carrier material, and can be adsorbed to the surface of zein/pectin nanoparticles through electrostatic interaction to obtain the zein/pectin/chitosan nanoparticles with positive electricity. Genipin is a natural chemical cross-linking agent derived from gardenia fruits, is not limited by pH, has toxicity which is 5000-10000 times lower than that of other cross-linking agents, and is prepared into genipin cross-linked quercetin-zein/pectin/chitosan nano particles by utilizing the property that a plurality of active groups such as hydroxyl groups, ester groups and the like of genipin can have cross-linking reaction with zein and chitosan.
The invention aims to provide a method for preparing genipin cross-linked zein/pectin/chitosan nanoparticles, and the prepared nanoparticles are applied to embedding and delivering quercetin.
The purpose of the invention is realized by the following technical scheme:
the first aspect of the invention provides a method for preparing genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles, which sequentially comprises the following steps:
(1) Dissolving quercetin and zein in an ethanol-water solution, and preparing the quercetin-zein nanoparticle alcohol-water solution by an anti-solvent precipitation method;
(2) Injecting the quercetin-zein nanoparticle alcohol-water solution obtained in the step (1) into a pectin solution with the pH value of 3.0-5.0, removing ethanol in the system by rotary evaporation, and supplementing distilled water with the same volume as the lost ethanol to obtain a quercetin-zein/pectin nanoparticle water solution;
(3) Injecting the quercetin-zein/pectin nano-particle aqueous solution obtained in the step (2) into a chitosan solution with the pH value of 3.0-5.0 to obtain a quercetin-zein/pectin/chitosan nano-particle aqueous solution;
(4) And (4) injecting a genipin aqueous solution into the quercetin-zein/pectin/chitosan nanoparticle aqueous solution obtained in the step (3), mixing, reacting, freezing and drying to obtain genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles.
As an embodiment of the present invention, step (1) specifically is: dissolving quercetin and zein in an ethanol-water solution to form a uniform solution with the concentration of the zein of 10 mg/mL-20 mg/mL and the concentration of the quercetin of 0.5 mg/mL-1.3 mg/mL; adding distilled water with pH of 3.0-5.0 under stirring to obtain quercetin-zein nanoparticle alcohol-water solution.
According to one embodiment of the invention, the mass ratio of quercetin to zein is 1.
As an embodiment of the present invention, the ratio of zein: the total mass ratio of pectin to chitosan is 5:3.
As an embodiment of the present invention, the molecular weight of the chitosan in the step (3) is 10 to 60 ten thousand. Preferably, the molecular weight of chitosan is 20 to 30 ten thousand. Further preferably, the chitosan has a molecular weight of 30 ten thousand.
As an embodiment of the present invention, in the step (4), the conditions of the reaction are mixed: stirring and crosslinking for 4-16 hours at 25-45 ℃.
In one embodiment of the present invention, the mass ratio of genipin to zein is 1 (50-400).
As an embodiment of the present invention, in the step (4), the conditions of freeze-drying: the drying temperature is-80 ℃, and the drying time is 24-96 h.
As an embodiment of the present invention, the nanoparticles in the steps (1) to (4) are formed at a rotation speed of 600 to 900 rpm.
In an embodiment of the present invention, the method specifically includes the following steps:
step 1: weighing 1g zein powder and 50mg quercetin in 100mL 80% ethanol to obtain quercetin-zein alcohol-water solution; weighing 0.1g of pectin in 100mL of ultrapure water to obtain a pectin solution; weighing 0.1g of chitosan in 100mL of 1% acetic acid aqueous solution to obtain a chitosan solution;
step 2: adjusting the pH values of the pectin solution and the chitosan solution to 4.0 by using 1M sodium hydroxide solution;
and 3, step 3: dripping 10mL of the quercetin-zein alcohol-water solution into 30mL of distilled water with the pH value of 4.0, and stirring to form quercetin-zein nanoparticles;
and 4, step 4: uniformly mixing the mixed system obtained in the step 3 with 30mL of pectin solution, removing ethanol by rotary evaporation, and complementing the volume with distilled water to obtain quercetin-zein/pectin nano-particles;
and 5: dissolving and uniformly mixing the mixed system obtained in the step 4 with 30mL of chitosan to obtain quercetin-zein/pectin/chitosan nanoparticles;
step 6: and (3) uniformly mixing the genipin aqueous solution with the mixed system obtained in the step (5), crosslinking for 4 hours at 25 ℃, and freeze-drying to obtain the genipin crosslinked quercetin-zein/pectin/chitosan nano-particles.
In one embodiment of the invention, the zein has a purity of 99.8%.
In one embodiment of the present invention, the quercetin is 90% pure.
The second aspect of the invention is to provide genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles prepared by the method.
The third aspect of the invention is to provide the application of the genipin-crosslinked quercetin-zein/pectin/chitosan nano-particles in the preparation of functional foods, health-care products and medicines.
[ advantageous effects ]:
(1) The invention provides genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles, which are prepared by successfully embedding quercetin by using zein as a wall material through an anti-solvent precipitation method, sequentially adding pectin and chitosan components, sequentially adsorbing the components on the surfaces of the zein nanoparticles through electrostatic interaction to obtain the quercetin-zein/pectin/chitosan nanoparticles, and adding a genipin aqueous solution for cross-linking to obtain the genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles. The finally prepared nano particles have the particle size of 250-350nm, the PDI of 0.20-0.28, the zeta-potential of +35-50mV, small particle size, uniform system and strong electrification.
(2) The invention utilizes the pectin and chitosan composite coating and genipin cross-linking to synergistically improve the embedding rate and bioavailability of quercetin: through determination, the embedding rate of the quercetin-zein/pectin nanoparticles, the quercetin-zein/pectin/chitosan nanoparticles and the genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles to quercetin is 73.3%, 86.6% and 92.2% in sequence. Through determination, the bioavailability of quercetin in free quercetin, quercetin-zein/pectin nanoparticles, quercetin-zein/chitosan nanoparticles, quercetin-zein/pectin/chitosan nanoparticles and genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles is 16.1%, 55.1%, 63.3%, 72.6% and 82.7% in sequence, and the genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles disclosed by the invention are proved to overcome the defects of low embedding rate and low bioavailability of quercetin in the prior art.
(3) The genipin cross-linked quercetin-zein/pectin/chitosan nano-particles provided by the invention have good stability, and the retention rate of quercetin is up to more than 85% after the genipin cross-linked quercetin-zein/pectin/chitosan nano-particles are stored for 15 days at 4 ℃.
(4) The oxidation resistance of the genipin cross-linked quercetin-zein/pectin/chitosan nano-particles provided by the invention is obviously improved: through determination, DPPH and clearance rates of the free quercetin, the quercetin-zein/pectin/chitosan nanoparticles and the genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles are 84.5%, 88% and 92.5% in sequence, and ABTS + free radical clearance rates are 45.7%, 46.3% and 52.4% in sequence.
(5) The preparation method of the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle provided by the invention is characterized in that the method combining anti-solvent precipitation and layer-by-layer electrostatic accumulation is used for preparing the quercetin-zein/pectin/chitosan nanoparticle, and genipin crosslinking is added (the genipin crosslinking reaction condition is mild, and no limitation is imposed on pH value) to finally prepare the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle. In the published invention CN 112205628A, zein is positively charged below the isoelectric point, chitosan is also positively charged as cationic polysaccharide, and the interaction force between the zein and the chitosan is mainly hydrophobic interaction and hydrogen bond, so that the zein is weak in acting force, unstable and low in repeatability. According to the invention, the zein nanoparticles are firstly combined with pectin to form negatively charged nanoparticles, and then combined with positively charged chitosan through electrostatic interaction, so that the interaction force is stronger. Compared with the existing technology for preparing nano particles which can involve high-speed dispersion, has higher cost and introduces toxic and harmful organic reagents, micromolecular surfactants and other defects, the technology provided by the invention is simple, convenient and controllable, has good repeatability, uses green solvents (water and ethanol), is convenient to implement, is easy to popularize and has good application prospect.
Drawings
FIG. 1 is a Fourier infrared spectrum of genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs GNPs) of example 1 of the present invention, quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs NPs) of comparative example 1, and quercetin, zein, pectin, chitosan.
FIG. 2 is an X-ray diffraction pattern of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs GNPs) of example 1 of the present invention, quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs NPs) of comparative example 1, zein/pectin/chitosan nanoparticles (zein-pec-cs NPs) of comparative example 4, and quercetin.
FIG. 3 is a TGA plot of genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles of example 1 of the present invention (que-zein-pec-cs GNPs), quercetin-zein/pectin nanoparticles of comparative example 2 (que-zein-pec NPs), and quercetin-zein/pectin/chitosan nanoparticles of comparative example 1 (que-zein-pec-cs NPs).
Fig. 4 is a graph comparing the embedding rates of quercetin-zein/pectin/chitosan nanoparticles of comparative example 2 (que-zein-pec NPs), quercetin-zein/pectin/chitosan nanoparticles of comparative example 1, and genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 with different degrees of crosslinking (in the graph, 50.
FIG. 5 shows the results of the thermal stability test of the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 of the present invention, wherein the thermal treatment condition is 80 ℃ for 0-60min, and the test indexes are particle size (A), potential (B) and PDI (C).
FIG. 6 is the quercetin-zein/pectin nanoparticles of comparative example 2 of the present invention (que-zein-pec NPs), quercetin-zein/pectin/chitosan nanoparticles of comparative example 1 (que-zein-pec-cs NPs), genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles of example 1 (que-zein-pec-cs GNPs), quercetin-zein/chitosan nanoparticles of comparative example 3 (que-zein-cs NPs), and quercetin bioavailability in free quercetin.
FIG. 7 is a graph showing the ionic strength stability of comparative example 1 quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs NPs), comparative example 2 quercetin-zein/pectin nanoparticles (que-zein-pec NPs), and example 1 genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs GNPs) of the present invention.
Fig. 8 is a graph showing DPPH-free radical scavenging rate of the quercetin-zein/pectin/chitosan nanoparticle of comparative example 1 and the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle of example 1 and free quercetin (50, 100, 200.
Fig. 9 is ABTS free radical scavenging ratio of the quercetin-zein/pectin/chitosan nanoparticles of comparative example 1 and the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 and free quercetin of the present invention (50.
Fig. 10 is a graph showing the storage stability of quercetin-zein/pectin/chitosan nanoparticles and genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles stored at 4 ℃ for 15 days in the practice of the present invention, with the test indices of particle size (a), PDI (B), embedding rate (C), and potential (D) (in the figure, 1.
Detailed Description
The following detailed description of embodiments of the invention is made with reference to the accompanying drawings and examples. But not limiting the invention in any way and any variations or modifications based on the teachings of the invention are within the scope of the invention.
Example 1
Preparation of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles:
(1) Weighing 1g of zein powder and 50mg of quercetin in 100mL of 80% ethanol, and dissolving and uniformly mixing to obtain a quercetin-zein ethanol solution;
weighing 0.1g of pectin in 100mL of ultrapure water, and dissolving and uniformly mixing to obtain a pectin solution;
weighing 0.1g of chitosan, dissolving and uniformly mixing in 100mL of 1% acetic acid aqueous solution to obtain a chitosan solution;
(2) The pH values of the pectin solution and the chitosan solution are adjusted to 3.0-5.0 by using 1M sodium hydroxide solution.
(3) Dripping 10mL of the quercetin-zein ethanol solution obtained in the step (1) into 30mL of distilled water with the pH value of 3.0-5.0, and magnetically stirring to form quercetin-zein nanoparticles;
(4) And (4) dripping the mixed system obtained in the step (3) into 30mL of the pectin solution, uniformly stirring, performing rotary evaporation to remove ethanol, and complementing the volume of the ethanol with distilled water to obtain the quercetin-zein/pectin nano-particles.
(5) And (4) dripping the mixed system obtained in the step (4) into 30mL of the chitosan solution, and uniformly stirring to obtain the quercetin-zein/pectin/chitosan nano-particles.
(6) And (3) adding 50-200 mu L of 5mg/mL genipin aqueous solution into the mixed system obtained in the step (5), magnetically stirring for 4-16h at 25 ℃, and freeze-drying (the drying temperature is-80 ℃ and the drying time is 24-96 h) to obtain genipin cross-linked quercetin-zein/pectin/chitosan nano-particles with different cross-linking degrees.
Wherein, the genipin cross-linked quercetin-zein/pectin/chitosan nano-particles with the genipin-zein mass ratio of 1.
Comparative example 1
Preparing quercetin-zein/pectin/chitosan nanoparticles: the preparation procedure was the same as in steps (1) to (5) of example 1.
Comparative example 2
Preparing quercetin-zein/pectin nanoparticles: the preparation procedure was the same as in steps (1) to (4) of example 1, wherein the volume of the pectin solution in step (4) was changed to 60mL.
Comparative example 3
Preparing quercetin-zein/chitosan nanoparticles:
(1) Weighing 1g of zein powder and 50mg of quercetin in 100mL of 80% ethanol, and dissolving and uniformly mixing to obtain a quercetin-zein ethanol solution;
weighing 0.1g of chitosan, dissolving and uniformly mixing in 100mL of 1% acetic acid aqueous solution to obtain a chitosan solution;
(2) Adding the chitosan solution into the quercetin-zein ethanol solution, performing rotary evaporation to remove ethanol, and adjusting pH to 4.0 to obtain quercetin-zein/chitosan nanoparticles.
Comparative example 4
Preparing zein/pectin/chitosan nanoparticles: the preparation procedure was the same as in the steps (1) to (5) of example 1, except that quercetin was not added.
Comparative example 5
The quercetin microcapsule prepared in L-ascorbic acid-quercetin complex coacervation double-embedding microencapsulation research of Master academic thesis of Jiangnan university has the bioavailability of 73.31% under the same simulated digestion condition, but the invention reaches 82.7%, and the bioavailability of the quercetin is greatly improved.
Example 2 characterization of properties
Properties of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 were analyzed using fourier infrared spectroscopy, X-ray diffraction and thermogravimetric analysis, taking a genipin to zein mass ratio of 1 to 100 as an example, and the test results are shown in fig. 1, 2 and 3.
The fourier-ir spectrum of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 is shown in fig. 1: as can be seen from FIG. 1, the absorption peak of the phenolic hydroxyl group of quercetin appeared at 3395cm-1。1612、1513cm-1Due to stretching vibration of the benzene ring. Zein in amide A band (3306 cm)-1) Amide I band (1654 cm)-1) Amide II band (1546 cm)-1) And amide III band (1453 cm)-1) Has a characteristic peak at the absorption position, wherein 3306cm-1The characteristic peak is mainly due to the superposition of N-H stretching vibration and O-H stretching vibration, while the characteristic peaks at the amide I band and the amide II band are respectively due to the stretching of carbonyl C = O and C-N stretching vibration and N-H bending vibration, and the amide III band represents-NH3 +A group. Pectin and chitosan are polysaccharides, and they are 3300cm-1The maximum characteristic peak is nearby. Fruit of Chinese angelicaThe peak value of-OH group is from 3389cm when the glue and chitosan are adsorbed on zein nanoparticles-1(pectin) and 3360cm-1(Chitosan) to 3303cm-1(que-zein-pec-cs GNPs), which indicates that hydrogen bonds exist between pectin, chitosan and zein. Comparing infrared spectrograms of genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs GNPs) and quercetin, the infrared spectrograms show that characteristic peaks of quercetin are almost transferred and the intensity of the characteristic peaks is reduced, and the result shows that quercetin is successfully wrapped in a hydrophobic core of the nanoparticles. Wherein quercetin is at 3395cm-1The hydroxyl absorption band of (a) was completely masked, indicating that hydrogen bonding may exist between quercetin and zein.
The X-ray diffraction pattern of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 is shown in fig. 2: many peaks exist in the X-ray diffraction pattern of quercetin, which indicates that quercetin has a certain crystal structure and exists in a crystalline state. The X-ray diffraction patterns of the quercetin-zein/pectin/chitosan nanoparticles, the genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles and the genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles without embedded quercetin are wide diffraction peaks, and the quercetin molecules are seen to be changed from an ordered crystalline state to a disordered amorphous state, so that the compound effect of the quercetin and the zein is proved, and the quercetin is successfully embedded into the zein nanoparticles.
The thermogravimetric analysis curve of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 is shown in fig. 3: thermogravimetric analysis curves show the mass loss of the sample with temperature change, used to study the thermal degradation of the sample. As can be seen from fig. 3, compared to quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs NPs) and quercetin-zein/pectin nanoparticles (que-zein-pec NPs), genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs GNPs) have greatly reduced mass loss in the temperature range of wall material decomposition at 200-350 ℃, and the weight loss speed is relatively slow, which indicates that genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles have better thermal stability at 200-350 ℃, indicating that genipin crosslinking can improve the thermal degradation property of quercetin-zein/pectin/chitosan nanoparticles, so that genipin-crosslinked pectin-zein/chitosan nanoparticles have improved thermal processing performance.
EXAMPLE 2 encapsulation efficiency
Embedding rates of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles in example 1 of the present invention (genipin to zein mass ratio of 1. The specific determination method is as follows:
the method for measuring the embedding rate comprises the following steps: 10mL of the nanoparticle solution finally prepared in example 1 and comparative examples 1 and 2 (the addition amount of quercetin was 50. Mu.g/mL) was taken, 40mL of absolute ethanol was added, the mixture was subjected to ultrasonication for 40min and centrifugation at 3000rpm for 10min, and the supernatant was taken to measure the absorbance at 376 nm.
The embedding rate of the nanoparticles to be detected on the quercetin is calculated according to the following formula:
as can be seen from FIG. 4, the embedding rate of quercetin of nanoparticles (que-zein-pec-cs NPs) prepared by two-layer coating of zein nanoparticles with chitosan instead of part of pectin was increased from 73.3% to 86.1% compared to pectin alone (que-zein-pec NPs). And genipin is used as a cross-linking agent to prepare the quercetin-zein/pectin/chitosan nano-particles with different cross-linking degrees, the embedding rate can be further improved to 92.2% by adding genipin, a more compact surface structure is formed after cross-linking, and the quercetin-zein cross-linked chitosan nano-particles have a better interception effect.
Example 3 thermal stability
The genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle solution prepared in example 1 was heated to 80 ℃, held for 60min, sampled every 10min, and after cooling to room temperature, the particle size, particle size distribution (PDI) and zeta-potential of the nanoparticles were measured using a malvern multi-angle particle size and high sensitivity zeta-potential analyzer, the results of which are shown in fig. 5.
As can be seen from FIG. 5, the particle size and potential of the nanoparticles remained unchanged after heating at 80 ℃ for 60min, while PDI was slightly increased but was kept below 0.4 overall, and the system was still relatively uniform. The above results demonstrate that the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles prepared in example 1 have good thermal stability.
Example 4 bioavailability
The bioavailability of quercetin in genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs GNPs) of example 1 of the present invention, quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec NPs) of comparative example 1, quercetin-zein/pectin nanoparticles (que-zein-pec NPs) of comparative example 2, quercetin-zein/chitosan (que-zein-cs NPs) of comparative example 3, and quercetin in free quercetin were determined separately, as follows:
preparing simulated gastric fluid (2 mL concentrated hydrochloric acid, 0.5g sodium chloride, 0.8g pepsin and 250mL deionized water, adjusting the pH to 1.3 by using 1mol/L NaOH, and fixing the volume) and simulated intestinal fluid (3.4 g monopotassium phosphate, 95mL 0.2mol/L NaOH,2.0g trypsin and 2.0g deoxycholate, adjusting the pH to 7.0 by using 1mol/L NaOH, and fixing the volume).
10mL of the nanoparticle solution finally prepared in example 1 and comparative examples 1, 2 and 3 (the added amount of quercetin was 50. Mu.g/mL) was mixed with 10mL of simulated gastric fluid, and the mixture was continuously shaken in a 37 ℃ air bath shaker for 2 hours, and the pH of the mixture after completion of gastric simulated digestion was adjusted to 7.0 with 1mol/L NaOH. Then 5mL of simulated intestinal fluid was added to the mixture and shaken continuously in a 37 ℃ air bath shaker for 4h. After digestion, the mixture was centrifuged at 9000rpm for 30 minutes, the micelle layer was collected and the quercetin content in the micelle layer was determined.
The bioavailability of quercetin was calculated as follows:
C-Quercetin content in micelle layer;
C0-total quercetin addition.
The measurement results are shown in FIG. 6: the bioavailability of free quercetin is only 16.1%. After embedding, the bioavailability of quercetin is greatly improved. The bioavailability of quercetin in quercetin-zein/pectin nanoparticles (que-zein-pec NPs), quercetin-zein/chitosan nanoparticles (que-zein-cs NPs), and quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs NPs) was 55.1%, 63.3%, and 72.6%, respectively; after the quercetin-zein/pectin/chitosan nanoparticles are crosslinked by using genipin as a crosslinking agent (que-zein-pec-cs GNPs), the bioavailability of the quercetin is further improved to 82.7 percent.
The experimental results show that: free quercetin is unstable in the gastrointestinal environment and is easily degraded. On one hand, the zein/pectin/chitosan shell can be used as a physical barrier, so that the degradation rate of quercetin in a gastric juice environment is effectively reduced; on the other hand, the pectin and chitosan solution is acidic, so that the hydrolysis of zein by pepsin can be delayed; in a third aspect, the bioavailability of quercetin (up to 82.7%) is further improved by crosslinking genipin, probably because the crosslinked nanoparticles form a more compact structure, the structural integrity can be better maintained in a gastric juice environment; in the fourth aspect, quercetin changes its existing state from a crystalline state to an amorphous state, and is more easily digested and absorbed, showing an increase in bioavailability.
Example 5 Ionic Strength stability
To the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle solution (que-zein-pec-cs GNPs) and the quercetin-zein/pectin/chitosan nanoparticle solution (que-zein-pec-cs NPs) prepared in example 1, sodium chloride solutions were added so that the sodium chloride concentrations were 10, 20, 30, 50, 100mmol/L, and the particle diameters were measured after standing for 10 min. The results are shown in FIG. 7.
As can be seen from fig. 7, the ionic strength stability of the quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs NPs) is higher than that of the nanoparticles of the pectin coating alone (que-zein-pec NPs), and the quercetin-zein/pectin nanoparticle solution (que-zein-pec NPs) protein nanoparticles can generate granular precipitates when the ionic strength reaches 50mM, so that the particle size cannot be determined.
Compared with a quercetin-zein/pectin/chitosan nanoparticle solution (que-zein-pec-cs NPs), the particle size of the crosslinked nanoparticles is increased to be smaller along with the increase of the ion concentration under the concentration of 10-100mM NaCl under the genipin crosslinked quercetin-zein/pectin/chitosan nanoparticles (que-zein-pec-cs GNPs). Thus, the ionic strength stability of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle solution is improved compared with that of uncrosslinked nanoparticles.
EXAMPLE 6 Oxidation resistance
The following specific test methods were performed for the oxidation resistance (DPPH-radical scavenging rate, ABTS-radical scavenging rate) of the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles of example 1 of the present invention (50, 1, 200, 1, 400 in the figure:
DPPH free radical scavenging Rate test
1mL of the nanoparticle solution finally prepared in example 1 and an aqueous solution of quercetin ethanol (the amount of quercetin added was 50. Mu.g/mL) were added to the mixture, 4.0mL of a 0.1mmol/L DPPH solution was added thereto, the mixture was mixed, the mixture was left in the dark for 30 minutes, and A was measured at 517nm using 80% ethanol as a reference solutions. Measurement of A by Using distilled Water instead of sample0By usingAc was measured by ethanol instead of DPPH.solution. DPPH.radical scavenging ratio was calculated by the formula (1).
A0-absorbance measured without the addition of sample;
Ac-absorbance measured when DPPH solution is replaced by ethanol;
As-absorbance measured when antioxidant is added.
ABTS free radical scavenging test
0.1mL of 10mL of the nanoparticle solution finally prepared in example 1 and an aqueous solution of quercetin ethanol (the added amount of quercetin was 50. Mu.g/mL) were taken and mixed with 3.8mL of ABTS solution (absorbance value was 0.70. + -. 0.02), the mixture was vortexed and shaken to mix them uniformly, and reacted in the dark for 6min, and the absorbance value of the reaction solution at 734nm wavelength was measured to calculate ABTS free radical scavenging rate using the formula (2).
In the formula: a. The0Absorbance values for 0.1mL deionized water and 3.8mL ABTS solution, A1Absorbance values for 0.1mL of sample and 3.8mL of ABTS solution.
The oxidation resistance results are shown in FIGS. 8 to 9.
As can be seen from fig. 8, both the cross-linked and non-cross-linked quercetin-zein/pectin/chitosan nanoparticles have a DPPH-radical clearance higher than that of free quercetin, and may be related to the improvement of water solubility. The oxidation resistance is further improved after the cross-linking agent genipin is added, which shows that genipin and quercetin have a certain synergistic oxidation resistance.
As can be seen from fig. 9, genipin and quercetin at specific concentrations have a certain synergistic antioxidant effect. Especially when the mass ratio of genipin to zein is 1 (100-400), the ABTS & free radical clearance rate is obviously improved.
EXAMPLE 7 storage stability
(1) Sodium azide was added to the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle solution of different crosslinking degrees prepared in example 1 and the quercetin-zein/pectin/chitosan nanoparticle solution of comparative example 1 so that the concentration of sodium azide reached 0.02% to prevent bacterial growth.
(2) The solution in step (1) was dispensed into sample bottles and stored at 4 ℃ for 15 days, during which time samples were taken every 3 days to measure the particle size, potential, PDI and quercetin retention, and the results are shown in fig. 10.
As can be seen from FIGS. 10A, 10B and 10D, the particle size tended to increase within 15 days of storage, PDI increased to about 0.4 after two weeks, the uniformity of the system decreased but the uniformity was still high, and the zeta potential tended to decrease within 15 days but the absolute value was more than 30mV. As can be seen from the 10C graph, the retention rate of quercetin in the nanoparticles tended to decrease with the increase in storage time. The retention rate of quercetin in the nanoparticles with higher crosslinking degree is higher than that of uncrosslinked nanoparticles, which probably is because the crosslinked nanoparticles have more compact structure, so that the dissociation of zein kernel and pectin/chitosan coating is effectively relieved, and further the quercetin can be better wrapped in the nanoparticles. The result shows that the crosslinked nanoparticles have good storage stability and have good encapsulation and protection effects on quercetin.
Example 8 Effect of Quercetin to zein Mass ratio on the Properties and embedding Rate of genipin-crosslinked Quercetin-zein/pectin/chitosan nanoparticles
On the basis of example 1, the mass ratio of quercetin to zein is adjusted to 1, 10, 1, 15 and 20, and the embedding rate, particle size and potential results are shown in the following table:
TABLE 1 comparison table of embedding rate and particle size of different core-wall ratios
| Core to wall ratio | 1:5 | 1:10 | 1:15 | 1:20 |
| Embedding Rate (%) | 47.3 | 65.3 | 75.4 | 92.2 |
| Particle size (nm) | 316.9 | 313.8 | 294.6 | 286.9 |
| Electric potential (mV) | 40.3 | 42.5 | 39.5 | 42.7 |
As can be seen from table 1, with the decrease of the quercetin content, the embedding rate of the genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles to quercetin is significantly improved, and when the embedding rate reaches 1: when the core-wall ratio is 20, the embedding rate is the largest and reaches 92.2%, and if the core-wall ratio is further reduced, the embedding rate can not be greatly increased, the content of the core material is less, and the significance is low. Along with the reduction of the content of the quercetin, the particle size of the genipin cross-linked quercetin-zein/pectin/chitosan nano-particles is gradually reduced, and the zeta-potential absolute value is more than 30mV. All the sodium caseinate-pectin-phytosterol nanoparticles at the core-wall ratio were shown to be very stable. Therefore, the mass ratio of quercetin to zein is preferably 1.
Example 9 investigation of the effect of chitosan molecular weight on the properties of the resulting genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles
Referring to example 1, the chitosan molecular weights were 10 ten thousand, 20 ten thousand, 30 ten thousand, and 60 ten thousand, respectively, and genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles were prepared. Particle size, PDI and zeta-potential values were determined using a Malvern multiangle particle size and high sensitivity zeta potential analyzer, and the results are shown in Table 2.
TABLE 2 results of nanoparticle particle size and potential for different chitosan molecular weights
| Molecular weight of |
10 ten thousand | 20 ten thousand | 30 ten thousand | 60 ten thousand |
| Particle size (nm) | 301.8 | 294.9 | 286.9 | 633.1 |
| PDI | 0.295 | 0.287 | 0.267 | 0.489 |
| Electric potential (mV) | 35.2 | 33.7 | 44.0 | 42.7 |
From table 2, it can be seen that the particle size and PDI of the nanoparticles decrease and then increase with the increase of the molecular weight of chitosan, wherein the particle size and PDI are the smallest when the molecular weight of chitosan is 30 ten thousand, and the PDI is greater than 0.4 when the molecular weight of chitosan increases to 60 ten thousand, so that the system is relatively unstable. All the nanoparticles prepared from the chitosan with the molecular weight have zeta-potential absolute values larger than 30mV, wherein the potential absolute value is the largest when the molecular weight is 30 ten thousand.
In summary, chitosan having a molecular weight of 20 to 30 ten thousand is preferably used as the wall material.
Example 10 investigation of the effect of zein and polysaccharide mass ratio on nanoparticle properties
With pectin as a representative polysaccharide, referring to comparative example 1, the quercetin-zein/pectin nanoparticles were prepared by adjusting zein and pectin mass ratios to 10, 5:3, 5:6, respectively. The pH stability of the nanoparticles was determined for different mass ratios.
TABLE 3 particle size comparison table for different mass ratios of zein to pectin
As is clear from Table 3, most of the particles had a particle size in the range of 200 to 300 nm. The particle size of the particles tends to increase first and then decrease. According to the comparison of the particle sizes of the three groups of nanoparticles under the same pH condition, the particle size change range of the nanoparticles with the mass ratio of zein to polysaccharide of 5:3 is the minimum, and the stability is the best among the three.
Claims (5)
1. A method of preparing genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles, characterized in that the method comprises the following steps in sequence:
(1) Dissolving quercetin and zein in an ethanol-water solution to form a uniform solution with the concentration of the zein of 10 mg/mL-20 mg/mL and the concentration of the quercetin of 0.5 mg/mL-1.3 mg/mL; adding distilled water with pH of 3.0-5.0 under stirring to obtain alcohol-water solution of quercetin-zein nanoparticles;
(2) Injecting the quercetin-zein nanoparticle alcohol-water solution obtained in the step (1) into a pectin solution with the pH value of 3.0-5.0, removing ethanol in the system by rotary evaporation, and supplementing distilled water with the same volume as the lost ethanol to obtain a quercetin-zein/pectin nanoparticle water solution;
(3) Injecting the quercetin-zein/pectin nano-particle aqueous solution obtained in the step (2) into a chitosan solution with the pH value of 3.0-5.0 to obtain a quercetin-zein/pectin/chitosan nano-particle aqueous solution; wherein the molecular weight of the chitosan is 20 to 30 ten thousand; wherein the ratio of zein: the total mass ratio of pectin to chitosan is 5:3;
(4) Injecting the quercetin-zein/pectin/chitosan nanoparticle aqueous solution obtained in the step (3) into a genipin aqueous solution, mixing, reacting, and freeze-drying to obtain genipin cross-linked quercetin-zein/pectin/chitosan nanoparticles; the mass ratio of the genipin to the zein is 1 (100 to 400).
2. The method according to claim 1, wherein in step (4), the reaction conditions are mixed: stirring and crosslinking for 4-16 hours at 25-45 ℃.
3. The method according to claim 1, wherein in step (1), the mass ratio of quercetin to zein is 1.
4. A genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticle prepared by the method of any one of claims 1-3.
5. The use of genipin-crosslinked quercetin-zein/pectin/chitosan nanoparticles according to claim 4 in the preparation of functional foods and pharmaceuticals.
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