CN112655873B - Solubilization method of high polymer procyanidine, compound prepared by solubilization method and application of high polymer procyanidine - Google Patents
Solubilization method of high polymer procyanidine, compound prepared by solubilization method and application of high polymer procyanidine Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000005063 solubilization Methods 0.000 title claims abstract description 19
- 230000007928 solubilization Effects 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 title claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
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Abstract
The invention provides a solubilization method of high polymer procyanidine, a compound prepared by the solubilization method and application of the high polymer procyanidine; the solubilization method comprises adding polysaccharides into aqueous solution containing high polymer procyanidin, or adding polysaccharides before dissolving high polymer procyanidin in water, mixing, and stirring. According to the solubilization method of the high polymer procyanidine, provided by the invention, through adding the polysaccharide substance and through the interaction of polysaccharide-polyphenol, the high polymer procyanidine and the polysaccharide substance form a stable composite particle system in an aqueous solution under a certain condition, so that the solubility of the high polymer procyanidine and the polysaccharide substance is improved by about 70 times; the solubilization method of the high polymer procyanidine provided by the invention has simple process, is simple and convenient, and has excellent practical application effect by only adding polysaccharide substances in proportion and stirring and mixing; the compound formed by compounding the high polymer procyanidine and the polysaccharide substance has obvious weight-losing and blood sugar-reducing effects, and the synergistic effect of the high polymer procyanidine and the polysaccharide substance is obvious.
Description
Technical Field
The invention relates to the technical field of dissolution of plant functional components, in particular to a solubilization method of high polymer procyanidine, a compound prepared by the solubilization method and application of the high polymer procyanidine.
Background
Procyanidins (PACs) are the most widely occurring class of polyphenols in fruits and vegetables, and in most fruits and vegetables are mainly in the form of high-polymer procyanidins (Polymerized Proanthocyanidins, PPACs).
At present, the research on procyanidins mainly focuses on the evaluation of health effects and mechanisms of procyanidins, and it has been proved that procyanidins have various health effects such as antioxidation, bacteriostasis, anti-inflammation, glycolipid metabolism regulation and the like, however, how to widely apply procyanidins in food systems is less studied. The reason is mainly because procyanidins, especially high-polymer procyanidins, have poor water solubility and strong astringency, are extremely easy to interact with components such as proteins in food, and further influence the processing characteristics and nutritional functions of the food. These properties of procyanidins, particularly high polymeric procyanidins, severely hamper their use as food ingredients in food production and processing.
At present, aiming at high polymer procyanidins in fruits and vegetables, an oligomer procyanidin is prepared mainly in a cracking mode so as to reduce the molecular weight and improve the solubility; however, these methods are often accompanied by the characteristics of complex process, low yield, high cost, and the like.
In summary, how to overcome the technical problem of indissolvable high-polymer procyanidins is a key technical problem to be solved by the skilled in the art.
Disclosure of Invention
The invention aims to provide a solubilization method of high polymer procyanidine, a compound prepared by the solubilization method and application of the high polymer procyanidine.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a method for solubilizing high polymer procyanidin comprises adding polysaccharide substance into aqueous solution containing high polymer procyanidin, or adding polysaccharide substance before dissolving high polymer procyanidin in water; mixing and stirring.
Specifically, in the technical scheme, the high polymer procyanidine forms a stable composite particle system in the aqueous solution under the action of polysaccharide substances, so that the solubility of the high polymer procyanidine can be greatly improved, the process is simple, and the operation is convenient.
Further, in the above technical scheme, the polysaccharide substance is one or more of pectin, carrageenan, sodium alginate, konjac gum and inulin.
Preferably, in the above technical solution, the polysaccharide substance is inulin.
Further, in the above technical scheme, the mass ratio of the polysaccharide substance to the high polymer procyanidine is 20-40:1.
further, in the technical scheme, the temperature is controlled to be 20-50 ℃ in the mixing and stirring process.
Preferably, in the above technical scheme, the temperature is controlled to be 20-30 ℃ during the mixing and stirring process.
Further, in the above technical scheme, the pH is controlled to be 4-9 during the mixing and stirring process.
Preferably, in the above technical solution, the pH is controlled to be 4-7 during the mixing and stirring process.
Specifically, in the technical scheme, the polysaccharide substance is inulin, and the solubility of the high polymer procyanidine in the aqueous solution is improved from 0.15mg/ml to 10mg/ml, and the solubility is increased by 66.67 times.
The invention also provides a high polymer procyanidine compound, in particular to a compound of high polymer procyanidine and polysaccharide substances.
Specifically, in the above technical scheme, in the high polymer procyanidin compound, the polysaccharide substance is one or more of pectin, carrageenan, sodium alginate, konjak gum and inulin, and preferably inulin.
Preferably, in the above technical scheme, the mass ratio of the polysaccharide substance to the high polymer procyanidine is 20-40:1.
the reagents and materials used in the present invention are commercially available.
Compared with the prior art, the invention has the beneficial effects that:
(1) According to the solubilization method of the high polymer procyanidine, provided by the invention, through adding the polysaccharide substance and through the interaction of polysaccharide-polyphenol, the high polymer procyanidine and the polysaccharide substance form a stable composite particle system in an aqueous solution under a certain condition, so that the solubility of the high polymer procyanidine and the polysaccharide substance is improved by about 70 times;
(2) The solubilization method of the high-polymer procyanidine provided by the invention has the advantages that the process is simple, the solubilization process of the high-polymer procyanidine can be completed by adding the polysaccharide substances according to the proportion and stirring and mixing, the method is simple and convenient, and the practical application effect is excellent;
(3) The compound formed by compounding the high polymer procyanidine and the polysaccharide substance has obvious weight-losing and blood sugar-reducing effects, and the synergistic effect of the high polymer procyanidine and the polysaccharide substance is obvious.
Drawings
FIG. 1 shows the structure of a polymeric procyanidin according to an embodiment of the present invention;
FIG. 2 is a transmission electron microscope image of a high polymer procyanidin dissolved in water according to an embodiment of the present invention;
FIG. 3 is a graph showing the result of solubilization of high-polymer procyanidins by inulin aqueous solutions of different concentrations in the examples of the present invention;
FIG. 4 is a graph showing the particle size results of a complex solution at different concentrations of polymeric procyanidins in an embodiment of the present invention;
FIG. 5 is a graph showing the particle size results of complex solutions at different pH for different concentrations of polymeric procyanidins in examples of the present invention;
FIG. 6 is a graph showing the particle size results for the composites of the examples of the present invention at different pH values;
FIG. 7 shows the results of weight testing of mice in different groups in the examples of the present invention;
FIG. 8 shows the results of adipose tissue testing of mice in different groupings in the examples of the present invention;
FIG. 9 shows the results of blood glucose tests for different groups of mice in the examples of the present invention;
FIG. 10 shows liver and adipose tissue sections and HE staining results of mice grouped differently in the examples of the present invention.
Detailed Description
The present invention will be described in further detail with reference to specific examples so as to more clearly understand the present invention by those skilled in the art.
The following examples are only illustrative of the present invention and are not intended to limit the scope of the invention.
All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without making any inventive effort shall fall within the scope of the present invention.
In the embodiment of the invention, the used high polymer procyanidine is self-made persimmon high polymer procyanidine, and the extraction method comprises the following steps:
50g of persimmon pulp, and 1% hydrochloric acid-methanol mixed solution with the following components in percentage by weight: 8 (methanol 2000ml, hydrochloric acid 20 ml), condensing and refluxing at 80 ℃ for 40min, repeating for three times, mixing the extractive solutions, and standing overnight; filtering, steaming at 35deg.C, concentrating to 50ml (per 2000 ml), filtering, loading AB-8 macroporous resin, adsorbing for 40min (sealing with proper water), washing with water until no sugar is present (no loss of tannin is caused during washing process due to phenol-sulfuric acid method, soluble sugar, hydrochloric acid, methanol, etc.) is removed, washing with 10% ethanol until no color is present (small molecular substances such as pigment are removed), eluting with 90% ethanol, collecting eluate, concentrating at 35deg.C, removing ethanol (steaming), and lyophilizing to obtain persimmon tannin. Molecular structural analysis shows that the average polymerization degree is 26, and the polymer is typical high polymer procyanidine.
The inulin is commercially available natural inulin.
Examples
The structure of the high polymer procyanidin is shown in figure 1.
Preparing a persimmon high-polymer procyanidine aqueous solution with the concentration of 1mg/ml, and observing the existence form of the persimmon high-polymer procyanidine in the aqueous solution by adopting a transmission electron microscope.
The results are shown in FIG. 2, and it can be seen from FIG. 2 that the high polymer procyanidins are substantially insoluble in water and are in the form of clusters; the water insoluble nature of this material makes it difficult to apply as a food ingredient in food systems such as beverages.
Respectively preparing inulin aqueous solutions of 0.1 g/ml, 0.2 g/ml, 0.25g/ml, 0.3 g/ml and 0.4g/ml, respectively adding 10mg/ml high polymer procyanidine, vortex shaking for 5min for dissolution, measuring the granularity by using a Malvern Nano ZS laser nanometer particle sizer at 25+/-0.1 ℃, and measuring each sample in parallel for 3 times.
As a result, as shown in FIG. 3, it can be seen from FIG. 3 that the high polymer procyanidin-inulin forms stable nanoparticles, and as the inulin concentration increases, the particle size of the high polymer procyanidin-inulin complex decreases first and then increases, and at 0.25g/ml, the particle size is minimized. The particle size of the nano-composite is the reaction of the existence state of the persimmon high polymer procyanidine-inulin composite, and generally, the smaller the particle size is, the higher the clarity of the composite is, and the more stable the composite is under the same condition.
Preparing an inulin aqueous solution with the concentration of 0.25g/ml, carrying out ultrasonic dissolution, respectively adding high polymer procyanidine with the concentration of 5, 10, 15, 20, 25 and 30mg/ml, carrying out vortex oscillation for 5min for dissolution, measuring the granularity by using a Malvern Nano ZS laser nanometer particle sizer at the temperature of 25+/-0.1 ℃, and carrying out parallel measurement on each sample for 3 times.
As a result, as shown in fig. 4, it can be seen from fig. 4 that the particle size of the high polymer procyanidin-inulin complex gradually increases as the concentration of high polymer procyanidin increases; in an inulin solution of 0.25g/ml, the maximum solubility of the high polymer procyanidine is 10mg/ml, and after exceeding, the particle size of the system gradually increases, and the whole composite system tends to be unstable.
Respectively preparing inulin solutions of 0.1 g/ml, 0.2 g/ml, 0.25g/ml, 0.3 g/ml and 0.4g/ml, carrying out ultrasonic dissolution, respectively adding high polymer procyanidine of 10mg/ml, carrying out vortex oscillation for 5min for dissolution, sequentially diluting 2 times, 4 times, 8 times, 16 times and 32 times by distilled water, measuring the granularity by using a Malvern Nano ZS laser nanometer particle sizer at 25+/-0.1 ℃, and parallelly measuring each sample for 3 times. The stability under different dilution conditions was investigated using this experiment.
As shown in FIG. 5, it can be seen from FIG. 5 that the particle size of the resulting stable complex solution does not change much at various dilution factors when diluted, and this result shows that the high polymer procyanidin-inulin complex is relatively stable and the dilution has little influence on the particle size.
Preparing inulin solutions with the concentrations of 0.1, 0.2, 0.25, 0.3 and 0.4g/ml respectively by water with the pH value of 2, 4, 7, 8 and 9, carrying out ultrasonic dissolution, respectively adding 10mg/ml of high polymer procyanidine, carrying out ultrasonic treatment for 5min, carrying out vortex oscillation for 15min for dissolution, measuring the granularity by using a Malvern Nano ZS laser nanoparticle analyzer at 25+/-0.1 ℃, and carrying out parallel measurement on each sample for 3 times.
As shown in fig. 6, it can be seen from fig. 6 that the pH environment has a large influence on the high-polymer procyanidin-inulin complex, the complex is easily aggregated under strong acidic conditions, the particle size of the complex becomes large, and the complex is settled and the stability is reduced. But the compound is more stable under the environment with the pH value of 4-9, and can meet the requirements of different food environments.
Effect verification
The diet-induced obese mouse model was selected to evaluate the hypoglycemic and hypolipidemic efficacy of the complex, as follows.
About 20g of C57 mice were selected and randomly divided into five groups, including a control group, a model group, a high-polymer procyanidin-treated group, an inulin-treated group and a high-polymer procyanidin-inulin complex group, each group having 10 animals.
Wherein:
control group: feeding 12450J feed;
model group: feeding RD12492 high-fat feed;
high polymeric procyanidin treatment group: feeding RD12492 high-fat feed and high-polymer procyanidine with a daily feeding amount of 20mg/kg (weight of mice);
inulin treatment group: feeding RD12492 high-fat feed and inulin, wherein the feeding amount is 500mg/kg (weight of mice) per day;
high polymeric procyanidin-inulin complex group: feeding RD12492 high-fat feed and high-polymer procyanidin-inulin compound, wherein the feeding amount is 20mg/kg of high-polymer procyanidin (weight of mice) +500mg/kg of inulin (weight of mice) per day.
The treatment time was 8 weeks, and animal weights and feeds were weighed weekly.
After the end of the experiment, the blood, adipose tissue, liver and large intestine contents of the mice were collected for the next stage of the experiment and analysis.
Mainly comprises the weight of blood sugar, blood fat and adipose tissue. The contents of blood sugar and blood fat are measured by a kit method; adipose tissues were divided into epididymal fat pad, perirenal fat pad and inguinal fat pad, and after the mice were sacrificed under anesthesia, they were taken out and weighed to obtain the weights of three fat pads.
The results are shown in FIGS. 7-10.
FIG. 7 shows the results of weight testing of mice in different groups in the examples of the present invention.
As can be seen from fig. 7, the high polymer procyanidin-inulin complex group can significantly inhibit the occurrence of obesity in mice induced by a high fat diet, and there is a significant synergistic effect between the two.
FIG. 8 shows the results of the adipose tissue test of mice in different groups in the examples of the present invention.
As can be seen from fig. 8, the high-fat diet significantly promoted proliferation of main adipose tissues (epididymal fat pad, perirenal fat pad and inguinal fat pad) of mice, thereby inducing obesity, and the high-polymer procyanidin-inulin complex can significantly inhibit proliferation of adipose tissues.
FIG. 9 shows the results of the blood glucose test of mice in different groups according to the embodiment of the present invention.
As can be seen from fig. 9, the blood glucose of the high fat induced mice was significantly increased, while the high polymer procyanidin-inulin complex could significantly reduce the blood glucose of the high fat diet induced mice; and the two show remarkable synergistic effect.
FIG. 10 shows liver and adipose tissue sections and HE staining results of mice in different groupings in the examples of the present invention.
The liver and adipose tissue slices shown in fig. 10 show that the high-fat diet can obviously induce the occurrence of fatty liver, and liver HE staining finds that the liver tissue of the high-fat diet induction group has a large number of fatty bubbles, while the inulin-high procyanidin complex treatment group can obviously inhibit the occurrence of fatty bubbles, thereby inhibiting the occurrence of fatty liver; adipose tissue sections and HE staining also show that the high-fat diet can obviously promote the growth of fat cells, the diameter of the fat cells is larger, and the high-polymer procyanidine-inulin complex has extremely strong improvement effect.
From fig. 7 to 10, it can be found that inulin-high polymer procyanidin complex exhibits extremely strong synergistic effect, and can significantly improve obesity induced by high fat diet in mice.
Finally, the method of the present invention is only a preferred embodiment and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (1)
1. A solubilization method of high polymer procyanidine is characterized in that 0.25g/mL of inulin aqueous solution is adopted, ultrasonic dissolution is carried out, 10mg/mL of high polymer procyanidine is added, vortex oscillation is carried out for 5min for dissolution, so that the solubility of the high polymer procyanidine is improved from 0.15mg/mL to 10mg/mL, and solubilization is carried out for 66.67 times, thus obtaining a compound solution of a small-particle-size stable system.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1486700A (en) * | 2002-09-30 | 2004-04-07 | 王洪栋 | Proanthocyanidin compound and its prepn |
| CN1816537A (en) * | 2003-07-02 | 2006-08-09 | 不二制油株式会社 | Flavonoid solubilizing agent and method of solubilizing flavonoid |
| CN106793821A (en) * | 2014-08-29 | 2017-05-31 | 花王株式会社 | The manufacture method of the solid dispersions containing slightly solubility Polyphenols |
| CN111116944A (en) * | 2019-12-10 | 2020-05-08 | 四川农业大学 | Preparation method of edible procyanidin/gelatin/chitosan nanoparticles, product and application of product |
| CN111264863A (en) * | 2020-03-04 | 2020-06-12 | 中国热带农业科学院农产品加工研究所 | Procyanidine- β -glucan compound emulsion and preparation method thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1486700A (en) * | 2002-09-30 | 2004-04-07 | 王洪栋 | Proanthocyanidin compound and its prepn |
| CN1816537A (en) * | 2003-07-02 | 2006-08-09 | 不二制油株式会社 | Flavonoid solubilizing agent and method of solubilizing flavonoid |
| CN106793821A (en) * | 2014-08-29 | 2017-05-31 | 花王株式会社 | The manufacture method of the solid dispersions containing slightly solubility Polyphenols |
| CN111116944A (en) * | 2019-12-10 | 2020-05-08 | 四川农业大学 | Preparation method of edible procyanidin/gelatin/chitosan nanoparticles, product and application of product |
| CN111264863A (en) * | 2020-03-04 | 2020-06-12 | 中国热带农业科学院农产品加工研究所 | Procyanidine- β -glucan compound emulsion and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 柿单宁与果胶相互作用研究;托尔坤•买买提;《中国博士论文电子期刊数据库工程科技I辑》;20190115;第10页6.1研究目的和意义，第20-30页2.2.1柿单宁-果胶复合物溶液制备，第119页2展望 * |
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