CN109232754B - Passiflora edulis pericarp polysaccharide carboxymethylation modified product with improved antioxidant activity and preparation method thereof - Google Patents
Passiflora edulis pericarp polysaccharide carboxymethylation modified product with improved antioxidant activity and preparation method thereof Download PDFInfo
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- CN109232754B CN109232754B CN201810701304.9A CN201810701304A CN109232754B CN 109232754 B CN109232754 B CN 109232754B CN 201810701304 A CN201810701304 A CN 201810701304A CN 109232754 B CN109232754 B CN 109232754B
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
Abstract
The invention relates to a carboxymethylation modification method for enhancing antioxidant activity of passion fruit peel polysaccharide. Carboxymethylation modification is carried out by adopting a sodium hydroxide-chloroacetic acid method, carboxymethylation substitution degree is taken as an index, and three factors of NaOH concentration, reaction time and reaction temperature are considered by using a single factor, so as to obtain carboxymethylation passion fruit peel polysaccharide with different substitution degrees. The invention also relates to the application of carboxymethylated passion fruit peel polysaccharide in pharmacy, in particular to the application in preparing antioxidant drugs, including DPPH free radical scavenging drugs, hydroxyl free radical drugs, superoxide anion drugs and Fe3+Application of reducing power medicine. The invention uses the artificially synthesized carboxymethylated passion fruit peel polysaccharide with different degrees of substitution in an in vitro antioxidant activity test, and provides a reference basis for the application of the carboxymethylated passion fruit peel polysaccharide in the field of medicine.
Description
Technical Field
The invention relates to passion fruit peel polysaccharide, in particular to a passion fruit peel polysaccharide carboxymethylation modified product with improved antioxidant activity and a preparation method thereof.
Background
Passiflora edulis Sims, also known as passion fruit and passion fruit belong to Passiflora plant fruits of Passiflora in Passifloraceae, are typical high-quality fruits with homology of medicine and food, and have high medicinal value and edible value. The traditional Chinese medicine research shows that the passion flower has various effects of diminishing inflammation, calming, resisting anxiety, resisting addiction, treating insomnia and the like.
The polysaccharide is a natural product, has wide sources, has the advantages of small toxic and side effects, no residue, no drug resistance and the like, and is thus valued by researchers. Modern researches find that the biological activity of the polysaccharide is close to the spatial structure of the polysaccharide, and the molecular structure of the polysaccharide is modified by means of physical, chemical and the like, so that the polysaccharide is endowed with more biological activity. Carboxymethyl modification is carried out on the polysaccharide branched chain by a proper method, the solubility and electronegativity of the carboxymethylated polysaccharide are enhanced, the antioxidant and antitumor activities of the carboxymethylated polysaccharide are greatly improved, and new biological activities can be enhanced and even generated. The invention carries out carboxymethylation modification on passion fruit peel polysaccharide, determines the structural characteristics of the passion fruit peel polysaccharide, and comparatively researches the antioxidant activity of carboxymethylation polysaccharide with different degrees of substitution. The research on the preparation of the passion fruit peel polysaccharide carboxymethylation derivative and the antioxidant activity is not reported in domestic and foreign documents.
Disclosure of Invention
The invention aims to provide a synthetic method of carboxymethylation passion fruit peel polysaccharide and obtain the antioxidant effect result of the passion fruit peel polysaccharide with different carboxymethylation substitution degrees.
The invention achieves the above purpose by the following technical scheme:
the carboxymethylated passion fruit peel polysaccharide is synthesized by the following method: dissolving passion fruit peel polysaccharide in sodium hydroxide solutions with different concentrations, adding isopropanol, stirring simultaneously, carrying out ice bath, stirring for a period of time to prepare uniform suspension, gradually dropwise adding an isopropanol-chloroacetic acid mixed solution, gradually heating, stirring for a period of time, stopping reaction, and cooling to room temperature. Adjusting pH to neutral, and dialyzing the reaction solution in a dialysis bag with molecular weight cutoff of 3000 for 48 h. And rotationally evaporating the solution, and freeze-drying to obtain carboxymethylated passion fruit peel polysaccharide.
The invention also claims the application of the carboxymethylated polysaccharides with different degrees of substitution in pharmacy. Further, the application of carboxymethylated passion fruit peel polysaccharide with different degrees of substitution in the preparation of medicaments comprises the following 4 aspects.
(1) The application of carboxymethylated passion fruit peel polysaccharide in preparation of a medicine for removing DPPH free radicals is characterized in that the effective concentration of carboxymethylated passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylated substitution degree is 0.236-1.192.
(2) The carboxymethylation passion fruit peel polysaccharide is applied to preparation of a medicament for removing hydroxyl free radicals, the effective concentration of the carboxymethylation passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylation substitution degree is 0.236-1.192.
(3) The carboxymethylation passion fruit peel polysaccharide is applied to preparation of a medicine for removing superoxide anion free radicals, the effective concentration of the carboxymethylation passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylation substitution degree is 0.236-1.192.
(4) The carboxymethylation passion fruit peel polysaccharide is applied to preparation of a drug for removing reducing power, the effective concentration of the carboxymethylation passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylation substitution degree is 0.236-1.192.
The invention has the beneficial effects that: the artificially synthesized carboxymethylated passion fruit peel polysaccharide is used for an in-vitro antioxidant activity experiment to obtain the antioxidant experiment result of the carboxymethylated passion fruit peel polysaccharide with different substitution degrees, thereby providing a reference basis for the application of the carboxymethylated passion fruit peel polysaccharide in the field of medicine.
Drawings
FIG. 1 is a graph showing the effect of different NaOH concentrations on carboxymethylation substitution of pericarp polysaccharides of Passiflora edulis
FIG. 2 shows the effect of carboxymethylation degree of polysaccharide in pericarp of passion flower on fruit at different reaction temperatures
FIG. 3 shows the effect of the carboxymethylation degree of polysaccharide in the pericarp of passion flower on fruit with different reaction time
Detailed Description
The technical solution of the present invention is further illustrated by the following examples.
1. Preparation of passion fruit peel polysaccharide
Cleaning passion fruit peel, drying at 50 deg.C, pulverizing, extracting with 80% ethanol under reflux at 85 deg.C for 3 times, each for 2 hr, separating residue, and drying. Weighing 5g of the residues, adding distilled water according to a certain material-liquid ratio, performing microwave extraction, performing suction filtration, centrifuging the filtrate to obtain a supernatant, concentrating, adding 4 times of volume of absolute ethyl alcohol for precipitation, standing at 4 ℃ for 48h, performing 4000r/min, centrifuging for 15min, and freeze-drying the supernatant to obtain crude passion fruit peel polysaccharide (WPEP).
2. Carboxymethylation modification of passion fruit peel polysaccharide
Weighing passion fruit peel polysaccharide, adding NaOH and isopropanol solution, carrying out ice bath, and stirring to prepare uniform suspension. Slowly dripping the mixed solution into the reaction system, gradually heating, stirring, stopping the reaction, and cooling to room temperature. The pH was adjusted to neutral. Dialyzing with running water and distilled water for 48 h. Rotary evaporating the solution, and freeze drying to obtain carboxymethylated passion fruit peel polysaccharide (WPEPC).
3. Infrared spectroscopic analysis
Respectively weighing 2mg of passion fruit peel polysaccharide and carboxymethylated passion fruit peel polysaccharide, adding 100mg of dried KBr into an agate mortar, grinding uniformly, and tabletting. Performing infrared spectrum scanning within 4000-400 cm-1。
4. Measurement of carboxymethylated passion fruit peel polysaccharide substitution degree
Respectively adding 0.25mL of 0.5mg/mL EIPC solution and 0.25mL of concentrated sulfuric acid into a test tube, uniformly mixing, heating at 125 ℃ for 3h, taking out, adding 2mL of 2, 7-dihydroxynaphthalene solution, uniformly mixing, heating in a boiling water bath for 20min, cooling to room temperature, adding 2mL of distilled water, and measuring the 520nm absorption value. Meanwhile, the glycolic acid is used for replacing the polysaccharide sample to calculate the gram of the glycolic acid in each gram of the polysaccharide sample, and the value of the carboxymethylated passion fruit peel polysaccharide substitution degree is calculated as follows:
5. influence of different NaOH concentrations on carboxymethylation substitution degree of passion fruit peel polysaccharide
Setting the concentration of NaOH to be 10 percent and 15-30 percent, and researching the influence of alkali liquor with different concentrations on the carboxymethylation substitution degree of passion fruit peel polysaccharide, wherein the result is shown in figure 1. the carboxymethylation substitution degree of passion fruit peel polysaccharide shows the trend of increasing firstly and then decreasing along with the increase of the mass fraction of NaOH, and the maximum value is reached when the mass fraction of NaOH is 25 percent.
6. Influence of different reaction temperatures on carboxymethylation substitution degree of passion fruit peel polysaccharide
The reaction temperature is set to be 40 ℃ and 50-80 ℃, the influence of different reaction temperatures on the carboxymethylation substitution degree of passion fruit peel polysaccharide is researched, and the result is shown in figure 3. When the reaction temperature reaches 60 ℃, the substitution degree of carboxymethylated passion fruit peel polysaccharide is maximum. When the temperature is increased continuously, chloroacetic acid hydrolysis byproducts are increased and polysaccharide is degraded in an alkaline medium, so that the degree of substitution of carboxymethylated passion fruit peel polysaccharide is reduced. Therefore, the reaction temperature for modifying the passion fruit peel polysaccharide by a sodium hydroxide-chloroacetic acid chemical method is 60 ℃.
7. Influence of different reaction time on carboxymethylation substitution degree of passion fruit peel polysaccharide
Setting the reaction time to be 1h and 2-5 h, and researching the influence of different reaction times on the carboxymethylation substitution degree of passion fruit peel polysaccharide, wherein the result is shown in figure 3. Along with the increase of the heating reaction time, the substitution degree of carboxymethylated passion fruit peel polysaccharide is increased continuously. The heating time is 1-3 h, and the substitution degree of carboxymethylated passion fruit peel polysaccharide is obviously increased along with the increase of the heating time. When the heating time exceeds 3 hours, the degree of substitution hardly increases. Therefore, the reaction time for modifying the passion fruit peel polysaccharide by the sodium hydroxide-chloroacetic acid chemical method is comprehensively considered to be 3 h.
8. DPPH free radical scavenging effect of carboxymethylated passion fruit peel polysaccharide with different substitution degrees
Measuring 2.0mL of prepared sample solution to be detected, adding 2.0mL of 0.04mg/mL DPPH solution (absolute ethyl alcohol as solvent), mixing well, reacting in dark at room temperature for 30min, and measuring absorbance A at wavelength of 517nmiSimultaneously, the absorbance A of a mixture of absolute ethanol (2.0mL) and DPPH (2.0mL) was measuredCAbsorbance A of a mixture of absolute ethanol (2.0mL) and sample solution (2.0mL)j。
Along with the continuous increase of the substitution degree, the clearance effect of the carboxymethylated passion fruit peel polysaccharide on DPPH free radicals is in a descending trend overall. The DPPH radical clearance is maximal at 92.74% with a degree of substitution of 0.435. At a degree of substitution of 0.473, the DPPH radical scavenging rate was the smallest, 81.21%. The larger the substitution degree of carboxymethylation modification is, the weaker the scavenging capacity of the passion fruit peel polysaccharide on DPPH free radicals is, and the carboxymethylation modification is proved to be unfavorable for the passion fruit peel polysaccharide to scavenge DPPH free radicals.
9. Hydroxyl radical scavenging effect of carboxymethylated passion fruit peel polysaccharide with different substitution degrees
0.2mL of FeSO4-EDTA mixture (10mmol/L) was put in a stoppered tube, 0.2mL of an α -deoxyribose solution (20mmol/L) was added, then 0.2mL of the sample was added, and the volume was adjusted to 1.8mL with phosphate buffer (0.2mol/L, pH 7.4), then 0.2mL of H was added2O2(10mmol/L), performing thermostatic water bath at 40 ℃ for 1h, adding 1mL of 2.8% trichloroacetic acid to stop the reaction, adding 1mL of 1% thiobarbituric acid, uniformly mixing, and heating in boiling water bath for 10min, cooling, and measuring light absorption value A at 532nmS. Using deionized water as negative control, determining light absorption value A0Ascorbic acid as positive control, and measuring absorbance AC。
Along with the continuous increase of the substitution degree, the clearance effect of carboxymethylated passion fruit peel polysaccharide on hydroxyl radical shows irregularity, which shows that the factors influencing the inhibition of the hydroxyl radical are more complex. In general, the larger the degree of substitution of carboxymethylation modification, the stronger the capacity of passion fruit peel polysaccharide in scavenging hydroxyl radicals, and when the degree of substitution is 1.192, the maximum clearance rate of hydroxyl radicals is 98.79%, which indicates that carboxymethylation modification is beneficial to the passion fruit peel polysaccharide in scavenging hydroxyl radicals.
10. Peroxyanion free radical scavenging effect of carboxymethylated passion fruit peel polysaccharide with different substitution degrees
Precisely measuring 4.5mL of Tris-HCl solution (50mmol/L, pH 8.2) in a test tube, preheating in warm water At 25 ℃ for 20min, sequentially adding 0.3mL of pyrogallol solution (25mmo1/L) preheated under the same preheating condition and 0.2mL of sample, quickly mixing, pouring into a cuvette, measuring the absorbance At the wavelength of 319nm, measuring once every 30s, and measuring 8 times. The auto-oxidation rate V of the pyrogallol is measured and calculated under the same operation condition by taking deionized water as a blank control0。
The scavenging capacity of carboxymethylated passion fruit peel polysaccharide on superoxide anion free radicals is reduced along with the increase of the degree of substitution. But does not exhibit a clear linear law. The superoxide anion clearance was at most 60.11% when the degree of substitution was 1.192.
11. Carboxymethylated passion fruit peel polysaccharide pair Fe with different substitution degrees3+Effect of reducing ability
Transferring 0.5mL carboxymethylated polysaccharide solution into a test tube, adding 0.5mL 0.2mol/L PBS buffer solution (pH 6.7) and 0.5mL 1% potassium ferricyanide solution, keeping the temperature of a water bath kettle at 50 deg.C for 20min, cooling, adding 0.5mL 10% trichloroacetic acid solution, sequentially adding 2mL distilled water and 0.5mL 0.1% FeCl3The solution is fully mixed, and after standing for 10min, the light absorption value of the solution is measured at the 700nm wavelength of an ultraviolet-visible spectrophotometer.
With the continuous increase of the substitution degree, the reducing effect of the carboxymethylated passion fruit peel polysaccharide is in a descending trend. There is no very significant negative correlation between degree of substitution and clearance. When the degree of substitution was 0.268, the absorbance was 0.579 at the maximum.
Claims (1)
1. The application of carboxymethylated passion fruit peel polysaccharide in preparing an antioxidant medicament is characterized in that the carboxymethylated passion fruit peel polysaccharide is applied in preparing a medicament for removing DPPH free radicals, the effective concentration of the carboxymethylated passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylated substitution degree is 0.435;
the carboxymethylation passion fruit peel polysaccharide is applied to the preparation of the medicament for removing the hydroxyl free radicals, the effective concentration of the carboxymethylation passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylation substitution degree is 1.192;
the carboxymethylation passion fruit peel polysaccharide is applied to the preparation of the medicine for removing superoxide anion free radicals, the effective concentration of the carboxymethylation passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylation substitution degree is 1.192;
the carboxymethylated passion fruit peel polysaccharide is applied to the preparation of a medicament for removing the reducing power, the effective concentration of the carboxymethylated passion fruit peel polysaccharide is 10mg/mL, and the carboxymethylated substitution degree is 0.268.
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| CN111825780A (en) * | 2020-08-27 | 2020-10-27 | 桂林理工大学 | Preparation method and degradation process of passion flower pericarp enzyme-assisted alkali extraction polysaccharide |
| CN111961698A (en) * | 2020-08-27 | 2020-11-20 | 桂林理工大学 | Preparation method and application of passion fruit peel polysaccharide degraded by lactobacillus brevis enzyme production |
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