CN109232754A - A kind of passion flower-fruit peel polysaccharide carboxy methylation modified outcome and preparation method thereof with raising antioxidant activity - Google Patents
A kind of passion flower-fruit peel polysaccharide carboxy methylation modified outcome and preparation method thereof with raising antioxidant activity Download PDFInfo
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Abstract
The present invention is that a kind of passion flower-fruit peel polysaccharide enhances antioxidant activity carboxy methylation method of modifying.Carboxy methylation modification is carried out using sodium hydroxide-chloroactic acid method, using carboxy methylation degree of substitution as index, is rung with single factor exploration NaOH concentration, reaction time, three factor of reaction temperature, obtains the carboxy methylation passion flower-fruit peel polysaccharide of different degree of substitution.The invention further relates to carboxy methylation passion flower-fruit peel polysaccharide to apply in pharmacy, especially applies in preparing anti-oxidation medicine, is included in and removes DPPH free radical drug, hydroxyl radical free radical drug, super oxygen oxygen anion drug and Fe3+Reducing power medicinal application.Artificial synthesized different degree of substitution carboxy methylation passion flower-fruit peel polysaccharide is used for antioxidation activity in vitro test by the present invention, and the application for carboxy methylation passion flower-fruit peel polysaccharide in field of medicaments provides reference frame.
Description
Technical field
The present invention relates to a kind of passion flower-fruit peel polysaccharide, and in particular to a kind of with the passionfruit for improving antioxidant activity
Skin polysaccharide carboxy methylation modified outcome and preparation method thereof.
Background technique
Passionflower (Passiflora edulis Sims) also known as passion fruit, passion fruit, belong to Passifloraceae Passiflora
Fruit is a kind of High Quality Fruit of typical integration of drinking and medicinal herbs, has very high medical value and edible value.Traditional Chinese medicine
Studies have shown that passionflower has the multiple efficacies such as anti-inflammatory, calmness, antianxiety, anti-habituation, treatment insomnia.
Polysaccharide is natural products, from a wealth of sources, has many advantages, such as small toxic side effect, noresidue, does not generate drug resistance, thus
By the attention of researcher.Modern studies have found that the bioactivity of polysaccharide and the space structure of polysaccharide are close, by physics, change
Etc. means modify its molecular structure, to assign polysaccharide more bioactivity.With proper method to polysaccharide branch into
The modification of row carboxymethyl, carboxymethylated polysaccharides dissolubility and electronegativity enhancing, and, anti-tumor activity anti-oxidant to its has very big mention
Height, and can enhance or even generate new bioactivity.The present invention carries out carboxy methylation modification to passion flower-fruit peel polysaccharide, determines it
Structure feature, the comparative studies antioxidant activity of different degree of substitution carboxymethylated polysaccharides.Related passion flower-fruit peel polysaccharide carboxylic first
The preparation of base derivative and antioxidant activity research so far there are no domestic and foreign literature are reported.
Summary of the invention
The object of the present invention is to provide the synthetic methods of carboxy methylation passion flower-fruit peel polysaccharide, and obtain different carboxy methylations
Degree of substitution passion flower-fruit peel polysaccharide anti-oxidative exercising result.
The present invention reaches above-mentioned purpose by the following technical programs:
A kind of carboxy methylation passion flower-fruit peel polysaccharide, is synthesized by following methods: passion flower-fruit peel polysaccharide being dissolved in different dense
It spends in sodium hydroxide solution, and isopropanol is added while stirring, ice bath is made uniform suspension after stirring a period of time, and by
Isopropanol-monoxone mixed liquor is gradually added dropwise, is gradually warmed up, stirring a period of time, stops reaction, is cooled to room temperature.Adjust pH value extremely
Neutrality places reaction liquid into the bag filter that molecular cut off is 3000 48h that dialyses.Rotary evaporation solution, freeze-drying, obtains
Carboxy methylation passion flower-fruit peel polysaccharide.
Application of the carboxymethylated polysaccharides of the different degree of substitution in pharmacy is also claimed in the present invention.Further
Ground, the application of different degree of substitution carboxy methylation passion flower-fruit peel polysaccharide in medicine preparation include following 4 aspects.
(1) carboxy methylation passion flower-fruit peel polysaccharide removes the application in DPPH free radical drug, carboxy methylation west in preparation
Kind lotus pericarp polysaccharide effective concentration is 10mg/mL, and carboxy methylation degree of substitution is 0.236~1.192.
(2) carboxy methylation passion flower-fruit peel polysaccharide removes the application in hydroxyl radical free radical drug, carboxy methylation west in preparation
Kind lotus pericarp polysaccharide effective concentration is 10mg/mL, and carboxy methylation degree of substitution is 0.236~1.192.
(3) carboxy methylation passion flower-fruit peel polysaccharide removes the application in ultra-oxygen anion free radical drug, carboxylic first in preparation
Base passion flower-fruit peel polysaccharide effective concentration is 10mg/mL, and carboxy methylation degree of substitution is 0.236~1.192.
(4) carboxy methylation passion flower-fruit peel polysaccharide is removing the application in reducing power drug, carboxy methylation clearly in preparation
Passion flower-fruit peel polysaccharide effective concentration is 10mg/mL, and carboxy methylation degree of substitution is 0.236~1.192.
The beneficial effects of the present invention are: artificial synthesized carboxy methylation passion flower-fruit peel polysaccharide is used for antioxidation in vitro
Activity experiment obtains the experimental result of the carboxy methylation passion flower-fruit peel polysaccharide anti-oxidative of different degree of substitution, is carboxy methylation west
Kind lotus pericarp polysaccharide provides reference frame in the application of field of medicaments.
Detailed description of the invention
Fig. 1 is the influence for implementing the different NaOH concentrations to intestines passion flower-fruit peel polysaccharide carboxy methylation degree of substitution
Fig. 2 is the influence for implementing the differential responses temperature intestines passion flower-fruit peel polysaccharide carboxy methylation degree of substitution
Fig. 3 is the influence for implementing the differential responses time intestines passion flower-fruit peel polysaccharide carboxy methylation degree of substitution
Specific embodiment
Technical scheme is described further by the following examples.
1, the preparation of passion flower-fruit peel polysaccharide
Passion flower-fruit peel is cleaned, and is dried at 50 DEG C, is crushed, 80% 85 DEG C of ethyl alcohol condensing refluxes extraction 3 times, every time
2h separates residue and drying.Above-mentioned residue 5g is weighed, distilled water is added according to certain solid-liquid ratio, Microwave Extraction filters, filtrate
It is centrifuged to obtain supernatant concentration, 4 times of volume dehydrated alcohol precipitatings are added, 4 DEG C of standings 48h, 4000r/min are centrifuged 15min, take
Clear liquid freeze-drying, obtains passion flower-fruit peel Thick many candies (WPEP).
2, passion flower-fruit peel polysaccharide carboxy methylation is modified
Passion flower-fruit peel polysaccharide is weighed, NaOH is added and uniform suspension is made in aqueous isopropanol, ice bath after stirring.It will
Mixed liquor is slowly dropped into reaction system, is gradually warmed up, and stirring stops reaction, is cooled to room temperature.PH is adjusted to as neutrality.With stream
Water and distilled water are dialysed 48h respectively.Rotary evaporation solution, freeze-drying, obtains carboxy methylation passion flower-fruit peel polysaccharide
(WPEPC)。
3, infrared spectrum analysis
The passion flower-fruit peel polysaccharide and carboxy methylation passion flower-fruit peel polysaccharide for weighing 2mg respectively be added the dry KBr of 100mg in
In agate mortar, grinding is uniform, tabletting.IR spectrum scanning is carried out, scanning range is 4000~400cm-1。
4, the measurement of carboxy methylation passion flower-fruit peel polysaccharide degree of substitution
It is separately added into the EIPC solution and the 0.25mL concentrated sulfuric acid of 0.25mL 0.5mg/mL in test tube, mixes, 125 DEG C of heating
It is taken out after 3h, adds 2mL 2,7- dihydroxy naphthlene solution heats 20min in boiling water bath, is cooled to room temperature, finally after mixing
The distilled water of 2mL is added, measures its 520nm absorption value.Meanwhile every gram of polysaccharide sample is calculated with hydroxyacetic acid substitution polysaccharide sample
The grams of middle hydroxyacetic acid calculates the value of carboxy methylation passion flower-fruit peel polysaccharide degree of substitution:
5, influence of the different NaOH concentrations to passion flower-fruit peel polysaccharide carboxy methylation degree of substitution
NaOH concentration 10%, 15%~30% is set, studies the lye of various concentration to passion flower-fruit peel polysaccharide carboxymethyl
Change the influence of degree of substitution, the result is shown in Figure 1 carboxy methylation passion flower-fruit peel polysaccharide degree of substitution is presented with the increase of NaOH mass fraction
The trend of first increases and then decreases when NaOH mass fraction is 25%, reaches maximum.
6, influence of the differential responses temperature to passion flower-fruit peel polysaccharide carboxy methylation degree of substitution
40 DEG C of reaction temperature, 50 DEG C~80 DEG C are set, study differential responses temperature to passion flower-fruit peel polysaccharide carboxy methylation
The influence of degree of substitution, is as a result shown in Fig. 3.When reaction temperature is to 60 DEG C, the degree of substitution of carboxy methylation passion flower-fruit peel polysaccharide is maximum.
When temperature continues to increase, causes monoxone hydrolysising by-product to increase and occur to degrade and make carboxy methylation in alkaline medium with polysaccharide
Passion flower-fruit peel polysaccharide degree of substitution reduces.Therefore, select sodium hydroxide-monoxone chemical method modification passion flower-fruit peel polysaccharide anti-
Answering temperature is 60 DEG C.
7, influence of the differential responses time to passion flower-fruit peel polysaccharide carboxy methylation degree of substitution
Reaction time 1h, 2h~5h are set, study the differential responses time to passion flower-fruit peel polysaccharide carboxy methylation degree of substitution
Influence, as a result see Fig. 3.With the increase in heating reaction time, the degree of substitution of carboxy methylation passion flower-fruit peel polysaccharide constantly increases
Add.1~3h of heating time, as heating time increases, the degree of substitution of carboxy methylation passion flower-fruit peel polysaccharide is dramatically increased.When adding
After the hot time is more than 3h, degree of substitution almost no longer increases.Therefore, comprehensively consider selection sodium hydroxide-monoxone chemical method to repair
The reaction time for adoring passion flower-fruit peel polysaccharide is 3h.
8, different degree of substitution carboxy methylation passion flower-fruit peel polysaccharide acts on DPPH radicals scavenging
The analyte sample fluid 2.0mL prepared is measured, 2.0mL 0.04mg/mL DPPH solution is added, and (dehydrated alcohol is as molten
Agent), 30min is protected from light after mixing well at room temperature, its absorbance A is measured at wavelength 517nmi, while measuring anhydrous second
The absorbance A of alcohol (2.0ml) and DPPH (2.0mL) mixed liquorC, dehydrated alcohol (2.0mL) and sample liquid (2.0mL) mixed liquor
Absorbance Aj。
With the continuous increase of degree of substitution, carboxy methylation passion flower-fruit peel polysaccharide is whole to the scavenging effect of DPPH free radical
It is on a declining curve.When degree of substitution is 0.435, DPPH free radical scavenging activity is maximum, is 92.74%.When degree of substitution is 0.473
When, DPPH free radical scavenging activity is minimum, is 81.21%.Illustrate that the degree of substitution of carboxy methylation modification is bigger, passion flower-fruit peel polysaccharide
It is weaker to the Scavenging activity of DPPH free radical, show that carboxy methylation modification is unfavorable for passion flower-fruit peel polysaccharide and removes DPPH freedom
Base.
9, different degree of substitution carboxy methylation passion flower-fruit peel polysaccharide is to hydroxyl radical free radical scavenging effect
It takes the FeSO4-EDTA mixed liquor (10mmol/L) of 0.2mL in test tube with ground stopper, α-deoxyribose of 0.2mL is added
Solution (20mmol/L) then adds 0.2mL sample, and is settled to phosphate buffer (0.2mol/L, pH=7.4)
Then the H of 0.2mL is added in 1.8mL2O2(10mmol/L), 40 DEG C of water bath with thermostatic control 1h, the trichloroacetic acid that 1mL 2.8% is added terminate
Reaction, adds 1% thiobarbituricacidα- of 1mL, heats 10min after mixing in boiling water bath, surveys at 532nm after cooling
Absorbance value AS.Using deionized water as negative control, light absorption value A is measured0, ascorbic acid is positive control, measures light absorption value AC。
With the continuous increase of degree of substitution, carboxy methylation passion flower-fruit peel polysaccharide shows not the scavenging effect of hydroxy radical
Regularity, illustrating, which influences it, inhibits the factor of hydroxy radical more complicated.Generally, the degree of substitution of carboxy methylation modification is bigger,
The ability of the scavenging hydroxyl of passion flower-fruit peel polysaccharide is stronger, and when degree of substitution is 1.192, hydroxyl radical free radical clearance rate is maximum
It is 98.79%, shows that carboxy methylation is modified with conducive to passion flower-fruit peel polysaccharide scavenging hydroxyl.
10, different degree of substitution carboxy methylation passion flower-fruit peel polysaccharide is to ultra-oxygen anion free radical scavenging effect
Accurate measuring 4.5mL Tris-HCl solution (50mmol/L, pH=8.2) preheats in 25 DEG C of warm water in test tube
20min sequentially adds pyrogallol solution (25mmo1/L) 0.3mL and sample 0.2mL preheated under same preheating condition later,
And mix pour into cuvette rapidly, absorbance A t is measured at wavelength 319nm, every 30s surveys primary, measurement 8 times.Made with deionized water
For blank control, is measured under same operation conditions and calculate mouse thymus cells rate V0。
Carboxy methylation passion flower-fruit peel polysaccharide is to the Scavenging activity of ultra-oxygen anion free radical, with becoming larger for degree of substitution
Decline.But clearly linear rule is not presented.When degree of substitution is 1.192, superoxide anion clearance rate is the most
60.11%.
11, different degree of substitution carboxy methylation passion flower-fruit peel polysaccharide is to Fe3+Reducing power effect
It pipettes in 0.5mL carboxymethylated polysaccharides solution and test tube, and 0.5mL 0.2mol/L PBS buffer solution (pH=is added
6.7) and 1% potassium ferricyanide solution of 0.5mL, cooling after 50 DEG C of water-bath constant temperature 20min, 10% trichloroacetic acid of 0.5mL is added
Solution sequentially adds 2mL distilled water, the FeCl of 0.5mL 0.1%3Solution mixes well, stand 10min after, it is ultraviolet-can
See measurement solution light absorption value at spectrophotometer 700nm wavelength.
With the continuous increase of degree of substitution, the reproducibility effect of carboxy methylation passion flower-fruit peel polysaccharide is in downward trend.
But there is no the negative correlativing relations for being in highly significant between degree of substitution and clearance rate.When degree of substitution is 0.268, absorbance is most
Greatly 0.579.
Claims (7)
1. a kind of preparation method of carboxy methylation passion flower-fruit peel polysaccharide, which is characterized in that the carboxy methylation passionfruit
Skin polysaccharide is synthesized by following methods: passion flower-fruit peel being dissolved in various concentration sodium hydroxide solution, and isopropanol is added simultaneously
Uniform suspension is made after stirring 1h, 2h~5h in stirring, ice bath, and isopropanol-monoxone mixed liquor is gradually added dropwise, and gradually rises
Temperature stirs 3h, stops reaction, be cooled to room temperature to 40 DEG C, 50 DEG C~80 DEG C；It adjusts pH value to neutrality, places reaction liquid into retention
Dialyse 48h in the bag filter that molecular weight is 3000；Rotary evaporation solution, freeze-drying, it is more to obtain carboxy methylation passion flower-fruit peel
Sugar.
2. carboxy methylation passion flower-fruit peel polysaccharide according to claim 1, which is characterized in that passion flower-fruit peel polysaccharide is being made
Medicinal application.
3. carboxy methylation passion flower-fruit peel polysaccharide according to claim 1, which is characterized in that passion flower-fruit peel polysaccharide is being made
It is applied in standby anti-oxidation medicine.
4. the application of carboxy methylation passion flower-fruit peel polysaccharide according to claim 2, which is characterized in that passion flower-fruit peel is more
Sugar removes the application in DPPH free radical drug in preparation, and carboxy methylation passion flower-fruit peel polysaccharide effective concentration is 10mg/mL, carboxylic
The degree of substitution that methylates is 0.236~1.192.
5. the application of carboxy methylation passion flower-fruit peel polysaccharide according to claim 2, which is characterized in that passion flower-fruit peel is more
Sugar removes the application in hydroxyl radical free radical drug in preparation, and carboxy methylation passion flower-fruit peel polysaccharide effective concentration is 10mg/mL, carboxylic
The degree of substitution that methylates is 0.236~1.192.
6. the application of carboxy methylation passion flower-fruit peel polysaccharide according to claim 3, which is characterized in that passion flower-fruit peel is more
Sugar removes the application in ultra-oxygen anion free radical drug in preparation, and carboxy methylation passion flower-fruit peel polysaccharide effective concentration is
10mg/mL, carboxy methylation degree of substitution are 0.236~1.192.
7. the application of carboxy methylation passion flower-fruit peel polysaccharide according to claim 3, which is characterized in that passion flower-fruit peel is more
Sugar is removing the application in reducing power drug clearly in preparation, and carboxy methylation passion flower-fruit peel polysaccharide effective concentration is 10mg/mL,
Carboxy methylation degree of substitution is 0.236~1.192.
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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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