CN114031693B - Chemical degradation method of dendrobium officinale polysaccharide - Google Patents
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Abstract
The invention belongs to the field of polysaccharide preparation, and particularly relates to a chemical degradation method of dendrobium officinale polysaccharide. Diethylene triamine pentaacetic acid chelated ferrous ions are adopted to react with hydrogen peroxide to form a Fenton system, and the generated hydroxyl radical is used for oxidizing and degrading the dendrobium officinale polysaccharide. The degradation method provided by the invention is simple in process, and the molecular weight of the dendrobium officinale polysaccharide treated by the method can be effectively reduced, so that the subsequent utilization of the dendrobium officinale polysaccharide is facilitated.
Description
Technical Field
The invention belongs to the field of polysaccharide preparation, and particularly relates to a chemical degradation method of dendrobium officinale polysaccharide.
Background
Dendrobium officinale (the scientific name: dendrobium officinale) is a plant of the genus Dendrobium of the family Orchidaceae, the leaves of which are in the shape of two long round needles with no branch and multiple segments. Dendrobium officinale, which is usually used as a medicine in fresh or dry stems, has the effects of nourishing yin, clearing heat, promoting fluid production, benefiting stomach, moistening lung, relieving cough, improving eyesight, strengthening body and the like, and is a traditional rare traditional Chinese medicine.
The dendrobium officinale polysaccharide is a main active component in dendrobium officinale, has the content range of more than 10-49 percent, is a water-soluble heteropolysaccharide and is formed by connecting glucose and galactose by alpha and beta- (1 → 4) glycosidic bonds. The dendrobium officinale polysaccharide has the physiological activities of enhancing immunity, resisting tumors, reducing blood sugar, resisting oxidation and the like, and has important edible and medicinal values.
However, the polysaccharide has a very low bioabsorption rate, which is less than 5% after oral ingestion. Many of the current studies are based on cellular experiments, ignoring the problem of low absorption rate, while the injection method has many safety issues. Therefore, reducing the molecular weight of polysaccharides, increasing the absorption rate of the digestive system, and improving or maintaining the physiological activity thereof are hot spots for polysaccharide research.
At present, the main degradation methods for dendrobium officinale polysaccharide include a physical degradation method, a chemical degradation method and a biological degradation method. The physical degradation method mainly comprises an ultrasonic degradation method and a microwave degradation method, other reactants are not required to be introduced, the operation is simple, but the reaction time is long, the degradation efficiency is low, and if the degradation efficiency is improved, the degradation method can be combined with other degradation methods such as acid degradation and the like (patent number: CN 200510008708.2). The biodegradation process is mainly an enzyme degradation process, and has mild reaction conditions and strong specificity, for example, the oxidative hydrolase can effectively degrade cellulose and chitosan (patent number: CN 201710735196.2). The chemical degradation method mainly comprises an acid degradation method and a hydrogen peroxide degradation method, and the reaction system is simple and short in time; however, the application limitation factor is that some preparations are toxic and harmful, which limits the application of the preparations in food. The acid degradation method generally adopts hydrochloric acid or sulfuric acid to hydrolyze glycosidic bond of polysaccharide molecule, so that the molecular weight of polysaccharide is reduced, and the reaction is simple and easy, for example, the molecular weight of Hericium erinaceus polysaccharide can be reduced by one order of magnitude by hydrolyzing with trifluoroacetic acid (patent No. CN 201711088514.7). The hydrogen peroxide degradation method utilizes redox reaction to oxidize and degrade polysaccharide, and has low cost. 3238 Zxft 3238 et al (CN 3262 Zxft 3262A) discloses a free radical degradation method of polysaccharide, which is to put polysaccharide in a complex system of organic acid, hydrogen peroxide and vitamin C, and is suitable for most of the source polysaccharides, but the reaction time is 2-72 hours, the solution concentration is in the range of 1-100mmol/L, and the concentration required is high after the reaction time is long.
Disclosure of Invention
Aiming at the technical problems, the invention aims to provide a chemical degradation method of dendrobium officinale polysaccharide, which adopts Diethylene Triamine Pentaacetic Acid (DTPA) chelated ferrous ions to react with hydrogen peroxide to form a Fenton system, and generates hydroxyl radicals to oxidize and degrade the dendrobium officinale polysaccharide.
The invention is realized by the following technical scheme:
a chemical degradation method of dendrobium officinale polysaccharide comprises the steps of reacting ferrous ions chelated by diethylenetriamine pentaacetic acid with hydrogen peroxide to form a Fenton system, oxidizing and degrading the dendrobium officinale polysaccharide by utilizing hydroxyl radicals generated by the Fenton system to obtain a crude degradation product solution, adjusting the pH value of the crude degradation product solution to precipitate and remove iron ions, precipitating with alcohol and drying to obtain the dendrobium officinale polysaccharide.
Further, the method comprises the following specific steps:
(1) Dissolving the dendrobium officinale polysaccharide in water to obtain a dendrobium officinale polysaccharide solution;
(2) Adding ferrous ions (namely DTPA-ferrous ions) chelated by diethylenetriamine pentaacetic acid into the dendrobium officinale polysaccharide solution, then adding a hydrogen peroxide solution to form a Fenton system, and carrying out oxidation reaction at room temperature to degrade the dendrobium officinale polysaccharide to obtain a crude degradation product solution;
(3) Adjusting the pH value of the degradation crude product solution, and discarding the precipitate to obtain the dendrobium officinale polysaccharide degradation solution;
(4) And carrying out alcohol precipitation on the dendrobium officinale polysaccharide degradation liquid, discarding a liquid phase, and drying and precipitating to obtain the dendrobium officinale polysaccharide.
Further, the molecular weight of the dendrobium officinale polysaccharide is 2 multiplied by 10 7 -1.5×10 5 Within the Da range; the molecular weight of the dendrobium officinale degraded polysaccharide is 5 multiplied by 10 4 -1.5×10 4 Da.
Further, in the step (1), the concentration of the dendrobium officinale polysaccharide solution is 1-10mg/mL.
Further, the step (2) is specifically as follows:
adding ferrous ions chelated by diethylenetriaminepentaacetic acid into the dendrobium officinale polysaccharide solution until the concentration of DTPA-ferrous ions in the dendrobium officinale polysaccharide solution is 5-20 μm/L; then adding a hydrogen peroxide solution until the volume ratio concentration of hydrogen peroxide in the dendrobium officinale crude polysaccharide aqueous solution is 0.05-0.5%; performing oxidation reaction at room temperature to degrade the dendrobium officinale polysaccharide, and reacting for a certain time to obtain a crude degradation product solution.
In the step, the concentration of DTPA-ferrous ion is strictly controlled to be 5-20 μm/L, the volume ratio concentration of hydrogen peroxide is strictly controlled to be 0.05-0.5%, and the molecular weight of 5 x 10 can be obtained by controlling the concentration of DTPA-ferrous ion and the volume ratio concentration of hydrogen peroxide in a Fenton system 4 -1.5×10 4 The dendrobium officinale between Da can degrade polysaccharide and can ensure that the dendrobium officinale polysaccharide is not excessively degraded into monosaccharide.
Preferably, the concentration of the selected dendrobium officinale polysaccharide is 2mg/mL, the concentration of DTPA-ferrous ion in the dendrobium officinale polysaccharide solution is 5 μm/L, and the volume ratio concentration of the hydrogen peroxide solution is 0.1%.
The method adopts diethylenetriamine pentaacetic acid (DTPA) as an important aminocarboxylate chelating agent, has extremely strong coordination capability on metal ions, particularly high-valence chromogenic metal ions, is widely applied to medical medicaments, and can promote the discharge of heavy metal poisons in vivo after chelating essential trace elements. The stability and the antioxidation effect of DTPA to the chelate formed by the transition metal are better than those of Ethylene Diamine Tetraacetic Acid (EDTA), and the DTPA can effectively complex ferrous ions used in Fenton reaction so as to reduce the possibility that the ferrous ions are oxidized into ferric ions in the reaction process.
Further, in the step (2), ferrous ions chelated by diethylenetriamine pentaacetic acid are added after the pH of the dendrobium officinale polysaccharide solution is adjusted to 3.0-4.0 in the step (2).
Further, in the step (2), the degradation time is 10-20min.
Further, in the step (3), the pH value of the degradation crude product solution is adjusted to 9.0-10.0.
Further, in the step (4), the temperature of alcohol precipitation is 3-5 ℃, and the time of alcohol precipitation is 6-18h.
The invention has the beneficial technical effects that:
1) The degradation method provided by the invention adopts a Fenton system to degrade the dendrobium officinale polysaccharide, has the advantages of short degradation time, low cost and the like, and can obviously reduce the molecular weight of the dendrobium officinale polysaccharide. The Fenton system adopted in the invention comprises ferrous ions chelated by diethylene triamine pentaacetic acid and hydrogen peroxide, wherein the hydrogen peroxide is decomposed to be used as a reaction substrate, and the generated hydroxyl free radicals attack dendrobium officinale polysaccharide molecules to achieve the effect of reducing the molecular weight of the polysaccharide; ferrous ions are used as a catalyst to participate in the decomposition of hydrogen peroxide so as to achieve the effect of rapid degradation; DTPA as a metal ion chelating agent chelates ferrous ions to enhance the stability of the DTPA, reduces the possibility of oxidation, and simultaneously chelates ferric ions generated by oxidation to avoid interference with the reaction.
2) Compared with the polysaccharide prepared by the traditional water extraction and alcohol precipitation method, the antioxidant activity of the dendrobium officinale degraded polysaccharide prepared by the degradation method provided by the invention is obviously improved.
Drawings
FIG. 1 is a high performance liquid chromatogram of polysaccharide DP of Dendrobium officinale and degraded polysaccharides DP-1, DP-2 and DP-3 of Dendrobium officinale in the embodiment of the present invention.
FIG. 2a is a graph showing the reducing power of the polysaccharide DP of Dendrobium officinale and the polysaccharide DP-1 degraded by Dendrobium officinale in the embodiment of the present invention on ferric ions; FIG. 2b is a DPPH free radical scavenging potential diagram of the polysaccharide DP of Dendrobium officinale and the degraded polysaccharide DP-1 of Dendrobium officinale in the embodiment of the present invention; FIG. 2c is a diagram of the hydroxyl radical scavenging ability of the polysaccharides DP of Dendrobium officinale and the degraded polysaccharides DP-1 of Dendrobium officinale in the embodiment of the present invention; FIG. 2d is a graph showing the total antioxidant capacity of polysaccharide DP of Dendrobium officinale and polysaccharide DP-1 of Dendrobium officinale in the embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
On the contrary, the invention is intended to cover alternatives, modifications, equivalents and alternatives which may be included within the spirit and scope of the invention as defined by the appended claims. Furthermore, in the following detailed description of the present invention, certain specific details are set forth in order to provide a better understanding of the present invention. It will be apparent to one skilled in the art that the present invention may be practiced without these specific details.
The invention provides a chemical degradation method of dendrobium officinale polysaccharide, which comprises the steps of reacting ferrous ions chelated by diethylenetriaminepentaacetic acid with hydrogen peroxide to form a Fenton system, oxidizing and degrading the dendrobium officinale polysaccharide by utilizing hydroxyl radicals generated by the Fenton system to obtain a crude degradation product solution, adjusting the pH value of the crude degradation product solution to precipitate and remove iron ions, precipitating with alcohol and drying to obtain the dendrobium officinale polysaccharide. The method specifically comprises the following steps:
(1) Dissolving dendrobium officinale polysaccharide in water to obtain a dendrobium officinale polysaccharide solution; the concentration of the dendrobium officinale polysaccharide solution is 1-10mg/mL, and the preferable concentration is 2mg/mL.
(2) Adding ferrous ions chelated by diethylenetriaminepentaacetic acid into the dendrobium officinale polysaccharide solution until the concentration of DTPA-ferrous ions in the dendrobium officinale polysaccharide solution is 5-20 μm/L; then adding a hydrogen peroxide solution until the volume concentration ratio of hydrogen peroxide in the dendrobium officinale crude polysaccharide aqueous solution is 0.05-0.5%; performing oxidation reaction at room temperature to degrade dendrobium officinale polysaccharide, and reacting for a certain time to obtain a degradation crude product solution; the degradation time is 10-20min;
preferably, the concentration of the selected dendrobium officinale polysaccharide is 2mg/mL, the concentration of DTPA-ferrous ion is 5 μm/L, and the volume ratio concentration of the hydrogen peroxide solution is 0.1%.
(3) Adjusting the pH value of the degradation crude product solution to 9-10, and discarding the precipitate to obtain the dendrobium officinale polysaccharide degradation solution;
(4) And carrying out alcohol precipitation on the dendrobium officinale polysaccharide degradation liquid, discarding a liquid phase, and drying and precipitating to obtain the dendrobium officinale polysaccharide. In this embodiment, the temperature of alcohol precipitation is 3-5 deg.C, and the time of alcohol precipitation is 6-18h.
The following description is given by way of specific examples:
comparative example
The comparative example provides a method for extracting dendrobium officinale polysaccharide by a hot water extraction method, which comprises the following steps:
weighing 0.500g of dried, crushed and 60-mesh dendrobium officinale powder, adding 25mL of 80% ethanol, uniformly mixing by vortex oscillation, carrying out 150W ultrasonic extraction for 30min, centrifuging at 6000r/min, taking precipitate, washing and centrifuging for 2-3 times by using 10mL of 80% ethanol until the supernatant is colorless; extracting the precipitate with boiling water at a material-to-liquid ratio of 1.
Example 1
The embodiment provides a chemical degradation method of dendrobium officinale polysaccharide, which comprises the following steps:
a) Preparing dendrobium officinale polysaccharide DP according to the method of the comparative example;
b) Chelating ferrous ions by using a diethylenetriaminepentaacetic acid (DTPA) solution to obtain ferrous ions chelated by the diethylenetriaminepentaacetic acid, namely DTPA-ferrous ions;
c) Preparing the dendrobium officinale crude polysaccharide DP prepared in the step a) into a dendrobium officinale polysaccharide water solution with the concentration of 2mg/mL, and adjusting the pH value to 3.0; adding DTPA-ferrous ion until the concentration of DTPA-ferrous ion in the dendrobium officinale polysaccharide water solution is 5 mu m/L; adding 1% hydrogen peroxide solution until the hydrogen peroxide concentration in the dendrobium officinale polysaccharide aqueous solution is 0.1%; carrying out oxidation reaction at room temperature;
d) After reacting for 20 minutes, adjusting the pH value of the reaction solution to 9.0, and centrifuging to remove precipitates;
e) And adjusting the pH of the supernatant to be neutral, concentrating under reduced pressure, and drying to obtain a dendrobium officinale polysaccharide free radical degradation product DP-1.
Redissolving with ultrapure water, and filtering with 0.22 μm Nylon membrane for HPLC analysis.
In this example, the column used was a C18 column (4.6X 250mm,5 μm), the mobile phase was 100% ultrapure water, the flow rate was 1mL/min, the column temperature was 30 ℃, the sample size was 20 μ L, and the running time was 15min. And comparing the standard substance according to the retention time after the operation is finished.
Example 2
This embodiment provides a chemical degradation method of dendrobium officinale polysaccharide, which is substantially the same as that of embodiment 1, except that: in the step d), the reaction time is 10min; obtaining the degradation product DP-2 of the dendrobium officinale polysaccharide.
Example 3
The embodiment provides a chemical degradation method of dendrobium officinale polysaccharide, which is basically the same as the embodiment 1, and has the only difference that: in step c), the DTPA-ferrous ion is replaced with a ferrous ion: adding ferrous ions until the concentration of the ferrous ions in the dendrobium officinale polysaccharide water solution is 5 mu m/L. Finally obtaining the dendrobium officinale polysaccharide degradation product DP-3.
FIG. 1 is a high performance liquid chromatogram of polysaccharide DP of Dendrobium officinale and polysaccharide DP-1, DP-2 and DP-3 degraded by Dendrobium officinale, which can be seen from FIG. 1: analyzing the molecular weights of DP, DP-1, DP-2 and DP-3 by high performance liquid chromatography, and determining that DP is mainly composed of polysaccharides with four molecular weights, respectively 2.4 × 10 7 Da、1.9×10 6 Da、1.3×10 6 Da、1.5×10 5 Da; DP-1 is composed primarily of two polysaccharides of molecular weight 4.7X 10, respectively 4 Da and 1.6X 10 4 Da, the molecular weight of polysaccharide after degradation is obviously lower than that of polysaccharideThe molecular weight of polysaccharide before hydrolysis is more concentrated. DP-2 has a molecular weight substantially identical to DP-1, but the proportion of low molecular weight polysaccharides is lower compared to DP-1. DP-3 is composed of two polysaccharides with molecular weights of 8.5X 10 5 Da、2.0×10 4 Da. The molecular weight of the degraded dendrobium officinale polysaccharide is obviously lower than that of the polysaccharide before degradation, but compared with the condition that the dendrobium officinale polysaccharide is degraded by chelating ferrous ions and hydrogen peroxide, the degraded dendrobium officinale polysaccharide has higher molecular weight, and the low molecular weight polysaccharide accounts for less.
Fig. 2 is a graph of antioxidant activity of dendrobium officinale polysaccharide DP and dendrobium officinale degradation polysaccharide DP-1, fig. 2a is a graph of reducing capacity for ferric ions, fig. 2b is a graph of DPPH free radical scavenging capacity, fig. 2c is a graph of hydroxyl free radical scavenging capacity, and fig. 2d is a graph of total antioxidant capacity. As shown in FIGS. 2a-d, the antioxidant capacity of the degraded Dendrobium officinale polysaccharide DP-1 is higher than that of the undegraded Dendrobium officinale polysaccharide DP, and the total antioxidant capacity of DP-1 is about 2.6 times of DP at a concentration of 3.0 mg/mL; the most obvious improvement of the antioxidant capacity is DPPH free radical scavenging capacity, and the total antioxidant capacity of DP-1 is about 5.7 times of DP under the concentration of 0.5 mg/mL.
Claims (7)
1. A chemical degradation method of dendrobium officinale polysaccharide is characterized in that ferrous ions chelated by diethylenetriaminepentaacetic acid react with hydrogen peroxide to form a Fenton system, hydroxyl free radicals generated by the Fenton system are used for oxidizing and degrading the dendrobium officinale polysaccharide to obtain a crude degradation product solution, the pH value of the crude degradation product solution is adjusted to precipitate and remove iron ions, and the crude degradation product solution is subjected to alcohol precipitation and drying to obtain the dendrobium officinale polysaccharide;
the method specifically comprises the following steps:
(1) Dissolving dendrobium officinale polysaccharide in water to obtain a dendrobium officinale polysaccharide solution;
(2) Adding ferrous ions chelated by diethylenetriaminepentaacetic acid into the dendrobium officinale polysaccharide solution, then adding a hydrogen peroxide solution to form a Fenton system, and carrying out oxidation reaction at room temperature to degrade the dendrobium officinale polysaccharide to obtain a crude degradation product solution;
(3) Adjusting the pH value of the degradation crude product solution, and discarding the precipitate to obtain the dendrobium officinale polysaccharide degradation solution;
(4) Carrying out alcohol precipitation on the dendrobium officinale polysaccharide degradation liquid, discarding a liquid phase, and drying and precipitating to obtain dendrobium officinale polysaccharide;
the step (2) is specifically as follows:
adding ferrous ions chelated by diethylenetriaminepentaacetic acid into the dendrobium officinale polysaccharide solution until the concentration of DTPA-ferrous ions in the dendrobium officinale polysaccharide solution is 5-20 mu M/L; then adding a hydrogen peroxide solution until the volume ratio concentration of hydrogen peroxide in the dendrobium officinale crude polysaccharide aqueous solution is 0.05-0.5%; performing oxidation reaction at room temperature to degrade the dendrobium officinale polysaccharide, and reacting for a certain time to obtain a crude degradation product solution.
2. The chemical degradation method of dendrobium officinale polysaccharide according to claim 1, wherein the molecular weight of the dendrobium officinale polysaccharide is 1.5 x 10 5 -2×10 7 Within the Da range; the molecular weight of the dendrobium officinale degraded polysaccharide is 1.5 multiplied by 10 4 -5×10 4 Da.
3. The chemical degradation method of dendrobium officinale polysaccharide according to claim 1, wherein in the step (1), the concentration of the dendrobium officinale polysaccharide solution is 1-10mg/mL.
4. The chemical degradation method of Dendrobium officinale polysaccharide according to claim 1, wherein in step (2), ferrous ion chelated by diethylenetriaminepentaacetic acid is added after pH of Dendrobium officinale polysaccharide solution is adjusted to 3.0-4.0.
5. The chemical degradation method of dendrobium officinale polysaccharide according to claim 1, wherein in the step (2), the degradation time is 10-20min.
6. The chemical degradation method of Dendrobium officinale polysaccharide as claimed in claim 1, wherein in step (3), the pH of the degradation crude product solution is adjusted to 9.0-10.0.
7. The chemical degradation method for dendrobium officinale polysaccharide according to claim 1, wherein in the step (4), the temperature of alcohol precipitation is 3-5 ℃, and the time of alcohol precipitation is 6-18h.
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