CN107987179B - Application of low-sulfated fucan in preparation of immunopotentiator - Google Patents
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Abstract
The invention relates to a preparation method and application of low sulfated fucan derived from marine brown algae. The low sulfated fucogalactan mainly comprises monosaccharide including galactose, fucose, glucose, etc., has weight average molecular weight of 5-30KD, and has hydrolyzed sulfate group content of 15-20%, galactose content of 40-45%, fucose content of 20-25%, and ratio of galactose content to fucose content of 2: 1. The low sulfated fucogalactan is derived from Laminaria japonica of brown algae, and has effect of activating macrophage in mouse abdominal cavity to release nitric oxide.
Description
Technical Field
The invention relates to preparation of biomolecules, and a preparation method and application of low sulfated fucan.
Background
The immunity is a physiological function of human body, and the organism can distinguish self and non-self components by means of the function, so that antigen substances such as pathogenic bacteria and microorganisms entering the human body or damaged cells and tumor cells generated by the organism can be destroyed and rejected, and the immunity plays a vital role in human health. Investigations have shown that cardiovascular diseases, cancer and neurodegenerative diseases are three major diseases threatening human health. The existing research shows that the immune response is possibly applied to the treatment of serious diseases such as tumor, nervous system diseases, cardiovascular diseases, diabetes and the like.
Nitric Oxide (NO) plays an important role in immune response, belongs to intercellular communication substances, and is an important signal molecule for information transmission of intercellular genetic materials; nitric oxide released in vivo has the function of dilating blood vessels, can improve cardiovascular and cerebrovascular vessels, and is important for resisting germ invasion, eliminating tumor cells and inflammation injury of organisms. Tzianabos AO has reviewed the application of polysaccharide in the field of immunomodulatory activity in this year, and it is thought that polysaccharide can effectively activate immune response, promote the release of NO, and further develop into immunopotentiator.
The ocean is considered as a huge potential drug reservoir, and the development and utilization of active substances from the ocean is an important content for understanding and utilizing the ocean at present. The marine brown algae is rich in biomass and contains various polysaccharides, and the water-soluble polysaccharides extracted and prepared by taking kelp in the brown algae as a research object are also complex and various. Research has reported that different sulfated polysaccharides in kelp have immunomodulatory effects. For example, Fang et al reported that a water-soluble homopolysaccharide (LJP-31) separated and prepared from kelp by column chromatography had an immunomodulatory effect, and it was confirmed by structural analysis that it is mainly mannoglucose; sarena et al reported that kelp fucosan and its fraction have the effect of regulating broiler chicken immunity.
The laboratory has long been devoted to the development of active substances in kelp, and polysaccharides having different monosaccharide compositions, one being sulfated heteroglycans, one being fucoidan sulfate, and the other being sulfated galactofucans, are prepared by a method of ion exchange chromatography. In a large amount of activity researches, the sulfate group plays an important role in the activity research, but the higher the content is, the better the activity is often between 10 and 30 percent, secondly, the monosaccharide composition of different components influences the expression of the activity, and the activity of polysaccharide is obviously improved along with the increase of the content of galactose. For example, the fraction obtained by fractionating the low molecular weight fraction DF degraded from fucoidan sulfate by column chromatography has significantly increased galactose content of DF1 and is most active in neuronal protection; among fractions obtained by fractionating sulfated polysaccharides of Laminaria japonica by ion column chromatography, F3 fraction containing galactose in an amount of 78.54% in the monosaccharide composition exhibited excellent radical scavenging ability as compared with other fractions. Therefore, it is highly desirable to obtain a low sulfated fucan having a monosaccharide composition based on galactose and containing a certain amount of fucose, and the preparation method is simple and feasible and is easy for mass production.
The prior sulfated polysaccharide mainly containing fucose adopts a method mainly comprising ion chromatography fractionation, so that the operation is complex, the yield is low, industrial production cannot be carried out, and the sulfate group content of the polysaccharide obtained by the increase of the concentration of elution salt is high. The present invention therefore provides a process for the preparation of a fucogalactan with low sulphation and a galactose content in the monosaccharide composition: fucose-2: 1 and exhibits good immunopotentiation; the preparation method has simple operation and considerable yield, and can be used for mass preparation.
Disclosure of Invention
In order to further discover active ingredients in kelp, the invention provides a preparation method of low sulfated fucan, which is characterized in that monosaccharide composition is mainly galactose, the ratio of galactose content to fucose content is about 2:1, and the low sulfated fucan obtained can remarkably activate macrophage and promote the generation of nitric oxide.
A method for preparing low sulfated fucan comprises the following steps:
step 2, adding 0.3-0.8mol/L dilute sulfuric acid into the polysaccharide solution prepared in the step 1 until the final concentration is 0.1-0.5mol/L, and hydrolyzing for 3-9h at 60-100 ℃ under the condition of stirring;
step 3, adding barium hydroxide into the polysaccharide solution hydrolyzed in the step 2 to neutralize to be neutral, centrifuging to remove salt, settling the obtained degradation liquid by using an organic reagent, standing overnight, and centrifuging to obtain a precipitate;
step 4, re-dissolving the precipitate obtained in the step 3 with water to ensure that the mass percentage concentration is 2-5% to prepare an aqueous solution of the precipitate;
step 5, dialyzing the water solution of the precipitate obtained in the step 4 by using a dialysis bag, and concentrating and drying the dialysate in the dialysis bag to obtain the low sulfated fucan;
wherein the organic reagent is one or two of acetonitrile and acetone;
the organic reagent has a sedimentation volume concentration of more than 90%;
the molecular weight cut-off of the dialysis bag is 1 KD.
The low sulfated fucan has the following characteristics:
the main components of the beverage comprise galactose and fucose, and also comprise a small amount of glucose, mannose, rhamnose, xylose and glucuronic acid, wherein the content of hydrolyzed sulfate groups is 15-20%, the content of galactose is 40-45%, and the content of fucose is 20-25%.
The monosaccharide composition of the low sulfated fucan has the characteristic that the ratio of the galactose content to the fucose content is about 2: 1.
The low sulfated fucan has a molecular weight of 5-30 KD.
The preparation method disclosed by the invention has the following beneficial effects:
1 the preparation process of the present invention enables to obtain a low sulfated fucan having a specific monosaccharide composition wherein galactose is predominant, fucose is minor and the ratio of the galactose content to the fucose content is about 2:1, and further containing a small amount of sulfate groups.
2 the low sulfated fucan obtained by the preparation method can obviously activate macrophages and release nitric oxide.
Drawings
FIG. 1 is a schematic diagram of a process for the preparation of a low sulfated fucan of the present invention;
FIG. 2 shows the molecular weight spectra of HPGFC of components HDF (a) and HDFA (b) in Laminaria japonica;
FIG. 3 IR spectra of components HDF and HDFA in the kelp;
figure 4 low sulfated fucan promotes NO production by RAW 264.7 cells;
figure 5 concentration dependence of low sulfated fucan HDFA on NO production by RAW 264.7 cells.
Detailed Description
The purpose, technical scheme and effect are more clear and definite, and the invention is further described in detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1A method for the preparation of a low sulfated fucan
The method comprises the following specific steps:
(1) weighing 100g of cut dry kelp, adding 3L of water, extracting at 120 ℃ for 4 hours at 100 ℃, filtering the bolting silk and the diatomite to obtain a leaching solution, concentrating to 350mL, adding magnesium chloride with the final concentration of 0.05mol/L to remove algin, centrifuging to obtain a supernatant, dialyzing to remove salt, precipitating with 85% alcohol by volume concentration after concentration, and centrifugally freeze-drying the obtained precipitate to obtain water-soluble polysaccharide;
(2) weighing 10g of polysaccharide, dissolving in 200mL of water, and fully stirring to prepare a polysaccharide solution with the mass concentration of 5%; adding 100mL of 0.6mol/L dilute sulfuric acid solution to the mixture until the final concentration is 0.2mol/L, and hydrolyzing the mixture for 7 hours at 80 ℃ under the condition of stirring;
(3) after degradation, adding a certain amount of barium hydroxide to neutralize until the pH value is 7, centrifuging for 15min at 4000r/min, discarding the precipitate to obtain a degradation solution, adding a certain amount of acetonitrile into the degradation solution to enable the final volume concentration of the acetonitrile to be 90%, stirring overnight, and centrifuging for 15min at 4000r/min to obtain a precipitate HDF;
(4) and freeze-drying the obtained precipitate, re-dissolving with water to make the mass percentage concentration be 2%, filling the solution into a dialysis bag with the molecular weight cutoff of 1KD, dialyzing with running water for 12h, dialyzing with still water for 4h, concentrating the dialysate in the dialysis bag, and freeze-drying to obtain the low-sulfated fucan HDFA.
(5) The chemical component analysis including monosaccharide composition analysis, fucose content, total sugar content, sulfate group content, molecular weight analysis and infrared analysis was performed on the obtained components HDF and HDFA in the kelp, and the results are shown in tables 1 and 2 and fig. 2 and 3 below.
TABLE 1 analysis of chemical composition of low sulfated fucans
TABLE 2 monosaccharide composition (molar ratio) of the low sulfated fucan
FIG. 2 molecular weight spectrum of HPGFC of components HDF and HDFA (from top to bottom) in Laminaria japonica;
FIG. 3 IR spectra of components HDF and HDFA in the kelp;
from the above results, it can be seen that HDF, a component in kelp, is a complex type of low sulfated heteroglycan, whose monosaccharide composition is very complex, including galactose, fucose, glucose, rhamnose, mannose, etc., and various monosaccharides are rich in content and none of them dominates; the content of heteropolysaccharide of HDFA obtained after dialysis is obviously reduced, galactose is taken as the main component in monosaccharide composition, fucose and glucose are taken as the auxiliary components, and the ratio of the content of galactose to the content of fucose is 2:1, so that the HDFA can be regarded as low-sulfated fucogalactan.
Example 2 a method for preparing low sulfated fucan,
(1) weighing 100g of cut dry kelp, adding 3L of water, extracting at 120 ℃ for 4 hours at 100 ℃, filtering the bolting silk and the diatomite to obtain a leaching solution, concentrating to 350mL, adding magnesium chloride with the final concentration of 0.05mol/L to remove algin, centrifuging to obtain a supernatant, dialyzing to remove salt, precipitating with 85% alcohol by volume concentration after concentration, and centrifugally freeze-drying the obtained precipitate to obtain water-soluble polysaccharide;
(2) weighing 10g of polysaccharide, dissolving in 200mL of water, and fully stirring to prepare a polysaccharide solution with the mass concentration of 5%; adding 100mL of 0.6mol/L dilute sulfuric acid solution to the mixture until the final concentration is 0.5mol/L, and hydrolyzing the mixture for 5 hours at 100 ℃ under the condition of stirring;
(3) after degradation, adding a certain amount of barium hydroxide to neutralize until the pH value is 7, centrifuging for 15min at 4000r/min, discarding the precipitate to obtain a degradation solution, adding a certain amount of acetonitrile into the degradation solution to enable the final volume concentration of ethanol to be 90%, stirring overnight, and centrifuging for 15min at 4000r/min to obtain a precipitate;
(4) freeze drying the obtained precipitate, dissolving with water to make the mass percentage concentration be 2%, placing the solution into dialysis bag with molecular weight cutoff of 1KD, dialyzing with running water for 12 hr, dialyzing with standing water for 4 hr, concentrating the obtained dialysate in the dialysis bag, and freeze drying to obtain low sulfated fucogalactan (as HDFB).
(5) The chemical composition of HDFB is shown in tables 3 and 4. As can be seen from the table, the resulting component is a low sulfated fucan.
TABLE 3 analysis of chemical composition of low sulfated fucans
Example 3
The difference between this example and example 2 is that the hydrolysis time is extended to 9 hours, the acetone is used as the settling reagent, and the specific steps are as follows:
(1) weighing 100g of cut dry kelp, adding 3L of water, extracting at 120 ℃ for 4 hours at 100 ℃, filtering the bolting silk and the diatomite to obtain a leaching solution, concentrating to 350mL, adding magnesium chloride with the final concentration of 0.05mol/L to remove algin, centrifuging to obtain a supernatant, dialyzing to remove salt, precipitating with 85% alcohol by volume concentration after concentration, and centrifugally freeze-drying the obtained precipitate to obtain water-soluble polysaccharide;
(2) weighing 10g of polysaccharide, dissolving in 200mL of water, and fully stirring to prepare a polysaccharide solution with the mass concentration of 5%; adding 100mL of 0.6mol/L dilute sulfuric acid solution to the mixture until the final concentration is 0.2mol/L, and hydrolyzing the mixture for 9 hours at 100 ℃ under the condition of stirring;
(3) after degradation, adding a certain amount of barium hydroxide to neutralize until the pH value is 7, centrifuging for 15min at 4000r/min, discarding the precipitate to obtain a degradation solution, adding a certain amount of acetone into the degradation solution to enable the final volume concentration of the acetone to be 90%, stirring overnight, and centrifuging for 15min at 4000r/min to obtain a precipitate;
(4) freeze drying the obtained precipitate, dissolving with water to make the mass percentage concentration be 2%, placing the solution into dialysis bag with molecular weight cutoff of 1KD, dialyzing with running water for 12 hr, dialyzing with standing water for 4 hr, concentrating the obtained dialysate in the dialysis bag, and freeze drying to obtain low sulfated fucogalactan (as HDFC).
(5) The chemical composition of the HDFC is shown in tables 5 and 6. As can be seen from the table, the resulting component is a low sulfated fucan, with galactose dominating the monosaccharide composition.
TABLE 5 chemical composition analysis of low sulfated fucans
TABLE 6 monosaccharide composition (molar ratio) of the low sulfated fucan
Example 4: low sulfated fucan in different concentrations promotes NO production by RAW 264.7 cells
The NO release condition of the stimulated RAW 264.7 cells is detected by a Griess reagent method in the test.
Test samples: the low sulfated fucogalactans HDFA, HDFB and HDFC obtained in the examples.
Drawing a standard curve: accurately preparing 1mol/L NaNO2The standard solution was diluted to 80. mu. mol/L with double distilled water and then diluted to 80, 40, 20, 10, 5, 2.5, 0. mu. mol/L NaNO by fold2And (4) standard solution. Respectively sucking 100 mu L of standard solution into a 96-well plate, setting three multiple wells for each concentration, adding 100 mu L of Griess reagent into each well, incubating at room temperature in a dark place for 10 minAfter minutes, the absorbance value was measured at 550nm using a microplate reader, and a standard curve was drawn.
Taking RAW 264.7 mouse abdominal cavity macrophages in logarithmic growth phase, preparing the cells into cell suspension by using an RPMI1640 complete culture medium, diluting the cell suspension to the concentration of 1 × 105 cells/mL, taking 100 mu L to inoculate in a 96-well plate, placing the 96-well plate in a carbon dioxide incubator at 37 ℃ and 5% for incubation for 24h, then removing the culture medium, adding 100 mu L of the prepared HDFA solution to make the final concentration of 100 mu g/mL, arranging 3 multiple wells for each sample, adding LPS (lipopolysaccharide) into a positive control group, continuing the culture for 24h at the final concentration of 1 mu g/mL, taking 100 mu L of each well, adding an equal volume of Griess reagent, uniformly mixing, after incubating for 10 min at room temperature in a dark place, measuring the absorbance value at 550nm by using an enzyme labeling instrument, substituting the result into a standard curve to calculate the NO release amount, wherein the result is shown in a concentration gradient experiment, HDFA (0.01, 0.1, 1, 10 and 100 mu g/mL) acts on RAW 264.7 cells for 24h, and the release amount is detected by a Griess method, wherein the result is shown in a graph 5.
The results of the Griess method show that compared with Ctrl, LPS can effectively activate macrophages to release a large amount of NO; HDFA were also effective in activating macrophages after co-incubation with macrophages, releasing large amounts of NO (fig. 4) and concentration-dependent (fig. 5), indicating that HDFA could be used for the development of immunopotentiators.
Figure 4 the low sulfated fucan promotes the production of NO by RAW 264.7 cells.
Figure 5 concentration dependence of low sulfated fucan HDFA on NO production by RAW 264.7 cells.
Claims (4)
1. Use of a low sulfated fucan in the preparation of an immunopotentiator;
the low sulfated fucan has the following characteristics: the main components of the composition are galactose, the galactose content is 40-45%, besides, the composition also comprises fucose, glucose and a small amount of mannose, rhamnose, xylose and glucuronic acid, wherein the fucose content is 20-25%, and the content of hydrolyzed sulfate groups is 15-20.5%; the low sulfated fucan has a molecular weight of 5-30 KD.
2. The use according to claim 1, wherein the low sulfated fucan is prepared by:
step 1, extracting water-soluble polysaccharide from kelp by a water extraction or acid extraction method to prepare a polysaccharide solution;
step 2, adding 0.3-0.8mol/L dilute sulfuric acid into the polysaccharide solution prepared in the step 1 until the final concentration is 0.1-0.5mol/L, and hydrolyzing for 3-9h at 60-100 ℃ under the condition of stirring;
step 3, adding barium hydroxide into the polysaccharide solution hydrolyzed in the step 2 to neutralize to be neutral, centrifuging to remove salt, settling the obtained hydrolysate with an organic reagent, standing overnight, and centrifuging to obtain a precipitate;
step 4, re-dissolving the precipitate obtained in the step 3 with water to ensure that the mass percentage concentration is 2-5% to prepare an aqueous solution of the precipitate;
step 5, dialyzing the water solution of the precipitate obtained in the step 4 by using a dialysis bag, and concentrating and drying the dialysate in the dialysis bag to obtain the low sulfated fucan;
wherein the organic reagent is one or two of acetonitrile and acetone;
the organic reagent has a sedimentation volume concentration of more than 90%;
the molecular weight cut-off of the dialysis bag is 1 KD.
3. Use according to claim 1, characterized in that: the monosaccharide composition of the low sulfated fucan has the characteristic that the ratio of the galactose content to the fucose content is about 2: 1.
4. Use according to claim 1, characterized in that: the immunopotentiator is a medicine or a health product.
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