CN112175107B - Method for extracting fucosan sulfate and chondroitin sulfate from sea cucumber - Google Patents
Method for extracting fucosan sulfate and chondroitin sulfate from sea cucumber Download PDFInfo
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- CN112175107B CN112175107B CN202011107485.6A CN202011107485A CN112175107B CN 112175107 B CN112175107 B CN 112175107B CN 202011107485 A CN202011107485 A CN 202011107485A CN 112175107 B CN112175107 B CN 112175107B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0069—Chondroitin-4-sulfate, i.e. chondroitin sulfate A; Dermatan sulfate, i.e. chondroitin sulfate B or beta-heparin; Chondroitin-6-sulfate, i.e. chondroitin sulfate C; Derivatives thereof
Abstract
The invention provides a method for synchronously extracting fucosan sulfate and chondroitin sulfate from sea cucumber, which more effectively utilizes the difference of the structure and the water solubility of the fucosan sulfate and the chondroitin sulfate in the tissues of the sea cucumber to complete the extraction and separation of two sulfated polysaccharides in the sea cucumber. The method has the advantages of mild extraction conditions and simple and convenient process, and can effectively extract, separate and purify the chondroitin sulfate and the fucosan sulfate from the sea cucumber; the steps of ion chromatographic separation, gel chromatographic purification, desalination and the like of fucosan sulfate and chondroitin sulfate in the sea cucumber are saved, and the separation and purification process of fucosan sulfate and chondroitin sulfate in the sea cucumber is greatly simplified. The method has low cost, easy expansion and high recovery rate, and is a green and environment-friendly method for preparing the pure products of the fucosan sulfate and the chondroitin sulfate of the sea cucumber on a large scale.
Description
Technical Field
The invention belongs to the technical field of separation and purification, and particularly relates to a method for extracting and separating fucosan sulfate and chondroitin sulfate from sea cucumbers.
Background
Sea cucumber is an organism belonging to the class Holothuria of the phylum Echinodermata, and is a precious marine product rich in active substances such as proteins, polysaccharides, saponins and the like. The sea cucumber body wall is rich in sulfated polysaccharides, mainly comprising two sulfated polysaccharides, namely fucoidan sulfate and fucosyl chondroitin sulfate. The sea cucumber fucoidan sulfate is a linear macromolecular sulfated polysaccharide formed by connecting fucose by alpha 1 → 3 or alpha 1 → 4 bonds, has a small amount of fucose side chains, and has a molecular weight generally greater than 500-700 kDa. The sea cucumber chondroitin sulfate is a specific chondroitin sulfate with fucose branched chains in sea cucumbers, consists of repeated disaccharide units of glucuronic acid and acetylgalactosamine, is formed by connecting beta-1, 4-and beta-1, 3 glycosidic bonds, and sulfated fucose branched chains are arranged on the acetylgalactosamine and the glucuronic acid, and the molecular weight is 80-120 kDa. The sulfate radical content of the sea cucumber chondroitin sulfate is more than 30 percent and is far higher than that of fucosan sulfate, so that the sea cucumber chondroitin sulfate has better anticoagulant and antithrombotic activity.
Fucosan sulfate and chondroitin sulfate in sea cucumber are two sulfated polysaccharides with different structures and biological activities, so that separation and purification are required. The currently adopted protease enzymolysis and water extraction methods can extract sea cucumber sulfated polysaccharides from sea cucumber, which are a mixture of fucosan sulfate and chondroitin sulfate, so that the two sulfated polysaccharides need to be separated. At present, the fucosan sulfate and the chondroitin sulfate are separated and purified mainly by ethanol fractionation, salt fractionation, ion exchange chromatography, two-aqueous phase extraction and gel chromatography. The most common methods are anion exchange column chromatography and aqueous two-phase extraction, which mix a large amount of salt, resulting in large desalting workload and expensive anion column. The separation efficiency of the holothurian sulfated polysaccharides by ethanol fractionation and salt fraction separation is lower, and the product purity is low. Gel chromatography is too low in sample amount per treatment to realize mass production.
Disclosure of Invention
Aiming at the defects of the extraction, separation and purification technology of fucosan sulfate and chondroitin sulfate of sea cucumber in the prior art, the invention provides a method for synchronously extracting fucosan sulfate and chondroitin sulfate from sea cucumber, which more effectively utilizes the difference of the structure and water solubility of fucosan sulfate and chondroitin sulfate in the tissue of sea cucumber to complete the extraction and separation of two sulfated polysaccharides in sea cucumber.
The method for extracting fucosan sulfate and chondroitin sulfate from sea cucumber provided by the invention comprises the following steps:
1) sea cucumber pretreatment:
crushing tissue of sea cucumber, adding distilled water for leaching, centrifuging after leaching is finished, and taking precipitate for later use;
the mass ratio of the sea water to the water is 1:5-1: 10;
the distilled water is used for leaching, and the leaching is carried out for 30-60min at the temperature of 30-50 ℃ by stirring.
2) Aqueous solution extraction and separation:
adding Tris-HCl aqueous solution into the sediment obtained by centrifugation in the step 1) for extraction, centrifuging after extraction is finished, and collecting an extracting solution and the sediment;
the Tris-HCl aqueous solution, one embodiment of which is specifically described as having a concentration of 0.1-0.3mol/L, pH8.0, and containing 4mmol/L EDTA;
the extraction is carried out by slowly stirring and extracting for 12-24h at 30-50 ℃;
3) vacuum concentrating the extracting solution obtained in the step 2), adding cetylpyridinium chloride for precipitation, and centrifugally collecting the precipitate; dissolving the precipitate in an alcoholic solution containing NaCl; then precipitating with 90% ethanol water solution, and freeze drying to obtain dried product of fucoidan sulfate;
one of the NaCl-added alcoholic solutions is a 86% ethanol solution added with 3mol/L sodium chloride;
one of the ethanol water solutions used for precipitation is a 90% ethanol water solution;
4) adding the precipitate obtained in the step 2) into compound protease, and carrying out enzymolysis for 3-5h in water bath at 45-60 ℃;
the compound protease is a mixture of alkaline protease and trypsin;
5) centrifuging the enzymolysis liquid obtained in the step 4), and collecting supernatant; after the supernatant fluid is concentrated in vacuum, ultrafiltration is adopted for deproteinization and desalination, and trapped fluid is collected; vacuum concentrating and drying the trapped fluid to obtain a fucosyl chondroitin sulfate dry product;
the ultrafiltration membrane is an ultrafiltration membrane with the molecular weight cutoff of 5kDa-20 kDa.
The method has the advantages of mild extraction conditions and simple and convenient process, and can effectively extract, separate and purify the chondroitin sulfate and the fucosan sulfate from the sea cucumber; the steps of ion chromatographic separation, gel chromatographic purification, desalination and the like of fucosan sulfate and chondroitin sulfate in the sea cucumber are saved, and the separation and purification process of fucosan sulfate and chondroitin sulfate in the sea cucumber is greatly simplified. The method has low cost, easy expansion and high recovery rate, and is a green and environment-friendly method for preparing the pure products of the fucosan sulfate and the chondroitin sulfate of the sea cucumber on a large scale.
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FIG. 1 is a graph of high performance gel exclusion chromatography analysis of fucoidan sulfate from fresh Apostichopus japonicus selenka;
FIG. 2 is a graph of high performance gel exclusion chromatography analysis of fresh chondroitin sulfate from Apostichopus japonicus;
FIG. 3 is a high performance liquid chromatogram for monosaccharide composition analysis of fucoidan sulfate from Apostichopus japonicus;
FIG. 4 is a high performance liquid chromatogram of the monosaccharide composition analysis of the Apostichopus japonicus chondroitin sulfate.
Detailed Description
In the research of the applicant, the chondroitin sulfate in the body wall of the sea cucumber is wound on collagen fibers to form a collagen fibril supermolecular structure which is insoluble in water. The fucosan sulfate is distributed in the body wall of the sea cucumber, is rich in sulfate radicals, is not combined with protein, and is easy to dissolve in water. The invention adopts an aqueous solution extraction method to extract and separate water-soluble fucoidan sulfate and collagen fibril precipitate from the sea cucumber. The chondroitin sulfate pure product is obtained after the collagen fibril is subjected to enzymolysis and ultrafiltration deproteinization, thereby realizing the one-step completion of the extraction and separation of the fucosan sulfate and the chondroitin sulfate of the sea cucumber.
The method of the present invention is described in detail below with reference to examples and the accompanying drawings.
Example 1
1) Cutting fresh Apostichopus japonicus into 1cm pieces, weighing about 300g Stichopus japonicus body wall, adding 1.0L water, and stirring at 30 deg.C for 30 min. Then filtering with 100-mesh silk yarn, discarding the filtrate, repeatedly washing the filter residue with water twice, and combining the filter residues.
2) Adding 0.1mol/L Tris-HCl solution (pH 8.0, 4mmol/L EDTA)1.0L into the filter residue, and slowly stirring at 30 deg.C for 24 hr for extraction. Then centrifuged 7000 Xg, 30min, 4 ℃. The precipitate was washed with 200mL of distilled water, and the supernatant and the precipitate were collected.
3) Concentrating the supernatant obtained in the step 2) to 200mL in vacuum, adding cetylpyridinium chloride until the mass concentration reaches 10%, standing for 20h at 4 ℃, centrifuging for 4000 Xg for 15min, and removing the supernatant at 20 ℃ to obtain a precipitate.
The resulting precipitate was dissolved in 250mL of an ethanol solution of NaCl (3mol/L NaCl, 86% ethanol). Then, 500mL of 95% ethanol was added thereto, and the mixture was left at 4 ℃ for 12 hours. Centrifuging at 4000 Xg for 15min at 20 deg.C, removing supernatant, and collecting precipitate. The precipitate was washed 2 times with 100mL 95% ethanol. Collecting the precipitate, and freeze drying to obtain dried product of fucoidan sulfate.
4) Precipitating collagen fibrils of step 2), adding 500mL of water, adjusting pH to 8.0 with 1mol/L NaOH solution, adding 300mg of neutral protease and 300mg of alkaline protease, and hydrolyzing at 50 deg.C for 6 h. Deactivating enzyme in boiling water bath for 5min, and cooling to room temperature. Centrifuging at 5000 Xg for 20min at 50 deg.C, and collecting supernatant.
5) And (4) taking the supernatant obtained in the step 4), concentrating in vacuum, performing ultrafiltration by using an ultrafiltration membrane with the molecular weight cutoff of 10kDa, and collecting the trapped fluid with the molecular weight of more than 10 kDa. And (4) carrying out vacuum concentration and freeze drying on the trapped fluid to obtain a fucosyl chondroitin sulfate dry product.
The dried products of the fucosan sulfate and the chondroitin sulfate are weighed, and the yield of the fucosan sulfate is calculated to be 1.56 percent, and the yield of the fucosyl chondroitin sulfate oligosaccharide is calculated to be 2.83 percent.
FIGS. 1 and 2 show the molecular weights of fucoidan and fucosyl chondroitin sulfate prepared in this example measured by high performance gel exclusion chromatography. The fucoidan sulfate has a weight average molecular weight of 658.16kDa, a number average molecular weight of 351.95kDa, and a dispersion coefficient of 2.32 (FIG. 1). The fucosyl chondroitin sulfate has a weight average molecular weight of 111.07kDa, a number average molecular weight of 47.85kDa, and a dispersion coefficient of 1.87.
The sulfate content of the fucosan sulfate and the chondroitin sulfate prepared by ion chromatography detection is 26.72% and 32.28% respectively,
fig. 3, fig. 4 and table 1 show monosaccharide compositions of fucoidan sulfate and chondroitin sulfate prepared by PMP monosaccharide derivatization-high performance liquid chromatography. The prepared fucoidan sulfate contains 62.84% fucose, 8.89% galactosamine, and 6.37% galactose, and contains small amount of glucosamine, glucuronic acid and glucose; the prepared fucosyl chondroitin sulfate monosaccharide mainly contains 40.28% fucose, 16.58% galactosamine, 8.57% glucosamine, 16.58% glucuronic acid and 10.76% mannose, and meets the requirements of the composition of the sea cucumber fucosyl chondroitin sulfate monosaccharide.
Table 1: comparison table of monosaccharide compositions of fucosan sulfate and chondroitin sulfate of fresh Apostichopus japonicus
The total monosaccharide content is 100%. Man: mannose; GlcN: (ii) glucosamine; GlcA: glucuronic acid; GalN: (ii) a galactosamine; glc: glucose; gal: galactose; fuc: fucose sugar
Example 2:
1) collecting dried small Stichopus japonicus selenka (water content below 10%), pulverizing with tissue pulverizer, and sieving with 80 mesh sieve. 100g of the sample was weighed, 500mL of distilled water was added, and the mixture was extracted with stirring at 50 ℃ for 60min, and the supernatant was discarded. Leaching is repeated for 2 times, and precipitates are collected and combined.
2) The precipitate was added to 1L of 0.1mol/L Tris-HCl buffer (pH 8.0, 5mmol/L EDTA, 0.5mol/L NaCl) and stirred slowly at 50 ℃ for 24 h. Centrifuging the extractive solution at 5000 Xg for 20min at 20 deg.C. The extraction was repeated 1 more time with 500mL Tris-HCl buffer solution, and the combined supernatant and pellet were collected.
3) And (3) performing vacuum concentration, cetyl pyridine precipitation, ethanol precipitation and freeze drying on the supernatant obtained in the step 2) according to the method in the example 1 to obtain a dried product of the sea cucumber fucosan sulfate.
4) And (3) hydrolyzing the precipitate obtained in the step 2) by referring to the compound protease in the example 1, and performing ultrafiltration, desalination and deproteinization and drying to obtain a dry product of the sea cucumber chondroitin sulfate.
5) The dried products of the fucoidan sulfate and fucosyl chondroitin sulfate were weighed, and the yield of fucoidan sulfate was 1.04% and the yield of fucosyl chondroitin sulfate was 2.26% as calculated. The sulfate radical content of fucosan sulfate and chondroitin sulfate prepared by ion chromatography detection is 23.75% and 30.84% respectively, and the sulfate radical content of the compound sea cucumber sulfated polysaccharide is required.
The molecular weights of fucoidan and fucosyl chondroitin sulfate prepared in this example were determined by high performance gel exclusion chromatography. The weight-average molecular weight of the fucoidan sulfate is 602.13kDa, the number-average molecular weight is 266.43kDa, and the dispersion coefficient is 2.26. The weight-average molecular weight of the fucosyl chondroitin sulfate is 98.76kDa, the number-average molecular weight is 58.79kDa, and the dispersion coefficient is 1.68.
FIG. 3, FIG. 4 and Table 2 show the monosaccharide composition of fucoidan sulfate and chondroitin sulfate extracted from dried small Stichopus japonicus. The prepared fucosan sulfate contains fucose 61.50%, galactosamine 10.28%, galactose 5.76%, and mannose 8.24%, and contains small amount of glucosamine, glucuronic acid and glucose.
TABLE 2 comparison of monosaccharide composition of fucoidan sulfate and chondroitin sulfate of dried small Stichopus japonicus
The prepared fucosyl chondroitin sulfate monosaccharide mainly contains 38.28% of fucose, 19.18% of galactosamine, 3.75% of glucosamine, 16.72% of glucuronic acid and 10.76% of mannose, and meets the requirements of the composition of the sea cucumber fucosyl chondroitin sulfate monosaccharide.
Claims (5)
1. A method for extracting fucosan sulfate and chondroitin sulfate from sea cucumber is characterized by comprising the following steps:
1) sea cucumber pretreatment:
crushing tissue of sea cucumber, adding distilled water for leaching, centrifuging after leaching is finished, and taking precipitate for later use; wherein the mass ratio of sea water to water is 1:5-1:10, and the extraction with distilled water is carried out by stirring and extracting at 30-50 deg.C for 30-60 min;
2) aqueous solution extraction and separation:
adding Tris-HCl aqueous solution into the sediment obtained by centrifugation in the step 1) for extraction, centrifuging after extraction is finished, and collecting an extracting solution and the sediment;
the concentration of the Tris-HCl aqueous solution is 0.1-0.3mol/L, the pH value is 8.0, and the Tris-HCl aqueous solution contains 4mmol/L EDTA;
the extraction is carried out by slowly stirring and extracting for 12-24h at 30-50 ℃;
3) vacuum concentrating the extracting solution obtained in the step 2), adding cetylpyridinium chloride for precipitation, and centrifugally collecting the precipitate; dissolving the precipitate in an alcoholic solution containing NaCl; then precipitating with 90% ethanol water solution, and freeze drying to obtain dried product of fucoidan sulfate;
4) adding the precipitate obtained in the step 2) into compound protease, and carrying out enzymolysis for 3-5h in water bath at 45-60 ℃;
5) centrifuging the enzymolysis liquid obtained in the step 4), and collecting supernatant; after the supernatant fluid is concentrated in vacuum, ultrafiltration is adopted for deproteinization and desalination, and trapped fluid is collected; and concentrating and drying the trapped fluid in vacuum to obtain a fucosyl chondroitin sulfate dry product.
2. The method according to claim 1, wherein the alcoholic solution of NaCl added in 3) is 86% ethanol solution added with 3mol/L sodium chloride.
3. The method of claim 1, wherein the aqueous ethanol solution used for precipitation in 3) is a 90% aqueous ethanol solution.
4. The method according to claim 1, wherein the complex protease of 4) is a mixture of alkaline protease and trypsin.
5. The method of claim 1, wherein said ultrafiltration membrane of 5) is a 5kDa-20kDa molecular weight cut-off membrane.
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