CN103087214A - Preparation method of low-molecular-weight sea cucumber fucosan sulfate - Google Patents
Preparation method of low-molecular-weight sea cucumber fucosan sulfate Download PDFInfo
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Abstract
The invention discloses a preparation method of low-molecular-weight sea cucumber fucosan sulfate. In the preparation method, a sea cucumber polysaccharide prepared by performing enzymolysis on pulverized sea cucumbers is used as a raw material. The preparation method comprises the following steps: 1) dissolving the sea cucumber polysaccharide in a sodium chloride solution, then adding ethanol, and centrifuging to remove the precipitate, thus obtaining the supernatant; and adding ethanol into the supernatant, centrifuging, dialyzing the obtained precipitate, and performing freeze-drying to obtain sea cucumber fucosan sulfate; 2) dissolving the sea cucumber fucosan sulfate in solvent, and performing ultrasonic treatment at 0-45 DEG C, wherein the treatment time is 10-180 minutes, and the ultrasonic sound field strength is 60-800 W/cm<2>; and 3) dialyzing the treated solution obtained in the step 2), and performing vacuum freeze-drying to obtain the low-molecular-weight sea cucumber fucosan sulfate. According to the invention, an ultrasonic degradation technology is adopted, high-molecular-weight sea cucumber fucosan sulfate can be quickly degraded, the reaction conditions are mild, and the preparation method is green and environment-friendly.
Description
Technical field
The present invention relates to the preparation method of low molecular weight sea cucumber fucoidan, definite says, relates to a kind of method of utilizing ultrasonic degradation to prepare low-molecular-weight sea cucumber fucoidan.
Background technology
Sea cucumber (sea cucumber, holothurians) belong to Echinodermata (Echinodermata) Holothuroidea (Holothuroidea) Parapet hand order (Aspidocita) animal, mainly be distributed in the torrid zone and ocean, temperate zone, the sea cucumber of China's record has 101 kinds, and wherein more than 20 kinds can be edible.Sea cucumber is exactly the excellent tonic product of famous and precious medicine-food two-purpose since ancient times, ranks first of " sea ", and Traditional Chinese Medicine thinks, the sea cucumber flavor is salty, warm in nature, enters the heart, kidney channel, has tonifying kidney and benefiting sperm, enriching blood and moistening for dryness, hemostasis and anti-inflammation, and the stomach effect such as quench the thirst.Research in recent years thinks that sea cucumber is a kind of high protein, lower fat, low sugar, the heath food that does not contain cholesterol, and be rich in variously to compositions such as the useful sea cucumber polysaccharide of human body, amino acid, indispensable fatty acid, VITAMIN, mineral substance, colloid, selenkas, make sea cucumber have the effects such as antitumor, anticoagulation, raising immunizing power, reducing blood-fat, control rheumatoid arthritis and osteoarthritis.
Sea cucumber polysaccharide mainly is present in wall of sea cucumber Stichopus japonicus and discarded internal organ thereof, accounts for the 7-10% of wall of sea cucumber Stichopus japonicus, mainly is divided into two classes: sea cucumber fucoidan and fucosylation chondroitin sulfate.The sea cucumber fucoidan is the straight-chain polysaccharide that is made of L-fucose, early-stage Study shows, separate from a kind of U.S. meat ginseng and obtain fucoidan, be the repeating unit formation of [→ 3Fuc (2S, 4S) α 1 → 3Fuc (2S) α 1 → 3Fuc (2S) α 1 → 3Fuc α 1 →] n through resolving its structure.The sea cucumber fucoidan has multiple biological activity, comprises anti-oxidant, anticoagulation, inhibition tumour, reducing blood-fat, raising immunizing power, anti-inflammatory, stomach protection, antivirus action etc.
The sea cucumber fucoidan has many activity, but because its molecular weight is larger, the utilization that is difficult for being absorbed by the body, thereby be restricted in research with aspect utilizing.The advantage such as viscosity is low owing to having for the low molecular weight sea cucumber fucoidan, easy absorption, bioavailability are good shows than the better biological activity of macromolecular polysaccharide.The degraded of polysaccharide and low molecular weight product thereof are very extensive in exploitation and the application in the fields such as healthcare products, medicine, foodstuff additive, and degradation method commonly used mainly contains chemical degradation method, biological degradation method and mechanical degradation method at present.The method of the degraded fucoidan of bibliographical information concentrates on chemical degradation method mostly at present, although chemical method is swift in response, reaction is violent, and is larger to polysaccharide structures destruction, and product molecular weight distribution is wide.Although the biological degradation method reaction temperature and, specificity is high, can be applicable to polysaccharide, especially single-minded enzyme for fucoidan degraded is very rare, and reaction conditions harshness comparatively, cost is high, industrialized production has certain difficulty.The mechanical degradation method is due to little to its lytic activity structure deteriorate, molecular weight is easy to control, reaction efficiency is high and become a kind of desirable degradation method, polysaccharose substance mechanical degradation method commonly used has ultrasonic degradation, irradiation-induced degradation, microwave degradation etc., wherein irradiation-induced degradation is most effective, to studies show that of konjak glucomannan, after 5.0kGy and 100.0kGy irradiation, molecular weight of product is down to respectively 370kDa and 39.8kDa by 481kDa, but because radiation treatment is destroyed very violent to molecular structure, and security is still disputable, so its application is restricted.
(Chinese Sea medicine the 30 3 phases of volume in 2011 are studied the comparison of rat fat liver improvement effect and the characteristic of digesting and assimilating of different molecular weight sea cucumber fucoidan different molecular weight sea cucumber fucoidan in 20-24) Wu Xiaolin at " molecular weight active on the sea cucumber fucoidan and the impact research of digesting and assimilating " and " preparation of different molecular weight sea cucumber fucoidan and digest and assimilate the preliminary study of characteristic ".
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation method of low molecular weight sea cucumber fucoidan, the present invention utilizes the ultrasonic degradation technology, degraded macromolecular amount sea cucumber fucoidan rapidly, and reaction conditions is gentle, simple to operate, environmental protection.
In order to solve the problems of the technologies described above, the invention provides a kind of preparation method of low molecular weight sea cucumber fucoidan, to utilize sea cucumber polysaccharide that enzymolysis process obtained as raw material after will sea cucumber pulverizing, comprise the following steps:
1), sea cucumber polysaccharide be dissolved in 2.8 ~ 3.2mol/L(be preferably 3mol/L) sodium chloride solution (for strong brine) in, get sea cucumber polysaccharide solution, in sea cucumber polysaccharide solution, the mass concentration of sea cucumber polysaccharide is that 0.8 ~ 1.2%(is preferably 1%);
Add ethanol in sea cucumber polysaccharide solution, until the volume final concentration of ethanol is 34 ~ 40%, the centrifugal precipitation of removing gets supernatant liquor;
Add ethanol in supernatant liquor, centrifugal until the volume final concentration of ethanol is 60 ~ 90%, the precipitation of gained obtains the sea cucumber fucoidan after dialysis and lyophilize;
2), the sea cucumber fucoidan is dissolved in solvent carries out supersound process at the temperature of 0 ~ 45 ℃ (being preferably 5 ~ 35 ℃), the treatment time is that 10 ~ 180min(is preferably 10 ~ 80 min), ultrasonic sound field intensity is 60 ~ 800W/cm
2(be preferably 180 ~ 550 W/cm
2); Ultrasonic frequency is 21 ~ 25kHz;
3), with step 2) solution dialysis after the processing of gained, after vacuum lyophilization, get the low molecular weight sea cucumber fucoidan.
Improvement as the preparation method of low molecular weight sea cucumber fucoidan of the present invention: the molecular weight cut-off of the dialysis tubing that the dialysis in step 1) is used is 8000kDa.
Further improvement as the preparation method of low molecular weight sea cucumber fucoidan of the present invention: step 2) solvent is that deionized water, mass concentration are that 0.5 ~ 5% acetum, mass concentration are that 0.5 ~ 5% hydrochloric acid soln or mass concentration are 0.5 ~ 5% sulphuric acid soln.
Further improvement as the preparation method of low molecular weight sea cucumber fucoidan of the present invention: step 2), the solid-liquid ratio of sea cucumber fucoidan and solvent is 1g/20-200ml.Be 1g sea cucumber fucoidan adapted 20-200ml solution.Better solid-liquid ratio is 1g/50-70ml.
Further improvement as the preparation method of low molecular weight sea cucumber fucoidan of the present invention: the molecular weight cut-off of the dialysis tubing that the dialysis in step 3) is used is 1000kDa.
Further improvement as the preparation method of low molecular weight sea cucumber fucoidan of the present invention:
Step 2) be: 0.5g sea cucumber fucoidan is dissolved in carries out supersound process in the 30ml deionized water at the temperature of 13.0713 ℃, the treatment time is 80min, and ultrasonic sound field intensity is 508.28W/cm
2
Further improvement as the preparation method of low molecular weight sea cucumber fucoidan of the present invention:
Step 2) be: the mass concentration that 0.5g sea cucumber fucoidan is dissolved in 30ml is that the mass concentration of 2% acetic acid, 30ml is that the mass concentration of 2% hydrochloric acid or 30ml is to carry out supersound process in 2% sulfuric acid at the temperature of 13.0713 ℃, treatment time is 40min, and ultrasonic sound field intensity is 508.28W/cm
2
The technical solution adopted in the present invention is to utilize the sea cucumber polysaccharide that enzymolysis process obtained after will sea cucumber to pulverize (this is as known technology, for example can be prepared according to the enzymolysis process of delivering in containing gentle and quiet Master's thesis " different sea cucumber polysaccharides extract separation and chemical composition analysis compares ") obtain the sea cucumber fucoidan as raw material, break glycosidic link by supersound process and obtain the low molecular weight sea cucumber fucoidan.
Compared with prior art, outstanding advantages of the present invention is:
1, use physical method to break glycosidic link, degraded sea cucumber fucoidan, little to product structure destruction, without side reaction, noresidue material, molecular weight are easy to control;
2, preparation process is simple, and is with low cost, and reaction efficiency is high, pollution-free;
3, overcome the destruction of in the past using in chemical process degradation of polysaccharide process product structure;
4, according to prior art as can be known: gained low molecular weight sea cucumber fucoidan of the present invention has good removing free radical ability and anticoagulant active, and be easily absorbed by the body, can be applicable to the preparation of healthcare products, functional food or the medicine of antithrombotic, anticoagulation, inhibition tumour, strengthening immunity, have high society, economic implications and application potential.
Embodiment
The preparation method of embodiment 1-1, a kind of low molecular weight sea cucumber fucoidan, to utilize sea cucumber polysaccharide that enzymolysis process obtained as raw material after will sea cucumber pulverizing, carry out following steps successively:
1), sea cucumber polysaccharide is dissolved in the sodium chloride solution (strong brine) of 3mol/L, get sea cucumber polysaccharide solution, in sea cucumber polysaccharide solution, the mass concentration of sea cucumber polysaccharide is 1%;
Add ethanol in sea cucumber polysaccharide solution, until the volume final concentration of ethanol is 37%, centrifugal (6000r/min, 15min) removes precipitation, gets supernatant liquor;
Add ethanol in described supernatant liquor, until the volume final concentration of ethanol is 75%, centrifugal (6000r/min, 15min), the precipitation of gained through dialysis (cross molecular weight cut-off be the dialysis tubing of 8000kDa) and lyophilize (in-45 ℃, the dry 40h of vacuum tightness 0.1Mpa) after, obtain the sea cucumber fucoidan.
2), 0.5g sea cucumber fucoidan is dissolved in carries out supersound process in the 30ml deionized water at the temperature of 5 ℃, the treatment time is 10min, ultrasonic sound field intensity is 181.53 W/cm
2This moment, ultrasonic frequency more was the explanation of 21-25kHz(remarks: instrument is regulated in this scope voluntarily).
3), with step 2) solution dialysis (crossing interception is the dialysis tubing of 1000kDa) after the processing of gained, after vacuum lyophilization (in the vacuum tightness of 0.1Mpa ,-45 ℃ of dry 40h), get the approximately low molecular weight sea cucumber fucoidan of 0.38g.
Adopt gel permeation chromatography to detect molecular weight of product the low molecular weight sea cucumber fucoidan of above-described embodiment 1-1 gained, its molecular weight (kDa) is 217.48.
Embodiment 1-2 ~ 1-5,
For verification step 2) in different ultrasonic sound field intensity carry out ultrasonic degradation to preparation and the impact of low molecular weight sea cucumber fucoidan, change step 2) in ultrasonic sound field intensity, all the other are with embodiment 1-1, thereby obtain embodiment 1-2 ~ 1-5; The low molecular weight sea cucumber fucoidan molecular weight of concrete ultrasonic sound field intensity and corresponding gained is as shown in table 1.
Table 1, different ultrasonic sound field intensity gained low molecular weight sea cucumber fucoidan molecular weight
Can be found by table 1, ultrasonic sound field intensity is 181.53-544.59 W/cm
2The time, after effect 10min, along with the increase of ultrasonic sound field intensity, sea cucumber fucoidan molecular weight constantly reduces, and concentrates on 138.47-217.48kDa.When ultrasonic sound field intensity was 544.59, sea cucumber fucoidan molecular weight was down to 138.47kDa by 547.11kDa.In this sound field scope, ultrasonic degradation sea cucumber fucoidan effect is remarkable.
Embodiment 2-1 ~ 2-3,
For verification step 2) in carry out ultrasonic degradation to preparation at the differential responses temperature and the impact of low molecular weight sea cucumber fucoidan, the step 2 of change embodiment 1-4) temperature of reaction in, all the other are with embodiment 1-4, thereby obtain embodiment 2-1 ~ 2-3(namely, treatment time is 10min, and ultrasonic sound field intensity is 423.57 W/cm
2); The low molecular weight sea cucumber fucoidan molecular weight of concrete temperature of reaction and corresponding gained is as shown in table 2.
Table 2, differential responses temperature gained low molecular weight sea cucumber fucoidan molecular weight
| Embodiment 1-4 | Embodiment 2-1 | Embodiment 2-2 | Embodiment 2-3 | |
| Temperature of reaction (℃) | 5 | 15 | 25 | 35 |
| Molecular weight (kDa) | 141.72 | 139.06 | 152.36 | 173.43 |
Can be found by table 2, when temperature of reaction is 5-45 ℃, after ultrasonication 10min, on the whole, degraded trend strengthens along with the reduction of temperature, and sea cucumber fucoidan molecular weight concentrates on 139.06-212.97kDa, when temperature was 15 ℃, molecular weight was minimum, was 139.06kDa.In this temperature range, ultrasonic degradation sea cucumber fucoidan effect is remarkable.
Embodiment 3, on the basis of above-described embodiment, the response Surface Analysis is optimized low molecular weight sea cucumber fucoidan ultrasonic degradation condition, carries out following steps:
Get 0.5g sea cucumber fucoidan and be dissolved in the 30ml deionized water, the ultrasonication time is 10min, selection has 2 factors (temperature of reaction, ultrasonic sound field intensity) of remarkably influenced to carry out the response surface test on peak molecular weight, thereby optimizes the condition of ultrasonic degradation fucoidan.
Adopt Minitab data system analysis software to carry out regression analysis to testing data.Use response surface central composite design method (central composite design, CCD) design 2 factor 3 hydraulic tests, the basic, normal, high test water of each independent variable(s) is not divided equally and is encoded with-1,0,1, experimental design and the results are shown in Table 3.Utilize Minitab his-and-hers watches 3 testing datas to carry out the multiple regression match, obtain fucoidan retention time (Y) to temperature of reaction (X
1), ultrasonic power (X
2) secondary multiple regression simulation equation be:
Y=59.4595+?8.24809X
1+5.48866X
2+0.139715X
1 2-0.0775104X
2 2?-0.283303X
1X
2
Table 3, CCD response curved surface test design and result
Response curved surface result is carried out variance analysis, find model P＜0.01, model returns highly significant; Lose and intend a P=0.285 0.05, not remarkable, illustrate that in selected two factor range of test, the gained model can reflect true relation between parameter; R
2=0.9328 show this model and the actual tests match better.By regression model coefficient test of significance result as can be known, an once X of model
1(temperature of reaction), X
2(ultrasonic sound field intensity) is all remarkable to the degraded of sea cucumber fucoidan, wherein X
1(P＜0.001), very remarkable; Quadratic term is all not remarkable, and a mutual X
1X
2(P＜0.05) is remarkable to Degradation.To model by analysis, obtain optimum parameter: temperature: 13.1398 ℃, sound field intensity: 508.28W.cm
2
Embodiment 4,
For verification step 2) in carry out ultrasonic degradation to preparation under the different ultrasonication time and the impact of low molecular weight sea cucumber fucoidan, with the step 2 of embodiment 1-1) make following content into, all the other are with embodiment 1-1:
2), 0.5g sea cucumber fucoidan is dissolved in carries out supersound process in the 30ml deionized water at the temperature of 13.0713 ℃, the treatment time is 2.5min(or is 0 min, 5min, 20min, 40min, 80min), ultrasonic sound field intensity is 508.28W/cm
2
The low molecular weight sea cucumber fucoidan molecular weight of gained is as shown in table 4.
Table 4, different gained low molecular weight sea cucumber fucoidan molecular weight action time (embodiment 4)
Can be found by table 4, in 20min, molecular weight and molecular weight is very rapid before supersound process, especially front 5min, and molecular weight drops to 140.97kDa from 547.11kDa, and degradation efficiency is very high; After surpassing 20min, along with the prolongation of ultrasonic time, molecular weight and molecular weight tends towards stability.After processing 80min, molecular weight is down to 78.92kDa.
Embodiment 5,
For verification step 2) in carry out ultrasonic degradation to preparation under different solvents and the impact of low molecular weight sea cucumber fucoidan, with the step 2 of embodiment 1-1) make following content into, all the other are with embodiment 1-1:
2) mass concentration that, 0.5g sea cucumber fucoidan is dissolved in 30ml is to carry out supersound process in 2% acetic acid (being perhaps that 2% hydrochloric acid, mass concentration are 2% sulfuric acid for mass concentration) at the temperature of 13.0713 ℃, treatment time is that 40min(is, the ultrasonication time is 40min), ultrasonic sound field intensity is 508.28W/cm
2
The low molecular weight sea cucumber fucoidan molecular weight of gained is as shown in table 5.
Table 5, differential responses solvent gained low molecular weight sea cucumber fucoidan molecular weight
| Solvent | Acetic acid (2%) | Hydrochloric acid (2%) | Sulfuric acid (2%) |
| Molecular weight (kDa) | 79.68 | 77.53 | 81.60 |
Can be found by table 5, acetic acid, hydrochloric acid and sulfuric acid with lower concentration replace deionized water, ultrasonic degradation there is the aggravation effect, after ultrasonication 40min, molecular weight is down near 80kDa, uses different types of acid to carry out ultrasonic degradation sea cucumber fucoidan effect as reaction solvent remarkable.
At last, it is also to be noted that, what more than enumerate is only several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (8)
1. the preparation method of low molecular weight sea cucumber fucoidan to utilize sea cucumber polysaccharide that enzymolysis process obtained as raw material after will sea cucumber pulverizing, is characterized in that comprising the following steps:
1), sea cucumber polysaccharide is dissolved in the sodium chloride solution of 2.8 ~ 3.2mol/L, get sea cucumber polysaccharide solution, in described sea cucumber polysaccharide solution, the mass concentration of sea cucumber polysaccharide is 0.8 ~ 1.2%;
Add ethanol in described sea cucumber polysaccharide solution, until the volume final concentration of ethanol is 34 ~ 40%, the centrifugal precipitation of removing gets supernatant liquor;
Add ethanol in described supernatant liquor, centrifugal until the volume final concentration of ethanol is 60 ~ 90%, the precipitation of gained obtains the sea cucumber fucoidan after dialysis and lyophilize;
2), the sea cucumber fucoidan is dissolved in carries out supersound process in solvent at the temperature of 0 ~ 45 ℃, the treatment time is 10 ~ 180min, ultrasonic sound field intensity is 60 ~ 800W/cm
2
3), with step 2) solution dialysis after the processing of gained, after vacuum lyophilization, get the low molecular weight sea cucumber fucoidan.
2. the preparation method of low molecular weight sea cucumber fucoidan according to claim 1, it is characterized in that: the molecular weight cut-off of the dialysis tubing that the dialysis in described step 1) is used is 8000kDa.
3. the preparation method of low molecular weight sea cucumber fucoidan according to claim 2 is characterized in that: described step 2) solvent is that deionized water, mass concentration are that 0.5 ~ 5% acetum, mass concentration are that 0.5 ~ 5% hydrochloric acid soln or mass concentration are 0.5 ~ 5% sulphuric acid soln.
4. the preparation method of low molecular weight sea cucumber fucoidan according to claim 3 is characterized in that: described step 2), the solid-liquid ratio of sea cucumber fucoidan and solvent is 1g/20 ~ 200ml.
5. the preparation method of low molecular weight sea cucumber fucoidan according to claim 4, it is characterized in that: the molecular weight cut-off of the dialysis tubing that the dialysis in described step 3) is used is 1000kDa.
6. the preparation method of low molecular weight sea cucumber fucoidan according to claim 5 is characterized in that:
Described step 2) in: temperature is 5 ~ 35 ℃, and the treatment time is 10 ~ 80min, and ultrasonic sound field intensity is 180 ~ 550W/cm
2
7. the preparation method of low molecular weight sea cucumber fucoidan according to claim 6 is characterized in that:
Step 2) be: 0.5g sea cucumber fucoidan is dissolved in carries out supersound process in the 30ml deionized water at the temperature of 13.0713 ℃, the treatment time is 80min, and ultrasonic sound field intensity is 508.28W/cm
2
8. the preparation method of low molecular weight sea cucumber fucoidan according to claim 6 is characterized in that:
Step 2) be: the mass concentration that 0.5g sea cucumber fucoidan is dissolved in 30ml is that the mass concentration of 2% acetic acid, 30ml is that the mass concentration of 2% hydrochloric acid or 30ml is to carry out supersound process in 2% sulfuric acid at the temperature of 13.0713 ℃, treatment time is 40min, and ultrasonic sound field intensity is 508.28W/cm
2
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| CN104610459A (en) * | 2014-09-17 | 2015-05-13 | 中国海洋大学 | Low molecular weight imitated stichopus japonicus selenka glycosaminoglycans, preparation method, and applications thereof |
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| CN106866834A (en) * | 2017-03-16 | 2017-06-20 | 山东省食品发酵工业研究设计院 | It is a kind of to prepare the efficiently method of the fucoidin of customization molecular weight and its application |
| CN109705232A (en) * | 2018-12-28 | 2019-05-03 | 金耀仑 | A kind of extraction process of low-molecular-weight algal carbohydrate gum and its application in cosmetics |
| CN110357983A (en) * | 2019-08-14 | 2019-10-22 | 中国海洋大学 | A kind of preparation method of sea cucumber fucoidan and chondroitin sulfate oligosaccharide |
| CN111548427A (en) * | 2019-02-12 | 2020-08-18 | 湖北洪森生物科技有限公司 | Preparation method of high-activity rice polysaccharide powder |
| CN111713654A (en) * | 2020-07-27 | 2020-09-29 | 大连工业大学 | Leisure food containing polysaccharide and fishbone calcium and preparation method thereof |
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| CN104710539A (en) * | 2013-12-17 | 2015-06-17 | 深圳海王药业有限公司 | Sulfate fucosan and preparation method thereof |
| CN104710539B (en) * | 2013-12-17 | 2017-07-07 | 深圳海王医药科技研究院有限公司 | fucoidan and preparation method thereof |
| CN104610459A (en) * | 2014-09-17 | 2015-05-13 | 中国海洋大学 | Low molecular weight imitated stichopus japonicus selenka glycosaminoglycans, preparation method, and applications thereof |
| CN106866834A (en) * | 2017-03-16 | 2017-06-20 | 山东省食品发酵工业研究设计院 | It is a kind of to prepare the efficiently method of the fucoidin of customization molecular weight and its application |
| CN106866834B (en) * | 2017-03-16 | 2018-01-30 | 山东省食品发酵工业研究设计院 | A kind of method and its application for preparing the efficiently fucoidin of customization molecular weight |
| CN109705232A (en) * | 2018-12-28 | 2019-05-03 | 金耀仑 | A kind of extraction process of low-molecular-weight algal carbohydrate gum and its application in cosmetics |
| CN111548427A (en) * | 2019-02-12 | 2020-08-18 | 湖北洪森生物科技有限公司 | Preparation method of high-activity rice polysaccharide powder |
| CN110357983A (en) * | 2019-08-14 | 2019-10-22 | 中国海洋大学 | A kind of preparation method of sea cucumber fucoidan and chondroitin sulfate oligosaccharide |
| CN111713654A (en) * | 2020-07-27 | 2020-09-29 | 大连工业大学 | Leisure food containing polysaccharide and fishbone calcium and preparation method thereof |
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