CN107011454B - A kind of sea cucumber fucoidan preparation method of the high sulphation of low molecular weight - Google Patents
A kind of sea cucumber fucoidan preparation method of the high sulphation of low molecular weight Download PDFInfo
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Abstract
The invention discloses a kind of sea cucumber fucoidan preparation methods of the high sulphation of low molecular weight, first using sea cucumber fucoidan as raw material, glycosidic bond is broken using ultrasonic-microwave combined degradation method, it decomposes sea cucumber fucoidan and low-molecular-weightsea sea cucumber fucosan sulfate is made, then methyl methylsulfonate and low-molecular-weightsea sea cucumber fucosan sulfate is selected to carry out the sea cucumber fucoidan preparation method that the high sulphation of low molecular weight is made in sulfuric acid esterification.Reaction cost of the present invention is lower, and preparation process is simple, and reaction efficiency is higher, it is pollution-free, small, no side reaction is destroyed to product structure, reaction is mild controllable, molecular weight product obtained is low, and sulfate radical content is high, has stronger bioactivity, with anti-oxidant, hypoglycemic, reducing blood lipid and other effects, and more conducively absorption of human body, it can be applied to the industries such as corresponding health care product, functional food or medical formula food, there is high society, economic significance and application potential.
Description
Technical field
The present invention relates to technical field of biological extraction, more particularly, to a kind of sea cucumber fucan of the high sulphation of low molecular weight
Sugar sulfate preparation method.
Background technique
Sea cucumber is a kind of traditional integration of drinking and medicinal herbs invigorant in China, in global 1100 kinds of sea cucumber, edible sea cucumber
More than 20 are only accounted for, the overwhelming majority is inedible low value sea cucumber.Wall of sea cucumber Stichopus japonicus is the main edible or medicinal part of sea cucumber.?
In dried sea-cucumber, the content of protein is up to 85-90% or so, and lipid accounts for about 4%, and polysaccharide accounts for about 6-10%, in addition also containing calcium, iron,
The microelements such as zinc, manganese, selenium, molybdenum.It is widely used in the list of Chinese medicine in wall of sea cucumber Stichopus japonicus due to containing several physiological active substances
In side or compound prescription and herbal cuisine or diet therapy formulation, such as collagen, sulfated polysaccharide, saponin(e, sterol, active lipids.
Sulfated polysaccharide is the important component of wall of sea cucumber Stichopus japonicus.The sulfated polysaccharide being proved in wall of sea cucumber Stichopus japonicus at present mainly has two
Kind: fucoidan and fucosylation chondroitin sulfate, wherein sea cucumber fucoidan is one kind mainly by L-
The straight chain sulfated polysaccharide of fucose composition.Being proved sea cucumber fucoidan has significant antitumor, antithrombotic, drop blood
Sugar, reducing blood lipid, the effect for improving insulin resistance, Liver protection and kidney protection.The bioactivity of fucoidan is changed with it
It learns structure and physicochemical property is closely related, under normal circumstances, in certain molecular weight ranges, molecular weight is lower, bioactivity
It is stronger.Sea cucumber fucoidan molecular weight is larger, by taking Haiti melon and plum blossom ginseng as an example, both sea cucumber sulfated fucans
Ester molecule amount is up to 1614kDa and 1284kDa respectively, and the fucoidan of high molecular weight is difficult to be absorbed by small intestine cells
Enter systemic circulatory system, be degraded to the fucoidan of low molecular weight more when utilizing, have low viscosity, easy absorption and
The high feature of bioavailability, and bioactivity is stronger.In addition, the content of sulfate radical is also living to the biology of fucoidan
Property have direct influence, sulfate radical content is higher, and bioactivity is stronger, and foreign countries also have related by increasing sulfate radical content enhancing
The report of fucoidan bioactivity is shown in paper " Oversulfation of fucoidan enhances its
Anti-angiogenic and antitumor activities " (Biochemical Pharmacology 2003 the 65th
Roll up 2 phases, 173-179).
Have some reports about preparation low-molecular-weightsea sea cucumber fucosan sulfate currently, domestic, such as patent is " low
The preparation method of molecular weight sea cucumber fucoidan ", patent No. CN103087214A, this method are sharp after being crushed with sea cucumber
Obtaining sea cucumber fucoidan with enzymatic isolation method is raw material, breaks glycosidic bond by ultrasonic treatment and obtains low molecular weight sea cucumber rock
Algae glycan sulfuric ester, this method rapid reaction is small to product structure destruction, but due to reacting too fast point for being easy to cause product
Son amount is too low and makes sea cucumber fucoidan activity limited.Such as patent " fucoidan and its preparation side again
Method ", patent No. CN104710539A, this method are using echinoderm as raw material, and enzymatic hydrolysis alcohol deposition method obtains fucoidan,
Low molecular weight fucoidan sulfuric ester is obtained using peroxide degradation method or acid degradation method, this method is because of the peroxide using higher concentration
Compound or acid degrade to fucoidan, and method is more violent, and reaction is not easy to control, destructive to polysaccharide molecule structure
It is larger.Such as " a method of extraction prepares low molecule fucoidan from yellow tang " again, the patent No.
CN103788219A, this method are directly to carry out separation of polysaccharides and degradation to it using hydrochloric acid, then through alcohol using yellow tang as raw material
Low molecular weight fucoidan is obtained after heavy, this method reaction is more violent, and because of the extraction of fucoidan and
Degradation is combined into a step, can not control to the molecular weight control of fucoidan.For oversulfated fucoidan
Preparation, only there are a relevant document report in foreign countries, and domestic still belong to blank field.Foreign countries' report is to utilize dimethylformamide
It is prepared oversulfated with vulcanization reaction occurs with fucoidan under trimethyl ammonium sulfur trioxide copolymer collective effect
The product sulfur acidification of fucoidan, this method preparation is horizontal higher, but trimethyl ammonium sulfur trioxide copolymer price is high
It is expensive, it is unfavorable for industrialized production.
Summary of the invention
The present invention is to solve present in the low-molecular-weightsea sea cucumber fucosan sulfate preparation method of the prior art
The above problem, it is simple to provide a kind of processing step, and reaction is mild, destroys small, no side reaction to product structure, reaction efficiency compared with
Height, the sea cucumber fucoidan preparation method of the free of contamination high sulphation of low molecular weight.
To achieve the goals above, the invention adopts the following technical scheme:
A kind of sea cucumber fucoidan preparation method of the high sulphation of low molecular weight, comprising the following steps:
(1) sea cucumber fucoidan is soluble in water, first time ultrasonic treatment is carried out at a temperature of 30 ~ 40 DEG C.This
Sea cucumber fucoidan employed in invention is that enzymatic hydrolysis alcohol deposition method sea cucumber rock algae obtained is utilized after crushing sea cucumber
Glycan sulfuric ester, this method are the conventional method of this field, and therefore, not repeat them here.
(2) microwave treatment is carried out at a temperature of 60 ~ 80 DEG C to the sea cucumber fucoidan solution in step (1).
(3) the sea cucumber fucoidan solution in step (2) is carried out at a temperature of 40 ~ 50 DEG C at second of ultrasound
Reason, acquired solution obtain low-molecular-weightsea sea cucumber fucosan sulfate after dialysis, vacuum freeze drying.
(4) low-molecular-weightsea sea cucumber fucosan sulfate is dissolved in dimethylformamide, K is added2CO3, it mixes, then plus
Enter excessive methyl methylsulfonate, carries out sulfuric acid esterification under agitation, obtain reaction solution.Potassium carbonate can provide potassium from
Son, has catalytic action, and the stabilization of pH when potassium carbonate also ensures reaction sufficiently carries out convenient for reaction.
(5) it mixes well, stands after ethyl acetate being added in reaction solution, centrifuge separation is precipitated through 70% ethanol solution
It is multiple soluble in water after cleaning, through dialysing, vacuum freeze drying to get the high sulphation of low molecular weight sea cucumber sulfated fucan
Ester.
Preferably, in step (1), the technological parameter of first time ultrasonic treatment are as follows: ultrasonic sound field intensity is 40 ~ 50W/
cm2, supersonic frequency is 20 ~ 25kHz, 10 ~ 15min of ultrasonic time.First time ultrasound intensity is small, is pretreatment, the purpose is to broken
Anastomosis between bad cell.
Preferably, in step (2), the technological parameter of microwave treatment are as follows: 400 ~ 600W of microwave power, the microwave time 5 ~
15min。
Preferably, in step (3), the technological parameter of second of ultrasonic treatment are as follows: ultrasonic sound field intensity is 100 ~ 300W/
cm2, supersonic frequency is 20 ~ 25kHz, 30 ~ 60min of ultrasonic time.Second of ultrasound intensity is big, is formal extraction experiment, mesh
Be open glycosidic bond.
Preferably, in step (3), low-molecular-weightsea sea cucumber fucosan sulfate and K2CO3Mass ratio be 1:(1.2 ~
1.4).
Preferably, in step (4), 50 ~ 70 DEG C of the reaction temperature of sulfuric acid esterification, 4 ~ 8h of reaction time.Esterification temperature
For degree in 50 ~ 60 DEG C of variations, products therefrom sulfate radical content is in increase trend, and esterification temperature is in 60 ~ 70 DEG C of variations, the product sulfur
Acid group content is basically unchanged；For reaction time of esterification when 4 ~ 6h changes, products therefrom sulfate radical content is in increase trend, in 6 ~ 8h
When variation, products therefrom sulfate radical content is held essentially constant.Therefore the present invention in strict control sulfuric acid esterification reaction
50 ~ 70 DEG C of temperature, 4 ~ 8h of reaction time.
Preferably, using the strong illumination of 55 ~ 100W during sulfuric acid esterification.It can promote to react by illumination,
Under the illumination of 55 ~ 100W, product sulfate radical content is higher.
Preferably, the ethyl acetate of 10 times of volumes is added in reaction solution in step (5).
Preferably, time of repose is 2 ~ 3h.
Preferably, centrifuging process parameter are as follows: 3500 ~ 4500r/min of centrifugal rotational speed, 10 ~ 15min of centrifugation time.
Therefore, the invention has the following beneficial effects:
(1) using sea cucumber fucoidan as raw material, glycosidic bond is broken using ultrasonic-microwave combined degradation method, point
Sea cucumber fucoidan is solved, small, no side reaction is destroyed to product structure, reaction is mild, and sea cucumber fucoidan is not
Easy excessive degradation and keep molecular weight too low, easily controllable molecular size range；
(2) methyl methylsulfonate and low-molecular-weightsea sea cucumber fucosan sulfate is selected to carry out sulfuric acid esterification, reaction
Cost is relatively low, and preparation process is simple, and reaction efficiency is higher, pollution-free；
(3) final products molecular weight is low, and sulfate radical content is high, has stronger bioactivity, has anti-oxidant, drop blood
Sugar, reducing blood lipid and other effects, and more conducively absorption of human body, can be applied to corresponding health care product, functional food or medical formula food
Etc. industries, have high society, economic significance and application potential.
Specific embodiment
Below by specific embodiment, the present invention will be further described.
Embodiment 1
(1) 1g sea cucumber fucoidan is dissolved in 50ml water, first time ultrasonic treatment is carried out at a temperature of 30 DEG C,
The technological parameter of ultrasonic treatment for the first time are as follows: ultrasonic sound field intensity is 40W/cm2, supersonic frequency 20kHz, ultrasonic time
10min；
(2) microwave treatment carried out at a temperature of 60 DEG C to the sea cucumber fucoidan solution in step (1), at microwave
The technological parameter of reason are as follows: microwave power 400W, microwave time 5min；
(3) second is carried out at a temperature of 40 DEG C to the sea cucumber fucoidan solution in step (2) to be ultrasonically treated,
Acquired solution through molecule interception be 1000kDa bag filter dialysis, vacuum freeze drying (in 0.1Mpa vacuum degree, -45
DEG C dry 48h) after, 0.87g low-molecular-weightsea sea cucumber fucosan sulfate is obtained, the technological parameter of second of ultrasonic treatment are as follows: super
Several field intensities are 100W/cm2, supersonic frequency 20kHz, ultrasonic time 30min；By resulting low molecular weight sea cucumber fucan
Sugar sulfate detects molecular weight of product using gel permeation chromatography, and molecular weight is 252.6kDa(original sea cucumber fucosan sulphur
Acid ester molecules amount is 1614.1kDa)；
(4) it takes 0.5g low-molecular-weightsea sea cucumber fucosan sulfate and is dissolved in 8ml dimethylformamide, by low point
Son amount sea cucumber fucoidan and K2CO3Mass ratio be 1:1.2 proportion be added 0.6gK2CO3It mixes, adds excess
Methyl methylsulfonate, carry out sulfuric acid esterification under agitation, 50 DEG C of the reaction temperature of sulfuric acid esterification, when reaction
Between 4h, obtain reaction solution, the strong illumination of 55W used during sulfuric acid esterification；
(5) it is mixed well after the ethyl acetate of 10 times of volumes is added in reaction solution, stands 2h, be centrifugated, from
The heart revolving speed 3500r/min, centrifugation time 10min, precipitating is multiple soluble in water after the cleaning of 70% ethanol solution, through molecule interception
It dialyses for the bag filter of 50kDa, vacuum freeze drying (vacuum degree, -45 DEG C of dry 48h in 0.1Mpa) is low to get 0.56g
The sea cucumber fucoidan of the high sulphation of molecular weight.
The sea cucumber fucoidan of the high sulphation of resulting low molecular weight is used into sulfate by ion chromatography the product sulfur
Acid group content, sulfate radical content are 26.3%) 40.1%(original sea cucumber fucoidan sulfate radical content is.
Embodiment 2
(1) 1g sea cucumber fucoidan is dissolved in 50ml water, first time ultrasonic treatment is carried out at a temperature of 40 DEG C,
The technological parameter of ultrasonic treatment for the first time are as follows: ultrasonic sound field intensity is 50W/cm2, supersonic frequency 25kHz, ultrasonic time
15min；
(2) microwave treatment carried out at a temperature of 80 DEG C to the sea cucumber fucoidan solution in step (1), at microwave
The technological parameter of reason are as follows: microwave power 600W, microwave time 15min；
(3) second is carried out at a temperature of 50 DEG C to the sea cucumber fucoidan solution in step (2) to be ultrasonically treated,
Acquired solution through molecule interception be 1000kDa bag filter dialysis, vacuum freeze drying (in 0.1Mpa vacuum degree, -45
DEG C dry 48h) after, 0.85g low-molecular-weightsea sea cucumber fucosan sulfate is obtained, the technological parameter of second of ultrasonic treatment are as follows: super
Several field intensities are 300W/cm2, supersonic frequency 25kHz, ultrasonic time 60min；By resulting low molecular weight sea cucumber fucan
Sugar sulfate detects molecular weight of product using gel permeation chromatography, and molecular weight is 254.8kDa(original sea cucumber fucosan sulphur
Acid ester molecules amount is 1614.1kDa)；
(4) it takes 0.5g low-molecular-weightsea sea cucumber fucosan sulfate and is dissolved in 8ml dimethylformamide, by low point
Son amount sea cucumber fucoidan and K2CO3Mass ratio be 1:1.4 proportion be added 0.7gK2CO3It mixes, adds excess
Methyl methylsulfonate, carry out sulfuric acid esterification under agitation, 70 DEG C of the reaction temperature of sulfuric acid esterification, when reaction
Between 8h, obtain reaction solution, the strong illumination of 100W used during sulfuric acid esterification；
(5) it is mixed well after the ethyl acetate of 10 times of volumes is added in reaction solution, stands 3h, be centrifugated, from
The heart revolving speed 4500r/min, centrifugation time 15min, precipitating is multiple soluble in water after the cleaning of 70% ethanol solution, through molecule interception
It dialyses for the bag filter of 50kDa, vacuum freeze drying (vacuum degree, -45 DEG C of dry 48h in 0.1Mpa) is low to get 0.52g
The sea cucumber fucoidan of the high sulphation of molecular weight.
The sea cucumber fucoidan of the high sulphation of resulting low molecular weight is used into sulfate by ion chromatography the product sulfur
Acid group content, sulfate radical content are 26.3%) 43.3%(original sea cucumber fucoidan sulfate radical content is.
Embodiment 3
(1) 1g sea cucumber fucoidan is dissolved in 50ml water, first time ultrasonic treatment is carried out at a temperature of 35 DEG C,
The technological parameter of ultrasonic treatment for the first time are as follows: ultrasonic sound field intensity is 45W/cm2, supersonic frequency 22kHz, ultrasonic time
12min；
(2) microwave treatment carried out at a temperature of 70 DEG C to the sea cucumber fucoidan solution in step (1), at microwave
The technological parameter of reason are as follows: microwave power 450W, microwave time 10min；
(3) second is carried out at a temperature of 45 DEG C to the sea cucumber fucoidan solution in step (2) to be ultrasonically treated,
Acquired solution through molecule interception be 1000kDa bag filter dialysis, vacuum freeze drying in 0.1Mpa vacuum degree, -45 DEG C
Dry 48h) after, 0.85g low-molecular-weightsea sea cucumber fucosan sulfate is obtained, the technological parameter of second of ultrasonic treatment are as follows: ultrasound
Sound field intensity is 200W/cm2, supersonic frequency 23kHz, ultrasonic time 40min；By resulting low molecular weight sea cucumber fucosan
Sulfuric ester detects molecular weight of product using gel permeation chromatography, and molecular weight is 263.0kDa(original sea cucumber sulfated fucan
Ester molecule amount is 1614.1kDa)；
(4) it takes 0.5g low-molecular-weightsea sea cucumber fucosan sulfate and is dissolved in 8ml dimethylformamide, by low point
Son amount sea cucumber fucoidan and K2CO3Mass ratio be 1:1.3 proportion be added 0.65gK2CO3It mixes, added
The methyl methylsulfonate of amount carries out sulfuric acid esterification, 60 DEG C of the reaction temperature of sulfuric acid esterification, reaction under agitation
Time 5h obtains reaction solution, the strong illumination of 70W is used during sulfuric acid esterification；
(5) it is mixed well after the ethyl acetate of 10 times of volumes is added in reaction solution, stands 2.5h, be centrifugated,
Centrifugal rotational speed 4000r/min, centrifugation time 12min, precipitating is multiple soluble in water after the cleaning of 70% ethanol solution, retains through molecule
Amount is the dialysis of 50kDa, and vacuum freeze drying (vacuum degree, -45 DEG C of dry 48h in 0.1Mpa) is to get low molecular weight high-sulfur
The sea cucumber fucoidan of acidification.
The sea cucumber fucoidan of the high sulphation of resulting low molecular weight is used into sulfate by ion chromatography the product sulfur
Acid group content, sulfate radical content are 26.3%) 40.8%(original sea cucumber fucoidan sulfate radical content is.
As can be seen from the above embodiments, the sea cucumber fucoidan of the high sulphation of the low molecular weight obtained through the invention
Molecular weight is low, and sulfate radical content is high, has stronger bioactivity.
Above-mentioned embodiment is only a preferred solution of the present invention, not the present invention is made in any form
Limitation, there are also other variations and modifications on the premise of not exceeding the technical scheme recorded in the claims.
Claims (4)
1. a kind of sea cucumber fucoidan preparation method of the high sulphation of low molecular weight, which is characterized in that including following step
It is rapid:
(1) sea cucumber fucoidan is soluble in water, first time ultrasonic treatment is carried out at a temperature of 30 ~ 40 DEG C；Described
The ultrasonic sound field intensity being once ultrasonically treated is 40 ~ 50W/cm2, supersonic frequency is 20 ~ 25kHz, 10 ~ 15min of ultrasonic time；
(2) microwave treatment is carried out at a temperature of 60 ~ 80 DEG C to the sea cucumber fucoidan solution in step (1)；It is described micro-
The technological parameter of wave processing are as follows: 400 ~ 600W of microwave power, 5 ~ 15min of microwave time；
(3) second is carried out at a temperature of 40 ~ 50 DEG C to the sea cucumber fucoidan solution in step (2) to be ultrasonically treated,
Acquired solution obtains low-molecular-weightsea sea cucumber fucosan sulfate after dialysis, vacuum freeze drying；Second of ultrasonic treatment
Ultrasonic sound field intensity be 100 ~ 300W/cm2, supersonic frequency is 20 ~ 25kHz, 30 ~ 60min of ultrasonic time；
(4) low-molecular-weightsea sea cucumber fucosan sulfate is dissolved in dimethylformamide, K is added2CO3, mix, added
The methyl methylsulfonate of amount carries out sulfuric acid esterification under agitation, obtains reaction solution；Low molecular weight sea cucumber fucosan
Sulfuric ester and K2CO3Mass ratio be 1:(1.2 ~ 1.4)；The strong illumination of 55 ~ 100W is used during sulfuric acid esterification；Sulfuric acid
50 ~ 70 DEG C of the reaction temperature of esterification, 4 ~ 8h of reaction time；
(5) it mixes well, stands after ethyl acetate being added in reaction solution, centrifuge separation, precipitating is cleaned through 70% ethanol solution
Afterwards, multiple soluble in water, through dialysing, vacuum freeze drying to get the high sulphation of low molecular weight sea cucumber fucoidan.
2. a kind of sea cucumber fucoidan preparation method of the high sulphation of low molecular weight according to claim 1,
It is characterized in that, in step (5), the ethyl acetate of 10 times of volumes is added in reaction solution.
3. a kind of sea cucumber fucoidan preparation method of the high sulphation of low molecular weight according to claim 1,
It is characterized in that, time of repose is 2 ~ 3h.
4. a kind of sea cucumber fucoidan preparation method of the high sulphation of low molecular weight according to claim 1,
It is characterized in that, centrifuging process parameter are as follows: 3500 ~ 4500r/min of centrifugal rotational speed, 10 ~ 15min of centrifugation time.
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| CN108467436A (en) * | 2018-06-12 | 2018-08-31 | 深圳大学 | The fucosan and its preparation method and application in undaria pinnitafida source |
| CN111748045B (en) * | 2019-03-27 | 2022-01-07 | 天津医科大学 | Preparation method and application of sargassum henslowianum fucoidan sulfate |
| CN109970823B (en) * | 2019-05-07 | 2020-08-07 | 青岛农业大学 | Fucooligosaccharide and preparation method and application thereof |
| CN111228297B (en) * | 2020-01-21 | 2021-03-19 | 山东大学 | Application of fucoidan sulfate in promoting autophagy decomposition of ox-LDL (low-density lipoprotein) by foam cells |
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|---|---|---|---|---|
| CN101993501A (en) * | 2009-08-26 | 2011-03-30 | 浙江科技学院 | Method for preparing fucoidan |
| CN103110659A (en) * | 2013-03-04 | 2013-05-22 | 中国海洋大学 | Application of trepang sulphated polysaccharide in preparation of drugs or products for resisting diabetes mellitus II |
| CN103467611A (en) * | 2013-08-15 | 2013-12-25 | 保龄宝生物股份有限公司 | Preparation method of carragheenan sulfated polysaccharides |
| CN103554297A (en) * | 2013-10-21 | 2014-02-05 | 兰州大学 | Preparation method and application of high-sulfation-degree radix hedysari polysaccharide sulfate |
| CN105131149A (en) * | 2015-08-13 | 2015-12-09 | 江苏大学 | Method for preparing narrow molecular weight distribution oligochitosan through ultrasonic/microwave combination |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101993501A (en) * | 2009-08-26 | 2011-03-30 | 浙江科技学院 | Method for preparing fucoidan |
| CN103110659A (en) * | 2013-03-04 | 2013-05-22 | 中国海洋大学 | Application of trepang sulphated polysaccharide in preparation of drugs or products for resisting diabetes mellitus II |
| CN103467611A (en) * | 2013-08-15 | 2013-12-25 | 保龄宝生物股份有限公司 | Preparation method of carragheenan sulfated polysaccharides |
| CN103554297A (en) * | 2013-10-21 | 2014-02-05 | 兰州大学 | Preparation method and application of high-sulfation-degree radix hedysari polysaccharide sulfate |
| CN105131149A (en) * | 2015-08-13 | 2015-12-09 | 江苏大学 | Method for preparing narrow molecular weight distribution oligochitosan through ultrasonic/microwave combination |
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