CN106749439B - Fucoidan oligosaccharide and the preparation method and application thereof - Google Patents
Fucoidan oligosaccharide and the preparation method and application thereof Download PDFInfo
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- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
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- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
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Abstract
The invention discloses fucoidan oligosaccharides and the preparation method and application thereof, and including the chain being connected in sequence by four fucosyl residues, by 1 → 3 and 1 → 4 chemical combination alternately occurs for fucosyl residues, and sulfate is distributed in the C of the second saccharide residue2And C3On and third saccharide residue C2On.The quantity of fucosyl residues (fixed structure) in fucoidan oligosaccharide provided in the present invention is 4 or 6, expand the quantity of the fucoidan oligosaccharide with fixed structure, and then the use scope of fucoidan oligosaccharide is expanded, more Component Sources are provided to prevent or treating the drug of atopic dermatitis and eczema, alimentary infection.
Description
Technical field
Present invention relates particularly to fucoidan oligosaccharides and the preparation method and application thereof.
Background technique
Fucoidin is a kind of brown alga heteroglycan of sulphation, bioactivity have broad spectrum activity [Fitton, J.H.,
Stringer,D.N.,and Karpiniec,S.S.(2015).Therapies from Fucoidan:An
Update.Marin Drugs 13,5920-5946.].However, due to polysaccharide formulation has heterogeneous and polysaccharide formulation cannot be by
Standardization, is medically practically impossible to using polymer molecule.Therefore, how to extract to have from fucoidin and fix
The oligosaccharide of structure and standard feature is just at a problem.The depolymerisation of fucoidin is realized using enzyme and extraction is provided
There is bioactivity oligosaccharide, provides new possibility using this kind of compound in pharmacy and lift face shaping for it
[Kusaykin,M.I.,Silchenko,A.S.,Zakharenko,A.M.,and Zvyagintseva,T.N.(2016)
.Fucoidanases.Glycobiology 26,3-12]。
Fucoidan oligosaccharide is used, in the mixture for preventing or treating atopic dermatitis and eczema
The saying of [RU2586776 C2, on June 10th, 2016], alimentary infection [WO2016139333 A1, on September 9th, 2016] is
Through being published.It has been proposed that using N- fucoidan oligosaccharide stimulation blood vessel [RU 2559629 C2,2015
On August 10 ,], and using sulfated oligosaccharides derivative as efficient heparin-binding protein inhibitor [RU 2483074C2,
On May 27th, 2013] be subject to using.It has been learnt that, fucosylation oligosaccharide can be used for protecting the plants from the evil of pathogen
[US 6984630 B1,10.01.2006].
Compared with multi-step takes the method extracting sulfuric acid oligosaccharide of organic synthesis, pass through enzyme preparation from fucoidin
The step of producing being unique in that for similar oligosaccharide: more simple possible, producing oligosaccharide in quantity for it is less, obtain
The reaction product yield arrived is higher.
Initially, what the hydrolysis that we pass through enzyme was got from withered bladder-wrack (Fucus evanescens) is rock algae
Polysaccharide oligomerization sugar.To reach this as a result, we are micro- fucoidin and from the ocean Formosa algae (Formosa algae)
The primary fucoidin FFA obtained in biology is mixed, and is put into 0.015M sodium phosphate buffer, pH value 7.2, and 25
DEG C temperature environment manually cultivate 72h.Macromolecule hydrolysis product, 10,000g centrifugations are settled out with 75% ethanol water
Supernatant is placed in rotary evaporator and is evaporated concentration by 30min, and distilled water pours into supernatant containing P-6 after redissolving
In biogel column, then watering balance elutes fucosylation oligosaccharide with the rate of 0.7mL/min.Low molecular weight
Oligosaccharide is put together, and concentration and again chromatographic isolation are carried out in rotary evaporator.As a result, what is generally yielded is knot
Structure is disaccharides [Xi Erqinke A.C., Formosa algae marine microorganism KMM 3553T and the sea mollusk spider of A and B
Fucoidin and algin catenase in spiral shell: chemical candidate doctor's degree reply paper.Russian national academy of sciences Far East branch
Pacific Ocean Bioorganic Chemistry research institute, Vladivostok, 2014, page 69].But structure is the disaccharides of A and B,
It is limited to the value volume and range of product of fucosyl residues in molecule, application range is smaller.
Summary of the invention
For above-mentioned the technical problems existing in the prior art, the object of the present invention is to provide a kind of sulfated fucans
Ester oligosaccharide, the quantity of the fucosyl residues (fixed structure) in the fucoidan oligosaccharide are 4 or 6, are expanded
The quantity of fucoidan oligosaccharide with fixed structure.
It is a further object to provide the preparation methods of above-mentioned fucoidan oligosaccharide.This method is benefit
Fucoidan oligosaccharide, more simple possible are produced in Sargassum horneri fucoidin solution with enzyme preparation, reaction product obtains
Rate is higher.
Third object of the present invention is to provide the applications of above-mentioned fucoidan oligosaccharide.
In order to solve the above technical problems, the technical solution of the present invention is as follows:
A kind of fucoidan oligosaccharide, including the chain being connected in sequence by four fucosyl residues, fucose
By 1 → 3 and 1 → 4 chemical combination alternately occurs for residue, and sulfate is distributed in the C of the second fucosyl residues2And C3On and third rock algae
The C of saccharide residue2On.
Preferably, above-mentioned fucoidan oligosaccharide further includes side chain, side chain by two kinds of non sulphates fucose
Residue is formed by 1 → 2 glucosides key connection, and side chain is by 1 → 4 glucosides key connection on third fucosyl residues.
Preferably, the fucoidan oligosaccharide is selected from following two:
The preparation method of above-mentioned fucoidan oligosaccharide, includes the following steps:
Recombination fucoidanase FFA1 and Sargassum horneri fucoidin solution are mixed in Tris-HCl buffer, mixed
Liquid, insulation reaction, heating enzyme deactivation, separation, obtains the fucoidan oligosaccharide of molecular formula I and II.
Someone can produce out recombination fucoidanase FFA1 [Xi Erqinke A.C., Fu Er by other known method
The fucoidin and algin catenase to rub in husky algae marine microorganism KMM 3553T and sea mollusk spider spiral shell: change
Learn candidate doctor's degree reply paper.Russian national academy of sciences Far East branch Pacific Ocean Bioorganic Chemistry research institute, Fu Ladi
Fertile stoke, 2014, page 110].
Preferably, the pH value of the Tris-HCl buffer is 7.0-7.5.
Preferably, the mass ratio of the recombination fucoidanase FFA1 and Sargassum horneri fucoidin is 0.01%-0.03%.
Preferably, the method for the cultivation is within the temperature range of 25 DEG C -38 DEG C, to cultivate 72-75h.
Preferably, the temperature of the heating enzyme deactivation is 95-105 DEG C, heating time 5-10min.
Preferably, wherein the separating step includes the steps that precipitating macromolecular hydrolysate, the precipitating with precipitating reagent
Agent is 75% ethanol water or 75% aqueous acetone solution.
It is further preferred that the separating step further includes that will precipitate the sediment centrifugation that macromolecular hydrolysate obtains to mention
The step of taking.
Still more preferably, the condition that the centrifugation is extracted are as follows: 9000-10000g, centrifugation time 20-30min.
Preferably, the separating step includes that the supernatant liquor after extraction sediment is poured into anion exchange absorbing column
In, carry out gradient elution the step of.
It is further preferred that in the anion exchange absorbing column, using ammonium hydrogen carbonate as eluant, eluent, with 1ml/min
Elution speed carry out gradient elution.
The fucoidan oligosaccharide or its officinal salt are as fucoidanase, fucosidase and sulfuric acid
Application in the matrix of esterase.
The fucoidan oligosaccharide or its officinal salt preparation for prevent or treat atopic dermatitis and
Eczema, alimentary infection drug in application.
A kind of pharmaceutical composition, it includes the above-mentioned fucoidan oligosaccharide of therapeutically effective amount or its is pharmaceutically acceptable
Salt.
Preferably, aforementioned pharmaceutical compositions further include pharmaceutical acceptable carrier.
The invention has the benefit that
The quantity of fucosyl residues (fixed structure) in fucoidan oligosaccharide provided in the present invention is 4
Or 6, the quantity of the fucoidan oligosaccharide with fixed structure is expanded, and then expand fucoidan
The use scope of oligosaccharide provides more groups to prevent or treating the drug of atopic dermatitis and eczema, alimentary infection
Divide source.
Two kinds of fucoidan oligosaccharides can be prepared using method of the invention, enrich sulfated fucan
The type of ester oligosaccharide.The yield of this method simple possible, reaction product is higher.
Specific embodiment
The present invention is further explained in the light of specific embodiments.
Embodiment 1
Recombination fucoidanase FFA1 (1mg) be put into pH value be 7.2 Tris-HCl buffer in and 5% Sargassum horneri
(Sargassum horneri) fucoidin solution mixes, people's work culture in 37 DEG C of temperature by mixture
72h is then heated to 100 DEG C, heating time 5min.The sediment of generation is separated and is discarded with centrifugal process.Upper
Ethyl alcohol is added in layer clear liquid, until its concentration reaches 75%.Sediment (macromolecule component) centrifugal treating of formation, 9000g, from
Heart time 20min.Supernatant liquor (low molecular composition) is poured into the cylinder containing Q- Ago-Gel adsorbent, uses pure water
Balance.Then with the speed of 1mL/min, linear gradient elution is carried out to oligosaccharide with ammonium hydrogen carbonate.First operation obtains molecular formula
For the sulphation fucosylation oligosaccharide of II, then operation obtains the sulphation fucosylation oligosaccharide that molecular formula is I, with
Obtained product is freeze-dried afterwards, the yield of obtained target product accounts for the 5-15% of low molecular composition total amount.
Embodiment 2
Recombination fucoidanase FFA1 (1mg) be put into pH value be 7.2 Tris-HCl buffer in and 10% Sargassum horneri
(Sargassum horneri) fucoidin solution mixes, people's work culture in 37 DEG C of temperature by mixture
75h is then heated to 100 DEG C, heating time 10min.The sediment of generation is separated and is discarded with centrifugal process.Upper
Acetone is added in layer clear liquid, until its concentration reaches 75%.The sediment (macromolecule component) of formation is subject to centrifugal treating,
10000g, centrifugation time 30min.Supernatant liquor (low molecular composition) is poured into the cylinder containing Q- Ago-Gel adsorbent
In, use pure water equilibrium.Then with the speed of 1mL/min, linear gradient elution is carried out to oligosaccharide with ammonium hydrogen carbonate.First operate
The fucoidan oligosaccharide for being II to molecular formula, then it is oligomeric to obtain the fucoidan that molecular formula is I for operation
Sugar is then freeze-dried obtained product, and the yield of obtained target product accounts for the 7-20% of low molecular composition total amount.
The structure of obtained oligosaccharide is determined with NMR spectrum.
In the oligosaccharide that molecular formula is I1H- is spectrally, it has been found that four different Alpha-Methyl-L- rock algae pyrans
Chemical shift has occurred in glucoside residue, this four residues are indicated with letter a-d respectively in table 1.By 1DTOXY spectrum
With COSY spectrum, chemical shift and their chemical sequence that each residue occurs can be determined.From HSQC- spectrum
In can determine1H chemical shift and13Relationship between C chemical shift.ROESY spectrum shows in d residue H1 and c residue H4
Between, between c residue H1 and a residue H3, there is relevance between b residue H1 and H3 residue and d residue H4.In HMBC spectrum
On, it is observed that between d residue С 1 and c residue H4, between c residue С 1 and a residue H3, b residue С 1 and d residue H3
Between have relevance.Similarly, proton d1, c1 and b1 correspondingly have relevance with carbon atom c4, a3 and d3 respectively.
On this basis it may be concluded that the oligosaccharide that molecular formula is I has a carbon skeleton: α-L-Fucp-1 → 3- α-
L-Fucp-1→4-α-L-Fucp-1→3-α-L-Fucp。
1 molecular formula of table is the chemical shift (ppm) of the fucosylation oligosaccharide of I
| Residue | H1 | H2 | H3 | H4 | H5 | H6 |
| a | 5.50 | 4.54 | 4.06 | 4.09 | 4.24 | 1.24 |
| b | 5.39 | 4.58 | 4.72 | 4.22 | 4.59 | 1.26 |
| c | 5.37 | 4.65 | 4.76 | 4.27 | 4.57 | 1.41 |
| d | 5.30 | 4.59 | 4.20 | 4.12 | 4.44 | 1.30 |
| C1 | C2 | C3 | C4 | C5 | C6 | |
| a | 91.74 | 74.62 | 74.99 | 70.40 | 67.12 | 16.65 |
| b | 95.86 | 73.61 | 76.33 | 71.81 | 67.74 | 16.44 |
| c | 96.32 | 73.68 | 75.16 | 80.54 | 69.07 | 16.85 |
| d | 99.93 | 74.62 | 74.49 | 70.62 | 68.28 | 16.51 |
Under the conditions of 700 megahertzs, 308K1The chemical shift of H spectrum, acetone 2.225 can measure various chemistry
Displacement.Under the conditions of 700 megahertzs, 308K13The chemical shift of С spectrum, acetone 31.45 can measure various chemical potentials
It moves.
By same mode, it can determine that molecular formula is the structure of the oligosaccharide of II.1H- spectrum shows that there are six
The different monosaccharide residue of kind.1DTOXY spectrum, COSY spectrum and HSQC spectrum can determine, the matter of each monosaccharide residue
Sub- chemical shift and carbon chemical shifts.These monosaccharide residues are all embodied in chart 2.
In ROESY spectrally it is observed that in a ' between residue H1 and d ' residue H4, in e ' residue H1 and d ' residue H3
Between, between d ' residue H1 and c ' residue H4, between c ' residue H1 and b ' residue H3, f ' residue H1 and a ' residue H2 it
Between, all there is correlation.HMBC spectrally, carbon atom a ' 1, d ' 1, e ' 1, f ' 1, c ' 1 respectively with proton d ' 4, c ' 4, d ' 3,
A ' 2 and b ' 3 has correlation, and proton a ' 1, e ' 1, f ' 1, d ' 1 is then respectively provided with phase with carbon atom d ' 4, d ' 3, a ' 2, c ' 4
Guan Xing.In addition, in HMBC spectrally it is observed that carbon atom b ' 3 and proton c ' 1 or d ' 1 has correlation.
2 molecular formula of table is the chemical shift (ppm) of the fucosylation oligosaccharide of II
Under the conditions of 700 megahertzs, 308K1The chemical shift of H spectrum, acetone 2.225 can measure various chemistry
Displacement.Under the conditions of 700 megahertzs, 308K13The chemical shift of С spectrum, acetone 31.45 can measure various chemical potentials
It moves.
Based on discussed above it can be concluded that molecular formula is that the oligosaccharide of II has the branched structure of following form:
Position of the sulfate in monosaccharide residue, can by by its proton displacement and fucose (H1=5,19, H2=
3,76, H3=3,85, H4=3,80, H5=4,19, H6=1,20) it compares and is determined, it can also be by former by its carbon
Son displacement with Alpha-Methyl-L- rock algae pyranoside (C1=100,5, C2=69,0, С 3=70,6, С 4=72,9, С 5=67,
5, С 6=16,5) it compares and is determined.Movement and Alpha-Methyl-L- rock according to fucose H2 in feeble field 0.8-0.9ppm
Algae pyranoside feeble field 4-6ppm movement, it can be calculated that sulfation has occurred in position 2.According to H3 weak
Movement of the movement and C3 of field 0.9-1.0ppm in feeble field 4-6ppm can determine that there are sulfate in position 3.
Above-mentioned, although specific embodiments of the present invention have been described, the limitation not to invention protection scope,
Those skilled in the art should understand that based on the technical solutions of the present invention, those skilled in the art do not need to pay
The various modifications or changes that creative work can be made are still within the scope of the present invention.
Claims (5)
1. the preparation method of sulfated fucan oligosaccharide, characterized by the following steps:
Recombination fucoidanase FFA1 and Sargassum horneri fucoidin solution are mixed in Tris-HCl buffer, obtain mixed liquor,
Insulation reaction, heating enzyme deactivation, separation, obtain the fucoidan oligosaccharide of molecular formula I and II；
2. preparation method according to claim 1, it is characterised in that: wherein the separating step includes being precipitated with precipitating reagent
The step of macromolecular hydrolysate, the precipitating reagent are 75% ethanol water or 75% aqueous acetone solution.
3. preparation method according to claim 1, it is characterised in that: the separating step further includes that will precipitate macromolecular water
The step of sediment centrifugation that solution product obtains is extracted.
4. preparation method according to claim 3, it is characterised in that: the separating step includes after extracting sediment
The step of supernatant liquor pours into anion exchange absorbing column, carries out gradient elution.
5. the fucoidan oligosaccharide of the molecular formula II of any preparation method preparation of claim 1-3 or its can medicine
Use application of the salt in the matrix as fucoidanase, fucosidase and sulfatase.
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