CN104560774A - Method for preparing block oligosaccharide containing rich rhamnose sulfate from Enteromorpha polysaccharide - Google Patents

Method for preparing block oligosaccharide containing rich rhamnose sulfate from Enteromorpha polysaccharide Download PDF

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CN104560774A
CN104560774A CN201410298678.2A CN201410298678A CN104560774A CN 104560774 A CN104560774 A CN 104560774A CN 201410298678 A CN201410298678 A CN 201410298678A CN 104560774 A CN104560774 A CN 104560774A
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sea grass
rhamnosyl
grass polysaccharide
oligosaccharides
rich
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CN104560774B (en
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王鹏
李银平
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Ocean University of China
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    • C12P19/00—Preparation of compounds containing saccharide radicals
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    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • 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 relates to a method for preparing block oligosaccharide containing rich rhamnose sulfate from Enteromorpha polysaccharide, belonging to the technical field of biology. A strain Catenovulum sp.LP214 is utilized to perform fermentation by using Enteromorpha polysaccharide lyase; and the block oligosaccharide containing rich rhamnose sulfate is prepared by degrading Enteromorpha polysaccharide with the enzyme at 25-45 DEG C under the condition of the pH value of 5-7.5 for 1-8 hours. The polymerization degree of the block oligosaccharide containing rich rhamnose sulfate is 2-8, and the rhamnose sulfate content is greater than or equal to 30%. The preparation method is simple to operate, has the advantages of mild conditions, high yield, complete monosaccharide structure, low cost and the like, and can easily implement industrial production.

Description

A kind of sea grass polysaccharide that utilizes prepares the method being rich in rhamnosyl sulfuric ester block oligosaccharides
Technical field
The present invention relates to a kind of sea grass polysaccharide that utilizes and prepare the method being rich in rhamnosyl sulfuric ester block oligosaccharides, belong to biological technical field.
Background technology
Sea grass polysaccharide is a kind ofly formed by rhamnosyl, wood sugar, glucuronic acid and be rich in the polyanion sugar chain of sulfate.Tang et al.(2013) research finds that the monose of sea grass polysaccharide consists of rhamnosyl, wood sugar, glucuronic acid, mass percent is respectively 64.2%, 18.2%, 12.6%, and sulfate content is 19.6%, and polysaccharide molecular weight is 103.51 KDa.Ray et al.(2006) research show that in Enteromorpha, rhamnosyl is (1 → 2,4) key connects, glucuronic acid is that (1 → 4) key connects, and wood sugar is that (1 → 4) key connects, and sulfate is in rhamnosyl C-3 and holds formation rhamnosyl sulfuric ester.
Research finds that sea grass polysaccharide has antitumor, anticoagulation, hypoglycemic blood fat, improves the effect such as immunizing power, antioxygenic activity.Sea grass polysaccharide contains two kinds of potential function sugar compositions: glucuronic acid, rhamnosyl sulfuric ester.Wherein, glucuronic acid has liver detoxification effect, is the main additive of functional beverage, food, makeup.And rhamnosyl can participate in synthetic perfume, cardiac glycoside medicine and Sugar receptors etc., there is obvious immunocompetence.Be proved with the fucose sulfate of rhamnosyl sulfuric ester structural similitude and have the important physiological function such as nerve conduction, immunomodulatory, therefore rhamnosyl sulfuric ester is a kind of potential functional component.
But in application process, the molecular weight that polysaccharide is higher and viscosity reduce its physiological function.Find the method that a species specificity prepares oligosaccharides and become the effective means solving its application.Compared to chemical method and Physical, microbial enzyme method has its potential advantages: (1) reaction is efficient, stable, the advantage that the product polymerization degree is controlled; (2) product uniformity is good, yield is high, is easy to separation, purifying; (3) mild condition, has environment friendly, and product better remains the active group of sugar chain.
But, not yet find both at home and abroad at present about utilizing sea grass polysaccharide to be rich in the research report of rhamnosyl sulfuric ester block oligosaccharides by microbial enzyme preparation.
Summary of the invention
The invention provides a kind of sea grass polysaccharide lyase that utilizes and prepare the method being rich in rhamnosyl sulfuric ester block oligosaccharides.The method take sea grass polysaccharide as raw material, and by specific degradation under the effect of microbial enzyme, and then rhamnosyl sulfuric ester block oligosaccharides is rich in acquisition.The inventive method has that specificity is good, mild condition, output are high, oligosaccharides active group is complete, low cost and other advantages.The exploitation of novel active oligosaccharides, structure activity relationship and application and development are all had important practical significance.
The bacterial strain of the product sea grass polysaccharide lyase that the present invention relates to is catenovulumsp. LP214, this bacterial strain is deposited in Wuhan, China Wuhan University China typical culture collection center on April 20th, 2014, and deposit number is CCTCC NO:M2014136.
Technological method provided by the invention is the preparation adopting following steps to realize being rich in rhamnosyl sulfuric ester block oligosaccharides:
(1) will catenovulumsp. ferment in LP214 inoculation to culture medium, wherein culture medium consists of sea grass polysaccharide 10 g, yeast extract paste 3 g, magnesium sulfate 4 g, calcium chloride 0.5 g, sodium-chlor 20 g, ammonium sulfate 1.5 g, high ferric phosphate 0.2 g, tap water 1000 ml, pH 7.5; Fermentation condition is 32 DEG C, 36 h; By centrifugal for fermented liquid 10000 r/min 5 min, obtain supernatant liquor.
(2) taking-up after 40 DEG C of insulation 30-45 min of the supernatant liquor in step (1) is cooled to room temperature and obtains sea grass polysaccharide lyase.
(3) sea grass polysaccharide water-soluble preparation 0.1-2.5%(w/v) sea grass polysaccharide solution, sea grass polysaccharide lyase step (2) obtained is by 8-16 U/g(sea grass polysaccharide) be added in sea grass polysaccharide solution, in 25-45 DEG C, pH 5.0-7.5, enzymolysis 1-8 h; Under wherein 1 enzyme activity unit is defined as 35 DEG C of conditions, per minute produces the enzyme amount required for 1 μm of ol reducing sugar (with glucose meter).After enzymolysis, be warming up to 100 DEG C, insulation 1-2 min makes enzyme-deactivating, and after cooling, centrifugal 10 min of 8000 r/min, get supernatant enzymolysis solution; Be the ultra-filtration membrane removing macromolecular substance of 3000 Da by supernatant enzymolysis solution molecular weight cut-off, obtain being rich in rhamnosyl sulfuric ester block oligosaccharides.
Prepared by the inventive method be rich in rhamnosyl sulfuric ester block oligosaccharides carries out quantitative and qualitative analysis by following concrete grammar:
(1) be rich in rhamnosyl sulfuric ester block oligosaccharides after hydrolysis by above-mentioned preparation, adopt the monose composition of high effective liquid chromatography for measuring oligosaccharides.To buy the seminose of Sigma company, rhamnosyl, glucuronic acid, galacturonic acid, glucose, semi-lactosi, wood sugar, pectinose as standard substance, detect monose composition (as shown in Figure 1, Figure 2) of oligosaccharides.Enzymolysis product analytical results shows, the monose composition of such oligosaccharides is mainly rhamnosyl, glucuronic acid, wood sugar, wherein rhamnosyl content >=30%.
(2) bariumchloride turbidimetry is adopted to carry out sulfate assay, oligosaccharides sulfate content >=15% the rhamnosyl sulfuric ester block oligosaccharides that is rich in of above-mentioned preparation.
(3) the rhamnosyl sulfuric ester block oligosaccharides that is rich in of above-mentioned preparation is carried out ESI-MS(negative ion) analyze, the results are shown in Figure 3.The fragment that wherein abundance is higher has 7 kinds, and molecular weight is respectively 402,628,760,982,1124,1268,1430, and the polymerization degree is respectively 2-8.According to the monose of oligosaccharides composition and substituting group analytical results, such as, the disaccharides that is made up of a rhamnosyl sulfuric ester and a glucuronic acid of the oligosaccharides of 402 Da.The rhamnosyl sulfuric ester unit do not waited containing 2-4 respectively in other oligose fragment.
Accompanying drawing explanation
Fig. 1 is the liquid chromatogram of monose standard substance, and wherein appearance time is that 21.668,25.986,27.971,29.957,31.077,32.949,34.884,35.469,36.126 min are respectively seminose, rhamnosyl, glucuronic acid, galacturonic acid, interior mark lactose, glucose, semi-lactosi, wood sugar, pectinose.
Fig. 2 is the liquid chromatogram being rich in rhamnosyl sulfuric ester block oligosaccharides after hydrolysis, occurs respectively being rich in rhamnosyl sulfuric ester block oligosaccharides containing rhamnosyl, glucuronic acid, wood sugar after absorption peak shows hydrolysis at 25.986,27.971,35.469 min.
Fig. 3 is the mass spectrum being rich in rhamnosyl sulfuric ester block oligosaccharides.
Embodiment
Embodiment 1
Be rich in the preparation method of rhamnosyl sulfuric ester block oligosaccharides, comprise the following steps:
(1) will catenovulumsp. ferment in LP214 inoculation to culture medium, wherein culture medium consists of sea grass polysaccharide 10 g, yeast extract paste 3 g, magnesium sulfate 4 g, calcium chloride 0.5 g, sodium-chlor 20 g, ammonium sulfate 1.5 g, high ferric phosphate 0.2 g, tap water 1000 ml, pH 7.5; Fermentation condition is 32 DEG C, 36 h; By centrifugal for fermented liquid 10000 r/min 5 min, obtain supernatant liquor.
(2) taking-up after 40 DEG C of insulation 30-45 min of the supernatant liquor in step (1) is cooled to room temperature and obtains sea grass polysaccharide lyase.
(3) be dissolved in 100 L distilled water by 1 Kg sea grass polysaccharide, tune pH is 6-7.The sea grass polysaccharide lyase prepared by step (2) adding 10 units in sea grass polysaccharide solution carries out enzymolysis, and under 1 enzyme activity unit is defined as 35 DEG C of conditions, per minute produces the enzyme amount required for 1 μm of ol reducing sugar (with glucose meter); Concrete grammar is in 30 DEG C, and 100 r/min shake reaction 5 h; After enzymolysis, be warming up to 100 DEG C, insulation 1-2 min makes enzyme-deactivating, and after cooling, centrifugal 10 min of 8000 r/min, get supernatant enzymolysis solution; The ultra-filtration membrane being 3000 Da by supernatant enzymolysis solution molecular weight cut-off removes macromolecular material, obtains being rich in rhamnosyl sulfuric ester block oligosaccharides.
Embodiment 2
Be rich in the preparation method of rhamnosyl sulfuric ester block oligosaccharides, comprise the following steps:
(1) will catenovulumsp. ferment in LP214 inoculation to culture medium, wherein culture medium consists of sea grass polysaccharide 10 g, yeast extract paste 3 g, magnesium sulfate 4 g, calcium chloride 0.5 g, sodium-chlor 20 g, ammonium sulfate 1.5 g, high ferric phosphate 0.2 g, tap water 1000 ml, pH 7.5; Fermentation condition is 32 DEG C, 36 h; By centrifugal for fermented liquid 10000 r/min 5 min, obtain supernatant liquor.
(2) taking-up after 40 DEG C of insulation 30-45 min of the supernatant liquor in step (1) is cooled to room temperature and obtains sea grass polysaccharide lyase.
(3) be dissolved in 100 L distilled water by 2 Kg sea grass polysaccharides, tune pH is 6-7.The sea grass polysaccharide lyase prepared by step (2) adding 10 units in sea grass polysaccharide solution carries out enzymolysis, and under 1 enzyme activity unit is defined as 35 DEG C of conditions, per minute produces the enzyme amount required for 1 μm of ol reducing sugar (with glucose meter); Concrete grammar is in 35 DEG C, and 100 r/min shake reaction 5 h; After enzymolysis, be warming up to 100 DEG C, insulation 1-2 min makes enzyme-deactivating, and after cooling, centrifugal 10 min of 8000 r/min, get supernatant enzymolysis solution; Be the ultra-filtration membrane removing macromolecular substance of 3000 Da by supernatant enzymolysis solution molecular weight cut-off, obtain being rich in rhamnosyl sulfuric ester block oligosaccharides.

Claims (3)

1. produce the bacterial strain of sea grass polysaccharide lyase, this bacterial strain is catenovulumsp. LP214, preserving number CCTCC NO:M2014136, depositary institution: Chinese Typical Representative type culture collection center.
2. utilize sea grass polysaccharide lyase to prepare the method being rich in rhamnosyl sulfuric ester block oligosaccharides, step is as follows:
(1) acquisition of sea grass polysaccharide lyase
Ferment in inoculation according to claim 1 to culture medium, fermentation condition is 32 DEG C, 36 h; Wherein culture medium consists of sea grass polysaccharide 10 g, yeast extract paste 3 g, magnesium sulfate 4 g, calcium chloride 0.5 g, sodium-chlor 20 g, ammonium sulfate 1.5 g, high ferric phosphate 0.2 g, tap water 1000 ml, pH 7.5; By centrifugal for fermented liquid 10000 r/min 5 min, obtain supernatant liquor, supernatant liquor taking-up after 40 DEG C of insulation 30-45 min is cooled to room temperature and obtains sea grass polysaccharide lyase;
(2) preparation of rhamnosyl sulfuric ester block oligosaccharides is rich in
By water-soluble for sea grass polysaccharide preparation 0.1-2.5%(w/v) sea grass polysaccharide solution, the sea grass polysaccharide lyase that step (1) obtains is added in sea grass polysaccharide solution, in 25-45 DEG C, pH 5.0-7.5, enzymolysis 1-8 h; After enzymolysis, be warming up to 100 DEG C, insulation 1-2 min makes enzyme-deactivating, and after cooling, centrifugal 10 min of 8000 r/min, get supernatant enzymolysis solution; Be the ultra-filtration membrane removing macromolecular substance of 3000 Da by supernatant enzymolysis solution molecular weight cut-off, obtain being rich in rhamnosyl sulfuric ester block oligosaccharides.
3. method according to claim 2, wherein said is rich in rhamnosyl sulfuric ester block oligosaccharides, and the polymerization degree is 2-8, and molecular weight contains 402,628,760 Da, content >=30% of rhamnosyl sulfuric ester.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108239176A (en) * 2016-12-27 2018-07-03 中国海洋大学 Low molecular weight sea grass polysaccharide and preparation method thereof, sulphation low molecular weight sea grass polysaccharide and preparation method thereof and application
CN112825993A (en) * 2021-01-22 2021-05-25 河南省纳普生物技术有限公司 Preparation method for improving antioxidant effect of roxburgh rose fermented fruit drink
CN114376233A (en) * 2022-03-23 2022-04-22 青岛海大生物集团股份有限公司 Enteromorpha polysaccharide health food with immunity enhancing function and preparation method thereof

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CN103194414A (en) * 2013-04-22 2013-07-10 淮海工学院 Marine catenovulumsp. DP03 and method for producing dextran enzyme by using same
CN103451119A (en) * 2012-06-03 2013-12-18 中国海洋大学 Alteromonas and method thereby for producing gel-type enteromorpha polysaccharide degrading enzyme by using Alteromonas

Patent Citations (2)

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CN103451119A (en) * 2012-06-03 2013-12-18 中国海洋大学 Alteromonas and method thereby for producing gel-type enteromorpha polysaccharide degrading enzyme by using Alteromonas
CN103194414A (en) * 2013-04-22 2013-07-10 淮海工学院 Marine catenovulumsp. DP03 and method for producing dextran enzyme by using same

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108239176A (en) * 2016-12-27 2018-07-03 中国海洋大学 Low molecular weight sea grass polysaccharide and preparation method thereof, sulphation low molecular weight sea grass polysaccharide and preparation method thereof and application
CN108239176B (en) * 2016-12-27 2021-08-17 中国海洋大学 Low-molecular-weight enteromorpha polysaccharide and preparation method thereof, sulfated low-molecular-weight enteromorpha polysaccharide and preparation method and application thereof
CN112825993A (en) * 2021-01-22 2021-05-25 河南省纳普生物技术有限公司 Preparation method for improving antioxidant effect of roxburgh rose fermented fruit drink
CN112825993B (en) * 2021-01-22 2022-06-17 河南省纳普生物技术有限公司 Preparation method for improving antioxidant effect of roxburgh rose fermented fruit drink
CN114376233A (en) * 2022-03-23 2022-04-22 青岛海大生物集团股份有限公司 Enteromorpha polysaccharide health food with immunity enhancing function and preparation method thereof

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