CN109988872A - A kind of preparation method of Oligomeric manna sugar - Google Patents
A kind of preparation method of Oligomeric manna sugar Download PDFInfo
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- CN109988872A CN109988872A CN201910337624.5A CN201910337624A CN109988872A CN 109988872 A CN109988872 A CN 109988872A CN 201910337624 A CN201910337624 A CN 201910337624A CN 109988872 A CN109988872 A CN 109988872A
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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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- 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
- C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
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Abstract
The present invention relates to a kind of preparation methods of Oligomeric manna sugar, comprising: galactomannans solution is carried out the homogeneous processing of high-pressure fluid nanometer, acetic acid is then added and carries out degradation reaction；Recycling acetic acid is concentrated under reduced pressure after degradation reaction alternatively, further comprising, obtains Oligomeric manna sugar after concentrate is spray-dried.The present invention is by galactomannans through high-pressure fluid nanometer homogenizer homogeneous, and directly plus acetolysis, uniform hydrolyses, hydrolysis rate are fast.Compared with the inorganic acids such as hydrochloric acid, sulfuric acid, trifluoroacetic acid, acetic acid belongs to organic acid, corrodes small to equipment and is easily recycled.The method of the present invention can be improved Oligomeric manna sugar production efficiency, improve product selectivity, have good prospects for commercial application.
Description
Technical field
The present invention relates to the preparation methods of Oligomeric manna sugar.
Background technique
Galactomannan gum body is present in mostly in the endosperm of seeds of leguminous plant, resourceful, has preferable water
Dissolubility and still there is higher viscosity in diluter solution.But it is limited in food since galactomannan gum viscosity is high
Application pharmaceutically.Therefore it needs to carry out degradation modification to galactomannans, to realize its higher value application.Study table
Bright, main chain is made of β-(1 → 4)-glucosides key connection D- mannopyranose in galactomannan molecule structure, D- galactolipin
By in α-(1 → 6)-glucosides key connection to mannose backbone in the form of side chain.
Oligomeric manna sugar is to use to contain galactomannans (C6H10O5)nThe raw material of (n represents average degree of polymerization) uses a system
A kind of oligosaccharide of column method preparation.Oligomeric manna sugar has been developed in recent years a kind of functional oligose, degree of polymerization 2-4
Oligomeric manna sugar have significant Bifidobacterium cultivation effect.Oligomeric manna sugar is uniquely can be in conjunction with external source venereal bacteria in enteron aisle
New type functional oligosaccharide, it can in conjunction with pathogen velvet-like pili, prevent pathogen to be attached in intestinal wall.As people are to low
The raising of the functional understanding of poly- mannose, the application field of Oligomeric manna sugar is more and more wider, its market demand also will year by year
Increase, development prospect is very wide.
The common preparation method of Oligomeric manna sugar has direct enzymatic isolation method, acid-hydrolysis method and physical degradation methods.Direct enzymatic isolation method
Galactomannans is directly acted on beta mannosidase, but usually enzymatic activity is lower, causes Oligomeric manna sugar yield low, and
Enzyme purification process is complicated, enzymolysis time is long, viscosity causes concentration of substrate excessively high cannot limit large-scale industrial production.
Physical degradation methods include microwave, ultrasound, irradiation, dynamic high-pressure rheological method.Easy to operate but the high requirements on the equipment is not suitable for big rule
The industrialized production of mould.Acid-hydrolysis method is to directly act on galactomannans with acid to prepare Oligomeric manna sugar, and common acid has
Sulfuric acid, hydrochloric acid, trifluoroacetic acid.Acid hydrolyzation efficiency is higher and high concentration of substrate will not inhibit to react, but inorganic acid corrodes equipment
Serious and Oligomeric manna sugar is selectively low.In the technique of existing sour water solution production Oligomeric manna sugar, acid is sulphur mostly
Acid is low with the acid of the severe corrosion to equipment such as hydrochloric acid and Oligomeric manna sugar yield.
Summary of the invention
In order to improve Oligomeric manna sugar production efficiency, improve product selectivity, the present invention provides a kind of low mannosan
Preparation method produces Oligomeric manna sugar using acetolysis galactomannans, has good prospects for commercial application.
Specifically, the preparation method of Oligomeric manna sugar of the present invention includes: that galactomannans solution is carried out high-pressure spray
Then the homogeneous processing of body nanometer is added acetic acid and carries out degradation reaction；It is depressurized after degradation reaction alternatively, further comprising
Concentration and recovery acetic acid obtains Oligomeric manna sugar after being spray-dried concentrate.
This field conventional equipment can be used in homogeneous handle of high-pressure fluid nanometer of the present invention, such as high-pressure fluid nanometer is even
Matter machine.
Further, the high-pressure fluid nanometer homogenization pressure is 190-210MPa, preferably 200MPa.Generally preferably
Matter 2-3 times.
The present invention by carrying out the homogeneous processing of high-pressure fluid nanometer to galactomannans unexpectedly the study found that can be incited somebody to action
Galactomannans macromolecular dispersing and dissolving is uniformly to significantly improve acetic acid degradation efficiency, Oligomeric manna sugar in acetic acid degradation solution
(mannobiose, manninotriose, mannotetrose) total concentration is significantly improved, and also improves the total reducing sugar in Oligomeric manna sugar
Content.
The research of the invention finds that the present invention uses second compared with the acid-hydrolysis methods such as common sulfuric acid, hydrochloric acid, trifluoroacetic acid
Acid degradation galactomannans can significantly improve Oligomeric manna sugar yield, and significantly reduce the corrosion for equipment, not instead
The acetic acid answered can be recycled by physical methods such as evaporations.
Further, the study found that acetic acid concentration used is preferably 2-6M, degradation reaction temperature is preferably 120-140 DEG C,
The degradation reaction time is preferably 1-4h.In preferably embodiment of the invention, acetic acid concentration used is 5-6M, degradation reaction temperature
Degree is 120-130 DEG C, and the degradation reaction time is 1-2h.Degradation efficiency can be improved under this condition, and improve mannobiose and
The yield of manninotriose.
Further, the study found that the mass ratio of acetic acid used and galactomannans is preferably 0.7:1-1.5:1, more
Preferably 1.2:1-1.5:1.The degradation reaction time can be shortened under this condition, improve mannobiose and manninotriose
Rate.
Galactomannans solution of the present invention can be prepared with conventional method in that art, and concentration is usually in 80-100g/
L。
Galactomannans solution of the present invention, which can also be from wild Chinese honey locust or wild Chinese honey locust polysaccharide gum (powder), to be extracted and obtains.
Wild Chinese honey locust is distributed in the ground such as China Hebei, Henan, Shanxi, Shandong and Shaanxi, and wild Chinese honey locust polysaccharide gum derives from pulse family
The shrub of Gleditsia and the endosperm fraction of dungarunga open country Chinese honey locust bean gum have potential prospects for commercial application.The present invention is to wild soap
Pod raw material and wild Chinese honey locust rubber powder (hydration alcohol precipitation extract wild Chinese honey locust rubber powder) after purification have carried out component analysis, as a result such as
Shown in table 1.Compared with wild Chinese honey locust raw material, galactomannans content is greater than 91.85% in wild Chinese honey locust rubber powder after purification, therefore
Galactomannans after purification can be used as a kind of desirable feedstock for producing Oligomeric manna sugar.
The component analysis of table 1 wild Chinese honey locust amylose gelatine powder and purified polysaccharide
Extract the extraction efficiency of galactomannans from wild Chinese honey locust or wild Chinese honey locust amylose gelatine powder to improve, and improve with
It is the subsequent yield and quality for preparing Oligomeric manna sugar of raw material, and the present invention also carries out the method for extracting galactomannans
Research.Preferably, wild Chinese honey locust or wild Chinese honey locust amylose gelatine powder are dissolved into 60-80 DEG C of water hydration 2-4h, is centrifuged after hydration
Separation takes supernatant, dehydrated alcohol then plus in equal volume, is centrifugated after alcohol precipitation, and precipitating is galactomannans；It is added
Suitable quantity of water can be made into galactomannans solution.Preferably, in above-mentioned hydration reaction wild Chinese honey locust or wild Chinese honey locust amylose gelatine powder with
The weight ratio of water is 1%-3%.In a preferred embodiment of this invention, the temperature of above-mentioned hydration reaction is 70 DEG C, hydration time
For 3h, the alcohol precipitation time is 2h.
The invention also includes the Oligomeric manna sugars of above method preparation, and wherein mannobiose, manninotriose, mannotetrose contain
Amount is high, and purity is high can be used for the fields such as food and health food, have the advantages that quality is stable, impurity content is low etc..
The utility model has the advantages that
(1) galactomannans rich in wild Chinese honey locust rubber powder, and galactomannan molecule amount is it has been found that original
It is minimum in material, it is the desirable feedstock for preparing Oligomeric manna sugar.
(2) impurity in wild Chinese honey locust polysaccharide gum, the supernatant after centrifuge separation can be effectively removed using hydration and alcohol precipitating method
Liquid passes through vacuum distillation reuse process water and ethyl alcohol, non-wastewater discharge.
(3) galactomannans after being centrifugated is through high-pressure fluid nanometer homogenizer homogeneous, directly plus acetolysis, water
Uniformly, hydrolysis rate is fast for solution.
(4) compared with the inorganic acids such as hydrochloric acid, sulfuric acid, trifluoroacetic acid, acetic acid belongs to organic acid, corrodes small to equipment and is easy to
Recycling.
(5) during Acetic hydrolysed galactomannan prepares Oligomeric manna sugar, the reaction time is short, and acetic acid can be shown
It writes and improves Oligomeric manna sugar yield.
(6) recyclable most of acetic acid is concentrated under reduced pressure in hydrolyzed liquid, and the low of high-purity further can be obtained after spray drying
Poly- sweet dew sugar product.
Detailed description of the invention
Fig. 1 is 1-3 of embodiment of the present invention process flow chart.
Fig. 2, Fig. 3 are respectively the high-efficient liquid phase chromatogram of 1 acetolysis liquid of embodiment 1 and comparative example.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..It is not specified in embodiment specific
Technology or conditions person, described technology or conditions according to the literature in the art, or carried out according to product description.It is used
Production firm person is not specified in reagent or instrument, is the conventional products that can be commercially available by regular distributor.
The wild Chinese honey locust amylose gelatine powder of industry used below is related to by Hebei to be provided for group company, wherein galactomannans content
It is 72.6%, beta-dextran content 3.6%, protein content 10.1%, content of ashes 0.5%.
- 3 process flow chart of following example 1 is referring to Fig. 1.
Embodiment 1
The present embodiment provides the preparation method of galactomannans first, comprising: the wild Chinese honey locust polysaccharide gum rubber powder of 6g industry is taken,
With 70 DEG C of hydration 3h of 300g, it is centrifuged off water-insoluble, supernatant is then taken to add dehydrated alcohol under stiring by 1:1 (v/v), it is quiet
It is centrifugated after setting 2h, precipitating is galactomannans.Supernatant can be evaporated under reduced pressure recycling second alcohol and water.
The present embodiment also provides the preparation method of Oligomeric manna sugar, comprising: by galactomannans manufactured in the present embodiment
Add water that the solution of concentration 10% is made, by the homogenization at 200MPa of high-pressure fluid nanometer homogenizer, homogenization
Galactomannan gum moves into reaction kettle, and 20mL5M acetic acid is added, reacts 2h at 130 DEG C, obtains acetic acid degradation solution；The drop
Liquid is solved by vacuum concentration recycling acetic acid, Oligomeric manna sugar is further obtained by spray drying.
The acetolysis liquid that the present embodiment is obtained using efficient liquid phase chromatographic analysis (see Fig. 2, M2: mannobiose, M3:
Manninotriose；M4: mannotetrose), wherein Oligomeric manna sugar (mannobiose, manninotriose, mannotetrose) total concentration is 39g/
L, wherein mannobiose is 13.3g/L, manninotriose 13.2g/L, mannotetrose 12.5g/L.
Total sugar content is 93.6% in Oligomeric manna sugar product made from the present embodiment.
Embodiment 2
The present embodiment provides the preparation method of Oligomeric manna sugar, the difference with embodiment 1 is only that high-pressure fluid nanometer
Galactomannans after homogenization moves into reaction kettle, and 20mL 6M acetic acid is added, reacts 2h at 120 DEG C, obtains acetic acid
Degradation solution；The degradation solution further obtains Oligomeric manna sugar by spray drying by vacuum concentration recycling acetic acid.
The acetolysis liquid that the present embodiment is obtained uses efficient liquid phase chromatographic analysis, wherein Oligomeric manna sugar (sweet dew two
Sugar, manninotriose, mannotetrose) total concentration be 32.7g/L, wherein mannobiose be 10.4g/L, manninotriose 11.7g/L,
Mannotetrose is 10.6g/L.
Total sugar content is 93.3% in Oligomeric manna sugar product made from the present embodiment.
Embodiment 3
The present embodiment provides the preparation method of Oligomeric manna sugar, the difference with embodiment 1 is only that high-pressure fluid nanometer
Galactomannans after homogenization moves into reaction kettle, and 20mL6M acetic acid is added, reacts 1h at 130 DEG C, obtains acetic acid
Degradation solution；The degradation solution further obtains Oligomeric manna sugar by spray drying by vacuum concentration recycling acetic acid.
The acetolysis liquid that the present embodiment is obtained uses efficient liquid phase chromatographic analysis, wherein Oligomeric manna sugar (sweet dew two
Sugar, manninotriose, mannotetrose) total concentration be 30.5g/L, wherein mannobiose be 9.6g/L, manninotriose 11.3g/L,
Mannotetrose is 9.6g/L.
Total sugar content is 93.1% in Oligomeric manna sugar product made from the present embodiment.
Comparative example 1
This comparative example provides the preparation method of Oligomeric manna sugar, and the difference with embodiment 1 is only that galactomannans is molten
Liquid directly moves into reaction kettle without high-pressure fluid nanometer homogenization, and 20mL 5M acetic acid is added, reacts at 130 DEG C
2h obtains acetic acid degradation solution；The degradation solution further obtains oligomeric sweet dew by spray drying by vacuum concentration recycling acetic acid
Sugar.
The acetolysis liquid that this comparative example is obtained using efficient liquid phase chromatographic analysis (see Fig. 3, M2: mannobiose, M3:
Manninotriose；M4: mannotetrose), wherein Oligomeric manna sugar (mannobiose, manninotriose, mannotetrose) total concentration is 8.5g/
L, wherein mannobiose is 6.2g/L, and manninotriose 2.3g/L does not detect mannotetrose.Oligomeric manna sugar total yield,
Mannobiose yield and manninotriose are substantially less than embodiment 1-3.
Total sugar content is 86.3% in Oligomeric manna sugar product made from this comparative example, substantially less than embodiment 1-3.
Comparative example 2
This comparative example provides the preparation method of Oligomeric manna sugar, and the difference with embodiment 1 is only that galactomannans is molten
Liquid directly moves into reaction kettle without high-pressure fluid nanometer homogenization, and 20mL 6M acetic acid is added, reacts at 130 DEG C
2h obtains acetic acid degradation solution；The degradation solution further obtains oligomeric sweet dew by spray drying by vacuum concentration recycling acetic acid
Sugar.
The acetolysis liquid that this comparative example is obtained uses efficient liquid phase chromatographic analysis, wherein Oligomeric manna sugar (sweet dew two
Sugar, manninotriose, mannotetrose) total concentration is 9.5g/L, wherein mannobiose is 6.9g/L, and manninotriose 2.6g/L do not have
Detect mannotetrose.Oligomeric manna sugar total yield, mannobiose yield and manninotriose are substantially less than embodiment 1-3.
Total sugar content is 87.5% in Oligomeric manna sugar product made from this comparative example, substantially less than embodiment 1-3.
Comparative example 3
It takes the open country 6g Chinese honey locust amylose gelatine powder to be fitted into reaction kettle, 20mL 5M acetic acid is added, reacts 2h at 130 DEG C, obtains second
Acid degradation liquid；The degradation solution further obtains Oligomeric manna sugar by spray drying by vacuum concentration recycling acetic acid.
The acetolysis liquid that this comparative example is obtained uses efficient liquid phase chromatographic analysis, wherein Oligomeric manna sugar (sweet dew two
Sugar, manninotriose, mannotetrose) total concentration is 9.2g/L, wherein mannobiose is 3.5g/L, manninotriose 3.4g/L, sweet
Dew tetrose is 2.3g/L.Oligomeric manna sugar total yield, mannobiose yield and manninotriose are substantially less than embodiment 1-3.
Total sugar content is 72.5% in Oligomeric manna sugar product made from this comparative example, substantially less than embodiment 1-3.
Comparative example 4
This comparative example provides the preparation method of Oligomeric manna sugar, and the difference with embodiment 1, which is only that, is added 20mL5M hydrochloric acid,
2h is reacted at 130 DEG C, obtains acetic acid degradation solution；The degradation solution is by vacuum concentration recycling acetic acid, further by doing by spraying
Dry acquisition Oligomeric manna sugar.
The hydrochloric acid hydrolyzate that this comparative example is obtained uses efficient liquid phase chromatographic analysis, wherein Oligomeric manna sugar (sweet dew two
Sugar, manninotriose, mannotetrose) total concentration is 9.3g/L, wherein mannobiose is 7.4g/L, and manninotriose 0.1g/L do not have
Detect mannotetrose.Oligomeric manna sugar total yield, mannobiose yield and manninotriose are substantially less than embodiment 1-3.
Total sugar content is 90.6% in Oligomeric manna sugar product made from this comparative example, is lower than embodiment 1-3.
Although above the present invention is described in detail with a general description of the specific embodiments,
On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, fall within the scope of the claimed invention without departing from theon the basis of the spirit of the present invention.
Claims (10)
1. a kind of preparation method of Oligomeric manna sugar characterized by comprising galactomannans solution is carried out high-pressure fluid
Then the homogeneous processing of nanometer is added acetic acid and carries out degradation reaction；Alternatively, further comprise depressurized after degradation reaction it is dense
It retracts and receives acetic acid, obtain Oligomeric manna sugar after concentrate is spray-dried.
2. preparation method according to claim 1, which is characterized in that the high-pressure fluid nanometer homogenization pressure is 190-
210MPa, preferably 200MPa；More preferable homogeneous 2-3 times.
3. preparation method according to claim 1 or 2, which is characterized in that acetic acid concentration used is 2-6M, degradation reaction temperature
Preferably 120-140 DEG C of degree, the degradation reaction preferred time is 1-4h.
4. preparation method according to claim 3, which is characterized in that acetic acid concentration used is 5-6M, degradation reaction temperature
It is 120-130 DEG C, the degradation reaction time is 1-2h.
5. preparation method according to claim 1-4, which is characterized in that acetic acid and galactomannans used
Mass ratio is 0.7:1-1.5:1, preferably 1.2:1-1.5:1.
6. preparation method according to claim 1-5, which is characterized in that the galactomannans solution it is dense
Degree is 80-100g/L.
7. preparation method according to claim 1-6, which is characterized in that prepare the original of the galactomannans
Material is wild Chinese honey locust.
8. preparation method according to claim 1-7, which is characterized in that the system of the galactomannans solution
Preparation Method includes: that wild Chinese honey locust or wild Chinese honey locust amylose gelatine powder are dissolved hydration 2-4h in 60-80 DEG C of water, centrifugation point after hydration
From supernatant is taken, then plus isometric dehydrated alcohol is centrifugated after alcohol precipitation, suitable quantity of water is added in precipitating, galactomannan is made
Glycan solution.
9. preparation method according to claim 8, which is characterized in that wild Chinese honey locust or wild Chinese honey locust polysaccharide in the hydration reaction
The weight ratio of rubber powder and water is 1%-3%；Preferably, the temperature of the hydration reaction is 70 DEG C, hydration time 3h, when alcohol precipitation
Between be 2h.
10. the Oligomeric manna sugar of any one of claim 1-9 the method preparation.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111549081A (en) * | 2020-04-16 | 2020-08-18 | 北京林业大学 | Method for catalytically degrading polysaccharide by seawater and composite oligosaccharide |
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| CN111549081A (en) * | 2020-04-16 | 2020-08-18 | 北京林业大学 | Method for catalytically degrading polysaccharide by seawater and composite oligosaccharide |
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