CN104788581B - It is a kind of to improve the water miscible Sulfation method of yeast β D glucosans - Google Patents
It is a kind of to improve the water miscible Sulfation method of yeast β D glucosans Download PDFInfo
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Abstract
The present invention relates to a kind of improve the water miscible Sulfation method of yeast β D glucosans, comprise the steps：1) with yeast β D glucosans as raw material, it is dissolved in the dimethyl sulphoxide solution containing carbamide, after stirring and dissolving, obtains solution a；2) the solution a is placed in ice bath, after supersound process, is still placed in ice bath, is slowly added dropwise containing H while stirring2SO4DMSO solution obtain solution b；3) solution b is placed in oil bath constant temperature oscillator carries out esterification, solution after esterification is quickly cooled to into room temperature, and adds deionized water, after dilution, cross polyester membrane microfiltration, then Jing hyperfiltration treatment, concentration and Sulfation yeast β D glucosans described in drying to obtain successively.The present invention utilizes ultrasonic in combination Sulfation method, the yeast β D glucosans prepared have the advantages that dissolubility is good, production security is high, applied range, can effective enhancing human body immunity function.
Description
Technical field
The present invention relates to food processing field, more particularly to a kind of water miscible Sulfation of raising yeast callose
Preparation method.
Background technology
In recent years, substantial amounts of research confirms that callose has enhancing immunity, antitumor, antibacterial and healing of wound etc. aobvious
The physiological function of work, increasingly causes people's growing interest.However, yeast callose is in neutrality, in aggregation shape, do not dissolve in
Water, is slightly dissolved in DMSO, and this seriously constrains its application industrially.
Yeast callose water solublity is relevant with the degree of polymerization, degree of branching and chemical modification etc., improves its deliquescent side
Method mainly has two big class of physical method and chemical method, specially：
Physical method：To yeast callose physical modification Jing frequently with mainly ultrasonic method, Ozone and peroxide
Change hydrogen method.But it is individually not notable for the dissolubility effect for increasing yeast callose with ultrasonic method process, and with smelly
Soluble yeast callose range of molecular weight distributions width prepared by the oxidation degradation method such as oxygen method and hydrogen peroxide method, and easily draw
Enter the impurity such as oxidant.
Chemical method：Chemical modification method may significantly increase the dissolubility of callose, but can change its natural structure,
Its biological activity is caused to lower or raise.Solubilising is carried out by carboxymethylated method to be modified to yeast callose, can be increased
Plus its water solublity, but carboxy methylation does not have the effect of Sulfation obvious the enhancing of yeast callose physiologically active.
Dextran sulfate has an extensive biological property because of which, including antiviral, antitumor, anticoagulating active etc., close
There is following report in the method for dextran sulfate：
Huang Guohong has write yeast β -1,3-D Portugals exactly in yeast β -1, one text of research of 3-D dextran sulfate preparation technologies
The preparation method of polysaccharide sulfuric ester, specially：0.3g yeast β -1 is weighed, 3-D glucosans add 10mL diformazans in conical flask
Base Methanamide, is vigorously mixed at room temperature for, and yeast β -1,3-D glucosans is fully suspended in dimethylformamide, then by
Gradually add chlorosulfonic acid concentration 15% esterifying agent 15mL, stirring reaction 3h at 60 DEG C, reaction terminate after, pour into immediately
In the frozen water of 100mL, pH7.2 being neutralized to 10% sodium hydroxide, adding the dehydrated alcohol of 3-5 times of volume, stood, centrifugation will
Precipitation tap water stalks 48h, distilled water dialysis 24h, freeze-dried yeast β -1 for obtaining white of dialysis solution, 3-D glucosans
Sulfuric ester (Huang Guohong, yeast β -1, the research of 3-D dextran sulfate preparation technologies, food industry science and technology, 2009,30 (08)：
261-263)
CN99116588.8 (CN1283632A) discloses the ganoderic alpha with anti-tumor activity-(1 → 3)-D- Portugals and gathers
Sugar sulfate derivant and application thereof and preparation method, wherein, the derivant is ganoderic alpha-(1 → 3)-D- dextran sulfates
The preparation method for changing derivant includes：It is sub- that α-(1 → 3)-D- glucosans are dissolved in the dimethyl containing 0.25MLiCl by the method
In sulfone mixed solvent, add sulfonated reagent (24mL pyridines being added drop-wise to for 4.9mL chlorosulfonic acids as described in Example 1) under agitation,
Reflection 4-6 hours, are finally neutralized to neutrality with sodium hydrate aqueous solution, are washing with acetone precipitation and with acetone/water mixed solution
After washing, that is, obtain the sulfate derivative of polysaccharide.
And the process of sulfating of routine is such as：Chlorosulfonic acid-pyridine method, chlorosulfonic acid-Methanamide method etc. is generally using chlorosulfonic acid etc.
Poisonous reagent is esterifying agent.And in normal propyl alcohol heterogeneous system, esterification is carried out by esterifying agent of sulphuric acid, though can be easily separated
The yeast callose sulfuric ester for generating is obtained, but product yield is only 37.4% (w/w), and reaction is in heterogeneous system
In carry out, the general substitution value of yeast callose soluble derivative of preparation is low and distributing inhomogeneity.Adopt in this patent
Dimethyl sulfoxide be a kind of micro- toxicant, its toxicity is well below poisonous reagents such as chlorosulfonic acids.Have not yet to see a kind of profit
The report of yeast callose dissolubility method is effectively improved with ultrasonic in combination Sulfation method
The content of the invention
What the purpose of the present invention was is to provide a kind of water miscible Sulfation method of raising yeast callose, the party
Method adopts supersound process and Sulfation to combine, and carries out modification to yeast callose, is remarkably improved β-D- Portugals and gathers
Sucrose solution dissolubility.
One kind provided by the present invention improves the water miscible Sulfation method of yeast callose, including following step
Suddenly：
1) with yeast callose as raw material, it is dissolved in the dimethyl sulphoxide solution containing carbamide, after stirring and dissolving
To solution a；
2) the solution a is placed in ice bath, after supersound process, is still placed in ice bath, is slowly added dropwise while stirring and contains
There is H2SO4DMSO solution obtain solution b；
3) solution b is placed in oil bath constant temperature oscillator carries out esterification, and the solution after esterification is quickly cooled to room temperature,
And add deionized water, after dilution, cross polyester membrane microfiltration, then Jing hyperfiltration treatment, concentration and sulfuric ester described in drying to obtain successively
Change yeast callose.
In said method：
Step 1) in：
In the dimethyl sulphoxide solution containing carbamide, urea content is 4-6M；
The yeast callose raw material is 1 with the quality volume g/ml ratio of urea-containing dimethyl sulphoxide solution：20-
25；
Step 2) in
The ultrasound works frequency range is 15-20KHz, and power bracket is 200-400W, circular treatment time 20s,
Have a rest time 5s, circulates 10-12 time；
Containing H2SO4DMSO solution in be containing 5%H2SO4DMSO solution；
In the solution b, solution a with contain H2SO4The volume ratio of DMSO solution be：1：1.
Step 3), the temperature of the oil bath constant temperature oscillator is 100 DEG C, and rotating speed is 100rpm, and the time is 2-3h；
Solution deionized water after the esterification adds to 500-800 times of volume ml of yeast callose weight g；
The pore size of the polyester film is 0.8 μm；
The ultrafiltration is comprised the following steps：The use of the volume ratio of deionized water and solution e is 25：1, operating pressure is
0.15Mpa, temperature are 35 DEG C, circular treatment 10 times；
Molecular size range after ultrafiltration can be：10,000；
During the concentration for the 1/10 of original volume；
The drying mode is spray drying.
Preferably, the Sulfation method, comprises the steps：
1) with yeast callose as raw material, it is dissolved in the dimethyl sulphoxide solution containing 5M carbamide, after stirring and dissolving
Solution a is obtained, wherein yeast callose raw material and the quality volume g/ml ratio of urea-containing dimethyl sulphoxide solution are 1：
20-25；
2) the solution a is placed in ice bath, after supersound process, is placed in ice bath, be slowly added dropwise while stirring containing
5%H2SO4DMSO solution obtain solution b, ultrasound works frequency range is 15-20KHz, and power bracket is 200-400W, circulation
Process time 20s, intermittent time 5s, circulate 10-12 time, solution a with contain H2SO4DMSO solution volume ratio be 1：1；
3) solution b is placed in oil bath constant temperature oscillator carries out esterification, and temperature is 100 DEG C, and rotating speed is 100rpm, instead
It is 2-3h between seasonable, the solution after esterification is quickly cooled to into room temperature, and adds the amount of deionized water to solution poly- for yeast β-D- Portugals
500-800 times of volume ml of sugar weight g, then 0.8 μm of polyester membrane microfiltration excessively, then Jing hyperfiltration treatment, concentration and drying successively, i.e.,
Obtain the Sulfation yeast callose.
Present invention also offers the yeast callose that above-mentioned Sulfation method is prepared, its callose
Substitution value is 0.51, and yield is 90.12%.
The preparation method of the yeast callose that the present invention is provided has the advantage that：
1st, in method：
The yeast callose prepared using ultrasonic in combination Sulfation method is soluble in water, applied range；
Sulfation is modified and solubilized to add carbamide to carry out as the homogeneous system being esterified using dimethyl sulfoxide, and its toxicity is remote
Less than poisonous reagents such as the utilization chlorosulfonic acids for generally adopting for esterifying agent, operational risk is reduced；
The yeast callose sulfuric ester prepared using the method has functions that to strengthen immunity, and wherein Jing high pressure is micro- penetrates
Yeast callose derivant after stream process and Sulfation is to the thin conversion ratio of Con A inducing mouse lymphs, mice serum
Middle total complement hemolytic activity (CH50) and NK cells in mice activity are respectively provided with pole significant difference (P≤0.01).
2nd, the comprehensive utilization of the achievable industrial by-products waste beer yeast of the present invention, increase industrial by-products utilization rate and
Surcharge, with great economic benefit and environment protection significance.
Specific embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
In following embodiments, material used, reagent etc., if no special instructions, commercially obtain.
Data processing of following embodiments per step is completed using DPS softwares.
Embodiment 1, the water miscible Sulfation method of raising yeast callose
1) 100g yeast calloses are dissolved in the DMSO (carbamide containing 5M) of 2L, after stirring and dissolving, obtain solution
a。
2) solution a is placed in ice bath, under operating frequency 20KHz, supersound process is carried out with the power of 400W, is often circulated
Process time 20s, intermittent time 5s, circulate 10 times, the solution after ultrasound is placed in ice bath, be slowly added dropwise while stirring containing
5%H2SO4DMSO 2L (solution a with contain 5%H2SO4DMSO volume ratio be 1：1, similarly hereinafter), obtain solution b.
3) solution b is placed in 100 DEG C of oil bath constant temperature oscillator, esterification is carried out under the rotating speed of 100rpm, instead
After answering 2h, reactant liquor is quickly cooled to room temperature, and adds deionized water to 80L, cross 0.8 μm of polyester membrane microfiltration, it is not anti-to remove
The yeast callose microgranule answered, the sulfuric ester yeast callose after filtration carry out ultrafiltration (Mw=10,000) process,
Circular treatment 2000L deionized water, finally, permeate is concentrated into 8L, is spray-dried to obtain Sulfation yeast callose.
Embodiment 2, the water miscible Sulfation method of raising yeast callose
1) 500g yeast calloses are dissolved in the DMSO (carbamide containing 5M) of 12.5L, after stirring and dissolving, obtain molten
Liquid a.
2) solution a is placed in ice bath, under operating frequency 18KHz, supersound process is carried out with the power of 400W, is often circulated
Process time 20s, intermittent time 5s, circulate 12 times, the solution after ultrasound is placed in ice bath, be slowly added dropwise while stirring containing
5%H2SO4DMSO 12.5L, obtain solution b.
3) solution b is placed in 100 DEG C of oil bath constant temperature oscillator, esterification is carried out under the rotating speed of 100rpm, instead
After answering 3h, reactant liquor is quickly cooled to room temperature, and adds deionized water to 250L, cross 0.8 μm of polyester membrane microfiltration, it is not anti-to remove
The yeast callose microgranule answered.Sulfuric ester yeast callose after filtration carry out ultrafiltration (Mw=10,000) process,
Circular treatment 6250L deionized water, finally, permeate is concentrated into 25L, is spray-dried to obtain Sulfation yeast callose.
Embodiment 3, the water miscible Sulfation method of raising yeast callose
1) 800g yeast calloses are dissolved in the DMSO (carbamide containing 5M) of 18L, after stirring and dissolving, obtain molten
Liquid a.
2) solution a is placed in ice bath, under operating frequency 15KHz, supersound process is carried out with the power of 400W, is often circulated
Process time 20s, intermittent time 5s, circulate 11 times, the solution after ultrasound is placed in ice bath, be slowly added dropwise while stirring containing
5%H2SO4DMSO 18L, obtain solution b.
3) solution b is placed in 100 DEG C of oil bath constant temperature oscillator, esterification is carried out under the rotating speed of 100rpm, instead
After answering 2.5h, reactant liquor is quickly cooled to room temperature, and adds deionized water to 480L, cross 0.8 μm of polyester membrane microfiltration, to remove not
The yeast callose microgranule of reaction.Sulfuric ester yeast callose after filtration carries out ultrafiltration (Mw=10,000) place
Reason, circular treatment 9000L deionized water, finally, permeate is concentrated into 50L, be spray-dried Sulfation yeast β-D- Portugals gather
Sugar.
Comparative example 1, the water miscible Sulfation method of raising yeast callose
1) 2.0g yeast calloses are dissolved in the DMSO (carbamide containing 6M) of 50mL, after stirring and dissolving, obtain molten
Liquid a.
2) solution a is placed in ice bath, is slowly added dropwise containing 5%H while stirring2SO4DMSO50mL, obtain solution b.
3) solution b is placed in 100 DEG C of oil bath constant temperature oscillator, esterification is carried out under the rotating speed of 100rpm, instead
After answering 4h, reactant liquor is quickly cooled to room temperature, and adds deionized water 2L, cross 0.8 μm of polyester membrane microfiltration, it is unreacted to remove
Yeast callose microgranule.Sulfuric ester yeast callose after filtration carries out ultrafiltration, and (Mw=10,000) is processed, circulation
40L deionized waters are processed, finally, permeate is concentrated into 200mL, is spray-dried to obtain Sulfation yeast callose.
Experimental example：
1st, embodiment 1-3, comparative example 1 are investigated, observes its character, detect its substitution value, wherein, the tool of substitution value
Body detecting method is：
In the homogeneous system of Urea-DMSO after ultrasound exposure, with sulphuric acid as esterifying agent, yeast callose is entered
The process of row sulphation, sulfuric acid concentration 5% (v/v) react 2-3h at 100 DEG C；
The substitution value for calculating esterification callose adopts nephelometry.Sulfate is discharged by rear and barium with 8%TCA
Ion forms muddiness in gelatin, under wavelength 360nm determines turbidity, makees reference material with potassium sulfate and obtains after standard curve, meter
Calculate sulfate content.
Substitution value DS is calculated：
S%：The percentage composition of sulfate group.
2nd, result of the test is shown in Table 1.
Table 1：Testing result
As a result show：The final products obtained in embodiment are off-white powder, and are esterified the replacement of callose
Degree is respectively 0.48,0.51 and 0.50；Yield is respectively 89.97%, 90.12% and 90.05%.Substitution value in comparative example 1
For 0.43, yield is 87.97%.Compared with comparative example 1, embodiment 1,2,3 is no matter excellent in substitution value or in terms of yield
In comparative example 1.
As a result show：The Sulfation method that the present invention is provided has the high advantage of substitution value and yield.
Although above having used general explanation, specific embodiment and test, the present invention having been made to retouch in detail
State, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Scope.
Claims (1)
1. it is a kind of to improve the water miscible Sulfation method of yeast callose, comprise the steps：
1) with yeast callose as raw material, it is dissolved in the dimethyl sulphoxide solution containing carbamide, after stirring and dissolving, obtains molten
Liquid a；
2) the solution a is placed in ice bath, after supersound process, is still placed in ice bath, be slowly added dropwise while stirring containing
H2SO4DMSO solution obtain solution b；
3) solution b is placed in oil bath constant temperature oscillator carries out esterification, the solution after esterification is quickly cooled to room temperature, and is added
Deionized water, after dilution, cross polyester membrane microfiltration, then successively Jing hyperfiltration treatment, concentration and drying to obtain Sulfation yeast β-
D- glucosans；
Step 1) in：In the dimethyl sulphoxide solution containing carbamide, urea content is 4-6M；
Step 1) in：Yeast callose raw material is 1 with the quality volume g/ml ratio of urea-containing dimethyl sulphoxide solution：
20-25；
Step 2) in, the ultrasound works frequency range is 15-20KHz, and power bracket is 200-400W, the circular treatment time
20s, intermittent time 5s, circulate 10-12 time；
Step 2) in：It is described containing H2SO4DMSO solution be containing 5%H2SO4DMSO solution；
Step 2) in：In the solution b, solution a with containing 5% H2SO4DMSO solution volume parts ratio be：1：1；
Step 3) in：In the esterif iotacation step, the temperature of oil bath constant temperature oscillator is 100 DEG C, and rotating speed is 100rpm, esterification time
For 2-3h；
Step 3) in：In the dilution step, the b solution after esterification with the volume ratio of deionized water is：1：20；The polyester film
Pore size be 0.8 μm；
Step 3) in：The ultrafiltration is 25 using the volume ratio of solution after deionized water and dilution：1, operating pressure is
0.15MPa, temperature are 35 DEG C, circular treatment 10 times, and the molecular size range after ultrafiltration is：10,000.
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| CN111690075B (en) * | 2019-03-15 | 2021-10-15 | 中国海洋大学 | Water-soluble beta-glucan, preparation method thereof and application thereof in preparation of immune enhancement and anti-tumor medicines and health-care products |
| CN110128565B (en) * | 2019-05-06 | 2021-02-26 | 上海市农业科学院 | Ganoderma beta-glucan sulfate and synthesis method and application thereof |
| CN118679189A (en) * | 2022-02-10 | 2024-09-20 | 日东电工株式会社 | Process for producing beta-1, 3-glucan derivative |
| CN115746163A (en) * | 2022-11-07 | 2023-03-07 | 中国海洋大学 | Sulfated beta-glucan, preparation method and application thereof in immunoprotection and antitumor drugs |
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| CN102633903A (en) * | 2012-05-10 | 2012-08-15 | 哈尔滨工业大学 | Yeast glucan sulfated derivative with gamma ray radiation protection function, manufacturing method of yeast glucan fulfated derivative with gamma ray radiation protection function |
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| CN102633903A (en) * | 2012-05-10 | 2012-08-15 | 哈尔滨工业大学 | Yeast glucan sulfated derivative with gamma ray radiation protection function, manufacturing method of yeast glucan fulfated derivative with gamma ray radiation protection function |
| CN103059161A (en) * | 2013-01-06 | 2013-04-24 | 中国农业科学院农产品加工研究所 | Method for improving yeast beta-D-glucan water-solubility |
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Inventor after: Liu Hongzhi Inventor after: Wang Qiang Inventor after: Liu Li Inventor after: Shi Aimin Inventor after: Hu Hui Inventor after: Yu Miao Inventor after: Lin Weijing Inventor after: Liu Xiaoyong Inventor after: Li Yanan Inventor before: Wang Qiang Inventor before: Liu Hongzhi Inventor before: Liu Li Inventor before: Shi Aimin Inventor before: Hu Hui Inventor before: Yu Miao Inventor before: Lin Weijing Inventor before: Liu Xiaoyong Inventor before: Li Yanan |