CN101891837A - Carboxymethylation bifidobacterium exopolysaccharide, preparation method thereof and application thereof - Google Patents
Carboxymethylation bifidobacterium exopolysaccharide, preparation method thereof and application thereof Download PDFInfo
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Abstract
The invention discloses carboxymethylation bifidobacterium exopolysaccharide and a preparation method thereof, and belongs to the technical field of the modification of exopolysaccharide. A symmetrical stretching vibration characteristic peak and an antisymmetric stretching vibration characteristic peak, which have wave numbers of 1,600 and 1,420, of carboxyls (COO-) in carboxymethyl exist in an infrared spectrum of the exopolysaccharide, wherein the carboxymethyl content is between 10 and 21 percent, the degree of substitution is between 0.35 and 0.72 percent, and the weight-average molecular weight is (0.8-1.2)*10<5> Da. The preparation method comprises the following steps of: reacting bifidobacterium exopolysaccharide with chloroacetic acid in aqueous solution of NaOH, neutralizing by using glacial acetic acid until the pH is 7.0, and filtering, dialyzing, concentrating, precipitating and washing to obtain the carboxymethylation bifidobacterium exopolysaccharide. The invention also discloses application of the carboxymethylation bifidobacterium exopolysaccharide in the preparation of immune regulation health-care products or immune regulation medicaments. In-vitro experiments of the carboxymethylation bifidobacterium exopolysaccharide show that the exopolysaccharide can improve the level of cell factors of IL-2 and IFN gamma in mouse spleen cells obviously, and the immune regulation capability is much higher than that of unmodified bifidobacterium exopolysaccharide.
Description
Technical field
The invention belongs to exocellular polysaccharide modification technology field, be specifically related to a kind of Carboxymethylation bifidobacterium exopolysaccharide and preparation method thereof and its application.
Background technology
Genus bifidobacterium (Bifidobacterium) has generally acknowledged security, it is the dominant microflora in the healthy animal digestive tube, aboundresources, of a great variety, and to the host bring into play biological barrier, nutrition, immunity, control endotoxemia, delay senility, physiological action such as antitumor.Along with research is day by day goed deep into, it is found that many apparent characteristics of bifidus bacillus and function are all relevant with its meta-bolites, and its meta-bolites research is had crucial meaning.
Polysaccharide is meant the saccharide compound of being made up of 20 above monose, it is one of important biomacromolecule of organism, become a kind of information carrier of tool glamour because of its changeable structure, have immunomodulatory, antitumor, anti-ageing, reducing blood-fat, hypoglycemic, anti-inflammatory, physiological function such as antiviral, and become the research and development emphasis of modern biology, medicine, food, chemical industry gradually, have very big development potentiality.Wherein, immunomodulatory class polysaccharide be research at most, the widest polysaccharide of clinical application, also be the polysaccharide of tool Application and Development potentiality.
Physiologically actives such as that the milk-acid bacteria exocellular polysaccharide has is antitumor, immunomodulatory, not only matter structure and the local flavor to milk-product has material impact, and might become one of protective foods good source, be widely used in thickening, stable, emulsification, the gelling of various food and preserve moisture.Bifidus bacillus is a kind of of milk-acid bacteria; have very high security and application potential, (exopolysaccharide EPS) is one of its important meta-bolites to exocellular polysaccharide; in order to improve and to protect active polysaccharide, the research of its structural modification aspect that very big progress has also been arranged.Mainly comprise the part degraded, selenic acid esterification, sulphating, partial acetylation, carboxymethylation, carboxyethylation of main chain, polyhydroxylated, branched modified etc. for the modification of polysaccharide physiologically active.Along with the development of modern biotechnology, genetic engineering technique, enzyme process technology and part physical means also are used to polysaccharide structures is modified, and be to strengthen its physiologically active, especially comparatively deep at immunostimulant and anti-tumor aspect research.For example, Jamas etc. introduce foreign gene to a strain wild yeast bacterium, and its intracellular polyse structure is changed, side chain glycosyl substitution value brings up to 0.5 from 0.2, and space conformation becomes and more unfolds, and the ratio of single coil configuration improves, and the polysaccharide anti tumor activity in vitro improves about 35 times than before modifying; Reports such as Stahmann, a kind of have a β-1, and the fungus polysaccharide of 3-D-glucan structure is through after the long supersound process, and molecular weight is reduced to about 50,000 from 250,000, through the Small angle X light diffracting analysis, the space structure of its ultrasonic degradation product is similar to the schizophan with immunoregulatory activity; Demleitner etc. are research object with curdlan, having carried out with D-semi-lactosi, D or L-arabinose and their oligose separately is substituent branched modified, and studying its anti-tumor activity respectively, the result shows that D-glucose is that the curdlan derivatives active of side chain is the highest.
Owing to can improve active polysaccharide through modifying, so research in this respect becomes the focus of paying close attention in recent years gradually both at home and abroad.The domestic and international license situation of this technology is as follows:
The sulphating lycium barbarum polysaccharide, the sulphating Agaricus Blazei Murrill polysaccharide, the sulphating bitter melon polysaccharide, the all existing patent of sulphating krestin and sulphating tea tree mushroom polysaccharide is declared, for example, Yan Hong, Yi Jianping: " controlling sulfate polyose and its production and application " (application number: 200510098339.0).
2006; the patent of gondola George Zuo Paidi, the top grade application of Paasche Kua Annaao Leix " high sulfated derivative of K5 polysaccharide and preparation method thereof " (application number: 200610127561.3) handle and eliminate oleophilic substance purification intestinal bacteria K5 polysaccharide by Virahol; can be used to prepare the high novel N of degree, the O-sulfated polysaccharides after the deacetylated effect of product process N-of purifying.
The domestic report that Sulfate of polysaccharideization is also arranged.2004, Zheng Weifa, storage is become a useful person, " extracellular polysaccharide sulfate of nitzschia closterium and preparation method thereof and application " (application number: earlier the Nitzschia closterium minutissima exocellular polysaccharide is mixed with methane amide earlier 200410090619.2), add esterifying reagent then and under condition of ice bath, carry out esterification, reactant is neutralized to pH6.8～7.2, use organic solvent deposit, the gained resolution of precipitate, dialysis promptly gets extracellular polysaccharide sulfate of nitzschia closterium, and prove that this exocellular polysaccharide sulfuric ester immunoregulatory activity has had significant raising, to the obvious suppression effect that is formed with of virus pneumonia and tumour.
Along with the development of physiological function structure effect research aspect, other modified methods are also introduced this technical field gradually.2004, at Liu Jianlin, Zhao Xuesong, " production of selenic acid polysaccharide " (application number: 200410067065.4) carrageenin is carried out the selenic acid esterification, formed the selenocarrageenan (Kappa-Selenocarrageenan) that a kind of organoselenium threshold value is stabilized in 50-100mg/g, controlled and repeated the phenomenon of uniting, formed the 1-dimention nano crystallization, sulfonic acid group is modified by the selenous acid group fully, reduced bio-toxicity, this invention synthetic k-selenocarrageenan has the advantages that toxicity is little, bioavailability is high; 2004, Meng Sheng, Zhong Wei are at " a kind of synthetic method of polysaccharide or derivatives thereof of phosphatide base group modification " (application number: reported 200410054022.2) that Phosphorylcholine etc. is had the group of bionic function by condensation reaction, be covalently bound on natural, the biodegradable natural polysaccharide molecular chain, be prepared into a kind of novel polysaccharide material that contains with the phosphatide base group modification; 2004, Yu Guangli is at " a kind of grifolan sulfuric ester and preparation method thereof and application " (application number: 200410023856.7) the Grifola frondosa water-insoluble polysaccharide is suspended in the organic solvent, add the alkali lye etherificate, add Mono Chloro Acetic Acid, temperature control carries out the carboxymethyl derivant good water solubility that sulfuric acid esterification prepares, the structure uniqueness, low price can be used for preparing immunomodulator and antitumor drug.But the research of relevant Bifodobacterium Exopolysaccharides and modified product thereof report is considerably less.The present invention is to the Bifodobacterium Exopolysaccharides modification, thereby a kind of modification Bifodobacterium Exopolysaccharides stronger than unmodified Bifodobacterium Exopolysaccharides immunomodulatory is provided.
Summary of the invention
The object of the present invention is to provide a kind of Carboxymethylation bifidobacterium exopolysaccharide.
Second purpose of the present invention is to provide the preparation method of above-mentioned Carboxymethylation bifidobacterium exopolysaccharide.
The 3rd purpose of the present invention is to provide a kind of composition that contains above-mentioned Carboxymethylation bifidobacterium exopolysaccharide.
The 4th purpose of the present invention is to provide the application of above-mentioned Carboxymethylation bifidobacterium exopolysaccharide.
A kind of Carboxymethylation bifidobacterium exopolysaccharide, the symmetry and the flexible vibrations of the unsymmetrically characteristic peak that have COO-in the carboxymethyl of 1600 wave numbers and 1420 wave numbers in the infrared spectra of this exocellular polysaccharide, carboxymethyl content is 10%-21% in the above-mentioned carboxymethyl Bifodobacterium Exopolysaccharides, substitution value is 0.35%-0.72%, and weight-average molecular weight is (0.8-1.2) * 10
5Da.Its preparation method is as follows:
(1) Bifodobacterium Exopolysaccharides is dissolved in the NaOH aqueous solution that concentration is 1.5-2.0moL/L, adds Mono Chloro Acetic Acid under the vigorous stirring, continue vigorous stirring in 40-80 ℃ and react 2-4h, wherein, Bifodobacterium Exopolysaccharides and chloroacetic mass ratio are 1: 5-15;
(2) reaction system of cooling step (1) is to room temperature, and being neutralized to pH with glacial acetic acid is 7.0, filters, and filtrate is used distill water dialysis 1d-2d again with the tap water 2d-3d that dialyses;
(3) concentrate dialysate adds 4～5 times of 95% ethanol sedimentation then and goes out exocellular polysaccharide to the 1/2-1/5 of original volume, uses dehydrated alcohol, each washing precipitation of acetone 2-3 time more successively, vacuum lyophilization precipitate the carboxymethyl Bifodobacterium Exopolysaccharides.
The raw material Bifodobacterium Exopolysaccharides of described Carboxymethylation bifidobacterium exopolysaccharide obtains by fermentation bifidobacterium asteroides (Bifidobacterium asteroides) BM-10CGMCC No.1355.Bifidobacterium asteroides (Bifidobacterium asteroides) BM-10 is preserved in China Committee for Culture Collection of Microorganisms common micro-organisms center (being called for short CGMCC) on April 13rd, 2005, and preserving number is CGMCC No.1355.This bacterial strain has been open in 200510105465.4 the patent at application number.The relevant method of utilizing this strain fermentation to prepare Bifodobacterium Exopolysaccharides is 200510105465.4 patent referring to application number.
The concentration of Bifodobacterium Exopolysaccharides in the NaOH aqueous solution is 4-20g/L described in the step (1).
The molecular weight cut-off of the used dialysis tubing of dialysis is 8000-12000Da in the step (2).
The measuring method of carboxymethyl content, substitution value and weight-average molecular weight in the carboxymethyl Bifodobacterium Exopolysaccharides is referring to following two document: Sun Ting, Lv Rongwen, Zhang Hongbing, photometric titration is measured the substitution value of carboxymethyl inulin, fine chemistry industry, 2007,24 volumes, 1 phase, 83-85; Zhang Yanping, modified starch manufacturing and application [M], Beijing: Chemical Industry Press, 2001,72.
A kind of is composition of active components with the Carboxymethylation bifidobacterium exopolysaccharide, also comprises one or more pharmaceutically acceptable carriers.Described carrier comprises thinner, vehicle, weighting agent, binding agent, wetting agent, disintegrating agent, tensio-active agent, absorption carrier, lubricant of pharmaceutical field routine etc.The formulation of described composition is the pharmaceutical field regular dosage form, comprises tablet, capsule, injection, freeze-dried powder, oral liquid, electuary etc.All can prepare by the pharmaceutical field ordinary method.
The application of above-mentioned Carboxymethylation bifidobacterium exopolysaccharide in preparation immunizing power adjusting healthcare products or medicine.
The chemical property of the carboxymethyl Bifodobacterium Exopolysaccharides that the present invention obtains is stable, and experiment in vitro shows that this exocellular polysaccharide can significantly improve the level of IL-2 in the mouse boosting cell, the IFN gamma cells factor, immunomodulatory power is apparently higher than unmodified Bifodobacterium Exopolysaccharides, and preparation method for extracellular polysaccharide of the present invention is simple.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and do not limit the present invention.
The preparation 1 of embodiment 1 Carboxymethylation bifidobacterium exopolysaccharide
(1) three groups of experiments is set, three parts of 2g Bifodobacterium Exopolysaccharidess are dissolved in respectively in the NaOH aqueous solution that concentration is 250mL, 2.0moL/L, add Mono Chloro Acetic Acid 10g, 20g, 30g under the vigorous stirring successively, under 60 ℃ of conditions, continue vigorous stirring reaction 3h;
(2) reaction system of cooling step (1) is to room temperature, and being neutralized to pH with glacial acetic acid is 7.0, filters, and filtrate is used distill water dialysis 1d-2d again with the tap water 2d-3d that dialyses;
(3) concentrate dialysate adds 4～5 times of 95% ethanol sedimentation then and goes out exocellular polysaccharide to 1/5 of original volume, uses dehydrated alcohol, each washing precipitation of acetone 2 times more successively, vacuum lyophilization precipitate the carboxymethyl Bifodobacterium Exopolysaccharides; The carboxymethylation of the carboxymethyl Bifodobacterium Exopolysaccharides that obtains the results are shown in Table 1.
Table 1 different material consumption is to the influence of Bifodobacterium Exopolysaccharides carboxymethylation degree and productive rate
The preparation 2 of embodiment 2 Carboxymethylation bifidobacterium exopolysaccharides
(1) three groups of experiments is set, three parts of 2g Bifodobacterium Exopolysaccharidess are dissolved in respectively in the NaOH aqueous solution that concentration is 250mL, 2.0moL/L, add Mono Chloro Acetic Acid 20g under the vigorous stirring respectively, three parts of reaction systems are placed respectively continue vigorous stirring reaction 3h under 40 ℃, 60 ℃, 80 ℃ the condition;
(2) reaction system of cooling step (1) is to room temperature, and being neutralized to pH with glacial acetic acid is 7.0, filters, and filtrate is used distill water dialysis 1d-2d again with the tap water 2d-3d that dialyses;
(3) concentrate dialysate adds 4～5 times of 95% ethanol sedimentation then and goes out exocellular polysaccharide to 1/4 of original volume, uses dehydrated alcohol, each washing precipitation of acetone 2 times more successively, vacuum lyophilization precipitate the carboxymethyl Bifodobacterium Exopolysaccharides; The carboxymethylation of the carboxymethyl Bifodobacterium Exopolysaccharides that obtains the results are shown in Table 2.
Table 2 differential responses temperature is to the influence of Bifodobacterium Exopolysaccharides carboxymethylation degree and productive rate
The preparation 3 of embodiment 3 Carboxymethylation bifidobacterium exopolysaccharides
(1) three groups of experiments is set, three parts of 2g Bifodobacterium Exopolysaccharidess are dissolved in respectively in the NaOH aqueous solution that concentration is 250mL, 2.0moL/L, add Mono Chloro Acetic Acid 20g under the vigorous stirring respectively, three parts of reaction systems are continued vigorous stirring reaction 2h, 3h and 4h respectively under 60 ℃ of conditions;
(2) reaction system of cooling step (1) is to room temperature, and being neutralized to pH with glacial acetic acid is 7.0, filters, and filtrate is used distill water dialysis 1d-2d again with the tap water 2d-3d that dialyses;
(3) concentrate dialysate adds 4～5 times of 95% ethanol sedimentation then and goes out exocellular polysaccharide to 1/4 of original volume, uses dehydrated alcohol, each washing precipitation of acetone 2 times more successively, vacuum lyophilization precipitate the carboxymethyl Bifodobacterium Exopolysaccharides; The carboxymethylation of the carboxymethyl Bifodobacterium Exopolysaccharides that obtains the results are shown in Table 3.
The table 3 differential responses time is to the influence of Bifodobacterium Exopolysaccharides carboxymethylation degree and productive rate
Embodiment 4 Carboxymethylation bifidobacterium exopolysaccharides are to the cultivation effect of mouse boosting cell cytokine
Mouse (Kunming kind SPF level mouse, male and female are not limit, body weight (18+2) g, 5 ages in week are available from Beijing Military Medical Science Institute) is put to death preparation splenocyte suspension, and regulate cell concn and reach 2.0 * 10
6Individual/mL; The Carboxymethylation bifidobacterium exopolysaccharide that unmodified raw material Bifodobacterium Exopolysaccharides and the embodiment of the invention 3 are made under the situation of reaction 3h is dissolved in respectively that preparation concentration is the polysaccharide soln of 100 μ g/mL in the distilled water;
Every hole adds the above-mentioned cell suspension of 100 μ l and 100 μ l modifications (carboxymethylation) or unmodified Bifodobacterium Exopolysaccharides solution in 96 orifice plates, establishes the control group that does not add polysaccharide simultaneously.Every group of three of mensuration are parallel, place the CO2 incubator to cultivate 3d, measure IL-2 and IFN γ concentration with cytokine test kit (import packing, Shanghai Xi Tang bio tech ltd), the results are shown in Table 4.
The detected result of table 4 mouse boosting cell IL-2 and IFN γ (pg/mL)
*Compare p＜0.05 with control group;
*Compare p＜0.01 with control group.
The data of table 4 show, compare with control group, and the external immunocompetence of Bifodobacterium Exopolysaccharides is higher than unmodified Bifodobacterium Exopolysaccharides, can significantly improve the concentration of IL-2, the IFN gamma cells factor, show external immunocompetence.
Claims (8)
1. Carboxymethylation bifidobacterium exopolysaccharide, it is characterized in that, the symmetry and the flexible vibrations of the unsymmetrically characteristic peak that have COO-in the carboxymethyl of 1600 wave numbers and 1420 wave numbers in the infrared spectra of described Carboxymethylation bifidobacterium exopolysaccharide, carboxymethyl content in the above-mentioned Carboxymethylation bifidobacterium exopolysaccharide is 10%-21%, substitution value is 0.35%-0.72%, and weight-average molecular weight is (0.8-1.2) * 10
5Da.
2. according to claim 1 described Carboxymethylation bifidobacterium exopolysaccharide, it is characterized in that the raw material Bifodobacterium Exopolysaccharides of described Carboxymethylation bifidobacterium exopolysaccharide obtains by fermentation bifidobacterium asteroides (Bifidobacterium asteroides) BM-10CGMCC No.1355.
3. the preparation method of the described Carboxymethylation bifidobacterium exopolysaccharide of claim 1 is characterized in that, carries out according to following operation steps:
(1) Bifodobacterium Exopolysaccharides is dissolved in the NaOH aqueous solution that concentration is 1.5-2.0moL/L, adds Mono Chloro Acetic Acid under the vigorous stirring, continue vigorous stirring in 40-80 ℃ and react 2-4h, wherein, Bifodobacterium Exopolysaccharides and chloroacetic mass ratio are 1: 5-15;
(2) reaction system of cooling step (1) is to room temperature, and being neutralized to pH with glacial acetic acid is 7.0, filters, and filtrate is used distill water dialysis 1d-2d again with the tap water 2d-3d that dialyses;
(3) concentrate dialysate adds 4～5 times of 95% ethanol sedimentation then and goes out exocellular polysaccharide to the 1/2-1/5 of original volume, uses dehydrated alcohol, each washing precipitation of acetone 2-3 time more successively, vacuum lyophilization precipitate the carboxymethyl Bifodobacterium Exopolysaccharides.
4. the preparation method of Carboxymethylation bifidobacterium exopolysaccharide according to claim 3 is characterized in that, the concentration of Bifodobacterium Exopolysaccharides in the NaOH aqueous solution is 4-20g/L described in the step (1).
5. the preparation method of Carboxymethylation bifidobacterium exopolysaccharide according to claim 3, it is characterized in that described Bifodobacterium Exopolysaccharides obtains by fermentation bifidobacterium asteroides (Bifidobacterium asteroides) BM-10CGMCC No.1355.
6. one kind is composition of active components with the described Carboxymethylation bifidobacterium exopolysaccharide of claim 1.
7. the application of the described Carboxymethylation bifidobacterium exopolysaccharide of claim 1 in preparation immunizing power adjusting medicine.
8. the application of the described Carboxymethylation bifidobacterium exopolysaccharide of claim 1 in preparation immunizing power adjusting healthcare products.
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| CN102154183A (en) * | 2011-03-07 | 2011-08-17 | 中国农业大学 | Bifidobacterium animalis extracellular polysaccharide and preparation method thereof |
| CN102181505A (en) * | 2011-01-31 | 2011-09-14 | 温州医学院 | Method for separating and purifying bifidobacterium polysaccharide |
| CN103012610A (en) * | 2012-12-04 | 2013-04-03 | 浙江大学 | Carboxymethylated Enterobacter cloacae polysaccharide, its preparation method and application |
| CN104059161A (en) * | 2014-06-25 | 2014-09-24 | 上海市农业科学院 | Pleurotus eryngii leftover crude polysaccharide and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102181505A (en) * | 2011-01-31 | 2011-09-14 | 温州医学院 | Method for separating and purifying bifidobacterium polysaccharide |
| CN102154183A (en) * | 2011-03-07 | 2011-08-17 | 中国农业大学 | Bifidobacterium animalis extracellular polysaccharide and preparation method thereof |
| CN102154183B (en) * | 2011-03-07 | 2012-11-28 | 中国农业大学 | Bifidobacterium animalis extracellular polysaccharide and preparation method thereof |
| CN103012610A (en) * | 2012-12-04 | 2013-04-03 | 浙江大学 | Carboxymethylated Enterobacter cloacae polysaccharide, its preparation method and application |
| CN103012610B (en) * | 2012-12-04 | 2015-05-20 | 浙江大学 | Carboxymethylated Enterobacter cloacae polysaccharide, its preparation method and application |
| CN104059161A (en) * | 2014-06-25 | 2014-09-24 | 上海市农业科学院 | Pleurotus eryngii leftover crude polysaccharide and preparation method thereof |
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