CN101941994B - Method for preparing selenium manno-oligosaccharide - Google Patents
Method for preparing selenium manno-oligosaccharide Download PDFInfo
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- CN101941994B CN101941994B CN201010259989A CN201010259989A CN101941994B CN 101941994 B CN101941994 B CN 101941994B CN 201010259989 A CN201010259989 A CN 201010259989A CN 201010259989 A CN201010259989 A CN 201010259989A CN 101941994 B CN101941994 B CN 101941994B
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Abstract
The invention discloses a method for preparing a selenium manno-oligosaccharide. The selenium manno-oligosaccharide is prepared by reacting manno-oligosaccharide with seleninic acid under a certain condition, wherein the content of selenium in a product is 0.8 to 4.5mg/g. The method comprises the following steps of: under an acid environment, dropwise adding the solution of the seleninic acid into the solution of the manno-oligosaccharide for reaction at a certain temperature; adding FeCl3 solution so as to remove un-reacted seleninic acid; adding ethanol so as to precipitate the selenium manno-oligosaccharide; and washing the selenium manno-oligosaccharide for two times and drying at a low temperature to obtain the product. The analysis of ultraviolet scanning and infrared scanning on the product shows that the selenium manno-oligosaccharide still maintains the basic structure of oligosaccharide and the selenium may have two presence forms, namely a selenium-ester structure formed by performing esterification reaction on the selenium and hydroxy and a C-Se-H structure formed by ring opening at the position of a sugar ether bond.
Description
Technical field
The invention belongs to the organoselenium preparation field, be specifically related to a kind of preparation method of selenizing manna oligosaccharide.
Background technology
(Selenium is the trace element of needed by human Se) to selenium, is the main active ingredient of Selenoperoxidase, and it can remove oxyradical in the body directly or indirectly, can suppress lipid oxidation or peroxo-, can also improve and regulate immunologic function.Human body lacks selenium can cause fatal scarce selenium syndromes, like Keshan disease, mellitus, cardiovascular disorder, cataract, tumour, aging etc.If but the excessive middle toxicity syndrome such as alopecia, piptonychia that also can cause of the selenium of taking in.Selenium supplement agent can be inorganic selenium, organoselenium, biological activity selenium.Sodium Selenite is being obtained good result aspect prevention Kaschin-Beck disease and the reduction onset of liver cancer rate, yet Sodium Selenite directly uses toxicity bigger, and dosage is wayward, effectively absorption difference.In recent years, take the plant sprinkling or the soil application inorganic selenium is had report with the application that increases human body and livestock organoselenium source, the organic selenium content that still obtains is not high, and biological effect is indeterminate.A kind of organic selenium compounds-yeast rich in selenium has preparation, but product fraction is unstable, and selenium content is not high yet.Therefore the good necessary research and development of novel organoselenium of nontoxic utilizability.
Manna oligosaccharide (Manno-oligosaccharides) claim manna oligosaccharide again; It is unique new type functional oligose that can combine external source venereal bacteria in the enteron aisle; It is the enzyme liberating product of mannans material, extensively is present in Rhizoma amorphophalli powder, guar gum, sesbania gum and the multiple microorganism wall.It has good physicochemical property such as low in calories, stable, safety non-toxic, have reducing blood-fat, hypoglycemic, regulate important nourishing function such as stomach and enhancing immunity and anti-oxidant, remove important physiological function such as radical.
Patent CN101104644A discloses a kind of method for making and application thereof of polysaccharide monohydrate selenium dioxide ester; This method is that dextrin, Expex, pectinose sill sugar are joined in the pyridine with selemium oxyfluoride; Reacting by heating 0.1～100 hour; Obtain a kind of polysaccharide monohydrate selenium dioxide ester, this method long reaction time, and also selemium oxyfluoride is not easy to synthesize; Patent 200410071808.6 discloses a kind of selenizing polysaccharide and preparation method thereof, and this method is earlier synthetic selenous acid, selenous acid is reduced into selenic acid, and selenate radical is imported in the polysaccharide, and selenium content is 3mg～200mg/g in the product; Patent CN1284509A discloses chitosan selenite and preparation method thereof, and this method is that selenium content is 0～26% in the product with the selenous acid reaction of the amido of chitosan and adding; Patent CN101654486A discloses a kind of preparation method of astragalus polysaccharide selenide, and this method joins astragalus polysaccharides in the pyridine, adds then to contain seleno reagent SeOCl2 reaction for some time; Use absolute ethanol washing again, precipitate centrifugal, vacuum lyophilization; Finally obtain the lightpink astragalus polysaccharide selenide, selenium content is 15950 μ g/g in the product, but this legal system is equipped with the process complicacy; Preparation condition is harsh, and-toxicity of SeOCl2 is very big.Patent CN1560088A discloses a kind of preparation method of selenizing KGM; In a kind of Se6+ solution, add ethanol and hydrochloric acid, process selenylation reaction liquid, add KGM then; Process the selenizing KGM, selenium content is 125.4-197.3mg/Kg in the product.
Summary of the invention
The technical problem that the present invention will solve is: to the shortcoming and deficiency that prior art exists, the invention discloses a kind of preparation method of easy, reliable selenizing manna oligosaccharide, prepared selenizing manna oligosaccharide has higher health-care effect.
To above-mentioned technical problem, the present invention proposes following technical scheme:
1) selenous acid solution and the mass concentration of using deionized water to prepare 0.1g/mL respectively is 20% manna oligosaccharide solution;
2) manna oligosaccharide solution is placed the vibration tank, and to the HNO that wherein by every gram manna oligosaccharide dry powder adding 0-4ml volumetric concentration is 10%
3Solution slowly drips selenous acid solution then in manna oligosaccharide solution, and gets solution A in 30-80 ℃ of following oscillatory reaction 4-12 hour, and the volume ratio of selenous acid solution and manna oligosaccharide solution is 1-10: 5;
3) FeCl of the 1mol/L of adding capacity in reacted solution
3Solution is with the NH of pH=10
3-NH
4The Cl damping fluid transfers to 6～7 with pH value of solution, forms red-brown precipitation, and placement is spent the night;
4) supernatant is got in the mixed solution spinning under the condition of 3500r/min after placement is spent the night, and discards red-brown precipitation;
5) absolute ethyl alcohol of 2～3 times of volumes of adding supernatant in this supernatant places 4 ℃ of refrigerators to separate out the selenizing product, and deposition is got in spinning under the condition of 4000r/min, abandoning supernatant;
6) then to throw out with absolute ethanol washing twice, the centrifuging and taking throw out; In air seasoning below 50 ℃, obtain faint yellow selenizing manna oligosaccharide through pulverizing.
Beneficial effect of the present invention is embodied in: the preparation method of selenizing manna oligosaccharide according to the invention combines manna oligosaccharide with selenium; Easy reliable, good stability; Reaction product selenizing manna oligosaccharide still keeps the basic configuration of oligose, can avoid inorganic selenium to the toxic action that humans and animals uses the back to produce, and the selenium that is combined on the manna oligosaccharide is slowly discharged; Prolong the selenium residence time in vivo; Both keep the biological function of manna oligosaccharide according to the selenizing manna oligosaccharide of the method for the invention preparation, can bring into play the physiologically active of trace element-selenium again, simultaneously; Its function all promotes with respect to manna oligosaccharide and selenium to some extent; Through experiment showed, that the selenizing manna oligosaccharide all increases than the elimination efficiency of manna oligosaccharide to superoxide anion and hydroxy radical qiao, especially the elimination efficiency to hydroxy radical qiao improves very obvious.
The selenizing manna oligosaccharide has following function:
Detoxication and toxicant eliminating function: selenium has heavy metal element and aflatoxin degradations such as antagonism lead, mercury, cadmium, removes the function of internal metabolism refuse; Manna oligosaccharide has the function of adsorption of aflatoxin, also can clear up enteron aisle rubbish fast.The selenizing manna oligosaccharide can organically combine detoxifcation and functions of expelling toxin, accelerates the drainage of vivotoxin, refuse.
Cancer-resisting: selenium and manna oligosaccharide be ability enhance immunity function all; All have anti-oxidant, remove radical, promote that vivotoxin and metabolic waste are discharged, protection cell membrane integrity and antimutagenic effect, reduction carcinogens are active, the effects such as toxic side effect that reduce cancer therapy drug, so the selenizing manna oligosaccharide has good anti-cancer and kill cancer action.
Blood lipid-reducing blood sugar-decreasing: manna oligosaccharide has tangible blood lipid-reducing blood sugar-decreasing effect, and selenium has the effect of similar Regular Insulin, and the selenizing manna oligosaccharide is good antihypelipidemic product.It can produce propionic salt in the colonic fermentation, quickens glycolysis-; Bring into play the effect of similar Regular Insulin, quicken carbohydrate metabolism; Influence the enteron aisle hormonal readiness, regulate the absorption equilibrium of carbohydrate and fat.
Anti-ageing: the selenizing manna oligosaccharide can the enhancing body glutathione peroxidase and body in more than 20 kind of selenoenzyme and activity of proteins; Make cells in vivo, organize the physiologically active of avoiding peroxide injury and keeping body, can in time discharge vivotoxin and metabolic waste simultaneously.Therefore has tangible function in delaying senility.
Embodiment
Below in conjunction with embodiment the present invention is further specified.
Embodiment 1:
1) selenous acid solution and the mass concentration of using deionized water to prepare 0.1g/mL respectively is 20% manna oligosaccharide solution;
2) manna oligosaccharide solution is placed the vibration tank, in manna oligosaccharide solution, slowly drip selenous acid solution then, and got solution A in 9 hours in 50 ℃ of following oscillatory reactions, the volume ratio of selenous acid solution and manna oligosaccharide solution is 1: 5;
3) FeCl of the 1mol/L of adding capacity in reacted solution
3Solution is with the NH of pH=10
3-NH
4The Cl damping fluid transfers to 6～7 with pH value of solution, forms red-brown precipitation, and placement is spent the night;
4) supernatant is got in the mixed solution spinning under the condition of 3500r/min after placement is spent the night, and discards red-brown precipitation;
5) absolute ethyl alcohol of 2 times of volumes of adding supernatant in this supernatant places 4 ℃ of refrigerators to separate out the selenizing product, and deposition is got in spinning under the condition of 4000r/min, abandoning supernatant;
6) then to throw out with absolute ethanol washing twice, the centrifuging and taking throw out; In air seasoning below 50 ℃, obtain faint yellow selenizing manna oligosaccharide through pulverizing.
Embodiment 2:
1) selenous acid solution and the mass concentration of using deionized water to prepare 0.1g/mL respectively is 20% manna oligosaccharide solution;
2) manna oligosaccharide solution is placed the vibration tank, and to the HNO that wherein by every gram manna oligosaccharide dry powder adding 1ml volumetric concentration is 10%
3Solution slowly drips selenous acid solution then in manna oligosaccharide solution, and gets solution A in 12 hours in 30 ℃ of following oscillatory reactions, and the volume ratio of selenous acid solution and manna oligosaccharide solution is 4: 5;
3) FeCl of the 1mol/L of adding capacity in reacted solution
3Solution is with the NH of pH=10
3-NH
4The Cl damping fluid transfers to 6～7 with pH value of solution, forms red-brown precipitation, and placement is spent the night;
4) supernatant is got in the mixed solution spinning under the condition of 3500r/min after placement is spent the night, and discards red-brown precipitation;
5) absolute ethyl alcohol of 2.8 times of volumes of adding supernatant in this supernatant places 4 ℃ of refrigerators to separate out the selenizing product, and deposition is got in spinning under the condition of 4000r/min, abandoning supernatant;
6) then to throw out with absolute ethanol washing twice, the centrifuging and taking throw out; In air seasoning below 50 ℃, obtain faint yellow selenizing manna oligosaccharide through pulverizing.
Embodiment 3:
1) selenous acid solution and the mass concentration of using deionized water to prepare 0.1g/mL respectively is 20% manna oligosaccharide solution;
2) manna oligosaccharide solution is placed the vibration tank, and to the HNO that wherein by every gram manna oligosaccharide dry powder adding 2ml volumetric concentration is 10%
3Solution slowly drips selenous acid solution then in manna oligosaccharide solution, and gets solution A in 7 hours in 60 ℃ of following oscillatory reactions, and the volume ratio of selenous acid solution and manna oligosaccharide solution is 7: 5;
3) FeCl of the 1mol/L of adding capacity in reacted solution
3Solution is with the NH of pH=10
3-NH
4The Cl damping fluid transfers to 6～7 with pH value of solution, forms red-brown precipitation, and placement is spent the night;
4) supernatant is got in the mixed solution spinning under the condition of 3500r/min after placement is spent the night, and discards red-brown precipitation;
5) absolute ethyl alcohol of 2.3 times of volumes of adding supernatant in this supernatant places 4 ℃ of refrigerators to separate out the selenizing product, and deposition is got in spinning under the condition of 4000r/min, abandoning supernatant;
6) then to throw out with absolute ethanol washing twice, the centrifuging and taking throw out; In air seasoning below 50 ℃, obtain faint yellow selenizing manna oligosaccharide through pulverizing.
Embodiment 4:
1) selenous acid solution and the mass concentration of using deionized water to prepare 0.1g/mL respectively is 20% manna oligosaccharide solution;
2) manna oligosaccharide solution is placed the vibration tank, and to the HNO that wherein by every gram manna oligosaccharide dry powder adding 4ml volumetric concentration is 10%
3Solution slowly drips selenous acid solution then in manna oligosaccharide solution, and gets solution A in 4 hours in 80 ℃ of following oscillatory reactions, and the volume ratio of selenous acid solution and manna oligosaccharide solution is 10: 5;
3) FeCl of the 1mol/L of adding capacity in reacted solution
3Solution is with the NH of pH=10
3-NH
4The Cl damping fluid transfers to 6～7 with pH value of solution, forms red-brown precipitation, and placement is spent the night;
4) supernatant is got in the mixed solution spinning under the condition of 3500r/min after placement is spent the night, and discards red-brown precipitation;
5) absolute ethyl alcohol of 3 times of volumes of adding supernatant in this supernatant places 4 ℃ of refrigerators to separate out the selenizing product, and deposition is got in spinning under the condition of 4000r/min, abandoning supernatant;
6) then to throw out with absolute ethanol washing twice, the centrifuging and taking throw out; In air seasoning below 50 ℃, obtain faint yellow selenizing manna oligosaccharide through pulverizing.
Selenium content is 0.8-4.5mg/g in the gained selenizing manna oligosaccharide product; Through UV scanning and infrared scan analysis revealed; The selenizing manna oligosaccharide still keeps the basic configuration of oligose; Selenium element wherein exists with two kinds of forms, and the one, form the selenium ester structure with hydroxyl generation esterification, the 2nd, in sugar ether key place's open loop formation C-Se-H structure.
Claims (1)
1. the preparation method of a selenizing manna oligosaccharide is characterized in that may further comprise the steps:
1) selenous acid solution and the mass concentration of using deionized water to prepare 0.1g/mL respectively is 20% manna oligosaccharide solution;
2) manna oligosaccharide solution is placed the vibration tank, and to the HNO that wherein by every gram manna oligosaccharide dry powder adding 0-4ml volumetric concentration is 10%
3Solution slowly drips selenous acid solution then in manna oligosaccharide solution, and gets solution A in 30-80 ℃ of following oscillatory reaction 4-12 hour, and the volume ratio of selenous acid solution and manna oligosaccharide solution is 1-10: 5;
3) FeCl of the 1mol/L of adding capacity in reacted solution
3Solution is with the NH of pH=10
3-NH
4The Cl damping fluid transfers to 6～7 with pH value of solution, forms red-brown precipitation, and placement is spent the night;
4) supernatant is got in the mixed solution spinning under the condition of 3500r/min after placement is spent the night, and discards red-brown precipitation;
5) absolute ethyl alcohol of 2～3 times of volumes of adding supernatant in this supernatant places 4 ℃ of refrigerators to separate out the selenizing product, and deposition is got in spinning under the condition of 4000r/min, abandoning supernatant;
6) then to throw out with absolute ethanol washing twice, the centrifuging and taking throw out; In air seasoning below 50 ℃, obtain faint yellow selenizing manna oligosaccharide through pulverizing.
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| CN201010259989A CN101941994B (en) | 2010-08-23 | 2010-08-23 | Method for preparing selenium manno-oligosaccharide |
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| CN201010259989A CN101941994B (en) | 2010-08-23 | 2010-08-23 | Method for preparing selenium manno-oligosaccharide |
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| CN107344953A (en) * | 2017-07-27 | 2017-11-14 | 成都丽璟科技有限公司 | A kind of selenium-containing compound seleno sugar, seleno glucosides and preparation method thereof |
| CN114145393A (en) * | 2020-09-07 | 2022-03-08 | 宁波拜尔玛生物科技有限公司 | Intestinal microecological preparation and preparation method and application thereof |
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| CN1014522B (en) * | 1988-06-10 | 1991-10-30 | 中国科学院生态环境研究中心 | Preparation of selenide of carragheen |
| CN1284509A (en) * | 2000-07-14 | 2001-02-21 | 武汉大学 | Chitosan selenite and its preparation |
| CN1560088A (en) * | 2004-02-26 | 2005-01-05 | 彭祚全 | Preparaton process of glucoside polyose selenide |
| CN101104644B (en) * | 2006-07-14 | 2010-07-21 | 陈艺新 | Preparation for polysaccharide selenite and application thereof |
| CN101654486A (en) * | 2009-09-14 | 2010-02-24 | 杭州万得富生物技术有限公司 | Preparation method of astragalus polysaccharide selenide |
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Non-Patent Citations (1)
| Title |
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| 崔胜云 等.硒化甲壳胺的制备及性质.《延边大学学报（自然科学版）》.2002,第28卷(第3期),171-175. * |
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