CN113072601A - Preparation method and application of functional oligosaccharide glycoside ester - Google Patents
Preparation method and application of functional oligosaccharide glycoside ester Download PDFInfo
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- CN113072601A CN113072601A CN202110338260.XA CN202110338260A CN113072601A CN 113072601 A CN113072601 A CN 113072601A CN 202110338260 A CN202110338260 A CN 202110338260A CN 113072601 A CN113072601 A CN 113072601A
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- oligosaccharide
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- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 72
- -1 oligosaccharide glycoside ester Chemical class 0.000 title claims abstract description 38
- 229930182470 glycoside Natural products 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000007524 organic acids Chemical class 0.000 claims abstract description 41
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 37
- 241001465754 Metazoa Species 0.000 claims abstract description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
- 239000000243 solution Substances 0.000 claims description 35
- 239000012295 chemical reaction liquid Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 238000001179 sorption measurement Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 11
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 230000007413 intestinal health Effects 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 238000012544 monitoring process Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 claims description 2
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- FTSSQIKWUOOEGC-RULYVFMPSA-N fructooligosaccharide Chemical compound OC[C@H]1O[C@@](CO)(OC[C@@]2(OC[C@@]3(OC[C@@]4(OC[C@@]5(OC[C@@]6(OC[C@@]7(OC[C@@]8(OC[C@@]9(OC[C@@]%10(OC[C@@]%11(O[C@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O)O[C@H](CO)[C@@H](O)[C@@H]%11O)O[C@H](CO)[C@@H](O)[C@@H]%10O)O[C@H](CO)[C@@H](O)[C@@H]9O)O[C@H](CO)[C@@H](O)[C@@H]8O)O[C@H](CO)[C@@H](O)[C@@H]7O)O[C@H](CO)[C@@H](O)[C@@H]6O)O[C@H](CO)[C@@H](O)[C@@H]5O)O[C@H](CO)[C@@H](O)[C@@H]4O)O[C@H](CO)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O FTSSQIKWUOOEGC-RULYVFMPSA-N 0.000 claims description 2
- 229940107187 fructooligosaccharide Drugs 0.000 claims description 2
- 235000021255 galacto-oligosaccharides Nutrition 0.000 claims description 2
- 150000003271 galactooligosaccharides Chemical class 0.000 claims description 2
- DLRVVLDZNNYCBX-RTPHMHGBSA-N isomaltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-RTPHMHGBSA-N 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical group O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 claims description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract description 13
- 230000036541 health Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 210000000813 small intestine Anatomy 0.000 abstract description 7
- 210000002784 stomach Anatomy 0.000 abstract description 7
- 210000002429 large intestine Anatomy 0.000 abstract description 6
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- 206010012735 Diarrhoea Diseases 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 241000186000 Bifidobacterium Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 235000014590 basal diet Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000021316 daily nutritional intake Nutrition 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fodder In General (AREA)
- Saccharide Compounds (AREA)
- Feed For Specific Animals (AREA)
Abstract
The invention discloses a preparation method of functional oligosaccharide glycoside ester, which comprises the step of carrying out esterification reaction on functional oligosaccharide and organic acid to generate the functional oligosaccharide glycoside ester. The invention also discloses application of the functional oligosaccharide glycoside ester. The functional oligosaccharide glycoside ester prepared by the invention enables the organic acid and the functional oligosaccharide to pass through the stomach and the small intestine together, and the oligosaccharide and the organic acid are released by the intestinal tract after reaching the large intestine, so that the utilization rate and the use effect of the functional oligosaccharide and the organic acid are improved, the feed cost can be reduced by adding the functional oligosaccharide glycoside ester and the organic acid into the daily ration of animals, the health condition of the intestinal tract of the animals is improved, and the potential threat of excessive consumption of the organic acid to the health of the animals is reduced. The invention belongs to the technical field of animal feed, and is used for improving the utilization rate of functional oligosaccharide and organic acid in the animal feed.
Description
Technical Field
The invention belongs to the technical field of animal feed, and relates to a preparation method and application of functional oligosaccharide glucoside ester, which is used for improving the utilization rate of functional oligosaccharide and organic acid in animal feed.
Background
The intestinal tract of animals is very easy to be stimulated by external adverse conditions in the whole growth period, particularly in the early period, and the growth performance of the intestinal tract is further influenced because the intestinal tract is damaged by proliferation of harmful bacteria.
The antibiotic can kill harmful bacteria in the intestinal tract, effectively improve the health condition of the intestinal tract and improve the growth performance of animals, but can kill beneficial bacteria in the intestinal tract, and the long-term use of the antibiotic can not only lead the pathogenic bacteria to generate drug resistance, but also cause serious food safety problems.
The oligosaccharide is a low-degree polymeric sugar which is formed by connecting 2-10 monosaccharides through glycosidic bonds and has a straight chain or a branched chain, and the oligosaccharide has two major types of functional oligosaccharides and common oligosaccharides. The functional oligosaccharide can promote the proliferation of bifidobacterium coli, increase the content of lactic acid, reduce the pH value of the intestinal tract, further inhibit the growth of harmful microorganisms (such as escherichia coli) and improve the health condition of the intestinal tract. However, the use of functional oligosaccharides alone has not yet been able to achieve a complete replacement of antibiotics.
In actual production, the animal daily ration is commonly added with organic acid besides functional oligosaccharide, and the functional oligosaccharide and the organic acid are used in a matching way to achieve the same effect as antibiotics. However, most of the organic acids are easy to dissolve and absorb, so most of the organic acids are consumed in the stomach and cannot reach the small intestine and the large intestine to play the role of acidification, and the action efficiency is low. Therefore, in order to achieve the antibacterial effect, it is often necessary to add a high amount of organic acid. The addition of high doses of organic acids not only increases feed costs, but also poses potential threats to animal health.
In contrast, functional oligosaccharides are not consumed in the stomach or small intestine as much as organic acids, but can reach the large intestine directly in intact form.
How to enable organic acid to reach the large intestine to play a role like functional oligosaccharide without being consumed in the stomach or small intestine is a technical problem to be solved at present.
Disclosure of Invention
The invention aims to provide a preparation method of functional oligosaccharide glycoside ester, which esterifies oligosaccharide and organic acid to generate the functional oligosaccharide glycoside ester, so that the organic acid and the functional oligosaccharide can completely pass through the stomach and the small intestine together and release the oligosaccharide and the organic acid again after reaching the large intestine, thereby improving the utilization rate and the use effect of the functional oligosaccharide and the organic acid.
It is another object of the present invention to provide an application of the above functional oligosaccharide glycoside ester, which is added to the daily ration of animals to reduce the feed cost, improve the intestinal health of animals and reduce the potential threat of excessive consumption of organic acid to the health of animals.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of functional oligosaccharide glycoside ester comprises the following steps:
firstly, dissolving functional oligosaccharide in deionized water, and then cooling to 20-30 ℃ to obtain a reaction solution A;
secondly, adding alkali liquor into the reaction liquid A to adjust the pH value to 8-9, and then adding organic acid when the temperature is lower than 20 ℃ to obtain reaction liquid B;
thirdly, after the pH value of the reaction liquid B is stable, adding concentrated hydrochloric acid to adjust the pH value to 1-3 to obtain a reaction liquid C;
fourthly, enabling the reaction solution C to pass through a first activated carbon adsorption column to obtain reaction solution D;
fifthly, adding concentrated hydrochloric acid into the reaction liquid D to adjust the pH value to 1-3 to obtain reaction liquid E;
sixthly, enabling the reaction liquid E to pass through a second activated carbon adsorption column to obtain reaction liquid F;
seventhly, dialyzing the reaction solution F for 12-24 hours, and then adding concentrated hydrochloric acid to adjust the pH value to 1-3 to obtain reaction solution G;
eighthly, spray drying the reaction liquid G in inert gas flow, and recovering a crystallization product H to obtain the functional oligosaccharide glycoside ester;
and the first active carbon adsorption column and the second active carbon adsorption column are both pretreated by HCl solution.
The functional oligosaccharide is, by way of limitation, raffinose, fructooligosaccharide, xylooligosaccharide, soybean oligosaccharide, isomaltooligosaccharide, or galactooligosaccharide.
As a second limitation, the organic acid is citric acid, formic acid, acetic acid, propionic acid, butyric acid, lactic acid, or malic acid.
As a third limitation, the alkali solution in the second step is sodium hydroxide or potassium hydroxide solution.
As a fourth limitation, in the first step, the functional oligosaccharide is dissolved in deionized water, then transferred to a jacket cooling reactor, and cooled to 20-30 ℃ under top stirring and continuous pH monitoring to obtain reaction solution a.
As a fifth limitation, in the second step, the rate of adding the organic acid is such that the pH of the entire reaction solution is maintained between 7.5 and 8.5 and the temperature is maintained at <20 ℃.
As a sixth limitation, in the eighth step, N is used as the inert gas2。
In the seventh limitation, in the fourth step and the sixth step, the speed of the reaction solution C passing through the first activated carbon adsorption column and the speed of the reaction solution E passing through the second activated carbon adsorption column are both 0.4L/h to 0.5L/h.
The invention also discloses an application of the functional oligosaccharide glycoside ester prepared by the preparation method of the functional oligosaccharide glycoside ester, which comprises the following steps: the functional oligosaccharide glycoside esters are added to the animal ration for improving the intestinal health of the animal.
Due to the adoption of the technical scheme, compared with the prior art, the invention has the technical progress that:
(1) according to the invention, the oligosaccharide and the organic acid are esterified, and the generated functional oligosaccharide glycoside ester is not dissolved by gastric juice and small intestine juice, so that the organic acid and the functional oligosaccharide can pass through the stomach and the small intestine and release the oligosaccharide and the organic acid in the large intestine, and the use value and the use effect of the functional oligosaccharide and the organic acid are further improved;
(2) the functional oligosaccharide glycoside ester prepared by the invention can be added into animal daily ration for improving the health condition of animal intestinal tract, and only a very low dosage of the functional oligosaccharide glycoside ester is needed, the functional oligosaccharide glycoside ester can have the same effect as the functional oligosaccharide glycoside ester and the organic acid with large dosage which are separately used, so that the feed cost is reduced, the health condition of animal intestinal tract can be effectively improved, and the potential threat of excessive consumption of the organic acid to the health of animals can be reduced;
(3) the yield of oligosaccharide glycoside ester of the invention is about 70-75%, the major loss occurs on the activated carbon column, when precipitation begins, the product collected in the vaporization chamber and filter in the spray dryer, the post-reaction pH control is necessary to keep the organic acid salt in acidic form to facilitate its removal on the activated carbon column, in addition, the spray drying conditions promote volatilization of the free organic acid, further purify the product, the final product has a degree of esterification of 0.70-0.75, and contains a free organic acid salt content of 1.25-2.5%;
(4) the preparation process disclosed by the invention is simple to operate, high in esterification degree, less in impurity of a final product, high in purity and suitable for large-scale industrial production;
the invention belongs to the technical field of animal feed, and is used for improving the utilization rate of functional oligosaccharide and organic acid in the animal feed.
Detailed Description
Preferred embodiments of the present invention are explained below. It should be understood that the preferred embodiments described herein are for purposes of illustration and explanation only and are not intended to limit the present invention.
Example 1 preparation of xylo-oligosaccharide citrate
This example was carried out in the following sequence of steps:
firstly, mixing M130kg of functional oligosaccharide dissolved in V1200L deionized water, then transferred to a volume V2300L jacketed cooled reactor with overhead stirring and continuous pH monitoring, cooled to T1Obtaining reaction liquid A at 30 ℃;
in the step, the functional oligosaccharide adopts xylo-oligosaccharide;
secondly, adding alkali liquor into the reaction liquid A to adjust the pH value1When the temperature is lower than 20 ℃, adding an organic acid solution to obtain a reaction solution B;
the organic acid solution was added at such a rate that the pH of the reaction solution A was maintained at 7.5<pH2<8.5, temperature T<20℃；
In this stepThe organic acid is V350L of citric acid solution with solubility of 60%, and V as alkaline solution4NaOH solution at 30L, ρ 25% w/v;
thirdly, after the pH value of the reaction liquid B is stable, adding concentrated hydrochloric acid to adjust the pH value3Obtaining reaction liquid C when the reaction liquid C is 2.0;
fourthly, enabling the reaction solution C to pass through a first activated carbon adsorption column to obtain reaction solution D;
the first activated carbon adsorption column was an activated carbon column containing M by thorough washing and pretreatment with 0.2M HCl solution3100kg of granular coconut shell charcoal with the grain size of 4 mm; the speed of the reaction solution C passing through the first activated carbon adsorption column is v1＝25L/h；
Fifthly, adding concentrated hydrochloric acid into the reaction solution D to adjust the pH value4Obtaining reaction liquid E when the reaction liquid E is 2.0;
sixthly, enabling the reaction liquid E to pass through a second activated carbon adsorption column to obtain reaction liquid F;
the second active carbon adsorption column is completely the same as the first active carbon adsorption column; the speed of the reaction liquid E passing through the second activated carbon adsorption column is v2＝25L/h；
Seventhly, dialyzing the reaction solution F for 18 hours, and then adding concentrated hydrochloric acid to adjust the pH value to the pH value5Obtaining reaction liquid G as 3;
eighthly, placing the reaction liquid G in inert N2Spray drying in airflow, and recovering crystallized product H to obtain xylooligosaccharide citric acid glucoside ester as white solid.
The purity of the xylo-oligosaccharide citrate prepared in this example was tested to be 74%.
Examples 2-7A method for preparing functional oligosaccharide glycoside esters
Examples 2-7 were prepared using the same procedure as in example 1, except that the specific raw material types and process parameters were varied, and the raw materials and process parameters for examples 2-7 are shown in table 1 below.
Table 1 raw materials and process parameters for examples 2-11
Example 9 application of a functional oligosaccharide glycoside ester
This example provides an application of the functional oligosaccharide glycoside esters prepared in examples 1-8, which are added to animal feed to improve the intestinal health of animals.
Example 10 simulation experiment
The functional oligosaccharide glycoside esters prepared in examples 1 to 8 were added to simulated gastric fluid and simulated intestinal fluid, respectively, and their degradation rates at different times were counted to obtain the results shown in table 2 below:
TABLE 2 simulated gastrointestinal fluid degradation rate
As shown in Table 2, the functional oligosaccharide glycoside ester is formed by esterifying the organic acid and the functional oligosaccharide, which not only can effectively reduce the dissociation of the organic acid in the stomach and enable the organic acid to smoothly reach the intestinal tract to play an antibacterial role, but also can play a beneficial role of the oligosaccharide.
Example 11 feeding experiment
160 healthy and big-sized ternary hybrid piglets with 7.50 +/-0.16 kg are selected. According to the principle that the weights are consistent and the male and female are half, the weight is randomly divided into four groups: control, test I, test II and test III groups, 5 replicates per group, 8 pigs per replicate. The control group was fed a basal diet without antibiotics and test group I, test group II and test group III were supplemented with 100, 200 and 300ppm of xylo-oligosaccharide propionate prepared in example 4, respectively, based on the control group diet. The test period was 28 days. The test results are shown in Table 3.
TABLE 3 Effect of different levels of xylo-oligosaccharide propionate on growth Performance and diarrhea Rate of weaned piglets
| Control group | Test group I | Test group II | Test group III | |
| Initial weight (kg) | 7.38 | 7.58 | 7.35 | 7.70 |
| Terminal weight (kg) | 17.04a | 17.49a | 18.07b | 18.59b |
| Average daily gain (g) | 345a | 354a | 383b | 389b |
| Average daily food intake (g) | 571 | 581 | 593 | 616 |
| Meat ratio of materials | 1.66a | 1.64a | 1.55ab | 1.58ab |
| Diarrhea Rate (%) | 11.98a | 7.29ab | 5.72b | 5.43b |
As can be seen from Table 3, the addition of 200 ppm and 300ppm of xylo-oligosaccharide propionate in the daily ration can significantly improve the daily gain (P <0.05) of the weaned piglets and significantly reduce the feed conversion ratio and diarrhea rate (P <0.05) of the weaned piglets. Therefore, the xylo-oligosaccharide propionate can improve the growth performance of weaned pigs and reduce the diarrhea rate.
This example is only a representative example of the xylooligosaccharide propionate prepared in example 4, and actually the same effect can be obtained by feeding the xylooligosaccharide propionate prepared in examples 1 to 3 and 5 to 8.
Claims (9)
1. A preparation method of functional oligosaccharide glycoside ester is characterized by comprising the following steps in sequence:
firstly, dissolving functional oligosaccharide in deionized water, and then cooling to 20-30 ℃ to obtain a reaction solution A;
secondly, adding alkali liquor into the reaction liquid A to adjust the pH value to 8-9, and then adding organic acid when the temperature is lower than 20 ℃ to obtain reaction liquid B;
thirdly, after the pH value of the reaction liquid B is stable, adding concentrated hydrochloric acid to adjust the pH value to 1-3 to obtain a reaction liquid C;
fourthly, enabling the reaction solution C to pass through a first activated carbon adsorption column to obtain reaction solution D;
fifthly, adding concentrated hydrochloric acid into the reaction liquid D to adjust the pH value to 1-3 to obtain reaction liquid E;
sixthly, enabling the reaction liquid E to pass through a second activated carbon adsorption column to obtain reaction liquid F;
seventhly, dialyzing the reaction solution F for 12-24 hours, and then adding concentrated hydrochloric acid to adjust the pH value to 1-3 to obtain reaction solution G;
eighthly, spray drying the reaction liquid G in inert gas flow, and recovering a crystallization product H to obtain the functional oligosaccharide glycoside ester;
and the first active carbon adsorption column and the second active carbon adsorption column are both pretreated by HCl solution.
2. The method of claim 1, wherein the functional oligosaccharide is raffinose, fructo-oligosaccharide, xylo-oligosaccharide, soybean oligosaccharide, isomalto-oligosaccharide, or galacto-oligosaccharide.
3. The method of claim 1 or 2, wherein the organic acid is citric acid, formic acid, acetic acid, propionic acid, butyric acid, lactic acid or malic acid.
4. The method for preparing functional oligosaccharide glycoside ester according to claim 1 or 2, wherein the alkaline solution in the second step is sodium hydroxide or potassium hydroxide solution.
5. The method for preparing the functional oligosaccharide glycoside ester according to claim 1 or 2, wherein the first step is to dissolve the functional oligosaccharide in deionized water, then transfer the solution to a jacket cooling reactor, and cool the solution to 20-30 ℃ under top stirring and continuous pH monitoring to obtain the reaction solution A.
6. The method of claim 1 or 2, wherein the organic acid is added at a rate such that the pH of the entire reaction solution is maintained at 7.5-8.5 and the temperature is maintained at <20 ℃.
7. The method for preparing a functional oligosaccharide glycoside ester as claimed in claim 1 or 2, wherein in step eight, N is used as inert gas2。
8. The method for preparing functional oligosaccharide glycoside ester according to claim 1 or 2, wherein in the fourth step and the sixth step, the speed of the reaction solution C passing through the first activated carbon adsorption column and the speed of the reaction solution E passing through the second activated carbon adsorption column are both 20L/h-25L/h.
9. The use of the functional oligosaccharide glycoside ester obtained by the process of any one of claims 1 to 8, wherein: the functional oligosaccharide glycoside esters are added to the animal ration for improving the intestinal health of the animal.
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